In today’s episode, I sit down with investor, entrepreneur, and content creator, Sahil Bloom (in front of a live audience) to unpack the key strategies and lessons that will help you achieve longevity and sustainability in the creator economy.Sahil has had a fascinating journey, transitioning from the world of private equity to making a name for himself in the creator economy (his bi-weekly newsletter alone has more than 400K subscribers). Upon entering this new sector, Sahil found himself occupied with the question of how to ensure longevity and set about putting together the ideal business operating system for content creators. In today’s conversation, you’ll get a behind-the-scenes look at how Sahil built a thriving ecosystem as a content creator by acquiring businesses that would resonate with his audience and partnering with the right collaborators. You’ll also hear Sahil’s answers to live audience questions where he sheds light on finding the right partner, knowing when to pivot, and the future of the creator ecosystem.In this episode, you'll learn: How Sahil became one of the first people to popularize the use of long-form on Twitter Why to focus on building an audience with whom your work resonates rather than chasing vanity metrics How to figure out if you're creating inspiration-driven content operation-focused content (and where you lie on the spectrum) How to escape the need to create new content daily by putting strategies in place How to use flywheels as the operating system for your business How to find the right collaborators How Sahil uses agencies to turn cost centers into profit centers When to pivot on a project or company Habits for creating and managing your time as a creator Links & Resources:The Sweaty StartupWait But WhyJustin WelshTim FerrissSahil Bloom Links:Sahil’s websiteFollow Sahil on LinkedInFollow Sahil on TwitterFollow Sahil on InstagramFollow Sahil on YouTubeFollow Sahil on TikTokSubscribe to Sahil’s newsletter

Today, I talk to Darrell Vesterfelt, who is a longtime friend who helped grow ConvertKit in our craziest growth times (from $100,000/mo when he joined to $500,000/mo in just over a year).Darrell is one of the best marketers I know. He is the Founder and former CEO of Good People Digital, the Co-Founder of Homestead Living, and Co-Founder and COO of the School of Traditional Skills.In this episode, Darrell breaks down the goal and execution of an online summit that accumulated an astonishing 101,000 attendees as a brand-new brand! Tune in to find out why you can’t have a marketing strategy without value and vice versa.In this episode, you'll learn: Darrell’s transition from New York to homestead; how his marketing skills translate to homesteading. The importance of authenticity in the homesteading world. A rundown of Darrell’s various businesses. The publication and publishing house, Homestead Living: what inspired it and where it’s going.  The structure, marketing strategy, execution, and conversion rate of the School of Traditional Skills Summit. The best marketing strategy according to Darrell. Links & Resources:Homestead LivingHomestead Living on InstagramSchool of Traditional SkillsHomesteading FamilyGood People DigitalEverything Worth PreservingDarrell Vesterfelt Links:Darrell’s websiteFollow Darrell on LinkedInFollow Darrell on TwitterFollow Darrell on Instagram

In today’s episode, I’m joined by PJ Taei, Founder and CEO of Uscreen, an all-in-one video monetization platform for content creators that helps them build their brands and grow their businesses. The creator economy has changed a lot since PJ first founded Uscreen in 2015. And in that time PJ has managed to grow Uscreen to $20 million a year in revenue, representing sought-after clients and their channels, like Yoga with Adrienne and Justin Rhodes’s streaming platform, Abundance Plus. Our conversation gets into some pretty fascinating topics, like what to do when major competitors enter your field, the trial and error involved in getting your pricing right, and why true fans are so valuable for content creators looking to monetize. PJ also sheds light on what motivated him to bootstrap his company and expands on why it’s so important to stay in touch with the needs of your customers as you grow!In this episode, you'll learn: How Uscreen supports creators by helping them sync their offerings on one platform. What helped PJ recognize the need for a service like Uscreen. When to fear a major competitor coming in and why you should never underestimate a small company. The importance of continued focus on the customer as you grow along with actionable advice on how to stay in touch with their needs. How to find the right balance between trial periods, free content, and attracting paying customers. Why PJ decided to bootstrap instead of pursuing funding and what he has learned from the experience. Links & Resources:UscreenUscreen on YouTubePJ Taei’s Links:PJ’s websitePJ’s emailFollow PJ on LinkedInFollow PJ on TwitterFollow PJ on YouTube Listen to PJ’s Podcast

In this episode, I talk to Susie Bulloch, who runs Hey Grill, Hey, which started as a wildly successful food blog (to the tune of a million dollars or more a year in revenue). Then she did something that I absolutely love: she used her online business to kickstart a physical products company. Her sauces and rubs company in the barbecue space is now about to overtake the blog in revenue.The online world of content creation is vastly different to the product manufacturing space, and as Susie explains, she is grateful that she didn’t know too much before she made the transition. Her top piece of advice for anyone interested in doing the same thing is to make products with the intention of fulfilling a need, not just because you have an audience online. Susie describes herself as “terrifyingly driven,” and during our conversation, she talks about how she went from “I could never” to doing it all, the importance of celebrating business milestones, the value of having someone ask you, “Why?” regularly on your entrepreneurial journey, and her goal of increasing the representation of  women-owned brands in the barbeque space!In this episode, you'll learn:  The value in working for other people before starting your own company.  Why it’s always worth taking the time to be grateful for the journey you are on and celebrating your achievements. What the life of a “terrifyingly driven” entrepreneur looks like.  How to build trust within your community so they are happy to pay for your offerings. The only piece of advice Susie would give to someone interested in transitioning from online content creation to product manufacturing.  Links & Resources:Hey Grill, HeyThe Grill Squad‘The Billion Dollar Creator’Susie Bulloch Links:Follow Susie on TwitterFollow Susie on FacebookFollow Susie on InstagramFollow Susie on YouTubeSubscribe to Susie's Grill Squad

Today, I sit down with the Head of Deliverability at ConvertKit, Alyssa Dulin, to shed some light on the often mysterious game of getting your email into the right inbox. Alyssa's expertise about what creators need to focus on and the most recent developments in the email marketing space can truly take your company's reach to the next level!Deliverability has always been a huge part of what we offer at ConvertKit, and Alyssa unpacks the most important pieces of this puzzle, covering sender reputation, effective cadences, and setting and delivering on expectations. As with so much of our philosophy, it is all about playing the long game over short-term wins and shiny statistics. You’ll get a look behind the scenes at how the world of email actually operates and evolves, the important conversations that happen between providers, as well as some helpful practical tips and common mistakes to avoid. Be sure to join Alyssa and me for this illuminating chat. In this episode, you'll learn: The biggest factors that contribute to reaching your audience's inbox. A simple and comprehensive definition of deliverability. How to think about the important aspect of reputation management.  The real value of custom domains and dedicated IPs.   Links & Resources:ConvertKit's Creator NetworkEventbriteWarby ParkerEmmaCM GroupTim FerrissSusan CainJames ClearBitlySpamhausM3AAWGFigmaSubstackSparkLoopAlyssa Dulin Links:Follow Alyssa on TwitterListen to Alyssa's podcastSubscribe to Alyssa's newsletter

Today I’m talking with Thomas Frank. Thomas built a YouTube channel called College Info Geek to over a million subscribers. Since then, he’s rebranded and grown the channel to nearly 3 million subscribers. He’s also built a massive business around courses and Notion templates.In this episode we talk about making a pivot as a creator. Thomas has an interesting and understated approach that’s worked quite well. We also talk about the Notion templates he’s selling, the YouTube productivity channel he started strictly about Notion, and how it’s driving hundreds of thousands of dollars in sales per month.Thomas also explains why it’s easier getting started on YouTube today than it was 10 years ago, and I get Thomas’ candid thoughts on how Gumroad’s new pricing has affected his business and creators in general.In this episode, you’ll learn: Why now is a great time to get started on YouTube How to pull off a successful rebrand of your creator business Why your subscriber count isn’t as important as you think Was Gumroad’s price increase a mistake? Thomas’ Links (H5) Thomas’ website Follow Thomas on Twitter Subscribe to Thomas’ YouTube channel Download Thomas’ Notion templates Check out Thomas’ Notion YouTube channel Thomas’ Nebula.tv content Follow College Info Geek on Twitter Thomas’ Skillshare page

In this episode I talk to Brian Feroldi. Brian is an incredible creator in the investing space. He Tweets about money, investing, and self-improvement. He also has a free newsletter with over 40,000 subscribers.Today Brian talks about his recent experience migrating his newsletter to ConvertKit. He’s also a member of the ConvertKit Sponsor Network. I haven’t said much about the Sponsor Network, so Brian shares how he’s using it to book sponsors.The bulk of our conversation, however, is about Twitter and how he’s grown his account to over 400,000 followers. Brian has an interesting idea using your Twitter profile as a sales page, and he explains why conversion rates are important. We also pull up my Twitter profile and Brian gives it a tear down live on the show.In this episode, you’ll learn: How to get more followers on Twitter Twitter profile strategies that increase your conversion rate Why your Tweets aren’t getting more impressions How to write Twitter threads that people will share Links & Resources (H5) ConvertKit Sponsor Network Sahil Bloom James Clear Tim Urban Blake Burge Austin Lieberman Brian’s Links (H5) Brian’s newsletter Follow Brian on Twitter Connect with Brian on Facebook Brian is on Instagram Check out Brian on YouTube Brian’s LinkedIn page

The podcast is back! Today I’m talking with Turner Novak. Turner is someone I’ve followed for a long time. He has an amazing Twitter account where he drops hilarious memes, talks about life as an investor, and makes fun of venture capitalists and founders.He also posts deep dives on companies like Snapchat about how their earnings work, what’s going on in TikTok ads, and a lot more. It’s an interesting balance, and he does all this while investing in early-stage companies as a venture capitalist.In today’s episode Turner and I talk about how he creates content. We get into how he uses his funnel to raise capital, and how to generate the highest return on investment (ROI) for your audience. We also talk about how he grew to 130,000 followers on Twitter, why he failed to get a job in venture capital and had to start his own firm, and how to create a successful newsletter.In this episode, you’ll learn: Easy ways to grow your newsletter audience How Turner varies his content to get more engagement Why getting to know your audience is so important How Turner used writing to expand his venture capital network Turner’s Links & Resources (H5) Subscribe to Turner’s newsletter, The Split Follow Turner on Twitter Banana Capital’s website Follow Banana Capital on Twitter

In this episode I talk to Katelyn Bourgoin. Katelyn is a creator and entrepreneur. She’s built several successful companies and agencies, and built a consultant company that she later sold.We dive into why customers buy, and how to market and sell to them through the Jobs-to-be-Done framework. Katelyn has a wealth of marketing knowledge she shares with us today.We talk about different business models. We get into why you should focus on selling checklists, cheat sheets, and outcomes rather than the traditional video courses. We also talk about how she grew her newsletter to 10,000 subscribers, and got to over 50,000 followers on Twitter.In this episode, you’ll learn: Tips and strategies for acquiring more users A subtle mindset shift to make your marketing more effective What content should be free, and what should be paid for Why Katelyn transitioned away from launches and courses Links & Resources Episode 061: Rachel Rodgers – Simple & Consistent: How To Build an 8-Figure Business April Dunford Nathan Barry: Authority Katelyn Bourgoin’s Links Customer Camp Follow Customer Camp on Twitter The Why We Buy newsletter Jobs-to-be-Done The Trigger Technique Twitter thread about The Trigger Technique Follow Katelyn on Twitter

In this episode I talk to Laura Roeder. Laura and I have been friends for a long time. I’ve learned so much from her, and it’s great to have her on the podcast.Laura started an online community and a course called Creating Fame. She’s done a bunch of stuff in the internet space. She’s one of the people who’s been doing it since the early days.She got into software with a company called MeetEdgar, which is a social media scheduling service, and grew it into a successful company before selling it. She recently started another company called Paperbell. Paperbell is the all-in-one software that solves all the problems of running a coaching and consulting business.There’s so much to learn from Laura. I love her direct, blunt style. She’s given me great advice over the years, and you get to tune in as we jump on a call, hit record, and start catching up.In this episode, you’ll learn: Benefits of choosing a narrow niche for your business Common branding mistakes to avoid when starting out Laura’s advice for writing great copy Tradeoffs between hiring freelancers and employees Links & Resources Mama Gena MeetEdgar Laura Roeder’s Links Laura’s website Follow Laura on Twitter Laura is on Instagram Paperbell Follow Paperbell on Twitter Paperbell is on Instagram Follow Paperbell on Facebook Check out Paperbell on Pinterest

In this episode I talk to Justin Moore. Justin is a Sponsorship Coach & the founder of Creator Wizard, a school & community that teaches you how to find & negotiate your dream brand deals.In today’s episode Justin reveals how narrowing in on sponsorship coaching was a huge boost for his business. We talk about him growing multiple audiences between different YouTube channels (he and his wife, April, have well over a million combined followers on YouTube).My favorite part of the episode is when we dive into From Boise, my side project newsletter. Justin breaks down what we’re doing wrong with sponsorships, how we should be selling them, and how there’s quite a bit more to be earned. We also dive into the way he runs his newsletter and how he’s grown it.In this episode, you’ll learn: The differences and similarities between sponsorships and newsletters Justin’s tips for starting your newsletter and getting traction How a simple change in Justin’s Twitter headline led to amazing growth for his brand Why you need to charge your sponsors different amounts Links & ResourcesDeepak Malhotra: Negotiation Genius: How to Overcome Obstacles and Achieve Brilliant Results at the Bargaining Table and Beyond Justin Moore’s Links Justin’s website Justin's newsletter Follow Justin on Twitter Join Justin’s group on Facebook Justin’s TikTok Justin is on Instagram Check out Creator Wizard on YouTube Trending Family AprilJustinTV on YouTube

In this episode I’m joined by Kaya Yurieff. She is the Creator Economy Newsletter writer for The Information. It’s the publication I read when I want to know what’s going on in startups and funding, learn about Spotify’s latest launch, find out what’s going on with Instagram, and things like that.Kaya has a great approach. I love her writing. I love the way she profiles both individual creators and the moves happening from big businesses in the creator space.We talk about her writing process and her system for publishing four days a week. We talk about how they’ve grown the newsletter and what they pay attention to for monetization. We also talk about what it means to be a creator through crises like the pandemic, the social justice issues of the last few years, and now the war in Ukraine.In this episode, you’ll learn: Tips for finding your niche in a crowded field How to get more paid subscribers Benefits of adding visual content to your newsletter How to balance free content and paid content Links & Resources Embedded Kate Lindsay’s post on Embedded: You don't need to post through a crisis Kaya Yurieff’s Links The Information’s Creator Economy Newsletter Follow Kaya on Twitter

In this episode I talk to Wes Kao, co-founder of altMBA. Her latest startup is called Maven, and it's all about cohort-based courses.Wes is fantastic at course design. Before Maven, she did a bunch of amazing things working with a lot of different creators.We talk about the State Change Method, which is something I use to make my presentations much more interesting. We talk about building an audience on Twitter. We also talk about course design, cohort-based courses, and a lot of other fun things.In this episode, you’ll learn: Tips for writing short-form content that boosts engagement A big advantage Twitter gives you over other platforms How to know if your content is ready to publish Why cohort-based courses are so lucrative Links & Resources (H5) Seth Godin altMBA Gagan Biyani Wes Kao’s Links (H5) Maven Wes’ website Follow Wes on Twitter Wes’ blog post: Course Mechanics Canvas: 12 Levers to Achieve Course-Market Fit Wes’ blog post: The State Change Method: How to deliver engaging live lectures on Zoom

On today’s show I’m talking with Brennan Dunn. Brennan is a longtime friend. He's been around since the very early days of ConvertKit. He helped me review pull requests from our very first developers.These days Brennan is an expert in all things email marketing and automation. He’s fantastic at segmenting lists, personalizing content, using Liquid, and other advanced techniques to create a custom experience for subscribers.We talk about some of the ways you can gradually get into automation. We go over some examples of the advanced things Brennan does with Liquid and snippets to create custom experiences for subscribers. We also talk about how you can earn more money from email with these systems, and much more.In this episode, you’ll learn: Strategies for tailoring your website to boost engagement & sales How to free up more time so you can focus on growing your audience Brennan’s tips for creating and sharing the right content for your audience How to make your repurposed content feel fresh & relevant Links & Resources ConvertKit Shopify’s Liquid RightMessage Brennan Dunn’s Links Create & Sell Creator Email Template Pack Double Your Freelancing Brennan’s book: Double Your Freelancing Rate Mastering ConvertKit Follow Brennan on Twitter

In this episode I talk to Sahil Bloom. This is Sahil’s second time on the show. He’s doubled his audience from an already large number since then, and he’s now a full-time creator.Sahil is someone I’d love to have on the show every six months or every year. He’s putting out incredible content. I’ve probably learned more from Sahil in the last few months than I have from any other person.We talk about Twitter growth, monetization, growing a podcast, and newsletters. I also try to sell him on switching to ConvertKit. You can be the judge of how well I did to convince him.In this episode, you’ll learn: Two game-changing habits that can lead to big results How Sahil categorizes his content for more engagement Sahil’s strategies for growing a new podcast How Sahil monetizes his newsletter Links & Resources (H5) James Clear Shane Parrish The Generalist (Mario Gabriele) Greg Isenberg The Tim Ferriss Show, episode 362: Talent Is the Best Asset Class — Graham Duncan Sahil Bloom’s Links (H5) Follow Sahil on Twitter Listen to Sahil’s podcast, Where It Happens Visit Sahil’s website

On today’s show I talk to Isa Adney, a resident storyteller at ConvertKit.Isa came to ConvertKit as our webinar producer. You get to hear the arc of what she was doing before, how she joined the team, and how it morphed into her current role.Isa is very good at systems. She shares how she uses systems to free up time for creative activities. We also talk about reusing content, and how to create systems and flywheels to make one piece of content work across many platforms.In this episode, you’ll learn: How to connect with popular creators you admire The best medium for building a relationship with your audience Isa’s advice for hosting workshops and webinars How Isa utilizes systems to create content across multiple mediums Links & Resources (H5) ConvertKit ConvertKit podcasts Don Hahn: Brain Storm: Unleashing Your Creative Self Kimberly Brooks The Nathan Barry Show 053: Kimberly Brooks – Taking Intentional Breaks To Reignite Creativity Harlem's Fashion Row (HFR) The Nathan Barry Show 026: Khe Hy – How You Can Do $10,000/Hr Work ConvertKit Creator Stories Isa Adney’s Links (H5) Follow Isa on Twitter Isa is on Instagram Follow Isa on TikTok

In this episode, I talk to Ellen Hyslop, Co-Founder of The Gist.The Gist is a newsletter all about sports, written entirely by women. Ellen and her co-founders have scaled a massive team to 20 people. They’ve grown The Gist to almost 400,000 subscribers, and they’re earning fantastic revenue from it.Ellen talks about how they grew The Gist in the early days. She also talks about their process of testing, how they launched with a launch party, and a bunch of other things.In this episode, you’ll learn: How to get subscribers when you’re first starting out Why you need to create a style guide for writing your newsletter Tips for growing your newsletter to 400K subscribers When niching down can lead to more revenue Links & Resources The Gist Co-Founder Jacie deHoop The Gist Co-Founder Roslyn McLarty Ellen Hyslop’s Links The Gist website The Gist newsletter The Gist of It podcast Follow Ellen on Instagram

In this episode I talk to Rachel Rodgers. Rachel is an attorney turned business coach. She’s someone I’ve admired and respected for a long time. She helps small business owners understand contracts and the legal side of running a business, and helps them scale their business.Rachel is a lot of fun, and she’s brilliant at business. She’s my hero because of the way that she approaches scaling a massive and successful business, and how she thinks about brand and everything else.On today’s show we talk about why business partnerships are a bad idea. Rachel shares her keys to building a successful membership community, and the benefits of publishing a book. We also talk about why you should take expensive vacations, how to build a great team, and much more.In this episode, you’ll learn: Why offering more products can hurt you in the long run Rachel’s clever method for scaling a business The relationship between current events and a successful creator business How Rachel builds an effective team Links & Resources (H5) Nathan Barry: Authority Denise Duffield-Thomas ConvertKit Rachel Rodgers’ Links (H5) Hello Seven The Hello Seven podcast We Should All Be Millionaires: The Club We Should All Be Millionaires: A Woman’s Guide To Earning More, Building Wealth, and Gaining Economic Power Small Business Bodyguard Follow Rachel on Twitter Rachel is on Instagram

In this episode I talk to Reid DeRamus. He comes from the video streaming world of Hulu, HBO Max, and Crunchy Roll. His background in data analysis helped these companies grow their streaming services.Now he’s taking what he learned into the creator space to help people with their paid newsletters and courses, bringing these growth habits and growth techniques into their solo or small team creator businesses.We spend this episode riffing on business models, and the analytics that you should pay attention to as an individual creator. We also discuss branding, positioning, and local meetups. It’s a fun episode that I think you'll enjoy.In this episode, you’ll learn: Tips for developing your brand and community Reid’s process for curating content How to get your work in front of an audience The path to over 500K subscribers Links & Resources Patreon Wait But Why Crash Course on YouTube minutephysics on YouTube MinuteEarth on YouTube Reid DeRamus’s Links Follow Reid on Twitter Yem

In this episode, I talked to Samir Chaudry. Samir is the co-host of the popular YouTube channel, Colin and Samir. He and his business partner, Colin Rosenblum, have built a really interesting enterprise. It’s been fun getting to know them.We talk about how they built and structure their entire business, and what drives revenue. Then we get into storytelling, and at the end we even talk about designing the perfect day, what’s driving growth on YouTube, and much more.They’ve got a show, they’ve got a newsletter, a bunch of different stuff. It’s a fun story of two people who were shining in a specific niche, took what they learned from that experience, and are serving the broader community with their knowledge and wisdom.In this episode, you’ll learn: How to avoid being overwhelmed as a creator How Samir & Colin developed a culture around their content Tips for curating your content The journey to over 500K subscribers on YouTube Links & ResourcesConvertKitSamir Chaudry’s Links Follow Samir on Twitter Colin and Samir on YouTube The Colin and Samir Show on Apple Podcasts The Colin and Samir Show on Spotify The Publish Press newsletter Colin and Samir on Instagram

Andrew Gazdecki is the founder and CEO of MicroAcquire, the world’s most founder-friendly startup acquisition marketplace. MicroAcquire helps entrepreneurs buy and sell startups.After founding and later selling two successful startups, Andrew decided there needed to be a better way to connect buyers and sellers in the startup marketplace. He founded MicroAcquire to fill this void in the startup acquisition arena.In this episode, Andrew shares how he grew his Twitter audience from 30,000 to 70,000 followers in a few short months. He uses his connections with others, his partnerships, his brand, and savvy marketing techniques to boost engagement and attract followers. It’s a fun and entertaining episode, and I think you’re going to enjoy it.In this episode, you’ll learn: The one thing you should spend at least half of your startup’s budget on Proven strategies and tactics to grow your Twitter account How to bootstrap your business and retain your autonomy Links & Resources TechCrunch Cameo Effie Empire Flippers Flippa Bizness Apps Sam Parr Stripe Baremetrics ChartMogul Bumble Brandarrow Bootstrappers.com Y Combinator Salesforce Nick Huber David Cancel Josh Pigford Clearco AngelList Avaloq Naval Ravikant Dharmesh Shah The Ladders of Wealth Creation blog post Andrew Gazdecki’s Links Follow Andrew on Twitter Follow MicroAcquire on Twitter Episode Transcript00:00:00 Andrew:I’m a big fan of stair-stepping and entrepreneurship. One of my favorite tweets that I’ve ever written is, “Start with an agency, get to cashflow positive, and then bootstrap an asset—whether that’s a SaaS company or your e-commerce business—sell that asset, become financially secure, and then do whatever you want.”Along the way, you prepare yourself for the next stage of business. 00:00:35 Nathan:In this episode, I talked to Andrew Gazdecki, from MicroAcquire. Andrew started a couple other businesses and sold two of them. In that process, he decided there needed to be a better way to buy and sell businesses. So, that’s where MicroAcquire came from. Their marketplace originally focused specifically on SaaS businesses, but they broadened to all of software.The reason I want to talk to him—he doesn’t write a traditional newsletter or something like that—but he uses audience really well to grow MicroAcquire. He uses his personal brand connections with others, partnerships, a bunch of fun things.We get into how he grew his Twitter audience from 30,000 followers just a couple months ago, to over 70,000. His approach to Twitter, some of the arguments or beefs that he started with TechCrunch and others, and where he thinks those lines are.We also get into how he uses Cameo; he has these great ads announcing partnerships and others from Russ Hanneman on Silicon valley talking about this, and they’re really entertaining.So, there’s a lot of fun things in this episode, and I think you’re going to like it.I’ll get out of the way, and we’ll dive in.Andrew, welcome to the show.00:01:41 Andrew:Thanks for having me, Nathan. Always a pleasure to be chatting with you. 00:01:44 Nathan:There are a lot of companies in the brokerage/help-me-sell-my-business space. I think of Effie International, Empire Flippers, Flippa, all of these. So, one, you’re going into a really crowded market with MicroAcquire, and then, two, you’re coming at it like you’re a force of nature.Sam Parr and I we’re actually talking about this, of how some people start a project and it’s like, “Oh, I’m going to do this thing.” And then other people do effectively the same thing. I mean, it’s different in a lot of ways, right? But the same category, and come in and just completely dominate, and grow so fast, and it feels like a fundamentally different thing.What’s your take on that, of coming into a crowded space, and then the amount of momentum that you’ve come in with?00:02:34 Andrew:Yeah. I have a lot of respect for all those companies that you mentioned, and appreciate the compliment.The market that is specifically acquisitions hasn’t seen a lot of innovation in a decade. Two of the businesses you mentioned are service businesses, Flippa being a marketplace. I looked at that, and I just thought, there’s an angle here where sellers could benefit more than the buyers, and I felt buyers were benefiting. So, I took a left while everyone was going right.Then coming in from an entrepreneur’s view instead of a buyer’s view, or an investment bankers view, or an MNA advisor view, this was me saying, okay, I’m gone through two acquisitions, I think I have a few unique insights into what it would take to make me comfortable putting my business, generating millions of dollars, on a new marketplace. Then, what information and educational pieces would I need to feel comfortable to facilitate an acquisition.So, I just built what I felt acquisition should be. We still have a long way to go. We’ve done a really good job of connecting buyers and sellers, and all the acquisitions are facilitated off platform. We’ve been working on a lot of tooling to really add value to the acquisition, if that makes sense.So we’re looking to innovate on things like due diligence or even simple items like writing a letter of intent or streamlining escrow, because everyone complains about escrow.com. so yeah, I mean, sometimes it just happens in markets. Like a new entrant comes in with a different angle towards the problem And different viewpoint. and I think my unique, insight there was just, I had been on. The side of the table that maybe the other, companies had not. but it’s also, a giant market. So I, think, arising boat lifts all tides. So, you know, we’re here to my require. I just made my group or to help entrepreneurs get acquired and, and, succeed.And so, I think also as, you know, Mike require pick steam and helps everyone else in the market as well. So, but, yeah, I don’t have a good answer to that. I don’t know. I think if I, if I, this, this will sound cheesy, but you know, I, I I’d like to say I built my group hire would love, like I launched it in the middle of the pandemic. I didn’t have a business model. I had no idea how I was going to make money. I just knew I wanted to work with entrepreneurs and startups. And the rest is kind of history, you know, along the way, talking to customers, getting feedback from them, pretty much everything we do is basically feedback from customers.I’m not Steve jobs or anything like that. So I can’t read people’s minds. So I ask what, what ideas do you have? but yeah, it’s been, it’s been a fun journey so far. my group is about to turn two, which is pretty wild. 00:05:56 Nathan:That first version, that you launched, what did that look like? What, what was the very early stages of it? 00:06:02 Andrew:The first version was, it was just a simple marketplace with a couple of. Changes that I haven’t seen in the market. One was privacy and anonymousy and then no fees or commissions for founders. So it was the first marketplace where you could meet buyers and sell your business without paying a 15% commission like you typically would with a broker or something like that.So I think that was kind of a change. And our business model today is we charge buyers for access to the platform to connect with sellers and, you know, having negotiations that lead towards negotiations. But yeah, the first version, required a lot of vetting of the buyers. Every buyer needed like a LinkedIn profile.Some people have complained about that, but I personally would never sell my business as someone, without a LinkedIn profile. I need to know where you worked, like you know, do you have anyone that’s bad for you? not just like John 9, 9, 2, 4 5. You know, I need to know, who you are. and we’re going to add other ways of verification, but I think that was a big one. and then also real-time metrics integration. So when we launched, you could connect like Stripe and chart, mobile and probable and bare metrics to get like a real, like a nice, pretty graph, like the revenue to help with due diligence. and then also founders and everything was private. So you didn’t know what the business was.And as a founder, you had complete control over the process. So when you were with a broker, sometimes it could be kind of showing your business to a lot of peopleAnd you may not know who those people are. they could even be competitive to your business. And so I think what Mike required did that kind of, and I’m just guessing here because I haven’t really liked. Taking a step back and then like, what did we do? Right. you know, I’m usually thinking about what can we be doing better? we really put the founder in control. You know, they were the ones able to choose which buyers to speak to. they were the ones able to share which information they wanted to and which information they did not want to share. And again, it was completely free. So it was very low friction to get onto the platform. And then I think just the, the high, the caliber of buyers and the caliber of listing. So we vet every listing. We vet every buyer. Now that registers as a micro require premium buyer, that’s where you can contact sellers. so I think it was just kind of like, you know, going from let’s just call it like a car dealership to like a Ferrari shop that makes sense where all the cars are, That it, and if you want to know who the owner is, you have to pay for that access, but it was a very specific towards startups, specifically SaaS.So I think that’s another thing that I’m thinking of now is we, we went very narrow at the beginning, very narrow. So we were very specific on, specifically, bootstraps, SaaS companies.00:08:59 Nathan:Yeah. I think the approach in different marketplaces is always interesting when, you know, a marketplace is how businesses has like is a generic category, but then the twist on it, of, the seller not paying anything. And it being the buyer who pays, you know, a subscription for access. Why I think that that makes for an interesting twist, because then you’re going to have this much higher pipeline of, you know, high quality businesses to look at.And so if a seller is paying for that, that makes sense. It reminds me of like, Bumble as a dating app being like, yep. So within the category of dating apps, but, women have to send the first message, you know, and, and like, that little bit of a twist makes it the marketplace feel, very different and changes the dynamics of. 00:09:40 Andrew:Yeah. I was going to say something, someone called micro fire shark tank, like if shark tank and dinner had a kid, I thought that was kind of an interesting analogy. but yeah, I’d say the, the key. The unique insights I had was again, like, from my perspective, if I’m going to list a business, I need to know who’s seeing my information. I want to be in control of, you know, what information is being disclosed or being displayed publicly. and I don’t want to commit until I really know, the quality of the buyers. And so that I think was very appealing to just being an entrepreneur. I think I. You know, understood the needs of other entrepreneurs and just kind of got it.Right. But I’m not gonna lie. When I, when I first launched it, I have this, I keep a journal that I update every month. It’s not like a weird, you know, Hey dear diary thing. It’s I do like, what’s going really well. What are some things I’m worried about? and then things I’m grateful for, just to, you know, kind of keep it story log of my life. And before I launched my group wire, I actually, cause this idea had been attempted before, like a real startup acquisition marketplace. I think some of the other market places are more, geared towards, you know, content sites and domains and 00:11:07 Nathan:Yeah, 00:11:08 Andrew:Affiliate websites, but not real. Startups like SaaS companies, e-commerce companies, crypto companies, we’ve moved into a number of different categories.But, I wrote in my journal, I was like, I don’t know if this is going to work, but at least it looks good. cause I, I just thought it needed to exist so bad for entrepreneurs that, we put a lot of thought into user experience and design. So it felt modern. You know, when you’re working with startup founders, you kinda, you know, you want to really build trust, like yeah, if you’re going to sell your business with us, your startup, you know, we also, we know how to build startups as well, and design them well and make them feel like something like this, this feels legitimate.And I think that’s a, what I would call, you know, closing the credibility gap, you know, really, that first impression is so important. So we really kinda overdid the initial MVP. 00:12:06 Nathan:Yeah. I think that design is one of those things where you can go a long ways. And it’s probably the first thing that people cut when it comes to the MPP. And that’s just, I’m like, Nope, that’s not an MVP. You have to cut features. You can’t cut like the quality of, of the design. And if I have a limited budget, I’m for sure.Spending half of it, if not more on design. So I think you made the right move there.00:12:29 Andrew:Yeah, I think, I think today, I don’t know if we’re going to go off topic here, but I think a lot of startups today can legitimately have user experience in design as their competitive advantage. Just saving people, a Couple of clicks, making things easier to use, having a product where you don’t have 50 tutorial videos, you’ve got to watch, or course you have to take. that’s a huge advantage. and there’s a lot of products that are very clunky and kind of feel like a car with, you know, like a jet ski engine added in. And I just kind of like a Jenga thing, you know, there’s just so much technical debt to the product. I think though there’s some products out there that I think could be rethought in terms of like the experience and the design they’re delivering to the customers.But that’s, that’s probably a whole nother topic.00:13:22 Nathan:Yeah. Yeah. But we agree. And anyone who’s listening to this show knows that I care deeply about design. one thing that I want to ask about and spend a lot of time on is content strategy. if I go to your website and go to the about page, it just lists your title or like your, your job description and your role as marketing. and so I’m imagining that’s where you spent the majority of your time in, from the outside. It looks like content marketing is, either a very large or the largest portion of where you spend your time and how you’re looking to grow MicroAcquire. Can you talk about how you think about content marketing and the growth of the business? 00:13:59 Andrew:Yeah, I think that was twofold. So number one, the first thing that happened to me when business apps was acquired, I had like five founder friends reach out and they said, how did you sell your business side is, is, were what, you know, so as entrepreneurs, we’re not trained to sell businesses, we’re not educated on what is due diligence, what are the legal steps of an acquisition?So I felt it was a twofold, the problem with the benefit. And when I say two folded, not right. Prom, but well point number one. Yeah. It’s a phenomenal growth channel for us. we think heavily in terms of, you know, what is the content that, entrepreneurs will need when they’re going through an acquisition, because the more we can educate them on acquisitions, the more we’ll be able to facilitate.And I think that’s been crucial, but then two there’s just no content in the market that like there’s books on fundraising, there’s books on marketing there’s books, on design there’s books on there’s a couple of books on, exits, but there just is such a disproportional amount of content available for everything, but a startup being acquired, that we felt, you know, there’s an opportunity here to kind of be almost a, I don’t want to say thought leader.00:15:20 Nathan:Yeah.00:15:21 Andrew:Kind of write the book, if you will, on, you know, this is, but also important to note is we write content for the seller, not for the buyer. we kinda think, you know, the buyers are set, you know, the buyers that we work with are, you know, private equity firms, corporate dev teams, other startups, people that, generally are sophisticated with, and also a lot of first-time buyers, but so the condoms still applies, but it gets you in the head of the entrepreneur, but we wanted to really empower the founder.So you’ll notice every piece of content is angled towards the seller, not the buyer, if that makes sense. And I felt that was critical and just something cool to do for other founders, not like, Hey, this is an article on how to get like the cheapest SaaS acquisition possible. so we read articles on how to maximize your startups exit as.00:16:14 Nathan:Yeah. I mean, that, that perspective is in your, like your founding story for the company, But then it’s interesting, like, all right, it makes sense that it carries through all of your content marketing as well, because in the same way that you have know who your customer is, which in the marketplace, you have a lot of different customers or you’re, you know, you have both sides of it, but, 00:16:32 Andrew:That’s that’s something. Yeah, you’re onto something. So that’s something that, we determined, very, very early. So when we raised our, our seed round, I hired my former VP of product, VP of engineering. My former CFO, and my former head of marketing who’s now gone. Cause he went, he was, he was, he was like one foot in he’s started this, agency called brand arrow. so if anyone needs help with, Facebook ads or just any sort of SaaS marketing shadow, Tim brown now I told him like, Hey, you got to, I’m a big fan. I need like a micro mafia at one point. So I, I told him to dive in on that, but, we did an offsite and we, defined our culture, you know, our values, but really specifically, like you said, who was our customer?Cause it could be so many people, it could be okay, buyers, but there’s so many different types of buyers. You know, which ones are we going to cater towards? And then there’s sellers, you know, there’s so many different types of sellers. There’s people looking to sell comments. Again, domains, Amazon FBA businesses, SaaS founders.And so we really narrowed in, got super specific with our buyer And that really guides a lot of the decisions that we make all the way from the content to the product. I think that’s really crucial in the early days, because you can always expand outwards. There’s a theory. I don’t know if you’ve heard of this, but the bowling ball theory, you’ve probably gone through this with your business where, you know, you start with one sorta audience and then I one customer segment, and there’s just like these natural sort of like, you know, other segments that target for us, it was like e-commerce.And then we’ve been seeing a lot of just miscellaneous. You know, profitable software companies. So now we’re a little bit more broad. So when I described my required of people, I say, it’s a marketplace. So profitable software businesses, not just SaaS anymore, but yeah, we started really specific with SaaS founders being, our initial customer,00:18:37 Nathan:Yeah. Like narrowing it on. That is always a good thing. Okay. So content strategy, I’m seeing you do a lot of different things. one at let’s just take Twitter, as a starting point. So I was looking back in August, you had 30,000 followers on Twitter. You have 73,000 followers today. You’re tweeting five to 10 times a day.Often. Like you got a lot of, a lot of posts going out. It seems like they’re resonating, obviously from the growth and all of that. you have a lot of these single posts are like single sentence. You know, here’s an idea latch onto it, like positioning type things. So like one, one example is, instead of thinking of a hundred plus startup ideas, pick a customer you’d love to serve and solve their problems.That gets a thousand likes, 150 retweets or more. I want to know, two things, one, tell me about your Twitter strategy of how it fits into the broader business and what you’re trying to do there. And then two, we’ll just get into what’s working. What’s not working. 00:19:33 Andrew:Yeah, definitely. So Twitter strategy, there is absolutely none, aside from having fun. And I’m a firm believer of this, I think when people try to have a social media strategy where their goal is to grow followers. And so you start doing stuff like looking at other people’s tweets, and then you take a tweet and this how I see this all the time with some content I put out like, oh, that looks very familiar, but I don’t, I don’t, you know, I don’t care. but they’re trying to grow their audience and they’re not being authentic to who they are. And they’re trying to be, you know, they’re trying to, I guess what I’m trying to say is, Find a way to utilize, you know, social platforms in a way that you enjoy. So, one thing notice if you look at all my tweets, they’re all from my iPhone.Like they’re not from my web app. They’re not from a scheduled Twitter thing. I just like that tweet. I remember writing that tweet. I was like, in my kitchen, I was just like, did it, you’ll also see a tweet right before this podcast. That’s just me. I was waiting for you to come on this podcast. I was like, so I think my point being, and I think this goes even broader is just, you know, if you want to be great at anything, and I’m not saying in any way, shape or form, I’ve created Twitter, but you just have to enjoy it.And then if you enjoy it, you’re consistent at it. And then, I do have a few rules though. I don’t usually comment on people’s cause like you know, once you start getting to a certain point on Twitter, people, you can just post like Entrepreneurship is awesome. And then people have like a hundred questions and I just don’t have the bandwidth to answer all those questions.So I usually will, I’m watching those questions and I’ll usually, if some, if something’s interesting, I’ll, use that as a new tweet. and then you get tweeted out a lot, like, Hey, follow me. Like, Hey, we’d be on my podcast. So I kind of have a rule of like stay in my lane, if that makes sense. I’ve done a little bit of like beef marketing and stuff like that, you know, I’m sure you saw me like call out like tech, Raj, or maybe like throw a couple of shots at like, just joking, like VC sort of like, you know, shit posting type stuff. And that works. It definitely works. And there’s some strategy behind that. That’s probably one part of my social media strategy that was, strategic, it’s effective, but it’s not for the faint of heart. cause you do you make people pick sides, so you’re going to upset some people and you’re going to make some people really cheer you on.And so, I’m kind of done with that phase. that was fun. 00:22:20 Nathan:So if someone is in that phase or they’re thinking about it, right. They, have a specific audience for their business or like a specific focus. They’ve chosen a niche and they have some strong opinions and they’re not that kind of person who’s like, you know, like let’s not cause any conflict.They’re like, no, I’m actually, I’d be, I’d be willing to get into a little bit of conflict. what would you say what’s, what’s your advice on going down that path of like, if you’re thinking of oh, there’s a TechCrunch in your space or someone else that you might want to pick a fight with? 00:22:49 Andrew:Did you just gotta really believe it? like, and I think it has to be factual, like what I said about, TechCrunch, as an example, just go on their website right now and see it. And tell me if you can find an article about a bootstrap startup. like, that’s all I said is like, you guys are a publication that writes about just venture backed businesses. and you know, what kind of really struck a chord with me with that was my prior company business apps. You know, we were in TechCrunch, all the time. Like they loved writing about, you know, real business building storage partnerships, you know, version 2.0 launches, you know, international exp like, you know, stories that inspire entrepreneurs.And they moved towards, you know, this really venture backed sorta, you know, you’re, you’re either in it, or you’re not in it. And I just blindly called them out on time and then some people. were like, yeah. And then I was like, huh, maybe there’s something here. And then I just, and this is how I always think of or how I validate ideas as well as, so I have a publication now called, bootstrappers.com, which is just kind of like my.Like what I wanted, like just, you know, I want inspiring stories, like back in like 2010, you would read articles on TechCrunch about like, two people. They just launched a product, no funding. I remember some of the writers I used to work with, are they all left? They’re all gone. It’s like a new, it’s a new company.It’s, it’s been acquired by four different companies. And you know, some of the older writers you’re out, but, the older crew, would kind of joke and say, Hey, BC’s like, I hope you banked me one day for writing about all the companies that I discovered. and then you find it later. now the opposite is entirely true. And so I, I wanted to bring that style. You know, journalism back where it’s stories about companies making like 200,000 a year or 500,000 or 2 million. because you know what, I read an article about a company raising 200 million and then 500 million, like the next week. it doesn’t really inspire me too much.And I think that celebrated so much today and, you know, the startup community that I think it’s a little dangerous, I think, as a young entrepreneur, like if you think the path to being a successful founder is. Get into Y Combinator, raise a bunch of funding, get featured in, you know, these magazines, because that’s what happens when you get fun.That’s like the only way to get covered sometimes, is funding announcements. and even then it’s hard cause there’s so many. so I think that creates an environment where a lot of entrepreneurs are focused on raising capital rather than raising or generating revenue from customers.And that was just something that I lived through.I had a really good mentor. We’re told, are we going off topic too far?00:26:04 Nathan:Well, I do want to take you back to, like the idea of like picking a fight. But finish the thought with a mentor. Who’s everyone, everyone listening knows that ConvertKit is bootstrapped. I’m a huge fan of that and the same things, the same reason that you’re picking a fight with TechCrunch or that you did, I would do the same because we experienced that, you know, we could have more revenue, more customers, all of that than, anyone else, but they’re only going to write about the VC funded version.So, 00:26:28 Andrew:Yeah. So so long story, short business apps, my company prior, boot shove that business, and I just had a really good mentor Christian free Freeland. And he was always challenging me to think against the difficult soak on early pap. And we were based in San Francisco for five years, eventually moved to San Diego and that’s where we exited the business. but, yeah, now that like I’m on my third, I took a little hiatus and went into crypto land for a little bit. So it got away from like SaaS and stuff like that, but now I’m back home. and yeah, just saw that and said, okay, and then actually TechCrunch did write a little bit about bootstrapping and then I’ve also seen a lot of other people start saying the same thing, like agreeing, which I think has been cool.It, which isn’t like it’s not a bad thing that TechCrunch or any publication, I don’t want to just hone in on, on TechCrunch. because th they’re, they’ve done so much for so many founders. but yeah, other people, I feel like the first shot was fired. Like, Hey, You know, we miss the old version of, you know, maybe mix it up a little bit.And they’ve taken some of that feedback and I’ve actually written about some bootstrap companies and then other people have kind of said the same thing. Like, you know, the startup ecosystem is really turning into this, you know, fundraise craze news cycle. And, you know, there’s 99% of other startups that aren’t going down that path.So that creates kind of like a movement. So that was like the benefit of, of beef marketing sometimes is you, again, make people pick sides. Some people agree with it, some people don’t. yeah. So advice for anyone in terms of beef marketing, I, I, again, I, going back to my original point, it how you have to believe it, you have to believe what you’re saying.It can’t just be like, you know, one foot in, from my perspective, Most of the major tech publication should write about, you know, businesses that are profitable and sustainable and ones that are raising a bunch of capital and going public like a good mix would be amazing because then that gives you a true picture of, you know, all the different styles of entrepreneurship, you know, the ones that are at the top of the top and the ones that are taking a more sustainable practical approach, just giving a more realistic view into the world of entrepreneurship instead of just kind of, you know, putting this one style on a pedestal.Yeah, I mean, just get ready for, I mean, nothing bad happened. so I would just say also with beef marketing, it doesn’t have to be just, an individual Oregon or, or an organization. Like good examples. So I’ve always had a, like, kind of an, a branding, an enemy, and all my businesses for business apps.It was a large businesses. Like our main sales pitch was, you know, Starbucks down the street, paid 2 million for their, mobile app, blah, blah, blah. You know, would you like to create that same customer experience for your customers and, you know, like David versus Goliath type story, you know, Mike group, we’re kind of fighting for the founders.Then all the other stuff that I just talked about, but Salesforce had, their, their enemy was on-premise software. They essentially invented SaaS, you know, the company. Say a little chat thing. Yeah. They had a big campaign of just no forums. Like no one wants to download an ebook anymore, like forms go away, please. and I thought that was very clever, box.com had some beef with Microsoft, which was definitely fun to watch. I’ve I’ve been around long enough where I remember seeing in San Francisco, like, the billboard of like box, just basically saying Microsoft sucks. you know, Uber and Lyft were throne, had a food fight for awhile.That one probably went over over the line maybe. but yeah, my point is, is there’s other examples it could be, for your business, it could be expensive. To like, I don’t know, like it could be, it doesn’t have to necessarily be like a organization or it definitely shouldn’t be a person either.Like don’t ever like just straight up call. That’s just, that’s not cool. Like if you have a problem with a person, call them and tell them your problems, like, that’s it now. Like that’s not, I don’t, I don’t support that at all. I think that’s ticky-tacky and just a sign of just weak character, if you’re just literally, you know, trying to tear someone down for your business’s benefit,00:31:28 Nathan:One thing that’s interesting, I think is you probably watch some, maybe beefs between individuals is just how many of them, maybe are planned or facilitated in some way. that is interesting. Like someone, messaged me today because, sort of like Nick Huber who’s, has a popular Twitter profile under sway startup.Hopefully we’ll have him on the show soon. He was, he posted something like controversial, which I know is one of his top of funnel tweets, right. To try to get as much attention. And so I purposely like aggressively disagreed with it, you know And then we’re just separately texting, like, Oh, thanks for the engagement, you know Right. Because we know that by deceit, like if he strongly takes one stance and I strongly take the other stance, then like one, no one will think we’re actually mad at each other, but then too, like, it’ll get a lot more attention engagement. So a lot of people are doing. Some version of that. or if you see a happening usually between two individuals often, they’re probably on really good terms behind the scenes. 00:32:26 Andrew:Yeah, I did not know that that’s, that’s me staying in my lane. I, I, I missed it. but yeah. I, mean that’s business entertainment, you know, there’s, there’s nothing wrong with that, but I, think there’s a line to be drawn, you know, like, If you do engage and stuff like that. number one, I think it’s always great when, like, if it’s real and then they like, like, Hey, we’re cool now.Like, you know, we did this in pub and now like, okay, we’re on 00:32:59 Nathan:Close that loop. 00:33:00 Andrew:Yeah. I think, I think that’s really cool to see. but yeah, public food fights, not my thing. don’t have appetite for that or any advice, but I will say, I will say Nick is coming hard on some, some of the stuff I’ve said, like, 00:33:16 Nathan:Whole angle. 00:33:17 Andrew:Yeah.The, the one thing I’ll say about that though, that style like shit posting, you know, I was like some view of like VC funds just based on like shit posting and stuff like that. what I’ve noticed, ‘cause this, this actually, this is probably a good tidbit for, you know, if you’re considering, beef marketing and what happens is you draw in a type of crowd that likes that negativity and it, and that can drain on you.And so if you should ship posts all the time, like a large amount of your followers are just going to be shipped posters, and they’re going to be, then all your comments are like, use a blah, blah, blah. I mean, if you go on Nick’s feed, you can just kind of look, just look at his comments. He has like a million people.Unfortunately insult, I kind of feel bad for him sometimes because I’ve also seen him comment how it affects him personally. I, I don’t know him, so maybe it doesn’t give a shit, but, that’s why, again, I say, stay in my lane. Just keep it positive. Aye. Aye. Microfibers entire marketing strategy is literally just inspire or support encourage entrepreneurs.It did. not, I mean, not getting beefs with people and stuff like that.00:34:33 Nathan:Have you. like, there’s the side that you’re, you’re taking of, using your personal brand for marketing, you know, growing a Twitter audience, all of that. You’re very off the cuff of like, you know, just firing off, tweets or things that you, you think about. But at the same time, like you’re a professional marketer and you tend to, from my new at you and other places, like you’re very methodical, you tend to attract things really well.Do you track efforts that go into Twitter and Like how that translates into, you know, deals on MicroAcquire or new buyers or sellers, you know, like listing listing companies or any of that. 00:35:10 Andrew:So I’m a big believer in, so David can sell from drift said this really well where, I think I might’ve mentioned this to you the last time we talked, but, he, he broke it down into like three phases where, we’ve gone through three phases of SaaS. Like the first phase was invention murder. The first person to kind of build a tool one, the market.And then the second phase was the first company to really figure out the best, go to market strategy, like LTV to CAC, you know, AEs STR ratio who could, who could land grab the market fast enough. And then right now he says, he calls what we’re in today, the Procter and gamble phase, which is your brand. So it’s most defensible part about, your business is your brand. Your technology can be copied. it’s easier than ever to raise capital to build a team to do that. There’s also other things like your culture and your team’s talent and just, you know, again, your unique insights into the market. People can copy chapter one, but not chapters two and three and four that you have planned. so I think a lot about that, a lot in terms of just brand and market reputation. But So, no, we don’t, I don’t measure it. when a tweet goes viral, like the one you just mentioned, I don’t look at the comments because when a tweak gets like a thousand likes00:36:33 Nathan:Yeah,00:36:34 Andrew:Is gosh, like the questions and the people like disagree with you and just, you know, you start to enter, it’s like, you’re in a stadium of, you know, 200,000 people are reading this and then like 200 people have comments, not everyone’s going to be like, yeah.Like half of them are going to be like negative stuff. So, yeah. So I, I push, I push away all negative energy. So if, if it’s not positive, I’m over it. 00:37:05 Nathan:W what you’re describing is interesting of the city of idea of, if you think about it, like maybe your immediate group of friends, you post something, the people who reply right away, you interacted with them a bunch, like that’s who’s on the field or whatever. And then the next group is like the coaches, the diehard fans, like the re the support staff, everyone else, like those are your Followers. And then you can tell every time that this tweet goes beyond that, because you start to get, like, I had one on company culture that, was like a thousand retweets and went really far. and you could just immediately tell when it had gone to like two levels beyond the people who follow me, cause it just, it went totally off the rails. And you’re right. That the only thing you can do is like mute your own thread and move on. 00:37:50 Andrew:Yeah, I just, and you could tell, cause I usually will like everyone’s tweets just cause I respect everyone’s opinions, like bringing, Nick back up. He, I remember I had a tweet, just something about how entrepreneurs that have maybe struggled in their childhood, have an advantage. He came in with like a strong disagreement and kinda, but I respected it.But then I, we, we kind of close the loop with like, Hey Mike, I think you’re taking this out of context. so I’ll respect everyone’s opinion, but once it goes, you know, I’ll like all of, them. And then once it goes viral, that’s when it’s like all, everything is just nuts. Like, you know, I can’t, I would never want, I can’t keep up with it.And then too, I’ve probably already moved on to like three or four other tweets that, you know, I’m thinking of or something like that, but I think, I think that’s another important side of, just social media in general is just understanding like everyone has a right to their opinions. So even if people do strongly like disagree, that’s awesome.You know, everyone is entitled to their opinion. Everyone has, You know, unique view of life And how things work. and I respect all those opinions, but I think one. thing about social media that can get kind of crazy is when you’re taken out of context, I’ve had that happen a couple of times. Like the one time with Nick, maybe, he took it as I think like, people with really great families, you know, like divorced dads make less than married men. and I, was like Nick, no, this isn’t about diverse families. It’s just about like entrepreneurs struggling with when they grew up. Like I were Joe, and then I had another one. This one was, this is a crazy one. I had one, I tweeted out. Hire people you’d be friends with. And that was, literally someone literally took that as far as saying, nice job describing why tech is sexist and racist in five words.And I, and I was like, what? And I was hanging out with my sons. I didn’t have like enough, I didn’t catch it in time. And so I come back, to my phone and I had to delete the tweet. And then I actually, you know, put more con like, Hey, I meant that as like, you know, hire people, you’d be friends with and you’d care for them personally and professionally, not just hire a bunch of white people or something like that.Like what? So sometimes you gotta be careful, when that kind of stuff goes down. And it’s also just fascinating how people can, again, their, their perspectives, like their perspectives and their viewpoints. you know, you can say one thing and it means one thing to you and something completely different to someone 00:40:47 Nathan:Right.Yeah. I remember a time that Josh Pigford, for bare metrics, had a tweet about concerns in your, in a resume when someone, you know, has had 10 roles in 10 years or kind of thing, or like jumped between roles every 12 months. And that, I I’m not even fully sure why, but, but that one, like he got jumped on in a very similar way of people taking out of context and saying like, this is what’s wrong with technology and 00:41:14 Andrew:Let’s talk about that for a second. So when you’re, when you’re taken out of context, Just admit it, just say, Hey, that, that this is not what I meant. And then I recommend is deleted tweet, and just clarifying, just like, Hey, I wrote a tweet, this, this is what I actually did. I deleted the tweet. And then I said, Hey, I had a tweet taken out of context and it’s obviously a little embarrassing, you know, but it’s the right thing to do is like, Hey, like that’s not what I meant.So also admitting, you know, that’s not what you meant, but clarifying when people like, that’s not that that was not my intention of those five words in any way, shape or form, even like, that, that, that experience was so far off. I still kind of scratch my head on it. But my point being is, you know, it, you know, take one back, like, Hey, listen, I, I said something, it was taken out of context.I apologize. this is what I really meant for further clarification. And it’ll just make your life a lot easier instead of trying, to defend, because I know the thing is if Mrs. Also I don’t really comment too much on social media. Number one, it’s just exhausting because you can have so many, then you’re like a, full-time like customers support person on Twitter. again, you know, once You kind of engage with someone who vehemently disagrees with what you’re saying, or has taken you out of context, it’s really hard to change their opinion, if not impossible. So even trying, once you, if you just try you lose. You just start throwing food and stuff like that.So that’s just kinda some of the crazy stuff I’ve seen happen on, on Twitter as, you know, gone a little bit more active. cause I, I wasn’t active on Twitter, so all this is like new to me too. I’m still learning like, oh shit posers. I didn’t, I didn’t know those existed or like, oh wow. You can get really taken out of context and it can go viral and people can say some mean things.So yeah, my, again, going back to just saying I stay in my lane and just talk about stuff that I liked it. Talk about.00:43:35 Nathan:I like it. something else that you’ve done that I hadn’t seen other people to do before, but I get it as a strategy. so separate from like just sort of specific, but it’s using cameo and using spokespeople on cameo. for your business specifically, you got Chris, demon topless from Silicon valley and all of that to do announcement videos for partnerships and one they’re amazing. but like w where did that come from? And, how’d that turn into something that like, And, now if someone says like tres commas, like in relation to micro choir, everyone’s like, oh yeah, that makes sense. 00:44:15 Andrew:So for the longest time, it was just me running Mike requir. I was a solo founder. and on the team page, we just like, as I was working on the design with, I initially use an agency to help with, the development. And, there was a team page and I was like, ah, just put Richard Hendrix, Gavin Belson, and Jen yang from Silicon valley.And it just kinda was, I just thought it was cool. And some people like, you know, called it out and was like, are these really your team members? And I’m like, yeah, they were super harder recruit. So I’m, I’m a huge fan of the show because it is shockingly accurate and just hilarious. and then, yeah, so I actually, you know, before, like right when I launched my crew choir, I.When on cameo saw Russ Hanneman Chris. I can’t pronounce his last name off the top of my head, but, you know, he was available and he was like my favorite character. And I was like, yeah. W do you want to talk about my group choir? And since then we built, you know, a pretty good relationship in terms of, you know, just working with them.And he’s a really great guy. Like he’s a really, really, really nice person. but my point here is I’m always thinking about what’s, I’m always learning and I’m always trying to think of what is changing in marketing today? For example, the marketing playbooks that worked five years ago don’t work as effectively today because everyone adopts them and starts using them.And then it starts to, feel like marketing and the best marketing doesn’t feel like marketing it’s entertaining, or it, captures your attention in a way where you go, whoa, I haven’t seen that before. So I’m always trying to think of unique ways to, capture or actually I should say, earn audience attention rather than buy it, or, you know, writes an ebook and engaged it and get your email and then send you 30 trip emails, which worked fantastically a decade ago, which killed a decade ago.But So that’s kind of where the thought process and then candidly. I would say, I might laugh the hardest out of those videos. So it’s like my like guilty, like pleasure. cause you know, they’re not free. So like, you know, I, I probably am lapping the hardest, like when those go out.00:46:46 Nathan:I’ve I’ve laughed pretty hard at a lot of them, especially as like, they end up in a series where they like build on each other. The, he uses jokes that he first coined and, you know, first video. And,00:46:58 Andrew:Yeah. a little background on that too is, I didn’t tell him to make up anything like he’s made of like gas Decky style, micro Gaz, micro, and like, I don’t tell, I just basically, cause you’re only able to write in like two sentences and he he’s just a hilarious person. So any startup looking to, you know, announce something, I highly recommend checking it. 00:47:21 Nathan:I guess how has the business side of it work? Right? Cause if you go on, on his page in particular, it says $349 for personal use or 909 plus for business use, which makes sense that there would be a split there because you’ve obviously gotten a lot of earned, earned, attention from those. how does it work actually on the payment side? 00:47:41 Andrew:In terms of like using Kamya.00:47:44 Nathan:Yeah. Using cameo, maybe using Russ specifically. Well, Chris, not Russ. But using him specifically or, you know what you’ve done, you’ve done with, other people on cameo. 00:47:56 Andrew:Yeah. So he’s kind of the only we did a partnership with Clearco and I had like the game, the rapper, duke came here just because I kind of went on like a cameo binge, like I’ve been a fan of you forever.00:48:12 Nathan:Cards on file. You know, you’re just like00:48:15 Andrew:Yeah. I was like, I’d love for you to just say micro choir. Like this is awesome. who else did we get?I can’t remember off the top of my head, but, what’s been interesting to see what Chris is. when I first booked him, he was $200. Now he’s 5,000. So he, has definitely, you know, made some waves in the startup community. And So it’s, it’s cool to see him like, you know, making people laugh and helping startups get exposure and then raising his prices too, which is, I think something that, you know, most startups should do.So he’s done a very good job of that. It, it went from like one K to two K to three K. Now it’s at like, 5k, so he’s expensive. 00:49:00 Nathan:So that’s like when we see something like that, right. If the nine and nine plus, in the buying process, then later, does it tell you like, oh, here’s like once you fill out, the initial form, it’ll tell you what, what the price is or how’s that work?00:49:13 Andrew:So there’s, there’s a personal use. So you can use his personal, I don’t know his like personal cost, but let’s say it’s like 500 bucks and that would be for like a birthday wish or something like that, which can be a great way to motivate like your team, like, Hey team, great. You know, Q1 or Q4 that’s ending, here’s our goals for next year, you know, made, they want to me to give you all shout out, that’d be 500 bucks, but then a business use where you posted, externally, so on Twitter or social media, or, within some sort of piece of marketing content.The price for that is usually 10 X, you know, internal use. 00:49:55 Nathan:Did any of the other ones that you tried? Did you feel like they got attention or that kind of thing make you want to do it again? Or was it more just the ones with Chris that really resonated. 00:50:04 Andrew:I think probably you’ll see less cameos, out of me, I think, you know? there, there, there gets to a point and we could, we could probably have another podcast about this, about like things with diminishing returns. And I think I’ve kind of, you know, used them so many times that, I mean, for the really big like, announcements that we have coming up, like maybe twice next year or something like, that but I think there’s sort of a diminishing return, especially with the cost, you know? I think building in public kind of falls into that category a little bit. audience exhaustion in terms of like paid ad campaigns. you know, so I’m always thinking of that stuff too.I like, are we overdoing it? cause then it just kinda starts to get corny is when you’re doing it over and over and over and over. and it’s not really like, whoa, he’s here. Like I didn’t expect this. And when it starts to become expected, I think if there was just kind of a little bit of luster. 00:51:05 Nathan:Yeah. That makes a lot of sense. something else that you do a ton of is partnerships, whether it’s with PYP or angel list or whoever, it feels like micro choirs coming out with a partnership. Every, I don’t know what the actual cadences, I feel like it’s every two weeks to a month. what’s the, what’s the strategy there. And is that like a very deliberate, marketing strategy or is it just like, look, this is a natural fit. And so we’re just going to do a better job. It made sense to do the partnership and we’re just going to do a better job promoting it than most people do. And when they come out with a partnership, 00:51:35 Andrew:Yeah. I mean, so the pipe Clearco Angeles partnerships all made total sense. They help startups get acquired, which is, you know, the purpose of our business. And, you know, our, our main metric of success is helping startups get acquired. So helping them get financed, increases the buyer pool, which then can lead to more acquisitions.So there’s, those made a ton of sense. and then we also want to expand internationally. So we partnered with, essentially like the angel list of, Africa that serves 40 countries in Africa. And so I thought that was a really fun partnership in terms of, you know, helping, really underserved. areas of the world, or support underserved areas of the world with my group who are in terms of, you know, just our message and just our encouragement and we’re going to continue those.So we’re looking, actively speaking with, individuals that are, you know, accelerators or like, start a boot camps and like Turkey or Europe or the UK or Australia. I have a number of conversations, but we’ll probably go a little lighter on those because I also feel like the partnership thing is it’s like, okay, another part is another partnership might require really. but that’s, I think partnerships are, what I would call a non-linear growth strategy. So it’s basically, you know, what you’re doing is you’re leveraging, you know, number one, Another company’s brand So you’re, you’re borrowing some of their brand equity saying like, Hey, we’re partnering. So their capabilities are now part of our capabilities and vice versa. so there’s benefits on both sides. And then you know, with products that, you know, pipe clear co and Angeles offers specifically, it adds value to our product. So it’s like a win, win, win. It’s a, it’s a good marketing play, good brand play. And then it’s good. Just, you know, product play without, a lot of, you know, engineering needed. 00:53:41 Nathan:Is there, like, do you have engineers internally just devoted to, you know, these integrations or, or did they tend to be more on the marketing? you know, our business ops side rather than on the product side, because then they can be expensive on the product side.00:53:55 Andrew:Yeah, they definitely can. I would say they’re more. On the marketing side then on, like for example, the angel is partnership is just a landing page that so Avaloq, the CEO of Angeles is an investor in might require and then evolve in an investor in my rewire. And so I just asked, I pointed out this other company that was making an SPV product for private equity firms.And I just said, can you make me a landing page? I’ll promote it. And so inside my group where there’s like a drop down that says raise bonds, and then it takes you to a landing page. So minimal product integration there, but it’s just kind of like us saying, Hey, if you, if you’re looking to raise funds, this is where we recommend you doing it.We’ve done that with mercury bank as well, which is just, again, you know, you acquire a company, you probably want to transfer those assets and do a new entity. That new entity is going to need a bank account. So we’re just kind of getting all the re they’re almost like perks. If you will.00:54:54 Nathan:Yeah. That makes sense. And then it’s not this big integration that you’re having to maintain for years to come or.00:55:01 Andrew:Yeah, no, it’s not like a, like a Facebook, like a, you know, SSO log-in or something like that. you know, it’s a, it’s a lot simpler. It’s usually just like a lane kicking over to a landing page, you know, driving traffic to them and then we get some sort of kickback for whatever business we drive to them.00:55:20 Nathan:Is there anything in particular that’s worked well on, like the partnerships that have been a, a, huge boost, right? Where either you’ve gotten a bunch more attention for Mike require built the brand. Like, are there things that you see in common on those ones where you’re like, yes, that was a home run versus the ones where you’re like, I think that was worth the time to put together.Maybe 00:55:40 Andrew:Yeah. I mean, I’d say, I’d say all of them, I’d say my favorite are definitely the Clearco and pipe partnerships. like. Hers is he, oh, he bought me this to kick off our partnership. It’s assigned Mike Tyson glove and we’ve done a number of acquisitions together. I think their company’s fantastic. I love working with our team.Clearco same thing. So pipe, I was finance all of our SaaS deals exclusively, and then Clearco all of our e-commerce deals exclusively and they’re just great teams and it’s a clear need. You know, some people want to finance these with, these companies and we make it extremely seamless to connect to those companies.And we even do like pre-financing. So if you’re a founder looking to sell on Mike required and you want to give a line of, you know, potential financing in advance to a buyer, we can, pre-approve a seller. So it just makes kind of the, you know, when you’re going to buy a home, it’s like it’s pre finance or something.I don’t know if that’s a good analogy, but, those are, those are partnerships that really add, like they were on the product roadmap and they just, you know, we just went to the best ones in the market with the most credibility, with the largest capital pools. but also with the engineering resources.So, you know, anytime a company is, you know, financed through pipe, we get a notification within slack. It says like, Hey, add preapproval number to this company. So we just, we, instead of working with like a ton of different financing partners, we just pick the best ones and then then integrated deeply with them.00:57:23 Nathan:That makes sense. One of the things that I wanted to ask about before we wrap up is, on the sort of the investor influencer side, you have a lot of people, like know, you mentioned Deval and, and others who, have invested in MicroAcquire. And is that, helping of like helping you you know, amplify some of these things on Twitter amplify, these partnerships, open doors in some way.Do you think you get something similar with like a influencer program or has the investor side really been a good, good angle for that? 00:57:54 Andrew:Yeah, that’s a good question. So yes, there’s definitely the group of investors that my career has is like all my, like idols, like, you know, founders of companies that, you know, I like, you know, Dharmesh from HubSpot, Neval like, From Angeles, like those are some of my favorite companies and I get to, interact with them on a, on a very limited basis. I don’t reach out to them for advice, very often. So I think that also adds to just, you know, brand equity of just, being a marketplace, you know, and us wanting to build this with the startup community. That was kind of more of the thought process behind it. But now, I mean, you could even look at my likes.I, I ha I, was, has evolved over, liked something of, mine now has Dharmesh maybe once, like, so now I don’t rely on them for like social media support or anything like that. but it, it is, a good way in terms of, you know, when you raise your entreprenuers, you get kind of, again, unique insights because most of them have been through MNA. so, so typical VCs, but, I, I really liked that, style of, of fundraising is when, obviously I’m a bigger advocate of bootstrapping because that’s kind of, you know, where I’ve spent, or had the most success. But if you’re gonna raise capital, I, I recommend entrepreneurs for us because they have experienced building a business.And then typically with, you know, acquisitions specifically in my case, which is you know, extremely helpful. 00:59:33 Nathan:Yeah, you and I are both known for bootstrapping. And we’re also, I think, pretty well known for not being that dogmatic about it, of being like, here’s what we did. Here’s why it works well. Here’s why the other path can be fine too. you know, rather than being super dogmatic in one camp or the00:59:49 Andrew:Yeah. That’s one thing I’ve noticed since being vocal about bootstrapping that I think is a little toxic; if you’re funded, it’s like, I hate you. Then, if your bootstrapped, venture capital’s just a tool. If you know how to use the tool correctly, it can be a great accelerant to your business. Everything comes with a cost. So, when you bootstrap, you have to kind of eat glass for much longer. I’ve lived that life, but at the end, the rewards can be epic.So, if your goal is to make money, you should probably bootstrap, because you can sell the business whenever You want. You have no approvals. You own the whole thing. Nathan, if you wanted to sell your business, you don’t have any investment or approvals, or anyone saying, “No, you need to hit that billion dollar mark.” If you want to really disrupt the market, or change a market or, go a little bit bigger, faster, venture capital is just a tool to accelerate that. It all comes with a cost.The cost of bootstrapping is, sometimes you have to do customer support for longer. You have to do some of these roles where you can’t bring in talent earlier. The cost of venture capital is, you give it back equity and control within your business. There’s usually controls. You need approval to raise capital. You need approval to sell your business.So, everything comes with a cost, and it has pros and cons. I think bootstrapping makes sense for 99% of entrepreneurs, because the bar today is building a billion dollar business, and that’s not easy to do. So, for many first-time founders, I’m a big fan of stair-stepping and entrepreneurship. One of my favorite tweets that I’ve ever written is, “Start with an agency, get to cashflow positive, and then bootstrap an asset—whether that’s a SaaS company or your e-commerce business—sell that asset, become financially secure, and then do whatever you want.” Swing for the fences, go on a beach, whatever. Along the way, you prepare yourself for the next stage of business.01:02:24 Nathan:Yeah, I completely agree with that. I have an article titled “The Ladders of Wealth Creation” that touches on the similar idea of using the skills from one ladder to move up to the next, and go from there.Well this has been fun. I always enjoy watching the partnerships, what you’re doing on Twitter, and everywhere else.I think that MicroAcquire is a great example of what you can build with an audience. Thanks for coming on and hanging out with me and, and we’ll have to talk soon.01:02:52 Andrew:Yeah, Nathan, thanks for having me, man. I enjoyed the chat.01:02:55 Nathan:Alright. Catch you later.01:02:56 Andrew:See you, man.

Sherrell Dorsey is the founder and CEO of The Plug, a publication and community for news, insights and analysis on trends in Black innovation. The Plug features stories that show the substantive ways Black people engage with the innovation economy, including analyses of modern technologies.On today’s show, Sherrell shares about building an audience and growing The Plug. We talk about sponsorships, The Plug’s revenue model, and her background in journalism and how she brings that into her current work. We also talk about choosing a niche, staying consistent, and much more.Sherrell has worked in marketing and consulting for companies such as Uber, Tresata, MarketSource, and Build The Good. Sherrell has also worked as a correspondent for Fast Company, Essence, Next City, and Black Enterprise. She earned her master’s degree in data journalism from Columbia University.In this episode, you’ll learn: How to grow your subscribers when first starting out Different strategies for monetizing your newsletter The right way to include advertising in your newsletter Tradeoffs between having a team and working as a solopreneur Links & Resources Clay Hebert Monica Melton Farnam Street Shane Parrish Ryan Holiday Daily Stoic James clear Uber Google Fiber Microsoft Fast Company The Root Black Enterprise GoDaddy theSkimm Signal Bloomberg Terminal Business Insider The Moguldom Nation Sherrell Dorsey’s Links Follow Sherrell on Twitter The Plug The Plug newsletter HBCU newsletter TPinsights.com Episode Transcript00:00:00 Sherrell:I think that we’ve gotten into this very fast pace, and this idea of constant information and voices in your head. I don’t know that more information is making us a better society. I think that this idea of community and grappling with ideas, calling things out or bringing things to attention, but having something meaningful to say really outweighs just being visible all of the time. 00:00:31 Nathan:My guest today is Sherrell Dorsey. Sherrell is the founder of The Plug, which is a newsletter, and really a publication at this point, about the black tech ecosystems and all the interesting things that black and brown founders are doing in technology and business. She started in 2016, and she’s built it up to have a full-time team of five people now.I’m so impressed with what she’s built. We get into talking about sponsorships, the revenue model, how she built the audience, her background in journalism, and how she brings that into what she’s doing now. I actually grew up in tech and some of the ecosystems that she was a part of that inspired her.We talk about choosing a niche and staying focussed there. We talk about consistency. There’s really a lot of things in this episode. I love what she’s doing and how she’s built this niche business into something that now employs full-time journalists. At a time when a lot of other publications are dwindling, she’s growing.So, let’s dive into the episode.Sherrell, welcome to the show.00:01:35 Sherrell:Thank you so much for having me.00:01:37 Nathan:I actually want to start talking about experimentation. We’re going to jump around a little bit. You like to run a lot of experiments, and you’ve taken an approach on experimentation where you’re doing it at a stage in the business where you have a lot going on. A lot is working. This is a point where I see a lot of content creators freak out and stop experimenting because they’re like, “This is what my audience likes. I have to show up in exactly this way.”So, they don’t experiment. Even at this level of success, you’re like, “No, experimentation is a core part of what we’re doing.”Could you talk about that, and some of the experiments that you run, and then your mindset around it?00:02:12 Sherrell:We’re constantly challenging ourselves as a team, and trying not to get bored. Part of our experimentation may have more to do with the attention deficit issues that we have as a team, as a collective. Maybe not as much as our audience, but we also assume that they also have attention issues.Let’s be honest, there’s so much competing for our audience’s attention, right? I mean, outside of the inbox, theres social media, there’s the day-to-day of all the crazy, all the push notifications. So, for us, experimentation really is at the core of challenging ourselves to face something new and interesting, and really tapping into what.The sort of timeliness of news, and really finding a way to put it into our voice and share some of our opinions as well. Even with running The Plug’s weekly briefing experimentation is really even just how I got started. The Plug for me was an experiment. I was getting up at 5:00 AM, pulling together a newsletter, wanting to cover diverse voices in tech.Doing it just as this labor of love, and also nerdiness and curiosity, and it started to grow. Then I said, well, maybe I can do this every single day. Then I did it every day. Then at some point we realized, hmm, are people having inbox fatigue? What if we slow things down and really make people cherish every single sentence that we’re writing in our newsletters, and giving them a long and deep side of slow conversations on Monday mornings as they’re starting their day.We’ve seen those questions that we’re asking kind of manifest in this idea of experimenting with just our curiosity. We’ve seen that well, I mean, honestly, Nathan, we’re getting 45% to 48% open rates on every single newsletter, and it has been pretty consistent.When we were in the daily phase, we were starting to see those open rates go down. People just didn’t even have enough time to read. So, again, we start with the question, “Well, what if, or how do we personally sort of engage with our news and with our information, and how do we create a moment of almost intimacy with our audience and our subscribers?” Where instead of just having the breadth, we can actually have the depth.00:04:40 Nathan:Yeah. I want to talk about the consistency and the schedule later in the episode, but let’s go there right now because I think a lot of people, when they’re writing their newsletter, they struggle with how often to send. And, you know, if you look at someone like Seth Godin who publishes every day and has done it for, I don’t know, decades at this point, it’s like, oh, I should be like Seth Goden and publish every single day or send out, you know, a newsletter five days a week.But one that’s incredibly hard to maintain. And then two, I think you’ll see exactly what you’re talking about. The engagement and interest drops off, too much of a good thing is still too much. What do you think about that?00:05:18 Sherrell:I think that we’ve gotten into this very fast paced. I mean, I, you know, Twitter became a thing when I was like exiting undergrad and this idea of just constant information and voices in your head. Was kind of standard and status quo. And I feel as though now we really wanted to hyper focus on how do we get people to sit with ideas and thoughts before we kind of bombard them with just more information.And I don’t know that more information is making us a better society. I think that this idea of community and grappling with ideas, you know, calling things out or bringing things to attention, but having something meaningful to say really outweighs, just being visible all of the time. I think especially with the newsletter, with the newsletter, you’re telling stories, you are bringing ideas to the forefront, you’re surfacing news and information for people to kind of ruminate on.And then we can kind of hit people later on in the week, which we do with here’s opportunities to engage further. Or did you check out this data set that we’ve pulled together that will allow you to look at. How HBCs are graduating, like the top black engineers in the country. And so for us, it’s about what is the value that we’re providing to our audience?Why, why would they want to continue to open the email instead of just, let’s be there for the sake of being there, you know? And it’s like, it’s like small talk at networking events where like people are pushing their business card on you. And you’re like, I don’t ever want to 00:06:50 Nathan:Okay 00:06:50 Sherrell:You ever again in life.And we definitely did not want to be that like pushy networker. We just wanted people to be able to sit with us, have a cup of coffee, have a tea, and just, you know, Really, really, connect with us and our work. And so, thus far, you know, like I said, we really saw our open rates increased drastically going from the daily into that weekly and it being meaningful.And our managing editor, Monica Melton, who was our first employee at The Plug has really, really ramped up subject lines and experimenting, in AB testing that has been so beneficial in terms of how the newsletter is being received.00:07:36 Nathan:Well, that’s something that you just can’t do when you’re on a daily deadline. I’m trying to rush out on that scale, or you have to have a much larger staff to be able to bring that level of thoughtfulness and testing to each piece of content.00:07:50 Sherrell:So true. So very true. I mean, you know, we’ve always sort of operated and I think most startups, you kind of have to do more with less. And I think from the standpoint of delivering higher value really wanted our team to be able to think through, well, what should that Monday newsletter say? What are the opportunities that we can really present to our audience that are thoughtful?Even during our editor, our weekly editorial call, like we, we, we really deep dive into what are some of the top issues? What do we think about it? We really get to massage it out and be thoughtful. And I don’t know, even if we had a larger team, maybe we would do more, maybe, maybe less. General newsletter, maybe more profiles would be really nice.And we’ve recently launched a new newsletter as well. it’s kind of the niche of the niche. our incredible HBCU innovation reporter recently launched an executive newsletter for those who are recruiters, HR professionals who are really trying to understand how do historically black colleges and universities play a role in the future of work and just breaking down stats, breaking down the kinds of patents that are being developed, breaking down the kind of research coming out of these institutions ways in which to engage with faculty, new entrepreneurship centers, all of these like really incredible stats that you don’t really hear on a daily basis.So that now that is a subset where now we have increased the cadence of our newsletters, but we’ve created that for a very specific niche within the niche of audience that we serve.00:09:26 Nathan:You said something about it’s almost the environment that your newsletter is received into of your app. Like telling someone slow down, this is be thoughtful. This is a thoughtful part of your morning. Like have your cup of coffee, have your tea. And I’m realizing that as a newsletter creator myself, I often don’t think about like, I’m not asking.The reader to get in a state of mind to engage with my content or get in a physical space. And so this is it’s interesting, I haven’t thought about before and it would change the approach to the content and it would for sure change the approach to the writing because instead of going okay, punchy headlines quick, this is for the busy professional, reading it on the subway, you know, like that’s one style and it sounds like you’re hitting in a completely different style, I guess.Tell me more about that. And then the other aspect of it is what are the ways that you reinforce that message to your readers? Cause it’s one thing, if you think in your editorial room and conversations, but that you have to actually translate that to the reader so that they feel it as well.00:10:31 Sherrell:Yeah, we just didn’t want to be forced to speed up. honestlyit was who I always liked this idea of, of slower journalism. I grew up such a reader like my mom and I get up on Saturday mornings and go to Barnes and noble when like bonds. And like when we actually went into bookstores, right.She would like leave me in the kids’ section. And I would just like, get a mountain of books and just sit and read. And I always think about that opportunity of like just saying. And reading and in sitting and like digesting ideas and information. And when I think about some of my favorite newsletters, I think about, the, the Farnam street blog and, and Shane Parrish, Paul Jarvis used to write an incredible newsletter.There’s just so many incredible writers and thinkers that create these kinds of long form pieces. I think, right in holiday and the daily, it does a really interesting sort of long form, you know, he does, he definitely does like the, the Daily of course, cause it’s the daily. but these kinds of newsletters that really made you think about the world around us and sort of the new ideas that are emerging and.I felt as though, as we were starting to deep dive into this Nisha space, of course we cover black and brown innovators, future of work, future of business, inclusive business ideas that are highly data-driven. You have to really sit and think about what this data means when it means within your work. And it’s not just like a flash in the pan, series or subsets of ideas.It really is how do I take this and apply it to my work and everyday capacity. So we didn’t want to just give like bullet points of actions. It was more of, you have to apply this in your world in your way. And so I wanted to kind of recreate that to an extent. and as I mentioned before, you know, experimenting with.Subject lines and titles and flow. And I mean, even just organization of information, you know, there’s always sort of the backend analytics that you can take a look at. What are people actually clicking on? What kind of things do they care about? serving our audience, a great deal to understand what they want to hear more about.I know that there are a lot of investors who subscribed to us who are always looking at our startups to watch section, and just the fact that people are able to kind of read this very long email and find a section that resonates with them and decide to take an action from that. That for us really demonstrates kind of a metric that we did not even anticipate going into this.And that really has to do with listening to our audience, quite frankly.00:13:11 Nathan:Yeah, that’s good. I have more people will take that approach. cause I think. Now you say that and noticing that trend in a lot of these newsletters, like Shane Parrish, or like James clear, some of these others that have been going for a long time and built these substantial audiences is there’s a level of intentionality that really makes it unique in that way.Let’s go back. And, now that we’ve gotten into some of the tactics and the high-level things, let’s talk about, you know, actually starting The Plug. So you started in 2016, is that00:13:39 Sherrell:I did. I started at 2016 as a labor of love. I had been writing freelance. I was working in tech, so I am an alum of Uber, as well as Google fiber, Microsoft and high school. I like worked, as an intern and like tech was always just such a big part of my life. And I grew up in Seattle. So it’s like, go figure of course, like the girl that like grew up in Seattle is like a tech person.So, so it was always a huge part of my life. And what was really cool about my experience in Seattle is that I was trained in coding and network administration and all these really cool programming language and languages from a woman who was a retired software engineer from Microsoft, who like converted a storefront.And she was like, I want to teach inner city kids like about technology because. I’m female, I’m brown, I’m gay. Like there’s not many folks like me in this space. And like, I want to create back in this space. And so my experience was just so unique. And when I got into the workforce and the conversations that were happening in media did not include voices from folks like myself or from Trish who started the center that I went to.And the folks who kind of raised me while I was at Microsoft, who were from all kinds of backgrounds and all kinds of experiences and like would burn me like, remember back in the day when you were burning, This amazing mentor who like she was like, burn me, like all of the Mo like the brand new heavies, most Def like all of these, like really amazing like albums.And, you know, at the same time, like teach me about like walking through this space of tech in a very male dominated field. And so when it come to the workforce and the media was kind of always a grandizing like all of these men and their ideas about the future, I was like, well, I’ve met some really like dope, you know, women engineers, or really dope, like black software developers and test engineers.And, I shared, you know, office spaces with, you know, incredible like female engineers from India. And I just did not see that like thought leadership component coming from these different facets of society. And I was like, well, you know, I want to start covering communities outside of these kinds of normal technical.Right. And I also was just walking through the world in living in places like New York city, living in Charlotte, North Carolina, even Bridgeport, Connecticut random. And just really finding these genius ideas and people in business leaders who were kind of unsung to a degree, but were working on really hard challenges and finding some success.So I had been kind of freelancing and, and writing for fast company, the route black enterprise and sharing these things. And I started to kind of become known as like, oh, like she’s like the black girl Tector list. Who’s like trying to cover everyone. and so at some point, you know, I got to a point where like, I really want my own column.I really want my own column. And you know, I think editors thought like, okay, your writing is okay, but it’s not like, great.And like, this space is kind of cool, but like, that’s just not what we do. And so, you know, I was like, okay, I’m going to spend my $10. I go daddy and buy my domain name. And I’m, you know, people were already calling me like The Plug, like, you know, where everything is, whoever went is, you know, what’s happening, what’s going around.And so I just started like this newsletter, I just went for broke and it was like, I’m going to create this daily newsletter. I’m going to get up at 5:00 AM every day and let’s see what happens. It wasn’t a business yet. Nathan. It was just an idea. Like, let’s see if I can kind of create an environment where we are covering, you know, innovation from the perspective of communities of color, startup leaders, VCs, and grappling with like really interesting ideas and trends.And then also sourcing storylines from around the web. So that went on for about a year and a half. but about six months in is when I got like, we got our first corporate deal and I was like, oh, you want to give me money for this? Hm. I wonder what I can do with this. and, and that really enabled me to really get started and bring on some freelancers to help support the production of the every day.And at some point we decided, you know, following grad school, like let’s, let’s go for the school throttle and see if we can really build a substantive business here.00:18:15 Nathan:So, what did it look like that first year to grow subscribers? Right? Because going from maybe let’s just talk the first three months going from buying a domain on GoDaddy to the first hundred, the first 500 subscribers. Like what was that process?00:18:31 Sherrell:Yeah. Well, first I like spammed, my friends and family was like, you better subscribe. so that was,00:18:36 Nathan:Which I highly endorsed as a strategy, like legitimately, because going from zero to a hundred is so hard. If you’re like, no, I will only do it. people who come in through major publication or like, I dunno, what 00:18:48 Sherrell:Yeah00:18:50 Nathan:Your friends.00:18:50 Sherrell:You’ve got to like breakThe rules and you just have to like go literally go for broke, you know? And so that first hundred, you know, it was really looking at the audience. I had sort of built through my reputation of covering this beat. Over the last few years, like a few years prior. And so, you know, those were people who were immediately bought in, friends and family.I asked people to push up a newsletter very frequently. I was like, shamelessly plugging The Plug and like, Hey, you know, if you like this, like share it with your friends, share it with your colleagues. it definitely was not easy. It was a, it was a kind of one by one getting people bought in. And of course I had the power of social media, you know, on my side.Whereas had I started this like years prior, like in, in, in college before Twitter became a thing or Instagram or Facebook, perhaps I wouldn’t have had as much visibility. some things that also helped to supercharge quite honestly, was like sharing across LinkedIn, just from a professional capacity standpoint.I was still freelance writing as well. So it allowed me to share, you know, Sherrell is like the creator of The Plug and you can sign up here at the bottom.00:20:02 Nathan:It changes your byline.00:20:04 Sherrell:I was able to, yeah. I was able to really leverage my, my byline. but it was a lot of pushing. It was a lot of, it was a lot of like asking people to share and to subscribe all the time.00:20:15 Nathan:Yeah. I was talking to someone, a friend who has a book coming out right now. And I asked him like, how’s it going? He was like, oh, it’s a lot of work. I’m doing a lot of begging right now. You know? And I was like, yep. That’s Write of like, Hey, will you share this? Will you, do you know anyone who could subscribe?Will you subscribe? and a lot of the people who end up like getting traction and making something are the people that are willing to do that. And then the people who are like, you know, I tried this new venture, I put it out in the world and it just didn’t resonate. And so I shut it down and moved on after three months or whatever.It’s like, you dig into their stories and they’re the ones who weren’t willing to, you know, as long text all their friends. And so it just takes that level.00:20:55 Sherrell:Absolutely. I mean, three months is hardly enough time. I mean, you almost need like a solid two to three years to really, really like solidify yourself. The right conversation, get in the right rooms, build it, that level of credibility. I know some people who are able to do it very quickly. I think you’re, you know, you’re leveraging relationships, you’re leveraging interviews and it’s nonstop.You’re nonstop promoting yourself. And you know, I’ll be honest, Nathan, there’s a bit of discomfort, in promoting yourself constantly. I think also like as a woman, I had to get very, very comfortable. I think that’s something I had to learn in tech of, you know, watching like my male counterparts, like constantly talk about how great they were.And like, I was always so uncomfortable the exact same demeanor. but I had to find my own way to talk about the work that I was doing and what I found interesting. And the more that I did that, I found that again, you know, folks were just subscribing because I asked they actually cared about what I was doing.And even to this day, We are full fledged, you know, running media company. And we have people who were literally those early subscribers who have been with us since the jump. So when we have typos or when we’ve had titles in the past, or we’ve had a glitch or an email accidentally without, I mean, these folks didn’t berate us or like drag us online, they were just like, Hey, just want you to know this link doesn’t work.And I hope you’re well, like I’ve been following you for years. Like I get those emails like every single week. And it is so incredible to really know that like, people have been rocking with you from your early days when you were less sophisticated, less refined, you know, and, but still they, they understand the intent.And they’ve seen that throughout the process of you growing your, your business, that you have been intentional. And I think that that’s the value that they find.00:23:00 Nathan:Yeah, that makes a lot of sense. what about, well, was there a point in there either three months in or two years in or something where you were wondering, is this working like, should I keep going on it or was it just steady progress without any self doubt?00:23:17 Sherrell:Wish that I was the most confident person ever. I mean, fine. Find me someone who was just like, yes. I mean, you know, maybe Elon Musk, talking that he knows that everything he does is going to turn to gold. I definitely am not one of those, those individuals. I definitely, would have moments of discouragement, you know, you know, we talked about open rates, right.And I think, you know, sort of like as you’re ramping. Your open rates look really good because your list is, is smaller. And then as your list grows, your open rates change and fluctuate. And, and if you’re not familiar with, with that, it’s really rough. You know, especially when you’re still just learning the tools, you’re still learning the techniques of AB testing or you’re learning the tools of how to really create a captivating subject line or a captivating headline overall.And so, you know, when, as we continue to grow or you see the unsubscribes, right, like unsubscribes are still deflating. Even now years later, Maven is like, oh my gosh, like, why would you leave me? You know, it’s like a breakup, you know, you’re like, why would you ever leave me? And honestly, most people just get overwhelmed.And we, what we saw was transitioning to that. Weekly versus the daily. We’ve seen significant drops in unsubscribes. You know, folks, folks have time to actually read us. They don’t feel overwhelmed with seeing our name in their inbox every single day. but there are, there are challenges for sure. You know, I think that, you know, I think that when you start to kind of compare yourself against sort of others emails or their newsletters or seeing their growth and the tactics that they’re using, and also knowing sometimes you don’t have the resources, you know, we didn’t put money into Facebook ads or any other kind of platform.Everything for us had to be organic and it had to be intentional. And without having a huge marketing budget to try to get across certain milestones. And sometimes that can be discouraging if you’re like, oh wait, like they’re lists maybe twice the size of mine and they’ve not been doing this as long.And they’ve been able to put in the resources to kind of move the needle, or, you know, even in wanting to kind of stay intentional and practice this idea of slow journalism and slow information. When you see others who are like quick flash in the pan and, and they’ve grown exponentially, but it’s also like, okay, we have some of the most engaged readers ever.You know, again, people who will show up will continue to show up to our events when we do something in person, or kind of contribute and show up to our virtual launches and things like that. And so I had to always kind of refocus on who my audience is and who has really stayed and stuck with us and the value that we deliver because the outside comparison will definitely.Kill any kind of confidence that you may have and, I think overall we had to get out of the game of becoming like the wonder kid company that sells to some major entity 12 months in, I think there was just this huge rush, especially with media newsletters of like, oh, you build this up, you work, work really hard.And then, you know, the New York times comes and purchases you, right? And like it’s kind of far and few between. And if we’re playing that race, you know, if we’re playing that kind of game, it’s, you know, it’s, it’s, it’s not necessarily the right north star and being rushed into this idea of what success looks like.We have to really redefine for ourselves and what, like our core values have been. And we have to revisit that time and time again, and really just focus on delivering the best value that we can deliver.00:27:04 Nathan:Yeah, it sounds like you have a long time horizon, which I think is really, really important because so many people are. They’re focused on like, okay, this has to work in the next month, the next three months, the next two years. And you just, you burn yourself out. Like I I’ve been working, in six weeks.It will be the new year. And I will have been working on convert kit for nine years and like, realizing that I was like, oh, this takes a long time. And you get those best compound results over. It’s just a lot of time.00:27:33 Sherrell:It takes a while. Good things. Take time. And it’s really hard. you know, I’m a millennial and everything where we want it to have everything like yesterdayandwant it tolikeRight. I mean, yes, of course, absolutely. Like, that’s why I don’t cook. Right. Like Uber eats me please. So, it humbles you to really understand.I always, I always say, you know, like we’re understanding our own minds right now. we had to kind of go through our mature, our maturation phase of who are we? What is our content and our work stand for who is our audience? You know, having to kind of make those shifts and adjustments as we grew, the newsletter that we started is not the newsletter that we have today.We. We are going to have this highly kind of consumer driven newsletter. And as we started to look back at emails and names and titles, we kind of quickly realized, yes, our folks are kind of on the, on the periphery of like being consumer based. But these are people who hold really interesting titles at top tech companies, or they are, you know, coming from vaping companies.And so it really allowed us to see and understand, well, our content is helping to inform and give intelligence to these people who are going into work everyday, making decisions. It’s not just information for information sake. We have to fundamentally cater to a very different audience than, than how we started.And I’m honestly very proud of that evolution. And I’m also proud of the time that it’s taken, even for me to evolve as a. I mean, I went from me and my laptop and wifi to now having four full-time employees and 10 contractors that help us to build this thing, like every single day. And so that’s fundamentally over this time, horizon has been a transition and an evolution across the board, and I’m sure who you were and where you started nine years ago is fundamentally different than what you have built as a company today.But you need each of those steps, right? It’s that kind of crawl to walk, to run, to fly sort of phase. And I think we’re just working on practicing more intentionality. And now I have more brains. I have more, more hands, more ideas in this that makes it better every single day. And I, and I just try my best to like, honor that.00:30:03 Nathan:I love that. Yeah. It’s exactly what I think of it as what’s a journey that I can go on that will make me a different person. By the time I get there, like what’s the, not the easy path, but what’s the thing that I can undertake where it’s like, I, the only way to accomplish that is by becoming like leveling up and becoming a different person.And, and it sounds like you’re on a similar journey.00:30:27 Sherrell:Absolutely. I mean, I don’t know how you do this and you, and you don’t change or transition. And I mean sure. Would it have been nice to get that early win, whatever that looks like, and then kind of had the clout to say, oh yeah, I sold my first company and blah, blah, blah, blah, blah. And it’s like, yeah, sure, man.But that would have come with its own, you know, challenges. I mean, I, you know, went to grad school during the process and, you know, had to hire a managing editor to help the flow. So it was like getting up super, super early to go to class and like run the newsletter and deal with clients like in between class transitions and homework.And, you know, deliverables was not an easy feat, but I needed that time to help me become the leader that I am today and the journalist than I am today. And also to build the kind of network and relationships that would help us continue to grow into thrive. And I think more so now, and I, and I’m not sure if this is true for you as well, Nathan, you know, it’s less about just general execution and more about.What room. So I need to be in where I can learn and kind of see my business differently and see the opportunities in a way that are effective. I mean, we’ve always run a remote company and I’ve always wanted to run a remote company. And now that we’re remote and I have. Folks across time zones, you know, it is how do we continue to produce at an excellent level, but then also like be, you know, be sensitive to different time zones.And when we move an all hands meeting, how that kind of affects the workflow for the week, or, you know, some of my team members are juggling full families. And, told you earlier, you know, that we are our two-year-old director of mayhem with like, he has like three teeth. He’s like, you know, one of our favorite employees, sometimes like, you know, he calls it like 7:00 AM and just wants to chat and you have to be available for those conversations.And so, you know, again, you know, I think, I think this whole entire process is a growth journey and sometimes your north star does change. You know, I think that when I first started out, it was like, yeah, like we want to be just as great as this. You know, we want to be just as great as kind of these superstars that, you know, had access to a great deal of funding.Well, here was the thing they think when I was in grad school, I went to school for computational journalism. I went to journalism school at a time that there was a 40% reduction in staff of actual journalists. Like the industry itself was like, we’re dying, come on a Janice. Right. And watching these major publications that were like dominant leaders, completely lose their valuations and have to sell for pennies on the dollar compared to what they raised in venture capital.And so the other component to Nathan was that I realized I can’t compete on resources cause I hadn’t raised any money. Then we were doing strictly revenue. Advertising and sponsorship checks, and then eventually reintroduced subscriptions and subscriptions giving access to more premium content and developing an entire sort of newsletter experience and product experience that would cater to the subset of folks who wanted more and shared with us that they wanted more.And so I think the slowing down also enabled us to listen a lot more to our audience about who they were, what they were looking for, what they wanted. And it put us into a great place, even though it kind of felt like, okay, folks where they knew about us, but, you know, once the pandemic kind of shot off and our work was just out there and everyone’s online, they’re like, oh wait, like The Plug like has been doing this work for a very long time.Like their stuff is really dope, like that really catapulted us. And so I’m lab that we had built up such a body of work and reputation. So that once we started to kind of get this influx of subscribers and this influx of folks paying for the premium membership, we were ready. We already had things that they could tap into that were of excellence.And so, it is, it’s definitely a journey all the way.00:34:46 Nathan:So on that journey, well, so you have tens of thousands of subscribers now for The Plug. What were some of the inflection points in growing that audience? Was it perfectly linear or were there some things, you know, certain stories that took off where you added hundreds of thousands of subscribers in one go.00:35:03 Sherrell:Yeah. I mean, doing our work in public has been such a great benefit to us. I think before we were kind of in this closed community space, we just want to talk to our audience in there. well, we had to create greater opportunities and we learned this through a survey to our, to our subscribers. And they said, listen, like we love this work.And folks would email me or email our managing editor and have conversation, but they’re like, we want more conversation like amongst each other. we want to know who else is subscribed here. And so we had to do a lot more of our work in public, really engaging people across social media, because that really is just where people are, you know, whether it’s frequently or infrequent.That was kind of where audience, also wanted to engage either with myself or with our team members. And so pushing out our articles, creating, very engaging data visualizations to really show the prowess of our work and our reporting. a lot of our work has gone viral. A lot of our data, our data sets and visualizations have gone viral.It gives, it’s given us an opportunity to, again, like teach and allow people to grapple with information and sort of how that information plays a role in sort of some of the challenges people of color in tech have faced and also the opportunities and trends, that are on the horizon as there’s more distribution of access to capital and access to.And so doing that work in public and having clear stances and, continuing to host conversations, bold conversations, courageous conversations in public have really drawn more attention back to our original work back to our original newsletter. And so, and so again, experimentation, right?I mean, I would love to say we have this grand strategy. Most of it was listen, we’re doing really dope things. We need everyone to see what we’re doing. And so we’ve just, we’ve just refined it. you know, a lot more, we’ve ensured that our team has access to the tools to build out charts and graphs and things like that.00:37:09 Nathan:Yeah, that’s good. So a lot of content creators, you know, come into it from some other path, like I’m a designer turned blogger, right. but you really came to it from, I mean, you’re a journalist, you went to school for journalism and you have this tech and data background. And so I’m curious as you work, you know, these really data-driven stories and you bring like true journalism.Each of the stories, what’s something, well, I want to go two different directions, which always makes for a terrible question. one is, I, I’m curious for more of your process, like, you know, are you finding the data and then uncovering the story within it? or does it, you know, you hear a great story and that leads you into the data or does it, is it both directions?00:37:53 Sherrell:It’s definitely both directions. I mean, sometimes just being out and about whatever that looks like these days, you come across really interesting stories. we’re always engaging on social media and listening in to conversations and sometimes like that sparks, like. But mostly we are driven by a question and just the curiosity of, Hey, I wonder what’s going on with this, or I saw this opportunity, but what does this actually mean?And then it kind of finding the dataset and end, or having to build out our own datasets and then being able to tell a story from that. And the cool thing is that, you know, numbers can tell one side of a story, or, or they can tell multiple stories. And so the great thing is that it’s a constant feedback loop that’s going on in the way in which we identify, find or even presented.A lot of our readers are really, really great at even just sharing like, Hey, you know, I live in Oakland and like, this is what’s happening here with this particular company or organization, or, you know, I stumbled across this thread and just wanted to get your thoughts. And then we’re like, oh, Hey, you know, maybe we should, maybe we should kind of think through this and, and what data exists, where can we kind of go and find more insights?And then also, you know, on the weekends, I like long walks on the beach and reading a lot of research papers.And so,so like sometimesit helps to spark ideas and I’m sure that, you know, as someone like yourself, who’s also a creator and, you know, someone who loves to read really great work, having a multifaceted array of content around you all the time, whether you’re listening to it, reading it, watching it, it also helps to spark new ideas on how to, as we say, as journalists, like how to enter a story from like the back door, right.Not everything on its surface is what it is, but when you have an eclectic mix of content and, like I subscribe, you know, to, to things that are kind of way outside of my purview from tacking day, And that helps me to kind of think about other spaces and industries. I had a great conversation with a founder a few weeks ago, who was talking about these like warehouses.She has a data software company that like maps, supply chain and food and food ingredients as well. And she was just talking about how, like, there’s so many entrepreneurs, like in the state of Georgia who owned these like warehouses and manufacturing facilities and how like, you know, no one’s talking about these hundred million dollar plus companies that employ a hundred plus people.And they’re doing really well because everyone kind of wants to be on social media, like selling their product. And they’re the ones that like, ensure that products actually get made. And I just thought like, that is so fascinating. Like I wonder, you know, regionally, like where are the manufacturing plants in a, in a country that has shipped so much of its, you know, manufacturing overseas.And so just the curiosity of it. All right. It’s just the curiosity of, interesting conversations that we try to bring to the forefront.00:40:58 Nathan:That makes sense. Is there a story that you’ve worked on that. Or that you’ve worked on a published, broken in some way that has changed the conversation. Like one of these that’s gone viral. and I’m sure there’s plenty, but a favorite that you’d want to share.00:41:11 Sherrell:Yeah, I actually, this was a surprise, piece that went viral. this was, following the murder of George Floyd, last year. And I happen to be, on Twitter as I started to see a lot of tech CEOs, speak out and really address this issue on police brutality, and justice. And, you know, I had mentioned, you know, I’d been working in tech for a few years and you know, it’s not like this was an anomaly, right?We we’ve seen this happen in play out, unfortunately, in so many different ways, but I had never really seen corporate leadership or, even just tech leadership really speak out. And so I started documenting the public statements that were coming across my timeline and really scraping Twitter to kind of see which brands which companies were making these states.And also kind of comparing that across the board of what their diversity equity inclusion results were saying about their commitments to, black and brown workers who was actually in leadership roles, who was actually on the board and really getting a sense of our companies kind of here for the moment.Or are they actually kind of living what it is they say their, their actual core values are.And again, this was kind of a, project that I just want it to be able to have ready and to have something to say for the following week and decided with my team, well, we’re going to need some additional help so that we don’t miss out on any conversations that.May have happened. And so I allowed the database to kind of be open for people to contribute to. And I started creating a visualization, really creating a timestamp of when companies were speaking out against, sort of against just the general timeline as like the country sort of erupted in protests on a national level.It went viral immediately. and again, without intent, I was really trying to do some research and also just kind of share, like, here are some of the companies that have made statements and here’s the timelines. it went viral and it was overwhelming. I started getting messages across the board from CEOs, from recruiters.I even had. Folks who I’d worked with in previous years, reach out to me like they were like in Amsterdam, they’re like, you know, your, database your visualization, like we’re, it’s at our all hands. And like we’re talking through, 00:43:44 Nathan:Sorry 00:43:44 Sherrell:Our statement will be. I started getting signal messages and for those who are unfamiliar signal is like the private messaging app and encrypted and all of that.And I mean, people are sending me company emails and I mean, it was a great time be a journalist in that moment. And to really like, experience the wave of like what journalism should be in terms of, public service. It was also a very hard time, as you can imagine. as, as it was the middle of a pandemic, I’m at home by myself, with my plants in my wifi feeling somewhat powerless and just feeling like this is how I can contribute to the conversation into the movement and what really spurred out of that.And this idea of transparency as well as accountability. And, a year later we were able to work in partnership. The Plug was able to work in partnership with fast company to do an evaluation out of all of the commitments that had been made and all of the sort of, public statements and kind of PR moments where have companies now come when it relates to inclusion and diversity justice.And so it appears now. And so there’s much more, practice around evaluating those commitments, and asking companies to be much more transparent. And I think some policy as well, that is, that is kind of getting started in DC around how reporting on equity and inclusion should be commonplace for all employers And so, so that I feel very proud of, from our work, in terms of helping to spark that movement. And there were other folks who started building very similar databases in their specific industries. So from beauty to music to gaming, just across the board. and again, that was unexpected. I felt like there are stories that I like thought were going to go viral.Cause they, I thought they were really dope to me and people enjoy them, but this one definitely took off. And, I’m very proud of, of the work that we did. And I’m proud of the, the interns that we also had to, who, who stayed up with me for 36 hours to kind of get as thorough who could,00:46:00 Nathan:Yeah.00:46:00 Sherrell:As well.00:46:02 Nathan:Yeah. When you’re leading with data, that way the data has to be correct. It has to be accurate. that often is hard to do on a tight time on like that.Let’s talk about the business model for The Plugin. so you mentioned, you know, paid memberships as well as sponsorships. if you’re sharing it, what’s kind of the split maybe percentage wise between, you know, revenue from sponsorships or memberships and then any other 00:46:24 Sherrell:Yeah, I guess so. So memberships or subscriptions really make up about 25% of our total revenue. That’s something that we’re looking to actually increase. Our biggest goal was not to be wholly dependent on advertising response.00:46:37 Nathan:Yeah.00:46:38 Sherrell:But advertising sponsorships still does very well for us. And the great thing is that because we have a very specific audience, we are really able to capture advertisers and sponsors that are, you know, providing products, tools, and solutions to that audience in a meaningful way.And so those relationships have been really, really strong for us. and then we also have, licensing. So, we do original reporting, you know, as, as, as mentioned. And, we syndicate on the Bloomberg terminal, and that parts came about in April. and so all of the Bloomberg terminal subscribers folks across financial industry also receive our work and, you know, Bloomberg pays us annually, you know, for that particular access.We’ve also had prior relationships with folks. Business insider and mobile dumb. that’s a very small percentage of our total revenue, maybe about 10%, you know, advertising and sponsorships really make up the core. and then also, I mean, this isn’t necessarily like earned revenue, but, grants have been really, really critical to part of our growth is.I think, especially we haven’t taken on a lot of venture capital. you know, we’ve, we’ve raised a pre-seed round last year, which allowed us to bring on some employees. And so we’ve wanted to be very intentional with the way in which we took on capital, in order to grow. And, fortunately we’ve been able to participate in really great, journalism based accelerators, which have provided really cool grants and have allowed us to do things like spend on advertising, do website redesigned and audits and bring in, you know, a chief marketing officer.And so, so I’m, I’m still very proud of that because even though grants aren’t necessarily considered revenue, like there’s still work involved to apply to.00:48:36 Nathan:Yes.00:48:37 Sherrell:So the ROI is really strong. and it also means that I give up less of the equity in my business, and we’re able to use those dollars, effectively.So that’s the breakdown.00:48:47 Nathan:Yeah. like working with sponsors, what’s something. You know that, you know, and understand now that like you wish you knew two or three years ago where you’re like, 00:48:56 Sherrell:My God. 00:48:57 Nathan:Pull aside server out to use it it’s three years ago and be like, let me give you a little advice. What would you say?00:49:02 Sherrell:It’s just so many things. My gosh, I just wish we had like a full day, day, maybe like a nice hearty drink. you know, honestly, just did not know what I was doing in the beginning. kind of took whatever. I think because we never tried to compete on numbers, we tried to compete on value, demonstrating that.And, and being able to articulate that to sponsors, is always kind of an ongoing challenge. you know, and, and knowing the leads the lead times as well. We’re very fortunate in that. So much of our revenue from advertising is typically inbound. So we haven’t had to do a lot of like chasing. and, and as you know, like just pitching, it just takes a while.And if you don’t have the team, the staff to kind of manage that process, it can get a little crazy. but one thing I will say is really identifying, the assets early on and sort of being clear about the metrics that you can deliver. I think a lot of times, you know, we’re kind of only measuring, like click through rates or things like that.We did a lot of like virtual events before that became commonplace in the world. we really should have, created full packages that helped us to both expand our brand, and also really highlight, the core product of our partner.But I think we could have been a bit more judicious in terms of who we partnered with and why, and sort of how that was going to be a best fit. And then also, the retention as well, selling not just for that time, but really looking across the spectrum of opportunities to continue that relationship and continue that inflow of cash, every quarter or, you know, every year.Again, we, I think we got some really good lucky breaks, but I think overall we’ve had to be a bit smarter about overall inventory, and ensuring that, that, you know, we’re, we’re keeping more than we’re having to go out and pay.00:51:05 Nathan:Yeah. So when you’re talking about packages, is that like saying, Hey, you’re sponsored the newsletter for three months and these events that we’re doing, and like, you’ll be a title sponsor across all of this, rather than saying, you know, we chart our CPM on the newsletters, this, and so a single slot00:51:21 Sherrell:Yeah, absolutely. I think that, we’ve had to measure against like, what is the actual work involved in integrating a particular advertiser into our emails? you know, a, a CPM kind of works well when you have a significant subscriber list. Right? And so I think that that kind of delivers tremendous value, but for us, because our newsletter, you know, isn’t the tens of thousands versus hundreds of thousands.You know, we’ve had to really charge based on value and engage with. And sort of caliber of our audience, and really also tie that into how do we reinforce messages so that your ad or your promotion or your call to action is not lost in the sauce? right. So whether it be through like dedicated emails, a, an IgG live or a LinkedIn live conversation, the biggest thing for us is really being able to deliver value to our audience at the end of the day.And not just like, oh, like here’s like a random sort of like product, we should buy it more. So, you know, how do you, like we, we’ve had some financial institutions that have, advertised with us and their goal has been to recruit. More companies into their accelerator programs or things like that.So there’s really a strong use case that you can easily sell to advertisers at this level where they’re really looking for much more than just like the banner ad. they’re also looking for engagement. so how do we create engagement opportunities that fit our brand and also give, an opportunity for that engagement piece amongst our readers, who also want to kind of get to know each other.And so creating those kinds of moments, we’re able to sell those as packages versus kind of that one-off like here’s a banner ad go a God, give us a report later. so, so, so a little bit more00:53:21 Nathan:Yes.00:53:21 Sherrell:But you, you kind of build for longevity.00:53:24 Nathan:Yeah, that makes sense. Okay. I want to talk about the, the team side of things. Cause a lot of people start, you know, it’s relatively easy to start a newsletter these days and it’s just them for a period of time. And then it gets to the point where you realize, okay, I’ve built something bigger than myself.And sometimes people scale up really fast and then they find that that’s really challenging and really unsustainable, you know, if you have a down couple months with, sponsorships or whatever your revenue stream is. so it’s just hard. So when did you really think about bringing on your first team member and how did you go about like methodically scaling up the team, to what happen.00:54:02 Sherrell:I could say like the first nervous breakdown.00:54:08 Nathan:I should, I should lead with that question going forward. When was your first nervous breakdown? As a creative,00:54:14 Sherrell:Right?00:54:15 Nathan:Will have a story.00:54:16 Sherrell:Absolutely.No. It really, I really looked at, where I was feeling too exhausted to do the kind of work that I wanted to do, because I was kind of in the weeds of the newsletter also feeling like, okay, what’s going to make people stay subscribed. What’s going to make them feel like The Plug continues to be interesting on the nose and giving me something that no one else is going to give me.And that’s hard to do consistently when you’re by yourself, because you have great days. You have not so great days. You have, sometimes you get sick. Sometimes you need to fly to back home for a friend’s wedding. And it’s like, your level of concentration has to really, really scale through other people who are talented, if not more talented, to really bring you to the next level of your work.And so. Once we sort of were able to take on a little bit of capital from an angel investor. I brought on our managing editor, to really take over that process of the newsletter and to really help ideate with me where the newsletter was, where it should go. we really benefited from being in different sorts of, journalism accelerators, as I mentioned earlier, because we also got to learn from other news teams and newsrooms about the anatomy of a strong newsletter and sort of thinking through the entire process from start to finish of how we build out our newsletter.And then of course getting feedback and doing more surveys and collecting the data from our audience on what they were looking for. So again, constant experimentation, but also being open to, to realizing like, okay, this is good, but how do we go from good. And just even now, as we’ve had one of our reporters launch the HBCU newsletter, you know, we kind of talk through the shifts of that as well.And sort of know this is a completely different newsletter compared to our weekly briefing. and so it takes on a different tone. It takes on a different feel. It has a different kind of, objectivity that we kind of want to ensure, continues to serve in, in feed our audiences. So, everyone on our team is in some way connected to building the newsletter.We have a section in our slack, called editorial and everyone just tosses, really interesting articles they bred or tweets, or just Abe. I found really interesting into that and it helps us to really like brainstorm like what the newsletter should be. And the cool thing is that it really has. Gives you an insight into the minds of your team members to see like, well, what are they reading, right?What are they subscribed to? it that they find interesting? So we’re all contributors, you know, at the end of the day, and it’s helped so much because it’s not just all on you as a leader, right? Like we have to continue to grow the business. We have to hire more people, make sure that money comes in so that everyone can like, you know, get paid and by crispy cream or whatever it is, they buy with their money and, and continue to, to find ways, to grow even just the subscriber list, which has its own kind of marketing needs.But yeah, it really came from that breakdown of like, I’m getting sick of this and I want this to be great, but I’ve reached my capacity on the day-to-day basis and I need other people to help chime in to make this great.00:57:43 Nathan:Yeah. I like that. Working with the team. It’s just remarkable and wonderful. I know a lot of people who like their whole dream is to be a solo entrepreneur and they set up, you know, they’re publishing and everything they do so they can run it just themselves. And it’s a highly profitable business and I have a ton of respect for them, and that’s just not at all what I want.Cause I want a team exactly what you’re talking about to produce a newsletter and to put all of this content together. And you can just do so much more with the team. So anyway, I’m preaching to the choir here.00:58:13 Sherrell:Well, I get it. Like, I was such a huge fan of like Paul Jarvis has company of one. And I think initially that’s kind of the direction I was going in. but I realized like I didn’t want to just do this. I wanted to produce really strong visualization. I wanted to produce really strong, original content and also do, you know, live conversations and host events and, and, and just really like create.Opportunities for touch points and the ways in which people learn and engage, which isn’t always like through reading. Right? Some, some of it is audio. Some of it is, is visual. So, totally hear you. I mean, I think that we all would like some kind of like automated system that works like kind of perfectly.But I find that I also learned so much from having a team and people who think vastly different than I do. And, and, and people who are bringing new ideas every week, it keeps, it keeps the work exciting.00:59:10 Nathan:Yeah. And I think that, what I love about Paul’s work is that he’s pulled together all these examples to say, Hey, if you want it, this is something that’s available to you. You can, you know, and then people could look at it. So yes, that’s what I want. Or they can, you know, like so many people, you know, in your early career where that mentor for you or something else.We can have those examples, as well.I want to wrap up with that, related to goals for the next year. My friend Clay Hebert likes to ask this question of, “If we were to meet a year from now with a bottle of champagne, what would we be celebrating?” What’s the thing that you’re working towards that you hope to accomplish in the next year, that we’d sit down and celebrate?00:59:54 Sherrell:That’s such a great question. I really love champagne, so I want to get this right, so that this happens.I think for us, it is launching at least two additional newsletter verticals. One hyper-focused on climate and green tech, led by innovators of color.Secondly, sort of a more essay exposé from thought leaders in this space, that becomes a regular cadence for us.That’s kind of one of my major goals. I think also, secondarily, that we really have a full fledged functioning team, growing by maybe four additional team members, which would include researchers as well as additional journalists. Again, we’re fully remote, but we are producing great work at a very, very high level.We’re also seeing that reflected in the kind of partnerships and advertising that we have. That, for me, as a leader I have effectively curated an incredible team, and we’re doing the work that we said we wanted to do, and it’s having impact and it’s setting a standard, and we’re in all the rooms that we want to be in.Those were lots of things, Nathan.So, a year from now I expect champagne.01:01:15 Nathan:Sounds good. We’ll make it happen.Well, where should people go to subscribe to The Plug and follow everything that you’re doing?01:01:21 Sherrell:Absolutely. Head over to TPinsights.com. We’re also TPinsights across the web, and you can always come hang out with me as well on Twitter, because that is where my life starts and ends every day.01:01:37 Nathan:Sounds good.Well, thanks for coming on, and we’ll have to make a plan for that bottle of champagne.01:01:42 Sherrell:Absolutely. Thanks so much for having me, Nathan.

Matthew Kepnes runs the popular travel blog, Nomadic Matt, and also writes a successful newsletter. In fact, Matt’s newsletter is one of the biggest I’ve had on the show. His book, How to Travel the World on $50, is a New York Times Best Seller.After a 2005 trip to Thailand, Matt decided to leave his job, finish his MBA, and travel the world. Since then, he’s been to nearly 100 countries, and hasn’t looked back. Besides being a New York Times best-selling author, Matt’s writings have been featured in countless publications. He’s a regular speaker at travel trade shows, and is the founder of FLYTE, a non-profit organization that sends students overseas to bring their classroom experience to life.I talk with Matt about his unique approach to running his business. While others are building online courses, Matt has shifted to doing more in-person meetups and events. We talk about his newsletter, and we also talk about growing your Instagram follower count, scaling a business as a solopreneur, and much more.In this episode, you’ll learn: When & why you need to start outsourcing day-to-day tasks Matt’s email opt-in strategies and tips to get more subscribers The most important metric about your email list How to quickly get more followers on Instagram Links & Resources Blue Ocean Strategy Matador Lonely Planet Blue Ocean Strategy book Pat Flynn Women In Travel Summit Traverse Cheryl Strayed ConvertKit TravelCon FinCon Podcast Movement World Domination Summit Hootsuite Tim Ferriss Seth Godin OptinMonster Seth Godin: This is Marketing Rick Steves Nathan Barry Show on Spotify Nathan Barry Show on Apple Podcasts Matthew Kepnes’ Links Matt’s website Follow Matt on Twitter Matt’s Instagram The Nomadic Network Nomadic Matt Plus Episode Transcript[00:00:00] Matthew:When I started these courses back in 2013, there wasn’t a lot of folks. Now you have so many people with courses, so many Instagrammers and TikTokers selling their stuff. It’s sort of like, is this worth the time to really invest in it when my heart really isn’t in it? How can I maintain 400K in revenue a year? Is that the best use of our resources? The answer is, not really.[00:00:33] Nathan:In this episode, I talk to my long time friend, Matt Kepnes, from Nomadic Matt.Matt’s got a travel blog that’s wildly popular, and he gets into that—shares all the numbers. He’s probably one of the biggest newsletters that I’ve had on the show, so far.What I love about him, in particular, is how thoughtful he is about his business model.Most people are just adding more courses and figuring out how to grow revenue; honestly, what’s now fairly traditional ways, and it’s quite effective. Matt takes another approach. He gets into in-person events and meetups. We get to talk about why in a busy, crowded online world, he’s actually going offline.I think that Blue Ocean Strategy he references, the popular book by the same title, I think it’s interesting, and it’s something worth considering when some of the online strategies don’t work. We also get into a bunch of other things like growing his newsletter. Like I said, it’s quite large.Then, also growing an Instagram following. Instagram is not something that I’m going to actively pursue, but it’s interesting hearing his approach of what you do if you’re at 5,000 followers on Instagram, and want to grow to 50,000 or more.So, anyway, enjoy the episode.If you could do me a favor and go subscribe on Spotify or iTunes, or wherever you listen if you aren’t subscribed already, and then write a review.I check out all the reviews. Really appreciate it. It helps in the rankings, and I’m just looking to grow the show.So, anyway, thanks for tuning in today. Let’s go talk to Matt.Matt, welcome to the show.[00:02:06] Matthew:Thanks for having me, Nathan. I’ve been trying to get on this podcast for ages.[00:02:10] Nathan:Well, don’t say that, that’ll make people think they can get on just by asking. Really, you came to my house and stayed in my cottage on the farm, and then you’re like, “Yo, have me on the podcast!” And that’s when I was like, “Absolutely.” But if anyone just asked, that would not be a thing.[00:02:26] Matthew:No, I just mean I finally—I’m excited that I’m worthy enough in my blogging career to be on.[00:02:33] Nathan:Oh, yes.[00:02:35] Matthew:I’ve made it.[00:02:36] Nathan:Yeah. It’s only taken you, what, a decade and a half?[00:02:39] Matthew:13 and a half years. Slow and steady wins the race.[00:02:43] Nathan:That’s right.I actually want to start talking about that side of it, because I’ve been in the blogging world for 11 years now. But even I feel like things changed so much in the first couple of years, even before I entered into the world. So, I’m curious, going back to the early days, what were the prompts for you to come into the blogging world and say, “Hey, I’m going to start publishing online”?[00:03:10] Matthew:Yeah. You know, it was a very haphazard, there was no grand plan. Like I had Zanger when people had Zeno’s, which is, you know, a personal blog, way back, you know, 2003, whatever. And so what, I went on my trip around the world in 2006, I just kept updating this Zynga. You know, it was called, Matt goes the world and it was just like, here I am friends here I am.And then, you know, everyone was really excited in the beginning. And then after a while I got sick in my update because the know their back of their office job. So I kinda just forgot about it until I came home and January, 2008 and I need money. And so I started a temp job, and I had a lot of free time and I really just hated being back in the, the office with the walls and everything.And so I was like, I need to earn money to keep traveling. And so I started the website really as with the goal of it being an online resume, you know, it was very bare bones. I used to share a travel news, have an update, like tips and stories from my trip. And then there was a section where we’re like, hire me and it had my features and, you know, the guest blogs I did, I used to write for Matador travel.So just as a way to sort of build up, a portfolio of like, Hey, Yeah, freelance writing because I’m wanting to read guidebooks, you know, I wanted to write for lonely planet. That was a dream, right. The guidebooks. And so just the blog was a way to hone my skills and just get in front of editors to be like, Hey look, I do right.You know, here’s where I’ve been, you know, and, and sort of build that base. And eventually that became a thing where I didn’t need to freelance. Right.[00:05:03] Nathan:Was it called nomadic Matt from the beginning.[00:05:06] Matthew:He was, yeah. I B two names, nomadic Matt. And that does the world. Right. Because I like the double entendre of it. Right. Even though, but just cause I have a weird sense of humor and all my friends were like, you can’t do that one. You gotta do nomadic Matt. It was really good because it’s much better brand name, you know, in the long run.But again, I wasn’t thinking about that. Right. I wasn’t thinking like, oh, I’m going to start this brand. You know, I gotta think of a clever name that people can remember. It was like,Oh a place where people can see my work.[00:05:39] Nathan:Right. Okay. So now 13 and a half years later, what’s the, what’s the, the blog and newsletter look like. and I want to dive into the business side of it because I think a lot of people build successful newsletters, audience-based businesses, but don’t make the leap to like something bigger than themselves.And so I want to dive into all those aspects of it.[00:06:01] Matthew:13 years later, it’s seven people. We just hired a new events coordinator to help. my director of events, Erica, coordinate all these virtual in person events that we’re going to kick off again. I have a full-time tech guy, a full-time director of content. We changed his title, but like three research assistants, because.I picked a niche that like is always changing. Right. You know, you have a fitness website, how to do a pull up. It’s just, that’s it,[00:06:37] Nathan:You ranked for that keyword. You’re good to go.[00:06:40] Matthew:Yeah. Like how to do a pull up, doesn’t change what to do in Paris or the best hospitals in Paris, constantly changing, you know? so it takes three resources, distance.Plus my content guy, me that basically keep up the content and then I have a part-time, graphic designer and part-time social coordinator.[00:07:00] Nathan:Nice. And how many subscribers do you have in the list now?[00:07:03] Matthew:We just called it, so it’s a two 50 because we just, cause I haven’t shaved it off in like five years or so. So we basically everybody that hasn’t opened the email in one year where we’re like, you want to be on.And like 2% of them click that button. And then we just got rid of the other 90%. It was like 60,000 names.[00:07:30] Nathan:Yeah. So for everyone listening, two 50 in this case means 250,000.[00:07:35] Matthew:Yeah.[00:07:36] Nathan:Just to clarify, I 7% businesses off of 250 subscribers would be remarkable. That would be just as impressive, but that’s not what we’re talking about here. going into, so a lot of people, talk about or worry about, should I prune my list or that kind of thing?What were the things that went into that for you? That’s a big decision to, to prune 60,000 people off a list.[00:08:00] Matthew:I think it was probably more, maybe I want to say six 60 to 80 I somewhere around there. we were pushing up against our account before I went to the next billing step.So that’s always a good impetus to prune the list, but you know, I I’ve been thinking about it for a while because. You know, I I really want to see what my true open rate.Is You know, like, okay, I have all these people and we were sending it this, I have multiple lists, but the main weekly list was like, 310,000-315,000 but it’s been so long since we called and we have so many emails there and I just really wanted to get a true sense of like, what’s our active audience.And so between, between that and, pushing up against the next tier price tier. Yeah. it yeah. It’s cool to say like, oh, we have 300,000 300, you know, rather than 250,000 Right. But who cares? Right. I mean, at the end of the day, it’s just a vanity metric, right? Yeah. It sounds cool. I get a million emails. Right. But if you only have a 10% open rate, You really only have 100,000.[00:09:20] Nathan:Right. I think that the times that it matters is maybe when you’re selling a book to a publisher and that might be the only time that you like that dead weight and your email us actually helps you.[00:09:33] Matthew:Yeah. Like if you’re, or you have a course, you know, are you trying to promote your numbers, but people would probably lie about that stuff too. yeah, so like, it really doesn’t matter because all that matters is like, what’s your true audience? Like who Who are the people that are really opening your stuff?[00:09:50] Nathan:Yeah. So let’s dive into the, well, I guess really quick, I should say I am a hundred percent in the camp of, like delete subscribers, like do that once a year, that kind of thing. Clean up the list, go for the highest number of engaged subscribers, rather than the highest number of subscribers. It’s just[00:10:06] Matthew:Right.[00:10:07] Nathan:To track.[00:10:08] Matthew:And, and I think you would know better than me, but isn’t this a good. Like signal to Gmail. And you know, when you, you don’t have a lot of dead emails, just go into a blank account. It’s never getting opened or marked as spam or whatever.[00:10:24] Nathan:Yeah, for sure. Cause a lot of these times, there’s a couple of things that happen. One is emails get converted to spam traps. And so it’s like say someone’s signed up for your email list six years ago And, they haven’t logged into that email account for a long time.Google and others will take it and convert it to a spam trap and say, Hey, this email hasn’t been logged into in six years.And so anyone sending to it, it’s probably not doing legit things now you’re over here. Like, no that person signed up for my list, but they’re basically like you should have cleaned them off your list years ago. And then if that person were to ever come back and log into that Gmail account, do you remember like, oh, just kidding here, have the, have the email account back, but they’re basically using that.And so you can follow all the. Best practices as far as how people join your list. But if you’re not cleaning it, then you will still end up getting these like spam hits and, and other things. So you absolutely clean your list. Let’s talk the business side, on revenue, I don’t know what you want to share on the, on revenue numbers, but I’d love to hear any numbers you’re willing to share.And then the breakdown of where that comes from, whether it’s membership, courses, conferences, that sort of thing.[00:11:35] Matthew:Yeah.So there’s like the pre COVID world and the post COVID world. Right. You know, like,[00:11:40] Nathan:Yes.[00:11:41] Matthew:Cause I work in travel, so like, you know, pre COVID we did over a million and like I was probably gearing up to like in 2020, like one, five, I think I were going to get a little over one five. and again, you know, this is, I work in the budget travel side of things, right.So like it’s going to sell a lot of $10 eBooks to get up to seven figures. salary books are 10 bucks. and so. Postcode during COVID week, I think in 2020 made like half a million. and this year we’ll probably get up to three quarters,[00:12:23] Nathan:Okay.[00:12:24] Matthew:K.[00:12:25] Nathan:He was coming back,[00:12:26] Matthew:Yeah. Yeah. and I think next year we’ll, we’ll get back over seven and then basically like how to go from there.You know, so maybe 20, 23, I might get to that one, five that was going to get to in 2020. most of the revenue now comes from ads, and then affiliates. we did, we did do a lot on courses, but then I, one of the things that, you know, a big pandemic that stops your business, allows you to do is really look at the things you’re doing because every.Zero. So it’s like when we start back up, is this worth investing time in? And so the answer is no. So we dropped down from, I think, peak of doing like $400,000 a year and horses, and this year we’ll do maybe 40. and that’s mostly because we just leave it up as like, you can buy this, we update it every six months.If it needs, it’s basically like a high that blog course get all my numbers and tactics and strategies in there. but we don’t offer any support for it. Right. It’s just, you’re buying information. and so it’s very passive in that sense, but it’s not like a core business where we’re really moving and we were doing this pre COVID is moving into events and membership programs.So like we have pneumatic map plus, which gets you like all our guides, monthly calls and sort of like a Patriot on kind of thing, but like free.[00:14:03] Nathan:That cost.[00:14:04] Matthew:Five to 75 bucks a month, depending on what you want. So it’s 5 25, 75. Most people opt for the five, of course. And it’s really geared to like, get the five.But you know, that brings now, I think like three or four K a month. and then we have the events, which is donation based, but there’s just like another two K a month. And so this is like, since COVID right. So like, that’s say call it 50 K a year of, of revenue that we’ve added in. They didn’t exist before.And now I know you’re, you can compare that against the loss of the courses, but we had been phasing those out for years. and so that’s really where we want to grow is bringing in more, you know, monthly revenue for that. Right. You know, Once we started, it’s easy and we’re gonna start doing tours again and, you know, so more high value things that don’t take as much time.[00:15:08] Nathan:Right. So on the core side, I think a lot of people listening, maybe they have an email list of five, 10, 15,000 subscribers, and they’re like, Hey, the next thing is to launch a course. And they’re hearing that’s where a bunch of the revenue is. And so it’s interesting you moving away from that. So let’s dive in more.What, what made you look at the core side of your business and say, I don’t want to like restart that in a post COVID world.[00:15:33] Matthew:Yeah, there’s just, there’s a lot of competition, right? So like, I think it was like a blue ocean, red ocean strategy, you know, to think of that book of, you know, Blue Ocean Strategy. Right? One of the reasons we went into events is because a lot of our traffic comes from Google. And so it’s a constant battle of always trying to be one or, you know, in the first couple of spots.Right with every blogger in every company with SEO budget, but there’s not a lot of people doing in-person events or building sort of a community in the travel space. So I looked at that of being like, okay, there are a lot of people doing courses and they love doing courses and they’re great teachers, you know, they’re, you know, you get folks who know like path when, you know, low, like everyone, all these teachable folks, you know, they, they love that stuff.That’s not where my heart really was. And so thinking of like, this is a red ocean now, because you have, when I started this, these courses back in 2013, there wasn’t a lot of folks. Right. But now you have so many people with courses, so many Instagrammers and tic talkers selling their stuff. It’s sort of like, is this worth the time.To like really invest in it when my heart really isn’t right. Like how can I maintain your 400 K in revenue a year?[00:17:02] Nathan:Right.[00:17:03] Matthew:What’s it going to take, you know, is that the best use of our resources? And the answer is not really, you know, let other people do that. Who love it. I mean, you want to buy my information.It’s it’s solid stuff. Right. Everyone loves the advice, but to really create like a cohort, like your class, which is sort of like the new version of courses, you know, like, whether it’s a month or three months, it’s sort of like, you go with this like cohort, right. My heart really wasn’t into it because we can invest more in doing events and conferences and really in-person stuff.Especially now that everyone’s really excited to do stuff in person again, with a lot less competition. It’s easy. It’s easy to start a course, but there’s a lot of capital investment in doing events that we have the resource to do that, you know, somebody with a 10,000 email list might not.[00:18:03] Nathan:I think I see a lot of people going into courses in, particularly as you alluded to cohort based courses where they’re doing it, like, Hey, this is a whole class that you’re doing, you know, you’re doing the fall semester for the month of October or whatever it is, I’m doing it, doing it the first time and really enjoying it because it’s a new challenge they’re showing up for their audience.It’s just, it’s super fun on that, doing it for the second time and going, huh? Okay. That was way easier and way less. And then the third time they go, I don’t think I want to do this anymore. Like if the money is good and I just don’t enjoy showing up at a set time for a zoom call or whatever else. So it’s interesting of watching people jump on a bandwagon and some people it works for really well, and that is their strength and they love it.And then other people that I’m going to like, look, the money’s good. And this is this just, isn’t what I want to spend my time on.[00:19:02] Matthew:Yeah. You know, I’ve been doing it for, you know, seven, eight years now and I just sort of lost the passion for, you know, I think it’s, I like when people take the information, they succeed with it. But I think after a while you start to realize, you know, it’s sort of a 90 10 rule, right? You, 90% of your students, aren’t really going to do anything with it.And it’s not your fault. It’s just because they become unmotivated or, you know, so we tried to switch to the cohort based to be like, okay, this is the class weekly, weekly calls.You know, come on, come together and you still get this drop off rate. That’s, you know, sort, it gets this hard and you’re like, all right, I’ve been doing this for eight years, you know, like moving on.But I mean, if you have the love for like pat loves it, you know, like you’ve got a whole team about it, he’s got all these cohorts stuff that speaks to him where I think I’d rather do stuff in person that[00:20:01] Nathan:Right.Well, let’s talk about the in-person side. Cause you did something that most people think is really cool and almost no one realizes how hard it is. I think I know how hard it is because I’ve attempted the same thing and that starting at a conference where everyone’s like, you have this big online following, like what you just need to, you know, you have hundreds of thousands of people you just need, I don’t know, 500 or a thousand of them to show up in a suit, that’s gotta be easy.Right. And so they go and sort of conference, it’s wildly difficult. And so.[00:20:33] Matthew:Difficult.[00:20:34] Nathan:I’d love to hear what made you want to start the conference and then yeah, how’s it. How’s it gone so far?[00:20:40] Matthew:Made me want to start the conference was I really don’t think there’s a good conference in the chapel space. Yeah. And there are good conferences in the travel space that are very niche and narrow. you know, like there’s a woman in travel summit.That’s really great. There’s one in Europe culture verse, which I liked, but that’s like a couple of hundred people there. Wasn’t like a, something to scale, right. With wits, which is women to travel is like 300 people. There was, this is no thousand person, 2000 parts. And like mega travel conference for media that has done like, you know, the conferences we go to where it’s like high level, you know, people coming outside of your immediate niche to talk about business skills.You know, there’s, you know, In the conferences, there are, there’s always the same travel, like it’s me and like these other big names, travel bloggers over and over and over again. I want to take what I’ve seen and, you know, from social media world to, trafficking conversion, to mastermind talks, you know, to take all these things that I had gone to, we were like, let’s bring it together for travel.Let’s create a high level, not a cheap, like hundred dollar events, like, you know, with major keynotes who get paid to speak, because you know, in a lot of travel conferences, you don’t get paid to speak, right? So you’re high. You’re going to get, you know, Cheryl strayed that come to your event for free.That’s not waking up to do that. You know, I, you know, and while I can get nice deals from my friends, you still got to pay people right. For their time. And, and so that allows us to have a larger pool of people to create the event that I want to do. Because we will also get into the point where why should somebody who’s been blogging for five or six years, go to travel blogging conference app when nobody is at a more advanced stage of blogging than you are, you know, nobody understands SEO better than you do, right?So like after a while you get into this, just drop off of people being like, do I want to fly around the world and hang out with my friends? So I wanted to also create an event where that I could go to and learn something is that I knew that would attract some of the other OJI, travel bloggers.[00:23:06] Nathan:Yeah. So how the, how the first one go, like what was easier than you expected and what was much harder than you.[00:23:14] Matthew:The first one went really well. We had 650 people, and you know, the next one we had 800. But now we’re closed because of Kobe, but we’re going to do one in 20, 22. And hopefully we get 800 again, things that shocked me, people buy tickets and don’t show up. Right. That’s weird. Right. Cause I was like, okay, we have 700, you know, I expected maybe like a 5% attrition rate, you know?So like I sold my 750 tickets, but then like six 50, those 600 showed up because the other 50 of those speakers, right. I was like, wow, that’s a lot of no-shows for not achieving conference, you know? And so we plan, you know, a 10% attrition rate now.[00:24:04] Nathan:And you just mean someone who doesn’t even pick up their badge? Not even, they didn’t come to share us rates keynote, but just like they didn’t show up to anything at the conference.[00:24:13] Matthew:Yeah, they just did not show up to the conference at all, you know? And. So that was a shock me. I mean, I know I work in travel and, you know, people get last minute of press trips or they, you know, they buy their ticket and they can’t come cause, or they got stuck in the Seychelles or whatever, but I did not expect such a high level of no-shows. Because the food here’s another thing, food costs a lot of money. Right.You know, I, I fully understand why the airlines took one olive out of your salad. Right. Because it’s one olive, but times a million people every day it’s actually adds up. Right. So like you think, oh, well it drinks five bucks.That’s cool. We’ll do a happy hour. Okay. Now times that by a thousand drinks Write, you know, times two, because everyone’s drinking two or three, at least two. Right. So then you’re like, okay, that’s a $15,000 bill that you ended up with. you know, when everyone is all set up. Tax and tip hotel.It’s crazy. It’s like, okay, these fees, you’re like, oh, I got to spend this like, yeah. Okay. Here is your lunch bill 50 grand.But then there’s this fee that fee, this fee, this fee like Jake had like 65. You’re like, all right. I guess I got a budget for that too. So that was, that was really weird. Like high is the lunch cost, $40,000, you know, and actually hotels, overcharge, and they add a bunch of fees and yeah, you can get them pretty quick.[00:25:46] Nathan:So if you were, if I was starting to conference. They have 50,000 people on a email list or a hundred thousand. And I’m like, Matt, I heard you started a conference. I’m going to do it too. What advice do you have for me? Like what are the first things that you’d call out?[00:26:03] Matthew:It’s going to cost like three times more than you think. pricing. Where I went wrong in the second year. Right. So like we’ve lost money the first two years doing it, but I expected to lose money. It wasn’t because I was investing in this long-term thing. Right. But we’re at where I lost more money on the second year is that I really factor in flights as well as I did, like I kind of low balled it.And so I always think he should. Oh. And I also invited, I kept inviting people without really seeing, like, where was I? on my like speaker fees. Right. So like really creating a budget and then sticking to it. And even if that means not getting some of your dream folks, to a later year, but working up the food and beverage costs first, because you know, you go to the hotel and they’re going to say your F and B, you know, is $90,000.And if they never going to hit that, no, you’re going to go way. You’re going to blow cause you got to get them to say, what are all the fees? You know, like, okay. You know, if I have a 300 person conference and I want to do two lunches, what does that look like?Plus all the taxes and fees,[00:27:23] Nathan:Okay, well, you, the launch price and you’ll, you’ll pencil that into your spreadsheet and they’ll fail to mention that there’s mandatory gratuity on top of that and taxes and whatever[00:27:33] Matthew:Yeah,And whatever, you know, plate fee there is. Right. So you gotta factor all that in and then look at what you got left.[00:27:40] Nathan:It’s like when you’re buying a car and you have to talk in terms of the out the door price in[00:27:45] Matthew:Yeah.[00:27:46] Nathan:The sticker price,[00:27:47] Matthew:Yeah. I made that mistake when I bought my car last year, I was like, oh 17. And I was like, wait, how did 17 go from 17,000 to 22? And like, well,[00:27:56] Nathan:Right.[00:27:57] Matthew:Thing that I was like, ah, okay,[00:28:00] Nathan:Yeah. Do you think w what are some of the opportunities that have come out from running the conference and has it had the effects of your community that you’ve hoped? It would,[00:28:10] Matthew:You know, this is a very, blogger faced event, you know, more than just travel consumers. but it’s definitely allowed me to, you know, meet folks like Cheryl Austrade, you know, great way to meet your heroes. Is there pay them to come speak at a conference? so, you know, I, I know Cheryl, like, that’s cool.The becoming more ingrained in sort of the, the PR side and with the demos and the brands, because, you know, on the website, I destination marketing organization.[00:28:44] Nathan:Okay.[00:28:45] Matthew:So they’re like, you know, visit, you know, Boise visit Idaho, we call them a DMO. And so like since I don’t really do press trips on the website, I don’t know a lot of them really well.And so this has been a way to be, become more ingrained on that sort of industry side of events and not live in my own. and that’s helpful because now I know all these folks, when we want to have meetups that might be sponsored when I do a consumer event, which is next up. So get these folks to come for that.So it’s just really been good, just professionally to meet a lot of people that I would normally just not meet simply because I go to events and they were like, Hey, come to our destination, we’ll give you a free trip. And like, you have a policy. And so I don’t get invited to as many things as you would think.[00:29:37] Nathan:Yeah. Why, why do you have that policy? What do you like? What’s behind it. And why is that different from other travel bloggers?[00:29:45] Matthew:Hi, it mostly stems from my hatred of reciprocity. You know, like if you, if I go on a free trip and it sucks, like I then create, it’s awkward. If I have to go like hot, like, Hey, you suck. And I have to write this online. Then it creates a lot of bad blood that gets talked about, you know, it’s a very small industry.People move around a lot, so you get less opportunities or I can just go, Hey, I’m not going to write that. And then they feel bad. Cause like, you know, like you’re a nice person just doing their job, you know, like it’s not your fault. I had a bad time. you know, I did this once with a friend and she gave me a couple of places to stay, at a hotel in San Jose, Costa Rica and chill out and sort of tell was really far out of town.And th the amount it took me to take a taxi back and forth. Like, I could’ve just got a place right. In the center of San Jose, you know? And so I was like, I really, I just don’t think it’s a good fit for my Anya. And she was very unhappy about it. I was like, I mean, I could write in, but I have to say that.Right. Yeah. And so I just never wanted to put myself in those situations again. I also think that taking a lot of free travel, like I do budget travel. So you given me a resort like that. Doesn’t how does that help my audience? So if I start living this awesome life and getting free stuff, that’s great for me, but it’s not good for my audience.And so I don’t mind taking free tours. Like, let’s say I’m going to go to Scotland. Right? I did. This actually was real life example. I wanted to access cause I wanted to write about scotch. So I was like, Hey, I don’t want to do like the public tour. you know, that 20 bucks, you know, it’s like 10 minutes and you get the, I like, I want to talk to people because I want quotes for articles.I’m going to do like history stuff. So I contacted the Scottish tourism board and they got, got me visited. I that’s where I went to. I just love P scotch. and so they got me like private tours. So I can like take notes in such. and they gave me a free accommodation that I was like, I want to be really clear about this.I’m not mentioning this place. And they’re like, just, just take it. And so, and I didn’t mention it and I didn’t mention that, you know, I got access to these, you know, distillers to ask some questions, but it was more about building this article as a journalist than,Hey, I want like free tours, you know, like, I mean, I saved 20 bucks. Right. But the point was, I wanted to learn about the process to write about this story beam. And then they offered me free flights and stuff. It was like, now I just, I just want the tourist, please. Thanks.[00:32:44] Nathan:Yeah, it’s interesting of the, what a lot of people would view as the perks to get into travel blogging. Right. I want to get into it because then I’d have these free chips or I can have these offs or whatever else, I guess the right apps you get, no matter what, but, You know that that’s the other side of like, everything comes with a cost.And I think it’s important to realize what you’re doing because you want to versus what you’re doing, because now you feel obligated because someone gave you something for free.[00:33:12] Matthew:Yeah. The most thing is I tend to accept our city tourism part, which gets you like free access to museums and stuff. I was like, okay, that’s cool.But beyond that, I just, you know, I don’t want to get into, like, you want to give me a museum pass. I’m going to see these museums anyway. Sure. I’ll save some money and I’ll, I’ll make a wheel note, but I’m going to no obligation to write about which museum, because I write about the ones I like anyway.So,[00:33:39] Nathan:Right.[00:33:40] Matthew:You know, that’s not to me like free travel. That’s not what people think of Like the perks of. the job are.[00:33:46] Nathan:I, that was funny. When I learned about the, like the welcome packet that cities will, will give, like the first time I saw it in action was. I went to Chris, Guillebeau’s like end of the world party in Norway. and I was hanging out with Benny Lewis there who runs, you know, fluent in three months, a mutual friend of both of ours.You’ve known him longer than I have, but like, we’re both at our check into the hotel and he’s got like this whole thing of all these museum passes he’s got, and he’s just like, yeah, I just emailed the tourism board and said, I was going to say, and they’re like, oh, blogger. And they gave him like, you know, access to everything and you only ended up using half of it because we weren’t there for that long, but,[00:34:28] Matthew:Yeah. That’s great. You should always get these discount cards, like the comparison museum pass or the New York mic go card that will save you a lot of money if you’re doing lots of heavy sites in.[00:34:39] Nathan:Yeah. Yeah, for sure. okay. So how does actually let’s dive into the COVID side, right? Cause COVID took a hit huge hit on the entire traveling. we saw that just in the like running ConvertKit where, you know, having bloggers in so many different areas, we had a lot of growth because lots of people were stuck at home and start like, I’m going to start a new blog.I’m going to have time to, to work on this or whatever. And it was a lot of cancellations, mostly from the travel industry. If people like, look now that what this 50,000 person list, that was a huge asset is now just a giant liability. because no one’s planning trips. How did you navigate that time? And what, like, what’s the journey been?You know, the last 18 months, two years,[00:35:28] Matthew:Well first I would say that’s really shortsighted of someone canceling their 50,000 person list like[00:35:34] Nathan:I think they were like exporting sitting on it and they’re going to come back. But, but I agree. It was very shortsighted.[00:35:39] Matthew:Yeah. Like just like throw it away. 50,000 emails, right. I mean, it was tough in the beginning. You know, we went from like January and February were like best months ever, you know? And like, I mean, even, and then all of a sudden like, like March 13th is like that Friday, you know, it’s like everything crashes, like again, like we were on our way to have a banner year, like, like, like hand over fist money, you know?And, and then to being like, how am I going to pay the bills? You know? and so, cause you know, we, haven’t sort of the, the overhang from Java con, right. You know, like we didn’t make money on the first two years. And year three was the, the breakeven year and travel con was in, Right in the world ended in March.Right. And so I had laid out all, like, you’re so close to the event, that’s you? That’s when you start paying your bills. Right. And the world hits and all the sponsors who, you know, have their money, you know, in the accounting department are like, oh, we’re not paying this now. And so you’re like, well, I’ve just paid $80,000 in deposits and all that money that was going to offset.It has gone. and then you have people canceling. A lot of people were really mean about it. They’re like, oh, I’m, I’m back now. And we’re going to do charge backs, that, you know, you have that overhang and just, you know, fall in revenue it’s it was really tough. thank God for government loans, to be quite honest, like I, I went to native through if it wasn’t for, all that, because a lot of my.My money was tied up in non-liquid assets. So it wasn’t like I could just like sell some socks though, you know, pay the bills. but things have come back a lot. I mean, there’s a lot of paint up the man, for travel, I view it like this way, right? You got kids, right. You know, they get in trouble, you take away their toy and then you give them back.Right. Where do they want to do now? They just want to play with that toy even more because it’s like, no, it’s mine. No one else can have it. And like where you want to do this other toy. No. And so now that the toy of travel is being given back to people like people are like, never again, am I going to miss out on this opportunity to travel on my dream trips?Let’s make it happen. So we had a really good summer. I spoke to mediocre fall and winter just as the kids are back in school, people are traveling less, you know, but as more in the world, that? will be good. but again, as I said, at the beginning of this, it’s going to take awhile for us to get, to get back to where we were, but there’s definitely demand there,[00:38:36] Nathan:When’s the next conference when the travel con happening again.[00:38:39] Matthew:April 29th,[00:38:41] Nathan:Okay.[00:38:41] Matthew:22,[00:38:42] Nathan:So what’s the how of ticket sales benefit for that? Is there like that pent-up demand showing up and people booking conference tickets or are they kind of like, wait and see, you know, you’re not going to cancel this one too kind of thing.[00:38:55] Matthew:Yeah, I mean, we’re definitely not canceling it. I mean, the world would have to really end for it. We just launched, this week. So, early October, we just announced our first round of speakers. and we sold like 10 or 15 tickets. I don’t expect a lot of people, to buy until the new year I saw this.And the old event, right? Because in the old event we were had in May, 2019. Right. And we announced in the fall, but it wasn’t until like, you know, a few months prior that people started buy their ticket. Right. Because they don’t know where they’re going to be. You know, where are they flying from? What were the COVID rules going to be like, the demand is there.But I, I know people are probably just waiting and seats for their own schedule too, you know? So, but you were against so 800 tickets and honestly, from what I’ve heard from other events, you know, people are selling out, you know, because there was such demand, like it’s not a problem of selling the tickets, so I’m not sure.[00:40:01] Nathan:Yeah, one thing, this is just a question that I’m curious for myself. since I also run a conference, what do you think about conferences that rotate cities or like Mo you know, move from city to city, which we’ve been to a lot of them that do it. You know, the fin con podcast movement areTwo longer running ones that you and I have both been to. obviously that’s what you’re doing. The travel column. well, domination summit, which we’ve both been to a lot, you know, it was like very much it’s Portland. It’s always Portland. We’ll never be anywhere anywhere else. What do you think, why did you chose? Why did you choose the approach that you did in what you think the pros and cons are?[00:40:39] Matthew:Yeah, for, for me it was, you know, we’re in travel. I wanted to travel. Right. And plus, you know, I mean, you get up, we get a host, right? So like Memphis is our sponsor. Right. It’s in Memphis. Yeah, it was supposed to be in new Orleans. New Orleans was our host sponsor. Right. So moving it from city to city allows us to get, you know, a new host sponsor every year is going to pony up a bunch of money.Right. I don’t know how Podcast move into it, but I think if I wasn’t in travel and it was more something like traffic and conversion, or maybe we’ll domination summit, I would probably do it in the same place over and over again because you get better consistency. you know, one of the things I hate about events is that they move dates and move locations.Right. And, and so it’s a little hard to in travel cause you know, COVID really screwed us. Right. But we’re moving to being, you know, in the same timeframe, right. We’re always going to be in early May. That’s where I want to fall into like early may travel car, change the city, but you got the same two-week window, because it’s hard to plan, right?So like if you’re changing dates in cities, you’re, you’re just off of a year. So I wanted some consistency, make it easier for people to know, like in their calendar, Java con early Mac, Java con, early Mac, you[00:42:17] Nathan:Yep.[00:42:18] Matthew:It doesn’t really work out cause of COVID, but post COVID we’re we’re moving to that, that, early may[00:42:24] Nathan:Yeah. Okay. So let’s talk more about sort of scaling different between different levels of the business. So there’s a lot of people who say, all right, 10, 20, 50,000 subscribers, somewhere in there. And it’s very much the solopreneur of like, this is, I’m a writer. I just do this myself. Or maybe they, you know, contract out graphic design or a little bit more than that.What were some of the hardest things for you and why and what worked and what didn’t when you made the switch from it being nomadic, Matt being just Matt to Matt plus a team.[00:43:00] Matthew:Yeah, it It’s definitely hard to give up that control, right. Because you always think no one can do your business better than you can. And I mean, even to this day, I still have issues doing, you know, giving up control. Right.[00:43:14] Nathan:What’s something that you don’t want to, that you’re like still holding onto that, you know, you need to let go of[00:43:19] Matthew:Probably just little things like checking in on people and, you know, Content probably like Content. I’m very specific about my voice, the voice we have. So. But I should let my content, people make the content that I know is fine. but I definitely, probably overly check on my teams to be like, what’d you do today?You know, you know, that kind of stuff. but I did take a vacation recently and I went offline for a week and they didn’t run the thing down. So I was like, oh right. That was my like, okay, I can, I can let go. And it’s going to be okay. But, so getting comfortable with that much earlier on, I would probably save you a lot of stress and anxiety.I definitely think you should move to at least having somebody, you know, a part-time VA, if you’re making over six figures, hire somebody because you know, how are you are not going to go from a 100k to 500k really by yourself? Unless, you know, you just have some crazy funnel that you do, but even the people I know who are solopreneurs, they still have two or three people helping them a little bit part, even if it’s just part-time because the more money you make, the more time you have to spend keeping that income up.And so your goal as the creator in the owner should be, how can I grow? How can I make more money? It should not be setting up your WordPress blog. You know, It should not be answering joke emails It should not be, you know, scheduling your social media on Hootsuite, that kind of low level stuff can be done by, you know, a part-time VA And maybe that part-time VA becomes a full-time VA as you scale up more. But you know, if you, you have to free up your time and you’re never going to free up your time, if you’re spending a lot of that time, scheduling. So you mean that the people I know who have half a million dollar businesses, selling courses, you know, and they’re really just a solopreneur.They have somebody do that grunt work, right. Plus if you’re making that much money, is that the best use of your time now? Really? Right. So getting somebody to do sort of the admin front work, as soon as you can, even if it’s on a part-time basis will allow you to focus on growth marketing, and monetization, which is where you should be like Podcast.This week. I have like four or five podcasts I’m doing, right. You know, that is a good chunk of my week. If I have to spend that time scheduling on social media, you know, or setting up blog posts, like I can do that. And this is where the growth in the audience comes in.[00:46:12] Nathan:Okay. So since we’re talking about growth, what are the things that you can tie to the effort that you put in that drives growth? Are there direct things or is it a very indirect unattributable[00:46:27] Matthew:Yeah, I think there’s some direct things like, you know, before, you know, asking 10 years ago, I would say guest posting on websites. Right. You write a guest post on like Confederacy’s site and boom, tons of traffic. Right. that doesn’t exist anymore. I mean, yeah. You can get a lot of traffic, but it’s not like the huge windfall it used to be, but it’s still good for brand awareness.SEO. Great for links. Right. I would say things today that I can tie directly to stuff Podcast and, Instagram. So doing, like, doing a joint Instagram live with another creator. Right. You know, like me and, you know, it’s I know pat. because someone with a big following there, we do, we do a talk, you know, 30 minutes, you know, I can see in my analytics, like a huge spike in my following right after that.And so that’s a great way to sort of grow your audience is to do Instagram collabs in just like 30 minutes tops and[00:47:32] Nathan:Podcasts[00:47:33] Matthew:I get a lot of people will be like, I saw you on this podcast. I was like, wow, cool.[00:47:37] Nathan:I always struggle with that of like, of all the activities that you can do. Cause you get to a point where there’s just so many opportunities open to you and it’s like, which are the best use of time. What should you say yes to, what should you say no to, and I don’t know. Do you have a filter along those or do you just, is it just kind of gut-feel[00:47:53] Matthew:I will say yes to any text-based interview, normally it is the same questions over and over again. So I sort of have a lot of canned responses that I can just kind of paste. and tweak But those are links, so I’m like, sure. Yeah. Send your questions over. Cut paste, tweak, you know, you know,[00:48:12] Nathan:Customize[00:48:13] Matthew:Customize a little bit, but you know, how many times do I need to rewrite from scratch?How’d you get into blogging, you know, what’s your favorite country, Podcasts I definitely have a bigger filter on like you, I don’t do new podcasts.[00:48:27] Nathan:Okay.[00:48:27] Matthew:I know that’s like bad. because you know, this new podcast could become the next big thing, but come back to me when you have some following.[00:48:36] Nathan:I like Seth, Godin’s rule I’m not on south Dakotan’s level by any means, but he says like, come back to me. When you have 100 episodes, I will happily be your 100th interview on your podcast or something[00:48:47] Matthew:Yeah.[00:48:48] Nathan:And he’s just like, look, Put in your time and then we’ll talk.[00:48:51] Matthew:Yeah, so I like, I don’t look for just following, but like again, you know, knowing that people give up on blogs, people give up Podcast too. So. You know, you have to have been doing it for like six months a year, like week a weekly, you know? So I know like this something you care about. and I like to listen because you know, you get a lot of new people and they’re not really great.You know, they asked us like a lot of canned questions and you’re like, listen, you’re taking, you know, an hour, hour and a half of my time. You gotta make it interesting for me.Well, yeah, Podcast. And then for Instagram stories you gotta have, or Instagram lives, either a brand new audience, or if you’re in travel, at least 75,000.Cause I have like a one 30, so I want to keep it in the same in a level.[00:49:43] Nathan:Yeah.I know nothing about Instagram and promotions on Instagram and all of that is there. If someone were to, like, in my case, if I came to you and say, Hey, I want to grow my Instagram following. I’ve got 3000 people or 5,000 people or something like that. And I want to be have 50,000 a year from now.Where would you point me?[00:50:05] Matthew:I would say, do you join Instagram lives with people like once a week, you know, and just, or maybe once a week for you and then go to somebody else on their side once a week. So, and just kind of work your way up, like find people in your, your sort of follower count level, you know? So in this case, I’d probably do, you know, you know, 1000 to 5,000, I would look for in your niche and like get online for 30 minutes and talk about whatever it is you want to talk about and and then go to someone else’s channel and do that, and then keep doing that because you’ll just see giant spikes and then you can move up the the ladder.Then you have 10,000 followers and someone with 25,000 followers might give you the time of day. And then you talk about that, you know, and you just sort of build awareness because you’re always there. You’re always around.[00:51:03] Nathan:It’s a really good point about the figuring out what those rough bands are and reaching out within those. Because I think a lot of people are like, I’m going to go pitch whoever on doing Instagram live together. And it’s like, you have 5,000 and they have 150,000. And like the content might be a perfect fit, but they’re most likely going to say no, because you’re not[00:51:24] Matthew:Yeah.[00:51:24] Nathan:Driving that much value for, or that many subscribers for their audience.[00:51:29] Matthew:Yeah. You know, and so you, maybe I would, you know, someone was like a finance blogger, and they had like 40,000, 30, 40,000. I’d probably.We do it because people who like to say money, like say money on travel. So it’d be like, there’s probably a good fit. And you know, 30,000 people, they might not know me or they have like, like you said, 3000, come back to me, you know, when there’s another zero,[00:51:57] Nathan:Right. Well, and then the other thing that’s going to be true is if I’m bringing you to, to my audience to share and teach something, if you’re using this strategy, like go do another 20 of these or 50 of these, and your pitch will be better. And the way that you teach finance to travel bloggers or whatever else it is, is going to get so much better.[00:52:17] Matthew:Yeah,[00:52:18] Nathan:It’s like, I kind of don’t want to be your Guinea pig. You know, I don’t want my audience to be your Guinea[00:52:23] Matthew:Yeah,[00:52:24] Nathan:Pig for your content. And so just get more experienced and come back.[00:52:28] Matthew:Yeah. And you know, you also gotta think about, you know, people are so time-starved right. You know, when I started blogging, I could. There was no Instagram. There was no Snapchat. There was no Tech-Talk, you know, Twitter was barely a thing. So I didn’t have to split my focus on so many different platforms and channels.Right. I can just, alright, I can be on this one blog, but now when people are like, whoa, sorry, I have to like manage all these different social channels and all of these comments in the blog and everything. They not don’t have like an hour to give, you know, to just anybody way do you could have before,[00:53:12] Nathan:Yeah. Yeah. That’s so true. Okay. So on the email side, specifically, if someone came to you with say 1,000 newsletter subscribers today, and they’re like, I want to grow, I mean, you’re looking to grow to 5,000. This might be so far removed from where you’re at that you’re like, I don’t even know if that was, you know, a decade ago that I was in that position, but what are you seeing that’s working?Where would you point them?[00:53:33] Matthew:What works for us right now? one having email forms everywhere on your site, sidebar, footer, we have one below the content below the content forms, and popups, popups, the work they’re really great. we find for really long posts, having a form in the middle of the post converts better than, at the end of the post, because know a A lot of people don’t read to the end, but when they get to in the middle you’re still there.You know, if you look at heat maps are really long websites, right? You just see that drop-off right. So if all your forms are at the bottom of the page, they’re just not getting the visibility, that you need. so middle of the page,[00:54:19] Nathan:Do you play with a lot of different incentives of like, you know, Opt-in for this fee guide, you know, or are you customizing it to something for a particular country or there, the content that they’re reading[00:54:30] Matthew:Yeah, so we use OptinMonster for that. and so we have, like, if If you go to our pages that are tagged Europe, you get a whole different set of options. than if you go to Australia, like, and like the incentives are like, you know, best hostels in Europe, you know, best hostels in Australia, right? Like little checklist guides.And I tweak what the copy for that, you know, just to see what wording, will lift up a better conversion rate. But yeah, we definitely, because, you know, we cover so many geographic areas. The needs of someone going to Europe are a little different than somebody going to New Zealand. So we, we definitely customize that kind of messaging. And I think that helps a lot, you know, and definitely customizing messaging as much as possible. Um know, but in terms of just, you know, we can talk about, you know, the market, like how do you word things, but middle pop-ups and mil of blog posts definitely converts the best. And so like that’s where we see a lot of growth, as well as, just on Instagram telling people to sign up for my newsletter or Twitter or Facebook, but don’t let the algorithm, you know, keep you from your travel tips, sign up now and people do.[00:55:58] Nathan:Okay. And is that like swipe up on stories that you’re doing[00:56:02] Matthew:Yeah.[00:56:03] Nathan:You know, on an Instagram live or all the above?[00:56:06] Matthew:All the above.[00:56:07] Nathan:Yeah.[00:56:07] Matthew:You just constantly reminding people to sign up for the list, you know, and. One of the failings of so many important for influencers today is, you know,They always regret everyone as everyone does. They always regret not starting to list, you know? And so, you know, you just got to hammer into people, sign up for the list, sign up for the list, sign up for the list.Yeah. And a lot of the copy is, do you see all my updates? No. Would you like to sign up for this newsletter?[00:56:39] Nathan:Yeah, because everyone knows. I mean, I come across people all the time. It’s like, I used to follow them on Instagram. I haven’t seen, oh no, I do still follow them on Instagram. Instagram just decided that I apparently didn’t engage with their content enough or something.[00:56:53] Matthew:Yeah,[00:56:54] Nathan:So now I no longer see their posts,[00:56:56] Matthew:Yeah. You like, I go, I always go to my like 50 least interacted profiles. Right. And, you know, there are some people that aren’t there. I interact with this guy all the time. How is this the least attractive? But that that’s Instagram and saying, here are the people we don’t show you in your feet.[00:57:13] Nathan:W where do you see that? Is that[00:57:16] Matthew:If you go to your, who you’re following, it’s it should be up on the top.[00:57:20] Nathan:Hmm. All right. I’ll have to look at that.[00:57:22] Matthew:Yeah. I’ll send you a screenshot. and so like, that’s the algorithm be like, here are the people who you interact with the least, but it’s like, no, I, I love their stuff. why why do it take them from me? So,[00:57:36] Nathan:Zuckerberg is like, do you really love their stuff? I just not feeling it.[00:57:40] Matthew:Yeah, yeah, yeah. And so, yeah, it’s just, you know, the algorithms are terrible and what I hate and I learned this last year, and this was sort of a unsurprising, but surprising thing is that stories, which used to be like the latest first.[00:57:59] Nathan:Yeah.[00:57:59] Matthew:That is, they have an algorithm for that now, too. And I was like, I, I shouldn’t be surprised, but I am surprised.And I’m annoyed by that because like, I liked it when it was just the newest first, but Nope, now that is based on, you know, sort of like Tik TOK thing of like, oh, this story is getting really a lot of interactions. We’ll bring it up the front of people’s queue or, you know, so it’s not just like your first, because you had one, one second ago, you know, like it could, it’s based on an algorithm[00:58:35] Nathan:Yeah.And that’s how it’s all going to go. Facebook did that a lot, you know, with Facebook fan pages back in the day where it used to be fantastic for engagement. And then they were like, yeah, it’s fantastic. If you pay us[00:58:46] Matthew:Yeah. And even then it’s like, I would pay to boost posts. I was like, great. You saw, I lectured five people. What? I just gave you a hundred bucks and that was. And there was some guy you remember him commenting last year. He was like, whatever happened to this page? I was like, I’m still here. He’s like, no, no, no, no.And this isn’t a common thread in Facebook. He’s like your pages to get a lot more engagement. What happened? I was like, oh, Facebook algorithm. I was like, people just don’t see it. Let me tell you where all my analytics side it’s like this page. So I have 2000 people. You’re like great. 1%, woo[00:59:23] Nathan:Do you do paid advertising? I’d like to get email subscribers.[00:59:28] Matthew:We used to, but, the CPMs went up so much that it wasn’t worth the effort. You know, like paying a dollar 52 bucks for an email subscriber, is just a lot of money for, for, for things. We don’t mind ties directly. Like we’re not taking people through finals buy a course, right? Like just to get rot email, I’m not paying two bucks for.Yeah. And, and so I just, we stopped paying, like during the pandemic, like, June, June of last year, we were like, oh, we’re going to take a break. And then we paid somebody to help us for it to make kind of reset it up. But I just had to spend down so much. I was like, you know what, I’m going to turn off for a bit.And yeah, that’s been like,[01:00:17] Nathan:Didn’t really miss it.[01:00:18] Matthew:Yeah, I looked at the numbers recently cause I was thinking, should we do it? And it’s not that big of a difference of just doing it organically on like Instagram stories or just on the page. Right. And I also don’t really like giving money to the Zuckerberg empire of VO. I just not a fan of that business.And so like, I know my ad spend is low, but I can’t say just. On a rod number. Like it wasn’t that big of a deal. Like, you know, like, cause the CPMs were so high, we were having to pay a lot of money. So like we put in like two grand a month and we weren’t getting thousands. We getting hundreds of people, you know, I want four for two grand.I want thousands of people.[01:01:06] Nathan:Yeah. For my local newsletter, we’re doing paid advertising on Facebook and Instagram and averaging about $2 per subscriber. And that I think now that’s considered pretty good. You’d like a lot of, with a broader audience, you’d be at $3 or more per subscriber and it gets expensive pretty fast.[01:01:23] Matthew:Yeah. I mean, but I think at some point you’ll just see such diminishing returns that, you know, I mean, how many people are in Boise, can you hit, you know, over and over again?Right.[01:01:35] Nathan:Yep.[01:01:36] Matthew:I, I was just reading Seth Godin’s book. This is Marketing. And he said, you know, they talked about ads.You turned off ads when the Content says turn ‘em off. And my Content, I was like, you know, they’re not really paying for themselves.[01:01:50] Nathan:Yeah. Let’s see. Yeah. You turn that off. Looking forward, maybe like two or three years is that I think your business has fascinating of the approach that you have of taking an online audience, building a real team around it, and then building it into the in-person community. what do you think the business is going to look like in two, three years?Where, where is revenue coming from? What’s your vision for the events and meetups and what are the things that like over that time period, they get really excited.[01:02:19] Matthew:Yeah. Two, three years. So we’re talking, you know, 20 by 20, 23, most of our revenue coming from stuff in person, you know, having chapters around the world, people pay to go to them. So, you know, it it’s like 10 bucks and you can bring your friends for free, right. So it’s like five bucks versus. Just for the cost of like hosting events.Right. doing lots of that, doing tours, we’re bringing back. and they won’t be just with me cause they’re community events. Right. So we’ll have guides, right. So it’s not just, you’re coming to travel with me, sort of what Rick, Steve does. Right. You go on and Rick Steves tour, it’s his itinerary, but he’s not on the tour.Right. He shows up to a couple of them throughout the season when it’s not like you don’t expect him to be your guide at the time. So moving to that, having a consumer event for like, like a, like a world domination summit, you know, a weekend somewhere just for travel consumers, having an app for both having an app for that company. then online just being a lot of and affiliates and you know, even me. Just even taking away just having this like passive income course, just because, you know, one less thing to worry about. Right.And then travel con, so being around, but actually making money this time.[01:03:47] Nathan:Do you think travel con is going to turn into, I mean, obviously it’s a significant amount of revenue, but the expenses are so high. Do you think it will turn into a profitable business[01:03:56] Matthew:Oh yeah. Yeah. Like, I mean, a lot of the unprofitability is just comes from the fact that I had no idea where that was doing.[01:04:02] Nathan:Yeah, I know that firsthand from my own conference, so yeah.[01:04:07] Matthew:It was, I didn’t realize how quickly expenses gets that. Right. You know, being like, oh, okay. Like my food and beverage budget is 120,000 writing that in there. And then getting $145,000 bill because, oh yeah, it’s 120,000 food, but then there’s tax fees, which we, you know, all this stuff and like, Okay, well, that’s $25,000 off the profit.Right. and so with a better handle of expenses, like we were definitely like this year, we were gonna like reg even, you know, at the very minimum, we’ll pre COVID and this year we’ll also break break event. Um it’s and just keeping a handle on, you know, like, well, how will I don’t invite a hundred speakers, you know?And, and be like, oh, I had planned to only budget, you know, 50,000 speaker fees, but now I’m at 80. Okay. Like, handling the cost better. We’re good. Now I have a professional events team that kind of slaps me around and it’s like, can’t spend that money.[01:05:06] Nathan:I know how it is, where I’m like, Hey, what if, and then just like, now[01:05:10] Matthew:Yeah,[01:05:10] Nathan:Love it, but no,[01:05:12] Matthew:Yeah,[01:05:12] Nathan:Don’t like, you don’t have the budget for it.[01:05:15] Matthew:Yeah. But no, I mean, you know, we used to have a party. And we’re getting rid of the second night party because people don’t want to go. Like we didn’t have a lot of people show up cause like they’re out and about on town. So it’s like, wow, I just spent, you know, $40,000 for like a third of the conference to come, you know, why not take that money and use it to something that’s more valuable for everybody that has more like impact for dollar spent and still not like go over budget.You know, same thing with lunches. We got, we were getting rid of, we’re doing one lunch now.You know, cause people don’t really care that much, you know, about in[01:06:01] Nathan:Yeah, it’s super interesting.Well, I love the vision of where the conference is going, and particularly just the way that the whole community interplays. I think it’s been fun watching you figure out what you want your business model to be, because obviously, with a large audience, your business model can be any one of a hundred different variations.I like that you keep iterating on it, and figuring out the community.[01:06:26] Matthew:Yeah, we’re definitely going in-person. We’re definitely going to expand to colleges. So, taking the meetup and doing a presentation to a local student union. Because you got to keep people in the grind, right? Keep feeding the grind. So, college students love saving money.We are experts at that. They love to travel. So, just giving a presentation to college campuses around the world as a way to expose them to our brand, and get them to our local event. Like, “Hey college students in Boston, do you like this event? Well, we have a local chapter here. Come join us.”[01:07:08] Nathan:Right. Yeah.[01:07:10] Matthew:They sign up for that, and they get my email.[01:07:13] Nathan:I like it.Well, if anyone wants to sign up and follow along, and all of that, where should they go to see the Instagrams, and subscribe to the newsletter, and everything else?[01:07:22] Matthew:Yeah. You can find me at NomadicMatt.com. The community website is, TheNomadicNetwork.com, and @NomadicMatt on every social media platform.[01:07:32] Nathan:That’s the good thing about finding something somewhat unique, and doing it nice and early.[01:07:37] Matthew:Yeah.[01:07:38] Nathan:You can claim it, rather than being “The” whatever, at underscore something.[01:07:43] Matthew:Yeah. I mean, it also helps having an established brand and the trademark, because if someone took my name on TikTok, and I was just like, “Nope, TikTok.” And they’re like, “Okay, it’s now yours.”[01:07:54] Nathan:There you go. Yep. That’s a good way to go.Well, man, thanks for hanging out today, and I’ll catch you later.[01:07:58] Matthew:Yeah. Thanks for having me.

Andrew Warner has been part of the internet startup scene since 1997. Andrew and his brother built a $30 million per year online business, which they later sold. After taking an extended vacation and doing some traveling, Andrew started Mixergy. Mixergy helps ambitious upstarts learn from some of the most successful people in business.Andrew and I talk about his new book, Stop Asking Questions. It’s a great read on leading dynamic interviews, and learning anything from anyone. We also talk about longevity and burnout as an entrepreneur. Andrew gives me feedback about my interviewing style, the direction I should take the podcast, and much more.In this episode, you’ll learn: Why you need to understand and communicate your mission How to get your guest excited about being interviewed What to do instead of asking questions How to hook your audience and keep them engaged Links & Resources ConvertKit Gregg Spiridellis JibJab Ali Abdaal The Web App Challenge: From Zero to $5,000/month In 6 Months Groove Zendesk Help Scout Jordan Harbinger Noah Kagan Bob Hiler Seth Godin Morning Brew Alex Lieberman Keap (formerly Infusionsoft) Notion Sahil Bloom Ryan Holiday Brent Underwood Ghost Town Living Trust Me, I'm Lying: Confessions of a Media Manipulator Damn Gravity Paul Graham Y Combinator Nathan Barry: Authority Ira Glass NPR This American Life Barbara Walters Richard Nixon interview Oprah interview with Lance Armstrong Matt Mullenweg Chris Pearson Conspiracy: Peter Thiel, Hulk Hogan, Gawker, and the Anatomy of Intrigue Peter Thiel Gawker Nick Denton The Wall Street Journal Rohit Sharma SanDisk Jason Calacanis Dickie Bush Sean McCabe Daily Content Machine Jordan Peterson Tribes Warren Buffet Sam Walton Ted Turner GothamChess LinkedIn Learning (formerly Lynda.com) Inc.com: Selling Your Company When You're Running on Fumes Chess.com Mark Cuban James Altucher Rod Drury Andrew Warner’s Links Andrew Warner Stop Asking Questions Mixergy Episode Transcript[00:00:00] Andrew:The top 10 interviews of all time are news-based interviews. We, as podcasters, keep thinking, “How do I get enough in the can, so if I die tomorrow, there’s enough interviews to last for a month, so I can be consistent, and the audience loves me.”That’s great, but I think we should also be open to what’s going on in the world today. Let’s go talk to that person today. If there’s an artist who’s suddenly done something, we should go ask to do an interview with them.[00:00:32] Nathan:In this episode, I talk to my friend, Andrew Warner, who I’ve known for a long time. He actually played a really crucial role in the ConvertKit story in the early days, and provided some great encouragement along the way to help me continue the company, and get through some tough spots.We actually don’t get into that in this episode, but it takes an interesting turn because we just dive right in.Andrew’s got a book on interviewing. He runs Mixergy. He’s been, running Mixergy for a long time. We talk about longevity and burnout, and a bunch of other things. He dives in and challenges me, and gives me feedback on my interviewing style. Where I should take the Podcast, and a bunch of other stuff. It’s more of a casual conversation than the back-and-forth interview of how he grew his business. But I think you’ll like it. It’s a lot of what I’m going for on the show.So anyway, enjoy the episode.Andrew, welcome to the show.[00:01:25] Andrew:Thanks for having me on.[00:01:26] Nathan:There’s all kinds of things we can talk about today, but I want to start with the new book that you got coming out.This is actually slightly intimidating; I am interviewing someone who has a book coming out about how to be good at interviewing. Where do we even go from here? You were saying that you have thoughts?[00:01:47] Andrew:I have feedback for you. I have a thoughts on your program.[00:01:51] Nathan:I’m now even more nervous.[00:01:52] Andrew:I’ve been listening, and I’ve been following, and I’ve been looking for questioning styles. Is there feedback I could give him? I mean, I’ve wrote a whole book on it. I should have tons of ideas on that.I don’t. Here’s the thing that stood out for me watching you. There’s an ease and a comfort with these guests, but I’m trying to figure out what you’re trying to do with the Podcast. What is connecting them? Are you trying to bring me, the listener, in and teach me how to become a better creator who’s going to grow an audience and make a career out of it? Or are you trying to learn for yourself what to do?How to become closer to what Ali Abdaal doing, for example, or Sahil Bloom? Are you trying to do what they did, and grow your audience? Or is it a combination of the two?I think the lack of that focus makes me feel a little untethered, and I know that being untethered and going raw, and letting it go anywhere is fine, but I think it would be helpful if you gave me a mission.What’s the mission that Nathan Barry’s on with the Podcast. Why is he doing these interviews?[00:02:56] Nathan:Oh, that’s interesting. Because it’s probably different: my mission, versus the audience members’ mission.[00:03:05] Andrew:I think you should have a boat together and, but go ahead.[00:03:08] Nathan:I was going to say mine is to meet interesting people. Like that’s the thing I found that, podcasts are the pressure from two sides, one as a creator, as an individual online, like I’m not going to set aside the time to be like, you know what, I’m going to meet one interesting person a week and we’re just going to have a conversation riff on something like that.Doesn’t happen the times that, you know, the years that I didn’t do this show, I didn’t set aside like deliberate time to do that. And then the other thing is if I were to set aside that time and send out that email, I think a lot of people would be like, I kind of had to have a busy week. I don’t know that I’ve, you know, like yeah, sure.Nathan, whoever you are. I did a Google search. You seem moderately interesting. I’m not sure that I want to get on that.Like a, get to know[00:03:58] Andrew:They wouldn’t and it would be awkward. And you’re right. The Podcast gives you an excuse. I think you should go higher level with it though. I think you should go deep to the point where you feel vulnerable. I think what you should do is say something like this, isn’t it. You have to go into your own into your own mission and say, this is what it is.And just, so let me set the context for why this matters. I think it helps the audience know, but it also helps you get better guests to give better of themselves. I talk in the book about how I was interviewing Greg spirit, Dallas, the guy who created jib, jab, you know, those old viral video, it was a fire video factory that also created apps that allowed you to turn your yourself into like a viral meme that you could then send to your friends.Anyway, he didn’t know me. He was incredibly successful. He was, I think, person of the year, a company of the year named by time. He was on the tonight show because he created these videos that had gone viral. And yes. He said yes, because a friend of a friend invited him, but I could see that he was just kind of slouching.He was wearing a baseball cap. It wasn’t a good position. And then he said, why are we doing this? And I said, I want to do a story. That’s so important. That tells the story of how you built your business. Yes. For my audience. So they see how new businesses are being built online, but let’s make it so clear about what you did, that your great grandkids can listen to this.And then they will know how to great grandfather do this and put us in this situation. And that’s what I wanted. I wanted for him to create that. And he told me that afterwards, if he had known that that was a mission, he wouldn’t have put his hat on. He said that after that, he started thinking about the business in a more in depth way, visualizing his great grandchild.And then later on, he asked me for that recording so that he could have it in his family collection. So the reason I say that is I want us to have a mission. That’s that important that yes. You could get somebody to sit in front of the camera because you’re telling me you’re doing a podcast, frankly.Right. You’re with ConvertKit they’re going to say yes, but how do you bring the best out of them? And that’s it. And so that’s why I’m doing this. And so one suggestion for you is to say something like.I’m Nathan, I’ve been a creator my whole life, but I’m starting from scratch right now with YouTube.I’ve got 435 people watching YouTube. It’s not terrible, but it’s clearly not where I want to end up. And so what I’ve decided to do is instead of saying, I’ve created the book authority, I wrote it. I’m the one who created software that all these creators are using a ConvertKit. Instead of, instead of allowing myself to have the comfort of all my past successes, I’m going to have the discomfort of saying, I don’t know what it’s like.And so I’m going to bring on all these people who, because maybe I’ve got credibility from ConvertKit are going to do interviews with me. And they’re going to teach me like Alia doll and others are going to teach me how they became better creators, better business people. I’m going to use it to inform my, my, growth on YouTube.And by the way, You’ll all get to follow along. And if you want to follow along and build along with me, this is going to come from an earnest place. Now I’ve obviously gone. Long-winded cause I’m kind of riffing here, but that’s a mission. And now we’re watching as you go from four to 500, now we care about your growth.Now there’s someone giving you feedback and more importantly, there’s someone who then can go back years later and see the breadcrumbs. Even if the whole thing fails and say, you know what?Nathan made it in virtual reality videos. And he’s amazing. But look at what he did when YouTube was there. He clearly didn’t do it, but he aspired right. I could aspire to, if I don’t do it, I’ll do it in the next level. That’s that’s what I’m going for with it. I talk too much sometimes and give people too much, too much feedback. How does that sit with you?[00:07:14] Nathan:I like the idea. I particularly love anytime a creator’s going on a journey and inviting people along for it, right. When you’re sitting there and giving advice or whatever else, it’s just not that compelling to follow it unless there’s a destination in mind. So I did that with ConvertKit in the early days of, I said, like I called it the web app challenge said, I’m trying to grow it from zero to 5,000 a month in recurring revenue.Within six months, I’m going to like live blog, the whole thing. people love that another example would be also in the SAS space, but, the company grew, they did a customer support software and they, I think. They were going from 25,000 a month to 500,000 a month was their goal. and they even have like, in their opt-in form, as they blogged and shared all the lessons, it had like a progress bar.You’d see, like MRR was at 40,000,[00:08:08] Andrew:Every time you read a blog post, you see the MRR and the reason that you don’t remember what the number was is I believe that they changed it, you know, as they achieve the goal, they, they changed it to show the next goal on their list. And yeah, and you’ve got to follow along now. Why do I care? The groove, HQ or groove is, is growing a competitor to Zendesk and help scout.But now that I’m following along, I’m kind of invested now that I see how they’re writing about their progress. I really do care. And by the way, what is this groove and why is it better than help scout and the others? Yeah. I agree with you. I think that makes a lot of sense. I think in conversations also, it makes a lot of sense.I think a lot of people will come to me and say, Andrew, can I just ask you for some feedback? I’m a student. Can I ask you for support? It’s helpful for them to ask, but if they could ground me in the purpose, if you could say to somebody I’m coming to you with these questions, because this is where I’m trying to go, it changes the way that they react.It makes them also feel more on onboard with the mission. I have a sense that there is one, I’m just saying nail it, you know, who does it really good? who does a great job with it is a Jordan harbinger. He starts out his each episode is almost if you’re a fan of his, it’s almost like enough already. I get that.You’re going to do an opt-in in the beginning of the Podcast. I get that. What you’re trying to do is show us how to whatever network now and become better people. But it’s fine. I’d much rather people say, I know too much about what this mission is. Then I don’t.[00:09:26] Nathan:Do you who’s afraid anyone else tuning in? What, what is Jordan’s mission? What would he say is the mission that[00:09:32] Andrew:It’s about, see, that’s the other thing I can’t actually, even though I’ve heard it a billion times, he’s adjusted it. It’s about, self-improvement making me a better person better, man. And so the earnestness of that makes me accept when he brings somebody on who’s a little bit too academic who’s, Jordan’s interested in it or a little bit too practical to the point where it feels like I’m just getting too many tips on how to network and I don’t need it, but I’ve got his sensibility.He’s trying to make me a better person. And so I think with interviews, if you, if you give people the, the mission, they’ll forgive more, they’ll accommodate the largest and it does allow you to have a broader, a broader set of topics.[00:10:14] Nathan:Yeah. I’m thinking about the mission side of it. Like all of that resonates. and I love when an interview is questions are Like are the questions that they specifically want to know? It’s not like I went through my list and this seems like a good question to ask instead. It’s like, no, no, no, Andrew specifically, I want to know what should I do about, this?And I’ll even call that out in a show and be like, look, I don’t even care if there’s an audience right now. Like this is my list, you know?[00:10:41] Andrew:Yes.[00:10:41] Nathan:But the, like if we dive into the mission, the one that you outlined doesn’t quite resonate. And I think the reason. I think about, creators who have already made it in some way.And it starts to lose that earnestness. Like, honestly, I’m not that interested in, in growing a YouTube[00:11:00] Andrew:I don’t think that that’s I don’t think that that’s it for you. It’s true. That’s a little bit too. I don’t know. It’s it’s a little, it’s a little too early in the career. There is something there. I don’t know what it is and it can’t be enough. It can’t be enough to say I need to meet interesting people because that’s very youth centric and I’m not on a mission to watch you, unless you’re really going to go for like the super right.And we’re constantly aspiring, inspiring. the other thing it could be as you’re running a company, you’re trying to understand what’s going on. No Kagan did that really well. I actually have the reason that I know this stuff is in order to write the book. I said, I have all my transcripts. I can study all the ways that I’ve questioned, but I also want to see what other people have done.And so Noah Kagan did this interview with an NPR producer. I had that transcribed to understand what he did and what he learned. One of the things that he did in that, that made that such a compelling interview is. He was a podcaster who wanted to improve his podcasting. And he, I think he even paid the producer to do an interview with him on his podcast so that he could learn from him.Right. And in the process, he’s asking serious questions that he’s really wondering. He’s trying to figure out how to make a show more interesting for himself. Now. Clearly someone like me, who wants to make my Podcast more interesting. I’m like mentally scribbling notes as I’m running, listening to the podcasting.Oh yeah. The rule of three, like what are the three things you’re going to show me?Well, yeah, at the end he did summarize it and he did edit. I don’t like the edits at all because the edits take away some of the rawness of it and the discomfort which I personally enjoy, but I see now how he’s editing it out.And it’s, it’s interesting to watch that progress.[00:12:32] Nathan:Yeah, I’m thinking through. The different angles that I could take with this. cause I like it and I feel like there’s a, a thread that’s not quite there. And I felt that on the show. Right. Cause people ask, oh, why are you having this guest on versus that guest? and it is that like, I, I find them interesting.There’s also another angle of like probably half the guests maybe are on ConvertKit already. And so I want to highlight that. And then the other half of the guests aren’t and I want them on ConvertKit and so that’s an, you know, an incredibly easy, I can send you a cold email and be like, Andrew switched to ConvertKit.Right. Or I could be like, Hey, you know, have you on the show, we could talk. and we’ve gotten great people like in the music space and other areas from just having them on the show and then[00:13:18] Andrew:Can I give you, by the way, I know it’s a sidetrack and I give you a great story of someone who did that. Okay. it’s not someone that, you know, it’s a guy who for years had helped me out. His name is Bob Highler every week he would get on a call with me and give me advice on how to improve the business.And then at one point he said, you know what? I need new clients. I want to start going after people who are, I want to start going after lawyers, helping them with their online ads, because lawyers aren’t, aren’t doing well enough.He started doing all these marketing campaigns because he’s a marketer. And so one of the things he did was he got these cards printed up.He said, they look just like wedding invitations, beautiful. He, he mailed them out to lawyers. He got one, two responses. Like nobody would pay attention to a stranger, even if they were earnest and sending those out. And he goes, you know, and then he gets on a call. He doesn’t even know what to say to people.If he just cold calling goes, I’m going to try to do that. And Andrew, I’m going to do an interview show for lawyers. He picked bankruptcy lawyers. He started asking them for interviews. They were all flattered because they also want another good Google hit. Right. And so they said yes to him and he asked them questions.Then I started learning the language. I forget all the different terms that he learned about how, about how they operate. But he said, inevitably at the end, they’ll go after it was done. And say, by the way, what are you. And then he’d have a chance to tell them. And because he’s built up this rapport and they trust him, they were much more likely to sign them.He signed up his customers, just like that, just like that. It’s a, I think it’s an, it’s an unexplored way of doing it, of, of growing a business, taking an interest in someone, shining a light on them, helping them get that Google hit and helping them tell their story. And then by the way, will you pay attention to the fact that I’ve got a thing that if you like me, you might like also,[00:14:50] Nathan:So a few years ago, I was in New York and Seth Goden had come out to speak at our conference and he’d ever said, Hey, if you’re in New York and want to make the pilgrimage up to Hastings on Hudson, you know, of outside the city, like come up and visit. And so I did that and it’s so funny, cause it is like this pilgrimage to you, you like take the train up along the river. You know, I don’t know what it is an hour and a half outside of the city. and I was asking Seth advice at his office, about like how to reach more authors. I think that was the question I asked him specifically and he just, he was like, well, what do authors want? And I was like, ah, I, some more books I guess.And he’s like, yeah know. And so like we went through a series of questions, but he’s basically what he came to was, find a way to get them attention so that they can grow their audience to sell more books. And he was suggesting a podcast is the way to do that. What’s interesting is that’s the side, like that’s the other half of it, right.I want to meet interesting people. I want to, Like get more of those people that I find really interesting on ConvertKit pushed the limits of like, our customer base in, in those areas. And then the third thing is I want to do it in a way that’s high leverage in my time. Write of, I want to do it.That creates something, for people watching and listening along so they can follow the journey. But I still don’t see,I would say two thirds of that is about me, right?[00:16:18] Andrew:It’s not only that, but all these things are byproducts more than they are the clear goal. You’re going to get that. No matter what, if you just talk all day about what? No, not talk all day. If you do, what was it? I’m the founder of morning brew does nothing, but like a 15 minute, if that sometimes five minutes.[00:16:37] Nathan:Alex Lieberman.[00:16:38] Andrew:Yeah, just what, what goes on in his life now it’s changed over the years or so that he’s done it, but it’s just, here’s what we were thinking about today. Here’s how I’m deciding to hire somebody BA done. He’s just doing that. That’s enough to get attention enough to also broaden his audience enough to bring us in and then so on.So I think if you just did nothing, but get on camera and talk for a bit, you’ll get that. But I think a higher leverage thing is to tap into that personal mission and let all the others come through along the way and all the other benefits, meaning that you will get to meet people and change the way you think you will get to get people to switch to convert kit.And so on, by the way, that’s such a, like an impressive thing for you to admit, to say, I want to have these guests on because I want to assign them up. I think a lot of people would have those ulterior motives and[00:17:23] Nathan:Oh, no, you got to just talk about, I mean, that’s something you and I, for as long as we’ve known each other have been very, very transparent in both of our separate businesses and our conversations and it’s just, everyone wants that. Right? Cause they’re like, I think I know why Nathan is doing this, but he wants.And that would be weird, but if we go to the mission side of it, there’s mission of like this, I’m going to improve the world side of mission, which definitely exists that can protect you. And I got my little plaque behind me. It says we exist to help creators are living. And so we can take that angle of it, thinking of like the, the goal journey side of things, since we’re just riffing on ideas.One way that might be interesting is to make like a top 100 list of the top 100 creators we want on ConvertKit. And the whole podcast is about interviewing those people and reaching them. And, and so it could be like, this is what I’m trying to accomplish. And you’re going to learn a whole bunch along the way as a listener, but you, you know, we check in on that.And then another angle that we could take that would be different is the, like we’re going together. We’re going to help the creator make the best version of their business. And so you make it more of a.We’re both peers diving in on your business, riffing on it, you know, how would we improve it? that kind of thing.[00:18:43] Andrew:I think helping creators create a business, seems like something others have done, but not quite your approach, your style, the way that you will go and carve something is this is the thing that’s over your head that says create. Is that something you carved in your wood shop? Then I saw on Instagram.Yeah, right. The sensibility of I’ve got to create it my way. Instead of that’s a pain in the ass, I got a business to run who like, right. You’re not going to see, for example, infusion soft, go, we need a plaque. Let’s go to the wood shop. No, you’re not. It’s just not their sensibility. Right. Coming from a sensibility of someone who cares about the details, who every button matters in the software, everything behind your shoulder matters to you for yourself, even the stuff I imagine.If you look forward would have a meaning there, it wouldn’t be random chaos. Is it random chaos in front of, on the[00:19:32] Nathan:The desk is random chaos, but there’s a sign that says the future belongs to creators up there. And[00:19:38] Andrew:Okay. I think I might’ve even seen that online somewhere. So I think that coming, coming from the business point of view, With a sense of creator’s taste, I think is something that would appeal to a lot of people. For whom seeing, for example, my take on business would be completely abhorring. All I care about is where the numbers are and what it’s like.Right. Well, even allium doll’s take on, it would not be, would not be right, because he’s much more about every movement needs to matter. He can’t just have a checkbox in notion it Ellis has to fire off five different other things that notion because otherwise you’re wasting time. Why type five things when you could type one, right.It’s a different sensibility. And I think you’ve always done really well drawing in that audience. I remember talking to a competitor of yours who started around the same time, also done really well about why you were, you were really growing tremendously faster. and they said he nailed it. He nailed who his audience is.It’s the bloggers. It’s these early creators who, who didn’t have. Who didn’t have anyone speaking for them. And you did that. And I think maybe that’s an approach to saying, look, we are creators. And the business of creation is, or the business of being a creator is evolving and we want to learn about every part of it.And then it’s interesting to hear how somebody growing their audience in an interesting way. How is somebody thinking about writing? I love that you asked Sahil bloom about how long it took him to write. I know he talks about it a bunch, but it’s, it’s interesting to hear him go with you about how it is like a five hour, seven hour writing job for him, right.To write fricking tweets. He’s writing tweets, right? You’ve got people just firing off the tweet. He’s spending five, seven hours on it. And, and he’s also not a guy who’s just like, right. It would be something if he was still in school playing baseball, and this is his intellectual, whatever. No, he’s now running in investments.He’s making decisions. He’s helping promote his, his portfolio companies and he’s spending five hours writing and he’s doing it like one a week instead of one an hour. Right. It’s all very interesting. And that approach, I think, ties completely well with ConvertKit.[00:21:41] Nathan:Okay. So where does that take us on like the mission or the hook for the show? Cause we’re.[00:21:48] Andrew:Okay. Here’s what I would do. I would, I would just keep riffing go. My name is Nathan Barry. You probably know me from convert kit. I’m doing this podcast because I like to meet interesting people. And here’s the thing I’m trying to do or I’m I I’m doing it because I’m compelled to talk to these people who I admire.And I also want to learn from them about how they create and just riff on it. Like every week, even have every interview have a different one, until you feel like, oh, that’s the one that feels just right. But if we just here, I want to have this person on, because I’m trying to learn this thing. I want to have this on because secretly I’m trying to see if I can get him to be at, see if I can get Ryan holiday to actually be on convert kit.Right. Boom. Now, now we’re kind of following along as you’re figuring it out. And that’s also[00:22:29] Nathan:Yeah.[00:22:29] Andrew:The way, is Ryan holiday going to be on here or what?[00:22:31] Nathan:On the show,[00:22:33] Andrew:Yeah.[00:22:34] Nathan:Probably we were just talking the other day. We have a shared investment in a ghost town, So we, we often talk about that,[00:22:40] Andrew:Oh yeah. I’ve[00:22:42] Nathan:Other thing[00:22:43] Andrew:That ghost town. Oh, that’s a whole other thing I’ve been watching that[00:22:45] Nathan:I need to have speaking of the ghost town, I didn’t have Brent Underwood on because that Is an insane story of everything going on with town, but it’s just been building this massive audience.[00:22:58] Andrew:Who’s doing YouTube videos from there? He[00:23:00] Nathan:Yeah. And he’s now got 1.2[00:23:01] Andrew:Yeah,[00:23:02] Nathan:Subscribers on YouTube, like 2 million on[00:23:04] Andrew:I had no idea. I watched him in the early days of the pandemic go into this place by himself. Almost get trapped, driving his car to get there. Right. I go, this is fun content. And usually when you watch someone like that and good morning, America go, and I’m going to jump out of this thing.And I’ve never jumped before, maybe whatever. I don’t know.Yo, the producer’s not going to let you die. It’s fine. Here you go, dude. Who’s just trying to get attention for this thing. Cause he has some investors who he wants to make sure get what they want. Yeah, you could die. What the hell is you doing?What? Like I’m going to, I’m going to go down this hole and see if there’s anything over you yet. Dude, you could[00:23:41] Nathan:Yeah. It’s, it’s pretty wild. I actually, some of the weeks that he don’t, he, that he didn’t post the videos. I’d like, texted him, be like, Brett, you’re still alive because you know, the video was the way that we knew every Friday, like, okay, Good Brent. Still alive, everything. Everything’s good. Anyway, I got to have him[00:23:58] Andrew:All right. If you do talk to, if you talk to Ryan holiday, I feel like you totally nailed his writing style, where you, you said in one of your past episodes that he can take a whole historical story, sum it up in two sentences to help clarify the moment that he’s writing about. And it’s like a toss away thing, right? Just toss it away and then move on and go, dude. That’s a whole freaking book. In fact, just turning the whole thing into just two sentences to fit in there would take silo, bloom five hours. You put it in a book with other, like there a bunch of other sentences. So that’s good. But here’s what I think you should talk to him about.Or here’s my, my one suggestion. He has not talked about Marketing since he created, trust me. I’m a lot. Trust me. I’m lying, which was a phenomenal book that then I feel like he distanced himself from when he became more stoic and more intellectual. Fine. He is still a great, great marketer along your style, your tasty.And in fact, he’s becoming the people who I can think of that are very, ConvertKit like philosophy in their creation plus promotion. He nails it, right? Art that takes so much pain that you’ve mentioned, and we’ve all seen it. He has boxes of index cards to create these sentences that most people would just throw away, not pay attention to, but are super meaningful.And at the same time, he knows how to promote. He knows how to get his ideas out there. He knows how to sell a coin that says you’re going to die in Latin, that people put in their pockets that are more than just selling a coin. It’s selling this transferable viral, real life thing. Right. So anyway. And is he should be on a ConvertKit too.[00:25:29] Nathan:He is, he is[00:25:30] Andrew:Okay. Good.[00:25:31] Nathan:Half of his list started in Berkeley. The other half are in the process of switching over. So, you know,[00:25:36] Andrew:Okay. Yeah, that’s the hard part, dude. I I’m with infusion soft. I can’t stand them. If you understand how much I do not like them. I do I ever talk negatively about anyone. No. Bring up politics, Joe Biden, Donald Trump. I got no strong opinion about anything you talked to me about, about infusions. Ah, but the problem is it’s so hard to wean yourself off of these things because once you’re in a system, that’s it[00:25:56] Nathan:Well we’ll make it happen. W w we’ll figure out a way, but the new book landing page for it, I went on there and inspected element. It’s definitely a ConvertKit for them. I was pretty happy about it.[00:26:06] Andrew:Oh yeah, yeah, yeah, yeah. So truthfully it was, I said, I’m not going to school around here. It would have probably been easier for me to go with, with infusion soft because then we all we’d have to do with tag people who were interested. And then I could, I don’t want that. I don’t want that nonsense because it comes with overhead.That becomes an obstacle to me, communicating with my audience by, by overhead. I mean, they’ve got historic legacy. Requirement’s that mean I can’t do anything right. You I’m on my iPad. I could just go in and send a message out. Or actually I haven’t sent a message out. Someone else has sent a message out.Our publisher sent a message then from damn, ah, damn gravity. But I, but if someone says there’s a problem, I can go in and see it.[00:26:44] Nathan:Right.[00:26:44] Andrew:And make adjustments. The whole thing just fricking works. Right?[00:26:47] Nathan:So I want to talk about the book more. Let’s talk[00:26:49] Andrew:Sure.[00:26:50] Nathan:And now I have you here.[00:26:52] Andrew:Ben needs, us to talk about the book. He’s the publisher.[00:26:54] Nathan:We’ll get to that, then don’t worry. Ben, we’ve got it covered. so you were giving unsolicited feedback, which by the way is my favorite kind of feedback. Okay.So as you’ve been listening to the show, what are some other things that maybe you recommended the book, maybe like as you set people up for interview questions, any of that advice that you would give beyond?We started with the men.[00:27:15] Andrew:I’m going to suggest that people who listen to you do pay attention to this. One thing that they should, I I’m interrupting you in a roadway now there’s some good interruption that I write about in the book and I can tell you how to do it. Right. And I also have to say that there’s some new Yorker that’s built in, even though I’ve left New York a long time ago, that I, I always interrupt when we need to get into the bottom line.Okay. Here’s one thing that I think people should pay attention with you. You don’t just ask questions. You will, at times interject your own story, your own, take your own experience. And I find that a lot of times people either do it in a heavy handed way. It’s like, look at me, I’m equal to you. I deserve to be in this conversation too.And that doesn’t just happen on Mike. It happens at dinner parties or it’s more like I have to be reverential. So I’m asking questions and it’s me asking about them. And one of the things that I learned over the years, Getting to know someone interviewing someone, whether it’s like you and I are doing in our podcasts and shows or doing it, in a, in a dinner conversation, it’s not asking questions.It’s not about saying here’s my next thing. Here’s my next question. It’s overwhelming and draining to do that. You do need to say, well, here’s me. You do need to sometimes just guide the person to say, now tell me how you wrote the book. Now tell me how long it takes to, to write a tweet, right? Whatever it is, you need to sometimes direct the person.And so I call the book, stop asking questions because that counter intuitive piece of knowledge is something that took me a fricking interview coach to help me accept that. It’s true, but it helps. And you do it really well. And here’s why you do it. Well, you interject something personal. Somehow you do it succinctly.You don’t get rambling off. Maybe you edit that.No, no, because the videos are there. Yeah. It’s, it’s not edited. It’s just you saying here’s, here’s my experience with this. And then when you come back and you ask something. It informs the guest about where you are and what they could contribute to that. It lets them also feel like this is a dialogue instead of them being pounded with demands of, in the forms of question.[00:29:15] Nathan:Yeah. Yeah. I think that for anyone listening and thinking about starting a podcast, it’s really like, what’s the kind of thing that you want to listen to. And I like it where the host is like a character in the, in the Podcast, in the episode where they’re contributing content and it’s not just like, oh, if I listened to Andrew on these 10 shows, I’m just going to get Andrew.Like, I want it where it’s like, no, I’m getting the blend between these two people. And the unique things that come from that intersection rather than, you know, I’ve heard this[00:29:46] Andrew:Yes.[00:29:47] Nathan:I’ve heard about it.[00:29:48] Andrew:I think also it took me a long time years of, so I started doing this in 2007, give or take a year and I think. No one needs to talk about, I don’t need to talk about myself. They don’t care about me. They care about, you know, Paul Graham, who I’m interviewing about how he found a Y Combinator, someone.And I would get tons of emails from people saying, tell us who you are. Tell us a little bit about yourself. And I would argue with them and say, no, but I understand now on the outside, when I listen, I don’t know who you are. And it feels very awkward to hear it. It feels very much like, I don’t know why, where you’re coming from.And so I don’t know why I should listen. It’s kinda, it’s it’s counterintuitive.[00:30:29] Nathan:Yeah. I think it just comes with comfort over time. Like, I, I don’t know this for sure. If I bet if I listen back to my first podcast episodes, the ones that I did in like 2015. I have a different style because I bet I’m less comfortable or more worried about like, make sure that I shut up quickly so that the guests can talk more because people came here for the guest and then over time you just get more comfortable.[00:30:53] Andrew:So you wrote authority and I remember you, I remember buying it and I remember you bundled it with a bunch of stuff, right. And oh, by the way, it’s so cool. I was listening to it on a run and I heard you mention my name in the, in the book I go, this is great and I’m running. but I remember you did interviews there.I don’t remember whether the style matches up to today or what, but you did interviews in it. Right.[00:31:15] Nathan:I did.[00:31:16] Andrew:And what you had there that I think is always important to have with all, all interviews is you had a sense of like, well, the sense of mission, I knew what you were going for, because you were trying to say, here is this book that I’ve written on this topic.I’m want to bring these people in to bring their, their take on it. We were all kind of working together. And I feel like, when I look at my earlier interviews, I listened to them. The Mike sucks so badly. I was too ponderous. Cause I wanted to be like, IRA glass from, from NPR, from this American life.And you could hear the same rhythm, the same cadence, like I’m copying him. Like I’m his little brother trying to learn how to be like a real boy. but I had this real need. I was trying to figure out how these people were building companies that work to understand what holes I had in my understanding to see what was working for them that I didn’t know before.And you could see that and it, it helps. It helped me continue. Even when I was nervous with the guest, it helped the guests know where to go. Even when I wasn’t doing good job, guiding them and help the audience keep listening in, even when the audio stopped, because there’s this thing that Andrew is trying to understand.And you almost feel like you’re the sense of vulnerability. If it doesn’t scare you away, then it makes you want to root.[00:32:40] Nathan:Yeah. And I personally love that style because I want to follow someone going on a journey and, and trying to accomplish something specific. But let’s talk about the not just the book, but asking questions or in this case, stopping it, stop asking questions. What are the things that not even just specific to this job, what are the things that you listened to interview shows?And you’re like, okay, here are the three things that I want to change or that I want to coach you on in the same way that I was coached on.[00:33:10] Andrew:Okay. So what I started to do is I go through my own transcripts. I mean, I had years of transcripts to see what worked and what didn’t I already done that. So I said, I need to now add to it. And so I went back and looked at historical interviews, like when Barbara Walters interviewed Richard Nixon and got him so frustrated that he didn’t want to ever talk to her again.Or when Oprah finally got to sit with Lance Armstrong, how did she do that? I think. You know, you know, let me pause on, on Oprah and Lance Armstrong. She got to interview him after he, he was basically caught cheating and he was about to come out and do it. Great. Get, I think the fact that she interviewed him, there’s a lesson there for, for all of us who are interviewing, interviewing the top 10 interviews, I think of all time.And you go back to Wikipedia and look it up. You see art or interview podcast or interview, sorry, our news-based interviews. We as podcasters, keep thinking, how do I get enough in the can so that if I die tomorrow, there’s enough interviews to last for a month or whatever, so that I can be consistent in the audience loved me.That’s great. But I think we should also be open to what’s going on in the world today. Let’s go talk to that person today. If there’s an artist who suddenly done something, we should go and ask to do an interview with them. If there’s a creator, if there’s someone. So for me, one of the top interviews that people still it’s been years, people still come back and talk to me about is when Matt Mullenweg decided that he was gonna pull out Chris[00:34:35] Nathan:Pearson.[00:34:35] Andrew:Per Pearson.Pearson’s, themes from WordPress. And I got to talk to both of them at the same time and I published it and it went all over the internet with all over the WordPress internet. So hundreds of different blog posts about it, eventually all the people in the WordPress world write a lot of blogs, but also it became news.And so we don’t do enough of that.[00:34:57] Nathan:I remember that interview because I was in the WordPress community at that time. And I remember you saying like, wait, I’m in Skype and I have both of you in two different things and you pull it together and not to pull Ryan holiday into this too much, but that’s where he ended up writing the book.Was it, he realized he was one of the only people who was talking to like both Peter teal and, who’s the Gawker guy.Yeah. Anyway, people know, but, but being in the intersection of that, so you’re saying find something that’s relevant on the news[00:35:33] Andrew:Yeah. Nick Denton was the founder of Gawker. Yes. Find the things that are relevant right now. And when people are hot right now, and they know you and you have credibility in this space, they trust you more than they trust. Say the wall street journal, even right, where they don’t know where’s this going.I think that’s, that’s one thing. The other thing is I think we don’t have enough of a story within interviews. If we’re doing S if we’re doing at Mixergy, my podcast and interview where we’re telling someone’s story, we want them to be somewhere where the audience is at the beginning and then to have done something or had something happen to them that sets them on their own little journey.And then we make this whole interview into this. Into this a hero’s journey approach. So I think better when I have an actual company in mind, so, or a person in mind. So last week I was interviewing this guy, Rohit Rowan was a person who was working at SanDisk, had everything going right for him. His boss comes to him and says it, you’re now a director, continue your work.But now more responsibilities he’s elated. He goes back, home, comes back into the office. Things are good, does work. And then a couple of days later he’s told, you know, we mean temporarily, right? And he goes, what do you mean? I thought I got, I got a promotion. No, this is temporary. While our director’s out you’re director of this department.And then you go back, he says, the very next day, he couldn’t go back into the office. He sat in his car, just, he couldn’t do it anymore. And so he decided at that point, he’d heard enough about entrepreneurship heard enough ideas. He had to go off on and do it himself. And so we did. And then through the successes and failures, we now have a story about someone who’s doing something that we can relate to, that we aspire to be more.[00:37:13] Nathan:So, how do you, you, your researchers, how do you find that moment before you have someone on? Because so many people will be like, yes, let me tell you about my business today. And oh, you want to know about that? How’d, you know, you know, like, as you,[00:37:27] Andrew:Yeah,[00:37:28] Nathan:That hook in that moment? That actually is a catalyst in their own dream.[00:37:33] Andrew:It’s tough. It’s it takes hours of talking to the guest of, of looking online of hunting for that moment. And it takes a lot of acceptance when it doesn’t happen. One of my interview coaches said, Andrew, be careful of not looking for the Batman moment. And I said, what do you mean? He goes, you’re always looking for the one moment that changed everything in people’s lives.Like when Batman’s parents got shot. And from there, he went from being a regular boy to being a superhero. Who’s going to cry, fight crime everywhere. His life doesn’t really work that way. There aren’t these one moments, usually the change, everything. So I try not to. Put too much pressure on any one moment, but there are these little moments that indicate a bigger thing that happened to us.And I look for those and I allow people to tell that without having it be the one and only thing that happened. So if Pharaoh, it, it wasn’t that moment. It could’ve just been, you know what, every day I go into the office and things are boring. And I think I have to stop. What I look for is give me an example of a boring.Now he can tell me about a day, a day, where he’s sitting at his desk and all he’s doing is looking at his watch, looking at his watch and he has to take his watch, put it in his drawer so that he doesn’t get too distracted by looking at his watch all day. Cause he hates it. Now was that the one moment that changed everything?It was one of many moments. It might’ve happened a year before he quit, but it’s an indication. So when we’re telling stories, we don’t have to shove too much pressure into one moment, but I do think it helps to find that one moment that encapsulates their, why, why did they go on this journey? Why does someone who’s in SanDisk decide he’s going to be an entrepreneur?Why did someone who was a baseball player decide that he had to go and write a blog post? Why is it? What’s the thing that then sends them off on this journey? It helps. And I would even say, if you can get that moment, it just helps to get the thing that they were doing before that we can relate to. So what’s the thing that they did before.So anyway, we have two different types of interviews. One is the story-based interview where we tell a story of how someone achieved something great. And so that hero’s journey is and approach. The other one is someone just wants to teach them. All you want to do is just pound into them for an hour. Give me another tip another tip another tip of how to do this.Like pound, pound, pound, pound pound. If you want the audience to listen. I think for there, it helps to have what I call the cult hook because I said, how do I, how do cults get people to listen to, to these people who are clearly whack jobs sometimes. And so studying one called I saw that what they did was they’d have a person up on stage who talked about how, you know, I used to really be a Boozer.If you came into my house, you would see that there’d be these empty six packs. I was so proud of leaving the empty six packs everywhere to show myself how much alcohol I can drink. My wife left me. And when she left me, she just told me that I hadn’t amounted to anything in my life. And I was going nowhere.And I just said, get I here. Instead of appreciating that this was just like terrible. And I ran out of toilet paper and don’t even get me started with what, what I did for that. And so you see someone who’s worry worse off than you are on this path of life. And then something has. They discover whoever it is.That’s the cult leader. And they say, now I’ve got this real estate firm I encouraged by, oh, by the way, all of you to come over and take a look at that at this, I couldn’t believe it. My whole life. I wanted to buy a Tesla. I now have the Tesla S it’s amazing. It’s just so great. And I did it all because I changed the way I thought once I came in and I found this one book and the book told me, I mean, anyways, so what we try to do is we say, if you’re going to have somebody come on to teach how they became a better blogger, let’s not have them start over elevated where everything they do is so great that we can’t relate, have them start off either relatable or worse.I couldn’t write here’s my grammar, mistakes. My teacher told. Right. And now what’s the thing that they did. They pick them from where they were to where they are today. it’s this real set of realizations. Now I want to go into that.Let’s pound into them and see how many of those tips we can get. Let’s learn that I want to go from where he was to where he is.[00:41:28] Nathan:Yeah, I liked that a lot. Cause my inclination would be like, okay, we’re we’re doing the, educational, tactical conversation. I’m going to facilitate it. Let’s dive right in and let’s get to the actionable stuff right away. So I like what you’re saying of like, no, no, no. We need to, even though this is going to be 90% packed, full of actionable material, we need to dive in and set the stage first with the story and making it relatable.And I like it.[00:41:55] Andrew:Yeah,[00:41:55] Nathan:Oh, yeah. I was just, just in my own head for a second. Cause I say, ah, that makes sense a lot, so much so that I’ve had three different guests or listeners email me and say like, just don’t say that makes sense as much would, now that I’m saying it on the show, I’ll probably get more emails every time that I say it.Cause that’s like my processing, like, oh, oh, that makes sense. As I’m thinking of the next question and all that, so[00:42:22] Andrew:I do something like that too. For me. It’s IC,[00:42:25] Nathan:Everyone has to have something.[00:42:26] Andrew:I can’t get rid of that and yeah.[00:42:28] Nathan:So what systems have you put in place on the research side so that you’re getting this, are you doing pre-interviews forever? Yes. Are you having your[00:42:38] Andrew:Almost every single one, some of the best people in some of the best entrepreneurs on the planet, I’m surprised that they will spend an hour or do a pre-interview. And sometimes I’m too sheepish to say, I need an hour of your time and I need you to do a pre-interview. So instead of saying, I need you to do a pre-interview.I say, here’s why people have done it. And I’ve paid for somebody to help make my guests better storytellers of their own stories. And truthfully people will go through that. Pre-interview even if they don’t want to do an interview, they just need to get better at telling their story for their teams, their employees, their everyone.Right. and so I say that, and then they will take me up on the pre-interview and say, yes, I do want to do the pre-interview. and so what I try to do is I try to outline the story. Ahead of time in a set of questions. And then what we do is we scramble them up a little bit based on what we think people will tell us first and what will make them feel a little more comfortable.And then throughout the interview, I’ll adjust it. So for example, no, one’s going to care about the guest unless they have a challenge. No guest wants to come on and say, I’m going to tell you about what’s what I really suck at or where I’ve really been challenged. If they do, they’re going to give you a fake made up thing that they’ve told a million times to make themselves seem humble.So we don’t ask that in the beginning. We don’t even ask it in the middle. We save it till the very end. Now they’ve gotten some time with us. They’ve gotten some rapport, they trust us. Then we go into tell me about the challenges, what hasn’t worked out for you. And we really let them know why tell people the higher purpose you want the audience to relate.You want them to believe you. You want them to see themselves in you, and to learn from you. We need. They tell us, and then I have it in my notes as the last section, but I use it throughout the interview. I sprinkle it. So the goal is to get the pieces that we want and in whatever order makes the most sense and then reshape it for the interview Day.[00:44:33] Nathan:So on the interview itself, you would, you would flip that and you know, okay, this is what I want to start with and, and dive in right[00:44:41] Andrew:Yup. Yup.[00:44:43] Nathan:Lose. They already told you about that. And so now, you[00:44:46] Andrew:Right,[00:44:46] Nathan:In and start with.[00:44:47] Andrew:Right. That helps. Now, if there’s something I want to ask someone about that they’re not comfortable with. One thing that I do is I, I tip them off. So Jason Calacanis invited me to go do, interviews with, with investors at one of his conferences. It was just a bunch of, investors. And I looked at this one guy, Jonathan tryst, and he looked really great.But he, what am I supposed to do? Ask him about what startups should do to run their businesses. He’s never run a startup. His, he hadn’t at that time had a successful exit. As far as I knew, like mega successful exit. He’s just a really nice guy. You can tell he was going places, but that’s it. And the money that he was investing came from his parents.So what is this rich parents giving their kids some money. Now he’s going to tell everyone in the VC, in the startup and VC audience, how to live their lives. So I said, I’m either not going to address it, which I think most people are, or I have to find a way to address it where I’m not going to piss them off and have them just clam up on me and then go to Jason and go.This guy just is a terrible interviewer, which is not true. So what I decided to do was tip him off. I said, look, Jonathan, before we do this, before we start talking to the audience, I have to tell you, I saw it, that you don’t have much of a track record as an investor. Your money came from your parents and you’re not like a tech startup, like people here.If we don’t talk about it, people who know it are going to think, oh, this guy, Jonathan, look, who’s trying to pass him soft self off. I don’t have to force it in here, but if you allow me to, I’d like to bring it up and let’s talk about, and it goes, yeah, absolutely. If it’s out there, I want to make sure that we address it and sure enough, we talked about it and he had a great answer.He said, no, this came from my parents. It’s not my own money. I don’t have as much experience as other people, but I took my parents’ money. I invested it, fat parents and family and so on. We’ve had a good track record with it. And now have raised the second Fallon fund from outsiders who saw what I was able to do with the first one.And by the way, I may not have this mega exit as a startup investor, as a startup entrepreneur. But I did have this company that did okay. Not great. Here’s what it did Here’s what I learned And that’s all informing me. And that’s where I come from now. You’ve got someone talking about the, the, the thing that matters without pissing them off so much that they don’t say anything else.And you feel like you feel superior as an interviewer. I got them. But in reality, you got nothing[00:46:57] Nathan:Right.[00:46:57] Andrew:Cares.[00:46:58] Nathan:I think that’s a really hard line of talking about the things that are difficult and like the actual, maybe things that someone did wrong or lessons that they learned without just like barely dipping into it for a second. And I liked the format of tipping them off in like full transparency.So on this show, I had someone on who I really, really respect his name’s Dickie Bush. He’s one of the earlier episodes in this series and in it, he, okay. Yeah. So in that interview, one thing that I knew is that his, the first version of his course plagiarized text from another friend, Sean McCabe, actually Shaun’s company edits is Podcast and all that.And I’ve known both of them for, for quite a while. I’ve known Sean for like, I dunno, six, seven years or something. And I was like, struggling with how to bring that up. And I wanted from the like founder, transparent journey, that sort of thing I wanted it brought up because I, I actually like, I’m happy to talk about like some pretty major things that I’ve screwed up and what I’ve learned from it.And I just think it makes a better conversation. And then from the interview side, I don’t feel good, like doing an interview and not touching on that, but I didn’t tip Dickey off to it. And I, that was one of the things that I’ve regretted that he gave a great answer. He talked about the lessons that he learned from it.It was really, really good, but I felt bad that I didn’t set him up for the most success in like in setting up. And part of that, part of it is because even at the start of the interview, I was still wrestling with now, I’m not going to bring that up that, ah, maybe I should, it wouldn’t be an authentic interview if I didn’t like wrestling with that, I hadn’t figured out my own, like made my own decision until we were in the middle of it.And so I didn’t, I didn’t set anybody up for success. And so it’s an interesting line.[00:48:52] Andrew:It happens. And it seems like I’m now in the point of your transcript, where you, where you ask him, it’s a 31 minutes into the interview. I think his response is great. He came in and he took responsibility for it. He says, yeah, that, that, that was a dramatic mistake, or a drastic mistake on my side and caught up in it.He wasn’t the most articulate here and he’d repeated words. Like I, I, a couple of times, so I could see that he probably was uncomfortable with it. but I think his answer was great. I think, I believe that we all are broadcasting out, whether we know it or not, our intentions and where we’re coming from, as some people are really good at faking it.And so I’m not going to talk about the outliers and some people are so uncomfortable that they’re messing up the transmission, but for the most part almost. broadcasting our intentions. If you walk into that, Nathan, with the, I got to get him because he, he got one of my friends and I need him to finally get his comeuppance.He’s going to pick up on that. And truthfully, it’s such a small thing for a person like you who’s, who’s already a likable person. You have a lot to offer people, right? As far as like promotion and everything else, it will be forgiven, but it’ll be picked up on, it’s also something that people could pick up on, which is Nathan really want to know this thing.It’s been bothering him for a while. And if you could, just, before you asked the question, say, where am I coming from with this? And know that the audience will mostly pick up on it. And obviously people are gonna like read in whatever they feel like, but trust that the vast majority of us understand, I think it’ll work[00:50:21] Nathan:Yeah,[00:50:22] Andrew:You don’t have to even tip. You don’t have to tip off, but it does help. It, it definitely helps.[00:50:26] Nathan:It’s interesting. I was watching an interview with, Jordan Peterson who wrote 12 rules for life. He’s like a very controversial figure. And I was just often these controversies pass by, on Twitter and other places. And I realized like, oh, I don’t understand them. And rather than jumping on one side or the other, at least try to like dive in a little bit and understand it.So watching this interview, and I can’t remember, I think it was some major Canadian TV show or something, and that you would tell the interview was just trying to nail him it every possible chance, like whatever he said, just like dive in. And, so I think you’re right, that you see the intention, like in that case, you would see the, the interview, his intention was specifically to try to trip him up in his words.And then in other cases where it’s like, This is something that, you know, if you take the other approach, this is something that’s been bothering me, or I want to talk about it. Like I genuinely want, you know, to ask or learn from this. It’s a very different thing.[00:51:20] Andrew:I think people pick up on it. I remember you, you mentioned Seth Godin. I remember interviewing him when he wrote the book tribes back before people had online communities. And I didn’t just say, okay. All our heroes, all the best entrepreneurs just run their businesses. Then don’t run a tribe. I brought out books.I said, here’s a book about Warren buffet. Here’s the book by Sam Walton. The Walmart here’s a book by Ted Turner became a multi-billionaire to creating all these, these media empires didn’t have communities. They don’t have tribes. And now you’re telling me that in addition to my job, I also have to go and build out a tribe.It feels like, you know, an extra job. That just seems right for the social first. This just sounds right on social media and you could actually see. He’s watching me as I’m saying it, and he’s smiling, he’s watching it because he’s trying to read me, is this like what I get wrapped up? Is this going to be some kind of thing where some guy’s going to try to be in the next Gawker media?Or is, is this a safe place? We’re all doing that constantly. And then he also saw, okay, this is someone who really wants to understand this. And he’s challenging me. I like a challenge. And you could see him smile with like, this is what I’m here for. And so I think when you come at it from a good point of view, people can see it and then you can go there and you can go there and you can go there and it will be shocking to you and them and the audience, how far you go. But when you’re coming from that genuine place, they get, they get it.They want it.[00:52:44] Nathan:Yeah, that’s good.I want to talk about longevity in like the online world. I think that so many people that I started following in say 2007, 2008, nine, and then I didn’t start creating myself until 2011. most of them aren’t around anymore. Like a lot of the big blogs, Yeah, just so many that I can think of.They’re not around anymore. They’re not doing this. You’re at a point where like you started messaging in some form in what? 20, sorry, 2004 to somewhere in there and then interviews.[00:53:17] Andrew:Yeah, I keep saying 16. It’s like, yeah. 2004 is when I started the interview started 2007 ish somewhere there. Give or take a year. yeah, long. I, I will say that there are parts of my work that I am burned out on right now. This year has been that, but I’m not on the interview. And the reason I’m not is because I do enjoy conversations.I hated them for a long time in my life because I just didn’t know how to have them, how to have it make sense. I also didn’t give myself permission to take the conversation where I wanted it to go. And it helps now to say, I can talk to anyone about anything. That’s an opportunity that, that feels fun because I know how to do it.It’s an opportunity to, it feels like, like, you know how everyone’s so happy. You can go to YouTube and you could get the answer to anything. Well, I could go to anybody and I could get the answer to anything and talk about how they didn’t have a customized to me, YouTube, not customized thing to me, I’m watching Gotham chess on YouTube.He’s teaching me how to play chess, but he will not customize to the fact that every time I get into a car con defense, all the pieces like bunched over to my side. But if he and I did an interview, or if I do an interview with an tomorrow’s entrepreneur, it’s going to be about, here’s the thing I’m trying to deal with.How did you get past that? Talk to me about what you’re up to there.[00:54:31] Nathan:Yeah, that’s definitely energizing. Okay. But what are the things that you’re burnt out on? Because I think a lot of people are seeing that burnout. And so I guess first, what are you burned out on? And then second, we can go from there into like, what are you changing and how are you managing.[00:54:46] Andrew:I’m burned out on parts of the business behind, behind Mixergy I’m burned out on. I was aspiring to like unbelievable greatness with the, with the course part of it, with the courses, it didn’t get there and I’m tired of trying to make it into this thing. That’s going to be super big. I’m tired of that.[00:55:10] Nathan:His greatness there, like linda.com? Like what, what was that?[00:55:15] Andrew:Yeah, yeah, yeah. Yes. Yeah. She was one of my first interviewees and, and so yeah, I saw the model there and I am frustrated that I didn’t get to that and I, I don’t have a beat myself up type a personality, despite some of the questions that I ask. Maybe it seems that way. I’m pretty good with it, but, but I’m tired of being, trying to get it there and not getting it they’re trying and not, and trying another way.And so to answer your question of what am I doing, I’m going to give myself space to not, to not try to do that, to not try to, to go for greatness for a little bit, and instead give myself room to do the interviews that I care about and play more chess and then experiment with random things that I don’t know what will come up, you know?I don’t know. At one point I, I think I, so I get together with some friends for monthly calls and, and one of the calls I said, I’m looking at land and what if I get some land near San Francisco, right? It’s super cheap in San Francisco. You can buy a tiny house for two, 200, excuse me, for $2 million. But if I just go 45 minutes down south a little bit further down than Silicon valley. For $400,000, I get acres. And then I could put some tents on there. Maybe get an Airstream, let people stay on it and see what that goes. Anyway. That’s such a random thing that I think that they were a little worried about me, but I’m even open to random ideas like that. And then who knows, maybe come back after a year of taking that space.[00:56:53] Nathan:Yeah, that makes sense to me, of, of taking space and time, you know, like first you know, years ago it was the great recession. Now everyone’s talking about the great resignation where like the, I don’t know the exact statistics, but a crazy number of people across the industry, but especially like knowledge workers and people in tech are either switching jobs or just like putting their notice and like saying, I don’t know what I’m going to do next.But like, I, I, I’m fully confident that when I’m ready to come back, there will be a job, you know, some kind of Write of like, I’ll find another programming job. That’ll be fine. And so I think it’s a good thing to talk about because so many people are feeling. And most people just leave it at, like I’m burned out, so whatever.Right. You know, so I pushed through or I’m burned out. So I left, you know, and so actually talking about those things that that either drove the burnout or, you know, specific things that you’re doing about it.[00:57:52] Andrew:So are you asking me what drove my book? Me to my burnout.[00:57:56] Nathan:Yeah. I’m, I’m curious for more of that.[00:57:58] Andrew:Sure. I think I have this all or nothing. Personality I’m all in or nothing. So, it, it’s not like I’m going to do a nice two mile run. I have to do a marathon and then I have to do another and another and another,[00:58:17] Nathan:In a year.[00:58:18] Andrew:Right. Yeah, exactly. And that fits me. I want to be the person who I love scotch. I’ve been in Austin for a little bit and they don’t sell them everywhere.You have to go to special liquor stores. I haven’t had any here. Right. So I’m down to zero. That’s also, excuse me, fine. But if I’m drinking scotch with people, I’ll finish a third of the bottle, half the bottle, no problem. And then I’ll wake up the next morning and be the person who is so proud that he’s like Up before everyone else and running into work.I think that that type of thing suits me, but I think that the downside of that is that then I do just burn out and I can say that that’s happened now twice before. So I think that that’s what’s happening now. The first was in college. I took college really seriously because I thought this is going to show you.I thought it was gonna shape my future. it really didn’t, but I wanted to really do well in all those classes. Especially since I finally got business classes after years of wishing I could study business or something practical, but instead being given things that like the Pythagorean theorem, that didn’t matter, I had it.So I took it seriously. But I remember at the end I graduated, burned out where I remember my boss offered me a job and I said, I really just can’t think, I think what the offer you’re making me make sense. I just don’t know. And I took time off. I drove my parents crazy is I finished school and didn’t want to work anywhere.And then again, after my greeting card company, I worked on that endlessly. I would take a keyboard with my phone into bed so that I can type out long emails in response to people. and then I burned out and decided I would just go ride my bike on the Pacific coast highway for a year, whatever for years.[00:59:56] Nathan:Is there anything that you’re taking into this period of, of like space. That you’ve learned from the, from the past months or your added level of intentionality,[01:00:07] Andrew:No, I don’t, I’m not there yet. I’m really excited about this book. And so I’m talking about it. I’m really excited about the process of interviewing. I feel like I underestimated the importance of it until I wrote this book. So COVID just had me locked up inside for a bit. And I said, all right, I’m how do I use this?And I ended up writing the book and then as I examined it, I realized I really do love the craft of conversations, the, the, the structure of them, of how we end up with, how, how do I end up in a great conversation with people? My kids this morning, one of them is seven. The other’s five to seven year old, said we are not shy on like other kids.We go in with adults and we have conversations with them all the time, because you always get us in, you talk to everybody. And I thought, what a gift that they could we’re in Austin, that they could go to somebody’s house and feel as comfortable in their houses as any one of their friends does, even though.You know, the first time that they’re, that they’re in the house and they don’t even know if there’s anything for kids to do. I love that. And that doesn’t just come from happenstance or gift from God. It just is spend time. I spend time thinking about it And working on it And I’m proud of it. So I’m continuing to do that.And then who knows what will come after burnout, maybe after burnout will just be sitting on the couch with chess.com all day. Just try to master that CARICOM defense.[01:01:21] Nathan:Yeah, that’s a good, good use of time. I think I say that genuinely. I, I am not on,[01:01:30] Andrew:Thanks.[01:01:31] Nathan:Of, of chess, but I thoroughly enjoy it. And I, you know, I play chess against a ten-year-old and a seven year old for the most part. And getting to the point where they can.[01:01:38] Andrew:The good actually seriously, if you take a look younger kids for some reason, if they’re good, they’re amazing. They’ve got to, I don’t even know how they can[01:01:46] Nathan:Yeah. And, but it’s, it’s also amazing to see. I mean, my kids aren’t, aren’t phenomenal by any means. I can still beat them, but they’re like, you see the, the rate of improvement over time, especially if you explain, like, don’t do this, where do I see why this is a bad idea? Like they will not make that mistake again, you know? at least in chess, I haven’t figured out the parenting side of that.If you have, let me know.I’m curious on the, on the other side, like going to the interviews, is there anyone that you have on your list that you’re like, oh, I really want to interview this person, or maybe this person tied to this a point in time as well,[01:02:24] Andrew:You know what it is? It’s sometimes something will make it into, into the news. Someone will have done something amazing. We’ll all start talking about them and I’ll want that person. And one of the gifts of this, of this experience of having been out there for so long as I could, I could say, there’s, there’s this person, who’s this, this guy, Andrew, I can’t remember his name.White. He just talked about. This is so small. You’re probably thinking about who’s it like a major mark Cuban. I’m not interested in mark Cuban. I’ve heard everything has to say here’s my excite, my excitement, this dude, Andrew he’s finally revealed how much money he made from. I think it was, he must have hit a million dollars.My memory is not great on this, but here’s what I do. He wanted to have his own software company. He had a wife and kid, he couldn’t find a way to squeeze it in. He knew he needed to learn to program. He decided that on the way into work on the train, he would sit there with a laptop. You ever see people on the train with the laptop?I feel so sad for them, right? This is no way to work. It’s not comfortable. And plus I feel like I, cause that maybe it’s because I had lived in New York and San Francisco, I feel like someone’s going to snatch it out of their hands, poor souls. And they’re going to lose the laptop too. But he’s one of those poor souls sitting there working.And he ends up creating this company that does charts because he realizes for developers hard to make nice looking charts. And so he says, I’ll create a way. Developers can just plug into my stuff and they’ll have nice looking charts. And suddenly people who are racing cars who need charts to see how the cars are doing and different parts of the cars are performing midway through the race.They’re using his charts to show that like it’s making great money and his life has changed. And I did that guy a lot and I love that. I have the freedom to say, people are talking about him right now. I am curious about him right now. I’m going to go and ask him right now. Can we do this interview? That’s helpful. And then one more thing I think for doing interviews and you’re, you’ve seen this in your own life in different ways. There’s also like a follow-up effect where the people who you’ve done interviews with you may never see them again. But some you have access to for the rest of both of your lives.I mean, literally for the rest of both of your lives. So one, one example is I started writing the book. I couldn’t keep on writing it. I’m sitting down here at my iPad, typing away. I couldn’t do it. I can’t, I can’t believe how many words a day I keep in my head. Someone asked you on Twitter while I was writing this.Do you still do a whatever number of words a day? And you gave the number of word I want to punch my screen. I go, how the hell is this guy doing it? I can’t do it. Hey, I said, I’m going to hire a ghost writer. And I started emailing Ryan holiday to go. This is terrible. I’m literally giving up other, every other part of my work in life, except for like, after, with my kids, after they’re done with school, I’m done except for writing this book.How do I continue this? How do I hire a ghost writer? And his response was the most in sympathetic response ever, but it was great because that’s what got me to like stop looking to hire a ghost writer. And I’m the type of person who I would just hire someone, give them a direction and be done. And so don’t think if I were just a random dude, messaging people all day, that they would respond like that.I don’t think I was a random dude, not knowing how to master the Cara con that James Altucher was a phenomenal chess, chess player, right. And a great writer I’m reaching out. He goes, let’s get on a Skype call or zoom call. We get on a zoom call. We only met during the interview. The dude is so good. He’s analyzing my game.He’s giving me homework assignments. I did one of his homework assignments this morning, and suddenly my game has improved because of it. There’s this extra benefit, and it reminds me of something that Ali Abdaal said in your interview. He said, if you stick with this (and for him, it was YouTube), if you stick with this for month after month after month, I guarantee you it’ll change your life.I’m not going to make promises on what you’ll have financially, but I guarantee you it’ll change your life. I wish he would have said change your life for the better, because I’m a little worried about the people sitting there creating YouTube videos, and their lives getting destroyed from all the hours.But, I think if you sit there and you do interviews, guaranteed it changes your life for the better.[01:06:17] Nathan:Yeah. I mean that consistent way of showing up makes a huge difference, and access to people is incredible, and the relationships, and everything else.[01:06:25] Andrew:Yup.[01:06:26] Nathan:Where should people go to check out the book?[01:06:28] Andrew:I got this great landing page from a company called ConvertKit. Alright, here’s all they have to do:[01:06:33] Nathan:I love it.[01:06:34] Andrew:All they have to do is go to: StopAskingQuestions.co, and here’s all I have to do. If I have to send out a message, I don’t have to figure out crazy charts, and all these systems and rules.I just log in—I could do it on an iPad—and then I send out my message. What I’ve been doing, Nathan, is when I hear that people have a problem with conversation, I find a chapter from the book and I email it out. Then I say, what do you think? Is this working?I send that out to the whole list, and it’s so helpful to have people email me back, asking for direction or saying how they’ve used it. One person had this terrible story about some bad thing that I did with the founder of Zero, the accounting software.I was hoping that people wouldn’t ridicule me for that, or judge me negatively for it. Nobody did. So, that made me feel good, and I left it in the book. But someone did say you actually misspelled his name. So, I went back and changed it in the book. Not just that, but the publisher made sure every single one of these names was double-checked.So, it helps. Thank you.[01:07:31] Nathan:An audience is so helpful for that.Well, everyone should go sign up for the book. When does it come out?[01:07:36] Andrew:StopAskingQuestions.co, mid-October.[01:07:40] Nathan:Mid-October.Okay, cool. Right about the same time that this episode will drop. So, it’ll be perfect. Alright, Andrew. Thanks so much for coming on.[01:07:47] Andrew:Thanks Nathan.

Nick deWilde is a Product Marketing Principal at Guild Education. Guild is a fast-growing startup that partners with Fortune 500 employers. Guild unlocks opportunities for America’s workforce via education and upskilling.Nick also runs his newsletter, The Jungle Gym. The Jungle Gym helps readers build a more fulfilling career that integrates work and life. Before working at Guild, Nick earned his MBA from Stanford Business School, and was a Managing Partner at Tradecraft.Nick and I talk about his relationship with Twitter, and how social media can both serve you, and be a challenge. We talk about individual brands and growing a platform. Nick also shares his thoughts about marketing yourself as an individual, and we discuss how growing an audience plays into your career.In this episode, you’ll learn: Building an audience while working full-time Three reasons people start newsletters What to do when your follower count hits a plateau Links & Resources Morning Brew Fastly Joseph Henrich, The Secret of Our Success Julian Shapiro Sahil Bloom Dickie Bush Medium Tiago Forte Building a Second Brain David Perell Write of Passage Tradecraft Guild Hacker news John Lee Dumas Packy McCormick Mario Gabriele Seth Godin Rachel Carlson On Deck Gong Matt Ragland Charli Prangley The Nathan Barry Show, featuring Kimberly Brooks Harry Stebbings The Twenty Minute VC Isa Adney Liz Fosslien, No Hard Feelings: The Secret Power of Embracing Emotions at Work Discord Reddit Pallet Craft + Commerce ConvertKit Enough Ryan Holiday James Clear Marie Forleo Ramit Sethi Nick deWilde’s Links Follow Nick on Twitter Nick’s newsletter, The Jungle Gym To tweet, or not to tweet Episode Transcript[00:00:00] Nick:I’ve tried to do things in my writing where my employer benefits from them. I talk about work a lot, and whenever I talk about hiring, I mention Gild is hiring. There are things I do to just try to make sure that it still feels worth the company’s while.[00:00:25] Nathan:In this episode, I talk to Nick deWilde, who writes a popular newsletter called The Jungle Gym. He’s got a background in product and growth, and all these things from the startup world. I just love the approach that he’s taken to writing these days.We talk about growing as newsletter. We talk about his interesting relationship with Twitter and social media. How it can really serve you and be this great thing, and then it can also be challenging. Maybe you’re spending too much time on it, or time on it in a way that’s not actually serving you or benefiting you.We talk about the rise of individual brands being used to grow a platform. It’s something I’ve been thinking a lot about, watching Morning Brew and Fastly, and some of these other companies do it. It’s just interesting whether you’re marketing as a company or an individual. It’s just a good conversation. We also talk about audience, and just how that plays into your career.He recently made the switch from a full-time role, to doing more audience-based business stuff. He was just in the middle of that journey. So, it’s a fun place and time to catch up in the conversation.Nick, welcome to the show.[00:01:33] Nick:Hey, thanks for having me, Nathan.[00:01:35] Nathan:I want to start on this article you have, that I like a lot, called, “To tweet, or not to tweet,” That got you ahead. I also happened to go to the Shakespeare festival recently, and watched them do “The Complete Works of Shakespeare, Abridged.”So, you know, I could probably pull off a good, to[00:01:50] Nick:Nice.[00:01:51] Nathan:Be or not to be speech right now. It’s in my head because I think about all the wonderful things that Twitter and an audience beyond that does for me. Then also the negative sides of it. So maybe we dive into that, but I’d also love to hear what sparked you diving in and building an audience.[00:02:11] Nick:Yeah, I’m so conflicted on Twitter, and audience building in general. Like anything, I imagine there’s a fair number of people who you talked to, who are in the writing community, who feel that way. On the one hand, Twitter does so many things for me. Especially over the past couple of years.As we’ve been in lockdown, lives have moved online. I have met and made friends with so many amazing people through Twitter that I wouldn’t have met otherwise. Same with the newsletter, but Twitter is a little bit easier to build those relationships.Twitter has definitely helped grow my bank account. So, there are clearly things that being online and participating in the online world really does for you that are valuable.I think, building an audience is super valuable.When I think about the future of work, and what will be automated and what won’t be, I really think that human beings, our greatest strength that is the hardest to copy is our ability to influence other people. This really comes from some of the thinking of author Joseph Heinrich, who looked at what is the secret of human success.It’s cultural learning. It’s our ability to essentially watch what other people do, and mimic them. We’re really good at detecting what is a real human and what’s not, and who’s someone prestigious that we should learn from, and who isn’t.I think that audience building is super valuable. So, even though I don’t love the activity of building an audience, I have gotten a lot of value out of it, and I see the value in it. So, I very much come from a conflicted spot in this. I’m very impressed by people like Julian, and Sahil, and Dickie Bush, who have grown amazing audiences.Some days I aspire to 10X my audience, and some days I’m just like, please let me be a monk and live in seclusion.[00:04:20] Nathan:Well? Okay. So I had a Twitter thread last week that I did It was on company culture for remote teams, and I’ve had some that like take off and do well before, but this was like 1300 retweets, like almost a million impressions, a level of taking off. And on one hand I was like, this is amazing.And the other, I like checked the notifications and the replies so many times, and it was fascinating watching it go from like my circle to the next circle, out to the next circle out. And like, we’re still in like positive replies, happy. Oh, build on it, refine it. And then like the one circle past that, which it took about, let’s say 12 to 18 hours to get to[00:05:06] Nick:Yeah[00:05:06] Nathan:And that was the. This guy’s an idiot. I’d never want to work at that company. you know, like all like the, the haters and the non from there, and then it like dies out and this is weird arc of his, we should graph it, but it just made me think of, is this something that I want to do and want, had I added thousands of Twitter followers?I think I could recreate it. Like maybe one in five attempts would like hit that big. Who knows. but I wrestle with the exact question of like, do I want this?[00:05:36] Nick:You and you’re, you’re just, you’re like jacked up on dopamine. You’re like, you’re, you’re sort of you’re you, you, you start just imagining all the good things that will come from this. I should be doing this all the time. Like, you know, I, I mean, I think it’s, it’s sort of pre progressive problems, right?Like, like there’s, there’s the problem of like having a smaller audience and like putting something out into the ether and then, this, this kind of, getting no response, right. That, that, that’s the first thing that, that actually like most people kind of deal with. Right. And, and, and that’s, that’s a weird thing because it’s like, it’s like, you’re, you’re then judging the quality of your ideas based on the ability of, based on basically your, your audience’s response and, and realizing like, you’re not actually talking to your audience, you’re talking to.Subsection that Twitter has decided that you can talk to at that specific point in time. And so, and then you’re basically judging your own ideas based off that. And if, if your idea is like, I think, I think when you hit a certain bar of audience, like you can, you can share ideas that are, pretty complex and nuanced and like you’ll, you’ll find some, some sort of interest for it and it has a potential to take off, but like there there’s stuff where if it’s kind of interesting and nuanced there, isn’t really kind of a built in audience for it.And people don’t really have the time to like always dig in and kind of engage and try to like, find what’s at the kernel of, it’s why I like newsletters a lot more than I like tweeting. But, but, but, but I think, I think what you’re, you know, then there’s, there’s, there’s the problem where once you get big enough, like you’re now being your ideas are being put in front of a bunch of people who like you didn’t intend them for.And those people for some reason have decided to invite into their lives, like conflict with strangers on the internet, because[00:07:19] Nathan:That’s like a primary goal,[00:07:21] Nick:Right, right. It’s like, it’s it. It’s what gives them a great day. Right. And, and, and so, so yeah, it’s, it’s such a weird thing. And so I, like, I mean, I, I think about this with like, I equate Twitter, often to, to kind of, like refined sugar, right.With refined sugar, right. It’s it’s, it’s what we call supernormal stimuli. Right. It, it, it, or super, super normal stimulus. and, and what that is, is basically something that like replaces some natural, like evolutionary desire you have with something kind of artificial that just sends your brain on like overdrive seeking that thing, seeking that thing over and over.And, and that is. That’s what Twitter is. It’s, it’s, it’s refined status instead of refined sugar. And that refined status is like, it just, it takes this thing that you normally do, which is like seek, prestige from your, your tribal group, which was a really good thing to do to make sure that you, you know, ate a good meal.And it, and it puts that into, into this crazy overdrive and it like, it centers your brain around it, and it’s, it’s such a, it’s a really powerful thing. And so I, you know, again, right, it’s like, there’s all these great gifts that come from Twitter and then there’s, then there are all these drawbacks and it’s, it’s almost like perfect equilibrium of, should you do it or should you not?And I don’t begrudge anyone either way for their decision.[00:08:46] Nathan:What I always wonder is if I could only have the benefits, like, is there a way let’s say that you don’t doom scroll Twitter with the latest news and whatever’s going wrong, or whatever, latest Twitter fight there is. Maybe you do in a separate app publish these like smart tweets or brilliant threads that are going to get all this attention.And you do one of those every day, but then like you jump in an hour later and respond to a bunch of comments and then like the next day you do it again for 30 minutes and then like, that’s it. And you just bat, like, there is this world where you could own Twitter rather than Twitter owning you, but like, are you capable of it?Do you have the self-discipline to pull that off?[00:09:33] Nick:Totally. And, and I, and I think, I think like, you know, I I’ve talked, I think Julian about this and I think he uses like tweet deck for it. And I think, I think there are ways you can do it. Right. I like for awhile, I was good at like, I would tweet in the morning and then I would like uninstalled the app off my phone.So I wouldn’t look at it. and like, there are things that you can do. it’s just, it’s just really hard because I think to some degree what Twitter, rewards, especially when, when you’re on the audience building path. Right. I think when you’re like, tens of thousand or hundreds of thousands of followers, you, you actually have a lot more leeway to do what you want.Because, because like, you’re just, it’s likely that your tweets will work, but like when you’re building your ions, there’s, there’s something that like, it’s sort of like, there’s a Turing test that’s happening, right. People are sort of looking, are you an engaged human being? Cause I I’ve I’ve I knew some people who sort of, they, they schedule and preplan all their tweets and like, and to some degree they, they just, they don’t hit, they don’t work because it doesn’t feel real time.They’re responding in real time. So like[00:10:35] Nathan:Out of pace. You’re out of touch with what’s happening with.[00:10:38] Nick:Exactly And so, and so it’s, it’s sort of, Twitter’s kind of like looking for these weird signs of life. So I think it’s, I think it’s doable. There, there must be some way to do this, but, it’s tough. I think the, the other, the other thing that Twitter did to me, that I, disliked is, it makes me feel like my relationships are very transactional because you have these likes retweets, and like these, these, Very clear, like signals of engagement.You, you start to like, or I start to like, to like keep score. Right. And, and I, and I don’t, I like, I don’t do that anywhere else in life. I think a good, like obviously good relationships tend to start out transactional and then like, they, you kind of forget what the transactions are and like that, that’s what creates a close friendship where like, look like you may have paid from the last time I paid for you this time.It doesn’t really matter anymore because we transacted so many times, but, but Twitter, for some reason, the score always feels out there. And, and so that was, that’s really been like a little bit of a red flag to me. And I, I I try to keep a generous mindset and a generous spirit on Twitter, but I find it harder than in real life.[00:11:52] Nathan:That makes sense to me. So maybe taking a step back, and maybe we’ll wrestle with some of these, like to grow an audience or not to grow an audience questions[00:12:00] Nick:Sure[00:12:02] Nathan:What was the thing that, sparked for you? I’m like, I’m going to go start a sub stack. I’m going to actively work to build an audience.[00:12:10] Nick:Yeah, I, so I was writing on, on medium starting in like 2013, maybe. Um and and really got a lot out of it. I, I started my career out as a, as a screenwriter, so I was planning to go into the TV industry and like, and, and for, you know, for, for many reasons, found that to be, a path where like, you didn’t really control your destiny.I saw I met lots of, you know, mid thirties, you know, production assistants who were slightly bitter. And then, so I just kind of realized like, this, this wasn’t exactly a good path, for me. And so, but I, I wanted to kind of keep that like, that creativity, that like interaction with an audience, I think, you know, it, it was.And found that in writing. And so And so started publishing on medium. Um we was a great experience in terms of how quick it was to publish, but like the distribution of publishing a medium sucks, right? Like, you’re you you, you publish ones and then like you spam all your friends and like, you’re, you’re just, you’re working super hard to like push this thing and promote it.And I was like, there’s gotta be some way that’s a little bit easier. and so I actually ended up in, I think I took, I took Tiago Forte is building a second brain course that kind of like, magically grandfathered me in somehow to like David Pearl’s first um uh cohort or Write of Passage, which was awesome And like, I would say, like, I took a lot out of that, but like the biggest thing was, was like start a newsletter. and so basically I started out, I think I started out with a review even. but but anyway like started publishing. Opted in when I knew onto the email list, which I’m sure they, they may or may not appreciate it, but this is before there were tons of sales tax out.And so I felt like it wasn’t, it wasn’t that crazy. I probably wouldn’t have done that in like 20, 20, but, but w really wanted like a way to like, continually kind of interact with my audience without having to worry about like, you know, just, just kind of constantly doing the heavy promotion work.Um now that’s because I now you know posts just as a part of medium but but at least there’s those sort of a built in audience that kind of grows over time that you kind of keep with you. and, and so. doing that, it was kind of it’s kind of a mix of for work and for life.I, I was, at the time, the managing partner of a, of a, uh immersive education program called Tradecraft. And like we, we would help people make sort of complex career transitions into the startup world. And and so a lot of what I was writing was kind of about that. It was about careers. but it also tied in with, with kind of deep interests.It was sort of why I took the role in the first place. and, and what I found when I, when I moved from Tradecraft over to Guild was like that kind of nicely traveled with me. and, and I think there’s, there’s something, something really nice about a newsletter, being a kind of an appendage to your career, where, like it expands your professional identity to a certain degree.You, you can become a little bit more than just your job, especially working for, like, like a single individual company, especially if you’re, if, if the company is larger you, have to deal with a lot of like coordination challenges. there there’s a lot of bureaucracy that happens at a company And one of the nice things about having a newsletter is you are in charge of it. It’s like you’re the CEO of it. the product ships, when you choose to ship it and you have complete editorial say over it, and the distribution that you put into it is what you get out of it. And and there’s something really nice about that.It helped me kind of identify as a person who who, ships a lot, even when, sometimes, you know, you know, you you have to work on something at at work that takes a long time.[00:16:12] Nathan:Have you found a dress core even a strong correlation between the effort that you put in to your newsletter and your audience growth and the results that you get out, or does it feel like a more tenuous connection?[00:16:24] Nick:I think, I think there is a pretty good, like w w when I think a post is going to really hit it usually does and so I would say like, like when I put effort into, into writing something really good, I think usually it meets it meets or exceeds my expectations. And when, and when I feel like something is, I’m kind of honing in on, on a, on a post, like usually I get that too.So I think what, what can also happen. You know, sometimes you post something to hacker news and it turns out it’s somehow on the front page and like that your audience growth spikes, or like you get featured in someone else’s newsletter and your audience grows spikes. And like, there there’s a lot of activities that like, you know, I’m not doing directly to promote it, but but it just sort of, um you know, happens in a nice way.And so that’s happened, you know, more than a few times and like, that’s a pretty neat thing, but like, I think to some degree that comes from just trying a lot of different things and then like, there’s sort of like a, a second order effect of some of those things really, you know, hitting it off.[00:17:28] Nathan:Yeah, I think that’s that’s right. I knew in the early days of starting my newsletter, I felt a strong correlation between what I was working on and like the effort that I put in and the results that I got out, been been interested well at the time I do like a really epic blog post where I put of effort, you know, we’re kind of the, for, you know, off and on for weeks or months and like really a hundred and get friends to read it, all of that.Those pretty much always do really well. But what I’m surprised by is sometimes the throwaway posts really, throwing it. Like, it’s a simple idea that you flushed out into a post and you were. Hey, it’s Tuesday. I got to get something out. Like it’s sort of in that[00:18:09] Nick:Totally[00:18:09] Nathan:Sometimes those really hit.Sometimes they actually resonate. Have you had some of those that were like easy easy ones ones that hit?[00:18:18] Nick:So the, publishing cadence is I do, I do two, two posts a month and one a and it used to be, it used to be one post a month. And then I basically separated out into two. Cause I realized like it was too much to kind of condense into, into one post. And like, I wasn’t getting the. The, as many eyeballs on like the second half, so decide to pull them apart.One is kind of one big essay. And the second is a, is is of like a, a But I think of it as like, as like I do pretty deep them. So it’s actually of like a, here’s what this is about. And a little bit more like, here’s what this made me think about.And And, the, the essay is, I always spend a good amount of time on them. or at least this year I’ve spent a good amount time[00:19:05] Nathan:On all of them two hours, 20 hours, 200 hours?[00:19:11] Nick:2020 is probably probably closest. a really slow writer. And so, and so, like, I, I do, I mean, I like like write and like re-edit the first paragraph, 20 onto the next And likeI don’t either Yeah The the the the the, the, top of the like, it’s like a then like the last paragraph gets like one glance and I’m like, God, get this thing from Um don’t and I I that is the wrong thing to do, yet, somehow I do that anyway. but, but, so, so those, those posts, they tend to get, of. You know, time and care. and then what’ll happen is sometimes the, the ones that are like the link roundups, like will, will be very spiky.And I I’ll spend, you know, that’s, that’s a little bit more like a three hour thing, um or four hours or something like that. and yeah, so, and then, and then I had, I had a, a, something that I was doing when I was interviewing folks, I call it the key ring where it was like a pretty structured interview that I would do where I asked the same questions over and over again.That was, that was fun. It, it, it started taking a long time to like do the back and forth. And so I’m putting that on pause for the moment. I may pick it back up again. those are fun just cause you can, you can feature someone that, that you like and get a chance to just and hang out It’s kinda like[00:20:40] Nathan:Yeah. Those are always interesting to me. Cause I, I think about that on this podcast of asking the same questions, which I know New, I riff on the questions too or elementBut if you did, in theory, if you’re like, did you grow from a hundred subscribers to a thousand subscribers in your newsletter?And you asked that to every single person, then you could compile that over 40 episodes or 40 newsletters or whatever. like, Hey, here’s a guide on how to do it. And like, I pulled it from a whole bunch of sources. So that part of like standardized questions intrigues me. don’t love it the live, know, version of a or newsletter where it’s like, okay, it’s too formulaic.People have done super well with us formulaic, like, John Lee Dumas, who did the Podcast entrepreneur on fire. Like he went all out. He was like, this will be 20 minute episodes, we’re going to of release one a day, seven days a week and like works for him. I have no desire to do that, you[00:21:36] Nick:Totally[00:21:38] Nathan:Yeah, I don’t know. you think about the repurposing side of content like that, or is it more just about the, the upfront.[00:21:45] Nick:I’m at repurposing and, and I, it’s something that I, have like a psychological hangup about it. Like I always kind of feel like I need to be just like moving on to the next thing. The next thing, like I’ve, I’ve tried like going back and like, be like, oh, I should mind this thing for some, some tweets.And it always feels weird to do. And like, I want to write my Roundup, but I think, I think what I’ve just recognized as. Another reason why I write the newsletter is like, I want an excuse to have interesting new thoughts each month. I want essentially a performance, right. Where like, we’re like, there is a moment where like, if I, if I hadn’t been like reading and thinking each month, like, there is a moment that it will, that I will be embarrassed if I don’t do that.And like that, that’s the way I think about the newsletter. And so, and so repurposing content would be something it’s almost like an admission of defeat. which, which I don’t is is other people should think but that’s an area of my head. And so, and so I think it just like, I need to be onto doing the next thing.There’s a bunch of stuff where like, I would love to, I love ways to use the archives, my newsletter better. I think actually like stuff like this is a fun way to do it. Like through a articles and I was like, oh, there’s there’s stuff I can, I can reference from those. Um but it’s it’s, it’s tough.[00:23:05] Nathan:That makes sense. Okay. So let’s talk cadence for a second because this is one of the most popular, common, I don’t know, questions that I get from people starting newsletters. Is there, like it should be daily right now, weekly, monthly, twice a month. Can I just do quarterly? Can I grow an audience for the quarterly newsletter?You’ve settled on twice a month? What was the thought that went into that? And, and what’s your present cons on, on that particular.[00:23:33] Nick:I think. I mean, one of the weird things, which I’m like, I don’t think it’s just me, but like, like, it was like, when you, when you release a newsletter issue, like you naturally lose subscribers, but like, like, like people are reminded that like, they’re like, know you have yeah You have keys to their inbox and they’re like, like, why why did I let this And so and so like and so ideally like that, you know what I mean, then that’s gonna have a rude awakening for, I think, I think people who are like, oh, this, this thing just goes on autopilot. but, but you need something that like is going to generate more new subscribers than it will lose subscribers because I’m a slow writer, like my, my ability to write something that I think is going to generate new subscribers is like twice a month. And like, and, and, if, and if I was, you know, Paki and Mario there, I don’t know how fast they are, but like they are, they’re dedicated.They can crank out some ungodly number of words, you know, once a week, twice a week, which is super impressive. And I think if I was them, I would do that. And like, you know, I, I love still like Seth Godin writes, like, you know, I feel like he writes every day. And I think so I think if you’re, if you’re capable of doing that, like, and, and, and doesn’t lose subscribers, then like do it and set an appointment.And I think all those things are really nice, but for me, it’s like, how do I make sure that like, one it’s kinda, it’s kinda manageable with a, with like a full-time job, which is the way I’ve been doing it for a long time. Right. and need to, I think, um you know, there, there are, there are weirdnesses of having a newsletter, any full-time job at the same time.And one of those is like, You are publishing, like if your hobby was sea kayaking, right? Like, like you could do that with no one knowing that you were doing it. Right. And like, and, and there’s, there’s nothing weird about that. Or like running a marathon or something like that. like it’s clearly the thing you’re doing on the side, writing a newsletter is like, it’s it’s knowledge work that is like akin to, to, type of work that you might do in an office Right Coding[00:25:41] Nathan:Marketing copywriting, whatever your your day job[00:25:44] Nick:A hundred percent. And like, and like, if you’re putting that out on LinkedIn, like, you know, your managers managers are seeing it and like, and so there’s, there’s just like, like doing that every day would be, a weird would feel weird to me even if, even if no one else felt weird about and so, and so I feel like twice a month it feels, feels good to me.It’s also, it also just like keeps me excited to keep, to keep at it versus making feel like it’s like a daily or weekly chore. And I have like a day off, I have a week off in between so that I can like, you know, spend the weekend, not writing if I want to, which is nice.[00:26:23] Nathan:Yeah. I like the idea of timing it to your, like your cadence as a writer. What advice would you have to someone who’s in that position of, building audience on the side there, maybe they’re doing it secretly at first where they’re like awkward about it’s this may maybe self promotional, but, but at some point, if you get to any scale right. will either you’ll tell people at work about it or they’ll find out about it in some way, hopefully be supportive, but I don’t know. What advice do you give to someone who’s in that[00:26:54] Nick:First, acknowledge that there is weirdness to it. Like there, are, like there are inherent trade-offs to everything and like, and like there is there’s weirdness and if, and if you’re your, like the, the company I’ve been working for Guild, like they, like everyone has been more than supportive at it, but, of the, the work and like, but I still have a weird complex about it.You know, I think part of the reason I ended up getting the job was because of, because of the newsletter, some of the stuff I publish of like, you know, shaped our marketing strategy. So there were things where like, I’ve tried to do things in my writing where my employer benefits from them.Like, you know, whenever I talk about work a lot and whenever I talk about hiring, I mentioned Guild’s hiring, Like there, there are, there are things that I do to just try to like, make sure that it still feels worth the company’s Weill. And also, like, I think, I think I try to bring in ID.Like I try to have ideas that are useful to what I do at work. so I I wrote this, this piece on, platform branding, which was all about, companies that essentially used their employees to build audiences that, also benefit the companyAnd like, you know, we, ended up using that strategy at Guild which, which was, which was cool.And like that ended up being the strategy doc to some degree, around it, which was cool. And so so so, there’s there, there’s like ways that you can. think um you bring that in that that are, that valuable. And so I try to sort of look for those things. I, but I think, you know, acknowledged right.That there’s, good writing is vulnerable and sometimes it’s weird to be vulnerable in front of your colleagues. and, and like it’s naturally an attention seeking activity. And if like, if like there’s someone at work feels weird about you, like, will be, you know, something that they can talk about, the proverbial water cooler about like, you know, why, why you’re not doing your job and you’re, you’re off writing these letters So so there’s there there’s weirdness, but like, I think if you can make, if you can allow your company to benefit from the audience you are growing, I think that tends to be a pretty good fit[00:29:12] Nathan:What that made me think of is basically it’s going to accelerate or, magnify, whatever someone already thinks of you. So for example, if someone already thinks, like, I don’t know, next kind of. he just doesn’t contribute that much. Like is he even working half the time then if they publishing once a week, then they’re like, see proof of what I already thought. if like the executive at the company is like, Nick is one of the best hires we’ve ever made. Oh. And look now he’s like publishing and rhinos. Like he’s a thought leader as well. Like whatever they think is just going to accelerate more. And so maybe it’s looking what reputation you already have.[00:29:51] Nick:A hundred percent and it’s like, it’s like, I mean, the way I see it, and this is kind of what I wrote about in the platform, branding thing is like, I actually think that, having a bunch of employees who are, in a creator type role, um it’s like underdeveloped marketing channel. Like you essentially, you have these people who have.Hey, like, I’m going to, going to take my scarcest asset my time give it to this company. and and and now I’m going to build relationships with, with all of these thousands of people who, who listen to these ideas and like, and like that sort of just gives positive energy to the company. So, so actually, like when you compare it, even to like a, a side project that you’re coding nights and weekends, I actually think, I think companies should be really supportive of, of, of kind of audience building on the side because it really can benefit them but, but people naturally have a, there’s there’s a weird feeling about it. And so, and so you have to like, especially as a company, You know, like our, our CEO is, is, is really good at building her own audience on LinkedIn. And I think that gives everyone else some permission to like, you know write vulnerable and things like that.So I think, but I think it, it is, it is a really important thing to be able to have this kind of a group of people who are increasing the company’s sort of surface area in Serendip.[00:31:23] Nathan:Yep. I like that. I’ve wondered about doing something like that for ConvertKit. We have a handful of people on the team who are very prolific creators, for the two myself and then, our creative director, Charlie, frankly, she has like followers on YouTube and a popular channel and all of that.There’s a handful of other people who have podcasts and are, are active on Twitter. Our product managers are quite active when you talk to them about things related to ConvertKit, you know, they’re like active with customers, but I haven’t, or we haven’t taken this approach like fast or on deck, or I’m trying to think who else does it, but, but these companies where they’re like, okay, there’s 15 of us and we’re all going to.Become Twitter famous, you know, or start our thing and we’ll all drive back. Is it a strategy that you think works well?[00:32:17] Nick:The, the best example of this actually think is, I think on-deck did it, did it really has done it really well on Twitter Um I think gong is actually probably my favorite example. Um especially from a B2B what they do is like is all of their salespeople are out there, like posting content on LinkedIn, but it’s not like how great gong is.Almost has nothing to do with gum. It’s like you know, an a I’m I’m I’m grinding today. Can’t wait to get off for the weekend. It’s like, it’s like, it, it, it sort of, embodying kind of this, this, like this, the sales lifestyle. Right. And, and, and the, the engagement they get is, is crazy.Right. And like, and that, the thing is, if, so, so there’s sort of like, there’s kind of like, you can build lifestyle influencers among your employees Right But you can also. Like this idea of building up someone who is, who is a, I know this is kind of a gross word, but thought leader in the, in the, space you’re, you’re excited about.People kind of come to them, they build affinity with them. And I think you, you can build individuals as marketing channels where like starts out where like someone’s reading your posts on LinkedIn. maybe that person hosts a, a kind of invite only webinar for, for the people who engage most of them on LinkedIn.So, so then you’re building sort of deeper affinity towards that person. And, and as, as you go down the sales funnel um like marketing and sales, you actually transfer that affinity over to the company as, as like they get into the sale process. from kind of a B2B side, but like, I think you can do it also from a B to C.[00:33:49] Nathan:Do you think that a company like gone. Hired people are good at that and encouraged it, or do you think they like had the people that they hired and said like, okay everyone, this is now what we’re doing. a playbook, here’s best practices. Here’s a slack channel where you can talk about what’s working.What’s not, but like we’re this now. Get on board.[00:34:11] Nick:This is, would be a hundred percent pure speculation. What is, is someone at gong started doing this one of their salespeople and started crushing it. And they’re, you know, director of marketing was smart enough to. Hey could be doing a lot like, and B, because it’s their salespeople who do it, right.A natural incentive to do it. And so, you know, I would imagine they probably brought on a copywriter and said, Hey, if you need help, you know, crafting these posts, like you can do that It’s just, it’s such a, it’s such a virtuous right? It’s like, it’s like, because of the affinity you build with these individuals it translates to the company.And like it just sends it a bat signal out to other people who are like that, who want to build audiences, that like the company will help you do that. And they will be supportive. And like, and again, if we imagine that like, they’re like audience is this long-term career mode, it’s just like, it’s such a great gift.You can give to your employees for them to leave with like you know, like you leave ConvertKit and you have, you know, a hundred thousand subscribers or 10,000 it’s like, or whatever. Right. It’s, it’s, it’s as much of a gift as like the salary you’re giving them. It’s just, we don’t think of it that way.Cause it’s, it’s a weird thing to think about getting. From your company[00:35:27] Nathan:Yeah. I mean, that’s how we’ve handled it in that we’re very in favor of side projects. We want everyone who wants to, like, we’re not gonna force it on. But to have a way to be a, a creator on the, on the side and to have some actual reason to use ConvertKit as a customer. Because it’s so different when you’re the product and like clicking through the happy path to test something and you’re like, Hey guys, it works.Then some customers like this is really frustrating. and so that, like, it’s a very different, different, I think that it’s just interesting. You’re absolutely right about people with that. Like, Matt Reglan, who’s been on this show before he was at ConvertKit for years. joined when we were like 20,000 a month in revenues like that. when he eventually moved on to his nets, next thing, you know, he built an, a YouTube audience to like 10,000 subscribers at that point. And that was a whole thing that he’d done a lot with skills he learned at ConvertKit a lot with, you know, our creative director, Charlie, like promoting him and just, all right. But like, it still happens even we’ve got 70 people on the team and we’re talking like six are active in this way. I just wonder how much to encourage it versus how much to just say like, Hey, this is an option if you want it, but like you don’t push it any more than that[00:36:51] Nick:I mean, I think one of the interesting things, when you think about like the creator economy is like, I think the creator economy can support a lot of people, but the the challenge is like when you’re deciding, should I follow this person? there aren’t very good moats in the creator economy. And so and so one of the.Few moats you can have is like companies that you’ve worked for giving you this brand halo. Right And so, and, and, brand from your company sort of, it says this person might be a little more worth following because someone chose them now, does that true You know, don’t think so, but like, it at least sends this signal.And so I think, one, like your brand can do that for, for, for your employees, but also like I think there’s a. I think just showing that the company will pour fuel on whatever fire you’re starting, I think is like, it’s, it’s one of the best like employee value props. I think a company can have, It’s like, it’s like, look the life you want to have. Like, we, want to get you there. like, and like, and I think the kind of people who would come work for ConvertKit it should be that they want to do something in the creator space, because you’re serving creators that makes a ton That makes a ton of of sense[00:38:10] Nathan:Yeah. And we’ve definitely had people that we’ve hired, who are already creators, and that’s grown. So it, an interesting world in all the things that you could do to grow. Like a company or growing audience. I’m not sure that that’s the one would pick, but you, you see Morning Brew and, and gong in so many of others doing it and it seems to work, know? So[00:38:33] Nick:Yeah Like, I think it works for like, like select companies in select Right. And like, and there’s, and there’s probably a channel that works under and like the. way you do it for, you know, for Guild where, like we, you know, we really target, um you know, companies with huge employee populations at the very level Like like we wouldn’t do that on, on Twitter. Right. Just doesn’t make any sense, but like, would we do it on LinkedIn where like, where, you know, C-suite spends an increasing amount of time and we can directly with those individuals and maybe influence that the five to 10 people that, that matter at those companies with like, you know, one post a week.Totally. so, so it just, it kind of depends on like, um I think companies can, can kind of do it at different levels.[00:39:21] Nathan:So that’s interesting of the LinkedIn approach, which I think a lot of creators are either all in, on LinkedIn and loving You know, people have built massive lists over there, or they’re like, what’s that like, I’ll hang out in the Instagram, YouTube, Twitters of the world, you know? but if you imagine that B2B world where let’s say I’m, I’m working in sales, either as an executive, trying to get big deals done, or, you know, or as a team member, I have a meeting, we have a great conversation.We connect on LinkedIn, you know, we’re now an official connection. And now, even though you’re not going to buy my thing now, you’re like seeing my content every. Week or every few weeks. And then it’s like, oh yeah, you’re going to buy that thing from Nathan, you know, whatever B2B tool, like starts to come up.And then when I reach out again and you’re like, it’s not like, oh yeah, it’s that one sales rep that I wasted 20 minutes off on with, you know, six months ago. It’s like, oh yeah. I feel like we’re friends there. I’ve learned so much, even though it’s just been one to many communication.[00:40:25] Nick:I mean, I think the really powerful thing it’s like obviously a sales rep is incentivized to promote the product at company they work for So it’s like it’s product whether it’s in a sales call or on LinkedIn like it will not it will not move the needle for any customer.Because it’s sort of priced in that That’s what they’re expecting. But showing that you are an intellectually interesting person who has deep thoughts about the world, who is, who’s a smart person. And then the customer making the connection, man, this smart person out of all the places where they could go work has chosen to work here.[00:41:04] Nathan:Right[00:41:05] Nick:Of something, right. There must be something kind of interesting and special there. And so they built of this affinity and comfort and excitement about you and like, and, and then getting on a sales call with you, you’re at this just like this nice advantage, right? You’re, you’re, you’re now slightly a celebrity to them.Right Like and, and there’s something, you know, like when your, your email or even your company’s email then pops up in their inbox, like it’s just that much more likely to open that much more interesting. And sometimes it’s, it’s those, it’s those little things on the margin that can make all the difference.And so I think, especially when you’re talking like a, like really big enterprise sales, I actually think it’s still, a kind of, underrated strategy.[00:41:48] Nathan:Yeah, sense. talk about a, more from the creator side. Cause that was, know, we went more on the platform company side of the which, you know, someone running a company, I am intrigued in that direction, but I’m curious on the, on the creative side, how do you think about that audience as being for your career and that thing that goes with you as you between roles and giving you a future opportunities and all.[00:42:14] Nick:I think it comes to like writing a newsletter.There’s basically three reasons. You’d write a personal newsletter and earliest the way I think about it. Like it’s either passion, like, you know, I love cooking and like, this is a way I can express that side of me It’s it’s profit. I want to actually just make some side income or make this into my full income Or it’s General advancement.And maybe the relationship building kind of tithing relationship building probably ties into that. but, but in general, like the, I sort of see one things being being like the reason, like for me, at least for a long time, it’s probably been advancement. but, certainly the other two are mixed.Like I’m, you know I’m curious about, you know, turning on the profit spigot out of it And like, it certainly like I wouldn’t keep doing it if it didn’t hit the passion bucket. and so, and so I think that, that, you have to sort of figure out which of those you’re doing. I think, I think like if, if what you want to do, I think most people actually are doing it because they do want new opportunities and relationships.I think actually advancement to me is it’s actually, the best reason to do it. Um uh over the other two. And, in that world, like, you kind of want to imagine like, okay, Who is, what kind of job do I want, who is the person that I want to be at some point down the road? Who’s the gatekeeper that stands in the way of that.Whether it’s like, maybe it’s I want to publish a book at some point, right. a publisher stands in the way of that. and so what, what gets this publisher excited? Well, either, maybe I’m writing a newsletter for book publishers and this is the industry standard, but like more likely it’s like, it’s like, Hey, I built this audience that is then really exciting to a publisher.So-so I or, you know, it’s, I want to become a senior engineering manager. and so what’s going to be exciting to the VP of engineering who is going to interview me. You know, it, it could be that I have an audience full of engineers, who who like are easy to hire, maybe it’s that I just like think in a really deep level about this really complicated problem that is really important to them, but it’s, it’s sort of like, I think having that, kind of magic gatekeeper mind as as not the person you’re necessarily writing for all the time, but the, thing you’re trying to build up to, that can be a good north star in that direction.If you’re doing this, advancement thing, I still don’t think you should pick something that doesn’t light you up because it’s really, you know, it’s really hard to keep doing this, week after week when you’re grinding it out for some future version of yourself that you know, may may change.I, I think that, that that tends to be a pretty good path.[00:45:10] Nathan:Yeah, that makes a lot of sense to me and like networking connection and advancement side of things, I think is one of the best reasons to do. A lot of that. I remember like the first conference that I went to after having a blog and it being such a night and day difference. I wasn’t even a speaker at this conference, any of that, but people were like wanting to come up and talk to me because of the articles that I’ve written you.Whereas like months earlier, you know, pre blog, you go to a conference and I was shy and introverted. Like I didn’t talk to anybody. And so I was like, wow, because I published words on the internet. People will now do all the work. Like interesting people will come meet me instead of me having to like put out all the work.This is the best leverage ever on the same way, like podcasts and everything else Write being able to, everyone says the Podcast in there for the audience. It is right. You know, thousands of people will listen to this episode. I am more doing it because I get to meet people like you and Kimberly, who we just had on last week.And right. It’s just about meeting people. that’s so[00:46:09] Nick:It’s like it’s like you know, like I think with Podcast, it’s crazy because you like appear in somebody’s ears. Right. You’re like, literally like you’re right next to their head, you know And like and it’s it’s, just like, it’s this, it’s this wild, like intimate relationship, usually, like I’m listening, you know, on, on two X.So everyone sounds smarter than you than they would were listening to them on one X like it’s, it’s, it’s I think publishing and creating content, especially in a world where like we just live more online where like more of our interactions are, are remote. I think it’s, it’s a, it’s a pretty, it’s still sort of an underrated hack, especially in, in your career, right?Like you can, you can do. You know, you, you become inter like instantly, someone who someone wants to take a meeting with and like it’s those little, like, sort of marginal decisions, right To like chart the course of your career, right? Like, like, did, did this person meet with you or not? Were they predisposed to like you, before you came in and like, you don’t actually know which article is going to hit to make them feel that way, or which Podcast is going to, you know, which Podcast you’re going to meet, the person who, you know, might be an ex customer or investor or something like that.But like, there’s just such a powerful, you know, with that[00:47:26] Nathan:I think one of my favorite examples a people using an interview show or, you know, interviews in general to break into an industry Harry Stebbings, who does 20 minute VC, because I don’t know how old he was when he started it, but like 17, maybe I’m not[00:47:42] Nick:Totally[00:47:43] Nathan:nd he’s like, I want to break into the world of venture capital and, you know, interviewing all the biggest names at first people were saying yes to him, probably because of his hustle, because he was young.They’re just like, sure. I’ll take a chance on this kid on, your 20 minute.And[00:47:59] Nick:Now love I love people who have like, a, a 10 step plan for their career. Maybe you just, you just wanted to create a podcast. It was sort of like,[00:48:11] Nathan:Right[00:48:12] Nick:Doing this for fun, but like, not a ton of people have, have a plan. Right. like, like most people are just sort of doing stuff, but like, if you like sit down and just kind of think about it for like, like 20 minutes and you’re like, who might, I want to be like, who does that person like, like what would make me credible in that person’s eyes?Like, like how could I, you know, do that thing now. So that in two or three years, like, like Harry’s, I’ve been such a good example. Like, I, I think there, there are so many people who, who like, if they, they sat and gave that like 10 minutes and turn Twitter off, like you can just, like, you can do a lot of, you know, good, good strategy there.[00:48:52] Nathan:Well, I think can do it as a method to break into any business. So if we were like, know if you and I were 18 years old and we’re like, wouldn’t be in the music business or even right. You wanted to go into screenwriting. you with what you know now, and you and I were brainstorming how to get 18 year old you into like screenwriting, we would probably suggest starting a podcast and you interview all the screenings. In some format and it wouldn’t result in work, but then you’d imagine we have this network and this work would come from the network and you’re like, no direct connection, but then there’s a ton of indirect connections that wouldn’t have happened without it.[00:49:31] Nick:You know, it’s kind of a similar thing. We talked we’ve dragged them at Twitter at the beginning. Right. Twitter does this service for people that gives them like a feeling of prestige. Right. And like, and, and what you’re basically doing is like, it’s like, you’re giving an audience to people who don’t have time to build one for themselves.And like, you know, most of the people who are listening to this podcast are people who are building audiences in, in some way shape or form, but like most people don’t do that. Right And and so, and so you can find all sorts of people who are who are just like all the time, who like, would love to sort of rent someone else’s audience to build themselves up.And so like, and so you can be then 18 and it’s a total hack to be able to sort of bring on this screenwriter, this music industry, executive, this, you know, a VC. Right. And it’s just, it’s[00:50:23] Nathan:Right It made me realize another person on the ConvertKit team who does this really well is ISA Adney. Who’s our storyteller. she used to teach all of our webinars and workshops and, and, is branched into working on like brand development sides as he writes a lot of and else, but her personal audience, let me take a step back.If you talk to her, she’s like, know this person, or whoever at Disney or that kind of thing who worked on, you know, and just like the amount of people that she knows in the world of storytelling and film and everything else, you’re like, how do you know all these people? like, oh, I interviewed them for my newsletter, you know?And you’re just like, wait, what? And it’s like, I was going to say cartoonists, but like illustrators from, from will like draw her a birthday card. can tell us just for her, you know? And you’re like, how, and, and it just comes from this exact thing of like, oh, I just interviewed them on my newsletter, which is a fantastic newsletter, but it’s not like they came on it because she’s wildly famous.It’s that[00:51:26] Nick:It’s incredible. And I like there, there’s a couple other people I’ve seen who have like, who, who sort of, they have their, their, their full-time job, but like, on the side, right? Like, Liz Bostonian, someone I’ve known for awhile and interviewed, and she, she wrote a book called no hard feelings about emotions at work.She’s about to publish her second one and like the way she’s just like, she’s known by, by all of these people at all these different companies that like her company would be the perfect company to sell in, to sell into. you know, it’s just, it’s just there. There’s. There’s so many good things that can come a bit.I think one thing I’d advise to like, w going back to like this, how do you balance a, like a, like a newsletter and a full-time career is like don’t work for any company that doesn’t value it because because like you know, clearly there are places like Guild, like ConvertKit like there there’s so many different companies where like you can go where like, they will appreciate what you’re doing.And if you can, if you can, like, ideally, like, let’s say you love to write about cooking, right. If you can find a company where like, that is like, like, especially like building an audience around cooking, like it’s, you know, a dishware company or whatever it is, like finding that right place for not just you, but your publication, a really underrated thing, because it just makes everything so much smoother to find that right.Manager find that. Right. you know,[00:52:52] Nathan:Yeah. That makes sense. If it’s an uphill battle, like find another, another place where that’s actually a asset.[00:52:59] Nick:Someone will like it.[00:53:00] Nathan:Yeah, exactly. So maybe before we wrap up, let’s talk about the growth side. Cause everyone’s thinking about, okay, I have my newsletter and it has 100 subscribers or 500. How do I grow it to that next tier So I’m curious, what are some of the things that have worked for you on, adding 100 or 500 or a thousand subscribers at a time?[00:53:19] Nick:Twitter Twitter. You, you, you can use Twitter.[00:53:22] Nathan:Yeah[00:53:22] Nick:It’s It’s frought in many ways you can also use LinkedIn. I actually think LinkedIn is, an underrated place to do it. Like it’s to me, it’s not as stressful to write a LinkedIn post as it is to write. A tweet, it’s a little stressful, cause it’s like, it’s like, definitely definitely to your company And it’s a place where you’re in professional domain, but especially if your newsletter is somewhat professional, then I think, I think LinkedIn can be a really good place for it. and a little bit less of a pressure-filled way to do it. I probably one of the underrated things now is like, you know, I look at how many discord servers I’m suddenly in, like in in you know, months and like, I think those are probably good places to like promote.I don’t think it’s, I don’t think you can in communities, it’s harder to just be promotional. You need to sort of have earned it by, by building relationships. And so, but I think like, you know, I’m, I’m in a writing group called foster, right? Where, where like where, you know that they help with editing and like, and like everyone’s sort of publishes their stuff in there, but like that’s a great place to like, to, to sort of build a following, especially sort of early on.Obviously you can do things like hit Reddit, hit hacker news, you know, Reddit, I think I’ve been banned from like, you know, 20 different subreddits for, you know a just posting a blog post, which seemed to me. But, um and then hacker news, right? You, you, you never know. And, and, you know, getting to the top means you’re going to get barraged with terrible comments, but, I think ultimately though you kind of want something you can build, right.And this is, this is the, this is the challenge with Twitter, right? It’s like, it’s like, there is a weirdness about Twitter, but. Building an audience on Twitter Like it’s a great top of funnel for a newsletter, and same way with LinkedIn. And so it’s hard to totally steer away from those things. I think one thing I’d to try and toy with once I figure out the monetization piece, of my newsletter is I’d like to try paid ads.And there’s this weird discomfort with it with it. if what you value is value is, having an audience and people to write to and you want to grow that audience, I actually think it doesn’t need to be that literally every person you painstakingly gathered with your blood, sweat, and tears, right.It’s it’s I think there’s, there’s other stuff that you can try, but you obviously don’t want to be throwing a lot of money down the drain on, building an audience[00:55:53] Nathan:YeahI’ve, I’ve done paid ads with good results of four. I have a local newsletter called from Boise, is just for the Boise area. And in the last month we actually went to a thousand subscribers and we doubled to a little over 2000 subscribers, almost entirely with ads. So like no ads to a thousand and, ads worked well, you know, and it helps to have the hyper-local targeting.So I was in the same boat of like, hadn’t played with it before. And, you know, at, I think we paid between $2 and two 50 a subscriber,[00:56:25] Nick:Facebook.[00:56:26] Nathan:Yeah, Facebook and Instagram. So we’ll play with it more. What are you thinking maybe we’ll end on this question. What do you thinking for on the newsletter?What are you paid? Is it a A A book? What other things are coming up?[00:56:39] Nick:It took me a while to find something I was comfortable with on modernization paid, never, appealed that much to me. just because there, there are some people who I like I will pay for their ideas, but like, overwhelmed with Content. that like, usually when I’m paying for, for, for, for a newsletter, it’s because I really liked the person, like their, their, just their style of analysis.I can’t get anywhere else. but, but, but the competitive dynamics of newsletter sort of, to me, like they’ll, they’ll kind of always be someone who something close to what you do for free. And so, and so that, that always kinda, didn’t appeal to me as much. Like I think of it as like, This audience, that you’re kind of building affinity with over time and like, and can you, ideally sort of find, build something or find something that’s going to be really valuable to them.So I actually, literally just this morning, teamed up with this, this company called palette, to, I swear, this, this, this time it was not planned. It just, it just happened nicely, to a team at this company called pallet in pallets, been sort job boards with a bunch of and I actually worked with them on this, this kind of beta product that they’re working on, which is this idea of talent collectives. And so what we’re doing is like, it’s like basically job searching really sucks. Like you’re filling out tons of applications. You are, waiting for a long time to hear back from companies.If you are highly desirable, you’re getting a lot of recruiter spam and they’re just like barraging you. so we’re going to do, is, is put basically just an air table form where you can say, Hey, like, this is who I am. This is the kind of role I’m looking for. pallet has this, this, all these companies that they are so, so they’re going to basically, send people and you can be anonymous if you want to all sorts of stuff, but they’re to their partner companies and then and then they’ll send you sort of the intro request, like, Hey, you know, do you want to, do you want to chat with ConvertKit right.And, and, and if you do right, we’ll, we’ll make the intro, but like, you don’t have to worry about our recruiter reaching out to you because they’ve, they’ve said they won’t do that. so yeah, I think it’s cool. you know, if, if, if any of the folks listening to this are like, exploring new job opportunity.We’d love you to come check it out. I think it’ll be really neat. I think it’ll solve a challenge that a lot of people are facing. For me it felt really native. It felt like I didn’t want to do a job board because I don’t know these companies. I’m doing a newsletter about careers, and it felt really important that I’m sending people to the right place.I said, “Hey, if you sign up for this, and you take one call from a company, I’ll do a 30 minute career coaching session with you.” Even though, I’ll get paid some commission, if the person goes to one of these companies, I will really try to give them the best advice for them, because that’s what I promised to readers.When you’re thinking about monetization, it’s like find something that feels native, and not weird to your audience. I think sometimes that can be a pure paid subscription, but you can be creative in different stuff.[00:59:51] Nathan:Yeah, I think that’s good. Let’s leave it there. I’m super excited to see what comes on the monetization side. It’s probably the coolest thing about newsletters and audiences that you can monetize different ways.So, where should people go to follow you and follow your writing, and see more about what you’re up to?[01:00:07] Nick:You can follow where I have a conflicted relationship, where there are days I will post a tweet, tweet threads, and the next day I’ll feel very ashamed of it, but that’s @Nick_deWilde. Then the better place to get my thoughts, I would say, is JungleGym.Substack.com.At some point I should probably switch that to ConvertKit, but yeah, that’s another time. We’d love that, and thank you so much for having me. This has been so fun.[01:00:42] Nathan:Yeah, It’s been a great conversation and, thanks for coming on, and we’ll talk soon.[01:00:47] Nick:Awesome, Nathan.

Kimberly Brooks is a contemporary American artist and author. Kimberly integrates landscape, figuration and abstraction to address subjects of history, memory and identity. Her work has been exhibited and featured internationality.Kimberly received her bachelor’s degree in literature from U.C. Berkeley, and was Valedictorian. She has taught art as a lecturer and adjunct faculty instructor, and was a featured speaker at TEDx Fullerton.In this episode, I talk with Kimberly about her work as an artist, author, and editor. We talk about how she uses ConvertKit to reach and grow her audience. We talk about what people can learn from fine art, and apply it to their newsletters. We also cover the path to becoming a successful creator, and much more.In this episode, you’ll learn: The secret to achieving your breakthrough moment A job most creators should charge for, but rarely do What you should be doing instead of blogging Should you be posting on Instagram? Links & Resources Huffington Post ConvertKit Craft and Commerce Steve Jobs John Baldessari Adobe Photoshop Adobe Leonard Shlain Milton Glaser Macworld Walt Disney’s Imagineering Warner Music Group Seth Godin Leonardo da Vinci Arianna Huffington Huffington Post: Fine Art Later Anderson Ranch Arts Center Otis College of Art and Design Kimberly Brooks’s Links Find Kimberly on Instagram Kimberly’s website Kimberly’s Ted Talk Huffington Post article, “The Gap Logo, New Coke and the Legendary Walter Landor” Kimberly’s book, The New Oil Painting Episode Transcript[00:00:00] Kimberly:The fundamental way to learn is, you imitate, assimilate, and then you can improvise with anything. You’re going to be thwarted in the beginning many times, and you can’t give up. You have to say, “Okay, well, I don’t care if it sucks. I don’t care if I’m going to fail. If I’m gonna fail, I’m gonna fail big. Let’s just go on.”[00:00:29] Nathan:In this episode I talk to Kimberly Brooks. She is a fine artist. So, painting, she has all of her art in galleries, that whole world, which is super fascinating to me. She also plays in the creative world. Newsletters, podcasts, and interviews.She built the whole art editorial section of the Huffington Post. She built that to millions of readers. She’s done all kinds of things in the design community from the early days. So, we riff on that; Mad Men-style ad agencies in the ‘80s and ‘90s. Some great stuff.Then she brings it all the way through to talking about what she does with ConvertKit. How she sets up her sequences, and everything else, and things that people can learn from fine art, and apply to their email newsletters and sequences.So, it’s a fun episode. We have to do a part two, because we filled up all the time we had, and I think I only got through half my questions.So, anyway, I’m going to get out of the way and dive in. So, here we go.Kimberly, welcome to the show.[00:01:37] Kimberly:Thank you for having me, Nathan.[00:01:39] Nathan:There’s so many things I to talk about, because you come to the creator world from a different perspective than I do, though we both share a love for Photoshop.[00:01:50] Kimberly:Oh, yeah.[00:01:51] Nathan:We’ll start with where we met. It was at Craft and Commerce, some number of years ago.I can’t even think. Three years ago? Four?[00:02:01] Kimberly:I think it was three years ago, and it was such a random whim. I don’t even know how I ended up finding it. I fell in rabbit hole. And then I came upon ConvertKit.I was actively looking for a better way to send art show announcements. Because I’m a painter, I’m an artist.I just felt after my previous experiences, I knew how important having a subscriber-based service was. I don’t want to get too nerdy, but I didn’t really like the competitor who shall remain unnamed. But, I found you guys, and I started getting the advertisement for the conference, and it was in Boise, Idaho.And so I thought, I’ll just go. It was like a Ted conference for really creative nerdy people like me, but it was exactly what I was wanting. It was about marketing, which is really such a weird word because it’s really about sharing, and I loved the title.I loved everything about it. I met some of the people that I’m really, really close with now. Then the next year it was canceled because of the pandemic, but it was amazing, and I met you, actually.[00:03:28] Nathan:And, and we had a really fun conversation. one thing that I want to talk about, for you is the intersection between fine art, right. And painting and that world. And then now you’re also in this world of being a writer and a creator in the sense, right. You you’ve been a writer and creative for a long time, but, but it’s, it’s like a different world of the selling things to your audience.And. Earning money directly in that way. And so I want, like, I want to hear that as you like weave in and out of these two worlds and then just your experience there.[00:04:02] Kimberly:Yeah, it’s interesting. I, when I was in elementary school, we had a really competitive game of tetherball constantly going on on the playground. And it was just sort of that pole with a ball attached to a rope we would, people would line up and we would get it, and it was, see how many times, and it was just sort of like, it was very intense and I always felt like being an artist.Being an art to me was it was the pole, you know? So like my pole is art is making art and everything about what I do. I write about it. I interview people about it. I interview other artists about their work. I make paintings 90% of the time in my studio. Like, it’s all about art, you know? So that’s like the beginning.So I do see myself sashaying between different worlds. And I think everybody kind of does that. And then as the bicycle of technology was being built to use kind of like a vague reference to like Steve jobs is, you know, what happens if you put a man on a bicycle and you know, like how fast can he, as the bicycle was kind of entering our world, I thought, what if you kind of mixed art with the bicycle?You know, what, what happens if you, you know, Make an artist’s website. So I was like one of the first people I knew that made an artist’s website. And I remember, it was, I had, was having lunch with my mentor. Who’s, the late John Baldessari. He was a great, great, great artist. And, he’s famous for, you know, he burned all this stuff and graduate school and then became a conceptual painter, you know, very, you know, Howard work in, you know, conceptual anyway.So I brought my laptop to this Mexican restaurant in Venice, and I said, I wanted to show you something. I made a website and our studios were really near each other. And he said, Oh, I, I don’t know if I would do that. If I were you, I was like, why not? He said, because you’re, you’ll piss off the dealers, the galleries, the galleries, you shouldn’t be selling directly.It’s going to take away from what their job is. You know, when you hang a show and you have art in the gallery, the gallery is selling the artist and it’s their job, you know, and artists are supposed to be kind of this, you know, semi mute, black turtleneck wearing, you know, mysterious, mystical ShawMan goddess.I call it goddess on the hill. Like you’re not supposed to really get in the way of what your artists about. And so I thought, oh gosh, you know, this is, and I had put the paintings for a show was about to have. And so I started making, so my postcard for that show had the name of the show and it had the name of the website, cause no galleries had website.Then this is in like the two thousands, you know, this is a long time ago. And I remember meeting people when I handed them a postcard. If like I felt comfortable with them, I would like secretly write a password so that they could see the website,[00:07:20] Nathan:Oh was you were, you had the website, but it was[00:07:24] Kimberly:Yeah. So I password protected it. I password protected it because John Baldessari told me that it’s probably not a good idea to have a website.This is again, no artists ad website.[00:07:35] Nathan:How did the galleries and the community[00:07:37] Kimberly:The galleries didn’t have websites either. And the galleries, I remember. They started it. Like some of them had websites, but it was super janky. It was like sometimes most of the time they did an, and it was just sort of this mysterious world that 99.9, nine, 9% of the public didn’t understand.Doesn’t understand it’s better now. And you’d have to be walking down the street or you’d have to know somebody who knows somebody, you know, it’s, it was just a different world then.[00:08:08] Nathan:But did any of those negative things come about? Like, did anyone look down on you on it for having a website and for[00:08:14] Kimberly:No, no, no. Eventually I just said, screw it. And I took the password off.And, interestingly, I don’t want to date myself, but I think I already have, but the at the time flash was very. sexy. And it was like, and so artists would have, if they did have website, firstly, they would be horribly designed and they would have like a flash animation of a curtain opening and a door.And it was very like CD rom mentality. Like, you know, it was pre-internet thinking, you know, anyway, like I said, the big nerd here.[00:08:48] Nathan:Flash was big until 2000, like the iPhone 2007.[00:08:52] Kimberly:Until Steve jobs killed it, just took a knife. He took a sword and he just, during a keynote, just, you know,[00:09:01] Nathan:Yeah. Oh, and the two biggest reasons were, that the bandwidth of the phones couldn’t handle it. And then also the battery life on the phones couldn’t handle it.[00:09:10] Kimberly:Wasn’t there another reason there was another technical reason that had to do with plays well with others. I can’t remember exactly what it was,[00:09:20] Nathan:Yeah. I mean, it was a restricted technology. Like it was owned Macromedia. And so probably that apple was trying to do to get to play. And Adobe was playing hardball and apple was probably like, okay,[00:09:31] Kimberly:Yeah,[00:09:32] Nathan:You know, we’ll play this[00:09:33] Kimberly:Yeah. It was, was, it was, it was just the evolution of, you know, of Photoshop and Adobe products. And so I grew up with Adobe. I learned I was an early adopter, always, you know, I just sort of like analogy. Yeah.[00:09:49] Nathan:I want to dive into all kinds of things. I want to talk about, more in the financial world and the business of that and everything else. But back and maybe start earlier in your career.[00:10:01] Kimberly:Than elementary school.[00:10:04] Nathan:I guess we didn’t go to elementary school a little bit after elementary school. What what did the early days of your career look like[00:10:12] Kimberly:I was a, you know, I’m a first, or I guess I’m a second generation American, so, and I’m Jewish. So of course I was supposed to be a doctor. So my, we used to get, you can be anything you want just as long as you’re a surgeon first. So I got the makings of a woman’s surgeon and, you know, it was just like, as a book that was a book that I received many times in my middle school years.And then, you know, it was like, that’s great, you’re so talented. But you know, you really, you know, after you get out of medical school, you can, it was just sort of what you did in my family. And, and my father he was a well-known surgeon and he became an, I don’t want to say artist. He became a writer, so he’s a well-known writer.And he started writing. So he kind of became an artist before my eyes, you know, so as I was getting out, as I was graduating college, he published his first bestselling. That was just, and I would like sit at the book, you know, when he gave a lecture at an art gallery, because it was called art and physics.His name is Leonard Shlain so I would like sell, watch him, sell the books, you know, like give a lecture and then I would check out and I would get, take people’s cash and then give them a book, you know, at the end of the lecture. And he used to tell me, he used to say, honey, you have to be shameless.You have to be willing to just talk in front of four people. It doesn’t matter. You just need to do it. If it’s just, it was just a big, it did. It made an imprint on me because I was watching him grow out of his own discomfort zone, which I still struggle with of talking to people like instead of through your paintings or, you know, talking to an audience saying being on video, it took me six months to figure out how to be on video, but I’m getting ahead of it.So you asked me like my CR about my career. So I was an English major. I went to an English, major architecture, minor at UC Berkeley. And at the time that I was graduating, painting was considered dead. And I know that that for artists today, they don’t quite appreciate that. But after abstract expressionism, there was sort of this mood in the art world that everything had been done and like, forget about figuration was the last thing people wanted to see, you know, and I wanted to paint people.So I just figured, okay, I’m going to just do that on my own, but I’m going to, I love reading. I love writing. So I became an English major and I was valedictorian of, of the UC Berkeley English department. And so my first job, I wanted to combine my love for art and literature. So my first job was.Design. So my, so I, was mentored by a gentleman named Walter Lander, who is the founder of landlord associates. And he was sort of the west coast, Milton Glaser, Milton Glaser from a design point of view, like he was, he just recently passed in the last five or so years, but he like did the, I love New York, you know, like he’s this famous, famous graphic designer because the field of graphic design is, is relatively new.It’s relatively, it’s like a century old, you know, like th the serious field of it. And Walter was a pioneer in it. And he did, you know, my first job was like working cause I, cause I minored in architecture was, helping design the shell oil, gas station, you know,So I was doing like architecture design, and then he asked me to write speeches.And so they had, their company was kind of designed like a brain. So they had like a language division and they had like the design division, like they did the loose soon milk and they were so famous then such leaders. They had 1800 people in offices all over the world and it was like a big deal. And they had an office on a ferry boat.So that was my first job out of college. I was a speech writer for Walter and I was in the, I was in the word department. Like I think I designed, I helped name, a cigarette, you know, like was just a weird, but it was fascinating, you know? And it was meeting fascinating people. The grateful dead would like come over on the boat after it was, it was, it was a wild time at, in San Francisco in the late eighties, early nineties.Totally wild. So, So I was like, so all the designers are starting to learn Photoshop. So there was this thing called Photoshop because they were doing everything by hand, you know? And then I was like, oh, so I got Photoshop 1.0, you know, and then I had th there was no layers. So you had to do everything in alpha channels.And it’s interesting just to be a big nerd. Cause you’re a designer too, right? I mean that’s yeah. Yeah. So if you can try to imagine there was Photoshop without layers, it meant that you had to do everything inside the masking tool that’s built in that nobody really uses or knows about now called alpha channels.So I had to create everything using masks, but it was very oddly more similar to what you did with your Exacto knife and ruler, know, I still think one of the biggest, the saddest things about Photoshop. I mean, I think everybody should know it, but it has some feature bloat, but I think it kind of buries the power of alpha channels.And I think that if people knew how to use it, it would like, it’s like a little thing to know that would hugely leap them out of the more artificial aspects of doing those filters on things.[00:16:00] Nathan:Right.[00:16:01] Kimberly:Anyway, like I you have to be careful with me because I can go into real. I can crawl real deep into these nerdy things.But anyway,[00:16:08] Nathan:Are there other things from those early days of, of the graphic design art agency, like that kind of world, that you still take with you today[00:16:19] Kimberly:Thousands of Gillian percent. One of them is the four DS that every project is discover, design develop, deploy. And I know I lost that. I also saw that, like, if you could name it, you could charge it.[00:16:32] Nathan:Is there a story behind that? If you could name it, you could charge for it.[00:16:35] Kimberly:You know, you’d see these hundreds of thousands of million dollar contracts going out to these major people. And I used to have to help write the proposals and I would see how they would divide they’d phase out, like a lot of designers. Again, I don’t, I hope we’re so not too off topic, but a lot of designers will not charge for discovery.You know what I mean? Because they haven’t named it. They didn’t name it They’d Just be like, oh, let me Research all about your company. And then you’re going to pay me to give you some designs, and then I’ll give you the designs and then hopefully they’re smarter. Anyway, like I said, big, big topic.[00:17:10] Nathan:Yeah. But think there are a lot of people listening who are in the either freelance or agency space and they, provide services to newsletters or creators or they’re growing their own on the side. And I think it’s a really important point that, if you’re if you’re structuring your proposals and all your interactions with clients around the deliverable, then you’re failing to talk about a substantial portion of the work And probably the part of the work that differentiates you from the other freelancers who are just like, oh, you need a logo. And they dive like right into Photoshop or whatever tool. Whereas if you’re good at what you do, you’re probably taking a step back and looking at the whole landscape and spending probably more than half of your time in that Research discovery and learning stage rather than the deliverable stage.[00:17:56] Kimberly:It’s actually the most important time intensive stage of any project. And so not just design. I mean, I think you saw my Ted talk, the creative process in eight stages. And I think I talked about how as an artist, I don’t want to give anybody whiplash, but like you, as an artist, you have, a period of time where it’s like a rest in music where you don’t, you’re not making work.It doesn’t look like you’re doing anything on the outside, but that’s the most important part. And it’s when. Gathering, but you’re doing it in a subconscious, like in many different ways when I’m, when I’m making a painting, I’m having to listen a lot, you know, you have to listen and look and just inhale before you can exhale.So anyway, that, but I mean, we could, I think, I think we could do a whole hour on Landour. Cause that was just a, such an interesting, you know? And, and I was actually, I was actually there, I dunno. Well, you’re, you probably weren’t born, but there was a, Coke released a new design and they, they, and Landour was the leader of this new design.And I was like in the boardroom, in my. In pantyhose. Cause that’s what we that’s what, like you had aware that it was very far, it was like mad men. It was like mad men where like everybody smoked and the women were gorgeous and the men would like have these glass offices on the side of the boat. And they would like go in and light up a cigarette and call London, you know, like they were like, or Japan and, and they had, it was just extreme, chic, crazy environment, very male dominated.And I was like, I’ll often the lone woman in a room, you know, but anyway, that’s a separate side conversation and they were introducing the new Coke and it was a flop. It was like, it was like, there was a backlash against the new design because it had like big fat. It was like, whereas the old Coke kind of has that Victorian, which they still use now that, that very Sarah fee or Nate almost like your create above your head, but more, you know, whereas.Where the new version they were doing was super kind of chunky. It was like new Coke, you know, anyway. But, it was a wild experience. I wrote an essay about it and I’ll, I’ll give it to you if you, if[00:20:35] Nathan:Yeah, we’ll put it the Shona[00:20:36] Kimberly:Yeah,[00:20:38] Nathan:On time on that.[00:20:39] Kimberly:Yeah, no, the whole, here’s the thing. I wanted to be an artist, and a lot of times I believe a lot of, and I believe there’s a lot of people who have an artist inside them and a lot of times they will, work in a field that brings them near art decisions to make themselves feel better.That they’re not being an actual artist. And I was one of those people.[00:21:08] Nathan:Okay. So how did that play out for you of your you’re close to the design and that sort of[00:21:14] Kimberly:I was like, yeah, it was, I couldn’t be closer. I was like, I was like in, I was behind the curtain of Oz doing the, with the, with the best people and everything. Again, this is so long ago, but, but I felt like technology at the time, again, Photoshop was just starting. There was no whatever. I was like, you know, I needed, I need a break.I need to like push the table over. So I quit. I moved to Paris to paint for a year. I played piano in bars at night. That was like a whole other wild. We could do a whole show on that, but, you know, then I was like, well, I can’t, I’m not going to be able to make a living doing this. Like I was painting, I was sitting at the sore bone and I was like, I had this little gig in this bar, but it was a couple of Franks and I wasn’t legal in Paris.And I just had this big because of my literature background I have does such a, you know, I love you. I was so somewhat of afraid.[00:22:11] Nathan:So how old were you when you[00:22:14] Kimberly:I was in my early twenties.[00:22:16] Nathan:Okay. When you, quit and said it’s time to do painting.[00:22:20] Kimberly:Yeah. I was like, it wasn’t a straight line. And that’s another thing. Like most artists don’t like some artists grow up and everybody goes, oh, you’re so talented.Which by the way, like hate that expression. I must like tell people, like don’t ever tell people they’re talented. Say you have great raw material, you know, just say, you know, just like great mom material, but like, you have to like do it for eight hours a day in order to like express something. Great. And then, then we’ll talk about talent, but in any case, so some people have parents that say, you’re honey, you’re so talented.I want to send you to art school. I want to spend a couple hundred grand and I’m going to send you to art school. Undergrad, let’s say a good, let’s say a typical artist, a college education is this amount. And then I want you to get an MFA from Yale or the best school and have that checked off. And then I want you to go get in galleries and be an artist there’s 0.01% of artists have that route.They have parents that say, we support this. This is good. This is a good plan. I would say that’s like a very rarefied small group. Cause you have to have, well, there’s so many things that need to happen in order to have that setup. Most people, most artists, even artists that I know, like one of my good friends Enrique he was a PA getting his PhD in physics read my dad’s book, art and physics and decided he wanted to be a painter[00:23:49] Nathan:Okay,[00:23:50] Kimberly:So like, there’s a whole bunch of artists that were doctors that were lawyer, you know, that, that, that they, they were catching the train of you know, the I’m a good student, I’m a diligent worker and they, they, you get routed onto a track and then you’re on that track. And then suddenly you wake up at at 30 or whatever, and you say, you know, I’m here and I’m super successful, but this isn’t necessarily really how I want to be spending my time.You know? I mean, th this is the conversation, right? You know, how do you, how do you decide and what you can want changes in your life? You know, but if you know what you’re pull, the tether poll is like, if you know what, your deep inner core desires. are And, you know, and you, you have, you’re remotely in touch with that and you, you need to go, you need to go towards that light.You need to go towards that center then everything will radiate out from you afterwards.[00:24:58] Nathan:Was there a catalyst that pushed you, you know, you were thinking about it, you’re feeling this, but what was the thing that made you go like, all right, I’m[00:25:06] Kimberly:Well, okay. Like I said, we don’t have enough time to get into all of this, but there were, I made three huge dramatic, you know what? I don’t know. Maybe it’s a Monty Python movie, I don’t know. But like when you push the table over and you throw all the plates and you break everything, like you just come, it’s not a reboot, it’s way more violent than that.Just kind of like you take the tablecloth out and you just say I’m out of here. You know, I think I did that three times before I got closer to. You know what it is. And one of them was moving to LA after moving to Paris, I moved to New York and then, then I moved to LA and I was like, okay, this time is going to be it I’m being artist.Like, and you know, it’s a couple of years later, it’s after Paris. Like, you know, cause you have to get, you have to, I had to make money. You know, I had to make a, I had to have a job. And so I had to kind of like do, do design work and stuff like that. So when I moved to LA, my first, I went to a Mac conference, like it was like 60 booths.It was so small, like Mac was seen a teeny little thing and, and Microsoft was the big thing windows and,[00:26:18] Nathan:Yeah.[00:26:19] Kimberly:And I made a business cards and I said, it said artist. And then when I, I walked, went to this conference and I was practically like often the only woman, you know, and I would say, yeah, I’m an artist.And I know. And so the first job I got was making the first CD rom for apple computer that they said distributed to every single apple. So they distributed over 2 million copies worldwide, and my name was on it. And that kind of, that was a huge breakthrough because suddenly I was being offered insane jobs.And next thing you know, I was anyway, like, I don’t want to dwell on this because we haven’t talked about newsletters yet.[00:27:01] Nathan:That is okay. that is okay. So you just made a leap from, I went to this conference to,[00:27:08] Kimberly:Yeah, by the way speaking, we started with going to a conference.Yeah.[00:27:12] Nathan:A big deal. We are we talking about that as well, but this leap from going to the conference to your work, being on the CD,[00:27:19] Kimberly:Well, so they were, it was like, again, I was on the bleeding edge. I could not explain to my father Who would come down and visit me. In the warehouse. I, it was, it was an artist and a coder who, but they had both met in art school and they brought me on to be the creative director.And it was like, it was almost no money at first. And then it became like a bigger thing and apple, the more that apple saw it, the more they were like, wow, this is really good. so then the next conference I went to was in San Francisco was Macworld and my art was everywhere, everywhere, and I got job offers from Imagineering. They wanted me to design why the Disney, they wanted to be the head. Of Warner music was doing a new interactive division and digital don’t digital.I can’t remember the names, but it was very, it was a very heady time. It was very, it was very fun. I felt like, wow, I found this place that has it’s the intersection of art design, narrative and technology. And it was exactly where I want it to be. And that was just, that was sort of, and I set up an easel in my office, I had a lot of people working for me and it was just, it got very, it got very fancy, you know, and I, and I took a lot of, I took a lot of like what I knew at Landour to attach in this before email this before the internet.[00:28:45] Nathan:You’re talking early nineties at this point,[00:28:48] Kimberly:Yeah. Like you no, like a mid yeah. Mid nineties, you know, 96, maybe. So, yeah. So I took a lot of my, knowledge that I gleaned from working at land or like the discover design develop, deploy to whip these engineers and designers into shape, you know? And anyway, I was still stalking what I really wanted to do, you know?[00:29:10] Nathan:Okay. So tell me more about the difference between what you wanted to do and what you were doing, because you just described your art being on everything.[00:29:17] Kimberly:No, no, no, actually, honestly, honestly like I would listen to like Liz fairs, exile in Guyville, as I drove downtown by the toy factory in downtown Los Angeles back and forth, like every day, like at these, I was a big album listener.And when I was designing, I would listen to full albums and I was just like, wow, this is it. I am so excited and energized and everything. then I started studying painting again. So I started so like I had taken a hiatus. And then I got into the, Otis, which is the art school here, You know, when you get professional, when you become a professional in anything, even being an artist, there’s a, single-minded rigor focus and clarity. one brings their whole self to what they’re doing, you know? And if you know that if If you’ve been successful in anything else or anything like that, you can, if you bring that to your art, there’s literally nothing that can stop.You. You become a wire cutter. It’s like, you’re going to munch through like, I, you know, really understanding, painting in the deepest way possible. Like I was thinking if I can understand alpha channels, I can figure out how to tone a canvas. You know, just like I just, because painting is a technology, honestly.I took everything in my being to it. And that was like a third moment. Like that was like another moment I skipped some moments, but there was like where I was knocking at the door, knocking at the door. And then I knew that in my art would become the, that I had when I started painting in full force.Like not just having it in my office, but saying this is what I’m going to do. And I’m going to do it as so ferociously, like stand back, everybody, nothing is going to get in my way.[00:31:13] Nathan:So you were painting, I mean, you had is this like painting a few hours a week, a few hours a day, and then you dove into doing that, just like.[00:31:22] Kimberly:This is like 40 hours. I mean, I basically gave myself an assignment and my assignment was I was going to paint a hundred new. Because that’s the hardest thing to do as a body. Cause you have to deal with the translucency of skin. And I could literally talk about painting all day, but you have to deal with light form and shadow and thinking in three dimensions and it creates it’s.I don’t want to knock marketing and technology and the stuff that you do, but painting is that most people do, but painting is a true, like you have to really, it’s a very intellectual as well as mindful and spiritual, but it’s a very, it’s a very deep, deep, deep way to approach the world. And when you become a painter or you actually like listen to the little voice inside you that says that they want to learn this.It’s a skill, it’s a skill. And when you do that, your brain expands and your world expands and you see things differently. So it’s a very transformative thing and it takes years. It takes years and years. So my assignment was I’m going to paint a hundred nudes and, and if I have like 10 good ones, I can have a show.[00:32:41] Nathan:So I want to tie that to maybe the experience that other creators listening would have, or anyone who’s on the fence about getting started. Right. It might not be painting that they’re trying to do, but they’ve had these fits and starts of like, I’m going to, learn to code, start a podcast, start a newsletter, any of these things, you know, learning to play an instrument, whatever it is.And then like start and it goes, maybe it goes well for a week or a month, or like what, what advice would you[00:33:11] Kimberly:Isn’t there, isn’t there like a guru isn’t there like a guru in the subject that calls it, the. Who’s that guy. Do you know what I’m talking about? Yeah. Somebody told me that, cause I was saying this to somebody and they were like, oh yeah, that’s somebody’s Seth, Godin’s the dip. But yes. You know, when I was younger and all through all through my, you know, middle school and high school and college, I played piano quite seriously.I was a classical pianist and whenever I would learn a difficult piece, I would play it over and over and over again. And I would have to, like, I would start to suck. I would get better, but then I would start to suck and I’d have to walk away and then come back at it the next day before I would be able to play it perfectly.Like, I mean, you know,[00:34:01] Nathan:Yeah.[00:34:04] Kimberly:Learning an instrument actually teaches you this better than anything, because if you make a painting at first and it sucks, you can be easily thwarted, like a, you know, a drawing or whatever. But, but in order to like worry the bone of like how to get that legato, right. And that Greek piano concerto or something like you got to just sort of do it again and again, and again and again, you know, like it’s, the fundamental way to learn is you, you imitate, assimilate, and then you can improvise.So you have to like, you play these pieces. And so with anything, you’re going to be thwarted in the beginning many times and you can’t give up, you have to say, okay, well, I don’t care if it even sucks. I don’t care if I’m going to fail. If I’m gonna fail, I’m gonna fail big. Like I’m[00:34:52] Nathan:Right[00:34:52] Kimberly:Go all out.Let’s just go on.[00:34:54] Nathan:But that specific assignment that you gave yourself of painting 100 nudes, do you think that an assignment like that is a good way to go as a creator of saying this is the commitment that I’m going to make, I’m going to get to a hundred podcast episodes or I’m going to, I don’t know, write a hundred blog posts, and then I can decide if this is something I actually want to pursue.[00:35:13] Kimberly:Absolutely. I think that when you make a commitment like that, to devote your energy into building a body of work of any kind in any media, you, your life will change everything. You are going to gain skills that involve every facet of that media. So like, if you’re a podcaster and let’s say you record in iMovie you’re going to learn iMovie or whatever they, whatever they edit podcasts.In And, and I think if, you know, if Leonardo DaVinci were alive today, trusts me. He would know Photoshop He would know he would be all over this stuff, you know, he would love, he would love it in this nether world space, because there’s, I’m, I’m going off topic a little bit because there’s a little bit of a prejudice in the art world where people were thinking they were resisting the newer technological versions of artwork.But back to process, what you were saying is that if you do something in a committed way and you basically measure it and say, I’m going to do it until I get to this point, I think a hundred might be excessive, but you’re going to get the hang of it.[00:36:28] Nathan:Yeah[00:36:28] Kimberly:I mean, I haven’t mixed feelings though, about blogging cause I started a blog again, when I was, really getting into.Consuming. I mean, consuming isn’t the right word. When I was throwing my entire body into the art world, one of the things that I did to expand my own knowledge was to write about other artists. And I think that’s also something that’s super unspoken, especially in the art world, because a lot of artists are just saying Me me me I want attention.I want to get people to focus on my show and my work, and I want a gallery and I want this and that. And I think one of the most important, aspects of breaking through to any next level of anything is generosity. Generosity of your attention to other people who are doing the same thing. And that for me, that general, I mean, I didn’t think of this.This is red, this is a in retrospect, but at the time when I look back on it, I was airlifting artists that nobody had heard of and writing about them along with other big art, you know? And so I had a successful weekly column where I was keeping a blog again, this was before social media and that’s how, and then the Huffington post came along and then I started publishing it, the, having a post.And that’s how I said, I was asked by Arianna Huffington to be the, to found an art section. And so I was like, I was perfectly positioned because I was, I was a big nerd. I had had these other experiences. I was a full-on painter. I was having shows galleries the whole thing. And then she was building this incredible Site to celebrate bloggers. And I was one of the bloggers So I had to build an audience from zero to 10 million people within two years. I didn’t have to that’s what happened.[00:38:26] Nathan:Right.I have so many things that I want to ask about in this, one thing that I want to highlight that you talked about is as you’re doing the painting, there’s the side of it, of, Research where you’re researching other painters, learning from them and all that. Most people keep that Research to themselves, right?That is not a public thing that happens. And I think a lot of the most successful creators that I see are the ones who do that recent. And, and share their notes and share that and work in public and do the interviews and all of that that you were doing. because it does a couple things. One people follow you, not only for your own work, but then also for your notes on other people.And then too, it’s incredible for meeting people. Like when you do a profile, either if they’re a, say an upcoming artist or someone who’s established either way, they’re going to be like, when you, you know, when you send them an email, they’ll like respond and be interested and engaged. And, you know, I mean, that’s a reason that I do this podcast is so that I can meet and hang out with people that I want to more aboutIt’s amazing for network.[00:39:30] Kimberly:Yes. I think you’re exactly spot on. This is no different than what I did with artists, this, except for I wasn’t involving video, I was writing about it and interviewing them. You’re right. You’re absolutely right. I also think that you can get too carried away with that though. Like you have to be careful, you have to make sure that you’re, you know, I can become easily like Clydesdale the horse.I’m like, well, that’s another month and I have to do another,[00:39:57] Nathan:It becomes more important than the art, which was the[00:40:00] Kimberly:Well, yeah,[00:40:01] Nathan:It feels more time than[00:40:02] Kimberly:Yeah, yeah. Like, so eventually I had to leave, because it was just sort of eclipsing. It became so much bigger than everything else I was doing that I had to like go, okay, this isn’t, you know, I’ve got a show coming up. I can’t devote all this time and energy. And then of course, social media kind of made it all really different.[00:40:24] Nathan:Like in what way?[00:40:25] Kimberly:Well, because not only we could, you know, writing a really thoughtful piece about an artist and looking at their work and, you know, relating it with art history. And I also found that if I could relate it to like a contemporary event, like there was this one painter who painted battle scenes and we were just going to war with Iraq, I think, anyway, we were going to war somewhere.You know, it was a horrible time, but like, I would talk about going, you know, this contemporary news event. And I would link it with the artist who was painting these battle scenes. And then seeing that it went, go.[00:41:04] Nathan:Right.[00:41:04] Kimberly:Was another, that was another big learning lesson is like, if you put a number in a headline, like 10 things, you, you should tell, you know, 10 rules for your kids and screens, you know, then people would read that more.So I could see the analytics of what people clicked on. You know, that was like a interesting learning experience. But when social media happened, then suddenly you also had to tweet it. You had to post it on Facebook and then you had to tweet about it and then it just got to be social media. here’s my take, if I could just say one thing, because I want to get it out there.I think social media is great for first impressions so that when people see you for the first time they’re going to go that person’s like a real artist or they’re a real whatever, and they’re legit. And they don’t just have like three things that they’ve said about the subject. They’ve actually like, I trust that they’ve done some deep things.Like me painting a hundred nudes, you know, like this person knows how to paint.So I think social media, it’s just so easy to get carried away. I hope one day it goes away. Is that terrible to say? I think emails should be everything. It should just go away.[00:42:14] Nathan:I don’t think it’s terrible to say at all. You have something in your Ted talk. you talked about like the compulsion to paint being taken away by your smartphone and these distractions, And I’d love for you to talk about that because I think there’s so many things of like, if I’m on Twitter or checking my email, or even interacting with the ConvertKit team 2,700 times a day, you know, it makes it so much harder as a creator.And so I like, I just want to hear more of your experience there.[00:42:45] Kimberly:Well, I mean, in order to even get into my zone mentally to paint, I have to like have at least 90 minutes where I haven’t spoken with anybody. Like I just need to kind of like clear it. Like I need to, I mean, I can be in it and I’ve got all these, you know, because people everybody’s different. Some people like beginnings, some people like middles, other people’s like ends.So you have to get in touch with which person you are, you know? So I, I love middles and beginning. I actually like all of them, but like, I’m better at certain things. So whenever I go into the studio, I have to start in paintings that are in the middle, that many going on at once. so you have to get in touch with like what time of day you’re best at.And I always begin things at the end of the day when I’m already like nice and a well-oiled machine, well-oiled creating Machine.I never begin things in the morning. I always begin. at the end of the day, I never begin paintings in the morning. I was beginning, you know, I mean, I, I’m not, I know I’m not answering your question.Your question is, compartmentalizing your time to protect it away from social media. I teach a master class and I teach a Masterclass with artists who are building their first body of work, or they, they want to build a body of work in the masterclass.I make them take an oath an Instagram oath Instagram is it’s so draining psychologically, emotionally, mentally, and the effort that you put into it that you really have to like commit and, and, and artists feel pressure to post their progress and post once a day and stuff like that.And the truth is, that algorithm, the algorithm is so fraught right now because you really only see the last 20 people that you liked more often than not. And you’re not, it it’s just, it’s not healthy. It’s not healthy for a visual artist Because you’ll be on it. You check it like a diabetic checking their insulin level.It’s just like, oh, did it get enough? Likes all that. It’s like, Ugh. So I use, later to post once a week because I don’t really want to deal with it. So I’ll do like four months at a time. But if like I have a museum show opening up on Saturday, so I have to make a post this week. And so that that’s like in my brain, oh God, I got to make a post this week.And when my book was coming out, like that’s a whole other topic about promote, you know, how to tell people and that a book is coming out. yeah. So I just kind of look at it like, you know, kind of like a creative sinkhole,[00:45:15] Nathan:Yeah. And so it[00:45:15] Kimberly:So it[00:45:15] Nathan:Makes sense to avoid it. I think we hear that advice from a lot of talented creators and it’s easy to be like, yeah. Yeah. But I can, I’m the person who can sit down and write with a moment’s notice, you know? And then you you get totally stuck on writer’s block or whatever thing, because you’re like, you actually didn’t create that space.And, like you talked about in the Ted talk of that time to like daydream and to actually be there, present with yourself and your thoughts.[00:45:42] Kimberly:Yeah, it’s true. I mean, there’s this thing in neuroscience called empathetic mirroring. Do you know about[00:45:48] Nathan:I don’t know.[00:45:49] Kimberly:It’s this, it’s like when you see somebody, for example, write on a chalkboard, the neurons in your brain, I’m not going to say this. Right? So if a neuroscientist says I’m like slightly wrong, but like, it, it, it has this effect where you feel like you’re doing it, you know, like, and it’s, that’s why people love to watch people write things.That’s why a chalkboard is an excellent device for, I actually have a chalkboard in my office because I started to. Take videos of me make with my talking points of me writing it on a chalkboard, because even though it’s considered like, you know, yesteryear technology, it actually helps people receive the information better to see it written[00:46:34] Nathan:Rather than being next[00:46:36] Kimberly:Rather than just show a PowerPoint slide.Yeah. And so this, the act of seeing it rhythm, but so if, if you think about the power of empathetic mirroring, that’s going on in your brain, when you look at something happening, think about how much it can pollute your brain. If you’re watching a stream of all these things happening in your Instagram feed or your Facebook feed, it’s like dangerous.Like you have to be protective of what is going inside your mind. It’s that they say like garbage in, garbage out, you know,[00:47:04] Nathan:I want to hear about you getting into the world of, of like teaching classes and that side of it, and then you have a book as well. There’s a lot.[00:47:12] Kimberly:Oh yes. So I have this book,[00:47:15] Nathan:There[00:47:15] Kimberly:So, you know, around a decade into, you know, being a serious painter, I started to feel bad from the fumes because painting isn’t really taught the way other things are taught. Painting is sort of like, there’s, there’s been this somewhat mystical, you know, here’s a bunch of art supplies go to the art store and then let’s see what you come up with.And then the, the, the classes tend to be more about critiques, about what you’ve done versus about,[00:47:45] Nathan:How do something.[00:47:46] Kimberly:About the, the true, true granular house, you know, the, how, like the basics, like things that you should know. And, so I started to get sick and I happened to be the arts editor at the time of the Huffington post.And I reached out to, and blogging was a very interesting, it was around 2004 or five, I think. Maybe, maybe it was a little bit later, but it was an interesting time because other people were thinking what I was thinking and I could see it in search for it. Whereas I couldn’t, I couldn’t have done that a decade earlier.And so I would reach out to leaders in the field, scientists, whatnot, to write about this topic of safety, you know, like that. And, but then when I read and I had, by the way, been consuming, Disneyland books, everything about painting, and I just saw this huge gaping hole of knowledge of how. Communicated. So I started writing this book all about painting and the book that I ended up publishing with Chronicle books is just one small piece of it because it was kind of too big.It was like James Joyce’s Ulysses, you know, it was like a tone. It was like a Magnum Opus. and it’s one of the key things that people don’t realize is that you don’t need to use solvent’s P many people believe that you need to have like an open can of turpentine or some kind of solvent to dip your brush and defend the oil paint.So it’s like super basic and most people when they go to the art store, and this is just my short, my short, skinny on the book. As most people, when they go to the art store, it would be like only buying canned or prepackaged. They don’t know what’s in it, you know, they don’t know like that you don’t need all those things.Like, but if you were like learning how to cook, you would know the difference between a garlic and a shallot and when to use canola oil or olive oil extra-virgin, you know, so I wanted to create, to start a book called the Y that was like Strunk and White’s elements of style, but for oil paintings. So that’s like the famous book that most writers use and just sort of shows you.And it’s funny, actually, it’s like a great book. So I wrote that book and that’s called the new oil painting and it’s published by Chronicle and it came out in June and it’s like staying at the top, like five books of oil painting, which is great, you know? So I’m very excited about that. But in any way, in that journey of writing the book, the book, the book deal I got was two years ago.It was like a while ago. And so Susan. Did that I thought, you know, I would be a fool to not have a class that went with the book. So to the summer of 2019, I had, I had like four solo exhibitions in a row and I thought, okay, I’m going to devote six months and I’m going to record videos and I’m going to do that.You know? So I created this class that I wish that I had, and it was way bigger than the book. It was like everything I’ve ever thought about oil painting and that’s called oil painting, fluency and flow. And, so yeah, so I launched a class, so the classes are out there[00:50:52] Nathan:Are the classes something that, you know, you’re teaching in an online course? Are you there in person or through a partnership with.[00:50:58] Kimberly:So once I, once I learned about. That you can oil paint anywhere like you, Nathan tomorrow could decide, you know what? I w I’ve got an artist in me. I want to, I want to learn how to paint and you could set it up next year, you know, like in a little side table next to your computer, and there would be no fumes, no nothing.And it’s much better for the environment it’s not made out of plastic. It’s like, you know, you could do it. So I wanted to get the word out. And, so my first class is, and so I was started teaching at major institutions. So the Anderson ranch in Colorado and the Otis where I actually took lessons, I taught there.And then, I just thought to myself, you know, this is highly inefficient because I have to like schlep over there and go there for, you know, hours at a time. And I could reach so many more people if I recorded. Instruction. And so I made these recordings, that’s a hybrid of recordings and live sessions and critiques.And I have, you know, I have about 78 students right now. They’re from all over the world and it’s like the boast enriching wonderful, fabulous thing I’ve ever done[00:52:08] Nathan:Yeah.[00:52:09] Kimberly:To being an artist, you know,[00:52:11] Nathan:And so how does that interact with the newsletter that you have?[00:52:14] Kimberly:Well, I mean, so all of my experience, just as an artist has taught me that you, your value that you bring to any situation is the people that you can tell about what you do. It’s like a tree falls in the forest. Nobody knows you’re having a show. You know, you can’t just rely on your art dealer.And the The dynamic has changed where. People don’t have one, rarely do people have one gallery that represents them. And then they’ve got a bunch of satellite galleries. So you kind of have to be a little bit more entrepreneurial as an artist. And so you need to gather an email list. And so I stopped blogging and instead I have a newsletter because I want, you know, and I I have a narrative of stories that I tell about creativity about, about like I’ll crawl deeply inside the making of a single painting of mine, or maybe another one.And I, and each email I send out, I spend a lot of time on, and it’s like a work of art by itself because it’s, again, it may be a different thing. a newsletter may be slightly different than a blog, but it’s still words and image and it’s just how. It’s like another work of art, it’s another work of art.And I love, using ConvertKit. I mean, I really, really do I tell people about it. I tell people about it all the time, because I think it’s, it’s the first software I’ve encountered that, allows you to very easily create a sequence. And, you know, you can I tell people, I say like, if you want to think about it, you could unspool Tolstoy’s war and peace.If you wanted, like you could, every week you could give like a little section and you can start at the beginning and it takes the pressure off needing to constantly have every email be a first impression. So you can really get, let people to get, to know you in a much deeper, more personal way, because you create a sequence of letters to them that[00:54:23] Nathan:Right[00:54:24] Kimberly:Over time.[00:54:24] Nathan:Well, I think that’s a really important point about starting at the beginning, because when you’re sending these one-off emails to your newsletter, you don’t know where people are joining. Some people for years and other people that is the very first thing. And so every time I find myself adding these caveats are like, Hey, if you’re new here, you know, any of those things and with a, an email sequence, you know, the automated series, it starts at the beginning every time and it works people through it.And so I’ve had that. I’ve had so much fun creating those because you can chip away at them. Like I have one that I’m kind of writing now on, I guess it’s on personal finance, you know? And it’s just things that I wish that I had known as like, Moderately successful creator. Like, Hey, you’re now earning a full-time living, what what’s next?And so I can just write about that when I feel like it and add to this, that’s now like 10 or 12 emails long.[00:55:20] Kimberly:And what’s your frequent.[00:55:22] Nathan:That one I said to every week, but if I don’t write for it, everyone just kind of pulls up at the end and weights, you know, for the next email. So it’s 10 emails And then I add to it. And so like last week I didn’t add a new one. And so now there’s like a hundred people that are all the way at the end and they didn’t get an email last week,[00:55:41] Kimberly:Yeah, no, I have that situation. I have a two year sequence[00:55:45] Nathan:Oh, wow.[00:55:45] Kimberly:I mean, I know like I sound, I probably seem super extroverted and voluble and everything like that, but like, I, I, it’s very difficult for me to sell. It’s very, it’s very not. It’s not cool for an artist to be. So like, I mean, it’s just hard.It’s also just hard for me. It’s my personality. Like I even posting on Instagram is like a stressful thing for me. It’s like, did I get everything that, you know, like I just, it’s just not, I’m not one of those people that just casually throw stuff out there. I just, I’m very thoughtful and I want it, you know, it to be meaningful.And, but anyway, I was having trouble announcing that a workshop was over. Like serious trouble. Like I would put it off and I’d say, I can’t do it. I can’t press the send button. Like I just, even though you have the schedule feature on the broadcast, I was like, I can’t do it. I can’t do it. And you know, I, I can’t remember the name of the marketing guru who was, have the five day sequence or, you know, basically a launch sequence is a series of emails where you first email is all about it.The second email might address one’s reservations about it. The third Emile email might be testimonials. And then the fourth and fifth email are like last chance to get it. Like that to me is like, I would rather have needle eyes surgery than do that, you know, so I built it in, so I basically have the sequence where every quarter there’s a launch sequence.Is that crazy[00:57:13] Nathan:No, it’s fantastic[00:57:14] Kimberly:Because then, so, so that way, like I can just set it and forget it, like back to the Crock-Pot thinking like, you know, like, you know, just set it and forget it. You’re going to sign up. You’re going to get an announcement for a walk shop, a workshop a couple months after you’ve gotten to know me.[00:57:30] Nathan:Do you think that, well actually I guess really quick, the thing that I love about that is you can be completely immersed in your painting, right? And there you are selling a workshop and you’re like, you don’t, you have to think about it or know about it. Cause you did that work once and now you’ve finished a whole day of, of painting.Start something new at the end of the day. Cause that’s the way that you roll. And then also you can say like finish up and check those sales and check that engagement. See, oh, people.[00:57:58] Kimberly:Yyeah, yeah. I mean, it’s, it’s just, it’s I think people before they’re going to buy anything, need to feel. Most people need to feel, you know, a level of comfort about what that person is about. so, you know, I haven’t touched you tube. I haven’t really, I honestly, I haven’t made, I haven’t made a huge effort because I’ve had the book coming out and I F I ha I had a big exhibition in June because, I designed a series of, excuse me.I designed, I painted a series of abstract paintings, for the cover of the book, because I wanted the cover, the book to be stellar and represent like a specified stroke, like hanging in air, like, to just convey the idea of painting and not be like a landscape, because for some crazy reason, if you, if you look up oil, painting, all the books, About oil painting are so poorly designed.It’s like, it’s strange because you would think people who are artists would care about design, but it’s like pink pallet, Tino, bold 14 point font over like a green sunset. it’s[00:59:07] Nathan:Yeah, well, design and painting are not necessarily the same thing you happen to come from a world where you have a lot of this. Even those two worlds have intertwined for you a lot over your career. So it makes sense to[00:59:18] Kimberly:Yes, but, but when, when, but if you get, but the painting books, like if you see a PA a painting book that has like a landscape on it, what if you don’t like the landscape or they all have a landscape, or it has like the, the, you know, a face that’s loosely drawn with, you know, painted with turbine, you know, Alla prima anyway.I’ve had so many exhibitions and like, I have a, I have a show coming up on Saturday and I’ve got to tell people about it. So like, I have to be, I’m already out there as an artist. So I have two different sequences and newsletters. I’ve got like a workshops for people who express interest in a workshop within the main newsletter.Like if, if, like, I’ll say like I have this one great newsletter where the subject line is, who is this gorgeous woman? And then I show a picture cause they used to paint these beautiful renditions of the faces of the Egyptian mummies inside the sarcophagus, like beyond gorgeous. Like if you looked it up, you’d say, oh my God, this most beautiful painting I’ve ever seen.And it looks a lot like Francesco Clemente, which is an artist that like paint uses the same aspect ratio. It’s like, you sort of go, oh, that’s where that guy got that idea, you know? But. I’ll talk about the pigments and that they used to, like, they used to burn mummies and then take the ashes and make a pigment called mummy brown.I know that sounds really kind of gross, but like, but, but they that’s what they did. And I I’ll say like, if this interests you, you might be interested in like a workshop. then if they say yes, then they’ll go into my workshop sequence and they’ll get notified when I open them.[01:01:00] Nathan:Are there other things that you do with email and with your newsletter[01:01:04] Kimberly:Yeah. Like I, like, I really want, I really want people to easily update their preferences. So I created a jot form like that simple select, you know, check box check if you’re no longer interested in, workshops. No problem. Let me know. And I don’t get enough work. Ominous, but hopefully, hopefully you’ll put that feature in soon.[01:01:30] Nathan:We’re actually working on building that feature now. So,[01:01:33] Kimberly:Are you kidding? When does it come out[01:01:34] Nathan:It’s one of those asking where the paintings are done. It’ll be done when it’s done.[01:01:40] Kimberly:The other thing that I do is I really think gifts are important. And I think the marketer, the marketing community is really cheesy about it. Like they always do like outtakes from friends for reaction shots.And it’s just so horrible, but I mean, it’s just corny and you know who I’m talking about, but, you know, anyway, a gift is a beautiful thing because it’s a movie that plays automatically and it doesn’t have sound and. it can be so beautiful and subtle, you know, so every time I make a news that I usually have like an, it’s like a work of art to me, you know?And sometimes if I want to emphasize a word, I’ll paint a picture of that word and I’ll integrate it in it. So like I really spend, I really love making them special. Yeah. I have one about the creative process and about not, not the Ted talk that you saw, but like I have one that’s on the lead up to talking about the masterclass.Where it’s called the curse of perfection. And I show, I talk about how, when I was a kid, my mother used to always like, she would sometimes wear like super smudge makeup and it was psych, it was called the smoky eye. I mean, they still do it now, but now the beauty people make it super specific, but then it was not that it was a little bit more like, woo.And I found a beautiful GIF of like a smokey eye, like slowly opening and closing. And I then go off on this whole subject about how, you know, it’s as a painter, you have to let go of that, of the chains of perfection. You have to let it go in order to.[01:03:22] Nathan:Yeah. Well, I love that you’re taking a medium that you know, of email or gifts or any of these things that a lot of people use in one way. And you’re bringing those styles in that like class and sophistication and really just the level of effort. I think a lot of people are like hearing. Oh, I’m supposed to have, images or gifts.I’m supposed to be funny. And so they just look for something and slap it in there. And there’s a level of effort that’s not happening there, but because you’re doing these automated sequences and you know that if you put this effort into it, it will last and work for you for years, then it’s worth it.You can do a custom painted, you know, word or something like that to illustrate a point.[01:04:04] Kimberly:I mean, I have the luxury of having hundreds of paintings, and pieces of paintings, and video of—there’s nothing sexier and more beautiful than watching somebody mix paint. There’s literally nothing more gorgeous than that—So, I’m lucky.And I understand that other creators have to find other things, but there’s a way to do things that have like a metaphorical—I here’s what I would say. I would recommend that people seek to enhance their ability to think in metaphor when they write.So if they’re gonna talk about a subject, and they’re talking about a roadblock, instead of drawing a boulder on a road, find some other image or GIF. I use a lot of GIFs from ballet. You can find beautiful GIFs just by searching “Swan Lake” GIF, and it implies a physical movement.It goes back into that empathetic mirroring, where you feel that your own body is doing these movements that are surrounding this idea. It’s not directly about what you’re talking about, but it’s like a little bit to the left, or it’s just kind of a metaphorical version of it. It creates the space in between what you’re literally saying, and what you’re actually seeing that ignites the imagination and the view.[01:05:35] Nathan:Yeah. I love that. Just putting that extra bit of effort into defining the thing that’s adjacent, rather than blatantly the first thing that came to mind. I think that makes a huge difference.[01:05:46] Kimberly:Yeah,[01:05:46] Nathan:We need to do a part two, because I have like 25 more questions to ask you, and we’re out of time.[01:05:52] Kimberly:I’m in. I’m in.[01:05:54] Nathan:This has been amazing. Where should people go to subscribe to the newsletter?[01:05:58] Kimberly:They should go to KimberlyBrooks.com. The newsletter’s right there in the footer and on the top. I really love communicating this way, and it’s been an honor to be on this podcast, because I really love the product you’ve created. I really couldn’t do it without you—without ConvertKit.So, I just, I’m such a fan, and I’m an evangelist, so kudos to you.[01:06:19] Nathan:Wow, thank you.Well, we’re excited to host Craft and Commerce again in 2022, and we can have a reunion then. It’ll be great.[01:06:28] Kimberly:Fantastic. Thank you so much.[01:06:30] Nathan:Yeah. Thanks for coming on.

My guest on this episode is music industry veteran, Jay Gilbert. Jay wears a lot of hats. He’s a musician, photographer, marketer, speaker, and music executive. Jay has worked as a creative consultant to many record companies and artists. He hosts The Music Biz Weekly Podcast, is a Co-founder of Label Logic, and runs the weekly music newsletter Your Morning Coffee.Label Logic helps artists, managers, and labels grow their audience and optimize their presence across all platforms. Jay’s newsletter is curated to give a weekly snapshot of the new music business. It’s everything you need to know, delivered to your inbox every Friday morning.I talk with Jay about his shift to being a content creator. We talk about life as a musician, working in the music industry, and being a photographer. We also talk about his management company, and his advice for creators wanting to build their audience. Jay also shares some behind the scenes stories, and much more.In this episode, you’ll learn: Simple hacks to grow your newsletter Defining and reaching your target audience Low-budget tricks to instantly add new subscribers Jay’s #1 metric for becoming a successful creator Links & Resources ConvertKit Ben Barnes People Jeff Moscow Travis Tritt Ali Abdaal ConvertKit’s Creator Sessions Music Connect (MRC) Chartmetric Viberate Soundcharts Pollstar Cherie Hu Amber Horsburgh Glenn Peoples Bobby Owsinski Bruce Houghton Hypebot Sound & Vision Music Technology Policy Nancy Wilson Roblox Jay Gilbert’s Links Follow Jay on Twitter Your Morning Coffee newsletter Ben Barnes 11:11 on People.com JayGilbert.net Label Logic The Music Biz Weekly Podcast Episode Transcript[00:00:00] Jay:The harder I work, the luckier I get. You make your own luck. You see these people, and you’re like, “Wow, that guy just blew up on TikTok or, Twitch, or on Spotify, or Apple Music!” Sometimes that happens. Not very often, and it usually it’s a lot of hard work.[00:00:26] Nathan:In this episode, I talk to Jay Gilbert. Jay’s a music industry veteran. He’s been at it for a very long time. What I love is that he’s also made this shift into being a content creator, as well as being a musician and a photographer. So many incredible things. He’s got this newsletter about the music industry called Your Morning Coffee, and he’s grown into over 15,000 subscribers.It’s the thing that everyone in the music industry is reading every Friday morning. We talk about how he grew that, his passion for the music industry, how the industry has shifted, what’s working, what’s not. He also runs a management company called Label Logic where they’re partnering with, artists and managers, and doing these album releases, and so much else.He’s got all these behind the scenes stories, and a lot of advice that is not only for the music industry, but also for any creator looking to build an audience, and endure long enough to get noticed, and to build a brand and everything else. It’s really good towards the end.I also sneak in some selfish questions about what would he do to grow ConvertKit; what’s his advice for ConvertKit entering the music industry.Jay, welcome to the show.[00:01:39] Jay:Hey, thanks for having me, Nathan. Good morning.[00:01:41] Nathan:Good morning.We’ll dive into some of your background, what you’re working on now, but you actually had a pretty big project launch today.What did you launch today?[00:01:54] Jay:Well, when you launch a big project, sometimes it’s like a wedding. You have all this planning, planning, planning, and then boom, there it is. It was pretty exciting this morning. We’ve had to keep quiet about this project. It’s Ben Barnes, who is a pretty famous actor, but most people don’t know he’s a brilliant singer songwriter and pianist.We’ve recorded this really great record. We’ve got some amazing videos, given his relationships in that area. They’re quite special. We launched a window of exclusivity this morning with People Magazine.So, if you go to People.com, you’ll see. the video is debuting. It’s pretty special, and we’re really excited about it. It gets released tomorrow. The song’s called 11:11, by Ben Barnes. It’s pretty cool. I think you’ll dig it.[00:02:53] Nathan:Nice. Yeah. If anyone doesn’t recognize the name, Ben Barnes, he plays Prince Caspian. I’ve been a fan of the Narnia series and all that for a long time. I think my kids actually just rewatched Prince Caspian two weeks ago.[00:03:09] Jay:Have you seen shadow and bone yet?You got to check out shadow and bone. My, my wife and I binged watched it. And he’s, he’s brilliant in that, but it’s a really cool series.[00:03:21] Nathan:Nice. Okay. So maybe with that, of like a snapshot of, of what you just launched, Let’s talk about, a little bit about, logic[00:03:32] Jay:Sure.[00:03:33] Nathan:You know, what types of projects you do. And then we can go back to like the road to get.[00:03:38] Jay:Yeah, well, Label Logic was born out of my partner, Jeff Moscow, and I working in the major label ecosystem for years and years. And we finally got to a point where we were meeting one day for coffee and said, you know, we started our own.So we both worked at universal for a long time. He was there 20 years.I was there 18 years. I worked at Warner music, for five years managing Amazon’s business for we at ADA, globally, which was fantastic. but we decided to do our own things. It’s about seven years ago, give or take,[00:04:16] Nathan:Yeah.[00:04:17] Jay:We started talking to. Some clients that we had at universal and we sort of became the label infrastructure for some management companies.One of our long-term clients and friends is doc McGee, who you might know, manages kiss. And he managed, you know, Motley, Crue and Bon Jovi and Diana Ross and the Supremes. Anyway, doc is a mentor, a friend and a client. And we came in and one of our first projects was working with him and his stable of artists.And what was exciting about that is that you’d have some artists that were new developing artists. They’re never played live before all the way to people filling up arenas. And so the release cycles would change out and it was very dynamic and very exciting. So. That’s what Label Logic is all about. We typically are sort of the label infrastructure, for managers, some artists, you know, we also work with some labels and distributors.I think one of our most exciting projects was taking and creating this thing called resilience music Alliance, with the principals there and they signed the artists. We did, you know, the marketing and digital strategy and help them get all the planes flying in formation. And w you know, we won a Grammy last year, so it was really exciting just going from zero to 60, you know, just building something with your own two hands.[00:05:46] Nathan:Yeah. So what is the, for someone who’s outside the music industry and they’re like this. Just magic. Somehow you find artists and then somehow that goes all the way through to your album releases. When he grabbed me, things like that, like, what are the specific things that, that you’re helping out on and playing in?What, what’s your role there?[00:06:06] Jay:Yeah, good question. It really is the unsexy nuts and bolts things about setting up a release, everything from securing ISRC codes to shooting the album cover to making sure the, the album is recorded and delivered on time. It’s all the creative surrounding it. You know, all of the banners and videos and press release and bio, and there’s so much of this to do.That we organize it all. And then we help, excuse me with partners. You may need a publicist. You may need somebody to work sync licensing. You may need somebody for March, right? There are all these different things that you need to do. And we basically, we like to say that we’re planners, but we’re also problem solvers because every single project is different and has different needs.We recently launched a new album by Travis Tritt. Fantastic record. His team is button. They are experienced. So we took on really more of a, more of a planning role putting together the marketing plans. But then we have some artists that have never released music before. So it’s a little more handholding, you know, all those certain things, because it’s not about gaming the system today.It’s really more about optimization. People always come to us and they say, well, I got to get on this plane. or I want my YouTube numbers to be up and we have t-shirts printed that say a playlist is not a marketing plan, right. Because our playlist important. Sure. They are, but that’s down the road.There’s so much to do before that. And really when I talk about optimization, when it comes to YouTube or DSPs like Spotify, apple music, Pandora, Deezer, it’s not about gaming the system. It’s about optimum. Right. And when you do that optimization, whether it’s with your website, DSPs, press, any of that good things typically happen.[00:08:02] Nathan:What’s an example of some of that optimization that, works rather than, you know, maybe what people are latching onto is is a magic bullet.[00:08:12] Jay:Yeah, couple of obvious ones. Let’s take YouTube and Spotify, Spotify, because you can do more with Spotify than any other DSP. As far as you can change out your image, your banner image, your, your avatar, your artist image. You can add, I think 140 images. to your profile, you can put your social links, you can put your bio, there’s, all these things that you can do that you can’t do.Other places, not all of them.[00:08:38] Nathan:Yeah.[00:08:38] Jay:So, you know, you’d be surprised how many times we’ll go look at somebody’s Spotify profile and it’s an old image and there’s somebody in the photo that’s not even in the band anymore, or it’s just, it’s just dated. And you look at the bio and it’s, it’s dated one of the first places we look, is someone’s Spotify profile.Is it updated? YouTube is a really great example. Optimizing for YouTube is so easy and yet a lot of artists miss it. YouTube is not just a place to go drop your music. YouTube is something that, you know, through their community, through your, your artist page. So many things that you can do with that, the common mistakes we see is an obvious one.You know, the name of the videos should be artists titled. Artists title version, and they’re mixed up and they’re all over the place you want to optimize for that search, right? You want to, for example, the thumbnail, sometimes you go in and look at people’s videos and there’s literally a picture of somebody blinking is the cover of the video.[00:09:44] Nathan:Right. Cause this is what will, what YouTube selected randomly.[00:09:47] Jay:Yeah. And, and as you know, you can, they’ll give you like three or four choices and you can pick one of those, but you can upload any image you want to be on though. And so we have actually a deck that we put together on YouTube and we show these examples of like, here’s Lizzo and look at this. It’s perfect.It’s a beautiful photo of her. And it’s, and then you look at the description, you know, is there a smart URL in there? You know, so. I don’t recommend people put Spotify, apple, Pandora, Deezer, Amazon music, just put a smart URL in there. Have somebody click on that and then they can choose the platform, whether it was.Downloads, probably not physical, digital, YouTube website, all of that stuff. It’s so easy to do. And then also in that description, anything that somebody might care about, who, who shot it, who produced it? Show me the lyrics, you know, give me put all that information in there. So it’s, it’s searchable. there that’s, those are a couple of simple examples of optimization.[00:10:44] Nathan:Yeah. You know, it’s interesting. one of the earlier guests that have the show, his name’s Ali doll, and he’s a YouTuber and he’s got 2 million subscribers who’s channel and he’s just built this incredible, business. And I always think about YouTube as like him optimizing, you know, video like thumbnails and all of those details.Like obviously Lizzo is doing the same thing or really her team is doing that. Right. But it’s, it’s the exact same. game just in two different industries.[00:11:13] Jay:Yeah, it is. And another way to optimize YouTube, for example, and you can watch what you know, Justin Bieber’s doing, and you can learn a lot from those things. one of my favorite writers and marketers is Amber Horsburgh and she did kind of a breakdown of. Some of these marketing campaigns, including Justin Bieber.And one of the things that you see is something we stress all the time. YouTube optimization. You don’t just post your concept video or whatever your music video, you still have like five videos, six videos, meaning, you know, you want to have that concept video, but you also may want to lyric video. You may want a stripped down video.You may want a live video, right? there’s so many like a pseudo video. It goes by a bunch of different names, but I know you’ve seen these where it’s just the album art. And the audio bed. And sometimes people look at those and go, well, why that’s not a video? Why is that on YouTube? Well, that’s because YouTube is the number one destination to listen to music.It’s not Spotify. Right? It’s, it’s YouTube people create playlists from those, you know? so it’s really important to. Optimized for all of these platforms. And that, that means socials, you know, Facebook, Twitter, Instagram, YouTube, as well as the DSPs, as well as all of these. And again, it’s not gaming the system.The problem we run into sometimes is people will come to us and they’ll say, oh, well, you know, I, I bought these spins or I bought these lights. Well, now you’re in trouble because number one, you can get pulled off of Spotify, right? in January 750,000 tracks were pulled off of Spotify for using bots and spin farms.Right. So[00:13:05] Nathan:Quickly,[00:13:06] Jay:Very careful[00:13:07] Nathan:Someone spinning up a whole bunch of computers and bots to go listen to the song on Spotify to be like, look, I now have a million plays.[00:13:17] Jay:Right?[00:13:18] Nathan:Um[00:13:18] Jay:Yeah. But they’re not real, right.[00:13:20] Nathan:Yeah. Okay. I I’ve definitely seen that on Instagram, Twitter. But like, yeah, it makes sense that, that it exists on[00:13:28] Jay:Yeah[00:13:29] Nathan:First thing that you look at when, when I, like, when we’re looking to book an artist for a creator sessions or, or some, one of our other projects, you know, you’re, you’re, it’s that first source of credibility of like, oh, wow.That has two to 2 million plays this. Person’s getting a lot of traction.[00:13:44] Jay:But what we look at instead of looking at those numbers, we look at engagement and when you look at engagement, sometimes you see the audience grow and that’s going up, up, up. But if you don’t see the engagement growing along with it, Then you know, that those aren’t real people, because when you use bots and spin farms to Jack up these numbers, yes, it’s dangerous because it can get you in trouble, but it screws with all of your, data, which is so important, right?The, what you really want. is Engagement. You want people to like, yeah, you want people to follow, but you want people to listen, share comment. That’s real engagement, man. You get that. Uh that’s that’s the prize.[00:14:29] Nathan:Yeah. So let’s go back. as you’re getting into music, what, like, in the, in the early days, what was the hook for you? What, what brought you to the whole industry?[00:14:39] Jay:Oh, my gosh. Well, my, my family’s musical, you know, my brother, you know, he’s a Writer record producer, graphic design artists. my mom played piano. My grandfather played sax and big band. You know, I started a little high school band and ended up, you know, touring in bands and playing, writing, recording. So I kind of got to know how the sausage was made and, and I loved working in record stores.I worked for an indie record store. I worked for tower records for five years. There’s so much fun.Um and[00:15:08] Nathan:Been in the industry.[00:15:09] Jay:Yeah, I’ve always been in music and, working at universal was just such a joy. learned so much. yeah, I’ve always been surrounded by, by music ever since I was little kid.[00:15:21] Nathan:What’s something as a,[00:15:24] Jay:Oh[00:15:25] Nathan:If you’re talking to an outsider, maybe a common misconception they have, know, someone who’s a fan of music then you’re like, oh, this is actually how it works that you find yourself explaining or,[00:15:37] Jay:Oh, my gosh, we could talk for days.[00:15:39] Nathan:Yeah.[00:15:40] Jay:I wish people understood that the harder I work, the luckier, I get, you make your own luck. You know, you see these people and you’re like, wow, that guy just blew up on TikTok or, you know, Twitch or on Spotify or apple music. Sometimes that happens not very often.And it usually it’s a lot of hard work, you know? I asked an ANR person before the. You know, how do you choose who you signed to your label today with all of this data? And he said the same way. I always do. I look for that line up around the block for people to see him play, right? So it’s, it’s a new music business and we can now see with all this data what’s going on.But I think the common misconception is there’s a similar. There isn’t a silver bullet, you know, it’s, it’s a lot of hard work and it’s a lot of finding your tribe. And I say that a lot because you need to find your audience. I talk to people all the time about finding that audience and they think they know who their audience is.If you talk to any manager, artists, they, they they’ll have a sense. Like, well, my demo, my artists or my, my fan base, I mean is 25 year old. But there are three audiences, right? There’s one sales streams and downloads. So the commerce side to the butts in the seats. So when you’re touring, who’s actually out in the crowd, right.And then three, you know, kind of the social side of it. Facebook, Twitter, Instagram, those three audiences, rarely aligned completely. And there’s always something to learn. I was talking to an artist recently who thought that. Their crowd was 25 year old, females, because that’s who they saw in the crowd.But if you look at the other data, that’s not who’s quote unquote consuming their music. So there are a lot of misconceptions, but, I heard this really great line about data and analytics. It’s like a lamppost. You can use it to aluminate or you can use it to lean on. And most people use it to lean on, like, see, I told you that’s, that’s what I thought my data is.But really, if you go in and look at all this, analytics, you’ll find that there’s always something you can learn in there about your audience and how to reach your audience.[00:17:57] Nathan:I like that because I catch myself doing that of like, Let me go dig for the data that proves the point thatI already my existing worldview and that they were having that debate. Yeah. See, this is what proves it. And you can go back and, and[00:18:14] Jay:Right[00:18:15] Nathan:The data say almost whatever you want.If you come at it with that[00:18:18] Jay:Yeah, absolutely. And today there’s so many great places to find data like real great data. Like for example, you know, it used to be called SoundScan right now. It’s called MRC connect. Same thing. You can get real numbers for sales, streams, and downloads. That is so helpful. And you can see data from previous releases and kind of get a sense of that.There are these great platforms like chart, metric and vibrate and sound charts, where you can go in and see what playlist was I added to which ones, where I dropped off of what position was I in? How many times was it skipped? You know, there’s so many great data platforms out there, but it’s almost like there’s too much, you know, you need to kind of focus on what, what do you want to do?You know, some people want to route a tour, So that’s really easy. You can kind of see what markets you’re over-performing in. You can download data from Pollstar and see if you played in those markets before, you know, how did you perform? So we’re really big on data, but you kind of have to look at it carefully and decide what you’re trying to learn from it.If that makes sense.[00:19:30] Nathan:How do you think about the intersection, between the different platforms? Like, if you’re actually say we’re promoting it to her or, a new album release or something like that, what are you recommending as far as where artists build, you know, build their audience. and then, yeah. How do you think about the intersection when it actually comes time to drive?[00:19:49] Jay:Yeah. And that’s, that’s a great question because it’s so different for every artist in every release, right? So you kind of have to look where, where is my. You know, they may, maybe they’re still buying physical. Maybe you’re a jazz artist and that’s a, still a, an album format. So you want to look at Amazon.You want to look at places, indie retail, where people are buying the full album and they want to experience that way. then you look at maybe EDM or country, every kind of genre and mood has its own nuances. I think it’s really important to find out who your audience is, what their behaviors are. And then a real simple thing is when it comes to social media, so many artists today, they have so many choices and it’s not just writing and recording and touring.Now they got a post on socials and create videos and comment. I mean, it’s so much, so what we tell people is take a step back. What are you killing? Yeah, right. And a lot of them it’s Instagram, right? Some of them it’s TikTok focus on that. You don’t have to be all things to all people, you know, find out where that crowd is, where your audience is and really work that, and then kind of grow it from there.And hopefully you’ll get to a point, like we were talking about Lizzo, where you have a team surrounding you that can attack all those different platforms.[00:21:16] Nathan:Yeah, think there’s a tendency. I see this in founders and entrepreneurs and marketers, like all across the board. I’ve, we’re so used to failing at things like trying things and failing. They like tried this didn’t work and in order to continue to be a founder or a marketer and you have to try the next thing tried that didn’t work tried that didn’t work, this, it worked.[00:21:38] Jay:Yeah[00:21:39] Nathan:So then I tried this and it didn’t work and this, and it didn’t work. And you’re like, hold on. But what about the thing that did work and, you know, we move on so quickly and we see like every case study of[00:21:49] Jay:Yeah. And it’s so different per artists. So the thing that you just described as spot on, but let’s say we did that for Ben Barnes. Well, our next artist, we got to start from scratch because the things that worked for Ben probably aren’t going to work for Travis Tritt. There they’re totally different animals.So I love trying things. I love trying new platforms and, you know, there are a handful of things that really work across everything. And so you kind of start with those in your marketing plan, like. Tools is bands in town. Now everybody knows bands in town. It’s got like 55 million people have this app on their phone and it says, Hey, Nathan, you know, the accidentals are coming to your town in a couple of weeks and you’re like, oh cool.And then you can buy your ticket and stuff. They look at your music library, but what a lot of people don’t know is that you can go in there and look at how many people are attracting. Right. And usually it’s thousands. You know, you look at these artists, they don’t even know they have thousands of trackers and bands in town.Well, you can reach out to them for free and say, Hey, I’ve got a new release coming out. or I’m going to be in a, there’s a tour and I’m going to be in your area. But what’s really exciting about bands in town is that I can look at like competitive artists fan bases. So if I know that my artists. You know, then maybe there, they would appeal to the Chainsmokers crowd.I, for 5 cents an email, I can target them and say, Hey, you guys dig the chain smokers. You, you might dig this too. So there are a lot of little platforms like that, like you were talking about, which is so important. You got to try. All the time. And you know, as Paul Stanley said, the road to success, isn’t from here to success.It’s failure, failure, failure, failure, success.[00:23:37] Nathan:Yeah, for sure. Are there any trends going on in the music industry now that concern you things where like, as, as you’ve watched it develop, you’re like, I’m not sure where this is headed and I’m not sure that it’s going to be good for the artists. Good for the fans and any of those things.[00:23:51] Jay:Not a lot. I think it’s, it’s changed while we’ve been having this conversation. The music business is evolving so quickly and you know, I do a weekly podcast and newsletter for the music industry and we break down the stories every week and it’s so fascinating to me. How quickly it’s evolving. And, you know, for example, you see companies like hypnosis and primary wave and BMG buying up all of these rights.And you’re wondering like, well, they’re paying these huge multiples what’s going on here. And some of these heritage artists are getting hundreds of millions of dollars. And then in the last couple of weeks, you’ve really seen these stories about interpolation. Coming out, meaning that instead of using a sample, they’re just using the melody of a Olivia Newton, John or Taylor swift song in a new song.And it, no one’s getting sued because they’re crediting the writers and they’re paying the publishing and you may find two or three interpolations in one song. Olivia Rodriguez recently, there’s so many. Of these things that are evolving so quickly, TikTok, it just blows my mind sometimes how fast you can gain an audience there, but it’s one of the hardest platforms to gain real engagement.So you can gain those numbers, but how do you hold onto them? It reminds me of some of these artists that are on these talent shows, you know, American idol, the voice America’s got talent, whatever you got to grab that audience. Once they’re off that show, you have to engage them quickly or it’s gone. cause you’ll have huge numbers from being on those shows.But if you don’t engage with that crowd and keep them interested in, you’ll still have those big numbers of YouTube subscribers and followers. But the engagement just drops right off the cliff. So as far as the trends that concern me, I think the biggest thing we touched on, you know, people who try to buy likes, follows spins.I just, I think that’s horrible and it’s so dangerous for their career. we always tell people. We manage 20 careers. you’re, you’re managing one yours. You need to take that really seriously. And, we, we advise against trying to game the system. I have a friend of mine who’s really big in SEO search engine optimization and, he’s very good at it.And he always tells me. These people come to me and they’ve messed with their website, for example, to get it to come up in search. And he laughs and he says, look, Google’s got, Google has like 200 highly trained engineers working on this stuff. And you think you’re going to trick them with your little, you know, metadata trick, you know, maybe for 10 minutes, but it’s always best to have a plan, have a marketing plan.Optimize for everything. you do that and avoid some of these pitfalls. Yeah. Those are the things that concerned me. It’s just people trying to, find a shortcut.[00:26:58] Nathan:Yeah, that makes sense. you dropped a bunch of things in there that I, I want to talk about and dive into, but maybe starting with the music back catalogs that are being purchased, those rights, I’m always super curious about things like that, because. You know, as a creator, you’re working on things that feel like they’re in the moment.And I have a few friends who are successful authors who are pretty prolific, like they’ll write a book year, a book every other year. one friend said like, basically like putting out annuities where you have this, this thing and add you as you add to your catalog. It just. Let’s say this book is going to sell $50,000 worth copies its long tail every year.Like clockwork, time you come out with a new one, it adds that there’s another 50,000 a year, plus it gives it a little bump. And so you see creators who are these big spikes, and then that’s kind of it. You also see creators who are continually adding to the back.[00:27:54] Jay:Yeah.[00:27:55] Nathan:Like explain more for anyone who doesn’t understand on the music side, why these catalogs are so valuable and why, you know, people are paying[00:28:04] Jay:Yeah.[00:28:04] Nathan:Of millions, hundreds of[00:28:05] Jay:Yeah Well, it’s just math at this point. What’s happened is with streaming. Now there’s some predictable. There’s some planning involved. So if you have a catalog, you know, you look at like Stevie Nicks sold hers, or at least a big portion of it. And Bob Dylan, there’s a predictability now that there wasn’t before on how much revenue that’s going to generate on, on two sides, one the publishing, right?For the, for the songwriters and then the master, you know, so with that predictability comes, some of them are just banging. You know, they come in there and they say, okay, this catalog is worth this much money. And this is how much it makes over a year. Let’s say it makes a hundred thousand dollars a year.Well, we’re going to pay you for 10 years or 20 years worth and cut you a check right now. So we call those multiples and some of these companies are paying super high multiples and almost jacking up the price. It’s kind of a land grab in some respects. So. It really doesn’t help a new developing artist a lot right now.But if you’ve co-written songs with people and you’ve got music out there, There, there is money to be had there. If you want that big payoff, some people are selling off their publishing. Some people are selling it off for a term. Some people are selling their masters off and it makes sense for somebody let’s say Stevie Nicks, cause she’s in her seventies.Now it’s a state planning and she can, you know, get all of that money and help her family and whatever. So I’m not necessarily against. At all. but what I really love is watching how these companies are now going to exploit that catalog. And I mean that in the best possible way, exploited, how are they going to generate the right revenue?And that interpolations that I talked about a minute ago. That is one way, you know, there was a story last week, and they talked about primary wave having, you know, these writer’s camp. And using their top 40 or 50 tracks that they have the rights to, and having these writers write songs surrounding those melodies.And again, those writers will be credited those writers and the publishers and all of that, but that’s kind of the new trend too. So yeah[00:30:35] Nathan:Yeah that’s fascinating. it’ll be interesting to see how it keeps developing Another thing that you talked about a little bit is, uh your newsletter, which I want to get into, what, like so many people consume content, what was the thing that made you switch and say Hey, I want to be to be one of the, people on the creator side, commenting on the industry and building an audience[00:30:58] Jay:Yeah[00:30:58] Nathan:That’s like, it feels like you’ve been more of a behind the scenes guy for a long time. And now there’s a little bit of at least you’re going to be a front of house for all the behind the scenes people.[00:31:11] Jay:Yeah, no, that’s, that’s a good point. I think what happened was I had left Warner music group and I was deciding do I want to start my own company. Do I want to go back working for a major? And I got this email from Sean Rakowski who used to be the head of sales for ADA. And all it was was about a dozen of.These songs and albums that he had found that were really good. And he was sharing it with a hundred people. So I called him up and I said, this is cool, but you know, why are you doing this? And he said, well, I’m kind of between jobs. I don’t know where I’m going to go right now. And I just don’t want people to forget me and the light bulb went on and I went, I’m going to do that.So I did something you’re not supposed to do. And that is, I created an email and just basically sent it to a couple hundred people in my. my contacts, you’re typically supposed to ask for permission, but I just decided, you know what, I’m just going to do this and what do I love Well I love music and technology.So I’ll just do a recap, every week and what I knew at the time. was that People don’t like to read. I love reading stories on technology and music, but not everybody does, but they want to know what’s going on. So I put an image and then just a two, to three sentence blurb. So even if you don’t read those top dozen stories in your morning coffee, you can read that little blurb and go, oh, okay.Well, this is going on. You know, here’s some changes that here’s some platforms that are coming up. This is what’s going on with the music modernization act or NFTs or whatever. And. All of a sudden. It started to grow. And that little newsletter to a couple hundred people is now over 15,000 people and we have advertisers and now we have a weekly podcast, we’ve been doing for a year where we break down the stories.So I didn’t have this grand plan of, I’m going to create this newsletter for the industry. And no, I just didn’t want people to forget me while I was deciding. What my next career path was going to be, and it was a happy accident. I just stumbled into it. And then next thing you know, some of my favorite artists subscribed to it.Some of my favorite managers subscribed to it and they’ll send me notes. What do you think about this? And then. The last thing I’ll say on it is it wasn’t intended for business. It wasn’t intended for me to make money from, but what’s happened is people will read your morning coffee and then they’ll call me up and they’ll go.I think I need to hire Label Logic to be my label infrastructure for this. And so it’s brought us business, but that, wasn’t what it was intended for originally.[00:33:43] Nathan:Yeah, it’s fascinating how that worked. Cause you, you position yourself as the expert, the person with the pulse on the industry I mean, it’s not even like a deliberate thing. You don’t have to say that you just. Are the[00:33:56] Jay:Cool[00:33:57] Nathan:Sent, like sending out the content and people are like great, thanks for doing that.So I didn’t have to go compile it from different sources. And, and you find that you have your own platform.[00:34:07] Jay:Yeah[00:34:07] Nathan:Some, what are some of the things that worked as far as, growing it, maybe deliberate things that you put in, beyond the, organic growth and sharing[00:34:17] Jay:Yeah, I think that, the thing that really helped us is really like, if you’re a wedding photographer or a real estate agent, all of your business practically is word of mouth. And a lot of the growth that we have for your morning coffee comes from people just getting it, and forwarding it to their staff, you know, I’m saying, Hey, have you seen this?And that’s where we’ve seen that growth.I think the things that I did that really. helped Keeping it to those blurbs and not trying and having that image. People are very visual. I’ve seen other newsletters that are just a mountain of text.[00:34:53] Nathan:Yeah[00:34:53] Jay:Not many people are going to dig through that. So I wanted to make it.Very accessible to somebody who’s really busy at an airport. They can just look at it on their device and and get a sense of what’s going on. The other thing that, again, by accident, I started reaching out to some of these writers, like you had mentioned earlier, speaking with Sherry who, I reached out to Sherry, you know, I’ve had her on the podcast, we’ve had conversations.I have a great deal of respect for her in her writing people like, You know, Amber horsepower. I mentioned, Glen peoples, Bobby O Sinskey, you know, Bruce Hoten over at Hypebot. After a while I started developing these conversations in relationships and I would be on their Podcast. They would be on mine.I would write articles for Hypebot Hypebot would promote your morning coffee of the newsletter, a very symbiotic kind of relationship with all of these writers. And the level of debate and the level of communication has just enriched my life. Having these conversations with people, you know, like Amber and Glen peoples and saying, well, what do you think of this?I dunno, what do you think of this? You know, for example, I, I met this really smart young marketer, Maddie Elise, who runs her own company and she was doing some really great analysis on bots and spin farms. Like how can you tell if you’ve been bonded and we got into these conversations and she posted some really great articles online.I put them in your morning coffee. It’s been a wild ride, but it’s, it was unexpected that I would have these conversations.[00:36:36] Nathan:Well, It’s amazing how Yeah. Like in any industry, Like working in sales, the music industry has all connections and relationships.[00:36:45] Jay:Yes[00:36:46] Nathan:Could spend forever people one on one Hey I’m I’m coming to your city I’m in LA I’m in Nashville I’m in Atlanta Like now we’re in a you know like trying to get one connection into the next and coffee and everything else to try to build up that now. Or you can kind of take take a step back and say, all just going to start a newsletter and then get like, thousands and then people that follow it. And then[00:37:10] Jay:Yeah[00:37:11] Nathan:You would like really slowly be like working up relationships to get to the point that you’ve talked to is like oh, Hey, I wrote this thing.Would you mind throwing it in the newsletter And like,[00:37:22] Jay:Yeah[00:37:23] Nathan:Also come on on my podcast, let’s chat. And it’s just this shortcut to relationships and amazing.[00:37:27] Jay:Yes, absolutely. And I’m a big fan of networking, music business association conference, one of the best on the planet. You know, you go there. The, the great meetings are the ones, while you’re waiting in line at Starbucks, you know, you meet all of these people. And it’s then like at the last music business association conference, I was standing in line talking to some publicists.Well, publicists are so great because they’re on the pulse of everything. There are people like, you know, over at shore fire or the great team at rock paper, scissors who matches technology and music in their publicity campaign. And now they’re sending things to me. Hey, have you heard about this new platform?Hey, you might want to interview this person because they’ve got this new thing. And so it, it becomes this thing, but you had mentioned like sitting down and having coffee with people. That’s what I did with Amber Horsburgh I’ve. I read some of her deep cuts, things that she has online. She has done marketing at a high level.My partner, Jeff and I have done marketing at a high level. We called her up, met at the one-on-one coffee shop and just had an amazing.Chat, as you know, when you sit down with somebody who’s enthusiastic about the same things you are, whether it’s music, sports, whatever, you can talk all day. Right. And I love meeting these people and that’s kind of how, like the, your morning coffee Podcast.My, my cohost is Mike Etchart, who did sound envisioned radio. He and I can sit and talk for hours about. This, these stories. So every week we do the podcast, we record it Sunday morning at nine 30 and it goes live on Mondays. We talk for a half hour to an hour before we hit record. We just sit there and, oh my gosh.Did you see that documentary on 1971? No. Hey, have you heard that new record by, you know, Ben Barnes, whatever it is. And because we have such a passion for it. And I think that comes out in the newsletter. It’s not a dry kind of thing. and the last thing I’ll say on that is the other side, these relationships I’ve developed are like with attorneys who write stories.There’s this one guy, Chris castle, who has a website called music technology policy. And I. You know, put some of his great articles in your morning coffee, cause they’re really smart ass, you know, sassy stuff and had him on the podcast. And now I’ll call him up from time to time, you know, like what do you think of this?And it’s just, this whole kind of network is it’s really.[00:40:02] Nathan:Yeah, that’s amazing. Is there a favorite moment or something like that, where, uh or opportunity that the newsletter has created for you? Like, we talked about a lot of connections and stuff like that, but one where, you know, you’re like, Oh wow, this is, this is a fantastic opportunity that wouldn’t have come.If I hadn’t built it.[00:40:20] Jay:Oh my gosh, so many of them, but I’ll tell you, at a high level, getting to speak to people that I admire respect that that’s thrilling. But one great example recently was for our one-year anniversary of the, your morning coffee Podcast. we had Nancy Wilson from heart on and did an hour long interview with her.Now I grew up in. I grew up on heart, Nancy and I shopped at the same record stores. I saw them play live many, many times, huge fan. so that was pretty cool and knowing her as well as I do her career, her music, all of that. Mike and I had an amazing, interview with her and that’s something that we just wouldn’t have had, without this via.[00:41:10] Nathan:Yeah, that, that kind of thing is so fun of like, almost getting to have a conversation, you know, as peers and all of that with someone that you’re like[00:41:21] Jay:Yeah.[00:41:22] Nathan:However many years ago would be freaking out Right. now[00:41:25] Jay:Right. I was in the, I was in the crowd, right. Cheering along, and now we’re having a conversation about things and that’s probably the most thrilling part of your morning coffee. The newsletter and Podcast is the level of debate. The level of people that will call me and say, I disagreed with that piece.Or I’d like to write an op ed or, you know, Th that’s pretty thrilling because look like we said, this music industry’s changed while we’ve been on this call. So if you want to keep up with it, you can follow some of these great, writers. And, you know, you mentioned Sherry who, you know her, I subscribed to her Patrion.I love the research that she does. And I’ve learned so much from that. But if you don’t want to read everything by all of these marketers, then there are. Vehicles like your morning coffee, where you get it for free every Friday, you just glance at it and get a sense of what’s going on. And then if there’s, there’s something that really interests you, you click on it and you can read deeper.[00:42:28] Nathan:Yeah. Yep. I like that. Um what are some of the things that you’re looking to do next for your morning coffee of how to, how to grow it further? What’s sort of the milestone.[00:42:37] Jay:Yeah, we’re I really want to grow it. and we’re looking at, you know, networks that we could be a part of. we’ve got advertisers now, which is nice. you know, we’re not going to get rich from it, but it’s nice that we have, and we can pick and choose, you know, who those advertisers are. We’re not going to advertise for baked beans.We have some really great digital music sponsors my goal. Two things. One, I really want to grow the audience. I’m thrilled with the growth that we’ve had. and the quality cause I use MailChimp. So I can go in there just like constant contact or any of these other great platforms. And I can see who’s who’s subscribing which ones they opening, you know, what are they clicking through?What device are they on? And I love it when people who I admire and respect are. And I want to grow that as well. So grow it, grow the quality of it and, you know, just continue to build that audience.[00:43:39] Nathan:Are there specific activities that you’re thinking of to grow it where you’re like, oh, this was working. So I’m going to do more of that, whether it’s ads or promotions or, any of those things[00:43:49] Jay:Yeah, I, it sounds pedantic, but we always say you do more of what’s working and less of what doesn’t And I know that sounds silly, but we do that with every platform. You look at YouTube or you look at your socials and go, wow, that post really over-performed, Well do more of things like that. And I’m looking at like with your morning coffee, there are certain articles that I just know are going to get high clicks.People love lists. You know, here are the seven things that Nathan thinks you should do. People love bullet point lists, but I try not to, do the cheap applause thing, I could do the whole thing full of that, but there also has to be something in there for you to eat your vegetables.There has to be a little bit of analysis. You know, the one that comes out tomorrow, there’s a breakdown of, you know, the first half of the year versus the first half of last year. Not everybody wants to dig into the data like that. So I try to make. it You know, balanced that way. the other thing I’d like to do is partner with.Other people, for example, one of the reasons I have such a high, you know, viewership is the folks over at Hypebot every week they put my newsletter and Podcast in their newsletter that goes out to a lot of people. so they’re, a great partner for us. We love, we love HighSpot, but if I can get more people, you know, you’re standing on the shoulders of giants, so to speak, I would love to have, the.Orchard Ingrooves ADA, you know, Warner music group, Group use your morning coffee and send that out to their artists, labels, and managers, that sort of thing. That would be the next step.[00:45:33] Nathan:Yeah, that. makes sense. like those partnerships end up being so big. And I’ve seen that with a lot of newsletters where they’re doing cross-promotions or they’re saying,[00:45:42] Jay:Yeah.[00:45:43] Nathan:Hey do a takeover Where, like,[00:45:47] Jay:Right.[00:45:48] Nathan:You know, Jay’s writing the entire newsletter for us this week. If you want to follow more of what he does, you know, and you need to this newsletter swap or a bunch of things.[00:45:57] Jay:Yeah, those takeovers are really important. I did one last week with symphonic distribution, I did a little Instagram takeover and immediately had, hundreds of new subscribers to the newsletter. we always tell people there’s two reasons why nobody is buying or streaming your new release.One is they’ve never heard. of you Two they’ve heard of you, but they didn’t know it was out. Those are two things that you can correct with proper marketing, touring advertising, those types of things. And it’s the same with the newsletter is I need to get it in front of people because, every week I get a note from somebody like, oh, I just discovered your podcast, or I just discovered your, newsletter.You know, and I don’t have big budgets to advertise, you know, put it in billboard magazine or, whatever. but that’s my goal.[00:46:54] Nathan:Yeah I like it. some of my favorite podcasts interviews are Witten. The host starts asking really selfish questions like[00:47:02] Jay:Okay[00:47:03] Nathan:Direct advice that they want. So I’m going to do that now. So uh ConvertKit right So we’re creating a marketing platform, email marketing platform for creators where Uh like quick context We’re 70 people on the team[00:47:19] Jay:Wow[00:47:19] Nathan:Year in revenue, in like mostly in the blogger podcast or newsletter space, but then the last year has been this push into, into music. So we’ve got a whole range of artists from Leon bridges to Tim McGraw. we bought, a platform called fan bridge, at the beginning of this year, but we’re like new to the spaceAnd so coming in. What advice would you give either to, you know, ConvertKit or to any of these, you know, I’m sure there’s plenty of other players who are, trying to come into the music industry, really serve artists, be good citizens of the community. Like what advice would you give as far as how to grow, How to get more artists on the platform and[00:48:02] Jay:That’s a great question. I think the first thing you do is you collaborate and we tell people all the time, if, when we’re taking an artist in to meet with a digital service provider or a platform you listen first and you say, How can we partner? How can we collaborate? Not what can you do for me? So some of the obvious things, right, would be, the music business association, right?Portion, her team over there are phenomenal. You have conversations with them, you sponsor their events, you get involved in their live streams and that community. Right. I think that’s, that’s kind of where you start, as you become. A partner, you know, you collaborate, people who, all these people that you mentioned that have these great, you know, newsletters, whether it’s, you know, Sherry who, or Amber Horsburgh or, you know, Bobby, Osinski, all of these things.You, you reach out to them as you’re doing you partner with them, you see, like, how can we collaborate together? How can we work together? How can I help you to grow your audience? And once you become. Part of that network, part of that community. Let me back up. my old boss used to tell me, everybody wants to give you advice.Nobody wants to give you a job. So when you go to somebody, don’t ask them for something, right? And this isn’t directed at you. This is at the larger audience. Don’t go in and say, Hey, I need this. Can you do this? For me? People are busy, right? They’ve got a thousand emails that they’re, they need to respond to.But if you ask somebody for their advice, they’re like, well, hold on a second. What was that? You need my advice. I’ll give you my advice. I found, and I speak at colleges all the time and I mentor and I have interns. And one of the things I tell college students all the time is find someone who’s doing what you want to do.Whether it’s be an engineer, producer, tour, agent, whatever, find the people that are doing it, reach out to them and say, Hey Nathan, I’m a college student. Can I just get 15 minutes of your time? Chat. I need your guidance. I need your advice on something nine times out of 10, they’ll say. Sure, absolutely. And that’s at your fingertips right now.And as a company and as a platform, you need to let this community know what problems of theirs are you going to. You know, not your capabilities, not like the business speak while we’re a full service platform that, you know, these KPIs and blah, blah, blah. No, it’s gotta be, we’re going to help you grow your audience by doing this, we’re gonna help you, spend less money on your marketing and advertising by doing this, we’re going to help you put more butts in the seats by doing this.If you can solve their problems and communicate that. quickly and easily, that’s a challenge. but joining all of these, like, like music business association, You know, and going to these panels, like at music tectonics and some of those, that’s where those people live and breathe. And, and let me just tie it up in a bow by saying that one of the things we did over the pandemic was we formed this artist management collective and there’s, I don’t know, give or take 25 managers and on any given zoom call, we’ll have probably half of that.We, we talk about what, what publicist are you using now? What video editor are using now, you know, do you use it? Who, who should I call for a tour agent for Americana, you know, and we, we help each other, but we also will bring somebody on from TikTok or bring somebody on from roadblocks and tell us about your platform.You know, w how can you help these artists managers? So that’s a long-winded way of saying there’s no silver bullet, but. Those relationships, those, those conversations, then that word of mouth will spread and that’ll help you build your platform.[00:52:06] Nathan:Yeah Well, I mean, it’s exactly what we’ve been talking about of relationships in the community That’s what all of this comes down to and and you know podcasts are especially big for that right Because we have to have conversations like this, and that’s what you’ve seen on, on your Podcast.[00:52:24] Jay:Yeah[00:52:24] Nathan:Makes me wonder, do you think If you’re talking to a newsletter creator?Who doesn’t have a Podcast. What’s the, message that you would say to them of, you know, you’re like, Yeah. the Podcast has been good because of these things. Or are you like, what are you doing? Like start[00:52:43] Jay:Yeah[00:52:44] Nathan:Newsletter, go hand in hand. He got us started both. What, what do you think?[00:52:47] Jay:It depends. I think here’s the thing. I was reading this article the other day, that the average Podcast, this is average, right? There’s 850,000 podcasts out there, but the average one is seven episodes long. That’s it. And reaches about 175. people That’s an average thing. I mean, yeah. You’ve got the New York times daily that has a staff of 75 people and it’s crazy.And then you’ve got the Joe Rogans of the world that have these huge audiences, but that’s the outlier. That’s an anomaly. So I tell people are you really in this? Do you really want to do this? And do you enjoy doing it? So I do, two to three podcasts. every week And I love it. I absolutely love the conversations.It’s something. I have a passion for most of the newsletters that I read. There is a Podcast, you know, Sherry who has a podcast, Amber Horsburgh has a podcast. Mike Warner, has a great podcast. Then you look at how often do you want to do it? You know, like your morning coffee is every single week music biz, weekly that I co-host is every single week.You may not have the time to do that. So maybe you do one every two weeks or one every month. I’m a big fan of podcasts. I think that people go for walks, they exercise, they travel, they commute. They do a lot of things where they couldn’t necessarily read a newsletter. And this is kind of, you’re reading the newsletter to them.So it’s so easy to get syndicated. But the only thing I would suggest for somebody who’s going to start that is stand on the shoulders of giants with us. We partnered with Hypebot So immediately out of the gate, we’ve got an audience. We didn’t have to start from zero So if you can partner with a brand or partner with another outlet to grow your audience, that’s the way to go.[00:54:44] Nathan:Yeah. Yep. I like that. Some of that you said to kind of touched on the idea of longevity, you know, of the average Podcast being seven episodes long. sad, but not surprising, like[00:54:56] Jay:Yeah,[00:54:57] Nathan:What’s your message to, creators about longevity. And it’s both the artists you’re working with, you’re giving advice to those college students who hit you up for the 15 minutes of advice all the way through to those building an audience online, in a newsletter type environment[00:55:14] Jay:Yeah. That’s a great question. I think the bottom line is you need to find what lights you. up And I tell, not just college students, but I tell professionals this all the time. What is that thing that you wake up in the morning and you just can’t wait to do, and you’d do it for free. If you could, is it photography?Is it, it engineering or being a, you know, a manager, whatever it is. There’s some There’re things that are Personal to you that you love to do. And I always tell people, you have to do more of that. The money will come, but you have to add value first and then the money comes. You don’t go looking for the money.That’s a common mistake. A lot of people make, I I started your morning coffee without any expectation of any business, money, ads, anything, and it’s just been a joy. And I look forward to doing. it Every single week, I’ve got it, like 90% ready to go. Cause it goes out at 4:00 AM on Friday. So tomorrow, I’ll be up with my coffee and I’ll hit that.Send button to those lists. that’s not work to me. That’s I can’t wait to do that. And then Sunday morning, Mike Etchart and I are going to record the podcast. I can’t wait to do that. So if you can find something in your jobI love coaching. I love teaching. I love working with developing artists and showing them what’s worked in the past what hasn’t workedand to your point earlier, trying a lot of different things See, see what’s working. and What’s not, you know, I think that’s key because so many people are chasing the dollars and they’re miserable. You know, find what lights you up.[00:56:53] Nathan:Yeah, cause chasing the dollars, especially cause they tend to take a long time to come. Any creative business is slow going. So, if you’re looking at the dollars as the metric that’s going to keep you going, then you are going to end up giving up after the seven episodes.[00:57:12] Jay:Yeah.[00:57:13] Nathan:Something in that[00:57:15] Jay:Yeah.[00:57:16] Nathan:I realized, we should start to wrap up, but I didn’t even ask you about photography. That’s a huge part of who you are as a creator. We don’t have time to get into it a lot, but I just love to hear how photography intersects with the rest of your creative work.[00:57:31] Jay:I’ve been shooting since I was a teenager. What happened was I went to a concert. I shot it and the images didn’t turn out well at all. And that put me on this quest of “Why don’t my photos look like the ones in the magazine?”[00:57:45] Nathan:Yeah.[00:57:46] Jay:I got my own darkroom, started reading books. Long story short, I’ve been doing photography my entire life. I have a photo studio here. I’ve shot album covers from the Temptations, and John Wayne, and Rick Springfield, and many, many others. I absolutely love it. It’s my creative outlet. I can go in on the weekends, shut the door, turn off the phone.My partner, Chris Schmidt and I, we do these shoots and we absolutely love it. It’s also intersected with the business. So, photo shoots for clients. We’ve done videos for clients. It’s a labor of love. It’s like you find what lights you up. Photography lights me up. I would do it for free if I could.I absolutely love shooting live shows. I love shooting studio shoots. If you check out JayGilbert.net, you can see some of my work over the years. You’ll see photos from shooting Van Halen in 1978, all the way to shooting stuff last week with the immediate family.So, thank you for bringing that up. I certainly have a passion for it, and I hope that your viewers and listeners know what their passion is. Even if they can’t do it for a living, continue to do it. Life is short.[00:58:59] Nathan:Yeah, I love it. Well, I had a great time going through your whole collection over the years.[00:59:06] Jay:Thank you.[00:59:07] Nathan:There’s some that are really, really fun.[00:59:10] Jay:Thank you.[00:59:11] Nathan:Listeners should definitely check that out. Where else should people go to subscribe to the newsletter? Listen to the podcast? All of that?[00:59:17] Jay:It’s the easiest URL on the planet. It’s YourMorning.coffee. You can sign up for the newsletter. It’s free. You can sign up for the podcast. It’s free. If you ever want to dig deeper into what Label Logic’s all about, it’s Label-Logic.net. It might be kind of fun just to look through there.Jeff and I have been doing this for decades, so you’ll see some of your favorite artists that we’ve done some campaigns with.[00:59:48] Nathan:Yeah that’s good.Well Jay, thanks so much.[00:59:51] Jay:Yeah, it’s my pleasure, Nathan. Thanks for having me.

Sean McCabe is the founder and CEO of seanwes media, and Daily Content Machine. Sean is a prolific and successful creator, author, and influencer. His course, Learn Lettering, made $80,000 in the first 24 hours. For nearly a decade his podcast, blog, and courses have helped creators grow their brands, content, and skill sets.Sean’s website is a treasure trove of courses and resources for anyone looking for business knowledge and creative support. Sean’s book, Overlap, shows creators how to turn their passion into a successful business while working a full-time job. His podcast includes almost 500 episodes on content creation and entrepreneurship. His latest venture, Daily Content Machine, turns creators’ best content into clippable moments they can share across their social media accounts.I talk with Sean about what it’s like being a successful creator. We talk about growing your audience and connecting with them. We cover how to learn new skills fast, and about developing a growth mindset. We also talk about managing stress as a founder, how to handle burnout, and much more.In this episode, you’ll learn: Why good writing is the foundation of great content How to connect better with your audience Leveraging short-form content to grow your brand Pricing at full value without feeling guilty How to avoid burnout, and what to do if you’re already there Links & Resources Sean McCabe on The Nathan Barry Show episode 003 Craft + Commerce conference ConvertKit Enough Ryan Holiday James Clear Marie Forleo Ramit Sethi Sean McCabe’s Links Follow Sean on Twitter Check out Sean on Instagram Sean’s website Daily Content Machine Episode Transcript[00:00:00] Sean:If you are a founder, you should be in therapy. Full-stop. You need a therapist. I thought I didn’t. I had a great upbringing. I’m all good. Everything’s healthy. I don’t have any problems. The problem was I didn’t know the problems that I had. I didn’t realize what I was stuffing down. I didn’t realize what I was avoiding.There is so much to unpack that you don’t know you need to unpack.[00:00:30] Nathan:In this episode I talk to my friend, Sean McCabe. We’ve known each other for seven years now. It’s been a long time. We’ve been in a mastermind group together. He’s actually been on the show before. Sean is a wildly talented designer. He got his start hand-lettering.I think last time he was on the show, years ago, we were talking about that aspect of his business and how he built this substantial course business. Selling courses on hand-lettering, on marketing, on writing. He’s spoken at our conference Craft + Commerce, all kinds of things. Sean is one of the most prolific creators that I’ve ever known.It’s also super fun that he’s a friend and lives right here in town. We just have a great conversation. We talk about how you create content, which is one of those things that it’s not even how you create content, it’s why. Where that comes from. The internal drive in what you use. Where you choose to have as a source of fuel and energy to put into that creative output.How some sources are really good and productive, and others can be kind of like a house of cards, and it can be harmful. We also talk about scaling teams as a creator. How do you know when to build out a team around your business? He’s done that two different ways. So I get to ask him about some of the things he’s learned and applied differently.I’m going to stop there. There’s a lot of good stuff. So with that, let’s dive in.Sean. Welcome to the show.[00:01:59] Sean:Hey, Nathan, just saw you recently. We were playing volleyball, or something.[00:02:03] Nathan:Or something, like two days ago. You moved to my city. It’s kind of…[00:02:08] Sean:Yeah. It’s horrible. It’s a terrible place. Boise. Don’t move to Idaho.[00:02:15] Nathan:You mean Iowa? Boise, Iowa.[00:02:17] Sean:Iowa. Yeah. Don’t, yeah. Did I do okay?[00:02:21] Nathan:Yeah. That’s exactly what you’re supposed to say. If you Google something about Boise, Google has the accordion of extra questions, or things you might want to know. One of them is, “Does Boise smell?” and it’s just like auto complaints in there.And I was like, what is up with that? I clicked on it, and it’s this satirical article that has 12 reasons you shouldn’t move to Boise. One of them is the city dump is right in the middle of the city. Another one is like that the Ebola outbreak hasn’t been fully contained yet.So it’s not really safe. I think there was something about lava. Anyway, it’s just an article about all the reasons to not move to Boise. So I think you’re right in line.[00:03:08] Sean:Stay, away. That’s what they tell me to say.[00:03:11] Nathan:Yes, but if someone were to ignore that and move to Boise, they could come to our weekly volleyball game on Wednesday nights.[00:03:19] Sean:It’s casual. It’s open.[00:03:21] Nathan:Let’s try it. Yeah. It’s been so fun having you and Laci here. It’s also been fun because you started a new company. Your company is producing and editing and creating all the clips for this podcast. So, connections on so many levels.[00:03:37] Sean:Yeah. We produce this show, like the video show, the audio show, and then find clips and make those clips for social media. It’s been great. We love this show. Our team’s favorite content. So, I’m a little biased, but it’s fun to be on. Because my team’s going to work on this.[00:03:58] Nathan:Yeah, exactly. I made sure to spell your name correctly in the setup, and I know they’ll get it all.I wanted to ask what sparked—like maybe first give a summary of Daily Content Machine, since that’s what you’re spending nearly all of your time on. More than a normal amount of time on. So, what sparked it, and what is it?[00:04:19] Sean:Fun fact. This is not the first time I’ve been on the show. The last time was episode three, 2,624 days ago.[00:04:30] Nathan:Give or take[00:04:32] Sean:I was doing different stuff then. It’s been a crazy journey. Right now the newest iteration is an agency.We produce video clips. We turn long form video shows. If you have a video podcast or other kind of long form video content, we found that the hardest part is finding all the good moments in there, and turning those into short clips. That’s what we do. I designed it for myself, really.I wanted it to be where you just show up, you record, and, everything just happens? What is your experience, Nathan, with having a video and audio podcasts made, and clips and all that published? What do you, what’s your involvement.[00:05:14] Nathan:Yeah. So I think about who I want on the show, I email them and say, will you come on the show? And then I talked to them for an hour, and then I read no, either way. I don’t even do that. Yep. That’s my full involvement. And what happens is then really what I see is when the show comes out, which I don’t touch anything from that moment on. I actually probably notice the show coming out like, oh yeah, that’s the episode that we post this week. Cause we have a three week delay on our, production schedule. And so I noticed like, oh yeah, I had a David Perell on the show when I get the Twitter notification of like, David, Perell just retweeted you.And I’m like, oh, what did oh, right. Yeah. Because his episode came out and then every, I mean, David was especially generous. Right. But every clip that week seven in a row, he retweeted and posted to his, you know, hundreds of thousands of Twitter followers. Right. Cause it makes him look really good. It’s clips of him delivering these, you know, soundbites of genius, perfectly format.And he’s like great retweet share with my audience. I think that one, I picked up like hundreds of new Twitter followers, just, you know, maybe more just from, from, that. So it’s a, it’s a great experience. The side that I haven’t done as much with that I really want to. and you and I talked about this a lot when we. Like early days of Daily Content Machine and what could it be? And, and then, getting my show set up on it is the transcripts in the show notes that you all do. cause first you found the most interesting points of the show and then second there’s text versions of all of that. And then they’re all like neatly edited and, and everything.And so,[00:07:01] Sean:A lot of re-purposing options.[00:07:04] Nathan:Yeah, so like if you ask the same question or a similar question, like, Hey, how’d you grow from a thousand subscribers to 10,000. Tell me about that process. If you ask that consistently, which I’m not great about asking the same questions consistently, but then over the course of 20, 30 episodes, you have this great library of answers to that question and you could make like compile it all, write some narrative and it’s like, oh, there’s an ebook that would be 15 pages long and could be a free lead magnet or a giveaway or anything else. It’s just a total by-product of the podcast and Daily Content Machine. So I’m a huge fan. That’s my experience.[00:07:42] Sean:Well, it’s great to hear. yeah, we wanted to make it, I wanted to make it, so I just show up. I record myself doing a podcast with the camera on, and then I walk away. Like I don’t have to, the footage sinks. It goes to the team. They produce it. They made me look good. They make me sound good. They find all of the best things. I said, things my guests said, they think about my target audience. What are their struggles? What are their goals? What do they want, what do they need? How would they search for it? How would they say it themselves? And they work together to come up with good titles for them, then produce it, flawless captions, you know, do the research, how’s the guests build their name.How does their company name capitalize? Like make sure it’s, it’s all polished and then publish it everywhere. So I just show up once a week for an hour and record, and then I get to be everywhere every day. That’s that’s at least the goal. And I’m hearing you say like one of the benefits, but one of the benefits of finding clips out of your long form shows to post on social media is you give your guests something to share.And there’s kind of two, two ways of approaching podcasts. And one is kind of the old school way, you know, People used to blog and the used to subscribe to RSS feeds and like, you know, that’s how they consumed their content. And definitely you still want to build your own platform, have a website, have a blog, you know, definitely have an email newsletter on ConvertKit but now we’re, we’re posting Twitter threads. We’re posting more content natively and people are consuming more natively on the platforms. So there’s the old idea of, I have a podcast, here’s a link, go listen to my podcast, go watch my podcast, go watch my video shifting from that to, Hey, why don’t we deliver the best moments of the show?Because people are consuming short form content, and that’s how they’re evaluating whether they want to subscribe, whether they want to spend an hour listening in depth to that interview. We’re giving them all of these entrance points and just providing value natively on the platform. Instead of asking them to go off the platform and interrupt their experience, it’s here you go.Here’s some value here’s where you can get more.And, and that that’s such a great way to. Bring new listeners on as well as to give the guests something to share, because think about the experience between a guest, being told like, Hey, your episodes out, will you, will you share a link to it? And they’re like, Hey, I was on a show, go listen to the show.It’s such a great interview. You know, we, we do it. We want to help out that, that person with the podcast. But imagine if the best moments that, where you said that the smartest things with all of your filler words remove and your tangents remove was tweeted, and there’s a video right there. All you have to do is hit retweet.It’s free content for you. It looks good. But then also for you as the show host, it promotes your show and gives you a new awesome.[00:10:28] Nathan:The other thing in it, like the retweet is fantastic, but a lot of people want that as original content on their social channel. And so having like the, the deliverable that I get from you all is, is. Yeah, it just shows up in Dropbox of here’s all the videos for all the platforms and everything, you know, from my archives and all that.And I’ve sent those on to the guests when they’re like, Hey, can I post this? Not every tweet. Like I want to post it with my own, title or tweaks on that. And so I can just share that whole Dropbox folder and they’ll, they’ll go find the exact thing they want to share and, and use it in their own softens.Like, yes, absolutely. Because the pre-roll or like the, or the post roll on that video is like, go subscribe to item newsletters. It’s like, yes, please.[00:11:14] Sean:And it’s not like Nathan, that you would have trouble getting guests, but if one had trouble getting guests for their show, or you want to get someone that’s like really big, really busy, they get all kinds of requests all the time. Well, imagine if they’re evaluating between these different shows, you know what, what’s the audience size?What am I going to get out of it? You know, especially if you don’t have millions of downloads on your podcast. Well, if you’re providing these additional assets, like, Hey, we’re going to make clips of this. You’re going to get content out of this. It can help people make that decision to come onto your show as opposed to maybe another.[00:11:46] Nathan:Yeah, totally. I want to go, so somebody different directions. This is, we talked about an agency and the business that you’re starting. I have a question that I’ve kind of asked you one-on-one sometimes. And I want to know why build a business with a team and like build this X scale of business rather than go the indie creative route.Right? Because if we want to, if you wanted to say independent, no team, you could probably make a business doing $250,000 a year. Work on it, maybe 20 hours a week, something like that, you know, hanging out in the studio, you’d still have your podcast. You could sit down and like, you’re one of the most prolific writers I’ve ever met. so you could do a bunch of those, those things. And yet you keep trying to do and succeeding in doing these much harder businesses of building a team. And I have to know why.[00:12:39] Sean:Nathan, I don’t know. I don’t know why. I kind of know why, uh it’s it’s like it’s going to get deep. I mean, it, it probably really goes back to childhood and being, being the oldest of 13 kids feeling like. I don’t know if my parents are watching, but like, I felt this, this pressure to be successful, to be a good example, to be, to be a leader, you know, like to be productive.And, you know, I’m working through a lot of that stuff in therapy, like learning, like where did my motivations come from? And like, you know, it is this healthy because, you know, you know, my, my background of extreme workaholism for like 10 years, like, Nope, no joke. It was really bad. Like 16 hour days, seven days a week for 10 years, like all I did was work and like that’s, that’s my tendency.And I think something beautiful came out of that, which is this sabbaticals idea where since 2014 now I’ve taken off every seventh week as a sabbatical. So I work six weeks and I, I take off a week and we do that with our team and all of our team members. I paid them to take off sabbaticals and it’s just been beautiful.The heartbeat of the company. And like, it’s been really good for me as well in terms of, you know, burnout prevention and just unlocking my best ideas, but that’s, that’s my tendency. And, you know, th there’s, there’s all kinds of reasons. And, you know, there there’s messages that we hear that maybe were said or implicit, you know, growing up that we internalize.And so I think, honestly, Nathan it’s, it’s probably just like chasing, like, I’m going to be dead honest, like, like it’s, it’s just like, I think of your post that post that you titled about enough, you know, and, you know, thinking through it, like, like if I were to just think of a number, you know, it’s like, no, that’s not enough, you know, and I know that’s not healthy.So like, yeah, I could totally, I could totally do the solo thing. I could totally make 600. Work part-time, have less stress and maybe I should, you know, maybe I will eventually, but there’s something in me that wants to build something bigger, but at the same time, it’s just so much fun. Get it, like, I just love processes and systems and like, you know, building things that can scale.And so, yeah, it’s.[00:15:08] Nathan:Well, let’s lean into it more because I have the same thing on two different sides. Like I made the same leap from a solar creator to having a team. and there’s sometimes I miss aspects of the solo creator thing. Like there’s a level of simplicity and like, I look at somebody’s product launch or something, and it does $25,000 or $50,000.And I’m like, oh, I remember when that amount of money was substantial in that it moved the needle for the business and like, and drove real profits. Now, like 25 or $50,000 gets eaten up by that much of expenses, like immediately, you know, cause the, the machine is just so much, so much bigger. And so I have the same thing of, of pushing for more and trying to figure out what. Like, what is that balance? And, and, yeah, I guess, how do you think about the balance between gratitude and enough and drive and ambition?[00:16:08] Sean:Yeah, that is a great question. It is. It is a balance. And as someone who has a tendency towards all or nothing thinking like, I’m, I just get obsessed. Like if I’m, if I’m about something like, I’m just all in, or I don’t care at all. Like I’m really not in between. And that I think is a double-edged sword.Like it’s a reason for my success, but it’s also a reason for all of my downfalls and like, you know, going years without exercising and losing relationships and friendships, because I was so consumed by what I was building, you know, it is very much a double-edged sword. And so I think the answer is balance, you know, in what you’re saying, w what do you, what do I think about the balance?I think it is a balance. It has to be, you have to be operating from a place of enough and then have things that are pulling you forward. You know, something that you’re working towards having goals I think is healthy. You know, it’s. Something that gets you out of bed in the morning. You’re excited about what you’re doing.You have this vision for where you’re going, but it’s operating from a healthy place of, I’m not doing this to fill a void in my soul. Right? Like I’m not doing this because I believe I’m not enough because I believe I’m not worthy of something. But, but because I know, yes, I matter I’m worthy. I’m important.And I’m excited. Like, I think that’s the, I’m not saying I’m even there. I just think that’s the balance to strike[00:17:34] Nathan:Yeah. I think you’re right in this. It’s interesting of the things that you can do in your, I guess, life, maybe the creative Dr.. I think there’s a tendency of using that insecurity to drive creative success that can work really, really well for an amount of time. Like if you need to finish a book, grow your audience to a thousand subscribers, you know, like accomplish some specific goal.And he used the chip on your shoulder and the feeling of like, this person doesn’t believe in me and that like triggers those deep insecurities on one hand, it’s wildly effective and on the other, it can be super destructive and it’s such a weird balance and place to sit in.[00:18:21] Sean:Yeah, a double-edged sword, for sure. Like it can, it can be what helps you succeed? And it can be your downfall. So you have to wield it wisely. unintentional illiteration you ha you have to be careful with that because it’s so easy to just get consumed by it, to drown in it, to let this, you know, whatever it is, this, this, this drive, this motivation, the chip on the shoulder, whatever it is to let it take you to a place where you’re just like, along for the ride, you know, on a wave, going somewhere on a, on a, you know, a tube floating down the river, right.You’re just being taken somewhere, but are you being taken where you wanna go?[00:19:05] Nathan:Well, yeah. And then realizing, like, it might feel like you are up into a point, but then I guess if you’re not aware of it and you’re not in control of it, then you’ll get to the point where the thing that you were trying to succeed, that the book launch, you know, hitting $10,000 in sales or whatever else, like that’s not going to have any of the satisfaction and.[00:19:25] Sean:If I can take an opportunity here just to speak very directly to a point. If you are a founder, you should be in therapy. Full-stop like you, you need a therapist. I thought I didn’t. I was like, I had a great upbringing. I’m all good. You know, everything’s healthy. I don’t have any problems. The problem was, I didn’t know the problems that I had.I didn’t realize what I was stuffing down. I didn’t realize what I was avoiding. There’s so much stress, you know, being a founder or even any, any C level executive in a company, like there’s just so much going on, and you’re responsible for so many things it affects your personal life. It affects your relationships.It affects how you see yourself. There is so much to unpack that you don’t know, you need to unpack. And there’s probably also stuff that, you know, you need to unpack. and Maybe you don’t want to, but I went my entire life until the past year. Never going into therapy, never went to therapy. I’m like, yeah, that’s great.You know, if you have some serious problems or a really bad childhood or whatever, like yeah. That’s, you know, I support, it like positive, you know, like golf clap and I’m like, oh my gosh since I’ve been going on. I’m like I didn’t know why I was doing the things I was doing, what my reasons were, what my motivations were, the ways that it was unhealthy to me, the way that it was affecting my relationships.So I just want to encourage everyone to go to therapy. I promise it’s going to be beneficial[00:20:53] Nathan:Yeah.I cannot echo that enough. I’ve had the same experience and just having someone to talk through whatever’s going on in your life, whatever, like even just interesting observations. When someone said this, I reacted like that. And that doesn’t quite add up. Like, can we spend some time digging into that kind of, you know, and you realize that like, oh, that wasn’t, that wasn’t a normal, like healthy reaction.And it had nothing to do with what the person said or who they are or anything like that. I had to do it. This other thing, the other thing that I think is interesting about therapy is when you’re following people online, you’re partially following them for the advice and what they can do for you and all of that.But I think the most interesting creators to follow are the ones who are on a journey and they bring their audience, their fans, along that journey with them. And a lot of people are on a really shallow journey or at least what they put out online is a really shallow journey of like a, I’m trying to grow a business from X to Y I’m trying to accomplish this thing.And it’s like, Like, I’m happy for you. There’s like tips and tactics that you use along the way. And that’s moderately interesting, but I think if you’re willing to dive in on therapy and why you do, or you make the decisions that you do and what really drives things, it makes for as much deeper journey, that’s a lot more interesting to follow. And all of a sudden the person that you followed for like learning how to do Facebook ads is talking about not only that, but the sense of gratitude that they were able to find in the accomplishments that they made or how they help people in this way or other things that’s like a really authentic connection.And I think that, even though like growing a more successful business is not the goal of therapy and, and all of that. Like, it has that as a by-product.[00:22:42] Sean:It does. It definitely does. Although I’m, I definitely look at things the way that you’re saying, which is like, what is. Productive output of doing this thing. And it’s like, yeah, that’s why I need to be in therapy to understand why I apply that lens to absolutely everything. but I I’ve found it immensely helpful.I would say I would echo what you’re saying. in terms of sharing your journey, both the ups and the downs. I think that the highs of your journey are only as high as the lowest that you share, because otherwise it’s just kind of it’s, it’s flat, you know, there’s nothing to compare to like th th in the hero’s-journey-sense you know, we we’re rooting for the underdog who is going through challenges, and then we’re celebrating with them when they have the wins.If you know, if you’re not sharing the, the, the low points, it’s not as relatable. Now that doesn’t mean you have to share everything you’re going through. You don’t, you know, you can keep some things, you can keep everything personal. I’m just saying, if you have the courage to share what you’re going to find is that you’re not alone.You’re not the only person going through these things. You’re not the only person feeling these things. And sometimes the biggest failures or, or the things that, that hurt the most or the most difficult to go through when you share those, those can actually resonate the most. That can be where your, your community really steps up.And you, you feel that, more than any other time.[00:24:07] Nathan:Yeah. I think that, like I wrote this article a few years ago, titled endure long enough to get noticed, and it was just actually wrote it, it was off the cuff. I was on a plane just like needed to get something out that week. And it was an idea about serum on my head and I wrote, wrote it out, send it off.And, just the replies from it, because it took a more personal angle and it was talking about some of the struggles and a bunch of the replies were like, oh, that’s exactly what I needed in this moment. Like, I was about ready to give up on this thing, you know? And, and that was that bit of encouragement. It ends up being this thing that feeds both ways. If you’re able to take care of your audience and then if you let them, your audience can take care of you of saying like, oh, that that was really, really, meaningful.[00:24:49] Sean:Can I turn it around on you for just a second and, and ask, I, I know Nathan, you’ve been writing recently, you’re on a bit of a streak and for those. Following your journey for a long time. They know you’ve, you’ve gone on streaks for periods of time. You made an app to log those things. We’re talking about this recently.And I was just curious, what, what made you start writing again? And it may be, if you can touch on like the identity piece that you were sharing with me.[00:25:17] Nathan:Yeah.So most good things that have come in my business. Many of them, at least for a whole period of time, he came from writing. I wrote a thousand words a day for over 600 days in a row. And like, that was. Multiple books, a 20,000 subscriber audience, like just a whole bunch of things so I can work it from and everything else. And I’ve, I’ve tried to restart that habit a handful of times since then. And yeah, you were asking the other day, I’m trying to think, where are we out of the brewery? Maybe? I don’t know.[00:25:51] Sean:Yeah. Something like.[00:25:51] Nathan:Well, I’ve all something. And you’re just asking like, Hey, you’re restarting that what what’s driving that. And the thing that came to, I actually came to it in a coaching therapy conversation was like, I’m a writer. That’s who I am. You know, it’s part of my identity and yes, I’m also a, a creator and a startup founder and CEO and whatever else, but like, realizing that. I’m most at home when I’m writing, that’s not what I’m doing. Writing is my full-time thing. And like, here’s the cadence that I put out books, you know, obvious thing of like Ryan holiday, he’s super prolific, like a book or two a year, you know?I’m not a writer in that way, but I, I have things to say and, words have an impact on people in the act of writing has such an impact on me that I realized that I feel somewhat of this void if I don’t exercise that muscle and stay consistent of not just like teaching and sharing, but also taking these unformed thoughts that bounce around in my head and it, and like being forced to put them out in an essay that is actually coherent and backs up its points and like, Yeah, it makes it clear.So anyway, that’s the, that’s why I’m writing again. And so far it’s been quite enjoyable. I’m only on, I think, 20 days in a row of writing, writing every day, but it’s coming along now. I have to look. 21 today will be 22.[00:27:19] Sean:Nice. Yeah. Right. Writing is so great for clarifying thinking. And I love the, the identity piece. It’s like, I’m a writer, you know, that’s what I do. And I think it’s interesting to think about whether it’s kind of chicken and the egg, right. Maybe, maybe James clear would, would disagree, but like, does it start with a belief that you’re a writer and therefore you write, or is it the act of writing that makes you a writer?And if you, if you aren’t writing, then you’re not.[00:27:50] Nathan:Yeah. I wrote something recently and maybe it’s a quote from somebody of, if you want to be the noun and you have to do the verb, you know, and so we’re looking for, how do I become a writer? How do I become a painter? How do I become a musician An artist, any of these things? And it’s like, if you want to be a writer?Yyou have to write, you know, like, and I think we, we get so caught up in the end state that we start to lose track of the, the verb, the thing of like writers, write painters, paint, photographers, take photos, you know? And so if you’re not seeing progress in that area, then it’s like, well, are you actually doing the verb?And yeah, that plays a lot into identity and, and everything else.[00:28:37] Sean:I like what James, James clear says about like casting a vote for the person you want to[00:28:43] Nathan:Yeah, I think I referenced James on. So it’s the, I reference you probably every fourth episode. And then James, maybe at like, just on alternating ones.So the thing that I quote you on all the time is the show up every day for two years, like I always had create every day as a poster on my wall, and I really liked the for two years, angle. And so I I’d love for you to share where does the for two years part come from and why, why that long? Why not for two months or two decades or something else?[00:29:16] Sean:Right. It really, the whole show up every day for two years, idea came from me, drawing letters, hand lettering. You know, you think of the Coca-Cola logo. That’s not a font. That’s, you know, customer. That’s what I would do is draw letters. Like, like what you have behind your head, that type of style of lettering.And I just enjoyed doing that and I, it wasn’t a job or anything, and I really didn’t pursue it seriously for a long time, even though I enjoyed it as a kid, because I thought I could never make a living at this, you know? And it’s that like productivity filter again, what can I be successful at? You know, as opposed to like, Hey, what do I enjoy?You know? And, it took an artist telling me, Hey, if you enjoy it, just create. because cause you enjoy doing it. Just create. I was like, yeah, I don’t know why I needed that permission, but I did. And I just started creating and I was creating for me, like, because I loved it. And I was sharing on Instagram and Twitter and places like that, the drawings I was making, but nobody really cared or noticed for the first two years.And it, it, it, that was okay with me because I was doing it for myself. I loved the process. I love the act of. But somewhere right around two years, it was just this inflection point. It’s kinda like you say, you know, like do it until you’re noticed, right. And people started asking for custom commissions, do you have posters?Do you have t-shirts? And the reason I recommend that people show up every day for two years is it’s not going to happen overnight. You know, hopefully in that time you find the reason for yourself that you’re showing up. and the two years part is arbitrary for some people within eight months, they’re on the map and people notice their work and maybe they could quit their job or, or whatever.Right. But two years is really just to give people a mark, you know, to, to work towards. by that time they figure out like, oh, it’s not actually about two years. It’s about showing up every day.[00:31:16] Nathan:Yeah. And a lot of what I like about two years is it since your time horizon correctly. and it helps you measure your like past efforts. I think about, you know, if you’ve thought about starting a, like learning a musical instrument or starting a blog or any of those things, you’re like, eh, I tried that before, you know, and you’re like, yeah, I showed up most days kind of for two months, maybe, you know, like when you look back and you analyze it, you’re like, oh, I didn’t show up every day for two years. And there’s also sort of this implicit, I guess conversation you have with yourself of like, if I do this, will I get the results that I want? And cause the, the most frustrating thing would be to put in the effort and to not get the results and how the outcome you’re. Like, I tried it for so long and I didn’t get there. And so I believe that if you’re doing something like creating consistently showing up every day, writing every day for two years and you’re publishing it and you’re learning from what you, you know, the results you try and consistently to get better, you almost can’t lose. Like, I don’t know of examples of people.Like no one has come to me. I actually emailed this to my whole list and said, like, what is something that you’ve done every day for two years, that didn’t work. And people came back to me with story after story of things that they thought would be that. And then it like started working a year or year and a half in, or at some point in there because it’s really hard to fail when you’re willing to show up consistently for a long period of time.[00:32:54] Sean:And I think there’s a point of clarification there kind of a nuanced discussion where some people might say, well, you know, where where’s, where’s the other end of the spectrum, where you’re just continually doing a thing that doesn’t work, you know, doing the same thing and expecting different results.And I don’t think that’s what we’re talking about here. Like when we say show up every day, Showing up everyday to your craft, you know, for yourself to better yourself, whether that’s writing or drawing or working on your business. This doesn’t mean never course-correcting, this doesn’t mean adapting or adjusting to find product market fit.We’re talking about showing up for yourself. This doesn’t mean even posting every day. It’s not, it’s really not for others. Like share what you want. If you want to tweet every day, if you want to blog or post your art every day, go for it. I actually tried that and, you know, it was pretty exhausting and that’s part of why I made Daily Content Machine.I was like, how about I show up one hour a week and you turn that into Daily Content for me. but still on all the other days, I want to show up for myself. And, and often for me, it starts with writing as well. I think it all starts with writing, whether it’s a business idea or a course or a book or content like writing is just the seed of all of that.So I like writing, not because I. It was born a rider or anything. I just see results from it. So for me, it’s showing up in writing, even if I’m not posting that, or I’m not posting it now, you know, it’s just for me.[00:34:19] Nathan:Yeah. And that’s an important point because a lot of the time my writing is just chipping away at some bigger thing. Like some of the long essays that I’ve written have been written over the course of three or four months, you know, it’s not like I got it together and like published it and it was ready to go.It was like an ongoing thing.What, like, what are some of your other writing habits? Because you’re someone who has written a ton, I’ve seen you consistently write like 4,000 words a day for an entire month and stuff like that. yeah. When someone asks you, how do I become a better writer? How do I write consistently any of that? What are some of your tips?[00:34:55] Sean:Yeah. I’ll tell you how not to do it, which is how I’ve done it, which is back to our earlier discussion. Just kind of all or nothing. my first book I wrote in 14 days, 75, 80,000 words, and my, my second book, which I still haven’t edited and published. I was like, I want to show people that things take, as long as the amount of time you give them, how long does it take to write a book a year, 10 years a month?You know, two weeks, I was like, I’m going to try and write a hundred thousand words in a single day. So I live streamed it, and my idea was to speak it and have it dictated, right. Have it transcribed. I made it to 55,000 words. And these are like, it’s, it’s all you, you can find it. it’s, it’s coherent words like this.Isn’t just feel like, like the book was in my head. I made it to 55,000. My voice was going and I’m like, I think I’ve got most of the book. I’m not going to kill my voice. And that’s, as far as I made it. So I failed on the goal, but still got 55,000 words. But then for the next, like three, three or six months or something I hardly wrote.Cause I was just like, oh yeah, you know, look what I did. You know, I wrote all those words and it’s like, no, that’s not the right way to do it. Like I actually, I think there was a point to what I was doing and it was, it was a fun stunt or whatever, but I kind of regret that, you know, I wish I just stuck to, you know, you had that, that idea of like write a thousand words a day and this is something I would share with people as like an idea for starting out, Hey, try and read a thousand words a day.And I found out people would get stuck on that. They’d be like, I wrote 830, 2 words. I’m a failure. I’m just gonna give up and wait until the weekend when I have more time. And it’s like, no, that’s not the point. The point is to just show up and, and put some words there. So maybe for you, it’s a time like write for 20 minutes, write for 15 minutes, write three sentence.And maybe you keep going, you know, but like put in the reps, show up, you know, put on the running shoes and go out the front door. If you don’t run the five miles, that’s fine. You know, walk around the block, but show up. And so I I’ve done it both ways and I don’t prefer the stunt way where I write 50,000 words in a day.I prefer the, the, the ones where I write 400 words every single day, that week[00:37:06] Nathan:Yeah, I think that’s absolutely right. And I’ve, I’ve, had that a lot of times where I was like, oh, I can’t write today because I, I wouldn’t have time to hit 500 or a thousand words. And so that’s something I’m doing differently this time around of like, look even a hundred or 200 is a, is a success, any amount of, of doing the reps as good.[00:37:26] Sean:I want to lean in on that idea of defining success as less. What I mean by defining success as less is, and this is especially helpful. If you’re going through a hard time, if you’re feeling burned out, if you’re feeling depressed, w with remote work, growing and growing, you know, w we’re commuting less, we have more time.We have more flexibility in our day, but we, we tend to fill that time with just more and more work. And it’s really easy to get to the point where you feel overloaded. And you, you go into your day just too ambitious thinking. You can get too many things done and ending with disappointment. Like I didn’t get all the things done, you know, and you’re just on this perpetual cycle of disappointment every day, setting yourself up for disappointment, trying to do too much.And instead of defining success as less. And so if you’re, if you’re feeling depressed, I mean, this gets as small as today as a success. If you brush your teeth, like today’s a success. If you shower, today’s a success. If you walk around just your block, that’s it not run a mile, you know, not come up with a new business plan or outline a whole course or something.Less defined success is less, when I would do podcasts, I, you know, a podcast is what an hour, maybe two hours or something like that. But it takes a lot of energy. If you’ve never been on a podcast, you know, it takes energy to record. And I would feel bad after I record a podcast, not getting as much done afterward, you know, like, oh, I didn’t get that much done.I mean, I recorded a podcast, but then I was supposed to have this and this and this, and just beat myself up. And I realized like, Hey, that, that podcast I recorded, that’s going to be heard by thousands of people. That’s really high leverage work. And I brought my best self and I really showed up and I really delivered.And that was good work. And you know what, on days where I have a podcast, I’m going to define that day as a success. If I show up and record that podcast, anything else is a bonus. And, and you just make that smaller and smaller and smaller until it’s accessible to you until it’s attainable for you. So maybe it’s like write three sentences.If you show up at all to your writing app and write three sentences, the days of success. And what you’ll find is more often than. You’ll keep going.[00:39:34] Nathan:I think that’s so important in, and I imagine most creators have been in that position of no motivation feeling depressed. And then you beat yourself up because you didn’t get anything done, like deriving yourself worth. This kind of goes back to the earlier conversation, driving your self worth from what you create can both be very powerful in that it can feed itself really well.And then it is also incredibly fragile. And I’ve gotten to that point where if you end up in the downward spiral version of that, then like not creating, not accomplishing something. Leads you to feel more upset and depressed and so on. And it like when it works, it works well. And when it stops working, it fails spectacularly.And I think you’re right. That the only way out of it is to lower that bar of success to something crazy low that you can’t consistently. And then, you know, gradually you’re way out of it from there.[00:40:34] Sean:Yeah, you, you are more than what you do. You are more than what you create. You are more than what you produce. You are more than your job. You are not your company. You’re not the money in the bank. You’re not how much you make each month. You’re not the decline in revenue from this month compared to last month.Like you’re none of those things. You’re a person you’re a human outside of that with independent work. And that’s such a hard thing to internalize, but, but if you can, I mean, you, you, you just become impervious to all the things that can come against you. You know, you just become unstoppable. Nothing’s going to phase you.Like you can embrace the highs and embrace the lows and just ride the rollercoaster. And I’m just describing all the things that I don’t know how to do, but I’m working.[00:41:20] Nathan:Yeah. It’s all the things that we’re trying to, like lean in on and remind ourselves of, in those, in those tough times, I have a friend who has his game, that he played his, a few little kids, and his sort of a little game that he plays with them over time. And he like in a playful, joking voice, he asked them like, oh, what do you need to do to be worthy of love? And it’s like turned into the thing for they, like, they’re like nothing, you know? And he’s very purposefully trying to counteract this idea of like, oh, I need to earn worthiness. I need to earn love. If, if I like show up for my parents in this way, if I take care of my family in that way, if I’m not a burden on other people, then like, Then I’ll be okay and I’ll be worthy of love and all of that.And so he’s just playing it, like making it a playful thing with his kids from a very young age to basically instill this idea of like, you are a complete whole person and you can’t, like earn worthiness of love and you also can’t lose it.[00:42:19] Sean:I’m just thinking of the titles for this episode, that my team’s going to come up with, like how to be a founder worthy of love.[00:42:26] Nathan:Yes, exactly.[00:42:28] Sean:Don’t use that title.[00:42:31] Nathan:Okay. But I want to go, you’ve built a, a team twice, for first for Sean West, as a business, you know, of the course and content, community business. And then now for Daily Content, I want to get into, like what you like, how you built the team differently between those two times and what you learned. but before we do that, let’s talk about as a solo creator. When you’re thinking about making that leap to something where you need a team to build it to the next level, maybe you’re at a hundred thousand dollars a year in sales, and you’re looking at maybe the roommate’s eighties and the Marie Forleo’s of the world where like a few, rungs above you on the same ladder.And you’re like, okay, that would require a team. What are some of the things that you think people should consider in that leap?[00:43:22] Sean:My biggest mistake was applying the right advice at the wrong time.Like I’m not a, I’m not a reckless person. Like I’m going to do my research and learn and like get all the smart people’s advice. And so every, every big mistake I’ve made was as a result of applying great advice from smart people at the wrong time.And so it’s, and, and I don’t think I’ve ever heard anyone really, really talk about this. There’s a lot of people slinging advice who should really be asking questions, but at the same time, you can’t even blame them. Cause like Twitter, there’s no room for nuance. Like you tweet fortune cookie tweets, you know, with, with advice and like, hope that people apply it at the right time.Like, that’s just kind of how it goes. But like, you know, to, to your point of like looking to other people and what they’ve built and like, oh, that’s what I would need and stuff, you know, I, I heard things. Delegate, you know, you don’t want superhero syndrome. Like you need to empower other people and delegate the things you’re not good at delegate the things you don’t like to do, delegate the things you’re good at.And you like to do, but you shouldn’t do because you’re the founder and you need the vision, you know, like, so it’s like delegate, delegate. And so, okay. All right. Hire. This is going to sound really stupid, but no one told me that you need to make sure the thing that you’re doing is working before you hire, because hiring is scaling, which means to make something bigger.And if you’ve got a bucket at the beach and the bucket has holes in it, and you scale that bucket, you have a bigger bucket with holes. Like th th that’s not better. That’s like, do you, do you like the stressful problems you have now? How would you like problems with another zero on that? Like you have $30,000 problems.Do you want $300,000 a month problems? Like, you know, it’s not fun. so nobody’s told me that and looking back, it’s like, it’s so dumb. Like, do you think making this big. Automatically makes it better. It’s just going to automatically make the problems go away. No, you need to, you need to scale. What’s working, do more of what works and, and, and slow down and hold off and make sure the thing you have is working before you grow it.I don’t know if I answered the question, but I’m just speaking to my past self.[00:45:32] Nathan:You totally did. So what are the things that, like, how does that play out as you’re building Daily Content Machine, versus the previous team?[00:45:40] Sean:The difference here is my, my previous business required me to function and I hired people around me, you know, to support me. So I wasn’t doing all the work, but I had to show up. I had to, you know, whatever I had to write, I, you know, come up with an email or blog or. Or live stream or podcast or whatever.It was like, it was built around me and there’s nothing wrong with that. Like, that’s totally fine. You can build a business where you do what you love and you’re supported by your team. I just found that you can, you can do something that you love and burnout, like after you do that for years and years and years, it’s not even that I don’t like podcasting or I don’t like writing cause I actually do what it ultimately came down to is that I don’t like having to do it.And if I don’t, if I don’t, then everything falls apart. And so with this new business, the agency, it was like, okay, like the first thing I want to build from is this can’t require me to function. It has to be built in a way that the team can run things where it’s like, I don’t have to be on the strategy call.I don’t have to do the marketing. Like my face isn’t necessarily the reason people are coming to. and that, that really shifted how we build things.[00:47:01] Nathan:Yeah. I mean, that, that’s a huge thing. And like, I imagine you defining all of these roles and early on, you might be doing a bunch of them to test if it works and to build out the systems, but none of them are like defined by your own unique skillset. Like you actually I’ve loved watching your systems and the, as you’ve shown me behind the scenes, because you’re breaking it down and you don’t need one person who is a fantastic video editor and copywriter and project manager talking about that, actually, because I think so often we’re trying to find the employee or the team member. That’s like the, the unicorn perfect fit. And you’ve made a system that doesn’t require.[00:47:42] Sean:Exactly. And we did start out that way, where, when, when I was initially hiring for, you know, this Daily Content Machine service that we have, what’s involved in that process and we talked. Clients and prospects all the time that like the Mo one of the most common things they try to do is either build a team in-house that can find all the best moments scrubbed through the long form content, edit it.Well, you know, titles, research, all of that, the build that team in house, or hire a freelancer and the problems with either of those is like what I’ve identified as it comes down to the person doing, doing content repurposing well requires nine key skills among them like copywriting and marketing and design and animation and rendering, and like, you know, SEO and all of that stuff.And I’m not saying there’s, there’s no one out there with all those skills, but, but those people are doing their own thing most of the time,[00:48:38] Nathan:I think I’m a pretty good Jack of all trades. And I think if we get to five of those, probably maybe on a[00:48:45] Sean:You could probably do most, I can do most too, but I don’t scale, you know, so I’m trying to, I’m trying to scale me. and the first thing I tried to do was hire someone who could do all the things like, okay, you need to be able to, and that very quickly was not the way that was not going to work.So we realized we need specialists. We need people who are really good writers. We need people who are really good animators. People who are good editors, people who are a good quality assurance, reviewers, people who are good project managers, you know, all of that. And that’s, that’s what probably sets us apart.You know, the most unique thing is like, we learn about your audience and we find all of the moments and like teaching people, I’ve talked to people who have their own teams, or they’re trying to build teams for doing this. And that’s the hardest part is how do you teach someone how to find those moments?Like video editing is commoditized. You can find a video editor anywhere, but what happens when you try and get a freelancer who can just chop up clips and animate it and put a slap a title on it? Yeah. Th they’re not, they don’t care about the quality. They’re not capitalizing the book titles and the company names and spelling the guests.Right. You know, and the titles of the clips, that’s like half of it, you know, like half of it is the title, because that’s going to determine whether someone sticks around and clicks or watches or whatever, and they’re not thinking the right way, or they’re not finding the right moments. And so the person who’s outsourcing, they’re trying to go from, I’ve been doing this myself.I’ve been editing my own video. I’ve been scrubbing through my own long form content to now, okay, you have got this freelancer, but now you’re a project manager and a quality assurance reviewer because their work isn’t up to par. And so I have people asking me like, how do you teach people how to do this?Well, how to find those moments, what’s going to provide value to the audience. How do you title it all? and that part, I’m not giving away because that’s, that’s our home.[00:50:33] Nathan:Yeah. And that, that makes sense. So you described Daily Content Machine as an agency and it is, but I was like, great. You’re an agency. Here’s my other idea for a show where. Like a dream it up and produce it. Or actually we build my website for me, like your, your designers on all that.Right. And your answer would be like a flattened and I think that’s really important for the business. So can you talk about the difference between the agency that you’re running in productized services and how you think about making that scale versus like a, an agency of, Hey, this is our hourly rate.These are the projects we’re best at, but we’ll kind of take on anything.[00:51:11] Sean:So maybe I’ll I’ll I’ll title the clip of this moment, how here’s, how you will try it like this. Here’s how you create a six figure agency. And for. It is by saying no to almost everything and getting really specific about what you offer and to whom. So my previous, the previous iteration of my business, I was out of a scale of one to ten I was working at a level 11 effort, you know, to bring in six figures with this version of the business. It’s like a one or two in terms of, you know, getting people to give you vast amounts of money. And the difference is in what you’re providing and, and to whom. So you’ve kind of got this, this matrix of products or services that either make money for your clients, or they’re just nice to have.And then on the people side, you have, it’s a generalization, but people who have money and people who don’t, and I was always playing on hard mode, you know, I was trying to sell like kind of more premium stuff to people who didn’t have money. And I’m like, you know, feeling bad about not being able to give stuff to the people who don’t have money.And it’s like, you know, what a really great way to do this would be to provide premium services that make money for people who have. So I decided I’m going to start with six to seven figure business owners. What is it that they need? And what is it that, that I’m good at, you know, core competencies. And that’s where we came up with this idea.And the hardest part has been not giving into shiny object syndrome. All of the things that we could do, all of the services that I want to build. And it’s like, no, there’s so much more juice in this one thing. If we just stick to this and just become the best at finding, identifying, and producing and distributing clips from long form content and just be really, really good at that.There’s enough complexity in that, you know, and just see that as the game, like, how can we get really good at this? How can we sell this better? How can we deliver it better? How can we increase the quality and just getting really focused and aligning what you offer the value of that to the people you’re offering it to within four weeks with just a page and a form.This was a six figure book.[00:53:16] Nathan:When I think about the price of the offering. So I think I have. for what I pay for and Daily Content Machine paying about $5,000 a month. Is that right? I think somewhere in there.[00:53:28] Sean:So, what we didn’t say is you, you kind of talked me into, adding another service, which is, we also do the video and audio show notes, transcript, like podcast production piece. So like, we’ll produce the full thing. You just show up and record sync the footage to us. We’ll produce the show and we’ll make the clips.That’s actually been a really nice bundle, but I’m like, okay, that’s it, that’s it. You know? So you kind of have some extra services in there.[00:53:53] Nathan:Yeah.To be clear, you don’t want to let your friends, even if they live in the same town, as you convince you to like change your agency,[00:54:00] Sean:Nathan’s very convincing.[00:54:03] Nathan:I distinctly remember. I even invited you over for dinner and convinced you of it,[00:54:07] Sean:How am I supposed to say no,[00:54:08] Nathan:Exactly.[00:54:10] Sean:You made an offer. I couldn’t refuse.[00:54:13] Nathan:But in that, so you’re talking about like what you’re selling to someone who might not be able to afford it, or like you might make a course that you charge $5,000 for that is absolutely worth every bit of that when in the right person’s hand and apply it in the right way. But you’re going to have a bunch of people trying to buy it, who like, aren’t that person who’s going to get the leverage to make it a clear 10 X value or something like that. And so you might have in this position where someone’s like, oh, $5,000 is expensive. Should I buy it? I don’t know. And you’re like, honestly for you, I don’t know if you should buy it.Like you’re not in the target market and that’s, that’s $5,000 one time in the case of this. And this agency, this productized service, I guess, $5,000 a month. And so actually two of those clients, and you’ve got a six figure a year agency business. And it’s just interesting. The thing that you said made me really drove home the point of, there’s not necessarily a correlation between effort and income and, and effort and output. And so you found a model and kept, kept tweaking until you found one where it was like, look, there’s a ton of work that goes into this, obviously. And there’s a bunch of really smart people working on editing and transcribing and captioning and everything in the show. but like, it, it doesn’t have to be crazy complicated, whereas some of the other business models that you and I have both tried have been way more effort for way less.[00:55:40] Sean:Yeah. And what can really hold you back is not realizing who you’re trying to market to. And. getting Talked down in your prices by accidentally catering to the wrong people. So like people who can’t afford your services, you could get on call consultation calls with them. And they’re just like, I just don’t have this much money and can you do discounts?And you, you almost start to feel bad. Like, you know, how can I charge this much? I must be charging way too much. And it’s like, or maybe you’re serving the wrong customers. Like, you know, when you talk to the right people, that may actually be really cheap. I remember when I started designing logos, this is like a decade ago.My first logo, I charged like 150 And then, once I sold that I got enough confidence to charge 300. And then I was like, I, you know what, instead of doubling again, I’m going to charge $750[00:56:30] Nathan:Ooh.[00:56:31] Sean:I did that. And you know, I’m like slowly building on my portfolio and I got up to like, $1,500 and clients were paying that and right around there, you start to get people resisting.Now you’ve got a price with a comma and it gives people. pause And they’re like, can you come down? Can you do a little bit cheaper? And it’s so tempting. You, you want to do that because you want the job. You, you want them to be happy. It could be a good portfolio item. And I remember just kind of fast forwarding through this, but like, you know, just mindset shifts and stuff.Eventually I got to the point where there was this startup out of San Francisco they wanted a logo. And I was like, this would be really valuable for this company, you know? And I somehow mustered up the courage to charge $4,000. And I found out later from a friend of a friend, you know, from someone that worked there that they thought I was like super cheap because someone else they knew or some other agency was going to charge $25,000 And I was like, wow, like I’m over here. Just like feeling bad about my prices, thinking I’m going so big. And really I’m. I was just serving the wrong code.[00:57:34] Nathan:Yeah. And it’s so interesting because the person who’s only able to pay $500 or only thinks the logo is worth $500. It’s not that they’re wrong or they’re devaluing your service or something like that. It’s that maybe it’s for a side project or it’s for a business that just got off the ground or any of that. And so it’s not worth getting offended over or something like that. It’s like, we just don’t have product market fit, like product customer fit. It’s not a thing here, you know, and my services are better for, you know, bigger, more established companies. So the saying no to, to, services, occasionally getting talked into specific services by your somewhat annoying local friends. but then where does it go from here as far as what are you looking to, to, to add more clients and, and keep scaling and growing?[00:58:30] Sean:Yeah. That’s what we’re trying to figure out right now is it’s always tricky. It’s a blessing and a curse when you have an audience, because it can kind of create false product market fit. Like you, you think you have something and then you exhaust your audience and then you’re like, oh, like I kinda need to figure this out.You know, that’s like, we’re experiencing that right now because like, I was getting like 40% close rates on consultation calls on sales calls, and now we’re not, and it’s. Oh, no, like what’s happening. And it’s like, well, I think those people probably knew me for several years, you know? And then like, there’s just all this trust and still Nathan we’re a year in and we don’t have, like, we don’t have a proper website for, for the agency.It’s like a page with a form. That’s it? There’s no, there’s no examples. There’s no case studies. There’s no portfolio item and we’ve made it this far. but you know, when people don’t know you, they need that social proof and they want the examples and they’re looking for past versions of success. And like the sales cycle is a little bit longer.And so that’s where we’re at right now is like figuring out kind of like Mar marketing channel fit. And I know well enough to know, like it’s better to, and back to right advice, wrong time. it’s a good idea to be everywhere if you can, you know, cause different people consume on different platforms.Even if you don’t use Instagram. Other people do, even if you don’t use YouTube, other people do it’s. Beyond LinkedIn, even if you don’t, you know, that like there’s, there’s some, there’s some sound reasoning to that at the same time. You don’t want to try to do all of that all at once, you know, and, and spread yourself too thin, like pick one channel, do one channel.Well, and when you’ve got that down and it’s easy and you have systems and it’s not taking too much time, then expand to another channel with the goal of like, ultimately diversifying kind of like investments. You don’t want to just diversify all at once. You know, like, like try some things out, you know, focus on one thing at a time, see what works for us.I, at least I know that much. And so it’s like, okay, I’m not trying to do every version of marketing, you know, like, oh, do we do affiliates? Do we do ads? You know, do we do content? Do we do cold outreach? You know? I’m trying not to do everything at once. So we’re kind of dabbling in one thing at a time and seeing what fits.[01:00:48] Nathan:So how many clients do you have now for the agency that are the consistent tenders?[01:00:53] Sean:Not a lot. It’s still very small. And we’ve had like, I it’s under a dozen cause like some, we had like several accounts, like not renew and stuff. So it’s still very small. And for three or four months, I stopped marketing and sales completely because I did not want to break this thing with scale because I notice things in operation that were the operations that were not going well.I’m like, this is going to be really bad. Like if we just sign more clients, it’s going to be really bad. So, I had clients pay upfront for like six months or 12 months of service, which kind of gave us time to focus on operations. And now everything’s humming along smoothly. Like the systems we’ve built can support like dozens or hundreds of accounts, even like, we don’t need it right now, but it’ll support where we want to go.But it’s still a very, it’s actually very small, like again done, like almost no marketing a year end, still don’t have a website. Like it’s pretty much just been all internal focused.[01:01:52] Nathan:One thing that I’ve respected a lot about how you’ve set it up is like, as a client, I could see it produce that they could see it as a client. And then, as, as a friend and, you know, business peer and all that. It was the times that you’ve tried things and then been like, oh no, we can’t do that. We can do this version of it where like, well, I came, remember what we shifted in, in the production of this podcast.Right. But we, we added the, like the video service, because most people who come to you, you know, have their show being produced already. And, and then they’re bringing it and say, Hey, can you make clips? And, and all of that, of this. And so, you know, we added things and then you, then you tweaked and changed it because you’re like, yes, I can totally make this work for this client.And maybe even five more, but like at 50 clients at a hundred clients, there’s no way that this will ever work. And so we’re not going to do it now. And I have a ton of respect for that.[01:02:42] Sean:I’ve scaled a bucket of holes before, and it’s like, I don’t want bigger problems. No, thank you.[01:02:49] Nathan:Yeah. okay.Something that you also preach a lot that I really appreciate is. this specifically, if you’re doing a podcast, like turn on the camera, why?[01:03:01] Sean:Yeah. If you’re doing a podcast, you’ve got to film it. There’s so much more you can do with this. We’ve just found when you try and repurpose audio files, it just doesn’t perform as well. On Twitter. People resonate with people’s faces and they connect with humans. So just turning on your camera for your own show, even if you don’t want to post it yet, even if you’re not repurposing it, at least you have it.We have a lot of clients that have just a backlog. They had a podcast, it goes out audio only. They don’t even produce it video, but behind the scenes, they recorded the zoom calls. So they’ve got all the zoom recordings in the cloud and they’ve just got this massive backlog. And now we can repurpose that and resurface it and put it on the different plans.It just gives your content legs. It’s like thinking of like a wood pallet and you, you know, you, you build something on it and you want to move that. It’s like, it can’t go anywhere. It’s like, it puts wheels on that pallet, you know, your content. So even if you’re on someone else’s podcast is what I tell our clients.If, if they’re like, I don’t know if I record enough content, it’s like, you probably do. And you’re just not like making use of it. Like anytime you probably get, podcasts, interview requests, sometimes you’re like, I don’t know if I have time for this is the audience big enough? I feel bad asking that question, but you’re thinking about it, right?And like a way that will help you create free content and justify going on. Maybe those smaller shows and building those relationships is even when you’re on an audio only podcast interview, turn on your own. And record yourself, use your webcam, use your iPhone. Don’t overthink it. Don’t do the external DSLR, Thunderbolt HD, my convert.Like I know it gets complicated. Don’t go down the rabbit hole, but just film yourself. And now you’ve got video. You can do stuff with that. You can repurpose because you’re probably already recording the content that.[01:04:51] Nathan:Yeah. And that, that’s something that I think about all the time, because exactly we talking about, when you go on that show, you’re like, can I justify the time for the size of the audience or any of those things? And it’s like, yeah, you can, if you’re going to reuse that elsewhere, like you told a story on that random podcasts, it’s going to go out to maybe a hundred people or something like that. And if you can pull that story back and say like, oh yeah, but I’m going to have it, you know, turned into clips and transcribed and it’s going to turn into a, a, a, another blog post or another idea then it’s totally.[01:05:26] Sean:And here’s a free idea. I tell my clients this as well. I’ll give you two. One is a live-stream Q and A. There’s just such a win. You’ve got the live engagement. You’ve got people asking you questions, which essentially writes the titles for you. It’s reading their minds. But then you’re also maximizing your input.You’re leveraging your time where you could show up for 30, 40 minutes, answer 21 questions, and then there’s three weeks worth of daily clips that you made in like half an hour. So, Q and A, even if, if you don’t have a big enough audience for live, do async. Send out an email to your list, add it to your “welcome” auto-responder.“Hey, what’s the biggest struggle around X?” Put that in a spreadsheet, show up with an outline, and just knock it out. A week’s worth of Daily Content for you right there. The other idea is, I was talking to someone who coaches founders, and he had a rate for every-other-week calls of a certain length, and access to a Slack and stuff like that. It was like maybe $850 a month.What you could do is charge $1,200, but say, “I can do $850 if I can record this,” and repurpose the content. Maybe you could come up with some arrangement where it’s pinned on your video, and it doesn’t show the person, or you edit out sensitive details, but you’re already giving advice on your coaching calls, on your consulting calls.You’re creating content. All it takes is just like a little tweak to expectations you set with your clients, and then you don’t have to create more. You have content, right?[01:07:03] Nathan:Oh, there’s so much good stuff. It really just takes this idea of creating content, being a huge hurdle that you’re trying to carve out time and trying to make it happen, and turns into something that you can show up pretty consistently and make it happen, in a somewhat meta sort of thing.Your team has mentioned that they’d like episodes to be between 50 minutes, and an hour and 10 minutes, just for finding the right amount of content. So we’ll try to stick with them that. So, I think you might be the only one of the only guest that has come on the Nathan Berry show twice, in his relatively short run of, I don’t know what we’re at, 45 episodes or something like that.[01:07:43] Sean:Yeah, I think you’re over 50.[01:07:44] Nathan:Over 50. Alright. See, I like that. You noticed that side of it, but we’ll have to do this again because it’s just so easy, and we can riff on whatever we want and it’s it’s great content.[01:07:56] Sean:Well, thanks so much for the opportunity. Nathan always love getting to chat with you.[01:08:00] Nathan:Yeah. So where should people go to learn about Daily Content Machine to follow your stuff? Are you podcasting? What what’s going on?[01:08:08] Sean:Yeah. DailyContentMachine.co. That’s going to take you to our page with a form on it that’s not very fancy.I have a video there. If you’re listening in the future the website’s awesome. The transition to the animation. The illustrations. It’s beautiful. You got to check it out.No, I’m just kidding. But you can follow me on Instagram, Twitter, that kind of thing @SeanWes. So S E A N W E S.[01:08:37] Nathan:Sounds good. Well, thanks for joining me.

Dave Pell has been writing online for almost as long as the internet has existed. His popular newsletter, NextDraft, has over 140,000 subscribers. NextDraft covers the day’s ten most fascinating news stories, delivered with a fast and pithy wit.Dave has been a syndicated writer on NPR, Gizmodo, Forbes, and Huffington Post. He earned his bachelor’s degree in English from U.C. Berkeley, and his master’s in education from Harvard.Besides being a prolific writer, Dave is also the Managing Partner at Arba, LLC. For more than a decade, Arba has been angel investing in companies like Open Table, GrubHub, Marin Software, Hotel Tonight, Joyus, and Liftopia.In this episode, you’ll learn: How Dave merged his two writing passions into a successful product The key to building a strong relationship with your audience How Dave dramatically increased signups to NextDraft Links & Resources Flicker Unsplash Fareed Zakaria Jim Rome The Skimm Morning Brew The Hustle Spark Loop Sam Spratt Dave Pell’s Links Dave Pell on Twitter NextDraft newsletter Dave’s new book: Please Scream Inside Your Heart NextDraft app PleaseScream.com Episode Transcript[00:00:00] Dave:If you have something to say in one way or another, the internet is a great place for people to figure out a way to receive it. So, that’s pretty powerful and still excites me. I still press publish with the same enthusiasm now than I did when the internet first launched.[00:00:23] Nathan:In this episode I talk to Dave Pell, who has been writing for basically as long as the internet has been around. He’s been an investor since the early days. He’s been writing since the.com bust, and even before then. He writes his popular newsletter with 140,000 subscribers called Next Draft.We have this really fun conversation about writing. His writing process. How he grew the newsletter. Bunch of other things that he cares about. Even a few things that I was interested in, like he doesn’t have his face in photos on the internet very much. He has his avatar instead. So, just getting into why that is.He also has a book coming out soon. It’s called Scream Inside Your Heart, which is a fun reference to some memes from 2020. So, enjoy the episode. There’s a lot in there.Dave. Welcome to the show.[00:01:12] Dave:Thanks a lot for having me on.[00:01:14] Nathan:Okay. So you’ve been doing this for a long time. You’ve been writing on the internet since the .com era. So, I’m curious maybe just to kick things off, what have you seen—I realize this is a giant question.What have you seen change? What are some of those trends that you’ve seen, that you either really miss from the early days, or some of those things that you’ve held onto from the early days of the internet, that you’re really still enjoying?[00:01:46] Dave:Yeah, that is a pretty huge question, but I’ll give it a shot. The thing I miss from the early days of the internet is that our democracy was not being destroyed by the internet in the early days of the internet. So, everything we thought we were building, basically it turned out to be the opposite of what actually happened.The part about the internet that I still feel is there, although a little bit less so because of the big companies have sort of taken over all the platforms and stuff, is just the idea that someone can have a passion or a creative output that they want to share with the world, and they can mold internet tools to fit their skills, and then use the internet to broadcast that out, and still become sort of pretty popular withour the “OK” of some gatekeeper at a publication, or at a television studio, or whatever.The indie spirit of the internet still lives on. It ebbs and flows, and has a lot of different iterations. But that was the thing that excited me the most when I first played with the internet. And that’s the thing that continues to excite me the most now.[00:02:57] Nathan:I always think of the newsletter, and your newsletter in particular, is that indie spirit. Is that what you see most commonly in newsletters? Or are you seeing it in other places as well?[00:03:10] Dave:I see it in podcasts. I see it in newsletters. I see it in people sharing their art, sharing their photography on Flicker, and up through the more modern tools. I go to a site called Unsplash all the time to look at images, and it’s just basically regular people sharing their images.Some of them are professional photographers, some aren’t, and they’re getting their work out there, and then some of them probably get jobs out of it and stuff like that. So, just the idea that you can have some kind of creative output and have a place to share it. And try to get an audience for that is really inspiring.It’s a lot harder than it used to be because there’s a few billion more people trying to get attention also, and because there are more gatekeepers now. So, you have to, hope that your app meets Apple’s guidelines, or that different products you might want to share on the internet have to meet certain classifications now, whereas they might not have in the very early days of the internet. But in general, if you have something to say in one way or another, the internet is a great place for people to figure out a way to receive it.So, that’s pretty powerful, and, still excites me. I still press published with the same enthusiasm now that I did when the internet first launched.[00:04:32] Nathan:Yeah. So let’s talk about the main project that you have right now, which is Next Draft. Give listeners the 30-second pitch on Next Draft, of what it is.[00:04:46] Dave:Sure. Basically I call myself the managing editor of the internet. What I basically do is a personality-driven news newsletter where I cover the day’s most fascinating news. I cover 10 stories. A lot of times in each section there’s more than one link. I give my take on the day’s news, each individual story, and then I link off to the source for the full story.When I first launched it, I called it Dinner Party Prep. I provided enough information for you to sort of get the gist of the story. And if there’s topics you want to dig deeper, you just click and, you know, go get the story yourself. So that’s sort of the overview of it.[00:05:27] Nathan:Nice. And you said that you’re obsessed with the news maybe in a somewhat, even unhealthy way. why, where did that come from?[00:05:36] Dave:Yeah. Well, nothing, nothing about my relationship with the internet is only somewhat unhealthy. it’s all extremely unhealthy, but, both my parents are Holocaust survivors and, when I was growing up, news was just a very big part of our daily lives, especially when my three older sisters moved out and it was just the three of us, that was sort of our mode of communication.We talked about the news. We watched the news together. Fareed Zakaria is basically the sun my parents always wanted. but so I got really into the news and being able to connect the news to, our everyday lives, which of course my parents had experienced as children and teens and Europe during world war II.And also reading between the lines about why certain politicians might be saying something, why stories are getting published a certain way. So I just got really into that and I’ve always been into a and college, you know, I, I majored in English, but if we had minors at Berkeley, I would have minored in journalism.I took a bunch of journalism courses. I’ve always been really into the media, but not so much as quite an insider where I go to work for a newspaper, but more observing, the news and providing sort of a lit review of what’s happening and what has momentum in the news. So I sorta got addicted to it and, Also as a writer.My favorite thing to do is counter punch. I like to have somebody give me a topic and then I like to be able to quickly share my take, or make a joke or create a funny headline about that content. So I sorta took those two passions of the way I like to write. I like to write on deadline. I like to write fast and I like to counter punch and the content that I like, which is news, and I sort of merged those two things and created a product, and a pretty cool suite of internet tools to support that.[00:07:35] Nathan:Yeah. So that makes sense that you’ve identified the constraints that match your style and made something exactly that fits it. the deadline, like having, he, you know, coming out with something on a daily basis, is more than a lot of creators want to do. so what’s your process there?[00:07:55] Dave:Yeah. I mean, I should emphasize that I do it every day. Not because I think it’s some incredible draw for readers to get Daily Content. I do it every day because I’m addicted to it. If my newsletter had five stories in it, instead of 10, it would do better. If my newsletter came out three days a week instead of five days a week, I’m sure it would do better.If it came out once a week, it would do even better then you know, also if I had a more marketable or not marketable, but a more, business-oriented topic that was more narrow, it would do better. I used to write a newsletter that was just on tech and it was. Really popular in the internet professional community back in the first boom, I had about 50,000 subscribers and there were probably about 52,000 internet professionals.So I just like writing about what I want to write about and I’m addicted to pressing the publish button and I’m just addicted to the process. So I do it because of that. I’m not sure that would be my general advice to somebody trying to market or promote a newsletter.[00:09:01] Nathan:Yep. Are there other iterations, either ever before or things that you tried that you realized like, oh, that’s not a fit for your personality, your writing style?[00:09:09] Dave:Yeah. When I first started it, I actually, I’m an angel investor also and have been since, probably right after Google and Yahoo launched. so a while, and I used to, my passion has always been writing, so I wanted to mix writing into that, process. So I would send out 10. Daily stories, but they were all tech news related to the CEOs of the companies I worked with and a few of their employees, so that they wouldn’t have to spend their time reading the news or worrying about competitors or worry about what the latest trends in tech, where I would give it to them.And they could focus on doing their jobs and that sorta got shared and got out. so I did that for a few years. really, that was my iteration. I should’ve kept the brand. It was called David Netflix. not that it was a great name, but I’ve shifted brands about 40 times in my life. Cause I love branding and naming.I that’s another, maybe this is more of a cautionary tale than a lesson and newsletter marketing. I would stick with a brand if anybody has the possibility of doing that, that was a big mistake I’ve made over the years is having multiple brands. But when the bus came, the first internet bust, I basically was writing an obituary column every day and about companies that had failed.So I just decided, I wanted to expand it and I knew I was interested in much broader topics than just tech news. So I expanded it to all news, a critical point that, really changed Next Draft and got it to catch on and become more popular was when I decided to focus on making it more personality driven and less, less overwhelmingly, providing an overwhelming level of coverage.I used to think that I had to provide all the news in the day because people would sort of, depend on me to provide their news. I was sort of selling myself as your trusted news source. So I would include a lot of stories that I didn’t have anything to say about because they were huge news, you know, an embassy closed in Iran or whatever.That was huge international news, but I didn’t necessarily have anything to say about that that day. So after a while I decided, no, I’m not going to do that. I’m just going to limit it to 10 items. And I’m going to focus that on what I think is the most fascinating and think of it less like a curation tool and more like, a, modern day column.I think if the column newspaper column were invented today, it would look a lot like Next Draft people would sort of share their takes and then provide links off for more information. once I did that, it was a big change. People started signing up much more readily and, once I stopped trying to be exhaustive.[00:11:56] Nathan:That makes a lot of sense to me. I think that that’s something you see from a lot of creators is that they’re, they’re trying to find some model. That’s like, this is my idea of what people should want, you know, rather than what they end up doing, eventually it’s coming to, it’s like, okay, forget all of that.This is what I want. And I’m going to make that. And then people like me can find and follow it. And people who don’t can, you know, do their thing. Can you go find one of the other million sources on the internet?[00:12:21] Dave:Yeah. When I think of the people that I like to follow or have followed forever on the internet, all of them are that ladder. They just do it their way. They have a design, they want, they stick to their guns. They say what they feel like saying. they decide. what the personality of the product is.And, they move within that. I always find that to be the most interesting thing, especially when it comes to something like newsletters. I really think newsletters are more like a radio talk shows than they are like other internet content, podcasts to a certain degree as well. But I always feel like I listened to are used to listen a lot to this radio, sports caster named Jim Rome.And whenever he would have a new city that he was launching and he would always give the same speech on the Monday that they launched saying, just give me a week. You might not.Get the vibe of what we’re doing today. You might think it’s okay, but not great, but just give it a week and listen, and then decide if you like it or not.And I sort of feel like that’s how newsletters are your relationship with your readers sort of creates this, sort of insider-y voice and communication that, you, it takes a little while to get into the rhythm of getting it. But once you do, then it’s like this familiar voice or this familiar friend that you feel like, even if you didn’t read it for a few weeks, you can start a conversation with that person right away easily.That’s how I think the voice of a newsletter is most effective. So that’s why I’ve always thought of it. More of what I do is sort of a textual talk radio, more so than a blog or some other format[00:14:01] Nathan:What do you think, or what would you say to someone who maybe had 10 or 20,000 subscribers and felt like their newsletter had gone a bit stale and maybe their relationship to it had gotten a bit stale or they’re in this, this position of writing things that no longer have their voice, how would you coach them through like bringing their voice and personality back into it?[00:14:22] Dave:I mean, it’s definitely hard. it’s hard doing something that you do alone and, something that is often hard to really get off the ground or get to grow, especially when you’re on a platform like the internet, where every day, somebody does something and 10 seconds later, they’re like internet famous and you’re trying day after day.So, I mean, the first thing. Is that you really have to be interested in what you you’re passionate about. and focus in on that, because that will alleviate a lot of that stress. Like, do I feel like sending it today? I’m a too burnt out. What’s the point? I mean, not that those feelings don’t happen. I had those feelings as recently as an hour ago, when I press publish, I have those feelings and disappointments constantly, you know, that’s part of being a creator of any kind.Maybe that word is sort of, sort of goofy, but anybody who’s putting themselves out there and putting content out, you know, you have that feeling all the time. If you’re an indie, and you’re doing it all day in front of the computer by yourself, then that’s even more powerful because, you know, if you work at a big company or everybody’s working on the same goal, or even in a small group, you can sort of support each other and, maybe even bullshit each other at some cases where, oh, no, this really matters.You know, where, if you’re by yourself, that has to be pretty self-sustaining or self-sustaining. I do have a friend or two that I always share blurbs with who, one of my friends Rob’s, he proves almost all of my blurbs, so it’s nice to have that virtual office mate. He’s not really officially part of Next Draft, but you know, I don’t think I would do it as easily or as, for as long if it weren’t for him because he’s like my virtual friend on the internet that says, oh, come on, let’s get it out today or whatever.So I think that’s helpful to have a support team or a couple people you can count on to sort of give you a boost when you need it. But the key really is, is that it’s gotta be something that you are passionate about, both in terms of the product and in terms of what you’re focusing on, because if you feel strongly about it, then it really.I don’t want to say it doesn’t matter if people enjoy it, you should take cues from your readers. What are they clicking on? What are they reading? What are they responding to? But at the core, it’s gotta be you because that’s what gets you through those down points? you know, I had a weird thing because I write about news.The general news, world basically benefited dramatically from the Trump era because everybody was habitually turning on their news, 24, 7, and refreshing and Whitey and Washington post and checking Twitter every two seconds to see what crazy thing happened next. And we’re all poor sorta,[00:17:01] Nathan:Wreck to watch.[00:17:02] Dave:So everybody was really into it and it created.Unbelievable platform for people to become media stars. You know, Trump was bad for democracy, but he was great for media. Great for creating new voices out there. whether we like it or not. for me, it was different because I wrote about all news. I wouldn’t say I was apolitical, but I wasn’t heavily political.The Next Draft had plenty of readers from both sides of the aisle. when Trump came around, it was like one story every day, basically. So it really limited. I would get emails from longtime readers all the time that said, Hey, can’t you cover something other than Trump every day?And I say, Hey, if you can find the story for me, I’ll cover it. This is what every journalist is on. Now, the people who used to cover the secret service around Trump, the people who used to cover sports are not talking about Trump because of a pandemic relation ship to it. The people who aren’t entertainment are talking about Trump because they can’t believe that anybody voted for him, whatever the issue was, every dinner party was about Trump.So it was really a bummer for my brand and my product. Actually, it became boring in some ways to me to have the same story every day. And it became, I think frustrating to my readers.But during that era, when it was happening, I had to make a decision. Do I become more political and go full on with this?Or do I sort of try to. Do what I would call a falsely unbiased view or a, you know, false equivalence view that we saw in the media where there’s both sides to every story. And you have to pretend they’re both accurate, including one guy saying to put disinfectant into your veins. And the other person’s saying to wear a mask and take a vaccine, but those things get treated as equal somehow because the president said it.And I really decided, you know, more important than keeping readers is that I’m true to my own sort of ethical standards. In a moment that called for it, at least for me. So I became more political. went into it and I said, what I believe and still believe is the truth, you know, about what was happening with Trump and Trumpism and our slide towards authoritarianism.And I know that this is a podcast more about newsletterish than it is about politics or news, but I’m just sharing that because that’s the kind of thing that kept me going. and the people who really cared about what I was writing, appreciated it and would email me and say they got something out of that.And most importantly, my mom would say, yeah, you made the right call. Or my dad would say, yeah, you got that. Right. And ultimately, When it became a sort of a bummer period for me, which I would say 2020 was because of all the horrible news. And, I was writing a book about the year. So I was like living, July of 20, 20, well writing about March of 2020, which I don’t recommend for anybody’s emotional health.And I just had to think like, what’s really important to me. Yes. I want to be funny, which I try to be in my newsletter every day. I want to be read my narcissism is as strong as ever, but ultimately I want to be able to look myself in the reflection of the, darken screen on the rare times that it is dark and say like, yeah, you told the truth and that kept me going there.So I think whatever your brand is, you know, it can be a newsletter about guitars, but if you have that sort of passion, And you have something you want to say, and you think is important to say it sort of gets you through those levels and your motivation. And if it’s not getting you through the lows and the motivation, there’s nothing wrong with saying, Hey man, this is not worth it.I’m going to go try to make something else. You know, it doesn’t have to be, you don’t have to beat a dead horse.[00:20:51] Nathan:On the political side. Are there specific things that you felt like it costs you opportunities that it lost you? Because I think a lot of creators, whether they talk about, you know, finance or photography or whatever, I’ll see these things. And they’re like this either directly relates to me and my audience and I feel like I should take a stand on it.Or it’s like a broader macro issue that I feel like we should talk about. And when you do, then there’s immediately, you know, somewhere between three and 300 responses of like, we didn’t follow you for the politics, you know, or like something like that. And your Instagram, DMS, or newsletter replies or whatever.[00:21:24] Dave:Yeah. it costs me a lot. Definitely it costs me readers or subscribers. It costs me, psychic pain because I was locked into a story that was just overwhelmingly, emotionally painful, really, and shocking and difficult to understand all the things that cause you sort of emotional exhaustion. We’re in the Trump story, especially in 2020, when it became a story about our own health and our kids’ health.And the frustration level just went through the roof. for me, professionalizing that content actually helps create a bit of a barrier to the feelings about it. Some of my good friends were probably more bummed during 2020 than I was because when the latest crazy story or depressing story would happen, I felt I had to. Ingest that content and then come up with, something cogent to say about it. And maybe hopefully funny to make it a little bit of sugar to take the medicine and then get it out to people. So I’ve always felt that being able to do that, sorta created a barrier between myself and actually feeling something.So that’s another thing I like about the newsletter probably at least unconsciously. but yeah, there was a lot of costs in terms of readers, for sure. Hate mail. but there always is, you know, Today. I would say I get much more hate mail from the far left. If that’s what you want to call them. People who feel like every joke is like an incredible triggering a front to their existence or any hint that you mentioned somebody as attractive.I’ve gotten hate mail because I implied that Beyonce is appearance was part of her brand. I mean, it’s totally crazy, but, It’s those extremes. You have to be able to turn off. You know, a friend of mine used to work at a major, be the editor of a major American newspaper. And he said every Friday they would get together and they would play the craziest, calls to the editor.They had a call line. In addition to, you could send a letter or you could call, leave a voicemail about something you were upset about in the coverage. And they would just gather around and have drinks on Friday. Listen to this because of course the people who are calling this line are almost self-selecting themselves as a little bit wacko and their takes were usually pretty extreme.The internet, Twitter, social media, Provides, greases the wheels for those people to be more prevalent in our lives. But I think it’s really important to know that that’s a real minority of people, somebody who sent you a hate mail, that your joke was so offensive, or they can’t believe you mentioned that people ever watch pornography on the internet or any of these other things, it’s this tiny minority of people.And then it’s one step crazier that they felt like they had to contact you. So that’s a really hard thing. I think about being split, particularly the newsletter game, because anybody can hit reply and you’re going to get many more replies from people with crazy complaints, than you are from people with really thoughtful responses.Not that those don’t come and those are valuable and I love getting those, but you get many more from people that just have really bizarre. I mean I could list probably for hours to crazy things that people send me that they’re mad about, you know,[00:24:50] Nathan:Is there something specific that you do? Like one thing when I get those replies, if they’re just like completely off the wall or abusive or something like that, I just scroll down and then click their unsubscribe link because, you know, they’re never going to know, and then I just have to show up in their inbox[00:25:07] Dave:Right.[00:25:08] Nathan:There’s something that you do.[00:25:09] Dave:That’s not a bad strategy. I like that. I do do that occasionally for sure. occasionally I’ll just go to Gmail and just, create a filter for that email to automatically go to my trash. if it’s like a hardcore right-winger, that’s telling me how stupid I am about ivermectin and that, you know, people should be taking horse dewormer and I’m just not getting the truth.And that Trump is awesome and that, Whatever. I usually just delete, honestly, because I don’t see a big benefit to replying to somebody, especially if it’s like a rabbit email, you know, they’re looking for a reply, they want the conflict. A lot of people sleep easy with conflict. That’s one of the lessons of the internet that I learned when I was first starting on the internet, you know, David edix sort sorta became popular because somebody that had a blog with a similar name, that I hadn’t heard of, complained that I sort of stole his name because his name was also Dave.And I had got like, probably about three or 400 emails saying, you know, with expletive saying what a horrible person I was. And I also got about 3000 subscribers and at the time I had about 30, so. I didn’t know how to respond. I felt like, wow. Number one, I didn’t know that guys had the product with the same name.Number two. My name was different enough. Number two or three were both named Dave. I mean, who cares? You know, and plus I don’t want to be attacked by anybody. So your first reaction is to respond and a slightly older, although not noticeably these days with my gray beard, slightly older friend of mine who had been in tech a little longer, said, don’t respond.This guy lives for conflict. You guys are going to fight. There’s going to be this public thing. You’re going to be up all night and he’s going to never sleep so easy. So, I took that to heart and didn’t respond. And I, I think about that a lot when I get rabid emails from people, Mike exception, actually probably my weak point really is from, more my side of the political spectrum, where people who are generally liberal, but are just so extreme for me.In terms of being triggered or having a joke, be every joke, be inappropriate. That those people, I actually do feel like I want to respond to because, I, I don’t think I can really motivate or move, somebody who was on the opposite end of the spectrum and is sending me hate aggressive, hate mail, but maybe I can move somebody who’s just a little bit different than me, or a little bit more extreme.I will respond to those, although I’m usually sorry. The one other thing I always respond to is if people have been reading, they say, oh, I’ve been reading you for years. And, I wanted to ask you a couple of questions about this book that you wrote before ordering it. And I’m like, just order the damn book. that’s probably my most common email to people these days. It’s actually remarkable how many people says, wow, I I’ve been reading you for years. I share you with all my friends. something, when my sons come home from college where it’s always talking about, Dave said this, Dave said that, before I buy your book, I just wanted to ask you a couple of questions to make sure it’s going to be for me.I’m like I worked on something for an hour and it’s like, your family is talking about it. What, just by the thing I worked on for a year, you know? So those kind of things, personal frustration, I respond.[00:28:37] Nathan:Yeah, that makes sense. okay. I’d love to talk about the book some more, but before we get into that, there’s two things I want to talk about. The first one is like, how do you measure success for the newsletter? What’s the thing that you’d like to, cause I don’t think it’s, you’re pursuing the monetary side for this.It sounds like the monetary side comes from investing and, and then what’s success for the newsletter.[00:28:59] Dave:I mean, I have had right now, I I’m just marketing my, my own stuff. And during the pandemic I marketed non-profits, but, that had to do with either the pandemic or, the democracy issues that we were facing. but I have made decent money from selling straight sponsorships. Year-long sponsorships to people, which I highly recommend.I think some of the ads that people put into his letters that go by clicks or whatever, unless you have a massive audience, it’s hard to make much money, but if you pitch to some company that is a like-minded brand, Hey, you’re going to be my only brand for a year. And anytime you have special events, I’m going to mention it.Then you can say, okay, you have like, you know, 20,000 readers or a hundred thousand readers that can make a difference to a brand to say, yeah, it’s like a rounding air show. We’ll give you 20 grand or a hundred grand or wherever it comes in there that you can actually make a decent. Living in terms of writing.So that always worked better for me, but no, my, my internet life is really all about narcissism and, clicks, you know, the dopamine, I just want reads. I’d rather you subscribe to my newsletter than pitch me your startup company. I just, that’s what I want the most. So more numbers, more opens, more reads, more subscribers.And unfortunately that’s probably the hardest thing to get also, especially in a product that is sort of viral. I think newsletters are sort of viral, but it’s better if you have a team and some tools to really get it going. That’s, you know, sites like the Skimm morning brew and the hustle. They have teams that are really growth hacking and focusing on that and having rewards programs and ambassador programs.The reason you see that is because.Newsletters themselves are not really inherently that viral. Yes. Somebody can forward it to one person or whatever, but it’s not as viral as a lot of other forms of content where you can click a button and share it with all of your followers, like a Facebook post or a tweet.So yeah, the thing that matters to me most is probably the hardest to get in the newsletter game, but that’s the truth[00:31:10] Nathan:Yeah. Well, I think the, the point on like newsletters don’t have a distribution engine. There’s no Facebook newsfeed, YouTube algorithm equivalent for newsletters. And so it really relies on either you posting your content somewhere else, whether it’s Twitter or YouTube or medium or something that has an algorithm or your readers saying like, oh, I read Next Draft.You should too. There’s not really something else in there. Have you looked at, or I guess if you have thoughts on that, you comments on it, but then also have you looked at launching an ambassador program or, or an actual referral program?[00:31:44] Dave:Yeah, I’ve thought about him. And now over the last year, there’s been a few tools that have come out a few. I think X people from sites like morning view Ru, and some other sites that have sort of perfected some of these marketing programs have, sort of come out with these tools. I’ve messed around with them a little bit.Some of them still require I find, some technical ones. so I, I have like an engineer who works with me on Next Draft, like as a freelance basis every now and then, but it’s not always easy for me to launch stuff that requires a lot of a moment to moment technical support, and management, because it’s just me using a lot of, they’re customized, but they’re over the counter tools.So I’ve thought about a lot of them, but I really haven’t tried it that much.I want to though I do want to do that. I would like to do one of those programs, especially where you get credit for referrals. I think that’s the best kind of model. So there’s one called spark loop.[00:32:51] Nathan:Yeah, we actually, I invested in spark loops, so we[00:32:54] Dave:Okay.[00:32:55] Nathan:Decent portion of that business, so good.[00:32:58] Dave:Oh, nice. Yeah. That one, if it was just slightly easier, I know that it’s probably difficult to make it easier because, there’s so many pieces. They have to have your subscribers. I have to have my subscribers, but that is, does seem like a good product. And especially if they can, I think expand into like letting a person sell a product or whatever, get credited for sharing products that can be even bigger.But yeah, that kind of stuff is really powerful for sure. And I, I do want to get into that. it’s more just inertia that I it’s just a matter of sitting there for the, an amount of hours that it requires to get it going.But I do think that’s a great thing for newsletter writers to do, and I’m pretty surprised that more newsletter platforms don’t build it right in.I think that’ll probably change over time too. Maybe you guys will get acquired by.[00:33:48] Nathan:Yep. No, that makes sense. I know for convert kit, we wanted to build it in, it looks at the amount of time that it would take and then said like let’s invest in a , you know, and then roll it into our offering.[00:33:59] Dave:Yeah, it’s hard. It’s hard not to take that stuff personally, too, you know, for people that do newsletters, you think you’re going to put a thing on there and say, Hey, you know, it’s just me here and you always read my newsletter and click. I know you love me so much. Can you just do this to get a free whatever?And it’s, you know, sometimes not that many people click, you know, or other times like they click just as long as there’s the free item. So there’s a lot of ways to get depressed. Like I had things where I say, Hey, the first a hundred people who do this, get a free t-shirt or whatever next strap t-shirt.And those hundred people will literally do what I asked them to do in like 34 seconds, you know? And then it like stops after that. The next time you ask them, if there’s not a t-shirt. But it’s not you, you know, if you go to a baseball game or a lawyer game or whatever, you know, people sit there, they don’t even cheer as much for the team as they cheer when the guy comes out with the t-shirt gun.So it’s like, people love t-shirts more than they’re ever going to love you. And you have to go into these things with that in mind. there’s no way, even if it’s, even if you’re XX large and the t-shirt is, you know, petite, it’s still worth more than you are. And the average mind of the average person.So you have to go into all of these things thinking, I hope this works like crazy, but if it doesn’t tomorrow, I open up the browser and start writing.[00:35:19] Nathan:Yeah. That’s very true. I want to talk about the growth of the newsletter. I was reading something, which I realized later was back in 2014, that you were at around 160,000 subscribers. I imagine it’s quite a bit larger than that now. And then I’d love to hear some of the inflection points of growth.[00:35:35] Dave:Yeah, I’m not, I’m not sure. I might’ve, I don’t know if I lied in 2014, but now I have about,[00:35:41] Nathan:Quoted it wrong.[00:35:42] Dave:No, you might’ve got it right. I might’ve exaggerated. Maybe that was a including app downloads and a few other things. Yeah. I have about 140,000 or so now, so that would be making that a pretty horrible seven years now.You’re depressing me.Your listeners should just stop, stop writing newsletters. It’s not worth the depression[00:36:02] Nathan:Just give up now[00:36:03] Dave:Yeah. And by all means if Nathan goals do not pick up. no, yeah, I probably have it 140,000 on newsletter. Made my newsletter. It’s hard to believe in this era of newsletters actually, but when I first launched Next Draft, I noticed that even people who would send in testimonials or that I would ask for testimonials would say, basically something to the extent that even though email is horrible, this is the one newsletter I I’d sign up for whatever.And I kept thinking, man, that’s a bummer that I’m starting out at this deficit, that people have a negative feeling about the medium. So I, since then I’ve always made it my goal to. Have the content available wherever people are. So the newsletter is certainly the main way that people get next job, but there’s an app for the iPhone and the iPad there.That’s the first thing I launched because I wanted to have an alternative for people who just hate email too much. So now you go to the landing page, it’s like, Hey, if you don’t like email, here’s another version. I have a blog version. I have an apple news version. I have an RSS version. I’m lucky enough to have a really good, WordPress custom WordPress install that I just push one button and it pushes it out to all of those things.But I am, I’m a big proponent of just meeting people where they are. even, as an example, I recently launched a sort of a substance. Version of my newsletter under the radar. but when I redo my site, I’m going to make that more clear because if people already subscribed to like 10 sub stacks and they’re using their aggregator and they already have their email saved and they can just click a button, it’s like, I don’t care.You know, it takes me five extra minutes to paste my content into sub stack. So I just want the reads. I don’t really care about how they read it or whether they read it.[00:37:55] Nathan:Yeah. That’s fascinating. So then let’s shift gears a little bit. I want to hear about the book. first I wanna hear about the title. Would you have it on your shirt?[00:38:03] Dave:Yeah. That’s pretty embarrassing. I swear. I didn’t know it was video today, but I do have a shirt[00:38:06] Nathan:You’re good.[00:38:07] Dave:Otherwise I wouldn’t have worn. This would have worn my Nathan Barry’s shirt.[00:38:12] Nathan:That’s right. It’s in the mail actually. It’s[00:38:15] Dave:Oh, good, good.[00:38:16] Nathan:Big photo of my face.[00:38:17] Dave:Yeah. Convert kit. My wife converted to Judaism before we got married. So I have my own convert kit.[00:38:23] Nathan:There you go. Exactly. so I want to hear like what the book is about and then particularly where the title came from,[00:38:30] Dave:Sure.[00:38:31] Nathan:It made me laugh a lot when I heard it.[00:38:33] Dave:Oh, cool. That’s good. That’s a good start then. yeah, the title comes from, in July of the, of 2020 when the pandemic was really setting in and becoming a reality for everybody. this amusement park outside of Tokyo in the shadow of Mount Fuji called the Fuji queue. amusement park reopened.And they found that even though everybody w everybody was wearing masks, people were screaming so much on some of the rides, especially the Fujiyama roller coaster, which was their scariest ride, that they were worried about germs spread. So they sort of put signs around the amusement park saying, no screaming, you can come, you can ride and have fun, but keep your mask on adults scream.And it sort of became a little minor social media thing in Japan, where people were sort of making fun of them like, oh, they’re telling us not to scream. How can anybody not scream on the Fujiyama roller coaster? So in response, the, park management had to have their executives with perfectly quaffed hair and tie and colored shirts and masks on ride the roller coaster with a webcam facing them the whole time without moving a muscle.Cracking a smile or grimacing or screaming. And then at the end of the ride, when the rollercoaster stops, it says, please Scream Inside Your Heart.And that was always my favorite meme of, 2020. It went really viral. There was like t-shirts. aside from mine, there were posters memes. It sort of went crazy for about a week or two, which by 2020 standards is a pretty long time for a meme to last.And I just thought that made sense as a title for the book, because that’s sort of how we felt, all year that I dunno if we were screaming in our heart, but we were certainly screaming into a void. Like no matter what we sat or yelled on social media or complained to our family members or friends, it just kept getting worse.The year just kept getting worse. And, so the idea is that this book sort of, now you’re free to sort of let out the scream. And the book is it’s about 2020, certainly, but it’s really about the issues that led us to 2020. There’s a ton about our relationship to media and including my own relationship to media and how that got us into trouble.Some of the stuff we’re talking about today, how, technology has impacted our lives stuff. I’ve been sort of thinking about it, writing about for the last few decades, and a lot of the political hate that emerged. and, but it’s all within this time capsule of the craziest year.[00:41:12] Nathan:Yeah. Yeah. And so that’s coming out early in November, November 2nd. so you’re, it looks like you’re just starting the, you know, mentioning the promotion tour and all of that. is there a big, big push that comes with it or are you kind of, I, I’m always curious with people’s book launches, what strategy they take.[00:41:30] Dave:Yeah. I mean, I’m a newbie, so it’s, the whole process has been interesting to me working with a publisher, working with others, is not my forte. so I got used to that or I’m getting used to that and they’re probably getting used to it also because working with grouchy 50 something in these is probably not ideal, but, yeah, I’ve just been promoting it so far in Next Draft, but I’ve been doing, I have a PR company that’s helping me and I’ve been doing a ton of podcasts and I’m marketing it to my own readers.And then as it gets a little bit closer to the November 2nd date, I have a lot more stuff planned rut, a lot of influencers have early copies of the book, and hopefully they’ll promote it. And, I’ll call out a few favors from bloggers and hopefully newsletter writers. I feel like that should be my in theory.That should be my secret weapon because, in addition to being fun and creative, nothing moves traffic, except maybe Facebook, nothing moves traffic more than newsletters. I know a lot of people who run e-commerce companies and newsletters are always second, if not first, in terms of traffic drivers.So, I really think that, if some of my friends out there at morning brew in the hustle and the scam and all these other sites that sort of, have surpassed my size by quite a bit, put the word out that, one of their fellow warriors is, has a book out. That’ll probably move the needle even more. The media, I’m hoping to get stuff like that, but I really don’t know. I’m trying not to get my hopes up too much because, unlike a newsletter, it’s not just one day’s work, you know, you like worry about one word or one sentence in a book for like three weeks and then you put it out there and people are like, oh yeah, I’ll check it out sometime.Thanks. So, you know, that’s, you know, whatever that’s life as a, you put yourself out there, that’s how it goes. So I’m hoping it sells well. And, the more people that get it, I think some people, their first reaction is, oh my God, 2020. I don’t want to relive that again. But, hopefully people who know my brand and those that they share it with, know that it’s, you know, there’s a lot of humor and there’s, it’s probably 30 pages before we even get into the first event of 2020.So it’s, there’s a lot more to it and it’s sort of fun and crazy and tries to have the pace of a roller coaster. that was the other thing I took from the Fujiyama roller coaster.[00:43:59] Nathan:Yeah. So one thing that I’m always curious about with people who have like a prolific newsletter, you know, in your case of writing every day, and then like, for a lot of people, that would be a lot to handle of staying on top of a daily newsletter. And then you’re writing a book on top of that. How did you schedule your time?Were you blocking off like, oh, these afternoons are specifically for book, book writing. Cause you turned it around relatively fast.[00:44:24] Dave:Yeah. the newsletter is sort of like a full-time job. People always ask me, you know, when do you work on, or how many hours do you spend on it? I mean, I’m, I’m always looking for news, whether it’s on Twitter or friends, emailing me stuff or texting me stories, or just in conversations with people to see what they’re into or what stories are interesting them or what I’m missing.In terms of actual time spent like where I’m dedicating time. I probably do like about an hour every night, because the story has changed so quick. So I’ll do an hour of looking for stories every night. And then the next day I sort of lock in from about nine to one, usually, or nine to 12, where I’m finding stories, saving those stories, choosing what stories I want to go with and then actually writing the newsletter.All of that takes about anywhere from like two and a half to four hours, depending on the day I go pretty fast. When it came to the book, that was tricky. It was actually more emotionally tricky because like I said before, I was like, had to go back and write about, you know, Briana Taylor while I’m living another horrible act, you know, or even more so the Trump, you know, one crazy Trump thing and another crazy Trump thing and seeing the pandemic getting worse and worse.So that was stressful. But I found at the beginning I would try to write a lot at night and that was okay. But I found actually if I just kept going, in the day when I was already rolling and had written the newsletter and I was already in the group just to add on an hour or two to that was actually easier and more effective for me than trying to get going.But that’s just me. I mean, I just go by my it’s almost like my circadian rhythm or something like that, I almost never eat or consume anything before I’m done with next job except for coffee. I would keep that going, you know, once I would like, sort of have a sandwich or whatever, then it’s like, oh, let me just take a quick nap and then whatever.So, yeah, I tried to just keep it going. I always find the more consistently busy I am, the less I procrastinate. And if I take a day off or I take a few hours off, even then, between writing, it just, it takes me longer to get going.[00:46:37] Nathan:Yep. That makes sense. The habit that I’m in right now is starting the day with 45 minutes to an hour of writing and that’s working much better for me than like slotting it in somewhere else. So I think like w what I hear you saying is like, experiment and find the thing that works well for you.[00:46:54] Dave:Yeah. I mean, if you’re going to start experimenting almost every writer, I know not like newsletter writers, but just general writers, all do what you just described. They sort of pick a time in the morning and they get their output done. then the rest of the day, if ideas come to them or whatever, they jot it down, but they’re sort of powering in that morning hours.[00:47:13] Nathan:Yeah.[00:47:14] Dave:That’s probably a good one to try. Although, you know, some people just do it better at different hours. I’m sure.[00:47:19] Nathan:Yeah. another thing I realized, I’ve always you for years, and until we got on this video call, I had no idea what you looked like. and which is kind of an interesting,[00:47:28] Dave:Well, I’m sorry.It’s by design. I have a face for Panda.[00:47:32] Nathan:Tell me more about, well, I guess two sides, one, has there ever been an interesting interaction? You know, because you’re like, Hey, I’m, I’m Dave and people are like, I wouldn’t have ever recognized you. Or has there been any other benefits and thought behind, you know, why it have an avatar?[00:47:49] Dave:If by interesting you mean horrible? Yes. There’s been many interesting interactions with people. I mean, before, before I had my current, avatar, which is, pretty awesome, actually, a guy named Brian Molko designed it. I had this incredible drawing of a character that looked like me that, had sort of ether net, Machinery and cord going into his head and it was like me, but my head was actually lifted.The top of my head was lifted off and you could see all this machinery and it was an incredible graphic, by this guy named Sam Spratt. Who’s now done, album covers and book covers. He’s like a super talent. If you want to follow somebody fun on Instagram, he’s just incredible. And it was a drawing, even though it looked photo realistic.And I used that for a while and then I would go places and people would be like, you are so much fatter and grayer than I imagined. And so instead of having Sam sort of ruin his artwork, I went back with the more, cartoonish or animated, avatar. So since then I don’t get too much of that, but, that was a good move.Although that’s the best thing about avatars and the internet is that your avatar never ages. It always looks the same. It stays the same weight. My avatar never overeats he exercises right here. Angie really gets along well with others and doesn’t have any kind of social anxiety either. So he’s pretty cool.Yeah, it goes a little downhill with me in person. So[00:49:21] Nathan:Yeah. So is it, that’s something that like, it gives you some distance between you and readers, or it gives you some anonymity that, you know, you don’t want to be recognized in the streets?[00:49:32] Dave:No, no, it’s, it’s, basically just what I described. It’s like, I literally prefer the, the attractiveness of my avatar versus me, but also actually my avatar is really awesome. my logo, so it’s also iconic and scalable. so it looks awesome on t-shirts even people who don’t know what Next Draft is when they see, by son wearing his t-shirt, whatever, it just looks awesome.So that that’s that’s as much of it as anything. I thought your response was going to be mad. You seem perfectly attractive to me. I don’t know what the issue is, but no, you went with, am I doing that for some other reason? Yeah. So, I get this all the time.Cause my wife is a very attractive person also. So when people meet me, they’re always like, whoa, we were once a very famous celebrity came up to me and I said, oh, I’m Gina’s husband. And she was like, wow, you did well. Oh, you know? So I’m like, thanks a lot. That helps. So just gave her a picture of my, my icon and walked away.[00:50:31] Nathan:Then that worked. I’m sure that she has it framed in her office, from now on. it’s just interesting to me. You’re you’re sort of at this intersection between personal brand and, like media brand. And I think the avatar helps push you over into the media brand side. and I don’t have any real commentary on it other than I find it interesting.[00:50:53] Dave:Yeah, no, I think there probably is some of that. I I’ve never really been a fan of using my actual face, or my actual person as a logo. I love the process of designing or working with people to design logos and taglines and all that. But yeah, probably at some point there was a, a goal with Next Draft to make it seem bigger than it is.I know a lot of people that are solo operators. They regularly say we, when they’re talking about their brand to make it seem bigger, I actually think that’s sort of been flipped on its head though. in the last few years where so many people are coming into the space, it’s very clear that what they’re doing is leaving a big brand, leaving a we and going to an eye.And I think it’s actually a selling point in a lot of ways. So, I mean, I, I still get a lot of emails that say, I don’t know if anybody at Next Draft is going to read this email, you know, or if you do, can you get this message to Dave? He’s an asshole or whatever. And it’s like, I’m the only one here, you know, or the other one I always get is when I email back to people that go, oh, I can’t believe you actually emailed back.I didn’t think this would get to anybody. It’s like, you hit reply. And it had my email, like where else would it go? Exactly. You know? But I think actually having people thinking of you as a person, instead of a brand, Is a benefit today. Whereas if you would ask me when I was younger, I probably would have said, make it seem like you have a big company behind you.[00:52:24] Nathan:Yeah. And I think that that indie shift overall, like people are looking for that.[00:52:29] Dave:Yeah,[00:52:29] Nathan:Want to ask about the intersection between your investing and the newsletter. like, are you still actively investing today and doing author.[00:52:38] Dave:Yeah, yeah, no, I, I still invest a ton. I usually follow along with people who are a little more in tune with today’s companies than I am. I don’t really go out there and brand myself as an investor much, but I’ve been really lucky. I have very little intersection actually, if any, with my newsletter and my investing and I definitely want people to. To think of me as a writer first, for sure. Not as an investor who has this hobby, because that’s definitely not in terms of time or passion, the reality. but I’ve been really lucky over the years that, I’ve invested with people or co-invested with them that were cool with me. branding myself as a writer first, but still looking at deals that came through their brands because they were branded as BCS or investors or angels.That’s probably a bigger deal now than when I first started. There were like five angel investors, basically. Nobody really did small, early stage seed deals. you know, I mean, we all knew each other that did it and now there’s like thousands of them. So you really have to be either a really pretty well-known entrepreneur or you have to. Sort of attach yourself to our organization or two who are really branding themselves well, getting out there and building a stable of companies,[00:53:58] Nathan:Yeah.[00:53:59] Dave:It’s pretty different, more, much more has changed about that than the newsletter game, actually, which is pretty much the same as it was the day I started actually.[00:54:07] Nathan:Are there a few of those I’m curious who are a few of those, people that you would tag along with, you know, when they’re investing where like, oh, this person puts money into something I’d like to be right there with them.[00:54:19] Dave:I mean, I have some people that are like entrepreneurs and former entrepreneurs that do it, and if they like it I’ll do it. but generally I co-invest with, at any given time, a different group of people, used to be a larger group. When I first started out, my whole investing career, I’ve co-invested with this guy named Bob zip who’s much smarter and much wiser than I am about all things business and.Startup world. So that was really great. And he used to work at a company called venture law group in the first boom, and they represented Google, Hotmail. eGroups all the big, huge, early internet companies, and so he really knew the space well. And when he became, I used to get deals from him.That’s how you used to get deals actually was by a couple of law firms that focused on startups. I’ve been co-investing with him all along and he’s been generous enough to, he left the law firm a long, long time ago and became an investor primarily. And he had a fund and was well-known guy and well-respected guy.So I got to sit in when he would hear pitches. and we sort of, we weren’t investing together out of the same fund, but we would sort of make our decisions together. And we still do that a lot. these days, I almost always follow along with a guy named run-on barn Cohen and a really good friend of mine.He was for many years at WordPress, basically, most of the things that make money at WordPress, he did. and now he’s a investor at a VC called resolute. If anybody’s looking for a good VC, he’s like incredible, like Bob zip much, much smarter than I am about this stuff. Unbelievably ethical, great business sense.Great technical sense. so I mostly just follow him. So if he does something that’s usually good enough for me. And if I see something that I think it’s good, I’ll pass it along to him, but it’s mostly that, but I’ve been really fortunate. I can’t express that enough, that I’ve been able to invest in companies without having to spend all of my time, branding myself as an investor.That’s just been unbelievably lucky. So, I’ve been able to focus a ton of my energy on my six.[00:56:31] Nathan:That’s right. I’m writing a newsletter about the news. I guess, as you’re looking to grow and continue on, right? Like the next phase of readers and, and all of that, since we can just say directly that we’re all narcissists and we do this for the attention. what’s what’s sort of that next thing that you’re looking for, it’s going from 140,000 subscribers to say 200,000 and beyond.[00:56:54] Dave:Yeah, well, I’m, I’m hoping that, I’m not just trying to sell my book here. I’m hoping that the book and the newsletter will sort of have, a coexistence with them because the new the book is really an extension of the brand and the brand is that icon to Next Draft. So I’m hoping that the tricky part about writing about marketing a newsletter, like we discussed earlier, there’s not really a natural virality to them.So. You Have this piecemeal growth from people telling each other or their friends or forwarding it to somebody or maybe occasionally tweeting or sharing a Facebook link. Oh, you should check this out. But it’s all sort of small little blips. If you get a news story or a big blog story about it, or another newsletter recommending you, that’s probably the fastest way people grow these days is by, co-sponsoring each other’s newsletters or co-promoting them.Those big hits are more rare and they usually require like, I’ve had a ton of stories written about Next Draft, but most of them a long time ago, because it’s basically a similar product to what it was when they wrote about it the first time. So they’re like, Hey, I’d love to write about it, but what’s the hook.What’s the new thing, you know? so I’m hoping that the book provides that emphasis. It’s like, we’re doing now a ton of people who may by either been on a podcast in the past, or they’ve wanted to do a podcast with me say, okay, now’s a great time. I’d probably want to move your book and, we can set something up.So it’s sort of as an impetus. So I’m hoping that that will be the next big newsletter thing that most, most people who write about the book will also write about the newsletter and the two things can sort of grow together.[00:58:35] Nathan:I think that’s spot on.[00:58:36] Dave:That’s in terms of, you know, marketing and promotion, otherwise, I do want to try, one of these referral programs because people definitely do like products.And, I am lucky that my icon looks really good on shirts so that people actually really want them. And I have a great designer named Brian Bell who makes all of my shirts.[00:58:58] Nathan:There’s something like when creators thinking about products, often if you spread yourself too thin, you’re like into the newsletter, the book, the podcast, and like the 14 other things that you could make all at once you sort of hinder the growth of each thing, but then if you really build one of them up to a significant level, then at that point it can start to stall out and by shifting to another medium or have it like launching another product in this case, the newsletter to a book, then that book can have a bunch more momentum that feeds back into it.And so there’s just sort of this interesting balance of like, no, When to like, keep pushing on the thing that you have versus when to add the next thing that like, then they feed off of each other and go from there. So I think you’re doing it with good timing.[00:59:45] Dave:Hopefully it’ll work. All that kind of stuff is the tricky part of doing this stuff. Especially stuff like podcasts and newsletters that are—it’s really a ton of word of mouth, unless you get lucky and get some press, and word of mouth is just slow.There’s some point where you’re going to hit a tipping point where you’re going to go from five or 10,000 to like 50,000 much quicker, more quickly because instead of three people going home and saying, “Hey, did you ever hear of this newsletter?” there’s like 30 people going home and saying that. But, even with that they hit a plateau, and then you figure out what’s the next thing. That’s why doing something you’re into is so important.And I don’t think it’s bad to try those other mediums or stretch yourself out, because you never know you might’ve been writing a newsletter three years, and then you do a podcast and it catches on. For some reason, you’re like awesome. Less typing, more talking, let’s go. So, but it’s tricky. I wish I was better and had better advice for people on promotion and marketing.I’m not awesome at it, and it’s not in my nature. So, begging for favors or telling people, even in my own newsletter, to buy my own book is very painful for me. I’m very sensitive to criticism about it. So, if people just all bought it and then made everybody else buy it, that would be a huge relief for me.[01:01:13] Nathan:That would be great. Well, along those lines, where should people go to subscribe to the newsletter, and then follow you on your preferred channel, and then ultimately buy the book?[01:01:24] Dave:I don’t want like two or 300,000 people taking my site down. So let’s go with if your last name starts between A and M you can start by going to NextDraft.com and sign up for the newsletter there. Or, you can also just go to the App Store and search for Next Draft. If you’re N through Z, you can start with the book, and that’s at: PleaseScream.com.It has links to all the various audio, and Kindle, and hardcover versions.[01:01:50] Nathan:That’s good. I liked how you split the traffic, that way there’s no hug of death, and we’ll do well there.[01:01:57] Dave:I don’t want to get fireballed.[01:01:58] Nathan:That’s right.Dave. Thanks for coming on. This was really fun.[01:02:01] Dave:Yeah, thanks a lot for having me.

Jessica DeFino is a freelance beauty journalist living in Los Angeles, California. For the past seven years Jessica has been writing, researching, editing, and publishing about the beauty and wellness industry. Her work has appeared in Vogue, The Cut, Fashionista.com, Cosmopolitan, Marie Claire, Business Insider, SELF, HelloGiggles, Harper's Bazaar, and more.Before starting her career as a freelance journalist, Jessica worked as a beauty writer for The Zoe Report. She was Director of Communications at Fame and Partners, and worked as a ghostwriter for Khloé Kardashian and Kendall Jenner.Jessica earned her bachelor’s degree in Music/Business Songwriting from the Berklee College of Music. Jessica’s music degree brings a unique perspective to her writing. It infuses each piece with lyrical qualities of storytelling, flow, and connection to her audience.Jessica also publishes a bi-monthly beauty newsletter called The Unpublishable, where she shares “What the beauty industry won’t tell you — from a reporter on a mission to reform it.”In this episode, you’ll learn about: Making lasting connections with your audience Why understanding music and rhythm makes your writing better Capturing and keeping your readers’ attention right from the outset The dangers of cross-posting your content across social media Links & Resources Vogue Magazine Allure Harper's Bazaar Ursula K. Le Guin RhymeZone Ali Abdaal Jessica DeFino’s Links Follow Jessica on Twitter The Unpublishable Jessica’s Instagram Episode Transcript[00:00:00] Jessica:I started writing as a songwriter. The musicality of something is very important to me. So I’ll read my own stuff out loud sometimes. I feel when people can read something and there’s a clear flow and rhythm to it, and the words melt into each other sound nice next to each other, it locks them into the content early on. You want to keep reading because if you stop reading it’s like you’re breaking this rhythm that you’ve started.[00:00:34] Nathan:In this episode I talk to Jessica DeFino. She’s a journalist covering the beauty industry, but she tends to take an approach that’s not as popular with sponsors and publishers, because she’s anti a lot of their products and a lot of the nonsense that is put into the products and the marketing behind it.She’s taking a critical angle and she’s well loved by her readers because of it, but maybe not so loved by the big brands. We talk about how that came about. We talk about her writing style, her approach of using her background in song writing and going to school for songwriting to have a better, more interesting writing style.She gives some tips along that angle, talking about how she launched a newsletter last year and growing that to 9,000 subscribers. How that is a backbone for the rest of her work she does in journalism.It’s a great conversation. So, let’s dive in.Jessica, welcome to the show.[00:01:28] Jessica:Thank you so much for having me.[00:01:29] Nathan:We’ll jump around a whole bunch, but I want to start on the launching of your newsletter. What was the moment when you started to think, okay, I want to actually run a newsletter and start to control my own audience?[00:01:44] Jessica:I had been toying with the idea for a while, and then I think it was, April, 2020, right after the pandemic, where I had gotten into a situation where—I’m a freelance reporter—I had four freelance stories out when March happened, and Coronavirus lockdowns happened and everything was up in the air.The company severed ties with all of their freelancers and basically gave these four unpublished stories back to me, and gave me a kill fee. So it was like I had reported out these whole stories. I had spent months on them, and now I had nowhere to put them, and I gave it about a month of pitching it out to other alums.There weren’t any takers because media was in such a precarious position at the time. Finally I was like, maybe this is the opportunity I’ve been waiting for to launch a newsletter. and I decided to call it The Unpublishable because I couldn’t get anyone to publish this. And yeah, it’s been going, almost like every other week.[00:02:50] Nathan:Nice. Yeah. It’s interesting how these unfortunate moments result in something that’s like, okay, this is actually either a good thing now, or hopefully going to be a good thing soon, but it starts with difficult times.[00:03:05] Jessica:Yeah, exactly. I wanted these pieces to be big. They were stories that I thought were important to tell, and I really wanted them to be in a major outlet. Sometimes with media, you can’t sit on things for very long. It was like, I maybe have two more weeks before they stopped becoming relevant.[00:03:23] Nathan:Yeah. So for context, for anyone listening, what were some of those stories as an example?[00:03:27] Jessica:The first story I published with a piece called “Where are All the Brown Hands?” It was a look into the overwhelming whiteness of the top nailcare companies in beauty. If you would look at their Instagrams or if you would look at their websites, everything was modeled on white hands.As a beauty reporter, when I have to source images for the stories, I don’t want to just be showing white hands. If I’m writing about nail trends or whatever, and it would take me hours every week to comb through places and try to find the trend I was speaking to on a person of color. At one point, I was like, why is this happening and how come it’s so hard?This should not be hard. So, I wanted to do an investigation into it, and just like that the whole process had already taken six months. I was like, you don’t know what’s going to happen in this story. It might be scooped. It might be written by somebody else. It might be irrelevant in another month or so.So, I really wanted to get that out there, and that started it.[00:04:31] Nathan:When you publish a story like that, and you’re used to publishing for a major beauty publication, but you’re publishing it for yourself. What did that look like? What was the process of saying, I have this story that I’ve worked on for a long time, and I have a brand new newsletter and all at once.How did you bring that to life and pull the audience together?[00:04:52] Jessica:Well, luckily at that point I had a mask, a little bit of a social media following just from my work on work, like major publications. Like I had been writing for Vogue and allure. Harper’s bizarre. And I had been pretty diligent about building up a social media audience. So I had a pretty sizable, amount of readers just from Instagram.And a couple of years prior, I had like tried starting my own beauty content platform, but I never really had the time to dedicate to it. But I had a small email list from that, from when I was still doing it. So I kind of like funneled all of that together under this new umbrella of this is going to be like my personal reporting newsletter and I kind of got the word out on Instagram.So it ended up reaching like a surprisingly large audience for something that was like a first-time newsletter.[00:05:44] Nathan:Yeah. So if you don’t mind sharing how many subscribers were like to that first article?[00:05:49] Jessica:I think that first article probably went out to like 1500 subscribers[00:05:53] Nathan:Okay. Yeah, but that’s you’re right. That, that is a surprisingly of like, here’s the first thing that we’re doing.And I guess it goes to show from right. Spending a whole career being known and, and building it in this space. And then, you know, you’re not starting from scratch when you funnel entity.[00:06:10] Jessica:Yeah, it, it had always been important to me to, not as important, but it was something I thought about to collect email addresses and to get social media followers, because my goal had always been to write a book. And I know that when publishers are looking at whether to buy a book from you, it matters what kind of audience you have and how many people you have on an email list.So even though I wasn’t sending things out prior to finally launching the newsletter, Collecting emails here and there. Just, just to have for the, for the book pitch one day.[00:06:42] Nathan:Yes. That’s something that I’ve always heard is, you know, from agents and friends who are authors and all of that, as they talked about the, the email as being the thing that the publisher is looking for, they’re like, Yeah, that sounds good. First question.[00:06:57] Jessica:Yeah.[00:06:57] Nathan:I mean, they use it as a proxy for how many copies can you sell?[00:07:01] Jessica:Exactly. Yeah. When I was pitching out my book, it was all about, Instagram. I, this was probably like two years ago now. and I couldn’t get an agent to talk to me until I had 10,000 Instagram followers. So that’s like, all I cared about for maybe a year, I was like, I don’t care. I’m not going to put effort into anything else.I just need these Instagram followers.[00:07:23] Nathan:Yeah. So you have 35,000 followers on Instagram now. what were the things that worked for you as far as growing that, that audience on it?[00:07:32] Jessica:Honestly, in the beginning, when I was like, I need to get to 10,000 followers, I was a little scammy about it. I did a lot of the like follow unfollow. So I followed a ton of people who were following accounts that were similar to mine.And kind of, and what you do with that is like, they see that you followed them, they check out your page.Hopefully they follow you back. If they don’t follow you back, you can like unfollow that person to keep your ratio looking good.[00:08:00] Nathan:So is that like going through and following like 50 people a day kind of thing or hundreds[00:08:05] Jessica:Yeah. I mean probably 50 to 200 people. Like I would spend probably an hour or two hours a day just doing. Stupid stuff like that, but I didn’t really care about, but I was like, I’ll do anything to get a book deal. If it’s following 200 people a day, that doesn’t bother me. And if at the end of the day, they’re looking at my profile and saying, Hey, this is somebody whose content I care about.I’m going to follow them. It doesn’t feel like bad or wrong to me. So I just did a lot of that[00:08:34] Nathan:Yeah, it’s a very small way, like small and non-intrusive way to be like, Hey. Do you want to pay? Like, you’re just sort of raising your hand and people either go like no, or they go, oh yeah, I’ll look at that for a second.What’s interesting is I think that a lot of creators started in that way, but probably now when they tell their story, they’re like, yeah. You know, I just, I just put out good content and then the content itself. And before you know it, I was, you know, internet famous, you know,[00:09:01] Jessica:I think that worked, it worked like 10 years ago, maybe even five years ago, but right now there’s just so much content out there on every platform. And I don’t think it’s fair to say that if you have great content, you will be successful on that alone. Like, I think you need more than that today.[00:09:18] Nathan:Yeah. So, so the following, people in the space, which we’d recommend, you know, regardless, what are some of the other things, on that quest to 10, that will.[00:09:27] Jessica:Yeah, I was falling up a storm.I was liking a ton of stuff cause that’s kind of the same strategy. Like sometimes Instagram too will phrase your account. If you like too many things or you. follow too many people. So I was getting into that. I did a ton of hashtagging at the time. luckily the, the area that I write to to beauty has like a very big and dedicated community on Instagram.So there are a ton of like beauty community hashtags out there that I was following and getting involved in and commenting and just really making my presence known in this community while at the same time posting my own content. That I thought had a very different point of view that would be intriguing to people.So once they saw that I was engaged, they were like, who is this person? And there was, you know, a lot of content there for them to, to delve into.[00:10:18] Nathan:Yeah, that’s good. In the last, episode of this show, I had a YouTuber on his name’s Ali doll and he’s got, you know, he’s built up to 2 million subscribers on YouTube, but he talked about that like back catalog that you have of when someone comes across your work for the first time, like seeing the back catalog and seeing it have a unique point of view.And I feel like. That would be the experience, you know, when you pop up in some little way. Okay. Another, you know, beauty, Instagram account, and then you come in like, oh, this is actually different. Has a unique point of view. So, I’d love for you to share. I don’t know what the, the short version of like the different perspective that you’re bringing to the beauty industry and what someone would notice when they come to your Instagram or your, newsletter.And they’re like, this is different. This is a, you know,[00:11:08] Jessica:Yeah.[00:11:09] Nathan:Challenging.[00:11:10] Jessica:I think the easiest way to put it that most beauty content out there is very fluffy. and very positive and very product heavy. and my stance is very beauty industry critical. and I, I say that I’m pro skin anti product. So I’m much more interested in how beauty applies to like your actual skin and your actual body and like the human itself, rather than this external product, you can apply some very focused on the science of how human beings work rather than the science of like a skincare and.[00:11:44] Nathan:Right. Okay. Is there an example that comes to mind of something where you’re like, do this? Not that.[00:11:50] Jessica:Yeah. I mean, probably the biggest example is just, I mostly tell people to stop using skincare, you know, period. End of story. Just, you don’t have to, our skin does all of that for us. You know, humans have survived millennia without pre bottled products, and there’s no reason why. In the past 30 years, our skin has suddenly evolved to need a 10 step routine.It doesn’t so, yeah, I just tell people, stop using it. And they’re shocked at the results all the time.[00:12:20] Nathan:I like that. I could see a conflict in. Message and business model in the industry. and your interaction in this. there’s a lot of money in the industry of obviously selling, I mean, any product, but especially a product that you need to buy every month or every three months or something like that.Like that’s a very good business. So have you had any, any conflict of publications not wanting to pick up your stories or any of those things as the publication is. You tell your people to not buy our sponsor’s products, you know, or something like that.[00:12:55] Jessica:Oh yeah. I mean, there’s been a ton of pushback and depending on what platform I’m writing for, I. See my work being edited in a certain way or softened in a certain way or a brand name being taken out. I’ve had articles be published and then the platform takes them down almost immediately because an advertiser has complained.I’ve had legal action threatened against me while I’m reporting for a story just for asking questions. yeah. Yeah. It’s that kind of stuff happens all the time because in beauty journalism, there is a huge. Conflict between what you’re supposed to be writing about and who’s footing the bill for that content, which is products and advertisers.And I think in the beauty industry in particular, there’s this extreme lack of objectivity where, you know, editors and journalists and influencers are all gifted product or taken on press trips. And. And given money to review products in a way that in any other industry, you wouldn’t be able to call that journalism.You know, there’s always gotta be some sort of separation there. Like a typical journalist is not allowed to accept gifts in the beauty industry. It’s the complete opposite. It’s like, well, how can you write about our product if we don’t gift it to you? So it’s, it’s a very weird space that is very reliant on gifts and money and advertising.[00:14:18] Nathan:So how has that changed as well as you’ve launched your own newsletter? I imagine you’re still doing plenty of freelance writing. Is that.[00:14:27] Jessica:Yeah. Yeah. I’m still, my, my thing is, is I try if I have a story I want to tell, I obviously want to tell it to the biggest platform possible. And then if I can’t get the story placed somewhere else, I will, I will tackle it for the news.[00:14:43] Nathan:Okay. So yeah. How has like, has the news that are helped? Like, for example, you’re trying to get us started placed and they’re like, sure, we’ll place it. But could we do this version of it instead? And, and you know, maybe you’re saying that like, no that’s okay. Whereas before the paycheck might’ve mattered more or how’s That. relationship?[00:15:01] Jessica:Yeah, that’s pretty much spot on. I, I didn’t really push back too much before, but now that I have. platform that like actually brings in, okay. Money for me. It’s not like if I say no, I don’t want that story published this way. It’s really not like I’m losing out on a paycheck anymore because I will make that up from my own subscribers.So, I think since I’ve launched the newsletter, there have been two instances of that where I’ve written a story for a platform have been uncomfortable with the edits and actually. And was like, no, I don’t, I don’t want to publish it this way. And that feels really good to have a little bit more control over, over what I want to say and the information I want to put out there.[00:15:45] Nathan:Yeah. I mean, you have even more, I mean, you, you always had agency, right. But now it’s like, you have an alternative instead of like, I’ll keep pitching it to someone else who might have the same objections or, or that kind of thing. On the business side what’s well, actually, maybe if we dive into the newsletter today, right?So that we talked about where I was at a year ago when we launched to, I just said, we, when you launched, I had nothing to do with my launch. There’s no Royal we in that are taking credit later. when you launched, you know, a year and a half ago, there was at 1500 subscribers. where’s it at today,[00:16:24] Jessica:I’m at 9,000 subscribers now.[00:16:26] Nathan:Right?[00:16:28] Jessica:But, I mean, I have a model where some of it is free and some of it is paid, so there are like different cohorts within the subscriber-based too. But like, I’m, I’m pretty happy with how it’s grown on the free side so far.[00:16:41] Nathan:Yeah. And so on the paid side, you’re charging $7 a month, or 77 a year. What was the thinking on the pricing there? Was that something that you like agonized over a lot or was that a, like, we’ll just go with something and see how it works.[00:16:54] Jessica:Yeah, I didn’t agonize over it too much. I started out at $5 a month and, after I got maybe my first hundred or 200 paid subscribers and I felt really good about like, wow, that feels like a lot. That’s like a good chunk of change I didn’t have before. And then when I was looking into the fees that were taken from like Stripe processing, from sub staff, I was taking home like closer to $3 per subscriber.And I was like for the time and attention that I want to give this project, I’m just not going to be making it. At $5 a month until I hit a certain number of paid subscribers. so I decided to bump it up to seven, just to sort of motivate myself to put the time and attention into it that I wanted to give it because if I wasn’t going to be bringing in like, actually $5 to me, it didn’t feel worth it.So by pricing it at seven, I get more like $5, which felt like a, okay, I’m happy with that number. now that I do have more paid subscribers, I am toying with the idea of, of lowering it because I feel like I feel like from, at least from my perspective, when I am subscribing to a newsletter,I subscribe to a ton of them.I’m much more interested to click. I’m much more likely to click pay and subscribe if it’s $5.And if it’s like six or seven or eight,[00:18:21] Nathan:You think about[00:18:22] Jessica:Eh, that’s kind of a lot. Do I care enough about this content to pay that much? But personally for me, $5 is like a whatever I’ll I’ll subscribe kind of thing. So I, I think I’m getting closer to the point where I feel like I have enough of a base that I can do that and hopefully reach more people.[00:18:42] Nathan:Right. Okay. I have so many questions here, but diving into the psychology side of when you’re deciding to subscribe to something, right? Cause everyone listening is Ryan newsletter and asking these same questions. Like, should it be $5? Should it be $20? Should it be free? Shouldn’t be $2. You know, like any of these things.And then they’re analyzing their own buying habits. And they’re like, but what if it’s a business versus a fitness versus, you know, any of these, like what category I’m in and what are those other things that you notice beyond price? When you as a newsletter consumer, I go to like instant subscribe versus like, well, think about this.How many articles have I enjoyed from the recent layer? Like that, tips it over to the other side.[00:19:25] Jessica:Right. Oh, I don’t know that there are that, like my personal revelations will be. relevant to people. I personally, just because I run a newsletter, I love to support. So if it’s anything that I’m like vaguely interested in and it’s like $5 a month or less, I don’t know why $5 is my cutoff, but also subscribe.And I’ll just see what it’s like for a couple of months. And if I don’t like it, Whatever I can always unsubscribe, but I just really love the idea of putting that abundance out there into the universe and just being like, I’m a little bit interested in this and I want to support this creator because I know what a, like a hustle it is.I’m sure the average, like newsletter consumer doesn’t really doesn’t really think that way. but for me, I don’t know. I love a good headline if it’s like a good quippy, funny headline, like I want to be reading. fun, critical content. There’s a lot of like heavy, critical content out there. and I love something that’s like fun and critical, so that’ll get my[00:20:27] Nathan:Yeah. There are things wrong with the world and we could get depressed about them, but that doesn’t[00:20:32] Jessica:Yeah,[00:20:34] Nathan:About fixing the things that are wrong with the world,[00:20:36] Jessica:yeah, exactly. Like turn it into a little bit of a, like the state of the world I feel is so bizarre.[00:20:43] Nathan:Right.[00:20:44] Jessica:Just so wild that we have set up the world the way we’ve set it up. Like everything that, that exists is just something that like some guy made up one day and we were like, okay, we’re going to go along with it.And I feel like there is a lot of humor in that. so yeah, I, I love looking at the depressing state of the world for like a bit of a jokey lens. So if I find anything like that, I’m like immediate.[00:21:09] Nathan:Yeah, that makes sense. And I think that’s where for anyone writing their content, like having that voice really matters. So it’s not just, you know, this is what you’re teaching or this is, the educational side. Or present the entertaining side. It’s like, okay. But how can you, how are you gonna make me feel as I read and consume this.[00:21:29] Jessica:That’s a great way to think about it. I think the difference, when I’m consuming like a newsletter versus the news is I don’t really know. I don’t concern myself with like tone or voice when I’m reading an article from like the New York times or the Washington post. but a newsletter is so much more personal.It’s like you’re getting into people’s personal inbox, it’s more of a one-on-one relationship. and I think it’s a great opportunity to play with your voice in a way that you really sometimes can not when you’re writing for a media plan.[00:22:04] Nathan:Yeah. So what are the things that you’ve done to practice that obviously you’ve had a whole career as a writer. And so, you know, as you’ve found your voice and the things that you play with, are there yeah. Little exercises or things that you play with or try on, or anything like that? Any, any tips for someone who’s also looking to like craft their own way?[00:22:26] Jessica:It’s as much of a tip, but I started writing as a songwriter. I went to school for songwriting. So I feel like a lot of my writing takes that into account. Like that’s the musicality of something is very important to me. So I’ll like read my own stuff out loud. Sometimes like flow of a sentence is very important to me, the rhythm of a sentence, the like intonation, the, Continence and assonance and all of that alliteration, I, I feel like when people can read something and there’s a clear flow and rhythm to it, and the words like melt into each other sound nice next to each other.I personally feel like it locks them into the content early on. Like you want to keep reading because if you stop reading, it’s like you’re breaking this rhythm that you’ve started. So, yeah, I would say rhythm is very important to me and reading things out loud helps me make sure that what I’ve written is what I’d like envisioned and felt[00:23:35] Nathan:Yeah.[00:23:36] Jessica:Mind and my heart when I was conceptualizing the thing.[00:23:39] Nathan:Yeah, reading out loud is a really good tip because there’s so many things where I’ll find myself starting to read what I wrote and then like finishing it in a much more like in my head in a much more conversational way, and then realizing the sentences or the following sentences that I had. We’re not conversational.They were like stilted. The version that I wanted to auto finish in my head is like, oh, that’s better. Let’s let’s say that instead.[00:24:05] Jessica:I love that. And I think, I think newsletter subscribers are like ready for more. Conversational writing. Like I don’t, I think you can be like professional and say something that has weight and has merit and has value and still be kind of, you know, casual about it.[00:24:23] Nathan:Yeah.[00:24:23] Jessica:As a strategy to connect with people.[00:24:26] Nathan:Is there a poster or a piece that you’ve written that you felt like. Maybe you struggled to find that balance of like, it was a, maybe a weighty piece or something like that. And you’re like, oh, maybe this one I shouldn’t be playful with or, you know, finding[00:24:41] Jessica:Yeah, there are definitely times when I take a break from the jokey conversationality I think the last big piece that I wrote, was about, anti-Asian racism when like all the news came out that like anti-Asian hate crimes were at an all time high. there’s a lot of the beauty industry tends to take a lot of its concepts from Eastern culture, from Asian cultures.So, there was a lot to say there about racism within the beauty industry that, you know, happens in ways that you may not even realize. So for a piece like that, I think there were some moments of, of humor within it, like a dark humor within it, but for the most part, for, for things like that, I take that very seriously.I think my readers take that very seriously and I. It’s less conversational then, because it’s like, no, I have something that’s like very important and clear that I want to get through to you. And I don’t want it to be muddled with any sort of, uh jokingness.[00:25:46] Nathan:Yeah, that makes sense. So let’s say you were a writing coach, coaching someone,Ryan newsletter, that sort of thing. You don’t have to become a writing coach after this. Just.[00:25:59] Jessica:Thank God.[00:26:00] Nathan:But like, you know, you have a friend, maybe they’re writing the newsletter, they’ve got a couple of thousand subscribers they’re getting going in.And they’re saying like, you know, they, they hear what you’re talking about of the, the musicality and the, the flow of, of writing. And they’re like, okay. Short of going to songwriting school, like, what’s the, what, you know, is there, a book or another thing that you would recommend of where to start to, to sort of dive into the flow of what you write?[00:26:29] Jessica:There is a great essay, by Ursula K Le, is that how you say her last name?[00:26:37] Nathan:I’m not sure.[00:26:37] Jessica:Read it and I’ve never said it out loud before.[00:26:41] Nathan:Yep. I have so many things like that in my life where I’m like, I don’t know how to pronounce this word.[00:26:46] Jessica:It’s so embarrassing writing about skincare, because there are these huge, like long skincare ingredients that I write all the time. I can spell them for you off the top of my head, but then I tried to like say them out loud on a podcast, for example. And I’m like, I don’t know how to say this at all. I’m looking for this, this essay it’s from her book.No, no time to spare[00:27:10] Nathan:Okay.[00:27:10] Jessica:And there’s this. And she writes a lot about right. but she has this beautiful essay about rhythm, and how it’s different in poetry and how it’s different in pros and how to kind of like sort out the rhythm of your piece. and I would say that was hugely helpful to me when I, when I first read it.So I would recommend doing that and. Yeah, I don’t know. I use things like, I mean, I, I use it the sores all the time, but I use rhyme zone a lot for like fun phrasing and plays on words. It’s just rhyme zone.com and you type in the word that you’re you’re playing with. And it’ll kind of like, you know,[00:27:50] Nathan:Oh, interesting. Yeah.That’s exactly the kind of, kind of that’s good. Yeah. A lot of people, you know, they come to newsletters from kind of two different sides, either from the journalist, professional writer side or the, you know, hobbyist, maybe even, I never thought I’d be a writer, but I have this skill or something to teach or behind the scenes in this industry.And like writing maybe as a slog or a chore. And so it was always interesting when these two worlds meet and either, you know, one group might be really good at marketing because they knew they came from that world and another group.[00:28:27] Jessica:Yeah.[00:28:27] Nathan:Really good at writing and they each hate the other’s job, but[00:28:31] Jessica:Yeah,[00:28:31] Nathan:Like they pick the job.That’s the intersection of both of those worlds.[00:28:35] Jessica:Yeah, no, you’re so right. I think there is this like sort of misconception in the journalism and reporting space that any reporter who is on sub stack has decided to go in all in on the newsletter. Because there have been some very high profile journalists who are no longer writing for like the times or the posts and they’re just doing their newsletter.But I think for the large majority of, of reporters and journalists who have, who have started newsletters as well, it’s like a both and kind of thing.[00:29:06] Nathan:Yeah.[00:29:06] Jessica:Sill freelancing and we have this, this sort of personal platform.[00:29:11] Nathan:Yeah. So how do you think about your career developing over the next couple of years? Is it, is there a specific milestone in mind, where you’re trying to grow the newsletter to, to do that full-time or is it always trying to place a piece to the biggest possible audience?What’s that like?[00:29:29] Jessica:Yeah, I would say my goal, like I very much, this is kind of earnest and nerdy, but like, I very much want to change the beauty industry. I see so much that is wrong with it and I see how it like emotionally impacts people. in terms of anxiety, depression, mental disorders, eating disorders, like there’s a lot of heavy stuff that comes out of the beauty industry.And I like, I’m very passionate about actually measurably changing it. So for me, the number one thing is always, I want to reach the largest audience possible with an unadulterated message. So if I can do that in a place like the New York times, of course, I’d rather place it there than my own news. if I can do that through a book, of course, I’d rather write it in a book then in my own newsletter.So the newsletter has been sort of like a nice foundation for me to have and a nice fallback for me to have. And I, I truly love fostering it as its own little separate entity, but I would, I would say I almost try harder to place things elsewhere because I wantAs many people as possible to be able to, to read the things that I’m writing. the newsletter I’m I am writing my first book right now, and it’s definitely been hard to juggle book writing with like reporting for other platforms and deadlines. So I will say like juggling a book and my own personal newsletter has been much easier than trying to juggle a book and reporting. So I think, I think there will be times in my writing career while I’ll lean a little bit more heavily on the newsletter.And times where I’ll lighten up on the newsletter. I’m always seeing it as sort of like a supplemental tool to my like greater mission.[00:31:13] Nathan:I think, I don’t know what publication they were writing for. but someone was telling me about, was that in each of these publications, they’re watching the view counts, you know, for every story. And they had gotten the newsletter. I think they were maybe at 20, 25,000 subscribers. And they would, when they placed a piece with a fairly major publication, they would email it out.And they, it was enough direct traffic to that individual piece that they could get it to move on. Some of these internally watched leaderboards and stuff like that. And so editors were paying attention to that of like, they didn’t necessarily know like making things up that, you know, Jessica was the one who drove a bunch of traffic to this, but they’re just like, wow, Jessica’s stories are consistently resonating.And so they were wanting to pick up more pieces in that. and so I was always wondering about that, of how you can, it’s not gaming an algorithm or anything like that.[00:32:08] Jessica:Hmm.[00:32:08] Nathan:Just saying like, look, here’s my story. And I bring an audiences.[00:32:12] Jessica:Oh, I love that. I might try to do that. I always do. Like I do these little roundups every other week for my paid subscribers.And if I have something that comes out, I’ll always put, drop the link in there, but I’ve never done like a strategized push like[00:32:28] Nathan:Right.[00:32:29] Jessica:Be interesting to experiment for sure.[00:32:31] Nathan:Well, cause it’s like, if someone is following you that they’re following you for. Your content and your ideas and your perspective. And they probably don’t really care if it’s, you know, in your sub stack, you know, on your Instagram or, you know,[00:32:48] Jessica:Right.[00:32:48] Nathan:Major publication, there’s like, look, I want to read your, your content.And you’re like, oh, today’s article is[00:32:54] Jessica:Yeah.[00:32:55] Nathan:Here on Vogue. Or, you know,[00:32:57] Jessica:Kind of nice to hear, because I think that’s something that I do worry about pretty often with my newsletter is I feel like a ton of my newsletter readership has come from social media. And so I’m like very conscious of cross posting. Like I don’t, I don’t want someone to get my newsletter and say, I already saw this on your Instagram, so I don’t need to subscribe.I don’t need another email in my inbox because I’m seeing it on Insta, you know? And I don’t know if that’s like a legitimate concern or how much people see when they subscribe to you on different platforms. but that has been. You know, something that I’m very mindful of, where if it’s like a meme that I’m posting on social media, or just like a one-off Instagram post, I’m probably not going to repeat that content, even if I think it’s good or important on the newsletter. Just because I don’t know, I’m aware of like how precious it is to allow someone into your email inbox, because at least for me, like email is very annoying. The worst part of my day is trying to like go through my inbox and file it away into folders. And I never want my newsletter to be like, oh, I’ve seen this already. I’ve seen something very similar from her already.[00:34:09] Nathan:Right. Yeah. I don’t know that I have a perspective on that. I’m just thinking about it. I don’t have the same concern. but I don’t know that. You know whether I should or not. I think probably my approach would be that if you’ve already seen something, let’s say there’s five or six things in the newsletter and I’ve already seen one of them on Instagram, but I just skipped past that one.[00:34:30] Jessica:Yeah.[00:34:31] Nathan:And so my focus would be on making sure that everything is high quality, more than making sure that everything is, completely a unique[00:34:40] Jessica:Yeah. That’s I mean, that’s encouraging to hear, and I think that that might, change how I approach my like every other week[00:34:49] Nathan:Yeah,[00:34:49] Jessica:Maybe I’ll experiment and I’ll see, I’ll see if people are like, Hey,I saw that.[00:34:54] Nathan:The other thing that I would do is I would ask, one of my favorite things to do is to ask for replies to my newsletter, which has a downside of that you get a whole bunch of emails, but they can often be really fun cause they’re, No, the people who are reading every day and like they’re following your stuff.And, and so they’re usually not pitching you things. They’re just saying, like, here’s the thing that I, and so in that case, just say, Hey, you know, if I share something on Instagram, would you also like it here? Or do you feel like, keep those worlds more separate? Like don’t I want everything to be unique.And then I would just like, say hit reply and let me know.[00:35:34] Jessica:Yeah.[00:35:34] Nathan:And it’s. Yeah, but you know, out of 9,000 subscribers, I’d bet you’d get at least, I dunno, 20, 30, 40 replies or something.[00:35:42] Jessica:Yeah, that’s a good point. Okay. Oh, you’re inspiring me. I have so many ideas now.[00:35:48] Nathan:Perfect. I love it. okay. One thing that I want to know more about is growing that. That newsletter from the pieces that you’re, I assume subscribers are coming from Instagram. And then also from the pieces that you’re publishing,[00:36:04] Jessica:Yeah.[00:36:04] Nathan:Seen like spikes? when it came from an Instagram post that did really well or some other promotion to drive subscribers,[00:36:13] Jessica:I mean, I definitely get new subscribers every time I post about it on Instagram or Instagram stories. So I would say that’s been like a main driver for me, but my two biggest, like surges of subscribers came from, All of the newsletter press that’s been happening lately. Cause you know, like the newsletter revolution is here.So, I got a little write up in New York magazine and then one in the UK Sunday style magazine and both of those were amazing and totally unexpected. I had no idea they were coming. so now I’m like, damn, how do I, how do I facilitate some more press for myself? Because this is where that.[00:36:55] Nathan:Like what would a spike like that look like? Cause that a couple of hundred subscribers, 500 a thousand from one of those[00:37:01] Jessica:I would say from New York magazine, it was probably close to a thousand. And then from the UK, Sunday times was probably between like 500, 600.[00:37:11] Nathan:Yeah. That that’s substantial.[00:37:14] Jessica:Yeah. It was, it was really exciting. and it definitely goes to show like the power that these publications have. It’s interesting to see that power as applied to like inherently, anti large publication platform, like a personal newsletter, you know?[00:37:35] Nathan:Yeah. So how do you, how do you think about it when it’s like. More press would be nice. You’re like, Hey, this, this is a big boost, you know? I’d 10% lift in total subscribers or something from a single thing. And then knowing what you know about journalism and being in the space, like, is that something that you craft a strategy around and say, okay, I’m going to intentionally pursue, placements in these publication.[00:38:02] Jessica:No, in terms of just the newsletter, I, I don’t think I’ll ever like strategize and try to do that. I think, I mean, the, the reason that I got those two placements is just because I. In the beauty space, my newsletter does offer something that’s really different that you’re not getting anywhere else. and so it becomes inherently interesting to write about or call out because this is the only place you can get that kind of thing if that’s what you’re looking for.So I think it’s just more of like striving to figure out, like, how can I create more, very original content that actually. Gives value to the reader in a way that’s going to create that kind of buzz. I don’t want to like manufacture the buzz so much as I want. Like my condoms would be good enough for people to actually talk about it.But that being said, when my book comes out eventually like, hell yes, I plan to like strategize and try to get the shit written about me everywhere, which will hopefully we get to the newsletter as well. But yeah, I feel like I’m going to save all of that, like smarmy, you know, networking for book launch.[00:39:14] Nathan:Yeah, that makes sense to me. I want to push back on it a little bit, because so much of the success of the book is going to be dependent on a lot on a lot of things, but a big factor is going to be the size of your platform. When that book comes out.[00:39:29] Jessica:Yeah.[00:39:29] Nathan:And so if you wait to be self promotional until the book comes out, then like, that’ll get this far, but let’s say you were self promotional in a tasteful way.We’re going to be tasteful about all of this. you know, but along the way, and that 9,000 subscribers turned into 25,000.Right. And it’s that much bigger of a platform to launch from. So I’ll say that with the caveat that I think the same thing.[00:39:51] Jessica:Yeah.[00:39:52] Nathan:We have, I’ve lots of friends who have big platforms and I’m like, oh, I could guest post on them.You know, with them, or like ask, Hey, can I come on your podcast or something like that? And I’m like 90% sure that they would say yes, but then I think, oh, I should save that for when my book comes out. Right.Cause you know, you have that, maybe that, just that one ask.So I think it’s something that a lot of creators struggle with of like when to promote.And so intellectually I’m like promote early enough.[00:40:21] Jessica:Yeah.[00:40:22] Nathan:And then emotionally, what I’m actually doing is I think exactly what you’re doing, but I’ll save that for when I really need it.[00:40:28] Jessica:Yeah, I think for me, there’s also this, this sort of inherent struggle with what I write about and getting press, because I am pretty critical of beauty media coverage. and I’m aware that I have made some enemies in the beauty media space. Like I’m not the most well-liked person, in some of these circles.So I do feel like I only have like a certain amount of rope that I can, use up like a certain amount of leeway in these spaces. and then also I, yeah, I don’t know. I think it’s something I have not sat down to really work out my feelings about. But there is some sort of ethical dilemma there where if I’m critiquing the way a certain platform has covered this beauty trend or whatever it is, I’m critiquing.And then I’m sort of like asking for press at the same time, like ethically, what does that say about me and my participation in these systems?You[00:41:30] Nathan:Right.[00:41:31] Jessica:Which is a big question and not one that I’m going to be able to answer here.[00:41:36] Nathan:Yeah. Are there publications outside of the beauty space that would have less of the, maybe sponsored ties or other, you know, issues[00:41:47] Jessica:Yeah,[00:41:48] Nathan:The main publications might have, but that would find your story.[00:41:52] Jessica:I think so. I think the path that I am trying to follow in beauty coverage right now. the path of sustainable fashion coverage, like I feel like fashion and beauty have been so intertwined in their coverage and they’re, they’re both sort of seen as these like less serious pursuits. They’re both seen as like inherently female interests.And they’ve struggled to be taken seriously, I think. but with like the push towards sustainability content and, you know, the inevitability of climate change, I think. Sustainability and fashion is getting a ton of like serious quality coverage all over the place, even from platforms that wouldn’t normally touch fashion.And I see beauty as being very behind that. Like there are still these huge global issues in the beauty industry and beauty production and just the way that we consume and beauty, that hasn’t been touched. But I see it starting to be touched by these larger, serious. News organizations. And I feel like there’s such an opportunity there.And that those are topics that I’m super passionate about and super interested in. So I’m, I’m trying to carve out a space for myself there to say, look, we’re taking fashion seriously for the impact that it has culturally societaly environmentally. Like we have to start taking beauty justice seriously because it’s just as big of a person.[00:43:17] Nathan:I like, I like that angle on that. That makes a lot of sense. And just seeing trends in a neighboring industry. I think you’re right. I hope that I hope that you’re right in, that plays out in there.[00:43:28] Jessica:Me too.[00:43:29] Nathan:One of the things that I’m curious about is kind of the rise of newsletters in the journalism space.I don’t come from that world. I very much come from the newsletter world. And so seeing, you know, so many people either make the switch full-time, or get to the point where they’re like, Hey, I’ve been writing these pieces everywhere. And like, my byline has just directed people back to Twitter or Instagram or.And now it’s directing people back to my own audience. What are you seeing in like in your friends and colleagues and all of that is, are a lot of people starting newsletters or is there this overwhelming trend of some are starting it, and maybe it’s getting hyped more than is actually happening.[00:44:12] Jessica:Yeah, I think that’s what I’ve noticed. I don’t think as many people within my like, sort of direct. Community of journalists and reporters are starting newsletters. And I think it’s gotten so hyped. Like we’re in such a moment of coverage right now that it almost like, seems like a little lame to start a newsletter now.Cause like everyone’s doing.But the reality of the situation is that everyone is not doing it. And I think there’s still a lot of opportunity and a lot of room to grow and to move into and to create your own kind of thing. like I mentioned, I think there is a big misconception that if you’re starting your newsletter, that means you’re done with journalism and you’re just doing this now.It’s like, no, you can very much do both. And you can do your newsletter once a month. You can do it, you know, once a week you can do it. However, often you have time for it. Like you said you could use it as a tool just to send out your journalism, pursuits to a wider audience. but yeah, I think sort of the hype around newsletters has sort of, created this little, Ooh, I don’t know if I want to do a newsletter too.Cause I might get to see them. Like, I’m just doing what everybody else is doing.[00:45:23] Nathan:Right. Yeah. The, the newsletter hipster trend is sort of passed and it’s gone mainstream. I can’t do it[00:45:31] Jessica:Exactly. I mean, for the record, I don’t believe that that’s true, I think that’s how people are perceiving.[00:45:38] Nathan:Well, it’s so funny to me because, I’ve been doing E you know, email and email newsletters and that kind of thing since I guess, 2013. and you know, very excited. They got into all of that. And I was telling people like, email is amazing and friends that have me, who’ve been doing it since like 2001 were like, yeah, like good job, discovering it.Do you want to go and start? Like what a pat on the back, what are you hoping for here? And watching is, you know, these trends as they come, if you had a friend who, you know, is in the space who comes to you and says like, oh, I’m going to start a new. You know, what are the things, I don’t know, the three or four things that you would tell them right away of here’s what they should watch out for is strategies that they should employ any of those things.[00:46:25] Jessica:I mean, my number one piece of advice that seems really obvious. Isn’t always is just to find your niche. Like I would say hone in on something as specific as you possibly can, within your space so that people have a reason to subscribe. I would say to have, like, especially if you’re doing sub stack or a place where you can view past newsletters, like have a healthy backlog before you actually start soliciting people to sign up so that they can see what your content is like.And then this is a big thing that I think is missing from a lot of the journalism to newsletter side, because like he said, there are people who are coming from marketing and people who have never done marketing in their life. something that I do is that when I’m sending something out to my paid subscribers, I send a shorter version out of it to my free subscribers.Click to continue. And then it brings them to the paid subscriber thing. And I convert between 30 and 50 people every time.And when I sign up for free newsletters, which I sign up for a ton of them, I have never once got in that. I’ve never once gotten an email. That’s like the intro of the article. And then it, you know, sort of leads me into that paid funnel.And I used to work in marketing. I used to work in fashion marketing. That was just like a no, duh of course I would do that sort of thing. but I’ve never seen any other like journalists to newsletter convert, use that very easy tool. so I would say, take advantage of that for sure.[00:48:07] Nathan:Yeah, that’s interesting of the things that in one industry, like you’re right in the marketing industry, everyone’s like, obviously, you know, of course you would do that. And then you get into another space and it is this exciting, new thing. I started in, in design and, like user experience and interface design.And so I brought a lot of design ideas to marketing and then a lot of like direct response marketing ideas into the design world. And it needs to circle. Everyone was like, whoa, this is amazing and new.[00:48:35] Jessica:Yeah,[00:48:36] Nathan:You did it in the original circle, people are just like, obviously there’s nothing novel about it.[00:48:41] Jessica:Exactly. I think people really, underestimate. The skills they learn on the way to get to where they’ve, they’ve gotten to. Like, I never would have thought the job that I hated in fashion marketing would have served me in, in, any way. Cause I sort of wanted to get away from all of that. Like marketing bullshit, lack of a better word, because at least at the company that I was at, it mostly felt like lying and just like squeezing money out of people.I think you can use those tools for good as well, which is what I’m trying to do.[00:49:15] Nathan:Yeah. So a lot of creators struggle with that transition where they feel like either from a past experience or something that they’ve seen where they’re like, oh, I can never ask for money for this or charge for it or, that kind of thing. Or they’re very, very hesitant to sell in any, anything. what would you say to them?Or what’s your journey been like in saying like, no, this is what it costs. This is why you should subscribe.[00:49:40] Jessica:Yeah. I mean, I think it’s important to have, to have a reason, you know, make it very clear that it’s reader funded or user funded. for me, all of my content is very clear that I blame the media advertisement model for so much of the misinformation and bullshit that’s out there in beauty. So me saying that my newsletter and this content is completely user funded, so that I’m loyal to you.The reader rather than an advertiser, is very like, you know, quote unquote on brand for me. And I think people who are interested in my content are more than happy to pay for it. It’s solving a problem that I am pointing out in my reporting, you know? and then I would just say also like allow yourself to be surprised at how much people want to support you.I have been so pleasantly surprised by people who are just, they just liked my content and they’re happy to pay for it. And I think one of the, the biggest, the biggest ways that I’ve seen that happen is that, on substance. They let you do like the page, so you can do monthly or a yearly rate, or you can do something called a founding member, which is just somebody who pays a little bit more to support and they don’t really get any extra benefits at all.And I am shocked at the amount of people who give me 50 more dollars than they need to, just to support, And that’s like, every time I get that email, that’s like someone signed up for the founding member level. It’s heartwarming because it’s like, there are a lot of people out there who want to support great creator, led content.[00:51:23] Nathan:Do you have a percentage or numbers on that? Like I’m curious, every time I see that I’m like how many people select that[00:51:29] Jessica:Yeah.[00:51:29] Nathan:Know from doing multiple prices or packages, that it’s one of the best ways to increase revenue is to just have a higher price option available.[00:51:38] Jessica:Yeah.[00:51:38] Nathan:confirming that, but I want to know any[00:51:40] Jessica:Yeah. I have not like crunched the numbers on anything, but just from, so I sent out a paid newsletter, on Thursday. So between Thursday and today from like my conversions of free[00:51:55] Nathan:Yep.[00:51:56] Jessica:Sign up, I’ve gotten, I think 56, new signups. I would say maybe 10 of them were the yearly membership and maybe five of them were the founding member.[00:52:08] Nathan:Okay. Wow. So half of the year, the ones being the like yeah. I’ll pay you $50 more just to support your work. Even[00:52:17] Jessica:Yeah,[00:52:18] Nathan:Because the yearly membership is supporting your work, but even just[00:52:21] Jessica:Yeah,[00:52:21] Nathan:Above and beyond.[00:52:23] Jessica:Yeah, exactly. I mean, that’s just what, roughly, from what I remember from the email. I’m not like super concerned with, with stats and strategizing right now. I’m just like ecstatic. Every time I get the ding on my phone that says somebody new signed up.[00:52:39] Nathan:Yeah. That’s super fun. So, what are the things that you’re thinking about next for the newsletter? Is it slow, steady, growth, and maintaining that while working on the book? Is there a big milestone that you’re working towards any of those things?[00:52:52] Jessica:There is not a huge milestone, but I think when I first started it, and this is, I think maybe just a personal hangup, but I was very conscious of not bothering people too much, like not being in their inbox constantly. So, it was like one big story a month, and then every other week for paid. Now I’m toying with the idea of doing more, short form content and where weekly content.I’m going to be launching a new feature for paid subscribers that’s gonna be, like an advice column, but more like, how do I navigate the industry? How do I divest from these marketing tactics? How do I like stay smart and know what’s alive and what’s not?So, I’m going to be launching that within the next month.Then, for everybody, I’m going to be launching weekly or even twice a week, just like little, like a little tip newsletter. Because what I do in my newsletter a lot is critique the beauty, and point out what’s wrong with it.People are always like, okay, sure, but how do I apply that to my own life? Like how do I get over the fact that I know it’s marketing, that I don’t need to have big lips to be beautiful, but how do I stop feeling that way?So, it’s going to be more practical tips for, I guess, sort of healing from all of the beauty industry shit that they put us through, but it’s going to be very short, quick hits, like, you know, five sentences, a paragraph tops. So, I’m going to experiment with a couple of different, forms of writing and a couple of different frequencies and see, see what people.[00:54:38] Nathan:Yeah, that sounds good. Well, if anyone wants to go subscribe to that and follow you on Instagram and other things around the web, where should they go?[00:54:46] Jessica:My sub stack is JessicaDefino.substack.com, and you can sign up for The Unpublishable there. And then on Instagram, I’m @JessicaDeFino_.[00:54:56] Nathan:Sounds good. Well, thanks so much for coming on. This has been fun to[00:54:59] Jessica:Yeah.[00:54:59] Nathan:learn about a whole side of the newsletter industry that I’m less familiar with, and just hear your story, and your writing tips, and everything else.[00:55:08] Jessica:Yeah, thank you so much. I feel inspired. I’m going to go send more newsletters.[00:55:13] Nathan:Sounds good.

Ali Abdaal is a Doctor, writer, podcaster, entrepreneur, and YouTube sensation. Ali has grown his YouTube subscriber base to over 2 million, and writes a weekly newsletter titled Sunday Snippets. Sunday Snippets covers productivity tips, practical life advice, and the best insights from across the web.Ali studied medicine at Cambridge University. He worked as a Doctor in the United Kingdom before taking time off to explore his other interests. His YouTube channel covers medicine, tech, lifestyle, and productivity. Ali also co-hosts a weekly podcast with his brother, called Not Overthinking.After learning to code at age 12, Ali started doing freelance web design and development. He enjoys playing piano, guitar, and singing covers of mainstream pop songs. You can find occasional videos of Ali’s music prowess on his Instagram page.In this episode, you’ll learn: Ali’s savvy insights for growing your YouTube subscriber base A proven formula for writing content titles that get clicks Ali’s playbook for taking your podcast to a whole new level Links & Resources The Nathan Barry Show on Apple Podcasts The Nathan Barry Show on Spotify Sean McCabe Pat Flynn ConvertKit Ibz Mo Casey Neistat Sara Dietschy Chris Guillebeau Tim Ferriss Derek Sivers School of Greatness podcast Lewis Howes Dave Ramsey Michael Hyatt Cal Newport Crash Course John Green Hank Green Daily Content Machine Andrew D. Huberman Reboot Dan Putt Tiago Forte David Perell Jim Collins The Flywheel Effect Impact Theory podcast The Tim Ferriss show Seth Godin Scrivener James Clear Ali Abdaal’s Links Follow Ali on Twitter Watch Ali on YouTube Check out Ali on Instagram Ali’s newsletter Ali’s website Episode Transcript[00:00:00] Ali:YouTube can change your life, but you have to put out a video every single week for the next two years. If you do that, I guarantee you it’ll change your life. I can’t put any numbers on it. I can’t tell you how many subscribers you’ll have, or how much revenue you have, like a hundred percent guarantee.You will change your life at the very least in terms of skills or connections or friends, or opportunities that will come your way as a result of posting consistently.[00:00:30] Nathan:In this episode, I talk to Ali Abdaal. Over the last four and a half years he’s built his YouTube channel from zero to 2 million subscribers.He’s who all of my friends who are into YouTube turn to for advice. He’s got a paid course. He’s got a substantial email newsletter. He started out as a doctor and then has made the switch into a full-time YouTuber. So anyway, I’ll get out of the way, but, before we dive into the show, if you could do me a favor after the show: if you could go and subscribe on Spotify, iTunes, wherever you listen.That helps with downloads. If you could also write a review, I really appreciate it.Now it’s on to the show, with Ali.Ali, welcome to the show.[00:01:17] Ali:Thanks for having me. This is really cool. I’ve been following you on the internet in a non-weird way since 2016. I remember once in, I think it was 2018, I discovered your 2015 podcast series all about launching an ebook, and pricing plans, and all this stuff.It was so good. Now we’re looking to do eBooks and things like that. Thank you for all the inspiration on that front.[00:01:46] Nathan:Yeah, for sure. Well, it’s fun to have you on, it’s been fun to watch you grow. I was actually on a hike with our mutual friend, Sean McCabe after he moved to Boise, my hometown. He was talking about you, and I hadn’t come across your stuff yet. And I was like, oh, I gotta check it out.And now I’m watching a whole bunch of videos. And then of course we’ve been internet friends for, for awhile now.[00:02:08] Ali:I’m now a customer of ConvertKit as well, for the last few months.[00:02:11] Nathan:Yeah. Let’s see. Okay. So I want to dive into your story and get some context because you have an interesting path of finishing school, like a substantial amount of schooling, and then diving into the world of being a doctor, and then transitioning out of it.What was the plan? Let’s start.[00:02:36] Ali:Yeah. for a bit of context, I spent six years in medical school, and then two years working full-time as a doctor in the UK national health service before deciding to take a break. In that break I intended to travel the world, but then the pandemic happened and I ended up becoming a full-time creator on the internet by virtue of the fact that I didn’t have a job when it was a pandemic.When I first decided to apply to med school, I’d been into the whole entrepreneurship thing since the age of 12. I learned to code. I started doing freelance web design and freelance web developer from age 13 onwards. So, in school, in high school, middle school, like we call it secondary school in the UK, I’d rush back home from school when I finished off my homework in record time, and then just be plugging away at like PHP or some HTML or some like jenky Java script. I used to make $5 here and there, and be like, yes, I’m, I’m making magical internet money. Every year when, when I was in, in high school, my friends and I would come up with a new business idea.So, we started this multi-level marketing thing and some other random pyramid schemes, and random paid surveys, and whatever we could do to make money circa 2006 to 2010. So, I always had this interest in entrepreneurship, but then when it came to figuring out what to do with my life, I was getting decent grades in school and because I’m Asian, and everyone in the UK who is Asian, their parents are doctors. So, it was like a default path for me to just like, oh, you know, why, why don’t I become a doctor? And I kind of reasoned at the time that if I could be a doctor, and also be a coder on the side, that’s like a more interesting combination than if I were just a coder or just a doctor.Not that there’s anything wrong with either, but I felt the combination would be more interesting because of the synergy. And so I ended up going to med school, which is a weird, a weird reason for going to,[00:04:24] Nathan:Interesting to him, interesting to you, or interesting to[00:04:27] Ali:Yeah.[00:04:28] Nathan:Family friends.[00:04:30] Ali:Oh no, not family and friends, interesting to me, because it would make life more fun and interesting to me because it unlocks opportunities for creating a tech startup or whatever, further down the line. I think at the time I was drinking the zero to one Kool-Aid[00:04:45] Nathan:Well, Peter Thiel[00:04:46] Ali:Yeah, like that, where I first came across the idea that like, innovation happens at the intersection of multiple fields.And so, you know, the printing press was invented by the guy who really understood, I dunno, looms and how spinning yarn worked, but also understood like something else about something else, and combined these ideas to create something cool. So, I always found it in my head that, Hey, why don’t I get really good at the medical stuff and be a really good doctor?And then on the side, if I know how to code, then I can like combine those to spin off some, fit some something interesting further down the line.[00:05:14] Nathan:I think that resonates with me of like,I think that people, especially like online creators who go and do one thing very specifically, maybe don’t have as much of an interesting angle, to put into it. Like I think that some of what made me more interested.This is like, they’re just hypothesizing, teaching like online business and, and marketing is having a design background, even though those are much more overlapping than say, like a big a doctor and, and, you know, a web developer, you know, as you were starting into it. But, but I think having those skills in another area makes you more interesting as a person and it gives you better stories to tell, and then it gives you a better perspective.And you’re not like just pulling from the same industry over and over again.[00:05:58] Ali:Yeah, no, exactly. I, I often find that the, the YouTubers that I seem to kind of, and the, and the, and the bloggers as well, who I follow more of are the ones who seem to have multiple interests. And it kind of gets to that question of like, you know, the, the thing that holds everyone back around, like, what’s my niche, like, oh, but I have to pick one thing and get really good at that.And yes, that does have some merit to it, but I often also think that, yeah, but you know, how, how can you carve out a niche for yourself? That’s a combination of the other, other stuff that you’re interested in, And so instead of trying to be the best, I don’t know, productivity YouTuber, it’s like, you’re the only productivity YouTuber.Who’s also a doctor who also runs a business that that’s kind of how I think about it.[00:06:37] Nathan:Yeah, that makes sense. Okay. So, when you’re in med school, when you started your YouTube channel or you’re wrapping up med school, right.[00:06:45] Ali:That’s right. Yeah. So, I started the YouTube channel in my penultimate year, so I, I, I, I done five years of med school at this point. I’d set up a few businesses. I had like two SAS products that I was using to side hustle, income, most my, my way through med school. And then in 2017, when I was in my final year, the YouTube channel actually started out as a content marketing strategy for my, my business, that business was helping other people get into med school.It was like that standard thing. Once you do something, you then teach other people how to do the thing. and it was like, you know, the creative economy before it was really called that where[00:07:20] Nathan:Yeah,[00:07:20] Ali:You kind of follow that model. And so the YouTube channel started.[00:07:23] Nathan:Because you were you teaching people like test prep[00:07:25] Ali:Exactly. Yeah. And it’s so similar to pet Flynn story as well.You know, he, he started off teaching people how to do some architecture exam. I started up teaching people how to do the med school admissions exams, and that’s kind of transitioned into a coaching business, which then transitioned into the YouTube channel.[00:07:40] Nathan:Okay. And so as the YouTube channel started to grow, like, what were some of those first milestones, you know, as you’re getting to, how long did it take for you to a thousand subscribers and then maybe, you know, 5,000 or 10,000? Like what milestones stand out.[00:07:52] Ali:Yeah, so I started in the summer of 2017 and it took me six months and 52 videos to get to the first thousand subscribers, six months in 52 videos. I was putting out two videos every week while preparing for med school finals and kind of neglecting my exams for the sake of YouTube, because I could see the YouTube thing was like, oh, I really want to do this.I think the ROI on being a YouTube or is going to be higher than the ROI and getting an extra 2% in my med school finals. that was, that was the theory. Anyway, So, yeah, it took six months of the channel to get a thousand subscribers, another like four or five months for it to get up to 5,000 subscribers.And at the point where I was at around 4,005,000 subscribers, there were two like really good things that happened. Number one was a collab with a much bigger utuber. his name is Ibz Mo. So he and I got to know each other through university and he had 60 K at the time. And so he and I did a collab which took off and helped the channel get exposure.But also there was a video that I made my, my very first video that actually went viral, which was a video about how to study for exams. now this video is a bit weird because like I’d actually planned for it to happen like a whole year before I made it. So when I started YouTube, I, I sort of consumed the hell out of everything on the internet, around how to be a YouTuber and, Sara Dietschy and Casey Neistat had this thing whereby Casey Neistat, enormous YouTuber, Sarah DG would take YouTube who was smaller at the time.She went from 40 cases. Over to like one through over a hundred, a hundred thousand, basically overnight because Casey Neistat shouted her out. and the way that she described that, and I, that I found in some random interview, like on the YouTube grapevine, was that you, you benefit from a collaboration with a bigger utuber, but you only benefit from it.If there is already a backlog of really high quality content on your channel. And so I took that to heart and I knew that, okay, at some point I want to do a collab with a bigger utuber. And at some point I want to try and make specifically a video on how to study for exams, but I knew number one, I needed to have a backlog of hot, cold, high quality content because otherwise no one would care.And secondly, I knew that it would take me about a hundred videos to get good enough at making videos to actually be able to make a decent video about exams. And so that was like my 82nd or something video, which I, I, I I’d had in the back of my mind for so long since, because since getting started button, you know, I need to get my skills up.I need to put in the quantity so that I can actually make videos that are hopefully.[00:10:06] Nathan:Okay. That’s interesting. Yeah, because coming, doing a collab and coming to a channel and it’s like, okay, they have four videos. And the one that I saw in the collab is actually the best one they’ve ever done. Like it’s sort of, it doesn’t have the same ring to it as if you come in and be like, wow, this is incredible.Like, one of my favorite bloggers, you know, it’s separate from the YouTube space, but I got him, Chris Guillebeau was an author and blogger and I followed him in the early days. And I had the experience of, he had written a guest post for Tim Ferris and I was reading Tim versus blogging. This was probably 2011, maybe.And I was like, oh, this is really good. I love it. I think it was on actually on travel, hacking, you know, credit card points and all of that. And so I clicked over to his site and I think. Over the next, like two days, I just read the entire website, you know, Nate, it was like years worth of blog posts and all that, but that was the experience.Right. The guest posts is a collab of some kind and then coming over and you’re like, you’re just deep dive and consume everything rather than the experience of coming over and be like, oh, okay. That’s interesting. You know, and like moving along and the back catalog is what, what, drives that?[00:11:09] Ali:Yeah. Yeah. I had, I had that exact experience with Derek Sivers who I discovered through the Tim Ferriss show and Mr. Money mustache, but it’s coming through a temporary. I was like, all right, I’m spending the next week of my life. Just binge reading all of your blog posts that you’ve ever written for the last 20 years.And now it’s like, I’ve got this information downloaded into my brain.[00:11:24] Nathan:Yeah. I love it. Okay. So one thing that I wondered about is as you spend all this time, you know, on med school and, and then, you know, becoming a doctor, it’s a big investment. then you also have this love for YouTube and the channels growing. Like the channel now has 2 million subscribers and, and, this is wild success.How do you think about. Like when you made that switch to YouTube, as your full-time thing and leaving behind, at least for now your career as a doctor, how did you make that decision? How did sunk cost play into it? You know, all that,[00:11:59] Ali:Yeah. So this is, it’s still something I think about to this day. It’s like, there’s this balance between how much do I want to be a doctor? And how much do I want to be a YouTuber? when I made the decision at the time, it was, so it was about actually this time, last year, where I took a break from medicine intending to travel the world, but then pandemic happened and ended up being a full-time YouTuber.And then like back then, what I was thinking was I’m, I’m only going to do this for a little while. Cause this YouTube thing is going well right now, the problem with YouTube and like the creative stuff in general is that there’s not a lot of like longevity to it necessarily. Like there are so few YouTubers who are big today that were also big 10 years ago.And so that’s the thing that I constantly keeps me up at night. Like how will I continue to stay relevant? You know, X number of years from now. And to me, the medicine thing always seemed like a great, you know, my main hustle is being a doctor and my side hustle is being a YouTuber so that no matter what happens, you know, at least I’ll have a, a full back career to kind of fall back on.[00:12:53] Nathan:Pretty sure doctors have irrelevant 10 years now.[00:12:55] Ali:Yeah, I’m pretty sure doctors will be relevant. So I wouldn’t, I wouldn’t have to worry in that context. in the UK, the way the medical system works, there’s also like, after you’re a doctor for two years, at that point, there’s a very natural gap and a lot of people will take some time out to, to go traveling or whatever.And just so happened that COVID happened to that exact point just as I just, as I left to take a break. But I was, I was on the, the school of greatness podcast with Louis hose, last, last week. And he, he was calling me out on this. He was saying that basically I was bullshitting myself because I think the reason why I was holding onto the medicine thing was a profound sense of risk aversion.It was number one. The what if I, what if I lose everything at least then I’ll still be able to be a doctor. And number two, it was a case of like, oh, but. I, you know, my brand was built up of the back of being a doctor. And if I lose that, then you know, who am I, why does anyone listen to what I have to say?Who will care what I have to think anymore? Because now I’m just a YouTuber rather than a doctor, which has like prestige and it has like clout. And he basically just called me out and dismantled, like all of my BS on all of those funds. And that really, really got me thinking. Cause like, you know, ultimately the thing that I care about is teaching and inspiring people.And if I think about, if I could only do one thing for the rest of my life, it would not be saving lives as a doctor. It would be teaching people. And that’s the thing that YouTube lets you do and lets you do it at scale. And that’s the thing, the internet that today. And so now right now I’m going through this phase of having to really think about like, am I only holding onto the doctor thing because of because of fear. And am I holding onto fear and sunk costs, which is obviously like a stupid thing. do I really want to go all in, on the YouTube stuff and then the business stuff, because my real passion is teaching. I don’t know any, any thoughts on that balancing, like the fear and like the sensible decision would like following your passion.And it sounds so cliche, but yeah.[00:14:48] Nathan:Yeah. No, it all makes sense to me. The place that I would go is, you know, as you, cause there’s, there’s fear on both sides, right? I’ve given up the, being a doctor and then there’s fear of what does this career as a, as a creator, as a YouTuber look like in five years, in 10 years. And I would lean in on that side and try to figure that out.Like who are the people, questions I would ask, who are the people who. You admire, who have had longevity in their careers. Right. Cause in the, in the blogging world that I’ve been a part of the last I want to spend, I guess, almost exactly 10 years now. There’s a lot of people who are not around anymore, you know, like they’re still alive.I’m sure they’re living wonderful lives, but they don’t live internet, you know, internet visible lives anymore. and then also seeing like what, what does your business look like in that? It’s how you do dependent? Is it, what does that look like? So as you look five years ahead, this something I want to ask later, but, but I’m curious for now, like five years, 10 years ahead, like what are you doing?What’s the, what does your, your audience look like? And what role does YouTube or other things play in[00:15:50] Ali:Yeah. Yeah. I think if, if, if I think about people who have longevity, I think you’re one of the examples that comes to mind where you started off as a blogger, and then you did the ebook thing, and then you went into the SAS thing, which is now like, absolutely like, you know, exploded. so that’s really cool.The other people who I look to are, you know, people like Tim Ferris, who. Has gotten bigger every year, since before I work, we came out and it wasn’t a one hit wonder. We started off with the books and then he did a great job of transitioning into the podcast where now it’s less about him and more about kind of spotlighting other people and building this almost the institution of his, his personal brand, which is built off of teaching people.Cool, cool things. yeah, I think about it, like in that context, like the thing that you and Tim have in common is that you’ve both gone, moved away from being very personal brand heavy and more towards being somewhat institutionalized in your case and convert kit in his case, through his podcast.And that’s kind of how I see it for myself in a dream world, whereby let’s say five years from now, I’m still like doing YouTube videos and teaching people and I’m learning things. And then teaching people, the things that I’ve been learning. Cause I, I enjoy that kind of stuff, but it’s become, becomes less about me personally and more about kind of showcasing other experts.Building a team and building a brand that can be dissociated from my personal name, if need be.[00:17:09] Nathan:Is there a blueprint that comes to mind? So I think about this, a lot of where, where this goes with the highest leverage point to direct an audience to, I —-wrote an article called the billion Abdaalar creator, that is about like this exactly of, you know, if you have an audience of 10,000 or a hundred thousand or a million people, like, what is the thing that you would point that to long-term.And so I’m always looking for these blueprints that other people have created, right? Like I think, Dave Ramsey would be an example of someone who has taken this.Podcasting a radio show is basically a podcast. you know, and taking it to this extreme of, I don’t know what they have, I’m making up numbers, but in the ballpark of like 500 to a thousand employees, they’ve got like this franchise thing, they’ve got courses that they’re, you know, you can sign up for everywhere.Like it’s this massive media empire that I can draw a pretty consistent line from, you know, blogger with 10,000 subscribers or 10,000 podcast downloads consistently to that of like continually working away at it. Not to guarantee you that, that you’ll hit that, but you know, there’ll be other people on Michael Hyatt or, anything else or there’s the software direction that I went.So are there like specific blueprints that you look at and be like, okay, that, but[00:18:30] Ali:Yeah.[00:18:31] Nathan:Of it.[00:18:32] Ali:Yeah. I think for me, the playbook that I’m currently following is trying to be a cross between Tim Ferris and Cal Newport.In that Tim, Tim Ferriss in the context of starting a podcast, interviewing experts on stuff. And I need me to, I probably add someone to that. Tim Ferriss, Cal Newport, and the crash course, the YouTube channel, which is run by Hank and John Green, whereas also taking the Tim Ferriss model of podcast, interviewing other people.And then, then that becomes its own kind of content, which helps people, the Cal Newport model of actually I think he he’s done a great job of straddling the two worlds of old world prestige of being a professor at Stanford or wherever he’s a professor at a part-time and also being a part-time writer and blogger and internet personality type person.And then like taking elements of those and combining it with like the YouTube airy type thing, whereby I think, I think what’s missing from the world of podcasts these days is that there are so many podcasts and there is so much incredible wisdom, which back in the day used to be locked up inside either textbooks or in scientific journals.Now, the people who write those scientific journal review papers are being interviewed on all the podcasts. but they’re being interviewed in the context of a three hour long discussion. And yes, you could listen to the three hour long discussion. Yes. You could listen to the podcast clips that they’ve got, that they’ve been posting through Daily Content Machine on Twitter or whatever, but it’s just not as actionable as someone actually creating a compelling YouTube video.So, you know, you could listen to Andrew Huberman interview, the world’s expert on longevity about all the eight different things you should do to increase your life. And very few people would follow that advice because there’s no in a digestible format. And so if I’m thinking like what I’m, what I’m thinking is that if we can do the podcast thing, we can do the kind of Cal Newport thing of combining old world prestige with new world, kind of content, and also do it in the format of like YouTube videos that are accessible to the mass market and, you know, a lay person audience that is kind of the combination that I see myself doing over the next like five years.And that feels quite exciting.[00:20:32] Nathan:Yeah. So that target of like the 10 to 15 minute YouTube video, that’s really well crafted and architected to have the table of contents and even skip to the sections. And it’s like, look, this is what you need. And it’s not just what was covered in an hour long interview, but also like, and then we pulled in this and when they referenced this thing, like, this is what they’re talking about.We can illustrate it with visuals and everything else.[00:20:55] Ali:Absolutely. Yeah. And that’s the thing that I’m hooked. So in the process of building a team around, which is something I wanted to talk to you about because you’ve built a big team over time, I was speaking to Derek, you’re a director of marketing as well about building a team and he had, so he had loads of advice to share.So that’s, that’s a challenge for me right now. It’s like, you know, two years ago, it was just me last year, this time, last year, there were three, three of us full-time well, two full-time. It was me working as a doctor and a part-time assistant, and now there’s 12 of us, but now we’re hiring another 10 people.So by next month it’s going to be maybe like 20, 20 of us a hundred. It’s all those problems associated with scaling a team and leadership and management. And that’s the kind of stuff that, I’ve been really as sort of very much on the steep learning curve of, and that I’m very excited about getting better at,[00:21:44] Nathan:Yeah. what’s the reason that you’re growing the team so quickly.[00:21:48] Ali:Well, let’s see, because we just have a lot of money. once, once we launched our, yeah, it’s a, it’s a, it’s a good problem to have. We’re just like very cash rich and expertise poor as someone described as, We launched our cohort based course part time, YouTube academy this time, last year, it did phenomenally well, I’d been doing classes on Skillshare, which started off as making like a few hundred to a few thousand a month and is now compounded to the point where we make some way between 60 and $80,000 every month, just passive income of Skillshare classes.That means that every month we’re just making more and more money. And I see the, I see the numbers going up and I see them go up and I, I see basically like, well, why, why are, why aren’t we doing anything with that money other than just[00:22:30] Nathan:Right.[00:22:31] Ali:every year.[00:22:32] Nathan:Okay. So really quick, since you mentioned, are you okay sharing some of the numbers, like the numbers from part-time YouTube academy?[00:22:38] Ali:Yeah. so we launched the first cohort in November last year. I think this year we’re on track to do maybe like $2 million revenue and like 1.1 0.5 million profit, 1.6 million profits, something like that. next year we’re hoping to take that up to like 5 million revenue. Which again, all of these feel like, like dumb numbers, I’m just plucking out of thin air.Cause it’s like, I I’ve, I’m, I’m really bad at like projecting, protecting financials. Like it’s all, it’s all just a guess. Anyway, like if we could do four cohorts and sell 600 places, that would be 5.5 0.1 million revenue. It’s like, that’s actually, that’s actually doable, but it’s just such a fricking ridiculous numbers.It’s like, how on earth can that be doable? It’s just like, how, how does it even work?[00:23:23] Nathan:Yeah. Welcome to the internet. And, when you have substantial leverage, like things that were possible, like seemed insane before you’re like, oh yeah, I know that math checks out, you know?[00:23:34] Ali:Yeah, exactly. I suppose if somebody, to you for ConvertKit was I think last I checked, you were on 20 million annual recurring.[00:23:41] Nathan:Yeah. We’re at 20, 28 and a half. Now[00:23:44] Ali:Well the hell that’s going to quickly compounding.[00:23:48] Nathan:The magic of compounding, This is fascinating to me because a lot of, I feel like a lot of content creators are, you know, get to your stage and they’re like, okay, what, you know, what Lamborghini should I buy right now?Have you thought about putting the line beginning in your YouTube videos? I’m kidding, please.Don’t[00:24:05] Ali:I mean, I’ve got a Tesla model three, so that was my, a splurge.[00:24:08] Nathan:That was your splurge. Yeah, exactly. you know, so interesting to me that you’re hiring at the rate that you are, which is to be totally clear is the rate that we hired at ConvertKit like slow at first of like two or three, four, and then it started to, like started to really take off. And I think in, let me think how long eight months we went from four people to 21 people.And, and that worked really well for us. And we were growing really, really quickly. And, and, like in that time, I think we 10 X revenue, like going. 30,000 a month in revenue to 300,000 a month and revenue. and so that that’s absolutely a wild ride. And then we kind of paused there for a second and we like methodically about, okay, what are the roles that we need?How do we build the team culture within the group that we have? How can we invest in those relationships? We also had our first team, like in-person team retreat at that time. and so I think it’s really important as you grow a team that quickly to make sure you’re really, really, yeah. Intentional about, the team culture, which like, that’s one of the things like, what does that even mean?How do you, how do you do that? And the way that I do it is being clear about the mission of what you’re building and why. and then investing deeply in the relationships with each person.[00:25:32] Ali:Okay. And what does, what does that mean?[00:25:34] Nathan:Was, so you’re hiring all these people, right? And let’s say you’re hiring from you’re very much the face of the.And so if someone’s applying to like, oh, I want to work with Ali, right? Like, let’s do that. And so they have this relationship with you and what you don’t want is this, you’d end up with this hub and spoke model where you’re the hub and everyone has a relationship with you and they don’t have it with each other.And that’s just the, it’s a natural way that things are joining, right. Or the way it comes about. I, the same thing when people wanted to start working at ConvertKit, they wanted to work at convergent, but they a lot wanted to work with me. And so you have to invest deeply in turning that hub and spoke into like a spiderwebs where if you’re not at the core of it, they all are riffing on ideas.They, you know, understand each other’s, families and like individual values and everything else. and that matters more. And so you have to know that the natural state of things is not ideal and you need to like aggressively work, to change that. So that you’re less important than your own.[00:26:39] Ali:Oh, interesting. Yeah. That’s exactly the challenge that we’re having right now where. Still all of the things kind of flow through me, but it’s, I think over the last few months, as I’ve gotten like business coaches and working with, with our mutual friend, Sean, as a coach, as well, and reading sort of dozens of books about like leadership and management and like org chart structure and all that jazz, we’re starting to get to a point where I actually do feel like stuff is happening without me.And it’s like the best feeling in the world when they’re just doing stuff. And I’m like, whoa, wow. That’s actually a great idea. It was so well done. And you’ve actually done this better, better than I would have done this. Whoa. Okay. This is really cool. so hopefully as the team expands, yeah, the, the, the culture thing is interesting.I think so far, I haven’t given any thought to culture in the slightest as just sort of happened organically slash accidentally. but one of the exercises that Sean, Sean took me through was the thing of like, imagine, you know, a year from now or three years from now, what is the sort of business that you want to have?Like you go into work in the morning, like what, what do you want to say. It was only after that. I kind of thought about that, that I realized that for me, what that dream looks like, it’s actually having an in-person team having like a studio, maybe, maybe in a place like London that we can invite people over to for podcasts and focus for collabs having an in-person team.Or maybe once a once a week, I have brainstorm meetings with, you know, our writers and researchers and stuff, and we figure out what we’re doing. Maybe once a week, I filmed stuff for the YouTube channels. And maybe once a week, I sit down to record a podcast with someone cool. And the rest of the time I spend like chilling, or, you know, writing or reading or doing other, working on the businessy type stuff.And we have like a COO or general manager or whatever you want to call it, who runs the day-to-day operations without needing my input. and it was only really when I kind of said that out loud, I’m just going to ask, so, okay, well when you just make that happen and I was like, oh yeah, you’re right.I could just make that happen. And then, because I think before I just, I, I drank the remote work Kool-Aid so, so much that I just sort of assumed that you had to hire remotely. Then I realized, hang on, given that this is the sort of business I want to be in where we’re all actually in person, because it’s more fun.I can just hire people who are only London. And so when we’re not doing that, hiring people who are only in London, which feels weird, but it means we also have, you know, a few dozen applications rather than a few thousand to, to deal with, which is, which is kinda nice.[00:28:59] Nathan:Yeah. And that’s something that when you get clear on that, and that’s why so many people want, besides journaling or whatever, other journaling coaching, any, any form of getting that clarity, it’s you realize that you’re like following this meandering path and like, and then we can do this and then that, and then you realize like, oh, I can just draw a straight line from point a to point B and just do that now.And it’s, it’s so powerful and you’ll save yourself a lot of trouble because then you won’t be at a point, right. Where you say we’ve built a 25 person team. That’s like, maybe there’s six in London. And then, everyone else is spread throughout the world and people are loving aspects of that, but then they’re feeling like the people in London are getting more time with you and right.And you go and create this major culture problems because you had an intention like, or an internal desire that you never expressed, explicitly. And then once you express that and then everyone’s like, oh, okay. So I know that it’s them working for you remotely right now. I know that I either long-term need to switch to being a contractor of like, just providing a service, you know, or I need to move to London or I need to fully transition out.Like, and there’s like a beautiful clarity in that, that when you just keep it inside, you like no one will, no one will experience.[00:30:17] Ali:Hmm. Have you, have you got any like prompts that you find helpful in this sort of journaling thing and figuring out what you want from the business and from life?[00:30:25] Nathan:So, you and I both share a passion for coaching and I hire a coach as well as name’s Dan, from an organization called reboot. so he asks all kinds of questions. one, I was navigating a scenario recently that was just really frustrating. And, he said, okay, I want you to picture when you’re 40.So I’m 31 right now. So nine years from now, how would your 40 year old self looking back, you know, basically 10 years be proud of how the situation was handled. And that was a version. So basically the prompt would be like stepping forward, not just, what do you want 10 years from now, but like stepping forward and trying to really imagine that scenario.You know, what’s pushing you to do, and then looking like looking back on it as a memory of how you handle this next period of difficult transition or any of that. So that’d be one version. Another is like really pushing on like the five why’s and really digging in of why do you want that thing? What do you, what are you actually trying to accomplish?I’m sure there’s more, butYeah. Are there others that you use.[00:31:38] Ali:Yeah, that question of why did I come across this? I can’t remember where I was like to cite my sources, but, the thing of when, when making a decision, think about what decision your like 10 year older self would have wanted you to make, to be like the best version of yourself.And I’ve been thinking about that recently in the context of this thing of do I go all in on the YouTube thing or do I just kind of do Hoff medicine off YouTube? And I do think out of 10 years from now, I would have wanted myself to make the decision of actually just going all in on the passion project and just seeing what happens with that.If it doesn’t work, it didn’t work, but at least having a go rather than feeling kind of pulled in two directions, which are sort of incompatible because of the amount of time commitment that a physical career like medicine takes.[00:32:25] Nathan:Yeah. And it’s hard when you’re like, if you have a 10 person team and you’re, you’re the only one that’s part-time right. Like that, that will result in, you wish you could spend more time with the team. You, you know, you being the bottleneck and things, you shouldn’t be it made me think of like the, on the team side of things.There’s a movie called the intern, Robert DeNiro and Hathaway.[00:32:44] Ali:No, yeah. I really enjoyed that. It[00:32:46] Nathan:It’s a fun movie.And there’s a scene in it. So Anne Hathaway runs this, like a fashion tech startup, but th but there’s a scene early on when she’s like rushing from thing to thing and everything is going to her for approval and all of this stuff.Right. And I remember watching the, how she’s so important. It’d be nice to be that important. And then the second one, you stepped back and you’re like, that is a terribly run business. Like, what is she doing? You know, like the whole thing, if she wasn’t there, the whole thing would fall apart. Cause no one would have our approval for like the homepage designs or, or whatever else.And so, going back to the hub and spoke thing, that’s the, you know, you’d like watch that little clip of the movie and then go, okay. That, but the opposite, like that’s[00:33:30] Ali:Yeah,[00:33:30] Nathan:To go.[00:33:30] Ali:Yeah. There’s one. So, often, you know, someone in my team will message me being like, Hey, you know, we, we need to discuss item X. can you, me and Angus hop on a call and discuss item X. And these days are reply with, can you and Angus discuss item X? Like, do I absolutely have to be on this call?And they’re often like, oh no, I guess you don’t. Yeah. You know, I mean, I’m just gonna take care of it. I’m like great, wonderful. and I’m always surprised when that works. it’s like, oh yeah, this doesn’t work. I actually don’t need to be involved in everything. but I guess it’s, it is that balance of, and I think sometimes the team does feel frustrated that I I’m involved in too many things.I’ve heard and they feel like maybe I don’t necessarily trust all of their decisions. it’s like, you know, my name that is going on all this stuff and I trust, but I want to, I want to be able to verify, like if I ask why was something done? Like why, why that pricing plan, rather than that pricing plan,[00:34:22] Nathan:Right.[00:34:22] Ali:Like a reason behind it beyond, oh, it’s just, we just sort of plucked numbers out of thin air.[00:34:26] Nathan:Yeah. So two things that makes me think of is one, creating a culture where asking questions is encouraged and not just, Like asking questions of like, Hey, could you explain this to me? I truly don’t understand it, but, but also like asking for, is there a reason behind this? You know, why did you do that?And then the other side, when people come to you and say like, Hey, what do you think we should do? Then you ask them, what do you think we should do?And then going like, oh, well I think X, Y, and Z. And you’re like, okay, why do you think that because of this great, let’s do that. You know, you have more and more conversations where like people come to you and then they make the decision and[00:35:05] Ali:Yeah,[00:35:05] Nathan:Place.[00:35:06] Ali:Yeah, yeah. I’d love to get to that point. I think I need to do a better job of, of doing that. the most, the most obvious example is like when we’re brainstorming video content ideas and we’re coming up with titles. so we had a meeting earlier today and, you know, the team came up with a few concepts and like 20 titles for each one.And then I made the final decision. I was like, oh, I kind of liked the sound of like title number five. but what I probably should do in that context is, okay, Gareth, if you were making this video, what title would you go for? And then kind of seeing what happens. And I guess there is an element of like, you know, I, I trust my gut on what makes a good title more than I trust anyone else’s in the team Scott’s or what makes a good title.But I’d like to be able to either train someone it’s hard to train someone for this, like find someone who’s got like trust more. And so who, who I can just fully outsource the responsibility of coming up with a decent title for, because it is such a huge part of what makes a successful YouTube video[00:36:00] Nathan:Yeah. Okay. On those lines. When you make a video, do you know how often do you know when it’s going to be like a video that really hits?[00:36:09] Ali:Think about 20% of the time.I can, I have a gut feeling that, okay, this could be a banger. and th the way I think about it in my head is sort of in terms of Banga potential. So a video called I dunno, nine passive income idea is how I make $27,000 a week that has high bang of potential, a video call.The power of positive thinking the potential, like that’s not going to be back. It’s like, okay, can we increase the bang of potential by making the title more clickbait? and so for example, you know, I’ve been working with a life coach for the last few months. I want to make a video about it. I’ve been thinking, you know, how, like really the thing I worked with them on was how to figure out what I want from life.But a video called how I’m, how to figure out what you want from life. You know, maybe two out of five bang of potential, a video called I hired a life coach for $3,000. Here’s what I learned. That’s got bag of potential. And so often it’s just like a tweaking of the title where it’s like the more click baity and sensationalized the title that is annoyingly often.The thing that chorus that correlates most strongly with how much of a banger is this city you’re going to be. And the formula that I try and use is sensational click baity title combined with like very deep nuanced. So that someone clicks on the video thinking, huh? And then they’re very, very impressed by the production value by the structure, by the academic newness of it, by how awful it is.I think it’s crossed the Pepsi, at least that’s the intention.[00:37:32] Nathan:Okay. That’s interesting to me. I have this like running fantasy as I teach. People how to build wealth and make money. Like, those are some of my favorite topics. I can talk about them all day. And so I was joking with someone that I was going to do, like these real estate seminars, you know, that you see advertised where it’s really scammy or you’re really just paying for that person’s private jet.You know, or it’s like, it’s the, the MLM equivalent, multilevel marketing equivalent of whatever. Like I’m going to use the same tactics, but then like actually deliver real value. And like the ticket that I charged would just be like 50 bucks and it all go to, I don’t know, clean water, charity water, or something like that, you know, basically saying like, I’m going to hook people in with the same thing, clickbait and then deliver, like substantial value that will actually be life-changing.Yeah. And so[00:38:23] Ali:Yeah.[00:38:23] Nathan:The same thing. I like it.[00:38:25] Ali:Yeah. I think it’s a great idea because you kind of need to use the clickbait. Like there’s literally no way someone’s going to click on something. there’s a channel, V very, to cm, which made an amazing video, like a few days ago, about the difference about the importance of clickbait and how, and how much it works.And his overall point was that like click, click bait is kind of the wrong word. There is sort of, I think, I think the two terms where there’s this sort of like intrigue Bates, which is that, you know, oh, this is interesting. I want to, I want to click on this. And then there is, I can’t remember what he said, but it’s like, sort of trashed bait, which is that I’m going to stick a bikini model on a thumbnail and has nothing to do with that.But, and so there’s those two, two different ones where like, in a way, the way that you title something or the title of your book or the cover of some. It’s so, so important for getting the message across. And we shouldn’t see that as being a bad thing. Whereas the word clickbait, it includes, you know, things like what is what what’s a good headline designer.What’s good marketing coffee, but it really shouldn’t because clickbait has, it is a dirty word, but it, it shouldn’t be because the cover of something is so important to how that thing is perceived and whether people are going to see it or not.[00:39:33] Nathan:Yeah. Yeah. That makes sense. How do you think about the thumbnails and then like the, say the first 30 seconds of the video, those are two separate questions, but as both of those in, in driving engagement,[00:39:44] Ali:Yeah. So thumbnail is really, really important. I think on our channel, we were bad at thumbnails. I’m not a fan of our thumbnail style. we’re trying to evolve and iterate on it over time whereby the, you know, and so w w whenever someone’s an early stage, utuber, it’s like, you’re, you’re uploading the video.And then you think about the title. And then you think, okay, let me find a, still from the video that I can use with someone else, and then maybe you downloaded it, ramp up the contrast saturation, blah, blah, blah, sticker, clarity, filter on it, and maybe put some text on it in Canada. That’s like the, the new YouTube, YouTube way of doing it.When you become a little bit more pro you start thinking of the title in advance anything, okay, what’s the title of this video going to be, and then you make the video and you’ve got the title already. but the thumbnail is still a bit of an afterthought because it’s, it’s quite hard to think about something else.And that’s the point where we’re at. and the gold standard is where you have full about the title. And you have literally made the thumbnail before you even think about writing the script for the video. And that is a place where we would like to get to. so we’re looking to hire like a graphic designer and, you know, a YouTube channel producer whose job it’s going to be to work with a graphic designer at any time, because we, we we’ve got hundreds of ideas at the top of our pipeline, but at the moment, our bottleneck is in developing those ideas, crucially with a decent title of decent thumbnail and a rough talk, rough amount of talking points.And so, yeah, we’re doing everything we can to make the thumbnail more of a first-class citizen, because it’s just so stupidly important on YouTube. And in fact, often, you know, if, when I’ve heard YouTubers would like 10 million plus subscribers speak about thumbnails, they view the thumbnail as being even more important than the title, because the thumbnail is the first thing that really catches the viewer’s eye.And the first thing that they see. so yeah, I think we do vaginal thumbnails. Well, relatively speaking, and we’re trying to improve at it. I think equally the first 30 seconds is just ridiculously important where everyone’s attention is so like all over the place, but if you don’t hook the viewer within the first like five seconds, you see that huge drop off in engagement.And again, other other YouTubers that I look up to really, really obsess over the first 30 seconds to one minute of the video and when we teach our YouTube, of course, and we analyze like, what makes a good, like what do these sort of 5 million plus view videos happen? It’s like often there’s like a cut every single second in the first 30 seconds, like some new piece of gear or something happening on screen.It’s just like so rapid and fast and really holds your attention. Whereas for the rest of the video, you can kind of switch to a car every five seconds or something happening every 10 seconds, the ten second rule. but certainly the first 30 seconds, like Panama, it’s gotta be like really, really, really sharp and on points.Otherwise people just don’t watch.[00:42:16] Nathan:Yeah, that’s fascinating. I’m realizing that it’s true for a lot of channels I’ve seen grow really quickly are employing the same things. that’s something that’s I wanted to ask you about on the monetization side is you’re selling a high value course, to like a big audience, you know, 2 million subscribers on YouTube.You also have a what? Lower a hundred thousand subscribers on, on email.All right.[00:42:38] Ali:Yeah.130 or something.[00:42:41] Nathan:Nice. What’s the, like, how does your approach differ when in promoting that, you know, a new course, like the part-time YouTube academy on YouTube versus on email.[00:42:50] Ali:I think I’m still scared of selling. It’s really bad. I need to get over it. I was, so I was really, really scared of selling like a year ago. And when I had the idea for the part-time YouTube academy, it was on like the 16th of August, 2020, where I wrote the notion page about it for the first time I was thinking, okay, you know, this, this is either going to be a Skillshare class.I eat free, or it’s going to be like maybe a 50 to $200 kind of self-paced course. And you know, I can really, really over-deliver on content. Cause I know what I’m talking about here. And so $200 is an absolute steal for this. No one’s ever going to complain that this is not worth it. And then I spoke to, I think people that you probably know Tiago Forte and David Perell who run their own like cohort based courses.And they challenged me. You know, what if you had to do this live? What if you had to charge a thousand Abdaalars for it, how would it change your approach to the course? And starting to think in those terms made me really changed the way that we did a personal course and it became a high, second thing. It made me realize that actually what the world needed was not, or what needed to be grandiose, like what the internet needed.It was not, another YouTube or making a self-paced course on how to be a YouTuber. The thing that’s actually holding people back is the accountability and the community. And these are things that you get in a live cohort. but getting back to your point about how, like the difference in, in setting it.So we actually only advertised it on Twitter and on the meeting list. initially I didn’t even mention it on YouTube because I was so scared of mentioning the course on YouTube. And I think the reason I was so scared of mentioning the course on YouTube is a problem with YouTube that I’ve spoken to a bunch of other creators about, which is that the people who comment on the videos do not reflect the audience at all.[00:44:29] Nathan:Right.[00:44:30] Ali:Like, if you think about who comments on a YouTube video, it’s generally kids, it’s generally kids with with enough time on their hands to comment on to comment on videos. And so I was always scared. Like, my audience is not going to appreciate the fact that I’m selling a high ticket course. They’re going to think I’m a snake oil salesman or something like that.And my audience mental model was the people who comment on my videos. And it took me a little bit of like an epiphany to realize, hang on, the people who I’m targeting are people with jobs. People would like, you know, six figure incomes, people who want to do the creative side hustle and take it seriously.They are not the 14 to 17 year old kids commenting on my videos. And that was such a major like revelation of like, I can actually completely ignore the comments and I can just go by the analytics that tells me like 40% of my audience is age like 24 to 36 in the U S fantastic. Those are the people I want.Whereas on email, you don’t really see that as so, so clearly. And so I think, and especially because I’ve read your stuff. Read a lot around email marketing, but so little around YouTube marketing. I’m much more comfortable selling on email than I am selling on YouTube, but it’s, it’s something I’m trying to get better on.So,[00:45:31] Nathan:Are you able to track attribution for signups or that kind of thing of what’s coming from YouTube versus email now, right? You’re doing at least some promotion of it on YouTube.[00:45:40] Ali:Yeah. we actually, so in the first cohort where we did, we didn’t promote on YouTube at all. So it was like 50% Twitter, 50% email, I think for the most recent cohort, even now we don’t really promote on YouTube very much. It’s less just like a very, very subtle casual plug at the start of a video.I think about 30% came in through YouTube and the rest came in through again, Twitter or email.And so, but you know, one of the things that we’re hiring for is a marketing marketing manager to basically just lead marketing for the YouTube academy. And that was some of the stuff that, that your pal Derek was was, was helping us with.[00:46:13] Nathan:Yeah, they’re good at all of that kind of stuff of taking, I mean, all the things that I did over the years of like, oh, there’s, one-off push here, they’re entering into like, okay, that was great. Look at the results we got from it. Also, we’re going to do it as a system now, and it’s going to work like this and it’s going to drive consistent results over time, rather than like these spikes or that sort of thing, which I’m good. okay. Something else like in that journey, we kind of left off as you were, you know, I guess the last we’re talking about YouTube numbers was, you know, like five, 10,000 subscribers. I want to hear a little bit more about going from that 10,000 to 100,000 and then like, I think it’s a huge jump, but a hundred thousand to 2 million.[00:46:54] Ali:I think it is absolutely fancy. It’s just the law of compounding and consistency and, you know, the results happen very, very slowly and then very, very fast. And before you know it, you know, Jim Collins, I thing has that model of the flywheel that it takes. It takes a hell of a lot of energy to get going, but once it starts to go, then it, it becomes unstoppable.I think it’s, it’s the case for any interesting kind of compounding could growth projectory, you know, YouTube channels, convert kits, any software platform that’s growing. and so in year one, I think we hit maybe like 20,000 subscribers by the end of it. Then year two was probably the next few hundred thousand year three was the next like million in year four.It’s just wrapped up wait, where we just hit the 2 million mark. And then at the end of year four, so it was just, you know, perfectly matches it maps onto one of those exponential growth curves. The scary thing about that is that like, if you extrapolate it further, that means we’re going to be on like 4 million subscribers by next year.And that’s just completely unfathomable to me because it’s like, okay, that’s just never gonna happen. And there is a point at which the, the compounding growth curve stops, That’s the thing that I worry about. I don’t really worry about it. That’s the thing that I’m trying to build more and more like pillars of support around the business, a diversification, more into courses, more into books, more into stuff that is dissociated from my personal brand and also from my personal YouTube channel specifically.Yeah, it’s, it’s, it’s weird. It’s one of those things we look back on and you kind of forget like, oh yeah. When, when I started, like, I remember like when I started working as a doctor, I had, I hit 50,000 subscribers like that, that, month. And then a year later when I was having my first like appraisal, where they, your supervisor looks at how good a doctor you were.The first thing he said to me was there were 263,000 people following a YouTube channel. How the hell did that happen? And so I have that number in my head is like, oh yeah. Once I, at the, at the end of 2019, when I, when I finished my first year, I was Dr.. That was what. And then it was like my it’s my second year of working as a doctor when the pandemic struck and the pandemic, me and my channel really take off because all of a sudden people were sitting home and watching YouTube videos.I think that was when we had and subscribers. and now a year on from that point, we’ve just had 2 million and it’s just been just insane, insane growth. but obviously consistency compounding the thing I always tell my students is that, you know, YouTube can change your life. but you have to put out a video every single week for the next two years.And if you do that, I guarantee it’ll change your life. I can’t put any numbers. I can’t tell you how many subscribers you’ll have or how much revenue you have, like a hundred percent guarantee. You will change your life at the very least in terms of skills or connections or friends, or, you know, just opportunities that will come your way as a result of posting consistently on YouTube.And everyone here is that advice. And like, you know, so few people actually follow that,[00:49:43] Nathan:Yeah.[00:49:44] Ali:With me. You know, I’ve been trying, I’ve been trying to hit the gym for the last like eight years. Never done it consistently until I got a personal trainer and now I’m actually seeing gains, Yeah, compounding and consistency, which is some of the stuff that you talk about as well.[00:49:55] Nathan:Yeah, for sure. Is there a point in there where you saw things plateau at all? Like right. There was the, a flat part and an S-curve where you started to think, okay, I need to change something or push through this or anything like that, or has it always just been consistent?[00:50:10] Ali:Yeah. So I don’t really look at the numbers very much. the way that’s, you know, my, my theory of numbers has always been that like the, the numbers were, were always outside of my control. And the only thing that I could personally control were the number of videos I was putting out and how, how good I felt about the quality of those videos.That second one I got rid of very quickly, because I realized that what I feel about the quality of my own videos does not match at all what the audience feels about the quality of my videos. And therefore I’m not even gonna think about that. So the only metric I care about is just putting out two videos a week.The thing that I, I think of more. When it comes to, okay, these are, this is a bottleneck. We have to like push through. It is when the channel starts to feel like it’s a bit stale. And there’s been a few times, boy for four and a bit years now, or I felt like, okay, we’ve kind of been doing the same thing for awhile and it worked to get us here, but maybe what necessarily got us there.So most, you know, initially it was like medical school stuff or it’s that Kevin doing medical school stuff for a whole year. I need to kind of branch out from this. And it was like student stuff in general. And it was like, okay, I, I’m not, I’m not graduated to the student. There’s only so long. I can keep on just peddling the same stuff around how to be an effective student.It’s all kind of, of it. I mean, it’s, it’s obvious, but it’s, you know, there are a finite number of things. There’s like a few techniques that work really well and you make videos about them over and over again. So it, it feel stale now more, more recently, the productivity hustle lead type stuff has started to feel a bit stuck.And so now we’re now thinking, okay, what’s the next level? And that was what prompted the idea to start any podcasts that we’re what doing, trying to mimic basically the Tim Ferriss show or impact theory or school of greatness, or these other sorts of broadly in-person interview podcasts interviewing like entrepreneurs, CEOs, creators, and other inspiring people about how they find fulfillment in work and in life that’s like the spiel for it.And I, I, I hope that will be like the next level, and be able to expand our content beyond just me talking about productivity or me talking about tech.[00:52:06] Nathan:Right.[00:52:07] Ali:Mostly based on that gut feeling of stillness that I feel okay. The writing on the wall is that this is going to decline unless we change something rather than about the numbers.[00:52:15] Nathan:Yeah. That makes sense of figuring out. I mean, it’s in the quality of the product that you’re delivering, you know, and making sure that you’re continuing to innovate their innovative buzzword, but you know what I mean? so one other thing that I see you doing throughout all of this is making sure that it’s fun.And so I’m curious for your[00:52:33] Ali:Yep.[00:52:33] Nathan:On like, what’s your philosophy around making this fund? why is that important instead of just like, or in addition to the like rigorous discipline?[00:52:43] Ali:This is literally the thing that I’m writing a book about right now, which is that, you know, people have been asking me for it for years, how you said productive. Even when I was in like high school and university people would be like, oh my God, you do so much stuff. Like how, how are you so productive?How do you, how do you will have it? And it always felt a bit like, you know, people, people had this weird image of me that I was some kind of productivity guru. And now the comments on my videos, like, oh my God, he must be some sort of absolute machine. But you know, I, I, I, I line until like 11 o’clock in the morning this morning, the only thing that got me out of bed was a zoom meeting with the team.And I scroll Twitter for a solid, like 45 minutes today. And I wasted, you know, I, I finished up with a call about half an hour before we were meant to start recording. And I was like, ah, How much work are you ready to get done in half an hour at school, Twitter, often Ariba. So I’m just like genuinely really lazy.And all of the people who actually know me know that I’m really lazy and are completely baffled that the internet thinks I’m a productivity group. I think the, if there is one secret that secret is that I just make everything that I do really fun. and so I think that’s got kind of two components.The first component is finding things that you already find fun and then doing them. and that’s fine. it’s, it’s, it’s quite hard to do that because often the things we find fun are the things that are not really suitable for a career. Like, you know, I enjoy playing the guitar and do I ha I enjoy playing board games.I enjoy watching Netflix. Like it’s very hot. It’s hard to make a kind of sustainable career out of that probabilistically. Yes, I could become the next ninja, but it’s pretty unlikely I could become the next John Mayer was pretty fricking unlikely. and so the, the lever that I try and pull is figuring out ways to make the thing that I’m already doing, figuring out ways to make that more fun. And I think I’ve just sort of been subconsciously doing this for my whole life, because I don’t like doing stuff that’s boring. I only like doing stuff that’s fun. And I figured out like a few different, different things I can do that. Basically it tricks my brain into having more fun, which makes me more productive, but it also makes my life more happy.And it also means I don’t really need discipline because it’s like fun. Like, you know, when was the last time you needed motivation to hang out with your friends or discipline to sit down and watch Netflix is there. There’s not like really a thing. So that’s my whole philosophy on fun. If you optimize for fun, then, then the productivity takes care of itself.[00:54:49] Nathan:Is there an example of something that you knew you needed to do or wanted to do that you were able to make fun with? You know, this particular.[00:54:58] Ali:Yeah. the way I’m thinking about it. So it was as it was like, assembling something, the book proposal, I mean, that’s basically five, five categories of things. Conveniently, which, I kept on thinking like, how do I turn this into a five-part acronym? And then, one of my coaches, I just had them written down and he was like, do you realize that spells games like G a M E S?And I was like, oh my God, I didn’t see that. so it’s like G for gamification, a for autonomy, M for mastery, E for environment and S for social, and all five of those Oliver’s that I have pulled at various points with various things to make things more fun. so to give a concrete example, you know, when you’re going through medical school, you got to memorize just a shit ton of facts.Like it’s, you know, it’s, it’s a bit dry. Like some of this stuff is fun. Like human physiology is fun, but when you’re having to memorize, like the interactions of different drugs and like the mechanism of action of all this stuff, it becomes a lot less fun. And so the classic thing there is to figure out a way of turning it into a game.And if we look at all the research that video game designers have done about the things that make games. It is basically two things and that’s challenge and progress. And so if it’s gotta be sufficiently challenging, so as to feel interesting to get through, and I think the nice thing about like, studying for exams is that it’s challenging by default because, you know, you’re only going to really study stuff that you find difficult, but the progress is another big component of it.Like, you know, I was, I was addicted to world of Warcraft back in the day and I’d be doing so much grinding. and I’d be working really hard at world of Warcraft to kill, kill bores and skeletons and stuff. Just to see the XP bar taking along. I realized I could apply the XP bar to all of my exams and I just created a timetable and color coded it.So if I knew something, it was green. If I didn’t know it was red and you know, there would be graduations relations in the middle and there was something so satisfying about just watching the red boxes on my Google sheet, turn into green boxes that really sustained my motivation to keep going with it.And it genuinely felt like a game. and then, you know, that was, that was one. For that same stuff, you know, six years of struggling to memorize things, bringing friends on board, like studying with friends, we would, we would do the Pomodoro technique in the library together. We’d all be studying different things, but the fact that we were all in the same room doing, doing different stuff, but the fact that we were all in the same room and that everything was just more fun.Other things that make things more fun, autonomy. One of the biggest drivers of human motivation, when we feel like we’re doing things our own way, when we feel like we get to do something rather than we have to do something, just that mindset shift makes such a huge difference. And I use this a lot when I was at work.You know, I’d be getting to the end of, I thought that there was one time in particular where I got to the end of like a 13 hour long shift and the nurse said, oh, you know, this patient needs a, it needs an IV. cause they need fluids. I was like, oh God, I really can’t be bothered with this. I was in a bit of a Huff as I was getting all the equipment together.And then I re I remembered a blog post from Seth Goden, which was about this idea of have to versus get to. And I realized I was thinking of it as, oh, I have to put in this Ivy, like my autonomy was being taken away. I was being told what to do. This is annoying. I don’t want to. And I just decided to view it as I get to, I get to put in this county law and immediately, like, it was a, it was, it was magical.I was like, oh, you know, this is actually privileged. I get to do this. This is sick. This is so good. And then I, I put it in and had a nice chat. And I walked back home with like a spring in my step. And it was purely just that mindset shift that gave me a little bit more autonomy. and all the research around this shows that as well, that the more autonomy we have with whatever we’re doing, the more fun it becomes.[00:58:29] Nathan:Yeah, I love that. It made me think particularly what you said about the, the experience bar, right. And that increasing over time and wanting to see progress. I realized that my most productive time. Maybe in the hips, like my career as a writer. I don’t know, maybe even in my life who knows was this time that I was working on writing books and I use the app Scribner, to compile everything in the book.And there’s all sorts of things wrong with Scribner. And I don’t know that I would recommend it like as the thing that I use today, but across your entire document, which is really a collection of all these little things, it would count, keep track of your word, count across everything in the whole project file.And you would set a target, you could set a daily target, and then you could also set a, you know, your total. And I knew that the book I wanted to write would be like decent length, but not too long. So I was targeting 30,000 words. And so, yeah, I knew if I was going to end up at 30,000 words, I should probably write 40 and cut down to 30 or something like that.And so I was seeing that progress of every day I would up the daily goal and then watch them the, you know, the total goal and I chip away at it and I realized. Every time I’ve been successful at writing consistently has been when I have had in this case, an actual, like experience points bar, like going across and the times that I’ve had these habits going for a short amount of time and kept it going for a week or three weeks or something like that, and then dropped off is when I’ve been trying to do it of like, oh, I’m working in school, but I’m more forcing myself to do it.So yeah. I need gamification is what I’m saying.[01:00:09] Ali:Oh man. I completely forgot that. That I think that was how I first discovered your stuff. You’re like thousand days of writing or,[01:00:15] Nathan:Yeah. I did a thousand words a day for 600 days in a row. Yeah.[01:00:19] Ali:That was the one. Yeah. Oh yeah. I remember, I remember I came across a blog post where he talked about that and I was just like, so, so, so inspired.And I did it for about two days and then I stopped that. I was like, oh, I, you know, I keep on thinking, you know, often like showing or one of my other coaches will ask me, you know, what’s, what’s the one thing that you can do for you for the business that would move the needle. I can even think like, if I, if I could just write something, I could just write a thousand words a day that would genuinely move the needle for the business in so many different ways.I didn’t, I just don’t do it.[01:00:46] Nathan:Yeah.[01:00:46] Ali:You, got any tips. So progress bar check we’ll we’ll we’ll we’ll do[01:00:50] Nathan:Yeah. Well, I think the program progress bar, we’ll see a couple of weeks, the progress bar I think would be a big one. second thing would be, making sure that you’re writing the things that are actually highest leverage. You know, like we can write 500 words, a thousand words or whatever in a bunch of different places.I can write it over time in slack, you know, and in base camp posts of my team, I could write it on Twitter. but probably for me, the highest leverage place that I could write is for a book that I’m working on. Right. Because that will package up this material and put it out in a way that, you know, might reach tens of thousands of, or hundreds of thousands of new people.Right. There’s you can go on a book tour in life. Traditional media. Right. And go beyond CBS or something that if you didn’t have a book, they’d be like, why would we have this YouTuber on? But in the moment you have a book on this. So like, oh, you fit into our predefined paradigm. Like, you know, that kind of thing.Like James clear the newsletter author. They’re like not really interested in having him on, but James clear the book author they’re like absolutely like slot him right in.And so you think about right. he could write more content for the newsletter or he could write content for the book and that case, the book is higher leverage.So yeah, my, my things I think would be figuring out what’s highest leverage of where to put the words, and Y you know, what words to put down and then finding the ways to gain by it. And I feel a little bit weird giving the advice, because I’m in the position of being like, I need to do this as well.And so maybe that third thing is like all the people that you look up look up to[01:02:23] Ali:Yeah,[01:02:23] Nathan:Probably still, in some ways, struggle with the thing that they’re really well known for.[01:02:28] Ali:Yeah, yeah, definitely. Yeah. That makes so much sense. Like, I feel like people come to me for productivity advice, and yet I always struggle with productivity with, especially with writing the book, which is such like a long, a long term important, but not urgent projects.[01:02:42] Nathan:How do you think about, coaches? You you’ve mentioned, I think three different coaches, throughout this that you’ve worked with. So you’re, it sounds like you’re a big believer in, in hiring coaches and, and I’m curious as to how you think about it.[01:02:56] Ali:Oh, huge. I love, I love the coaches. I’ve only recently started. I think it was about a year ago where I decided that, oh my God, coaches are the best thing ever. yep. Yeah. People often ask me like, when, especially when the find out how much some of these coaches cost, it’s fricking expensive. It’s like, you know, like sometimes 300 an hour, $500,000 an hour.It’s like, what, how, how could you possibly pay 500 to a thousand Abdaalars an hour for someone’s time? It’s like, well, because it genuinely is usually is, is useful. I used to think of it as two things. And then I did really had a coach, like just before this, we were recording this where I decided to change it to a four, four part list of benefits of coaching.So the, the two original ones were number one having, I think, half of the value of having a coach. Isn’t just the fact that you show up and think about a thing for at least an hour. And you know, when I show up to a business coaching session, it’s an hour in the calendar where I. Doing technician working in the business staff.It’s, I’m doing big picture thinking of working on the business and the ROI on that is just absolutely huge. so actually just making the time to show up and secondly, and, and, and the fact that there is accountability in that I’m paying someone to be there. Someone is on the end of the zoom call. I will, therefore, I’m going to show up.I’m not going to not show up to the zoom call that I’m paying someone to be on and goes. That would, that would be weird. I think the second value that I, I got a lot from, it was, it was really a coach asks the right sorts of questions. And, you know, when I try and describe this to my mom, which is like, wait, why are you spending so much on a coach?Like, what do they even do? Like, do they even understand your business? It’s like, well, they, they don’t, they do, but they don’t really need to understand my business. They need to just understand businesses as a whole to know what questions to ask at what point. And it’s the fact that they’ve asked those questions that just is really, really useful, but that’s, it’s, it’s a very hard benefit to be able to sell to someone who hasn’t tried it.And then the other two that I figured out today that I’m going to talk about at some point are, think number one is confidence. so that like, if I, if I’ve made a decision about something and I’ve made it in isolation just by myself, I don’t have a lot of confidence in the decision because I don’t know what the hell I’m doing.I’m making stuff up as I go along. But if I’ve worked through that decision with a coach who is asking the right questions, and I trust them enough and they’ve got enough expertise in the area and I respect them, then I have more confidence in the decision because I know it’s been, it’s gone through someone who will have picked up some of the issues with it.And, and the final one I think is that I think it’s like the challenge in that, like, if I were to sit down and think about how to grow the business for an hour, that’s fine. You know, I w I would get to a certain level and it would be useful and I should do more. But when I’ve got a coach there and we’re thinking about how to grow the business, they challenged my thinking in ways that I might not have known to do myself.And so like, you know, for example, this, this session with Sean, where my default way of thinking is I have to hire a remote team just because that’s what everyone’s doing. and then he pushes back and be like, do you really need to hire remote team? That’s like, oh shit. You’re right. No, I don’t. And just having someone there to challenge my own thought processes is incredibly valuable as well.And so a bit like 100% of the coaches I’ve had have been absolutely worth their weight in gold. and so I’m just so bullish on recommending coaching to everyone, especially because most of these coaches have a money back guarantee, but if you don’t find it useful, you get your money back and that just[01:06:19] Nathan:Right.[01:06:20] Ali:De-risks the investment that it takes to get a coach.How about you? I’ve upskilled for a long time. I know you’re big into the coach thing as well.[01:06:27] Nathan:Yeah, I am as well. And so I hire executive coaches for my whole leadership team. So I’d probably spend 16 to $20,000 a month on coaching across my executive team. and yeah, he’s a believer in it. I think getting to the understanding of why you’re doing something right where you’re just like, oh, we’re doing this.And someone actually go, oh, but why? And you’re like, bright. Okay. Let’s dig in on that for a second, you know? Cause your, your answer wants to be well, obviously, and you’re like, but you haven’t actually articulated why that thing is true or why you would value it. what you said about like building out the decisions or.Like a real foundation for the decisions that you’ve made in isolation. I think it was a really good thing. Cause there are things that I instinctually say like, it should be this way or like, this is what we’re doing, but ISO, I simultaneously hold them very strongly of like, well obviously like here’s this thing.And so challenge them myself and think that they’re on shaky foundations because they haven’t been tested. And so a coach helps me close that gap of take this decision that I intuitively know is the right thing and bring it to the point where I can defend it and, and have a confidence behind it. and so it’s bringing that internal idea so that it can withstand the forces of, and I can express it with the confidence necessary for it to be like leading a 70% team or, you know, like making product strategy decisions for a company.And then I think the last thing would be. If you can find a coach, a lot of people do it specifically in like, let me hire a YouTube coach, a business coach, a writing coach, you know, for a specific skill. What I really like is finding a coach who has, like who will coach you on the emotional side, either do that, through that coach or like go to counseling.So like I find someone who bonds the gap between like the business coaching and counseling, or like do both separately because there’s so many things that we do of, how we show up how we lead, how we make decisions that are rooted in how we were raised or these little interactions, that if you don’t take the time to like suss them out you’ll for better or worse suffer the consequences of them for years without actually understanding that that’s what’s driving it.So that’s why like reboot, that organization, because they like play that middle ground really well. Being totally willing to, or like eager to dig into your childhood, to like, get to this like $10 million like business strategy decision and why you’re trying to choose one or the other.[01:09:15] Ali:Hey, have you got an example of kind of where you felt like a childhood emotionally type thing changed a decision that you were, you were going to make?[01:09:24] Nathan:Well, I was going to make a reaction decision to one of my executives, and they were going to, and it was because I felt like they were taking advantage of the resources in the business, which on one hand, you’re like, well, they, they should, right? It’s one framing is taking advantage of it. The other is like, here’s a multimillion Abdaalar budget.Like go spend it to grow the business, right? They’re not taking advantage of that budget. They’re putting it to great use, you know? And so being able to dig into like times in my childhood where I felt like I had been generous and that had been taken advantage of. So, I had an executive who was intellectually making the right decisions to grow the business.I was having an emotional response to it and rather trying to logic my way through, like, here’s why you shouldn’t have that emotional response. It was much more helpful to dig in and understand why I had that response and where it was coming from. What was it that was triggering and like, actually really dive in and sit with that rather than like, you know, being like Nathan that’s irrational don’t don’t respond that way.[01:10:31] Ali:That’s interesting.Yeah. I feel like I must have a lot of blind spots around this stuff. I’m actually starting therapy from this Friday. It should be fun.[01:10:39] Nathan:Oh, I’m I’m like the biggest fan of therapy and recommend it.[01:10:43] Ali:Oh, nice. Yeah. I mean, I’ve heard so many people like, like internet friends say that as well. Like I feel like I don’t have anything specific that we need to work through.[01:10:52] Nathan:Yeah.[01:10:53] Ali:Have any mental, I like, you know, clinically diagnosed mental health conditions, but it’s just one of those things where I feel like it’s so it’s so ROI positive[01:11:01] Nathan:Right.When it’s what you call that I’m spending an hour like methodically, you know, like taking a step back and looking at your business instead of working in it, like, what if you did the same thing of like taking a step back and analyzing yourself and why you react that way and what that’s based on and, and all of that.And if you do that every couple of weeks or months a month, like the ROI is, is substantial.So, yeah. we should probably wrap up there, like I’m realizing I have other things that I should get to, but we could talk about forever basically, but this has been fun to dive in. you have a ton of things going on on the internet.Where should people go to subscribe to the YouTube channel? The newsletter I follow you on Twitter, all the things.[01:11:49] Ali:Yeah. So probably my website is the easiest place, so, www.aliabdaal.com. There you’ll find a link to the newsletter, which is hosted on ConvertKit, and you’ll find links to the YouTube channel or Twitter, and everything else from there as well. But yeah, thanks for having me on Nathan.[01:12:02] Nathan:Yeah. Thanks for coming on. I’ll catch you later,[01:12:04] Ali:See you later.

Matt Ragland is a productivity expert and full-time content creator. He has worked for companies such as AppSumo.com, ConvertKit, and Podia. Matt graduated from the University of Florida with a bachelor’s degree in recreation & tourism management.Matt was one of the earliest members of the team at ConvertKit, where he was employee number five. Since leaving ConvertKit to start his own company, he now hosts a podcast, publishes a newsletter, has created several courses, and hosts his own YouTube channel.Matt prides himself on being a skilled manager and enjoys helping his clients and audience grow and develop their agencies. He is also the proud father of two boys and is a fitness enthusiast. Matt and his family live in Nashville, Tennessee.In this episode, you’ll learn: Matt’s biggest revenue drivers as a content creator How to know when it’s time to take your side hustle full-time How to optimize your YouTube channel and content Links & Resources Podia Ryan Delk Bryan Harris James Clear Sean McCabe Sean McCabe Levi Allen Casey Neistat Tim Ferriss Jeff Goins Ali Abdaal Marques Brownlee Roberto Blake heycreator.com Matt Ragland’s Links Follow Matt on Twitter Watch Matt on YouTube Matt’s website Matt's newsletter Episode TranscriptMatt: [00:00:00]If you’re not sure if you want to do something, try it 10 times, and really give it a good try. Write 10 newsletters. Make 10 videos on YouTube. Record 10 podcasts. I have found that going from 10 to a hundred is definitely a slog, and there are lots of mini milestones, but once you do something a hundred times, you’re going to build momentum on it.And you’re also going to build your own country.Nathan: [00:00:30]In this episode I talk to my long-time friend, Matt Ragland. So Matt joined ConvertKit really in the early days. He was employee number five, and he was here for the crazy ride. Then he started a YouTube channel. He led the customer experience team at another startup called Podia. He’s now as a full-time independent creator earning a living on his own.We have a really fun conversation reminiscing about the early days talking about crazy rocket ship growth, and how we kept up. We get into earning a living as a creator. How he grew his YouTube channel to 60,000 subscribers. How to choose a niche, and when you should double down on that, and what’s getting traction on YouTube.The last thing that we talk about is when, as a creator, you should quit your full-time job, and some of the nuances of that, so you can go full-time on your creative endeavor. So it’s a longer episode today because Matt and I just can’t help but tell stories.With that, let me get out of the way and dive in.Matt, thanks for joining me.Matt: [00:01:31]Oh, it’s such a pleasure. I’m thrilled to be here.Nathan: [00:01:34]I want to go back to, what year would it even be?Matt: [00:01:40]2015.Nathan: [00:01:41]2015? Okay.Matt: [00:01:44]Right around this time. Maybe a couple months later, but it was like late summer.Nathan: [00:01:49]So, it’s July, like yeah. And then July right now. Yeah, it would have been when we started talking, I’m thinking, what were you doing online around that time? Cause I started to come across you on Twitter.I think Brian Delk was a mutual friend.Is that right?Matt: [00:02:06]Yeah. Ryan Delk was a mutual friend. Brian Harris was a mutual friend. The way that we got actually directly connected is that I was on Brian’s email list. And I saw that you were doing a webinar with him to promote ConvertKit. And I had just signed up for ConvertKit as a customer, always like a little notch in the cap that I, I feel like I have of having like the three-digit user ID.Nathan: [00:02:32]Do you remember what your user ID is?Matt: [00:02:33]I used to know.Nathan: [00:02:36]In the three digits is pretty impressive.Matt: [00:02:38]Yeah. A three digit. Yeah, definitely.Nathan: [00:02:41]Now they’re well into the six digits.Matt: [00:02:43]Yeah, it’s wild. And so, I was familiar with ConvertKit. Certainly at that time it was like, okay, let me watch Nathan talk about it. What are the things that he thinks are important with it? Like some email building strategies? Because what I was really doing a lot of my online work at that time is I was doing two things.I was doing some contract work with some other SaaS companies. In terms of an audience building creator standpoint, I was doing two things. One was that I was creating the sketch notes. And so like visual, visual art of like webinars, podcasts. And that’s what I would use to teach people how to take better notes so they could remember more of what they’re doing.And it was a way to connect with other influencers because it was an attention grabbing thing. And so that was the main thing in terms of audience building and some course creation.The other thing that I was doing that paid the bills a little bit better at that time was I was also helping people set up WordPress themes and websites.At the time I would be like, oh yeah, you know, I kind of do some web development and then like, not really knowing like what all that meant. And then as I started to work more and more with actual developers, I would set up a theme online for people. But you also look at it and see that there’s still a pretty interesting intersection between like, how can you just do something relatively simple for people that either: A, they don’t have time to do, or B, they just don’t want to figure out because they just want to focus on their creative work.And so that’s what I was doing summer 2015 at the time.Nathan: [00:04:27]Yeah. So then at the time we were, I think four people, five people on the, let me count,Matt: [00:04:37]I think it was four if I remember properly,Nathan: [00:04:39]Myself, mark, David, Dan.Four. Yeah. and we were at 15,000 a month in revenue. Let’s see now I’m trying to think.Pat Flynn had just signed up in the month of July. We’d gone from 10,000 a month to 15,000 a month, 50% growth in a single month. And that’s really when the slow grind turned into, like, I started turning the corner into how are we ever going to keep up, which is where you come in with the story.But, so basically in July, Pat Flynn and then Wellness Mama, and another popular blog all signed up at the same time. And so MRR jumped, you know, we had these bigger customers that were migrating and switching over, but then as it got into August, September, they all started talking about it.And then when we went from 15,000 a month to 22,000 to maybe 35, then 50, then 80, then a hundred, like it just, in six months it went completely wild.Matt: [00:05:46]Yeah. Certainly, you know, obviously remember that. And so I was, I was brought in to help with some support initially, just to help Dan out with some support and use, you were certainly doing a ton of that at the time. And I also, roofer, I think it was the first ended up being for the first two years I was at ConvertKit.I worked on migrations for the most part. So those, you know, bigger people that were coming in, I was helping them get set up. And the other thing that I did, so I kind of had like three phases. I would do like the migrations and then I would help out out support as much as I could. And then I would also do, because not just like migrations at that point were, you know, for the, for the larger customers that we still had, like so many people signing up every single day.And so I was doing like a weekly or every other week at the most like here’s how to get started workshop and just like doing that. Really like, here’s how you set up your account. Make sure you do this. Here’s the form. How’s how you get the form on your site. If you don’t want to get the form on your side, you can actually still like, you know, we had a few landing pages at the time, nothing like, you know, the lovely, lovely template library that exists now,Nathan: [00:06:56]I think by a few, you literally mean for,Matt: [00:06:59]I really, yeah. Not just like a few dozen, like literally three or four. Yeah.Nathan: [00:07:05]So when you came on, right. Cause we brought you on part-time I remember being totally overwhelmed. you and I were talking later, about like starting part-time and then gradually increasing hours. I wonder if you would share like what that was like for you, because I think there was some confusion as to like why we were ramping up your hours gradually or other things likeMatt: [00:07:27]Yeah, I think, you know, I think I understood it initially. And is there was kind of like this, there was another, SAS company that I was contracting with at the time, and I was just more excited about convert kid. And so I don’t know if it was confusion as much as like, I just wanted to like go all in on what convert kid was doing.And so like maybe not confusion, but just like, I was really chomping at the bit to just like, totally focus on it and not just like step away and be like, okay, I guess, you know, kind of hit my hourly. There’s still things to do, obviously. But it became pretty clear after like, I think just three or four weeks that was like, okay.Yeah. It’s it’s time.Nathan: [00:08:09]Yeah. And we were increasing your hours directly in proportion to the MRR at the company.Like we wanted more time from Matt, but, like needed more MRR. And the nice thing, was that MRR was coming in like week over week in a meaningful way. Whereas the previous years it had been a slow journey.Matt: [00:08:31]I know you’ve talked about this, you know, certainly a lot since, and ConvertKits rolled out the free plan over the last 18 months, but, you know, it was a pretty controversial thing, like in terms of building a SAS company and one that was bootstrapped that I, you know, I felt that it was, there was always a paid plan.Like there is a bit of a free-trial, but it was always paid. And so like,Nathan: [00:08:53]I think Ben, it was actually just paid from day one.Matt: [00:08:55]Yeah, you’re right. we didn’t even do the free trial. And so, like, you just knew that like, you know, certainly people would kind of turn out after 30 days if they didn’t like it, blah, blah, blah. But we knew that there was money coming in more reliably because when people sign up or like, okay, you know, we can kind of project that. Even people that tranquility quickly, like we’re still gonna have like this expected amount of LTV for the person.And we can, you know, at least forecast a little bit better that way. And so, like I thought that was, again, again, in retrospect, like really nice and probably really helpful, even if you’re like, you know, and again, at the time we, you know, being bootstrapped, like you still are, that there’s a, like you almost, I don’t know.I wonder how you would think about this. Like, there’s almost like this veil of like, how much can we handle given the people that we have and like, where is that? I remember like, feeling like we were riding that line for, you know, not just months but years.Nathan: [00:09:54]Right. No, I, I think certainly, yeah, at least a year and a half of, just things moving so quickly and like at the times, so you joined in, I don’t, I don’t even know like an exact date, but call it that like August, July, August timeframe, something like, that.Matt: [00:10:17]Yeah, September, I think it was like September, October around that. I always, we were talking about this pre-show but I always remember that it was right around, this is my bin. This is my like timestamp that whenever pat released his I’m switching to ConvertKit. So you can go look at the timestamp on that post.It was right around that time. So whatever that is, it was like, that’s when I started like, yeah. Yeah. Obviously things started taking off a lot of that.Nathan: [00:10:43]Yeah. That post was amazing. And the, and the title even, was it like a masterclass in positioning and all of that? Cause it was titled why switched from a Webber to infusion soft to convert it?Which the reason like you’re like, okay, that’s a long story in a title. but the reason that was so important is because everyone at the time, like a Weber and MailChimp were the most common, but in like the blogger space, people who’ve been around for awhile, a wherever was even like like just as common as, as MailChimp.Matt: [00:11:17]Oh Yeah, Yeah, definitely.Nathan: [00:11:19]Then when you graduated from one of those tools, you went to Infusionsoft, everybody did.And so if Pat had written the article of why I switched from a Webber to ConvertKit, people would be like, oh, but You never tried Infusionsoft.Like, and so there’s a third act to this where you go like convert it, you know, you’ve outgrown ConvertKit and now you’ll go to, if you just offer something.And so by having that in there, it was, you know, it just told the whole story and peopleMatt: [00:11:43]Right.Nathan: [00:11:44]Was like, wait, whatMatt: [00:11:45]You already tried Infusionsoft. That’s what all the big names use pat, you’re a big name. What are you doing?Nathan: [00:11:53]When I remember him being on mere cat Periscope, one of the two, like in live streams, like late at night, because pat likes to work at 10 or 11 at night And people would be like, wait, what email service are you using? Cause he’d like drop hints or, you know, something like that. And then there’d be like 50 or a hundred people commenting. like what are you using? I’m thinking about, switching to it or whatever. So it was a remarkable time.Matt: [00:12:16]It was his, Yeah,And I mean, who knows what the future holds, but like, that was definitely like the most like fast paced, interesting like seat of the pants, you know, like ride that I’ve been on.Nathan: [00:12:32]Yeah, we’ll give a talk about rocket ship.It was that.So let’s see. Maybe if we fast forward a little bit, actually maybe talking about that moment, right? Cause we went from, when you joined, we didn’t even have, like an LLC. We didn’t have payroll. We didn’t have anything because that is cause Ashley joined in November. And the first thing that she did was set up like, a companyMatt: [00:12:57]You were paying me through PayPal.Nathan: [00:12:59]That’s right. Yeah. And so then she went through and set up like the company and taxes and payroll and health benefits.Matt: [00:13:07]Yeah.Nathan: [00:13:08]What were some other things from the early days? Like, I dunno, favorite memories or, stories of, of, that.Matt: [00:13:13]There was, I’ve been wracking my brain trying to remember it, but there’s something that now I, you know, I really wish that I had found it if I do, but there’s something that happened like around. I want to say, like January of that year, there was something with an account That we just all found like unnecessarily hilarious.And it was like some kind of ponder play on words that I, I, again, it’s a terrible story because I can’t, this is a terrible story right now because I can’t remember it, but there’s something in my heart and in my subconscious that I just hold so dearly, but not like closely enough, apparently there is, there are just so many moments like that and, you know, having that first, well, I kind of cheated a little bit because a bunch of us went to WDS in summer 2016 and that was the first time we all got to hang out together.And that was like really awesome and special. And then like two or three months after that was when we had our first retreat and those retreats, you know, still like, I saw, you know, Haley Jane a sec, yesterday here in Nashville. And we were talking about like the Oceanside retreats and just being able.And I always like thought. ConvertKit was like at the forefront of a lot of things, but like really making the retreats meaningful and special. And, also doing them twice a year. The thought was, you know, still think is really cool. Obviously we’re in an odd time for that right now. But to be able to like see the people and like work with them in person, those are all like some of my, some of my best memories from working at the company, like even outside of like the actual rocket ship of like growth that we all went on and just having those, having, I still, like one of the coolest things, like for me is still like having connections and strong relationships with people at the company.Even now that I haven’t like worked there. Gosh, I guess a little over two years now, like to be on your podcast, to like, have Haley text me and say like, Hey, I’m in Nashville, let’s meet up. Like those, like, it’s, it sounds like kind of trite to say, but it’s like, it’s the people, it’s the zoom calls. It’s the stand-ups that were fun.And the other thing that like, all kind of ended on is something that I’ve always kind of taken away that I think is so fun is I remember like our Monday stand-ups or Monday meetings and just how out of control the zoom chat would get, like, it would completely derail meetings. you know, it probably still does, you know, you set a high, a high standard, but like, I’ve now been like, I’ve been at podium in it.Like I’ve been on like other, like companies, zoom calls and, or just like, you know, groups that I’m a part of and all like trying to get the chat start and people are like, what are you doing?Like you’re ruining The meeting. I’m like,Nathan: [00:16:10]Yeah. The peopleMatt: [00:16:11]Nope. Yeah. I guess I am ruining the meeting. If you all, aren’t going to play along and like, you know, talk trash inside of the chat.I guess I’m ruining the meeting, but those, I still like, obviously think about it and just can’t help, but like laugh about it.Nathan: [00:16:28]There was a meeting.I’m trying to think who it was. We had Derek on the marketing team. I don’t know if that’s been three years or more ago, had brought in some like growth expert. It might’ve even been like Sean Ellis or someone who like really knows even just like pinnacle of growth marketing. And he’s like talking to the group and I’m there and it’s just like, it’s, it’s our crew, you know?And so I’m dropping like jokes and random things in the zoom chat.And of course he didn’t see it in real time, you know? Cause he’s like presenting and, he’s like, just so confused because normal companies don’t do that. So it’s like, the most converted thing that no one on the outside would knowMatt: [00:17:16]Yeah.Nathan: [00:17:17]Troll our zoom chats constantly.And it’s so fun.Matt: [00:17:20]Yeah, it was definitely Sean, because we had just signed up for the growth hacker software and we’re using it to run our growth tests. And when you sign up for an annual plan, we had done like some little extra special thing and, or like, you can have an hour with Sean. We’re like, yes.Like if you want, we’re like, yes, we’ll put it, you know, put it on our tab. We’ll grab an hour with Sean. And I do remember that. He was like, oh, it looks like there’s a question. Oh, there’s not a question in the chat. What is going on? Do you, do you want to say something? We’re all like, Nope, sorry, wait, nevermind. We’ll do it anymore. I just, you know, of course couldn’t help ourselves. Then he was like, oh, you’re doing that in the chat again. Like, Okay.Yep.Right.Nathan: [00:17:59]Yeah. That’s just, That’s just, how we are. there was another time that I’m curious for your take on. So, cause we, like, if we fast forward a little bit, we were, you know, trying to keep up with the crazy growth. so w like go to January and we’re like a hundred K MRR. I mean, at this point we’ve expanded the team quite a bit.Right. Nicole, Ashley,Matt: [00:18:25]Yeah. Darryl Blake, Danny.Nathan: [00:18:28]Danny and, and others were, were a bitMatt: [00:18:30]I get, yeah, thoseNathan: [00:18:31]But like Brad Knoll, you know, more on the engineering side, just across the board. So the team’s gone from like, you know, four to 11, like really quickly, and just, we’re trying to keep up, like, keep the servers on, keep the support ticket it’s going and all of that.But we made this move to try to get profit. from, I think it was probably February until like that February til July, I think. And we went from 3% profit margins to 50% profit margins, all through growth. like, we didn’t cut expenses.Be growing 15 to 25% a month, you know, but I’m curious what that was like from your side of what, you know, like, when I came in and said like Hey, we’re gonna, we’re going to do this and we’re gonna try to pull it off.Is it like, oh, this is going to be a death March? Or is this like, oh, we’re all in it together. like we’ll see how it goes.Matt: [00:19:24]I think, that at that point, and I felt like me, especially, but at that point, like we were all like that kind of classic start-up line of like, we were all like young and dumb enough to think that we could pull it off. And because like I had had a front row seat of going from like 500 to 3000 users in a few months and like all that, all of that growth, cause especially like initially for me and part of this actually.A bigger interest in like understanding more of the financials behind like startups. And because like, when you first said that, I was like, okay, well, I don’t really know how we’re going to, how that all works, but that’s not my job, you know, that’s Ashley’s job. And I trust her and, you know, Nathan will figure it out too.So, but cause I tended for a long time to think of our growth. It’s funny, you know, you obviously keep mentioning the revenue growth. Like I would just think of it as like month over month user growth as well. Cause like I just saw them like in the chat forever. And so I remember like just that all of us had either op he said, we wouldn’t, you went from four to 11 or 12 really quickly.And so all of us were like so fresh and Fired Up that we’re like, great. I mean, look what just happened in the last three months. Of course, you know, we can do this in the next, in the next six. So. I remember being like, fired up about it because like, it was that kind of classic. I didn’t know any better at theNathan: [00:20:55]Right. Yeah. If we were all, we were also, you know, I was looking back at like salaries from those days and like the 40, 50, $60,000 a year salary is that like, we can not like no one would take that today. but then it was just like, we’re all doing this thing. And you know, it’s pretty amazing to seesomeone who was like, started at Ken Birkin on to $40,000 a year salary, like five, five years ago is now making like one 20 plus a bunch of profit sharing or other things it’s like, okay, there we go.Like the bet that they made did actually payMatt: [00:21:30]Yeah, absolutely.Nathan: [00:21:35]It was tough going for awhile.Matt: [00:21:36]Yeah, And it’s been a really cool thing, like even, and this comes like from the transparency, like I’ve consulted with some other. Companies over the last six months and I’ve used ConvertKit as a, reference point so many times because of the transparency, I was like, well, I mean, you can go look at what, you know, they’re like, what do you think the like, numbers are for somebody?This is like, I don’t have to wonder you just go look at what, you know, ConvertKit’s numbers.I can tell you that it’s this, this, this, like, how do you know that it’s like, just go to convert, get.parametric.com. So it’s all right there. You can find your numbers. It’s all right.And so, like, I, you know, remember thinking that like, again, like this is where, like my dormant, like love of again, statistics and financials and all of that.Can I came, came back to life for, for me. And it was just a, it was just amazing to see like that first. And it wasn’t, it was more than just the first year also. Like it just kind of kept going and again, it’s just a really, it’s a really unique experience. Yeah. I’ll obviously never forget.Nathan: [00:22:44]Yeah. Well, you mentioned retreats earlier, and I have a favorite moment at a retreat. I think it was, probably would have been our third retreat cause we were up in, up in McCall, outside of Boise.And it was you starting like making a first YouTube video with Charlie or did you do thatMatt: [00:23:03]That was an ocean side, actually. That was an ocean side.Nathan: [00:23:05]What was it that you were doing in McCall? When were you entirely just talking about YouTube?Matt: [00:23:10]Yeah, we were doing a collab at that point as the YouTubers say. Yeah, just talking about like productivity and planning. How she plans her day, how I plan mine. Cause she’s, you know, Charlie, just as a quick aside, like just an amazing person, greater friend, like she helped me so much. They get my YouTube channel started. Like I, again, she’s wonderful. But to like sit down the day that we’re supposed to, this is an ocean side we’re supposed to like leave and two hours, everybody’s like trying to pack. I don’t know how ready she was to leave. Maybe she was already, but she was like, Hey, you know, Matt let’s do a video for your YouTube channel.I was like the one that I haven’t started yet. And she’s like, yes, we’re doing a video. And it was just, you know, it was six, seven minutes. And for her to sit down, I think she was around like 70 K subscribers at that time to like, kind of, I was like, I had known Charlie for a while at that time. And we were pretty close, but I was like still nervous.And then like Mark’s walking through the back of the frame. Picking stuff up gathering like, you know, paraphernalia it’s I don’t know if that’s the right word to use. Just stuff was a terrible word, terrible word, choice thing. Trash we’re good people we’re picking up. Yeah. After ourselves. And so it was just like this really funny moment.And I try not to talk too much about YouTube cause I know we’re going to get into it. But like that video still only has like maybe 500 views is people think that when your YouTube channel gets big, like all of your videos take off. And the majority of my first 50 videos are still like, well, under a thousand views. And it’s it is this like kind of it’s like compounding interest. It’s like, you know, compounding, like, you know, user growth that it just kinda builds on top of itself. It creates this like self, you know, like when people come to your channel, even if it hasn’t taken off yet and people see. Okay. This person is serious.He has 30 videos. It’s not like he threw a couple up there, like people know that you’re in it. And so I can tell you what I thought you were going to say.I think it was the second McCall retreat. And so we go up to this lodge and it’s right by, you know, beautiful lake in, even in August, quite chilly and so swimming around.And, our coworker, Nicole has these like prescription sunglasses, fancy, expensive, nice. Just like Nicole. And they fell off in the lake, not super deep, but like, we swam around trying to find these things for like 20 minutes at the end of the day, we’re like, okay, we got to go back.It’s dinner time. It’s getting. And so the next morning I’ll say like, I like cold water, which is a whole nother like conversation, but I like cold water. I also like particularly cold mountain water in the morning, like so brisk, so nice. And so I was like, okay, well, am I do this anyway, I’m going to find those damn glasses. And so over there I swim around because my other theory was like, okay, we kicked up a lot of like gunk at the bottom.It’s going to settle. No, one’s out there yet. I’m going to find them.And INathan: [00:26:26]The other thing is you had this this time,Matt: [00:26:28]I did have goggles thisNathan: [00:26:29]Because I remember I was like first thing in the morning or, or maybe it was at night. I can’t remember, but like,Matt: [00:26:37]In the morning.Definitely.Nathan: [00:26:38]Like all of this, stuff on the table randomly, can you come in And you’re like, and see a pair of goggles sitting there. You’re like did we have these Ulta?And was like, know,Matt: [00:26:47]We had goggles the whole time.Yeah.Nathan: [00:26:52]You find those. And then, I don’t know, like minutes later, you’re in the lake. Yeah.Matt: [00:26:56]Yeah.And so pull, pull those out and was a great, was a great moment. Like the, to return those.Nathan: [00:27:03]Nicole wakes up late hours later, you know? Cause you’re up early swimming, like, and thenshe has her like hundreds of dollars prescription sunglasses back. That was actually the very first retreat That wasMatt: [00:27:14]For street.Yeah.Oh man. Good times.Nathan: [00:27:18]Like getting, I mean, we were 20 people at the time getting that group together for the first time was those are just special moments in a company.Matt: [00:27:27]Yeah. absolutely.Nathan: [00:27:29]Okay. So would it be the next retreat then? That was Oceanside. When you did the YouTube video with Charlie or was it a year? Four year.Matt: [00:27:36]Yeah. That would have been the next, that would have been the Oceanside retreat. That would have been probably the first ocean side retreat, because it was February, 2017 that I started my YouTube channel and DV a little background. Like I had done blogging for a little while. I had like tried some service work, like I already mentioned. I had done 30 interviews on a podcast back in like 2014 when we first moved to Nashville. And that was actually one of the ways that I met Ryan Delk because Brenda elk was on the podcast.Crazy looking back the, the two, the other person that I got on the show, I don’t even know how, even then was James clear, a mutual friend, James clear was on the show and now he’s like James clear in 2014. No big deal is like, he was still talking about passive Panda. That’s right. Matt Ragland interview that now even Matt can’t find anywhere. And so you’re welcome James, if you’re listening to this.And so I’d done a bunch of different things online, and I would say that while I did build my creative chops and confidence through all those things, I hadn’t really stuck with one thing long enough to see. Like again, that compounding growth that comes from just being consistent and showing up. and again, mutual friend, Sean McCabe talks about showing up every day for two years. And, so what I did is I decided in February I was going to post a video every day. I was gonna do 28 videos and in February, so a little, little fun, cheating them,Nathan: [00:29:13]I liked thatMatt: [00:29:15]Yeah, that’s right. That’s right.Nathan: [00:29:19]10% easier.Matt: [00:29:20]That’s right. And so I did that and I just, I got more used to it and I didn’t take off, like, I’ve talked with Darryl, we’ve mentioned derelict at times, like Darryl and I have talked about this, but like the channel did not take off. And I ended up making after Daily is, is quite the grind.I just, you know, I couldn’t keep that up, but I was doing still weekly videos through the rest of the year. Yeah. Then, it was the other thing that is just wonderful about creating a body of work is that then you have a, you know, a much clearer data set to look at, to understand the, these are the topics.These are the type of videos that took off more for me, you know, if you just make a handful of videos and you see one is a little bit better than another, that’s not a good enough sample size, but at the end of the year in December, I’m looking back and I’ve created like 50, 60 videos at this point. And I pinpoint like, what is the most popular, like as I’m going into new year?What, how can I kind of maybe narrow down my niche a little bit more and be more focused? And I saw that my most popular video of the year is one that I had released in August where I talked about how I planned my week with the bullet journal. And I’d been using the bullet journal method for a couple of years at this point.And. So I was like, well, you know, new year’s coming up, I’m going to like create this video. Here’s how I’m playing my year and a bullet journal. And at the time, like, I felt good about it actually like, Levi Allen, who’s great. You know, YouTube and creator, graphing commerce speaker, Casey Neistat friend.He helped me with the thumbnail. I like sent him a bunch of, and so we really dialed in the thumbnail and that video is like, I think it was at like 600 ish subscribers at the time. And I hadn’t had a single video go over a thousand views as like, I hope this video is the one that goes over a thousand views and it would also be cool if eventually it helped me get to a thousand subscribers because you got to remember, I’ve been doing this 11 months and had 600 subscribers.So I’m like, you know, maybe in like another six months I can get there and I released the video and it started to take off. Like, especially for me, but then I was really like, oh, this is like taking off for like any kind of YouTube video.It has a thousand views in the first day.And then you’re definitely within the first two days. And then I had a thousand subscribers by the end of the first week, I was like, oh, okay. Interesting. But again, I was able to see that like big picture data to like pinpoint that particular type of video too. And again, it was a good time time of the year, literally to be talking about productivity and planning.I’ve seen that like over and over again in the year, since, as I’ve narrowed down on this niche. and then the way that I create and I tell creators this all the time now, is that when you see something that hits like find the, like, especially if it’s like a bigger video, like I had, this was like 20 minutes.It kind of like didn’t fit the normal, like YouTube things. But I talked about a lot of different elements. Of productivity in that video. And so my next four videos were basically like taking these different, like components that I had crammed into a big overview video and said, like, here’s how I blocked my time.Here’s how I manage my tasks. Here’s how I like plan out my week. So we take like something that’s big on the macro side of saying like, here’s how I plan a year. You start to plan a quarter here, the months they go into that. And then like the weeks they go into the months. So I spent like my next six videos, just basically breaking down the individual aspects of that first video.And then it was just like off to the races at that point.Nathan: [00:33:07]Yeah, that’s fascinating to me. What have you found about LinkedIn videos Cause I’d be like, oh, it needs to be a shorter video. AndMatt: [00:33:14]Right?Nathan: [00:33:15]The truth of the matter is yeah, just get into an online.Matt: [00:33:19]For me, I have found that my, with one exception. My longer videos traditionally have performed better because there is this interesting, like there is this interesting dichotomy of like statistics on YouTube is that they want a high retention time. But if you can kind of like overrule that with a long view time, then it like still works the same way.So like a video that I create that’s 20 minutes. If someone was like, you want to be over 50% video, like time retention. But if you’re talking about it’s a 20 minute video and someone watches for nine minutes, well, like I’ve seen and you do has been changing a lot, I think. But I’ve seen that if you keep someone on YouTube for nine minutes, they’d almost kind of rather you have.A lower like overall retention, if you can keep them on there longer than normal. So like for example, you know, the difference would be like, if I have a five minute video with 60% of it, you know, 60% view retention, but then that’s only like three minutes watched versus 40% view retention, but it’s eight or nine minutes watched.Like those, those have tended to perform better for me. However, I have been working on lately, like more this year, trying to be more concise with my video and with my takeaway and my talking points. And so I’ve been trying to be like under 10 minutes for most videos at this point, that’s where I’ve kind of found a sweet spot and even experimenting with some sub five minute videos that is just like, literally.Here is one tip. I’m not stacking like additional concepts on top of each other. It’s kind of the equivalent of like, just doing like that 500 words a day, like maybe a thousand words a day. You’re just trying to get that. Like, you’re trying to get that five minute, like blitz out without like trying to expend a bunch of time, like trying to like get the perfect 12 minute video or 3000 word blog post.Nathan: [00:35:36]Yeah, that makes sense. So in that journey from breaking the thousand subscribers to now, you’re about to break 60,000 subscribers. what are some of the things like if you were, if I was like, and you know, Matt, I’m going to start a YouTube channel today, or I have one that has like you know, maybe I’ve shown that I can like show up consistently andMatt: [00:35:55]Right.Nathan: [00:35:56]That, that ability. but what are the things like the, the tips and lessons that you’ve learned along the way.Matt: [00:36:02]The biggest ones are to just continue being consistent. I think I could have like actually been, have grown even faster than I did if I had been even a little bit more consistent. Like I think two videos a week is really great, even though, you know, full disclosure and you can go look at my YouTube channel.I have struggled to do like two videos a week consistently, but that is also because like, I have a bunch of other creative interests that all fuel each other. And we’ll talk about those, but if you’re just talking about like growth on YouTube, then it really is the consistency that will help you win the day and grow your channel.The other thing is that as much as we want to as creators, let the work stand for itself and like be a great overall piece of content.On, you know, on YouTube, the title and the thumbnail are equivalent, like to your, like, for those of us that like kind of grew up blogging a little bit more like the headline, or like with email newsletter in the subject line, like that is the YouTube equivalent and it is so, so, so important.And so, you know, YouTube gets kind of a bad rap sometimes for like the clickbaiting this, and that’s definitely a thing, but it’s, again, people have said that about subject lines and blog headlines for years, but that is really, really important. And if you don’t grab someone’s interest in like these three phases of the title, the thumbnail, and then like, literally what is your opening line?Because YouTube will show that those are the biggest things. And I think that like the amount of time that you should spend on that kind of changes based on what phase of YouTube and just content creation in general.Because if you’re talking about like, okay, I want to go from five to 10 or 10 to 20, I would still probably argue that you should like focus on.And depending on, you know, what your time is, like, you should focus more on the consistent output than like really worrying about trying to over-optimize every little piece. And there are good ways about that in there, like tough ways about this. But I would basically say like, I would rather use, I would rather see you put out four video, like a weekly video than just one monthly video that you feel like, oh, this is, this is the one, this is, this is it.I spent so much time on editing and the sound is perfect and all the transitions are smooth and all, you know, the, the thumbnail just looks so good and I got the title dial.Because you can believe all that, but like the market ultimately decides like the viewer ultimately decides how much they really care about that as well.And the other thing that is kind of tough, like I think mentally for creators is, and I’ve, I’ve done this a ton of times is when you feel like, oh, I, I made this as perfect as I can. I feel so good about this. And then it just bombs. And you’re like, what the hell? Now? I feel less confident. I’m less excited about the next one.Cause if I put so much effort into this video and it didn’t work or this newsletter, this course, and it didn’t work out, what, like, what does that mean? And you get into all these like existential creator questions bouncing around in your head.Nathan: [00:39:18]I, yes, there’s a lot of that.So it sounds like you’re saying optimize for like number of shots on goal, rather than like the highest probability shot and optimize it, like yeah.Quantity over Quantity and continue optimization over likeMatt: [00:39:35]Right,Nathan: [00:39:36]The clinical of the perfect videoMatt: [00:39:38]Right.Nathan: [00:39:38]Putting. All of it. IMatt: [00:39:40]Yeah,Nathan: [00:39:40]Analogies never throw an eggs in that basket?IMatt: [00:39:42]That’s right. yeah. Yeah. But I think it’s a good one. And I would really continue to like play out through, I’m just getting into a point personally, where I want to spend more time editing, like doing All those more optimization things, but it’s not even so much from an audience growth perspective is I just want to get better.Like I see other YouTubers, other creators that I like, I admire their work so much. And I really am wondering how close can I get to that? But I’m making a choice. I’m making a personal choice to focus more on like the quality and the craft. And I do have like, I’ve built myself to a good benchmark to work on that.But like for so long, literally for four years is like, I’m going to record my planner. I’m going to record, you know, like notion I’m gonna. I’m basically going to do some type of screencast, whether it’s analog or digital, and then I’m going to do a talking head, like, you know, in and out of everything and that’s all I’m going to do.And that was really good for me because it was allowing me to be consistent. I didn’t over edit anything. I took a lot of inspiration from Powell. like Tim Ferris would describe his early days with the podcast and even still like, he does it pretty raw. He doesn’t over edit. And like I was like, yeah, okay.You know, Tim is Tim, but if he’s willing to do that, I can certainly be willing to let go of some of the, you know, the editing, like finer details that especially early on, don’t matter as much as like just actually making the thing.Nathan: [00:41:18]Yeah. That makes a lot of sense. So maybe let’s go back to your arc of the story, right? So when you pass the thousand subscribers, that was 11 months into the channel, is that that’s right?Matt: [00:41:29]Correct?Nathan: [00:41:30]And so that would have been a year and a half into working at ConvertKitMatt: [00:41:34]Yeah. About that actually. Yeah.Nathan: [00:41:36]20 15, 20 16, 20 17, they allMatt: [00:41:38]Yeah. It’s just a blur. Yeah.Nathan: [00:41:40]And so then, like where did the channel go from there? You really doubled down on Bullet journalMatt: [00:41:47]Bullet journaling productivity. And that’s really like, pretty much all I did. I tried to do a like more bloggy blog kind ofNathan: [00:41:57]Yeah.Matt: [00:41:58]After one of the, after one of the retreats, But I actually ended up, it was from, it was from that ocean side. It was from the 2018Oceanside country. Yeah,Nathan: [00:42:09]Confusing me. We’d go to differentMatt: [00:42:10]Yeah,Nathan: [00:42:11]That would, be easier. But what she told me back call, it was just like you know,Matt: [00:42:13]Yeah.Nathan: [00:42:14]Is amazing, but also really difficult for our like, mentalMatt: [00:42:18]That’s right. And so I did like, Hey, you know, I traveled, I did like a travel blog thing and at the time I was doing videos, like my videos would, were pretty commonly like hitting about 5k, you know, on average, if not more. And so it was like, cool, let’s see how this, and then that travel one, just like, didn’t get picked up by the algorithm. People who had joined my channel, where like I joined for productivity and bullet journaling, not like to see you go to the beach. And that was kind of like, okay, well, you know, and it’s an interesting thing as a creator to think about like, well, I like to make this and people are like, so how does it help me?And, you know, there’s an element of that, that I, I still like very much feel like a creative tension around, but at that time it was like, okay, well, I don’t need to worry about my creative output on this particular thing at a time because the other, the other thing that, I’m only now like getting a little bit more used to controlling my time as like being a full-time creator, because at the time it was like, okay, well, if I only am committing like five to 10 hours a week to this as a side hustle, and as like a thing I’m doing, obviously on the side, am I going to use those five to 10 hours to create a video that not many people are going to watch or what I know at this point, people are interested in and it just became a matter of like prioritization as well.Nathan: [00:43:39]Right. So how did that feel? Like was, were you disappointed when the, the blog, you know, this is my wife kind of content didn’t resonate with your audience.Matt: [00:43:49]Yeah a little bit, because there was this element. And I actually like in, I was talking to a client about this yesterday because he was asking me some of these same questions and I wish that I had protected one video a month, or even at the least like one video every couple of months to just be like, this is me, like just doing something that I’m interested in.Like, this is a story that I want to tell. This is like a part of me that I want to show to kind of prime the audience to like, just get to know me in that slightly different way, and just being okay with those videos, not doing as well, because I think I would have like worked in more of like a lot of my personality comes through even in just like the regular videos, but just more of my life, more of my interests, more of the things that I was thinking about. As I’ve now started to pivot, like in lean into that a little more than I’m going through that again, of like, oh, this isn’t what really what I thought I was. And now I’m just more, more confident or just more secure most of the time and being like, yeah, well, I think I’ve said pretty much everything that I can say about how to make lists in your bullet journal.I have like literally a hundred videos. I don’t know what else I can say. And I’ll still say some things, but it’s definitely flipping more for me of like, instead of doing like an occasional non bullet journal video, like every month or two, it’s gonna like switch back, it’s gonna flip the other way. And bullet journal will be like one, one, maybe two videos, every one to two months.Nathan: [00:45:27]Are you worried about, or like, have you seen trends of what that’s going to do to have you countedMatt: [00:45:31]Oh, I’m terrified. terrified. and well, part of the other like tipping point, and this is like bringing it’s like more, where I am on the arc right now and I’ve talked to some other YouTubers about this, you know, results, results may vary, of course, but after January ended and the productivity, you know, the productivity season of December, January was over.I still stayed on like productivity bullet journal videos, but they just started to fall off a cliff in terms of, in terms of views and the like subscribers were down also, like I had a 30 day straight, I had not a 30 day stretch, a 90 day stretch. So an entire quarter that used to be like that entire quarter used to be like, basically an okay.In terms of like month over month, like new subscriber growth, new views. I still have, again, like a whole like library of content, especially the bigger videos that generate like plenty of views every month. And in terms of new videos, new views, like new subscriber growth was just like steadily going down and I’m looking at and thinking like, I just started doing this full-time this is not what I signed up for.I’m doing the thing, which is like this whole other like, weird, like transition of a mindset between like, when you’re more of an employee, I was talking to Jeff Goins about this, but when you’re more, when you are an employee, even at a startup, and I know I can like say this in retrospect now you’re still just kind of looking to either your manager or your founder be like, what would you like me to do that you believe will bring the most growth and like good startup operators, you know?And I felt like I started to do this more towards the end and we’ll be more proactive and be like, this is the thing, you know, that’s what a manager and director. Yeah. But there’s still like this element of like, yeah, I’m the employee. And like, this is what I need to do. And if I continue to do my job in the way that it is expected, I will get my money.I will get my career advancement. I will do my thing. I will check the boxes and being an entrepreneur and especially being a full-time creator, none of that, none of that matters anymore because there’ve been multiple instances even in these first six months. And like what in the world? I like, I haven’t really seen these videos.I’m doing it once a week. Like check, check, check, check, check. It didn’t work. I created this course. It went good so I can make it great. I spend a lot of time on it. Didn’t do the launch that I wanted to, and you’re like, I’m doing things. I’m checking the boxes. Why is this work? What the heck? What am I supposed to do now?And it’s this whole like new mindset that I’m kind of coming into. Like when you are an entrepreneur, you create opportunity and you, like, you have to like, have this, like to bring a Ted lasso reference in like the mind of a goldfish of like, oh, that didn’t work. And I think about this in like, I’ve started doing jiu-jitsu in the last year as well.It’s like, okay, well that didn’t move. Didn’t work. Oh, no, I’m on my back. Now all these say this is going terribly, but like, you have to like, forget these failures really quickly and just learn as much as you can. So that, and like have a really thick skin or just like a really forgetful mind to like, okay, well, even though I felt like I did all the right things, this didn’t work because, to put a, put a bow on like this particular like loop last week, I don’t know if you saw this, like I put a tweet up and said, Hey, if you haven’t set up a course before you have an idea, I can help you do this.It’s a thousand dollars. But if you don’t make a thousand dollars, I’ll just give you your money back and you’ll have your cool. And I just, like, I literally thought of that in the shower and then I tweeted it and now I’ve signed up like seven clients in a week.Like, okay, if that’s going to be the thing, because it’s like this other thing, I worked really hard on this course and, you know, I spent like a month on it and I did, I’m like, but I, you know, God the shower and send a tweet and made like eight grand.And it’ll probably be 10 grand by the end of next week, by the end of the month. And so like, okay, well, that’s, you know, just kind of how being an entrepreneur and being a creator is, and then the next stage of it is, you know, what we were talking about, like early on, just swinging at Berkeley, like, okay, you’ve had the central growth, how do you systematize it?How do you like scale it? And how do you get it to like, be a thing that you can really rely on instead of just like, hoping that you send like a good tweet or the right email or make the right connection. Like it’s creating that opportunity for yourself and then harnessing.Nathan: [00:50:04]Yeah. For sure. What you touched on it is interesting to me is the being responsible for inputs versus outputs at a lot of jobs. you’re responsible for the inputs. Like you’re talking about check the boxes.Matt: [00:50:16]Right,Nathan: [00:50:17]And we like to think that the inputs always result in the output. and often that’s not true. And so as a creator, you’re responsible for both sides of it. And, you know, you can’t be like oh, the AI didn’t get the outputs that I wanted. You know, what that’s okay. Because you’re like, Hey, one of the outputs is money for rent, you know? And, and so there’s a lot more, a lot more pressure there.Matt: [00:50:43]Yeah. And it’s interesting is that even in some of these like rough months, and so I haven’t told this story like publicly, because it’s still so fresh, but you know, like when I have like my, Stripe and Stripe payouts come weekly, it’s a nice little nice little thing. Like, okay, we’re doing pretty good.I was just about to go on this week long backpacking trip, and do like a mentoring backpacking trip, with some high school kids. And I was already like, feeling stressed about as like, I haven’t had a good month. What the, Hey, you know, I shouldn’t be doing this. I can’t just go in the woods for eight days and like not work on the business is not at that point.I’ve made a huge mistake and I’m like, well, I’m still going to do it. I’m not going to leave these people high and dry. But as I’m like going to the woods, I like miss, you know, stupidly open my email and the Stripe payout thing. As soon as like your payout of $30 is on its way. I’m like, oh no, but because you are, you have that, that feeling of like, yeah, it’s like, you know, the only thing that’s coming in is what you create and what you build in what you, what you promote.It’s like this idea. That I’ve been talking about a lot and heard a lot of people reference as well. It’s like, you know, being this full stack creator, like it’s not just that you make thing, but you market the thing, you build a team around the thing. And I have seen like more and more creators, like building more teams around like things that like, they either don’t like doing or not as good at.And so that’s a whole and that’s, but that’s a whole other piece of like building out your like personal stack of skills and responsibilities.Nathan: [00:52:14]Yeah. I was talking about the front end of the day and just explaining like all the business things and realizing, oh, running a business, being a creator is a uniquely assembled collection of a ton of individual skills, because we were like, God for this competition. And I realized like, oh, you don’t have the, you know, knock on this. It’s just a skill that you need to learn. But the like spreadsheets, forecasting skill, like the, I wonder how this is going to work. And so I opened up Google sheets and I like model it out and it’s probably ridiculous. But it’s better than holding it in my head. And then like you write down your assumptions and then you compare, you know, reality to those assumptions.And that’s just one of like a thousand skills that you have to learn. and then like years after you’ve learned it, you’re like forgetting that that’s actually a distinct skill that had toMatt: [00:53:07]Right?Nathan: [00:53:07]Know, like yeah. I mean, everybody knows how to do that and do that a thousand times over and like, that’s the creator experience,Matt: [00:53:13]Yeah. And it goes to this, like, people get really overwhelmed by that and something that I’ve been hammering the last, like several months, especially in fourth graders, is this, like, I think of it like the new 10 X rule of like output and effort of like, if you’re not sure if you want to do something, like try it 10 times.And like really, you know, really give it a good try, but like write 10 newsletters, you know, get 10 subscribers, make 10 videos on YouTube, record 10 podcasts, just to see, like, you don’t have to make this light. We tend to think of things as like making this lifetime commitment to a ship to a pod or whatever, but like do 10 and see how you feel about it like that.Even though I said I was going to do and did like 28 videos, it was kind of like just a slightly more expanded version of like, how do I feel after 28 YouTube videos, I enjoy it. And I’m getting used to it. I’m going to keep doing it. But I had like that really specific, like benchmark of this is the, this is the number that I’m going to get to.And then I’m going to see. And I found that like going from 10 to a hundred is definitely a slog and there are lots of mini milestones, but once you do, and this kind of goes even outside of creative output, but like once you do something a hundred times, you’re going to like build momentum on it. And you’re also going to like, build your own confidence and yeah.Not on ironic. And I’ve seen this across a few different creators. I think maybe Ali doll has like a similar experience, but for me, when I made my hundreds, it was right around my hundredth video on YouTube that I hit 10,000 subscribers and it’s right around like the hundredth, like email newsletter when I started to like, see that, I just felt really comfortable writing those emails.Like, you know, the growth, the growth was good, but just like my personal confidence in it was like so high. That was like, yeah. I mean, it’s time to read the newsletter. I’m going to read the newsletter. It’s not like this weeping and gnashing of teeth, about like, will this work or not. And then you said like, you do it a thousand times because we look at some of our most prolific creators like MKBHD, you know, Casey Neistat, Roberto Blake, like from the YouTube space, all of those guys, like Amy Landino, all of those people have like over a thousand videos published on YouTube and.Oh, yeah. And like, yes, they have great audiences and huge numbers, but like, just look at the output, like their masters, because they have published a thousand videos. And when you think of it in that way, it’s like, there’s so many different things that you can do in terms of mastering and optimization.And like, there are like, you know, I guess you could say there are growth hacks that you could use, but like, look at anyone that you admire and just look at the sheer volume of their work.Nathan: [00:55:50]Yeah, it’s, it’s substantial. I want to talk about how that volume of work turns into, an income.And so could you break down, I guess yeah. How you earn an income now, where it comes from? I think people would expect that like a lot of it comes from YouTube ads. yeah. What are the different, like in your creative stack?What are the things that drive revenue?Matt: [00:56:15]Yeah. The two biggest things that drive revenue for me, that for, especially coming from a YouTube space for a main audience, the two biggest things, it’s still driving revenue?For me are courses and then consulting or coaching that comes alongside or with those courses. And so I don’t even do like a huge, like, you know, tiered course like program in terms of like, yeah, it’s $400 for the course, or you can do like $800 to have like some coaching with me.A lot of the coaching comes naturally from people who have gone through the course. And then usually I’ll do like a, an email once the course is over, say, Hey, if you want me and I’ll drop hints, like throughout some of the, throughout some of the content, but it’s like, Hey, if you want to work on this directly with me here, some of my like rates and different ways that we can work together.But I would say probably 60, 70% at least comes through courses and coaching. That can shift. because I, you know, I do, admittedly not have the best evergreen, course sales funnel that I could have. It’s been a big, like focus for me because, and just take a quick aside, one of the reasons I decided to do full-time creators, cause there were so many things that I wanted to optimize and that I wanted to do that I was never going to be able to get around to on like 10 ish hours a week, never going to be able to do it and stay like even remotely consistent with actually it would have been like, Hey, I’m not gonna make any videos or send any emails for three months so that I can create the system.And then it’s like, I’m back and it’s up. But so from the revenue perspective, the like the percentages between my courses versus coaching kind of shit. But it’s, I would say like pretty even between those, between those two. and then there are all these like smaller things. Like there are, there are affiliates, I would say YouTube revenue on average is a little higher than affiliate revenue.But I also like,Nathan: [00:58:22]Yeah.How much would you be earning? so, someone like I have 60,000 subscribers, what should I expect to be making a month off of YouTube revenue.Matt: [00:58:32]I can say that the most I have ever made in one month of YouTube is 800 and around $850.That’s my best month ever. And, like I mentioned, declining views over the last few months, I will bring it. It’s like 250 this month, which is like, great. You’re like covering software expenses at that point. Which, you know, I do think is like a nice benchmark for people to kind of shoot for is I can, can I cover my costs, but so it’s, it’s pretty low. Like I’ve never made more than $10,000 in a year on YouTube ads and same thing, kind of same thing for affiliates. But because of the jobs that I’ve worked in, like, I haven’t done a whole lot of like software affiliate, promo, and that’s like, I’ve done like other like smaller affiliates, mostly like for books and like smaller things like Amazon affiliate kind of stuff.And those are all like 10% is good for that. But you like for software, like that’s really bad, likeNathan: [00:59:42]Yeah.Matt: [00:59:44]10%. I’m not promoting your thing for 10%. You’re talking about, but like for hard goods, that’s more, that’s a lot more common. And so like, affiliate revenue, especially from a software side is something that I’m focusing more.But even still like between affiliates and, YouTube ads, that’s definitely, definitely less than 20 K and probably more around like 12 to 15 K. And so that’s one thing. And then I do some brand deals and sponsorships, but, admittedly not going super hard after those right now, because again, it’s something that it takes up a lot.Like it takes up a lot of time to like, do a good brand partnership and that there are lots of good reasons behind that, but I’m having to do all of that and it slows down my creative process so much. And it’s such like, like emotionally, it’s not something that I like getting into. Cause it’s like this back and forth and it’s like, well, you know, I’d be like, well, you know, we kind of scoped out this kind of budget.Like, well, it’d be nice to have known that before we got into this conversation. And of course, and I have. Never made more than 10,000, maybe around 10,000 a year on any kind of brand sponsorship deals. So between those three things, it’s anywhere from 20 to 30 K and a year, depending on how, like how well everything went and the coaching consulting courses, like the, those three CS, thoseNathan: [01:01:20]Yep.Matt: [01:01:20]That bring in like 60 to 70% of the revenue.And that’s what I spend my time on.Nathan: [01:01:26]Yeah, that makes sense. So I want to go back to a conversation that you and I had, I guess if we catch people up on the arch, because we don’t have a ton of time left, but, There’s something that happens in startups where first year, like try to figure out what you’re doing. You know, all trying to figure it out at the same time.And the next round of startups is like, can we just hire the people who have already figured that out and had done it before?And so through a transition like that, right? Podia comes in like, Matt, you’ve done this whole thing before we’re trying to do it can like, instead of all of us figuring it out, can we just bring you in And so you, you made the jump over to Podio yet. the thing that I want to talk about is a couple of years after that middle of the pandemic And, a conversation that you and I had as you’re thinking about making this leap to a full-time creator, because I think so many people are like, okay, I did the side hustle thing.This is taking off. And now I’m trying to decide when is it time to quit the day job and go all in.Matt: [01:02:25]Right.Nathan: [01:02:26]Maybe take us through that. And, and some of your thoughts on it.Matt: [01:02:29]Yeah. It was something that I had been thinking about for a while. And certainly I’ve talked, I’ve talked about this on a couple of YouTube videos, but it had been in the back of my head for years. I mean, even.Pre ConvertKit that what would it be like to do this, to do this full-time? and so I had started to, again, to bring up Jeff Goins again, like he used kind of coaching me, mentoring me through some of this process.And he was like, you just need to get better and more consistent at launching products. You’re going to launch a product or some kind of service or something. You’re going to launch something for sale every month in 2020. And that was, and lo and behold, when you tell people like, you know, I’m not saying it’s gonna like go awesome every month.Again, like we’ve talked about some of the ups and downs, but it’s amazing what will happen to your sales when you just offer more things for sale.And so I had been doing that more and more, and it was taking, it was taking off. And what I had really wanted to do just from a mindset perspective is I had a lot of like, like kind of emotional, like money mindset, baggage that I was going to waiting through, at the, at the time.And. I was like, I need to be matching what my Podia salary is. Not just for one month, but like month over month, I needed to do that for three months. And then I had done that for three months. I was like, oh, well, this is nice. Like, should I do this now? And, you know, we got on, we got on a call and I was talking with you through some of this.And you’re like, well, you know, it certainly sounds like your, from what I remember is that you, you were saying like, well, it certainly sounds like you could, but if you like, have more of these systems in place, I just hired an assistant at the time to like, do some of the, like my Neushul work, take that off my plate.He was like, why not just keep basically doubling your income every month for the foreseeable future? And I was like, yeah, that does sound really great too.And this was the summer. I did want to see like what I could do, like with the assistant and how kind of like, again, I had like some fears and hesitation around like, okay, You kind of build your confidence.You also can kind of like draw out your anxiety for too long as well. And you’re like, oh great. I did it for, I had my first 10 came off. I had back to back 10 came months. I had three straight 10 K months, but w what about the next three months? But, and so I did want to keep seeing, I wanted to see how much I could optimize and automate, you know, like without me having to do it.And again, like go into what the rest of that, what the rest of that year was like.But yeah. What, what do you remember from that conversation?And, you know, some of the thoughts.Nathan: [01:05:10]Well, first I love the conversation around money And you know, as a creator, when you go full time and Yeah. I was thrilled that, you like texted me and said, you want to would you be up for talking to you this, the way that I thought about it? I’m trying to think when it was, it w it was relatively early in the pandemic June, maybe.Matt: [01:05:29]Yeah.And there were, it was. And so we were taught, we did, and I didn’t mention that, but we talked a lot about like, Hey, what is the state of the world going to be like, what’s the state of like, you know, the financial systems going to be like, and like three to six months, let’s just, let’s just be cool here,Nathan: [01:05:46]Yeah. Something that I had done in my career, and you have to remember whatever advice someone gives, it’s going to be based in their own story. And so it’s really important. Like a question, if someone’s giving you advice, I, a question that you can always ask is what in your life has shaped this advice? Because they might be like, oh, you should do this creators. They should always do X, Y, and Z. And you’re like, oh, okay. Like that’s from the Bible of what creators should do. You know? Like, like you’re like, okay, really It’s from their own life experience.And so you’re getting the advice without a context. And so you can just ask like, oh, what’s the context, what’s the story or example that made you, that shaped this perspective for you. And for me that the advice that I was giving you was spend more time overlapping the creator income with the, full-time job income, even just a few more months.Because when I was really first making money as a creator, I was selling iPhone apps. And I was getting to the point where I was making $3,000, like two, three, $4,000 a month. And I had a full-time job. And all of that creator income went into a separate bank account. And so that I quit the job. And when I quit, I had $20,000 saved up. Which I was really proud of. Cause they had, you know, was on a $60,000 a year salary.And it was all from this other income that I didn’t touch at all. And it was basically from months of of overlapping. And so that’s where my advice was coming from was basically like, I don’t know how many more months it is, but like we don’t know what’s going to happen in the world right now. We don’t know if like the market’s going to recover dip.I mean, market ended up going up like crazy, but you know, overlap four more months and just save up at least a few more months of up salary.What did you end upMatt: [01:07:37]That’s what I ended up doing. Now, there were some other, there were some other circumstances on that.Like, one of the things was we had a couple of huge projects at Podia, and I was like, I’m going to see these through, these are like things, things that I own. but really, like I remember telling Jeff that I was like, well, if I could quit by the end of 2021, that would be so cool. And he’s like, oh, I bet we could do it before that. I was like, I don’t know if I can do them before that.I mentioned this earlier, but it got to a point where there were so many things that I wanted to do. Like as a creator, like I wanted to start a podcast. I wanted to try that out. I wanted to write more on my newsletter.I wanted to build better courses and try a cohort course, and do more coaching. And especially when you’re talking about time-intensive things like trying to smash all of those in created a lot of like internal conflict for me, and a lot of scheduling conflict and like me working every weekend for like a year, because like, that was just when I had time to do it.And it really came down to okay, I had hit this financial benchmark that I had for myself. It was time to stop making excuses about like, oh, you know, can I still really do? It was like, no, you you’ve actually done it. And also saying like, okay, well, the, the tipping point for me was like making a list of like, here are all the things that I want to do or that I want to try, and realizing that if I was only gonna spend 10 ish hours a week working on this, I would never get to all these things that I want to do because even doing this at like, you know, 40 ish hours a week, like I’ve done now, for this entire year, there’s still things I’m like, oh, I still really want to get this thing done.But now I hav a clear process. I have a timeline, I have knowledge. They’re like, okay, if that is a true priority, I can make it happen, versus like, I don’t know if I’ll ever get around to this. And that was a big tipping point for me. It was just like, there are so many ideas and there’s so many things that I’m excited about.I need to like go all in and make the time to see them through.Nathan: [01:09:42]Yeah, that makes sense. I think having the ability to have the income built up, to have the savings built up to make that leap, that’s really good. we should probably leave it there since we’re, you know, we’ve been talking for over an hour and we could go on for a long time, I think.Matt: [01:10:01]Lots of stories.Nathan: [01:10:02]All the stories. Yeah. We’ll have to have to do a round two, and dive in. because there’s so much on growing startups and like, we haven’t even gotten to the newsletter side of things and…Matt: [01:10:12]Yeah,Nathan: [01:10:13]There, but it’s all full stack creator.Matt: [01:10:16]That’s right.Nathan: [01:10:17]Where should people go to follow your YouTube channel, follow you on social, and subscribe to your newsletter and all the other things?Matt: [01:10:24]Yeah, definitely. So there are a few places for me. If you just go to MattRagland.com/daily is where you can find like the most up-to-date or just MattRagland.com. My YouTube channel is just search for Matt Ragland on YouTube or youtube.com/MattRagland. I’m most active on Twitter in terms of social, but you can find me on the socials @MattRagland.Nathan: [01:10:49]Is it a nice to have one name that you can just getMatt: [01:10:52]So nice.Nathan: [01:10:53]To do the same thing and you’re like, oh,Matt: [01:10:55]Yea. Then from a newsletter perspective, I do write my own email newsletter. And we’ll probably talk about this more at another time, but I’m also co-launching a paid newsletter with my friend, Jeff Goins. It’s called Hey Creator. So it’s a mixed tape for the creative class that we’re going to be launching in the coming weeks.And if you just go to HeyCreator.com by the time this releases, it’ll all be live and ready to go, and we’re really excited to share it with everybody.Nathan: [01:11:24]Nice. And that’ll be a paid newsletter on ConvertKit, and ConvertKit commerce.So I’m excited for that.Awesome. Well, Matt, it was so fun to catch up. Thanks for hanging out and we’ll chat soon.Matt: [01:11:36]Nathan, my pleasure. Thanks so much. It was a lot of fun.

Sahil Bloom is Vice President at Altamont Capital Partners, a generalist investment fund managing over $2.5 billion in capital. At Altamont, Sahil helps lead the consumer products and services sector. Sahil also participates in board activities at Altamont’s portfolio companies Fox Racing, and Brixton.Sahil is an angel investor in over 25 tech startups. He works with entrepreneurs and founders to build scalable and sustainable value for all stakeholders. Sahil also publishes a popular newsletter about business, mental models, economics, and more.Sahil graduated from Stanford University with a bachelor’s degree in economics & sociology, and holds a master’s degree in public policy. While at Stanford, Sahil was a four-year member of the Stanford baseball team. Sahil is also a two-time recipient of the Bruce R. Cameron Memorial Award. This award honors students exhibiting excellence in athletics, academics, and leadership.In this episode, you’ll learn: How Sahil went from 500 to 200,000 followers on Twitter in one year The emerging seven-figure opportunity Sahil sees for localized newsletters Sahil’s system for writing exceptional content The key difference between income-producing activities and wealth-producing activities Links & Resources Packy McCormick Mario Gabriele Anthony Pompliano Fred Wilson Tomas Gomez a16z Future Synthesis School Hone Sequoia Benchmark QED Investors Ryan Holiday Notion Clayton Christensen Institute Pallet Patrick O'Shaughnessy Ben Thompson Sahil’s Links Follow Sahil on Twitter: @SahilBloom The Curiosity Chronicle Episode TranscriptSahil: [00:00:00]I think of writing and storytelling as foundational skills to your entire life. I mean, if you write well, it makes you better in every other area of your life. I think more clearly it exposes the gaps in your thinking so quickly. And that happened to me all on the way. Like the amount that I learned about investing by writing about investing was insane.Nathan: [00:00:27]This episode is with Sahil Bloom. So, Sahil, full-time is an investor. He’s a vice president at Altamont Capital Partners. On the side he has built a massive Twitter following over just the last year before we started the interview.I had no idea that his 200,000 plus Twitter followers have been in the last 14 months, basically since COVID.So, in this episode, we talk about growing a Twitter audience. We talk about all kinds of things. Sahil was a baseball pitcher for Stanford. And so we get into the new name/image/likeness rules for the NCAA.What else? There’s all kinds of good stuf: his creative writing process, his mental models, how he thinks about income versus wealth. It’s the kind of episode that I absolutely love some.So I’m going to get out of the way and let you listen to it. But really quick, if you’d do me a favor and go ahead and subscribe on Spotify, iTunes, wherever you listen to the podcast, and then write a review, I’d appreciate it. It will help the podcast reach a few more people.So, all right. Let’s dive in.Sahil, thanks for joining me.Sahil: [00:01:34]Yeah. Thanks for having me.Nathan: [00:01:35]Okay. So, I want to start with what you put in your bio, which is just three words, investor, educator, and storyteller. I like how concise you’ve got this down to things that describe you, but how do you think about the way that those three interact with you?Sahil: [00:01:50]You know, it’s it’s interesting. I tend to think that there is like a natural flywheel that is being created in real time around the universe of like investing, in the universe of creating. And you’re seeing it in real time with some of these, you know, creative capitalists for lack of a better way to put it.Like Packy is one of my favorite writers, does an incredible job. Mario, over at the The Generalist. A lot of these folks, I mean, Pomp was one of the early ones to do it. A lot of these folks have built these scale platforms, these audiences, and then as a result of that, and as a result of the reach and the leverage that they’re able to get on, having that kind of owned audience in a certain extent, to a certain extent, they’re able to really support these companies.And so, as an investor, as an advisor, you can kind of just create this natural flywheel around it, where your content creation and the creative work is the leading into, these really interesting investment and capitalists opportunities. And then because of those, you’re actually getting more content to write about.It actually is creating this really unique, flywheel that I think we’re really in the early days of candidly, like, we’ve seen a lot of people starting to do it, but it’s very much the first inning in my opinion. And I think there’s a massive shakeout happening in the investment world because of it.All of the VC is, and all of these growth equity funds are just starting to realize that in order to win deals, in order to be a part of these cap tables and really provide value, you know, they’ve said, how can we be helpful as like the joke moniker for a long time, but in order to really be helpful, you need to be able to do tangible things for the companies that you’re supporting and investing in.And these creator capitalists, I do feel like have figured that out and I don’t put myself in the same ranks as those people that I mentioned at all. I’m kind of very green and new to this, but, it’s been fun to start see the early fruits of that.Nathan: [00:03:42]Yeah. It’s interesting to me. Cause you’ve seen for a long time, investors like, Fred Wilson, Tomas Gomez and others, like have these blogs or newsletters, you know, for a long time. And it’s gotten them incredible deal flow and reputation and everything else, but it does seem like there’s a new wave.I don’t know if it’s just the next generation of creators doing this, but it’s much more Twitter forward rather than starting with a blog and a Twitter, a newsletter. do you see other continuations or differences between like sort of the previous generation in the second generation.Sahil: [00:04:17]Yeah. I mean, I think that the VC world has known this for a long time. like the early stage VCs in particular have known that. Audience and reach was a wedge for deal flow. And so like, you look at the of the world, they built from the early days, really like a content house, right? Like they put out incredible thought pieces.You know, they recently launched this thing, Future, which is really just like a content ecosystem that they’re going to continue to expand on. So there are certain firms that have been doing this for a long time, or to your point, there are certain investors who have been doing this for a long time. I think the scale of it has changed, discovery and the algorithms have been dramatically improving.And so, you’re able to generate just a much larger following and a much more engaged following. And so the people that are consistently putting things out, it’s not one piece every six months, it’s, you know, you’re capturing attention because you’re consistently putting out great content that captures eyeballs.Those are the people that are actually able to generate leverage on that audience. And as a result, create value for the companies that they’re investing in. Synthesis School. I think is a great example of it. It’s this really cool education technology platform. They have a long list of amazing investors, all of whom are kind of individual creator, capitalists, and you know, people on Twitter that are big Twitter personalities.And so, they’re able to just basically have this like narrative domination effect where on Twitter, you constantly are seeing content and people posting about this. And you’re like, what the heck is that? What is that business? And it just creates this massive advantage for a business like that. That’s able to capture that mind share and become a like cognitive reference, for lack of a better way to put it for education disruptive.Nathan: [00:05:59]So do you think when, when someone’s looking to take money from, from you as an investor from, you know, someone like Paki or anyone else, who has these audiences, how much is it? The, like the reputation and the brand of that person that I love the term creative capitalist. Cause it sort of differentiates here, but, which is that reputation and brand versus like what they’ll, what that credit capitals will do as far as audience and reach later, like for example, the men’s health, sort of raw, what is it?Brown home. There you go. Ron is a different Rona’s AI is a clothing brand .Yeah, exactly. also a solid company,Sahil: [00:06:44]Cool brand. Yeah.Nathan: [00:06:46]Hone you like I think it was just yesterday that they had these pieces kind of going up everywhere and it was basically all of their, you know, creator, capitalist investors who have these audiences who coordinated some level of a launch.And so I’m curious as people are taking this money, Is it like, Hey, you’re going to be useful as an advisor or is it really like, your money is quite a bit better than someone else’s because you’re also going to promote and put out this link pieces and link to it in your, in your content.Sahil: [00:07:17]Yeah. I think the way that founders are thinking about it, and this is, you know, informed partially by my own perspective, partially from talking to a lot of these founders. So you have a $5 million round, you know, it used to be that you kind of get your anchor like some lead and, you know, hopefully that’s like a tier one VC, a Sequoia benchmark, a 16 Z you know, QED, whoever it might be.And you kind of then have the rest of that round to fill out. And normally you bring on, you know, someone that’s not the lead, maybe a couple of other VCs, but then you have this like million dollar set it’s on the tail. End of it. That’s left. And now you’re deciding between, do I take on a tier two tier three VC to like fill out this round, basically the VCs that are willing to write a smaller check behind a bunch of other people that are leading.Or do I go bring on 10 people at a hundred K each or at smaller checks that can really meaningfully accelerate and allow me to achieve escape velocity. And for these early companies, especially the ones that are consumer facing that like getting eyeballs on their product or on their service, whatever they’re creating is meaningfully differentiating in terms of the trajectory of what the creating.I think it’s a no brainer. I mean, for a lot of these, especially at seed and a stage, like just getting them traction in the early days from a revenue growth perspective is so important because it allows you to go raise your next round and basically push out competition because the way these markets work is like capital flows, especially in technology.When you have potential and of one place there’s capital is flowing to the people who can really meaningfully accelerate and get to that end point and you fall a little bit behind. You’ll find that the capital markets are really pinching for you, and you’re no longer able to raise money. And so. That’s kind of how I think about it is like, if we can go take on that last chunk and for a small amount of dilution, add a tremendous amount of value.That’s a real differentiator relative to taking on another VC on the backend of your, of your cap table.Nathan: [00:09:10]Yeah, that makes sense. So I want to go back to maybe pre Twitter, famous Sahil, like, cause you’re thinking about going into, because you have hundreds of thousands of followers on Twitter now, like it’s turned into a pretty massive audience. What were like, was that a deliberate decision to say, okay, I’m going to go all in.I’m going to build this public persona or this public audience, or did it happen more gradually over time?Sahil: [00:09:38]Yeah, that’s a great question. I mean, look, I, I played baseball in college. I was solid. I wasn’t great. Like I was never the star, so I never had some big following, like the college athletes of today that are the stars and have these massive, massive followings. So I had a Twitter account had never really used it.I kind of. Looked at funny stuff on there and, you know, would see news and things like that. COVID hit in March, 2020, and suddenly I wasn’t commuting, you know, my job, which I was normally on the road three or four days a week for, I wasn’t traveling. I had like all this time that just got unlocked all of a sudden.And I couldn’t figure out like what to do with it. And what I realized was there was all these people, that were so confused about what was happening in the world of like finance business market. and what I like the realization I had fundamentally was that there were kind of two ends of the spectrum of financial education.There was like the, you know, very low end, like tic talkers, talking to you about like random options you should yellow into. And I didn’t view that as particularly socially. Good. And then there was like the high end, which is the establishment financial educators who are basically just throwing a ton of jargon at people, trying to make them feel dumb.It’s like, let me make you, realize that you need to hire me to pay, to manage your money by throwing a bunch of jargon, throwing a bunch of terms at you that you don’t understand. And so what I said was like, I’m going to do neither of those things. I’m going to go straight down the middle. I’m going to be the light Toyota Camry of this market.And just say things in a way that anyone can understand no jargon, no complex terms, just like make it for everybody so that it’s accessible. Digestible. And so I started just writing. it was may of 2020. I wrote my first thread had like 500 followers at the time on Twitter. Didn’t really know what to make of it.I knew that it was a pretty good thread. And I said to my wife, jokingly that I thought it was going to go viral. And she like rolled her eyes at me. And, you know, whatever happened. it started to kind of pick up steam, like tweeted one of my things, mark Cuban retweeted, one of my things. And it was shocking to me, but pretty cool.Cause I saw it start to gain traction and I realized, okay, maybe there’s something to this. but the reality for me was like, there was never a grand strategy to it. I never intended to build some huge audience. Like I thought it was amazing when I got to 4,000 followers. I remember thinking like, this is insane that I have this many people following me that care about what I think.And I kind of just kept putting out content. I mean, over the last year and two months or whatever, it’s been since I started I’ve written. A hundred, 1,314 threads, 90,000 words. mean, it’s just been consistency over anything else, candidly? I never had like one piece that blew me up over the, 20,000 followers or something.It’s just been like a steady grind of just putting things out, kind of a slow drip effect.Nathan: [00:12:22]So that points to us to get a schedule. Are you basically putting out two threads a week? Is that the case?Sahil: [00:12:28]Yeah. I would say in the early days I was like, I had more time cause COVID and everything going on and I was kind of like probably doing three. There were probably times when I put out four things a week, because I had more time, but in the early days too, it was taking me a lot more time to write these things.Because I hadn’t figured out what worked and what didn’t. And so I was like in test and learn mode, it was taking me a ton of time to research and like figure out the right hooks and the way to write things and the style of writing that worked on Twitter. And so I spent, I mean, hundreds of hours over the course of the last year on the weekends, like sitting around, pounding my head into a wall, figuring it out.More recently I’ve kind of gotten into a cadence of like one piece of writing a week. and then with the newsletter I have, you know, I usually expand on that one thread and kind of a more robust newsletter. And then I have the Friday piece, which is a curation thing to kind of help promote other creators.Nathan: [00:13:20]Yeah. So I’m curious, what are some of the things that. That changed as you, well, may, maybe we’ll start with the amount of times, like when you’re putting, let’s go to a single thread, maybe in the early days, how much time was one of those threads taking, and then, you know, now how much time does it take to put together a thread?Sahil: [00:13:39]Yeah. So in the early days, I would say I was doing a lot of like deep research based writing. you know, like I do take an example. Like I did a thread on the game stop thing in January, and like GameStop was, you know, rip roaring. Everyone was wondering what was going on, what had happened, how could that happen?Et cetera. And so I sort of like went into a, down a rabbit hole on understanding, short squeezes and gamma squeezes, and all these complex finance things. And that took me a long time because basically I had to figure out the concept of a gamma squeeze and, you know, the, and how that can be disseminated in a way that anyone can understand, which is like much easier said than done.And I might’ve rethought it if I had, if I had known how long it was gonna take me to figure that out, but that early stuff I would say. You know, would take me kind of five to six hours probably to like research, write, edit, and kind of refine those pieces. Similarly with those like early, like more story-based threads that I was doing, kind of the stories of people’s lives that you see a lot of now on Twitter, less of back when I was doing it, those would take me six, seven hours, cause I was going deep, you know, into these people’s lives and figuring it out.And it was really driven by my curiosity. Like I just love learning about these things. And so I would write about things that I genuinely wanted to go learn about and that made it a lot easier. Cause it didn’t feel like, oh, this is a waste of time. If it doesn’t take off and go viral, you know, at worst I learned a lot and at best I learned a lot and it went viral and got me a bunch of followers.And now more recently, I mean, I’d say I’m in a good cadence of it where it’s like, you know, one of my more kind of like mental models, decision-making frameworks thinking, frameworks type threads probably takes two to four hours depending on what I’m writing. But I have this, like, we can get into it, but I have this just massive repository of like content ideas, notes that I’ve kind of dropped in there over time.So when I actually go to write something, a lot of it’s just there and I just needNathan: [00:15:38]Right.Sahil: [00:15:38]How to construct it.Nathan: [00:15:40]Okay. Yeah. Let’s, let’s focus on that because I think so many people wonder about writing habits and they’re like, how do you weave these things together? You know, like I read one of Ryan holiday’s books as an example, and he, I’m always amazed at his ability to pull in. Like reference some historical figure creator, author, any anybody tell their story, make his point move on.And you’re like, oh, that was so good. Wait, you did that in two sentences. You know, you did that, like in his really concise way, he’s got these perfect examples, but if you ever hang out with Ryan or visit him at his house, he has this like ridiculous collection of no cards. You know, it’s like boxes of note cards per book, and, you know, it’s as crazy process and really every successful author, every school writer that I’ve worked with has some really great organization process.So I’d love to hear more about,Sahil: [00:16:34]Yeah, I love that story about Ryan. That’s a cool one. I’ll keep that for later. yeah, so I mean, my, my strategy with it has evolved over time, but th the way I generally think about it is you kind of have a proprietary content engine, and what that is differs for everybody. Like it, that’s kind of the inputs.So that’s, what are you reading on a daily basis? What are you watching? What are you listening to? All of those things are kind of like your content engine, because those are, what’s giving you ideas, things that are coming up. That’s like all the stuff you’re consuming on a daily basis, and then you have the outputs and that’s like, how do you turn that?Like, put it into your little meat grinder and like, turn that into what you’re writing about. And so the way I generally think about it is. Part of my daily habit as I’m reading and consuming interesting content. and it might be newsletters, blogs, podcasts, tweets that people send me, like all of this stuff goes into my content engine.What I do personally is I have a notion, page that’s a board and it’s, I just have it set up as like, a few columns where I have kind of like, you know, ideas that I have, like, you know, things I’m going to write about soon. Then I have things I’ve started and then like finished pieces that I haven’t posted yet.And then all of the stuff that’s posted and done. And so when I have something I’m reading and it peaks my curiosity, or it’s like, oh, this is a cool concept, whatever it might be. Like, I recently wrote a thread on, the concept of like the Fox and the hedgehog. and that was the one that, like, I had just been reading something on a friend’s, VC funds page.And it was like, oh, this is an interesting concept. Let me throw this into my notion doc. And so I had Fox and hedgehog in there. I linked. Article I’ve been reading. and then like a few weeks later, I kind of got it to learn more about that. And so I went and read some things and I dropped in some notes and dropped in a few more articles and pieces where I had heard people see, you know, or talk about it.And now suddenly when I go to write about it, the next day I have like four sources. I have a bunch of notes sitting there of like things that had come to my mind in the moment when I was interested about it. I kind of had a framework for how I wanted to think or write about it. And so it made the process of starting much easier because I already had all that stuff sitting there.I wasn’t starting from a dead stop and saying like, I need to write this great piece on foxes and hedgehogs. I had all this stuff and I just needed to figure out how to craft it, like sculpt it into what I wanted. So that’s kind of how I think about the process. It’s like, you’re consuming mean things on a daily basis.Figure out what those are. It doesn’t have to be like smart stuff is whatever you’re consuming. It shouldn’t feel. And take that and leverage it into creating this like repository of interesting ideas, because like when you do it that way, you never run out of stuff to write about. I get asked that a lot.Like how do you write something every week? Or how do you not run out of things? And my, my answer is like, there’s an endless amount of interesting stuff out there in the world. And it’s just a matter of like opening your kind of content engine to all of that so that you can then go and write and comment on these things and, and share about it.So that’s kind of how I think about it generally. It’s like kind of, you have the inputs and the output, so you need to figure out what your kind of middle is your middle layer, so that you can turn the inputs into the outcome.Nathan: [00:19:44]Okay. This is a little bit off topic, but when you were. Starting school, you know, going to school at Sanford for like economics and sociology and then getting a master’s in public policy and you’re getting into investing and starting your career there. Did you ever think that you’d be a writer like that?That would be the primary, source. It’s just so interesting the way these worlds overlap.Sahil: [00:20:08]The short answer is no, I never considered myself a good writer. I don’t know, I still don’t consider myself that great of a writer to be honest, like people like my writing, which makes me think maybe I write reasonably well, but I think it’s just effort. Like I’ve just spent more time on it over the last year, a lot of people, but, no, I never really thought I would kind of be able to like create something that had value around creative work that was never in the scope of what I thought about my primary job is still as an investor.Like, and I think we’ll continue to be. And I, and I still think of like investing and advising as kind of like the primary, kind of part of my ecosystem that I’m creating the creative work is becoming a bigger and bigger part of what makes me a unique and interesting investor. and I love it. I mean, that’s the thing for me is. I get so much energy out of the fact that I get to spend time on writing and content creation on a daily basis. I love doing it. You know, I’m starting to do more video stuff. I’m going to be engaging more in that realm, but like the fact that I get to write think read, and that’s kind of part of my job.Like that’s a really, really cool thing to me. And I never really thought, you know, going to school or whatever I thought I was going to do next. It definitely didn’t come within the realm of what I’m actually getting to work on.Nathan: [00:21:23]Yeah, I think it’s so interesting. Like I never thought that I would be a writer and I remember like specifically telling my parents, like, I hate writing. Like why would I ever, you know, why do I have to do so much of this in school and all of that? my mom was an English major, you know, and like big advocate for, writing and all of that, which I now am very grateful for.But it’s amazing the number of people now that, that we think of that are like really quite effective writers that never started there never expected that.Sahil: [00:21:54]Yeah. I mean, I think of, I think of writing and storytelling as well. Foundational skills to your entire life. I mean, if you write well, it makes you better in every other area of your life. Like since I’ve spent more time on writing and have a writing habit that is making me a better writer, I’ve become veteran every other area of my life.Like I think more clearly it exposes the gaps in your thinking so quickly. Like if you, if you sit down and you think you understand something and you try to write it down in a way that, you know, a kid could pick it up and understand it, you very quickly realize if you don’t understand that thing. and that happened to me all on the way, like the amount that I learned about investing by writing about investing was insane because I had to sit down and try to explain it to a five-year-old basically with my tweet threads.And when I didn’t understand the thing, like the gap was like a blaring thing in front of me and I had to go research it more and dig into it and understand it. And so I just think that like, when you write, you expose flaws in your thinking, and that causes you to go down the rabbit hole and learn more about whatever it might.Nathan: [00:22:58]Yeah. That’s good. Is there anything, any resources or things you paid attention to to get better at writing? Like, do you read any of the traditional, you know, and Lamont bird by bird?Sahil: [00:23:07]Yeah, I read elements of style. when I was younger, like I think in high school, I read that and that stuck with me. you know, candidly, like I just study some people that I respect and think of as great writers. Like David Perell has become a friend and I feel very lucky for that, but I just thought of him as a great writer and the things that he put out in his, the elegance of his writing and the different, you know, ways that he was writing things on a, for brig, has become a friend.I think she writes exceptionally well on, on education and some of these topics. I just think that there’s a wealth of unbelievable, talented, people out there that like are publishing things that anyone can read and you don’t have to pay. Like you can go see it, learn from it. And so I try to be a student of the internet in that regard.Nathan: [00:23:53]Yeah, no, that’s good. okay. So since you’ve built such a massive audience so quickly on Twitter with threads, I’m curious, what have you found? What are the things that are really working? What makes a good thread? You know, now you’re writing to those things that, that resonate right away, you know, and you’re like, oh, I can cut out all of that, that I was doing before.Sahil: [00:24:13]Yeah.Nathan: [00:24:14]What’s working. What have you.Sahil: [00:24:15]Yeah. I mean, I would say there’s like a handful of principals that I think were quite well. you know, number one is like, if you’re writing a thread, the hook has to be good. because you need to give people a reason to click and convert and, and, and kind of look through to whatever you’re writing.I do think, you know, now more than ever threads are like a somewhat saturated game, so to speak because people realize, I mean, I, when I first started writing them, very few people were writing threads. Twitter didn’t even have like infrastructure built around long form content. It was pretty janky. You had.Manually add a tweet under each one and copy and paste it in. And now they, they realize that it keeps people on the platform, then it’s a great mechanism for them. And so the algorithms prioritize it. People realize it’s a growth hack, you know, like really is much better for growth than single tweets.And so it’s become a bit saturated, I would say. And so, as a result of that, I think the burden of proof is higher on like the quality of the content that you should be putting out. I think there’s a risk of like losing high quality followers. you know, by just like over, you know, just putting out too many threads that aren’t really high quality.And so my best advice is like, make the hook rate, make sure the hook is like really catchy and draws people in and then just make sure that quality is like exceptional and something. You can be proud of. My whole thesis all along with my Twitter was, you know, there’s like a spectrum of kind of posting frequencies.You have the like, pump who has been exceptionally successful. Every single day, he’s all over it. He’s posting a lot, you know, high frequency. And then I’m on the other end of the spectrum, like a Julian Shapiro’s on the other end of the spectrum. People like that, that like right every now and then, you know, it might be once a week.It might be once every couple of weeks. but what you, what you’re putting out is like, I stand behind every single thing that I’ve ever written on Twitter. you know, from a thread perspective, because I know that I spent a bunch of time on it. I really thought it through, if I didn’t understand something, I was getting it vetted.I was having someone review it. I mean, I just, the internet is permanent. Right. And so I like it’s my personal capital on the line and I wanted to make sure everything was really, really good. And so, that’s important as you, as you put things out there is just like, make sure you feel really good about the quality of what you’re writing.Nathan: [00:26:31]Yeah, that’s a good point that if you’re doing the approach of, like, I went to a Wikipedia article and like made a thread of the content that’s in there, which is a lot of threads that you come across as, that’s a genuine question that ISahil: [00:26:44]Yeah.Nathan: [00:26:45]Reading some of them. the quality really matters.Sahil: [00:26:47]Yeah. I agree. And I go both ways on that. Right. Like I did, you know, a bunch of like, in my early days, especially I did a bunch of what people would have thrown into that bucket of like Wikipedia threads, my perspective on it was always, great. The Wikipedia articles there. but if you wouldn’t have seen it, and it’s a really interesting story and I’m packaging it into something that makes it more broadly disseminated, that’s a value added service that I just brought to the table.And so like, I don’t know, like Morris Chang, I wrote a thread on he’s a founder of Taiwan, semiconductor manufacturing company, amazing guy, incredible story. Does he have like, you know, information on Wikipedia about him? Sure. But like I posted it and 17,000 people liked it and saw, you know, 5 million people saw it that most of them probably didn’t know who the hell he was because they were never going to go to that Wikipedia page.And so I kind of go both ways on that criticism. The reality is that type of thread has become a bit of like a meme where, you know, there’s clearly broad push back against it and, and, you know, it’s become a little bit of a meme of itself. And so I do think it’s worth being kind of wary about regularly publishing that type of content.Nathan: [00:27:55]I think it probably comes down to how unique the story is that you’re sharing. Like maybe it is on Wikipedia, but, well, exactly what you’re saying. That is not someone that I would have gone to look for, but I read and enjoyed that thread. Whereas if you’re just like, here’s this thing about Steve jobs is like, you mean the Steve jobs story that everyoneSahil: [00:28:15]Yes,Nathan: [00:28:16]Heard a hundred times then it’s very different,Sahil: [00:28:18]I totally agree with that. I mean, like if you’re going to go tell the story of. You know, Elon Musk, how he, you know, started space or whatever, like start Tesla or something like, yeah, everyone kind of knows that and it’s, it’s a little bit played up and, and people understand it. And so I just think it’s worth balancing with your own unique content.And that was how I always did it. Whereas like, if I was going to post in one of those stories, I was going to post something that I like deeply researched and did unique educational content and just kind of balance the two. And I think that would like, that worked for me. I think it probably works for others.Nathan: [00:28:51]How do you think about the intersection between your Twitter following and your newsletter? Like as you’ve built that over the last year.Sahil: [00:28:59]Yeah. I started the newsletter. Yeah. I first just created it in January of this year. and I originally just created it because there were a lot of people on Twitter who wanted to get my threads in their inbox. Like didn’t like the Twitter format for them and wanted to just have it in a nicer format.And so for the first, five months of it, like through mid may, all it was was just me sending out my threads the day later, with, you know, just like a nicer format. And so the newsletter list grew to something like 13,000 people just from that, which I was pretty amazed by honestly, you know, more recently.So mid may I decided to do the Friday, I’m calling it the Friday five now, but basically curation focused, five pieces of interesting things that I consumed, like my content engine during the week. and really focused on promoting other creators. that was like, I really wanted it to be a positive, some thing.I’m creating this list and I want to help use it to kind of promote others that are creating great content that need help with discovery that maybe they’re smaller. They need more eyes on their things. They’re putting out great things, but sometimes it’s hard, it’s going into the abyss. And so I’m helping with discovery for them.And so I launched that. and then I’ve recently started just more expanding on the concepts that are my threads. And so it’s sort of like, I think of the threads as sort of a taken down version of a longer form newsletter piece as I’ve prioritized the newsletter. and I, you know, I really use Twitter for like, it’s a discovery mechanism for the newsletter.The reality of newsletters as you know, is that discovery is really, really hard and it’s cobbled together and there’s no like central, kind of authority for discovery right now. And so you need to kind of hack it together and figure out how do you make your newsletter really shareable? How do you drive new eyeballs to it?How do you kind of like generate growth over time? Because. You know, if your Twitter is growing at 15, 20,000 a month, you know, of new followers and your newsletters growing out, like, you know, 50 that’s kind of a problem. and so driving people through and like figuring out how to convert that funnel is like really what I’m trying to figure out and understand right now.Nathan: [00:31:07]Yeah. I think that what I mean exactly the point that you made newsletters don’t have any. You people talking about like, there’s no algorithm for newsletters, so you’re not having to fight to, I read your, your readers. And it’s like, yes, absolutely. You’re spot on. Also, there’s no algorithm for newsletters.And so there’s no distribution, you know, there are, there’s no discovery. And so you’re having to use outside channels, like the newsletter authors from 5, 10, 15 years ago. they use their blogs and, you know, sites like dig and hacker news and others to get along new followers, but also just search, you know, having the, the, long form articles that were ranking really well on Google.And, and I feel like very much the newsletter creators of today are all in on TwitterSahil: [00:31:56]Yeah.Nathan: [00:31:56]Yeah.Yeah. There’s but like very much on Twitter to get that discovery.Sahil: [00:32:00]Yeah. I agree with that. And it’s, it’s going to be interesting to see how the, like the newsletter wars continue to play out. Right? Because all of these platforms are realizing and Twitter realized it. I’m sure Facebook realized it with their recent launch that way. They are providing discovery for a lot of people that are then going off platform with their longer form content.And so Twitter acquired review, you know, Facebook has their new launch and it’s just, it’ll be interesting to see kind of how that plays out in terms of, you know, where people go with their, you know, with their newsletters and how it all kind of, how it all shakes out in the coming months and year.Nathan: [00:32:35]Yeah. Well, let’s dig in there more. Cause like I obviously care about that space a lot being in the middle of it. And you see, you mentioned Twitter and Facebook. Spotify is in the mix. They reached out to us. I don’t know, two months ago about, you know, acquiring ConvertKit oddly, they were more, I thought that it was, they were interested in us because of the music side of things, as we’ve made acquisitions in the music space and all of that turns out, they were more way more interested in the podcast side of things.Like then we have the Tim Ferriss of the world, you know, a lot of top podcasts using ConvertKit. And so I’m curious where all of this goes. I think, you know, like everything five years from now, 10 years from now, we’ll look back and the path that ended up becoming most common, you know, whichever platform dominates or if it stays fragmented, you know, we’ll look back and be like, oh, that was obvious.But in this moment, I think it’s actually fairly up in the air of like, is sub stack going to continue to rise? Will it be review, will bulletin. I mean, that’s what Facebook’s isSahil: [00:33:33]Yep.Nathan: [00:33:34]Be a flash in the pan or will it actuallySahil: [00:33:38]Yeah.Nathan: [00:33:39]Six around.Sahil: [00:33:40]Yeah. I mean, I think if I had to guess, I think Twitter is in the pole position on it. And the only reason I say that is. they are the main mode of discovery for most writers. And so if they can do anything with the algorithms to prioritize discovery, to review newsletters, that’s a massive advantage.Embedded, you know, just because they already have people on the platform. And so th that’d be like it from an investor standpoint, that would be my guess is just that continues to try to ship product that allows them to capture more of the value that their platform is actually been creating for the last 10 years that they’ve captured none of,I mean, like Twitter has been abysmal at capturing the value that’s created through Like, I mean the amount of value that I have flowing through Twitter broadly speaking, Twitter’s capturing $0 of, and that’s sort of a travesty just from a business standpoint. And like, as an investor, you look at that and you’re like, man, that’s a huge opportunity if they can figure out how to capture of that.Nathan: [00:34:35]Will you see it reflected in their market cap versus Facebook’s Write of like, I mean, I I don’t even know what Twitter’s market cap is, but it’s yeah Twitter’s marketSahil: [00:34:45]Cap caps like 55 billion, I think, but like the, yeah, I mean, Twitter is Twitter’s ad product is also just pretty bad relative to, you know, relative to Snapchat or Facebook, but I think it should improve. I mean, as they do more of the creator economy and as they spend more time, you know, actually capturing some of this value, the quality of their ads and the ability to target and all of those things should just get a lot better, which makes their ad monetization better.And that drives the whole engine. So, I mean, I personally, like I’m on Twitter and their opportunity around all of it. I’m also like native creator. I mean, I basically wrote a blog on Twitter over the last year. I’d be like, create these content loops and I’m linking back through the old threads.And like, I sort of do a Ben Thompson does what Stratec Curry, but I do that on Twitter, inNathan: [00:35:29]That’s super interesting. I’m looking at it from the perspective of, if it’s going to be. Like a major platform, like as we look at newsletters, will it be basically Facebook or Twitter at this point that, that dominates that with reviewer bulletin? Or will it be still a mix of the subset convert kit?That kind of thing, like will creators end up starting on review and be like, oh, you know, I wrote some dreads, I got a thousand followers, Twitter like pops up and says like, Hey, you should do a newsletter. You know? And so they start that and then maybe they want more functionality and then they move to a, you know, a ConvertKit or another platform, or if the distribution will become so powerful, that, and the discovery is so powerful that there’s a real reason to stay on,Sahil: [00:36:14]Yeah. I mean, it’s sort of like the. The Clayton Christiansen, model of like disruption and innovation, where you like you, you know, the, the, the platforms that are like very newsletter specific are going to be able to provide a better solution for the full range of potential creators that are on the platform, because that’s their entire focus.Like that’s all they spend time on and, you know, newsletters are never going to be Twitter’s sole focus and they, you know, need to get better at shipping product. And they have a bunch of different areas they’re working on and focused on. I’m sure they have a team that’s focused on newsletters and long form, and I’m sure that team is great and have great engineers, but, if you can be a player that is like newsletter specific and you can provide an amazing solution for every kind of type of creator and archetype that sits on your platform, that’s a real way that you can create a wedge and create a sticky customer base there.Nathan: [00:37:06]Yeah. We’ll see how it plays out because, one thing is that email has never been a winner take all market. You know, we look at like, MailChimp’s the biggest player by far, but even then, I don’t know what their eight or 900 million a year in revenue, something like that.Sahil: [00:37:20]Yeah.Nathan: [00:37:20]And, and you’ve got plenty of players that are, you know, likeSahil: [00:37:23]Yeah.Nathan: [00:37:24]Campaign monitors and others in the hundreds of millions of, yeah.Sahil: [00:37:26]Yeah. It’s also going to be a long tail market. I think the most interesting part of the greater economy are going to be these like micro creators actually that are like hyper-local and writing about, you know, interesting local news as an example where they’re not trying to get the like biggest following in the world, their goal is not to have a hundred thousand newsletter subs.It’s to have like a thousand true fans, you know, that And so I think that that market is probably the most interesting, like there’s going to be a ton. A hundred thousand dollars a year earners that are basically writing like the defacto newsletter for news in, you know, X part of the bay area, or for news in, you know, Westchester county or whatever it might be like.There’s going to be all of these people that rise that are doing that. and making a six figure salary and working from home. And it’s an amazing setup. And so I, I’m actually more interested in that than I am in the like macro influencer world of the creator economy, to people that are going to be making seven figures on all of this.Nathan: [00:38:27]Yeah. And you see all kinds of that. cause it happens not just in the local news side of things or basically people finding a niche based on geography, but it happens a lot with a niche based on, you know, topic or, or where like we’ve seen people, artists talking about very specific things and you’re like, there’s an audience for that.And digging like sure enough, 8,000 subscribers and 50 or a hundred thousand dollars a year in revenue. And, that’s actually a good transition to talk about monetization. So you, you know, you have a, all your content is free. I don’t think you have any paid content out there is that.But you monetize through ads through a job board, as, as you’re looking at, or ads being sponsored content or, or, sponsorships, I should say. yeah. How do you think about monetizing your content andSahil: [00:39:19]Yeah.Nathan: [00:39:20]You played with and, and why have you settled onSahil: [00:39:22]I mean, I’d say I’m in the very early days of figuring all of this out and testing things. My operating premise has always been to never charge people for anything, like never charge people. I just, and it goes back to like, when I first started doing this and writing, it was about education and it was about giving people, empowering people with information that they otherwise wouldn’t have had and making them feel happy or inspired or whatever it might be.And so that doesn’t rely on me charging people for things. I think if I ever. Did something like that was going to take a ton of time. And I was going to have to spend a lot more energy or effort on it maybe, but I can’t really see myself, charging people for anything. So as a result, the flip side of it is like I have all these eyeballs.I have a lot of people that this goes out to. And so sponsors are, you know, willing to kind of support that and have their product or whatever it might be, get seen by all of these people and hopefully clicked on. And, you know, I have a high burden, I would say for like the type of companies that I would work with on that.Because I just want it to be brand right. And people, you know, companies that I’m excited about or would support either way and not just. Hey, some oil and gas company wants to sponsor me, so I’m going to take it on. And so that kind of flows through both, you know, the sponsors for the newsletter, which have been great and companies I feel strongly about, and also to the job board where it’s kind of a natural flow through of like I have this platform, I have all these amazing people that are, that are following me and have gifted me with their attention.A lot of whom are like looking to kind of grow and level up their life and, you know, take on new adventures. and then I had on the other side, all of these amazing companies that are trying to find those types of people and these amazing, you know, this amazing, new group of talent. And so I’m kind of sitting in the middle where like, it used to be that LinkedIn was that person sitting in the middle cause they had gathered all this demand.And so how can I dis-intermediate that? And this amazing company palette came along and it’s doing it disclosure, I’m an investor in palette. I think it’s an amazing company. but they kind of enabled that infrastructure. And so creators can be the kind of direct conduit between companies and between their audiences.And there’s going to be a bunch of flavors of it. I mean, for me, It’s kind of a large audience and I get you access to a lot of people. And it’s a little bit of top of funnel marketing for the featured companies, because I tweet about them. And so you get kind of a social proof that comes with being included and that I included you on the list.But for me, it’s like, I think it’s a really cool thing. I mean, there’ve been people that have gotten jobs through the board and now that’s like, wow, that’s a really neat thing that I was a part of somebody who’s kind of acceleration of whatever path they are on.Nathan: [00:41:55]Yeah, it’s another part of the flywheel for the, I don’t know, your ecosystem, your community, and all of that, where you like someone is going to go from a fan of your work to like, I don’t know, a super fan of some in some way, if they got a job through, through that. And like every company is going to keep track of that.Like hiring and recruiting every person that we’ve ended up hiring, we know exactly where they came from. Cause we’re looking for those, those trends, not that like out of 65 or a hundred people, you’re seeing like massive trends, you know, or statistical significance, but you’re seeing like, okay, This didn’t come from a giant job board.This came from a referral or from, you know, a nice jobSahil: [00:42:34]Yep.Nathan: [00:42:35]Creator.Sahil: [00:42:35]Yeah. Yeah. That’s exactly right. I mean, I think it’s just like trying to figure out now, what is the model that works with these boards? Because for me, like what I want to move towards is fewer and fewer jobs on the board, but make them like really exclusive, almost like a limited edition drop every month that you have like 10 companies that like this month, I’m really going to push and promote and kind of, cause I think these roles are amazing and these companies are amazing and I want my audience to see them versus the like, you know, 200 jobs on a board and you hope people scroll through it and find the thing that they’re looking for.And so I’m sort of like toying with what’s the right model. What’s going to drive the most eyeballs for the companies, so that it’s really beneficial for them. And what’s going to drive the best outcomes for my followers, where like they’re finding unique jobs and getting access to things they otherwise wouldn’t.The other. Great tailwind is that more and more companies are starting to believe in open access, hiring, recruiting, diversity, all of these things that I think and believe very deeply from a values perspective. And so the fact that I can create something to, further kind of progress, that trend, is really meaningful to me, just on a, from a social perspective.Nathan: [00:43:45]Yeah. Yeah, that’s good. And I think that we’re going to see a lot more interesting monetization methods. Like I saw people running job boards as a separate business, you know, years ago, whether it’s like we work remotely or authentic jobs, or like in specific niches, like authentic jobs, for example, you know, really got going in the designer like designer and web developer, ecosystem.But now that’s very much a trend of like creators running their own job board. And I mean, palette is driving that a lot. actually I guess this is one of those places where right. You’re, you’re providing real value as an investor. Not like the thing that we make fun of, of like, oh, how can I be helpful? it’s like, you’re actually running on a job board usingSahil: [00:44:32]Yeah.Nathan: [00:44:32]Advertising it,Sahil: [00:44:33]Yeah. And helping them figure out what’s working, what isn’t like, what could creators use more of different features? You know, frankly, they have a great growth loop. And the fact that like every time I promote a job, that’s featured on my board, it’s a pallet link. That’s getting shared on Twitter and more and more people are seeing palette.And you’re like, what is that? And that includes investors that follow me. It includes, you know, other founders that are looking to promote roles. And so, they have a cool kind of endemic little growth loop gone, and they’re doing really well around it. But to your point earlier, like the sky’s the limit for that type of thing, because as you can.Do more and more of like figuring out how to get to that warm lead that referral-based, the talent pool, where like people are vetted and you’re kind of like really high quality leads on a certain role. the better the quality of the outcomes are going to be for the companies. And so they’re working on things around that, which I think are really exciting because then you stop getting the, like, you know, you’re not just going to the large mass audience, it becomes this like really curated, interesting pool of talent that you’re like linking directly and that companies can have access to.So I’m just really excited about the future of like opening access to, to hiring and disrupting, you know, the, the kind of incumbents like a LinkedIn who I think have just been asleep at the wheel in that market.Nathan: [00:45:49]Yeah, there’s definitely a lot of that. okay. I want to talk about something that maybe is more specific to you. you have this term creative capitalist, which I really like, I’m going to start using more because I feel like it describes, you know, a very specific type of creator, that I, I love to follow.But I’m curious with your background in, playing college sports, as, as a pitcher for Stanford, and then, what you’re seeing, basically, we’re going to see this wave of creator athletes. You know, now that the NCAA has made the changes where you can actually, profit from, name, image, name, image, likeness.Sahil: [00:46:30]Yep.Nathan: [00:46:32]What do you think there? And what, like, what trends do you think are going to come from that? As we have a whole new wave of creators able to.Sahil: [00:46:40]Yeah. I mean, first off, I think it’s amazing. And I think it’s a long time coming. I played college sports from oh nine to 13 and it was like always a topic of discussion. It has been for the last 20 plus years. I think it’s way overdue. I mean, I think it’s a massive disservice to a lot of athletes.It was the one time in their life that they could have made a lot of money off of a very unique skill. And then whether they got injured or it didn’t pan out, I think it’s a travesty that it has been this way for as long as it has. I’m glad it’s finally changed. and I think it’s like a classic example.You know, kind of like a regulatory disruption that unlocks a massive new market, gambling has had the same thing like sports betting, I think probably in the early days of having a similar thing as it gets legalized, but you basically just had regulation that was holding back. a huge market and now it’s come, it’s gone away and you have this huge inflow of talented people that have huge audiences that people feel a high degree of affinity towards.And so it’s a, it’s a huge inflow of new creators basically. And people that, you know, previously didn’t have access to these markets until they got done with school. and the reality of a lot of them is they’re not going to play professional sports. They’re going to be highly, highly relevant for their handful of years that they’re in college.And this is their one chance to capitalize on that. And so I think it’s, I think it’s great. I think there’s going to be a ton of cool business model. that come up around it obviously like agents, they’re probably frothing at the mouth trying to figure out how to go capture this, media studios, brand studios, all of that.I mean, I think there’s just a huge unlock for a lot of these student athletes. and it’s going to be cool to see how it flows. I mean, I think the general way these things will work is that it like probably over-correct where you have people spending too much on these athletes and like the market gets a little frothy and then they realize the ROI is not good.And so it kind of swings back, sort of like, you know, ad monetization on all of these social platforms. Like when they get started, people freak out and throw all the money at the like one thing and it squeezes out the return within that as always happens. And so then you kind of come down to a baseline.I imagine that happens with the athlete market.If I were still an athlete, if I had been anything, I would be all over it. and I think a lot of them should be.Nathan: [00:48:56]So going back, let’s say, yeah, let’s say you were an athlete today. When, when those changes were put in place, what are the things that you’d be doing? You know, what you know now about like growing an audience and monetizing on platforms and stuff like that, youSahil: [00:49:11]Yeah.Nathan: [00:49:12]What would you do?Sahil: [00:49:13]Yeah. I mean, I guess my best advice is like focus on long-term value and owned audience over just like fleeting little like brand deals and promotions. like what value I, my, my mental model around all of this has always been like value capture. if you are creating a lot of value, you should be trying to capture a decent amount of that value you’re creating.And the reality of most of the. Like one-off influencer deals and things like that is you’re actually creating a lot more value than you’re capturing. And it’s not a great mechanism for long-term value or longterm wealth creation. I think Warren buffet said when it’s raining gold, you put out a bucket, not a thimble.And I always loved that quote. I think it’s like very, various student and very relevant for these kids and young, young men and women that are going to be out in this market. It’s like, it’s raining gold right now in a lot of cases for you. but you want to make sure you’re setting up infrastructure in setting yourself up in a way that allows you to capture it for the longterm and to capture a good proportion of what you’re creating for the longterm.And so if that’s, you know, rather than doing an influencer deal, it’s like starting your own thing or having your own ownership of something. You’ve seen some of the tech talk influencers doing that Tik TOK creators, realizing that like equity is much more valuable to them than just taking a $10,000 put up a post, whatever it might be.Spencer rattler the quarterback for Oklahoma. It was like starting a merchandise line and it’s his own thing. And he’s like, I think that that is really interesting. and you’re going to see a lot of cool, it’s going to be a great like idea lab, which I’m just excited to be around for, to learn from, because people are going to test and learn a million different things with all of these athletes that are around, trying and seeing what works.Nathan: [00:50:55]Yeah, it’s really going to be all the same principles, but you know, over again with a new, a new group of people, right? Like I wrote an article called the billion dollar creator, and it was basically about those who go from an, a specific, like how I might’ve had my audience by selling with a one-time thing.That would be the brand sponsorship, the other deal, you know, something like that. And instead, focusing on the ones who like really build equity in something they’re starting a company, they’re saying like, great. Instead of letting someone else sponsor my audience, I’m going to be the one selling that product, you know?And so it’s the, like glossy is an honest company and you know, these other ones where. You know, the individual creators, likeSahil: [00:51:40]Yep.Nathan: [00:51:40]Capture all of that value rather than say like, great, I’ll get paid 10,000 or a million dollars. You know what, depending on your influence level for a one-time thing.Sahil: [00:51:50]I totally agree. It’s something I think about constantly too, is like, you know, as I continue to progress in this world, you know, what am I actually building equity in versus earning income around. And I think you see it, you know, like creators have figured it out. Ben Thompson, you know, with launching his passport thing where he’s kind of creating a platform for people to engage and he’s creating equity around it and trying to build something Patrick O’Shaughnessy, you know, with the Colossus platform and kind of being the go-to place for, for business ideas and business breakdowns and investing.I think a lot of people are doing that. I have something in the works right now with a good friend and, that we’re partnering on that I think is kind of in that vein that I’m really excited about. But, it’s definitely something that people should be thinking about in real time.Nathan: [00:52:33]Is that the, when, when people ask on Twitter, like what are you most excited about? And you answered the thing that I, that I can’t talk about yet.Sahil: [00:52:39]Yeah. Yeah. We’re close to being able to talk about it, which is exciting and it’s coming soon. but we’ve got, a couple of people that are going to be really, really cool to be involved with on a project. it’s going to be dope. I’m super excited.Nathan: [00:52:52]Nice. Yeah. I mean the biggest thing, like going back to monetization, you know, just for creators in general is really looking at what do you own long-term what do you have equity in? Right. Cause the sponsorships even, well, the job board, right? It’s something that you’re building equity in. Right. And so I like that.Cause it, it builds this reputation. Sponsorships are a great way to drive revenue and be more connected with companies build relationships. But like that’s not a. That is just cash.Sahil: [00:53:23]Yeah,Nathan: [00:53:24]Doesn’t, it doesn’t build equity. And so I’m, I’m superSahil: [00:53:27]Yeah,Nathan: [00:53:28]Like this is the thing that I preach all the time when I’m talking.I guess I don’t preach it publicly as much.Sahil: [00:53:32]Yeah.Nathan: [00:53:32]That I preach behind the scenes allSahil: [00:53:34]Yeah.Nathan: [00:53:34]You’re talking one on one.Sahil: [00:53:35]Back to me mental models, just cause I about these things a lot, my mental model for this one is like, you kind of have there’s there’s two sides to your life. You kind of have like income producing activities and then wealth producing active. and the way you want to set it up, you know, like how I think about it is you need an income producing activities because you need to pay bills.Like you need to pay your mortgage or buy groceries, like car bill, all of those things. That’s like you have income producing assets. Any, Delta between your kind of expenses and what you’re producing from an income producing activity standpoint should be funneled into wealth producing activities. so that you’re actually building wealth and equity and whatever is.And so wealth producing activities can be as simple as investing in the stock market or in whatever you’re investing in. Or it can be like further along on the risk curve where you’re starting a startup, you’re building something you’re, you know, investing in startups, you’re, you know, trading in crypto, whatever it might be.It’s like here, you’re taking, you know, one end of the, like flywheel of your personal kind of financial ecosystem and using one end to kind of fund the other and actually build long-term equity and wealth in something. That’s how I tend to think about it is like you need income producing activities and any excess that exists on that side and people should strive.I think, to live within their means any excess is, you know, used and funneled into wealth, producing active.Nathan: [00:54:54]Yeah. I love that. you and I share a passion for helping people build income, build wealth and all of that. And so I’m going to use that simple modelSahil: [00:55:04]Yeah, love itNathan: [00:55:04]Lot. It’s good.Sahil: [00:55:05]Good.Nathan: [00:55:07]If someone asks them to put her in. And I was curious about this as well. going back to the investing side, if you’d only invest in two companies, public or private and what would they be?Why?Sahil: [00:55:15]That’s a tough one. I don’t want to spend too much time on, on private cause I’ve already probably invested in some of these, you know, pallet is probably one of those for me right now. Like I just, I think palette’s an amazing company and I’m huge, huge fan of what they’re building. I, on the public side, honestly, Twitter could be one of the companies I would invest in today.I just think the potential and. The external perception of Twitter is very different from my perspective on it. And so I think I have a variant perception of the future that, you know, that would allow me to capture a lot of value if it goes, if, you know, if I’m proven right. in the future, Synthesis School, I, again, disclosure, I’m an investor in that business.I just want that business to succeed because I think the world is a better place if it succeeds. And I want my kids to be in it and taking classes it and being a part of it. and so I just want that business to succeed so badly, whether my investment ends up being an amazing one or not because of, you know, for whatever reason, I just want that business to win. And so I, I would invest in that 10 times out of 10 I’m sure.Nathan: [00:56:18]Just for everyone listening, give like the 62nd 32nd pitch on synthesisSahil: [00:56:23]Yeah. Synthesis School is a kind of alternative education program for children. And basically the whole idea is that like our school systems are flawed. They don’t teach kids how to think. We created a school system that was based for the industrial age and not for innovation and creativity and the digital age.And so Synthesis School originally was started for Elon Musk’s kids, at space X, it was called Ad Astra. They productized it, spun it out. It’s now an online based learning program that is team-based cohort-based, and creates this amazing learning experience for kids. It’s like two days after school, per week.And some of the best kind of thinkers and doers in the world have their kids in it already, which has been a really cool proof of concept for it. but it’s just an amazing program. and you, you can look them up. I think they’re at synthesis.is and, on Twitter as well. You can find them, Synthesis School.Nathan: [00:57:17]Nice. Yeah, I’m a huge fan of alternative education. I was homeschooled. And so I had a very, very different path. And so programs like Synthesis and other friend is working on one called primer.Sahil: [00:57:29]Yep.Nathan: [00:57:30]That’s coming along really well. So I mean, just seeing all of these, these optionsSahil: [00:57:33]Yeah,Nathan: [00:57:34]Of people basically changing up the model, it’s gonna be, it’s gonna be good,Sahil: [00:57:37]Yeah. Try different things. It’s like the whole idea of the ideal lab, right? Try different things. See what works and see what drives the best outcomes, and whatever that is, let’s pour money into and end up with, you know, kids that are much better off than we were.Nathan: [00:57:49]Yeah. As we wrap up, one last question that I’m curious about is, as you built the audience, especially cause it’s growing so quickly, right over the last, you know, basically zero to 200,000 plus followers, and in a little over a year, what’s been like a favorite moment or a favorite opportunity that’s come about from it where you’re like, wow, okay, two years ago, this would never have come in the door without having like gone down this creator path.Sahil: [00:58:14]There’ve been so many man. It’s blown me away. I mean, it’s really the access to amazing people that I think is so incredible about the whole thing of being a greater and audience building. I mean, I don’t know, like DM-ing Toby, the CEO of Shopify and having him respond is like one of the coolest moments, you know, my life at the time when it, when it happened or, you know, having mark Cuban share one of my things and then respond to a DM I sent him, thanking him.Like that was just so neat to me, that I have access to these people because I have spent time on this and have built around it. So, you know, I just think it’s incredible, and I’m so grateful for it. I still kind of pinch myself cause I just think it’s, it’s really neat and I’m excited that it’s happened because people think I’ve created value for them.And so hopefully I can continue to do that and continue to grow, but, that’s the burden that I need to continue.Nathan: [00:59:07]Yeah. Oh, I love that. I mean, it’s just, it’s the power of light but consistent writing, creating habit, and then applying it in a way you’re making that flywheel of like better content, keep learning, figure out better ways of distribution, and I’m impressed with how quickly you’ve spun that flywheel.But, for anyone listening and following along, like, okay, say that took two years, five years to get, you know, even 10 years to get to the point it’s a hundred percent worth it.And it’s a great thing to pursue.Sahil: [00:59:36]Yep, absolutely.Nathan: [00:59:37]All right, where should people go to follow you on Twitter? Subscribe to the newsletter? All the things.Sahil: [00:59:43]Yeah. I’m at Sahil Bloom on Twitter. You can find all of my content there and links to all of the other things. That’s probably the central repository for me and I appreciate everybody and I, my DMs are open. So if you have any questions or things come up, I try to respond to everything.Sometimes it takes me a couple of days cause they get flooded, but, I will get back to you. So thanks so much. I appreciate it.Yeah.

Charli Prangley is the Creative Director at ConvertKit. Charli has a bachelor's degree in design, with an emphasis on visual communication, from Massey University. Before working at ConvertKit, Charli worked as a designer for companies such as Mitsubishi Electric, Xero, and her own Liner Note Kids.Born in New Zealand, Charli now lives in Valencia, Spain. She is passionate about helping creatives improve their craft and process, as well as working on her own side projects. When she’s not working at ConvertKit, Charli creates weekly content on her YouTube channel and podcast, Design Life, where she shares insights about working as a professional designer, and gives tutorials and advice on design tools and concepts.In this episode, you’ll learn: How to balance your side hustle with a full-time job How Charli turns curiosities into money-makers Why newsletter creators need a YouTube presence Charli’s tips for getting more YouTube subscribers Links & Resources ConvertKit Basecamp Webflow Johnnie Gomez Pallet Sahil Bloom The Bloomboard Jessica Hische Charli’s Links Follow Charli on Twitter: @charliprangley Watch Charli on YouTube Design Life Podcast on Twitter: @DesignLifeFM Design Life Podcast website Charli’s website Episode TranscriptCharli: [00:00:00]I want to show people the real life of a professional designer; the projects that I work on, how I work on them, how I make decisions, the challenges that I run into along the way. That’s the kind of thing that I’m looking to share. And then that sort of lens frames all my content. Not just on YouTube; it’s also the newsletter, the book, anything I tweet, as well.It sort of all comes from this.Nathan: [00:00:31]In this episode I talk to Charli Prangley. Charli is the Creative Director at ConvertKit. She and I have actually worked together for four-and-a-half years, and during that time, well, actually before she joined ConvertKit, she’d built a popular YouTube channel about design—specifically marketing design.She’s at over 200 or right about 200,000 subscribers on YouTube, which incredible.She’s got all kinds of projects.In this episode, we dive into things about design. She and I are both designers, so we love those topics.We talk about side hustles, and how you balance that with a full-time job. Her career, moving up the ladder, becoming Creative Director at ConvertKit, and all the other things she wants to create.What gives her energy; what doesn’t.We talk about sharing things about money online, and how that can be a tough topic.She shares her income, she does videos about salary and making income from side hustles, so we talk about those details, and then we talk about as a newsletter creator, is YouTube something that you want to pursue?And tips and tricks and ideas for that.Anyway, I’ll get out of the way, and we’ll dive into the episode.Charli, thanks for joining me:Charli: [00:01:42]Yeah. Thanks having me. I’m excited—honored to be on the Nathan Berry show.Nathan: [00:01:47]That’s right. I’m glad it gets that kind of enthusiasm.Is only because we’ve worked together for so long?Charli: [00:01:59]Maybe, I don’t know, honestly, actually I’d probably more excited to be on if we hadn’t worked together for so long.Nathan: [00:02:04]That’s right. You’re actually like, “Fine, fine. I’ll come on your podcast. But to be clear, I’m doing it during works hours, and you’re paying for this.”Charli: [00:02:12]Yeah. This is a favor to you.Nathan: [00:02:14]Yeah. Whereas separately, because maybe if we hadn’t spent the last four years working together, then, then you’d actually really want to do it.All right. Well, maybe let’s start there because we have spent the last four years working together, four-and-a-half.Charli: [00:02:33]Yeah.Nathan: [00:02:33]And yeah. So coming, approaching five this fall. The first thing that I want to ask you about is how you think about all the different things that you’re doing as a creator.As I mentioned in the intro you’ve got, you know, the YouTube channel, you have a podcast, you have a newsletter and everything else.And I, I just love to hear how you think about the intersection of those things. And then we can get into the intersection of a full-time role, and all the full-time creator things.So what’s the, like Charli’s creative landscape?Charli: [00:03:06]Ooh, I like that. I would say that I’m aiming to make the kind of content that would have helped out, you know, like the me from two years ago.And that’s kind of been my approach the whole time through. So when I started, maybe I was making stuff more for beginners, and every now and then I will still, but I’m trying to like level up my audience as well as I level up in my career.And I love the term creator. I feel like it’s definitely the best way to describe me because I’m not just a YouTuber. I’m not just a podcaster, or just a blogger, or a writer, or whatever.I do all the things like wherever I feel drawn to create in whichever method I feel like will best express the thing that I’m trying to teach or share is what I lean into.Nathan: [00:03:49]Yeah. that makes sense. Uh that’s how I feel, like, you can’t put me in a box.Charli: [00:03:54]Yeah, no. How dare you.Nathan: [00:03:55]The only box that I’m willing to accept is a giant all-encompassing freeform box of creator.Charli: [00:04:01]That molds, and like, changes shape as you do. Yeah.Nathan: [00:04:04]Yeah, exactly.Okay. So you have all of these things. Maybe your most recent thing that I want to talk about is Inside Marketing or Inside Marketing Design is that marketing would be an entirely thing.We’re talking Inside Marketing and Design. I’d love to hear first, why you wanted to start that, and maybe the seed, the direction a little bit.I’ve heard you talk about like design being so focused. People either talk like graphic design, or they talk product design, you know. So, we’re like into user experience, user interface.I’m curious how marketing design fits into that and your, your desires there?Charli: [00:04:42]Yeah. So, honestly Inside Marketing Design started as much with my content does, which is, I wish this existed. It doesn’t exist. Maybe I’ll be the one to make it.I found myself just like really wanting to hear about how other companies set up their marketing design teams, how their marketing designers get work done.And when you searched around for like, I dunno, medium articles and things like that, it’s all about product design. It’s all about product design teams, UX design teams, and how they work with engineers.And I’m like, what about the marketing design side of things? It’s super important, especially in tech where most marketing design happens, most marketing, sorry, happens online and you need the digital design to make that happen.A brand is super important. Building up a company to, you know, a high level. And I just think it’s completely underappreciated marketing design in the industry.And so it’s like my personal mission to raise up the profile of marketing design eyes wider in the design industry and tech industry. And yeah, Inside Marketing Design interview show, that was completely self-indulgent where I got on calls with designers who work at other tech companies and learned about how they did that.Nathan: [00:05:51]I feel like the best podcasts and newsletters and things like that are completely self-indulgent they come from this natural curiosity, like that’s where this show comes from. It’s just like, these are the people that I want to talk to. And there’ll be more likely to say yes to talk to me if it’s for a podcast, you know, because otherwise like you end up in the, can I pick your brain thing?And that’s like, Nope, no, no, no, no. Like bat goes in a very special bucket of, of emails. But if you’re like, can I have you on your podcast? You’re asking 90% of the same thing, you know, and the best questions are the ones where I’m like, I genuinely want to know this.Charli: [00:06:28]Totally. Yeah, exactly. That’s definitely the approach I take to it. and since then, I’ve been, I’ve been surprised by the response that the number of people who are also interested in this very specific niche thing I was interested in as well, you know, it definitely has a way smaller audience than if it was perhaps a product design podcast or a UX design podcast, but that’s kind of the point, right?Is I want to make content for this niche, this very underserved, I believe niche in particular.Nathan: [00:06:55]What’s interesting is that I feel like, the market exists. Like, I’ll be, obviously there’s lots of marketing designers, right? Cause all going to the like every time Stripe comes out with a feature most beautiful page ever, you know, and all of this, right. we look at, even just within the Nisha software, like all of the design is so beautiful today compared to what it was even five years ago.And so obviously there’s marketing designers everywhere. It’s just that the content hasn’t caught up with that, for whatever I feel like the UX designers and, and the freelancers have been so much more prolific in like content of this is how I run my business and this is how we structure our teams.And so it feels to me like the market. It’s not that the market is small. It’s that? it’s just not established yet. There’s not big of a community,Charli: [00:07:49]Yep. Totally. And there’s not even one specific term, like even marketing design, some companies would call it brand design. Some would call it just web design, the creative team. I don’t know. There’s lots of different terms for it. So yeah, I guess I’m also trying to like unify us all under this marketing design umbrella as well, because it is it’s design that helps market product or service.Nathan: [00:08:10]Yeah, totally. I, it takes someone to like, Hey. this is the term that we’re all using. Just gives you’re wondering, that, you know what you mean is marketing design. who are some people that you’ve had on the podcast that are particular companies that you’ve interviewed where you’re like, we’re really excited to dive in and learn what they were doing.Charli: [00:08:31]Yeah. So I was really excited to have it start out from base camp on the first season, back when he was still at base camp. and I don’t know, it was just really interesting to learn about how they, how they do things. same with Webflow had Johnny Gomez from workflow on I’ve been a big fan of workflow for a very long time.So, yeah, digging in and hearing more about the day-to-day because it’s one thing to just look at a company’s marketing site or their marketing materials. And it’s another to hear about the process that went into producing it. And like, where does this designer sit within the org structure of the company?How do they do things? So yeah, we go into lots of nerdy details like that, and it’s been fun. I feel like I’ve learned from, you know, doing the episodes myself. Like, one thing that Johnny actually brought up is that when he’s designing sites for web. He would write the copy for them as well. Like he doesn’t use lorem ipsum or fill a copy.He’ll like write real copy. And I would usually write like, sort of like a placeholder copy that indicated what I wanted to say. Like, it would be like headline about this. but since then, since that interview with Johnny, I’ve leaned in more to like, okay, let me just try it. Let me just try, write a headline.And you know, the writer can come in and fix it up later if they want to. But yeah, there’s been lots of cool little, little learnings that have helped me in my process and yeah, I hope has helped the audience too.Nathan: [00:09:47]That’s interesting. I feel like people do this with every skill that they’re not, that they don’t feel confident in. I was going to say competent, but often they’re competent in skills that they don’t actually like competent and confident. you know, don’t always co-exist. And so I think that with design there’s a lot of people who are like, oh, that’s design.I can’t like, I’m not a designer. I can’t touch it. And you know, I’m always trying to use tools. Like pick-me-up like gradually drop people in and be like, oh, but what if you tried? And you know, and like, yeah, maybe it looks terrible, but here’s this process. And I feel like copywriting is one of those things where people are like, I don’t know how to do that.I’m not a copywriter. I’m, I’m a designer. I’m whatever else. And it’s like, okay, but if you had to, what would this headline say? Oh, would probably say something like. Okay. Like, that’s probably 70% there, you know? And then like if you had to write a better one, what would it say, oh, maybe it’d be this, you know?And, and that being able to jump in, like, you’ll find often that you’re competent, even before you’re confident in those skills.So, you’ve got the podcast. Well, actually really quick. You said something about the podcast that you said, you mentioned seasons. how do you think about, doing in seasons and how does that fit into like your workflow,Charli: [00:11:06]Yeah, I wanted to do it in seasons because this is actually my second podcast. I have one called design life that I’ve been running with a co-host for years. And that is not one will seasons. It’s sort of like an every week thing. Although we are on a break at the moment, and INathan: [00:11:19]Like a Ross and Rachel style break or what kind of break.Charli: [00:11:22]Uh we’re on like a summer break.Nathan: [00:11:24]Okay. Okay. So everyone knows you’re on break. It’s not you think you’re on a break and your cohost doesn’t you areCharli: [00:11:31]Yeah, exactly.Nathan: [00:11:33]I’ve been watching friends lately. Can’t help it .Charli: [00:11:36]So, I knew that I wanted to do Inside Marketing Design and seasons because of just how much work it is to do podcasts constantly. I thought I could package, like have my goal was 10 to 12 interviews. To correlate them into a season and also do a wrap up episode at the end of the season, just covering some of the things that I learned.Some highlights, things like that to tie a little bow on it. And, yeah, I’m starting the prep work for season two right now. my goal is to do one season a year of yeah. 10 to 12 episodes eachNathan: [00:12:07]Nice. What I like about that is you’re able to be deliberate about what you’re committing to. You can start it when you actually have like energy and momentum towards Um and then it’s also a fixed commitment.Charli: [00:12:22]YesNathan: [00:12:22]Saying, I don’t know what the analogy is. Like you’re not even hopping on the treadmill or if you are here, like this is a five mile brightener, this is a three mile run or whatever.Right. And then you’re like, and then I’m going to hop off instead of being like, Hey, I’m gonna get on this treadmill and I’m going to do it until I get burnt out and regret doing it. And then I’ll quit about three months after that.Charli: [00:12:42]Yup. Yup, exactly that. And I would compare it more to a marathon than a five mile run, but, you know, just get technicalNathan: [00:12:49]Some of us are more ambitious than So what’s the, like, going back to the creator landscape, in your world, you’ve got the podcast. It seems like that is the main driver, the main source of new content, for, Inside Marketing Design. But you’ve also got a newsletter, a job board and then a book coming.So how do you think about the other other aspects?Charli: [00:13:13]Yeah. So, the newsletter I started, honestly, I feel like it was from something that I’d seen you write, talking like building up your authority on, it was probably in authority actually. Now that I think about it, building up your authority on a topic before you’re going to release, you know, paid product about it.And so I thought, well, this would be a really great way for me to generate like a warm audience of people who interested in marketing design. If I start a marketing design newsletter, so it’s called the marketing design dispatch and it goes out on Mondays and. It’s sometimes it’s like a little essay.Maybe it’s like even a piece of writing that I’ve been doing for the book that I’m writing about marketing design, or maybe it’s a deep dive into analyzing a new marketing website that I’ve seen a rebrand, something like that, as well as sharing content that has been useful for me or that I’ve seen around the internet.And yeah, I’ve had a good response to it so far. Cause I, I started just sending it out to my existing list and yeah, I gave people the option to opt out of getting it if they didn’t want to. And maybe like a couple hundred people did that, but the most, the majority of my list is stayed around for it, which has been cool.Nathan: [00:14:19]Yeah. So how, how big is that list? And then where did that existing list come from?Charli: [00:14:24]Hmm. So the current list is 18,000 subscribers. I just did a big cold subscriber call the other day. up to like 24,000. And so you’re my engagement graph and ConvertKit’s looking nice and green at the moment. yeah, and the majority of my lists previously had come from one, I have this really popular YouTube video about DIY screen printing.And so people sign up to my list to get a free opt-in that has like a PDF written with the instructions. So those are the ones that, you know, probably went cult. Let’s be honest, but I also have a couple of other opt-ins about creating a design system for marketing website. How to advocate for yourself as a designer, self promotion as a designer, just a few sort of like things of credit along the way, as well as just a general sign up on my website.So yeah, most people are there because they’re interested in my content, I guess. yeah.Nathan: [00:15:15]And so probably a lot of that is coming from either Twitter. but the bulk of it being from YouTube. Is that right?Charli: [00:15:23]A lot from YouTube, also a lot from my own website and from Twitter, I would say. Yeah,Nathan: [00:15:28]Okay. So you’ve got the newsletter there and then this is actually something that I was really curious about, like why launch a job board that feels like another, you’re already juggling a bunch of LikeCharli: [00:15:39]Great point.Nathan: [00:15:40]how does that fit in.Charli: [00:15:41]Yes. So the job board came about, honestly, because of the platform that I have it on at school palette, and it’s a way that communities can create a job board to advertise roles to their community. So it’s quite like create a focus and it’s meant to be heavily curated. So it’s not like you come to my board and you find any type of design role.It’s like a job board specifically for marketing design and brand design roles. Yeah, it’s my goal to have it be the place that if you’re looking for that type of role, you can search on here. And if you’re hiring for it, you come post on my job board because you know that I’m going to send it out to my audience of people who are interested in this topic.And like, it just feels like a good fit.Nathan: [00:16:22]Right.Charli: [00:16:23]Pretty low lift so far, honestly. So that’s another reason why I took it on because it wasn’t like I had to make the site myself or anything. Pallet has the system and, they manage the payments for the job postings and things like that. I just go in when one gets submitted and see if I want to approve it and it gets posted.Nathan: [00:16:40]Nice. Yeah, no Southern people. There’s a creator who I hope to have on the podcast soon named Sahil bloom, who has. Couple of hundred thousand followers on Twitter, a popular newsletter and all of that. And he just locked, launched a board called bloom boards, think is a great, I chuckled, you know?And so it’s just interesting as a business model, because right, when you have this audience of tens of thousands or, or even more, that’s really what you’re, you’re selling access to. And it’s interesting, you know, like I’m used to selling products to individual creators where $50 or a hundred dollars or $200 is enough money that people are thinking hard about it.But what’s interesting about it. A job board is that especially when the tech world, where someone is like, Hey, can you help me find this person that I’m somewhere between a hundred and $200,000 a year? And so, like, I assume you’re, I don’t know what your experience is, but the willingness to pay for that product is fairly high and they’re really paying for access to your 18,000 subscriber newsletter.Charli: [00:17:44]Yeah. exactly. And the, I also have a tier on the job board where you can choose to pay, like a much higher fee. And I mentioned it in a YouTube video as well, that goes out to my audience of like 200,000 on there. And so it like, yeah. Smart idea. No, one’s taken me up on that option yet, but I hope in time they will.Nathan: [00:18:02]Well, if nothing else, it’s there for like package it, like positioning in there of like, well, maybe we would dive in what are the price points right now at the time ofCharli: [00:18:10]Oh, shoot. I can’t remember off the top of my head. let me look it upNathan: [00:18:15]Google it either. That’s tooCharli: [00:18:17]I’m just going to go to my own job board. How about that? So I think it’s, I think it’s 300 for an initial, like just a plain posting, 500 for featured, which then has like a, you know, a special section of my newsletter as well.And then I believe I priced it at like 1200 for the one that includes the YouTube shout out, which is like in line with what I charge YouTube sponsors is actually a lot cheaper than what I showed you, shoot responses, but, you know, I figure it’s a good fit and it’s doing service to my community to be promoting it well.So,Nathan: [00:18:46]Yeah. that makes sense. Okay. So what was the research that you did going into, like, I imagine it was more than like, oh, palette looks interesting. Great. Let’s add this monetization method.What went in as you, as you were seeing of like, okay, I have this community and a job board is the way that I want to monetize it because I saw these people do it, or I you knowCharli: [00:19:09]That was the reason why. Yeah. it was mostly my friend , who was my co-host on the design life podcast. She had started one with palette and I saw her doing, and I was like, oh, this looks interesting. Like, tell me more about this. and she said that pellet had approached her and explained the system.So yeah, I reached out to them, got on a call with them. They’re super like new as a startup basically. And so, you know, we’re in, on, on the ground floor and helping them along the way with building features and, you know, suggesting what to build that sort of thing in their slack group. yeah. And I just decided this makes more sense than trying to build a, maintain a website of my own because they are doing that work.And, you know, as someone who creates on the side of a full-time job, leading a team at ConvertKit, I, you know, want to have this be minimal effort on my part get it out there. So it just made sense.Nathan: [00:19:58]So you’re not very far into this, right? OrCharli: [00:20:00]No, it was brand new. I’ve only had like one person pay to post so far. It’s veryNathan: [00:20:04]Yeah, we’re just getting started. And so maybe this is a better question for like some point in the future, but like, if someone was coming to you and saying like, okay, I have a newsletter of 10 or 20,000 subscribers is like, should I consider a job board as well? Like as a monetization method, what, what would your, perspective be at this.Charli: [00:20:26]Right. Yeah. I think that is a good question, but I can definitely answer now. I would say if you could, if your niche for your newsletter is super cool. And there’s like a certain type of people who read it or that you’re speaking to when you write it, it could make sense to have a job board. there was some initial effort for me in finding some jobs to populate the board with sort of it wasn’t launching with nothing, you know, but from then on, it feels like very low commitment because it’s mostly inbound, right?It’s people coming to you to post. So it’s not going to be worth it for you if you don’t have perhaps the profile in the community yet to get those inbound leads or, you know, get people visiting your board so that you have the good stats to tell people about that. Yeah. If you do have those things, consider it as an extra income stream.I think it’s smart ad like diversify where your income is coming from. that was a big thing that led to me. we haven’t gotten to this yet, but last year I doubled the income that I made from my side hustles and having like multiple small streams is how I did it rather than having like. Giant successful stream, if that makes sense.So yeah, I’m considering the job board as part of that.Nathan: [00:21:36]Yeah. I want to get into the side hustles as well. maybe before we do that, let’s just go right there. Now the, I guess the first thing that I’m curious about is you share all of your numbers transparently publicly, that I do as well. and you also dive in, like you have popular videos on, like salaries for designers, your own salary history.Like one of my favorite videos that you’ve put together as like here’s the salary that I’ve had at every role, know, across myCharli: [00:22:05]Every raise that had throughout my career. Yep.Nathan: [00:22:08]Yeah. And so, why, why that level of transfer.Charli: [00:22:12]Nathan. I feel like you’re fishing for compliments, even though you don’t realize you are, but It’s honestly it’s. Cause I, I, I got a lot of value from reading your income reports, seeing people like pat Flynn’s income reports as well. And it just, I think it, it changed my mindset on money. It just it’s something that we are taught that it has a taboo around it.Right. And we all keep it secret for some reason cause everyone else does. And so we think we have to as well. And I don’t know, I guess just seeing other people share and seeing the value that I got from it and seeing how it didn’t change my perception of them, if anything, it made me respect them more.I was like, well, you know, I feel like I am confident in what I’m earning and I’m confident that I’m being paid, what I’m worth. So why don’t I just share this history with other people and tell them about it? And yeah, since then I feel like I’ve slowly gotten more and more transparent and the latest income report on my blog is the most transparent I’ve ever been.And yeah, I, no regrets.Nathan: [00:23:09]It’s something that comes up. Like the reason I ask the question other than fishing for compliments, which absolutely doing, like, know, on a payment. the reason that I ask is because I think so many people are so timid about it. And so I like to have more of a conversation, not about like, just the like bold, brave people who are out there doing it, but like just to try to normalize it so much more.And so I’m curious what have been some of the downsides, you there’s always, there’s gotta be at least some YouTube comments or some emails something. And so maybe we can, can share a little bit about what the, I guess the, the outside edge of like, Hey, this is the downside, rather than just telling everyone like, oh, it was fine,Charli: [00:23:53]Yeah, totally. And I would love to hear this from you as well. I’ve had YouTube comments on both ends of the spectrum to the salary video in particular, some saying, this is irresponsible to tell people this is their rate. They’re going to set them way too low. If they go and asking for what your salary is, you’re being underpaid, that sort of thing. probably the people who live in San Francisco and work at like a Google or a Facebook or something like that.Nathan: [00:24:16]Yeah. It turns out you make like 500 grand a year. Like something crazy. You, you have to sell your soul. That’s the only, like, I think, but other that,Charli: [00:24:24]So I’ve had people. I’ve also had the people saying like, oh my gosh, that’s like so much money. design is like way over valued. There’s people who are like, you know, saving lives in hospitals.And I’m like, yeah, this is a fair freaking point. I won’t swear on your podcast. Great point that maybe the answer isn’t, we should pay designers less, but maybe we should pay doctors and nurses more, you know, let’s take that approach to it. but honestly less of that than I expected is is what I’ve seen.Maybe, maybe those sort of comments are happening in a less public forum. Like maybe people are talking about me behind my back. I don’t ButNathan: [00:25:03]Probably not,Charli: [00:25:04]Yeah, well, Who knows, but either way the, the people who I care about, I haven’t heard that from, will say one interesting thing I noticed is that since sharing my salary history and things, whenever I like offer to buy my family dinner or like, I know it will be, I’ll be like, oh, pay they protest less.Now we’ll just say that.Nathan: [00:25:27]That was going to be my next question is how it interacts with family.Charli: [00:25:31]Yeah,Nathan: [00:25:32]And so now it sounds like they’re just like,Charli: [00:25:36]It.Nathan: [00:25:38]We can split it or something, but they only say it once instead ofCharli: [00:25:41]Yeah, yeah, They don’t protest too hard. What about you? What have been some of the, like the positives and negatives you’ve had.Nathan: [00:25:47]YeahI mean, lots of positives, because I feel like the more transparent you are, the more, I mean, the more people read your content and the more they enjoy it, more they understand you. and so the more they want to connect, like soon, the number of people who I really respect and I’m a fan of who have reached out and been like, oh, let’s chat.And I’m like, you know, I like playing it. Cool. I’m like, Hey. Yeah. Yeah, that’d be great. I, you know, I’ve, I’ve like seen your stuff on Twitter and really it’s like, no, no, I’ve listened to every episode of the podcast or like some version of that. Right. And it’s like, be cool, Nathan, you know? so there there’s been a lot of that on the downsides.Let’s see. I would say this is more early on, right? Because they’ve been transparent with numbers for the last eight, eight years or so. but especially I got started in online business when I was really young. And so. in the communities that like, like friends from high school or church or, you know, or my wife, Hillary is friends like in those circles, a lot of people were much earlier in their careers.So there was a time that, you know, people were making 25, 30, maybe $40,000 a year in those circles. And then over here, I’m like, if you, if they ask me what I do, I’m like, oh, I’m a writer or I’m a blogger or something like that. But on my blog, I’m talking about how, like I made $250,000 lastCharli: [00:27:14]Yeah.Nathan: [00:27:14]Right. And so there were a few awkward times when those worlds like crossedCharli: [00:27:20]Yeah.Nathan: [00:27:21]And it was, yeah. But there was a long time ago.Charli: [00:27:24]Handle it when, when they did cross though? Like how did you handle the situation? Awkward conversations.Nathan: [00:27:31]Yeah. well I remember one person in particular is one of. We’re not, we don’t, we aren’t very good friends with them anymore, not because of this, but just different apart, but it was, one of my wife’s friend’s husband, you know, it’s one of things where like you go to a party and for whatever reason, everyone segregates by gender.And you’re what, why did we do this? You know? ButCharli: [00:27:56]This a middle school dance? Yeah.Nathan: [00:27:58]It was one of those things where someone who was genuinely interested in learning online business and, you know, and that sort of thing in the group and like follow my blog and understood. It was like asking questions about like, oh, how did this latest launch go?And, and I was like answering the questions, but I was just getting this feeling of like awkwardness from this other person. And so it, like, I always try to be transparent, but like, I couldn’t, I was struggling to reconcile like in-person Nathan with online Nathan at that time I was glad that that resonates.Charli: [00:28:34]Yeah totally. Yeah.Nathan: [00:28:35]It was totally normal to be able to talk about like a book launch or something, online, but to talk about it in person of like, oh, this made like $40,000 in the course of a couple of days was a really weird thing to say. So I like dance around it and kind of set it. And from this other person got like just a straight up like, oh, wouldn’t that be nice to just like, send, you know, send an email and make all this money and not have to work for it.AndCharli: [00:29:05]Well, I just, I did the work in advance though, soNathan: [00:29:07]Yeah, No, that’s not the moment where you’re like, be like, well, let’s take a step back and let me get out the let’s explain leverage and how you build a life. You know, it’s like wrong, wrong vibe. just kind of shut down. I didn’t know how to navigate that situation.So I did it poorly, you know, like kind of laughed it off. Someone else like felt the tension in the group and like made a joke and took the conversation some other way, you know?That was probably the most like awkward scenarioI’ve ever had. I, I think I have the same thing that you do have, like family is now like, okay.Yeah, no, you can, that’s fine. We’ll let you pay for that. which is honestly one of my, like, I, I like paying for thingsCharli: [00:29:51]Same. I wouldn’t offer if I didn’t want to.Nathan: [00:29:53]Yeah, exactly. So, and my family has been, been fantastic about all that.Charli: [00:30:00]I think, another thing that, I’ve noticed is I dunno, like, I think if you’re going to start talking about money online, you have to, you can decide how much you want to share. Right. Just because you’re being transparent about something doesn’t mean you owe anyone anything more than what you decide you want to share.So for me, I share my income and I shared my business expenses, like the content production expenses this year, but I don’t talk about like, oh, here’s all everything I paid in taxes, everything that I paid to like live my life, or I don’t know. Like there’s some things that I’m not interested in talking about online.And I don’t know. I, I started out giving people excuses when they would like push for more and more and more. But now I kind of feel like I’ve given you a lot. You take that and run with it. it, it doesn’t, it shouldn’t matter to you. my answer when people ask me, well, how much did you pay in Texas?And I just say, I paid the correct amount. I mean, what, benefit does it have to you to know this? You’re not living in my exact situation, so I don’t understand like how it would help. So, know, I decided that’s not a thing that I want to talk about and, I am fine with that. And maybe people aren’t, but yeah.Nathan: [00:31:14]Yeah, I think that’s a great boundary and that’s something probably that I haven’t talked about this on this podcast that I’m curious for your answer on is what boundaries have you set in your like personal versus like creative life. Right? Because there are definitely people who would look at you and I, and be like, oh God, I could never like put myself out there in those ways.Like, I would never show up on camera. I like, I wouldn’t talk about my life. I wouldn’t put things on the internet under my real everyone has these different boundaries. And so I’m curious, like, what are some of yours? And have you set those over time?Charli: [00:31:45]Yeah, I think over time, I’ve settled more into my content that I put out online, being very focused on my work and obviously who I am showing up to do my work, who I am as a designer, but I don’t share a lot of my personal life online. I’ll share like the odd Instagram story here and there, pictures of my cats, that sort of thing.But you’re not going to find me for example, vlogging on the weekend being like, oh no, I’m just hanging out with my boyfriend watching formula one. You know, that’s, that’s not the kind of content I’m trying to make. I’m just trying to make design focused. This is my work. This is my process is how I get it done.Sort of content. I did used to, vog more of the personal side of things and it was fun. And it’s fun to have those videos to look back on, but it’s also a lot like it, as much as you try to live in the moment while also capturing it, your attention is always going to be split some way. And so, you know, that’s just a decision I made was to take more time offline when I’m not working and just document the work as what I share has been a good, good split for me, that works for me and my life and my family.Nathan: [00:32:52]Yeah, that makes sense. I feel like it’s something that people probably do, both what you and I have done of like, not really having those clear boundaries and then you just gradually figured them out andCharli: [00:33:02]Figure out what worksNathan: [00:33:03]Think there are people who, you know, have things like, oh, we’ll never put, like my kid’s face on online or something like that.Right. I think like has that, has where like the like certain clips there’ll be blurred they’re like, oh, they’re walking through New York. Yeah, exactly. It’s the back of the head. Or you’re like, oh, there’s a kid in a stroller that you can’t really see, you and it’s just interesting to try to try to navigate that.So I appreciate people who are intentional. And I think I just, haven’t, there’s a lot of things that I haven’t figured out exactly. And you’ll see how it changes over time.Um, cause I think we, you know, what you’re comfortable with comfortable. You know what the YouTube channel of a thousand or 10,000 subscribers is different than what you’re comfortable with it 200,000.Charli: [00:33:53]Yeah, And, that changes over time, too. Something I recently started doing this year is streaming my work, streaming Twitch and. I dunno, I’d, I’d been very resistant to doing live streams in the past because I was just nervous about what having people watch me design. Maybe it was imposter syndrome I was feeling, or I don’t know, just worried about people judging me when they’re seeing messy middle of the process, rather than me presenting like this final thing that I’ve finished and it looks great.And there’s been, that was a fun challenge to overcome. Honestly, it’s been a really fun way to build community over on Twitch. like diversifying my audience in a way from not just being focused on YouTube or Twitter, but, building small audiences elsewhere. It’s been cool.Nathan: [00:34:36]Okay. So you said diversify, which is interesting. And I like that. do you worry about diluting your efforts in diluting your audience? Picking up another none other channel or platform.Charli: [00:34:49]Kind of, but also no. so I have this person in my mind who is like my creator idol. you’ve probably heard of her Jessica Hische. She is a designer, a letterer illustrator, and I’m just such a big fan of her work and in how she shows up online in that, she’s just doing cool stuff all the time. Well, that’s what it feels like anyway, like doing cool things, putting it out there, you wouldn’t call her a blogger or a, I don’t know, like just a speaker or just someone on Twitter.Like she’s all of those things. and she just like shows up in different ways to share different pieces of her work. That’s what I’m trying to do. I don’t want to be known as just a YouTuber and lock myself into that. And I feel like I did for a while. And it’s only really been probably in the last year that I feel like I’ve pulled out of that.And that’s not how I mostly hear people describe me anymore. yeah, I’m just trying to finish show up online and share things and, yeah, maybe I could be more successful in terms of building a bigger audience if it was just focused on YouTube, for example, but that’s not my end goal. Right. So it, it doesn’t serve me.And I’m more interested in just being, being a well-rounded person. Like I call it a digital citizen. This is what I did my, honors degree project about some bit nerdy about it. But yeah, I like being a digital citizen and giving stuff to theNathan: [00:36:13]Yeah.I like it. Well, so maybe if we dive in a little bit on YouTube since that is where the bulk of your audience, know, has come from and, and all of that, what were the things like as you look back over the last, you know, 200,000 subscribers. What were the things that made the biggest impact any step functions and growth or, you know, particular videos or really just habits that paid off over time?Charli: [00:36:41]I think it’s mostly been habits. Honestly. There’s only one sort of, step point in my growth that I can point to is when I was featured on a list of the design channels to follow on YouTube. And that gave me like a big boost, butNathan: [00:36:55]how ofCharli: [00:36:55]YouTube. Hmm. I can’t remember now several thousand, like more than what get.It was significant, like a difference inNathan: [00:37:03]when you were at like 10,000, 50,000.Charli: [00:37:07]I can’t even remember now. I feel like probably around like 20,000 ish maybe.Nathan: [00:37:14]So we’re talking a significant boost at this point. It’sCharli: [00:37:16]Yes,Nathan: [00:37:17]10%, 20%.Charli: [00:37:19]Yes, In like within a week sort of thing. Major that I started to see those numbers increase. but most of my growth on YouTube has been like slow and steady. Just like climbing up over time for the first five years of being on YouTube.You mentioned habits. I didn’t miss a single week about bloating for five freaking years. I don’t know how I did it now. I Ms. Weeks all the time now, but that really helped me get in the habit of making videos. Get in the habit of having an idea, figuring out how to express it, learning how to edit, putting it out there, getting a response, making a better next time.I think if I had stressed a lot about my first however many videos I made in those five years, I would have taken a lot longer to grow if I’d been trying to perfect each one. But instead I was just like, no, what matters is getting something out there? So I’m going to get something out there. and that, that was a huge part in building my consistent.Then the other thing I think I’d say helped is deciding who I’m talking to on YouTube. I started out making content about a bunch of different stuff and eventually it settled. No, the reason I wanted to make videos is to talk about design. I should stop talking about makeup and cooking recipes and stuff like that.And like, let’s just talk about design. That’s what I’m most passionate about. so yeah, going all in on that has enabled me to get posted on lists like top designers to follow on YouTube, that sort of thing, and become, quite a well-known design channel. Yeah.Nathan: [00:38:47]One thing that’s interesting to me is that even in choosing that knee seat to go for design, you haven’t gone. What I think most people would find the most, likely path, which is like a whole bunch of design tutorials. definitely have designed tutorials, but like, if I’m looking specifically for how to, I don’t know, combined shapes and Figma, your channel is not the, like, you don’t have video of, you know, exactly how to do that.You might introduction to Figma.That’sCharli: [00:39:17]I do.Nathan: [00:39:18]Yeah. And you might, I have watched that video. I was part of me switching from Photoshop Figma was watching your to videoIt’s not hypothetical. but, but what’s the reason for not habit, like not going tips or tutorial base.Charli: [00:39:35]Honestly, it’s, it’s what I said before about, how a lot of my content comes out is making the kinds of things I want to see. And what I wanted to see is the behind the scenes of people’s processes and talking through like the decisions they made about a project, like why did they do something this way?That’s what I care about more than the, how I feel like there’s a million tutorials out there to tell you how to combine shapes and Figma or whatever. there’s people who are passionate about that and who are really great at explaining things succinctly. And they do it a lot better than I could. And that’s just not like the space I’m looking to fill.I want to show people. The real life of a professional designer, the projects that I work on, how I work on them, how I make decisions, the challenges I run into along the way, that’s the kind of thing, but I’m looking to share and, and that sort of lens frames, all of my content, like not just on YouTube, that is also the newsletter, the book, the anything I tweet as well.It sort of all comes from this.Nathan: [00:40:32]Yeah, I think that’s the Mo the best way to be long-term authentic and say interested in when you, what you’re creating there, like practical side of me is like, but you could do that and have the tips and that would drive, you know, search results. And, and I feel like that’s a tension that so many creators have, like, this is what I want to make.And this is what I know will also get me short-term results. Like, should I do both? Should I split my focus? Is that something you ever thought about or struggled with?Charli: [00:40:59]Yeah.That’s why I have a Figma one-on-one video is because I know that that does do well in search. And I think that, I think I’m pretty good at explaining at an introductory level, a new piece of software to someone I wouldn’t really consider myself a power user of any software. So you’re not going to find like a advanced Figma tips video on my channel.Cause I’m not, I don’t, I’m not really an advanced user. I’d do what I need to, but I think I’m really good at making, something that seems scary or new, like a new piece of software that you have to use feel easy to understand. And so that’s, that’s the gap I try to fill in that sense to appease the algorithm.Like right now I’m planning a web flow one-on-one video to sort of go along with this one-on-one series that I’m doing. and my hope is that people see that and then stick around for the rest of the more process driven.Nathan: [00:41:48]One way that I think helps bridge that gap for people sticking around for, for your content is that you put your personality and yourself in it. Right. We don’t dive just into a screencast. you know, and it’s like, you’ve heard of watch a video. Like I know I’m watching one of Charli’s right?It’s not like any other video that I just found through through search.Charli: [00:42:08]And I’ve comments about that. Nathan people have said like, oh, why is your face so big on the screen? It’s always funny how the negative ones talk about you. Not to you say, why is her face on the screen so big? And I’m like, well, you’re probably not going, gonna like the rest of my videos that are pretty much only my face.So it’s okay that you don’t like this oneNathan: [00:42:26]I don’t know if you know this, but you’re on my channel.Charli: [00:42:31]And I’m the one reading these comments. Yeah.Nathan: [00:42:34]Yeah. Yeah. That’s that’s good. If anyone was starting a YouTube channel today, either in the design space or something else, like what would you tell them? What would you, would you say as far as like that advice to kick it off?Charli: [00:42:46]I think ask yourself what is not being talked about or not being talked about in a way that you personally find useful or like a perspective that you personally have in the design space in particular, there’s a lot of content about like how to become a UX designer, that sort of thing. So it’s like, and it’s probably the same for a lot of topics is finding your unique angle on it now is important that the number of the space is more saturated and leaning into your personality, because that is sometimes your point of difference is that there’s only one of you.And then you have lived your experience and white has led you to this point. And that could be an interesting angle to put on anything that you want to teach or share. But so that, and also just get freaking started. People seem to like, I don’t know, obsess over perfecting the video, set up in their audio.And I think it’s Roberto Blake who says that your first 100 videos are going to like be. Not good. I, again, I’m not sure if we can swear thisNathan: [00:43:45]You can swear. That’sCharli: [00:43:46]Okay, going to be shit, Nathan, they’re going to be shit. And so you should just need to get through them and like get in the habit of producing and getting used to seeing your face and hearing your voice.So yeah, if it’s something you want to do get started sooner rather than later, so you can get that awkward stage over with faster.Nathan: [00:44:00]Yeah. Yeah. And then like gear and everything else. You just like gradually replaced thing at a timeCharli: [00:44:06]Exactly.Nathan: [00:44:07]And gradually upgrade it. he did something last year. No, I’m trying to think two years ago, I hate what is time anymore.Charli: [00:44:13]KnowsNathan: [00:44:14]You made a font and that’s something that I like looked at.There’s like normal people. There’s designers, and this is the way that I think, and designers who can make a font. And for anyone who’s just listening to the audio. I’m like doing stair-step things with myCharli: [00:44:30]Yes. You have to imagineNathan: [00:44:34]So that puts it in a category of like, I just think of that as an incredibly difficult thing and not like a great moneymaker, like there’s a lot of difficult things are high difficulty and high rewards, you know, the effort versus impact, like you’re at the top of both.Right. And that’s the reason like, okay, great. You know, that’s very difficult, but you did it and there’s a high, high financial reward. I’m curious the way you thought about making a font, because the way that I see it is that it is very high effort in low financial rewards. but maybe the reward and impact comes some of the.Charli: [00:45:16]I would say, I definitely have not, I dunno, earned even a minimum wage in my sales yet from the hours producing the font. I’m just trying to edit it up right now. Cause it was, I was sold across a few different platforms, but I think I’ve earned about six, 2,600 pounds from it so far, is like not bad.I don’t know what that is in us dollars. should I Google that quickly?Nathan: [00:45:40]Sure. Let’s do it. be the episode where we Google everythingCharli: [00:45:44]3,606 us dollars is around about how much I’ve made from the font. So it’s notNathan: [00:45:50]Any matter, a thousand hours into it. And so $3 hour. don’t know.Charli: [00:45:55]But the cool thing about it is one. It was just a thing I wanted to do. I thought it would be fun to try. Cause I’m, I’m an avid like font collector myself, and now it is my passive income. Like I, and, yeah, the bulk of that income has come in the past year where I’ve done minimal marketing for the font.I’ll like tweet about it or share whenever someone else, someone posts like an image of them using it. but there’s not been a huge concerted effort gone into that. And so that’s kind of cool. It feels it’s my first passive income that I feel better about than ad sense, for example, cause this is the thing created and I don’t know.It’s more intentional.Nathan: [00:46:35]Well then you also get to see it in use around the oh, that’s my fault.Charli: [00:46:41]Yup. Yup. It’s really fun. It’s it’s especially cool because I just created it as a hand, drawn looking font, but people very quickly just started using it as a font to annotate designs because it does look handwritten and yet it is also like highly readable.And so I really leaned into that as the, like in the way that I frame the font now and the way that I market it is. Yeah, this is to annotate your designs in a really clear and legible way that still looks and written. And we even use it on the convert kit website.Nathan: [00:47:11]Do it comes full circle.Charli: [00:47:12]Yes.Nathan: [00:47:15]On that note. I want to talk about the intersection between having a full-time job and life as a creator, because I think people would, would think of it as, oh, I have this, and then maybe I have this one side hustle or I ha like ha and, and you’re able, I think, through the leverage that you’ve made with, like coming into the job with a, you know, established audience and habits and everything, you’ve been able to build, you know, like a small design empire.And so I’m you think about balancing those two things and, and what you’d say to someone else really, who is like straddle.Charli: [00:47:54]Yeah, I think I’m getting clear on what you want from these two worlds. It’s important. So for me, it really matters to me that I’m still designing. And so, that’s why I, and like contributing to a project that’s bigger than just like my own. That’s why I like working at ConvertKit. I do not enjoy freelancing, so like, it would be hard for me to really fulfill fulfilled, I think freelancing right now, anyway, who knows that could change in the future.That’s why I am not interested in going full-time on the creating side of things. And so knowing that means I have okay. I’m no I’m going to work a full-time job. And I know that creating is also important to me, all this content that I’m making. I don’t want to give that up either. So how do I do them both?How do I figure this And it’s just been a, a constant, constantly changing, I dunno just way that I get this done when I was, I don’t know when I was younger, like, I dunno, five years ago, I used to wake up super early in the morning and do a few hours video editing and things like that on side hustles before starting the day, I feel like I’m older and tired now, and I do that.But what I do now that I am earning income from my side hustles is pay people to help me. So I pay for editors. I pay for, yup. Video podcasts, editing, some VA’s who helped with my bookkeeping and content management, uploading that sort of thing, just so that I can really keep the parts I enjoy to do myself and hand off, as much as possible of the stuff I don’t enjoy.And it’s been a worthy investment for me because of, yeah. It making it sustainable.Nathan: [00:49:31]Yeah. Yeah. That makes sense. don’t know if you posted this in slack or in, on Twitter, as I mentioned it somewhere else, but there’s a video that you were editing recently yourself. And that was a bit of a, I don’t know, not a wake up call, but I was like a reminder like, oh yeah, this is a lot of work.Charli: [00:49:50]that was one that I wanted to edit and then put out like two days later. And so I knew my editor wouldn’t have time for a quick turnaround like that. So I was like, well, I’m just going to do it myself. And I’m like, oh, okay.I remember why I outsourced this.Nathan: [00:50:04]Yeah. That’s even outsourcing something that like, you know, well and are good at done for many years. But I think what you’ve found in that, or, I mean, the point that I want people to take away is like, you can actually create really a lot, if you set up the systems you’re willing to let go of the things that you’re skilled at, but don’t like, they’re not the thing that makes the content, know, like maybe if, you and I were filmmakers, right.The editing and having just perfect. Right. That would be part of it where we’re like, oh, wow, that was incredible. Right. But, but like we’re, we’re teaching content, we’re sharing things. It needs good editing, but it doesn’t like, that’s not what makes her break the perks of the video. And so outsourcing that allows you to create so much more content.Charli: [00:50:52]Yep. Exactly. And that’s often my answer when people say like, oh my gosh, how do you do it all? I’m like, well, I pay people to help me. That’s how I do it all. I don’t do it all myself.Nathan: [00:51:01]Yeah. When you sit down like a video that you’re making in a given week, I don’t pick a video. I’d love to hear kind of what your process is like. Do you just sit down and flip on the camera and start talking? Or are you writing a script first? what’s your process? Like how much time does it take?Charli: [00:51:17]I these days, honestly, we do tend to write a script when it’s a video. Like, oh, let’s say for example, a recent one, I uploaded was one explaining the differences between, I think it was five different job titles and tech that you often see. that is one that I sat down and wrote a script for first, when I film it, I don’t necessarily, I don’t use a teleprompter and I don’t necessarily read the script word for word, but it helps me process my thoughts to write it out first.Sometimes I find when I do a video, that’s just bullet points. It takes me a lot longer to film because I end up like talking about something and then I’m like, no, I don’t like the way I phrased that or we’ll go back and like repeat it a bunch of times. so yeah, getting that out of the way first actually speeds it up for me to spend a bit of time writing.And yeah, I have my filming —set up like this background, if you’re watching the video version of this podcast, is just where I do my filming. And that makes it pretty easy to just set the camera up, turn it on and film. I generally like to fill more than one video at a time as well. Cause if I’m going to like, I dunno, put lipstick on or something, I want it to be worthwhile.Nathan: [00:52:20]Sense. What you were saying about writing the script made me think of back when I was doing like designed to tutorial content. What I would often do is I would, I would know roughly what I was going to make or like the tip I was trying to share or whatever. And I’d have like, An idea of like, here’s the fake app that I’m going to do it or any of that.Right. and I would record the tutorial and end it and I’d look at it and say, it’s like a Photoshop tip and it’s five minutes long. And then I would set that aside. Wouldn’t delete it, but like, I’d set it aside. And then I would reset my like new Photoshop document or whatever. And I would record the exact same tutorial again.And I would look at it if the first one was five minutes, the next one was three minutes. And like, and I never wrote a script or anything, but just the action of like doing it twice. It was so much better the second time. And that’s what I found was such an efficient process because, it still came across naturally, but I like avoided the random rabbit holes that I went down the first time where you’re like, you’re talking to, like, this is no longer useful.Should I edit this out later? You know,Charli: [00:53:28]Yeah. Totally. That’s I do that sometimes as well. When it’s more of a, off the cuff video, I’ll, there’s been times where I’ve been like, you know what? I got to the end of my, 30 minutes of footage. And I feel like I should record this again to make the edit process easier. And like, so that I’m more clear on what I said and what I didn’t.Nathan: [00:53:46]Right. Yeah. Cause easier to get clear in the recording in a second than it is for your editor to be like, okay, the three of this plus version four of that one, like there we go. And we’re going to do a jump cut here. So it seems likeCharli: [00:54:01]Yeah.Nathan: [00:54:03]That’d be great. Don’t worry about it. are there times that the full-time role and you know, you’d like your side work as a creator, like those have conflicted?Well, I think that people are wondering like, oh, that’s, that’s great that it magically all works. I’m happy for you. I’m be happy to share examples as well at times, like that with me.Charli: [00:54:21]Yeah.I think that’s a really good question because it is often the impression I think that we give across, or that I give across to people. and I find myself in weird situations where I’m convincing someone that my life is not perfect, which is weird, like find yourself but no, you’re right, totally.There’s I think why it comes across, like it all works is because I lean into the moments when I do feel motivation. And I do have time to like batch film a video. Like I haven’t filmed a video for a month and there’s still been content going out on my YouTube channel because I filmed it when I had time.And when I felt like doing it. but yeah, there’s definitely weeks where. I can’t get what I would like to done on my side hustle, because I know that I have to put my job first and I just have to like, accept that that’s part of the, like, it’s like a compromise you make in deciding to do them both and deciding create on the side means that I’m never gonna be able to produce as much content as someone who does it full-time can, or like take on every opportunity that someone who creates full-time can.And I just have to be okay with that. Right. And if I start to become not okay with that, that’s when I need to like check in with it myself and be like, well, what do I really want to be doing here? Yeah.Nathan: [00:55:36]Yeah. I think that one way that they worked really well together is like different creative energy.Like I’ve spent so much time recently on like, where we’re going as a company, you know, it’s like all these high level things. and very little time, like as a creator, is core to who I am.Like if I were to, you know, write down some identity statement, like writer would be pretty high up in there, you know, writer, designer. and so if I get too far away from that, I find that, You know, I start to feel like disconnected from who, who I am at my core, but at the same time, like ConvertKit as a company does not need me to be a designer like there.In fact, I often cause more problems. If I jumped into let me design this for you. then, Al for someone else on ourCharli: [00:56:28]It’s you didn’t use the design system.Nathan: [00:56:31]Exactly like, hi, let me show you. Remember how I showed you the whole thing and how you didn’t use any of it. And now this is really nice. and so doing something on the side.Yeah. Like I did a, I started a newsletter just talking about money, like, and doing that on the side has been like a really motivating, like get, has given me creative energy, even though it’s an additional thing. The important distinction is that I had to make sure that it wasn’t like a treadmill that I was signing up for. so it’s like going back to, you know, a season of Inside Marketing Design, right? Yeah. I have energy. It’s going to go towards this and then it’s going to go on pause. and then also like setting it up. So it’s, it’s evergreen, right? So instead of sending, a broadcast every Friday morning, you know, I set it up.So it’s an automation and convert kit and, you know, it’s emails one through five and they just go out automatically. And when I have energy, I come in right. And like, you know, the next email is already ready to go and I’m working on one of a few later. and then I know that if at any point I stop, like here’s this asset that people can keep buying or signing up for, and using, and that like it basically the it’ll live on there’s the system itAre there other things where, where you’re doing that or other rules that you have in that.Charli: [00:57:54]Yeah.So maybe a rule that I have is, I was finding myself, spending a lot of time, like reading emails and reading about sponsorship opportunities and like partnership opportunities from companies. And often I would like, feel like I should explore every avenue. Cause like if someone who’s offering to pay me money, right?Like who am I to say no to that? I should do my due diligence and check it out. You’d get a few emails in and it would turn out their idea of a sponsorship was like much lower than what your idea of responses. It was the company wasn’t a good fit, or I don’t know, you didn’t love it. and so I just decided that I’m not going to even entertain the idea of a sponsorship from any company tool, brand, whatever that I don’t already know and use, and like using myself.And that’s just made it really easy. I just have like a text expander auto response that I can just quickly put in to send off to the people who, offer me sponsorships that I, you know, have never heard of before I don’t use.And it, sometimes it hurts to like, think about leaving money on the table in that way, but I just have to hope it pays off longterm in that I’m making those much choices with sponsorships, you know?And that there’s only one of me and I’d rather be creating than emailing a random companyNathan: [00:59:08]Yeah, you made model to help you make that decision and actedAnd freed up. Not only, you know, if people talk about like, you only have so many decisions you can make in a day you know, what font to use for this heading is one of those, you know, like we make a ton of decisions that you’re just like, look, that’s a whole series of decisions that I’m not going to make. And that frees up creative energy for other things. Cause like, should I take the sponsorship or not? It’s not like a creativeCharli: [00:59:37]Yes, exactly.Nathan: [00:59:38]Business admin question, that’s not.Charli: [00:59:41]Yeah. totally. And, another thing that I’m in the middle of right now, I said before the design life podcast is having a summer break. I’m also taking a bit of a summer break from my newsletter, from videos to allow the space to work on season two of Inside Marketing Design. and also to spend some time writing my book, which is completely like fallen by the wayside over the past few months.You know, got out of the habit of it and that’s important to me. So, I don’t have the luxury of being able to do those things as well as continuing with the light content hamster wheel of the other stuff. And so even though it feels like it’s quite a risk, you know, especially in terms of the YouTube algorithm to stop uploading for awhile, it’s what I have to do in order to bring to life this thing that is important to me also.And at the end of the day, that’s, what’s important. Even if my audience on YouTube stays exactly the same and I bring this thing to life, I would rather have that happen than have grown and not made it.Nathan: [01:00:35]Right. Yeah. I see you. Like you’re at 200,000 subscribers now. And what I hear you saying is you’d rather be like, we have this whole string of words that we can use to describe Charli and adding author to that is more important than the next 50,000 YouTube subscribers in 12 months or somethingCharli: [01:00:56]Yes. I would like to say I have a quarter of a million YouTube subscribers. I would really like to say that, but I would much rather say that I’m an author.Nathan: [01:01:06]You’re right.Charli: [01:01:06]I’ll get them both one day.Nathan: [01:01:07]Yeah. Yeah. You’ll get both. It’s just a matter of time. that is an interesting thing. Like if you stay consistent and steady, like so many other things that you want just come with time. so it’s good. Okay. Last thing that I want to ask you about is most people listening to this podcast are going to be newsletter creators, right?So you started on YouTube and went to a newsletter, or added a newsletter in addition, w what would you say to the people who have started with the newsletter? Let’s say they’ve got 10,000 subscribers or 15,000. and they’re thinking about. Going to YouTube in video, especially cause, newsletters, for example, don’t have an algorithm behind it. Right. And so on one hand you’re like, yay. Every, you know, it’s a one-to-one relationship. That’s fantastic. On the other hand, you’re like, Hey, there’s no built-in distribution, there’s no discovery. and so I’m curious what you would say to someone who’s thinking about making them jump over to YouTube.Charli: [01:02:04]First of all, I think. You should do it because when you, when someone sees you on video, they they’ll start to imagine the words that you’re writing in a newsletter in your own voice, you know, as they read it and they’ll make more of a personal connection with you. I think video is so powerful for that.So you know, every creator I think should try and involve video somewhere in, in part of what they make. I think that you should make videos about stuff. That’s a similar topic to your newsletter, to like tie into the audience there. And what’s worked out well for me is having a fairly educational focused video that, is one that.Specifically created to do well in search results, you know, to help people out who are a certain topic, having an opt-in that you offer. And like specifically mentioned it in the video, not just the description, call it out, show a picture of Ronald on screen or whatever. we’ll get the people to join your email list from a video.I found that to be a really good path, lower conversion rate than you might expect, because a lot of people, I know it’s hard to get them to take action from a video, but those who do, if the video is on the same topic as your newsletter, they’ll stick around and become like a good, good audience member for you.Nathan: [01:03:15]Nice. Yeah, that makes sense. I like it. I particularly liked the idea of, you know, switching to video as a media type. Now people will know what you sound like and go through this whole thing.How do you think about, okay, maybe this is a different question.We host craft and commerce every year for ConvertKit, right?Charli: [01:03:37]Well, yeah. Yeah. that justNathan: [01:03:39]Now we’re depressed. But I think about like, let’s say two, the speakers that we’ve had: Casey Neistat and Mark Manson. I imagine they have very—they lead very different lives far as, like, Casey Neistat walks to the airport and mark Manson walks through the airport.They’re going to have very different experiences as far as like number of people who I recognize them. I imagined that the majority of people who have read mark Manson’s books at this point, it’s like 5 million people or 10 million something ridiculous. Right. I have no idea what he looks like.Charli: [01:04:15]Yeah, I didn’t until I saw him at Craft & Commerce.Nathan: [01:04:18]Right. He walks in, you’re like, you know, “Hey, are you, you know…?” He’s like, oh, I’m the keynote speaker or whatever, you know, like great.Charli: [01:04:25]Oh, okay Yeah.Nathan: [01:04:27]Right. Is that something that people should think about, of, I guess the pros and cons of being recognized? Do you have any, any examples or stories of you being recognized?Charli: [01:04:39]I feel like I get recognized sometimes if I’m at a, either a design or a YouTube event. I’ve only had it happen, I think twice that I’ve been recognized just like out on the street.And it was in London, where I was living at the time. And so I don’t know. It’s weird, but I don’t think it should be anything that either deters you or is the reason to make videos, you know?Yeah. I don’t know. It’s, it’s kind of nice and I’ve enjoyed it honestly at design or YouTube events as an introvert; it gives like something to talk about. If someone comes up to you, that means, oh great, I’m not having to approach someone else awkwardly. Someone else has made that, you know, taken on that challenge.And now we get to have a conversation and I can just ask questions about them because they already know about me. If they’ve seen my videos and, that’s just a good situation for me to be in.Nathan: [01:05:28]It is the single best conference hack to have an audience and a persona. And all of that, like the first conference that I ever went to, I think I spoke to two people the entire time, maybe three, maybe, but they were like the person who sat next to me, know, I guess, I dunno, lunch table one, like quietly, you know, when someone said “Hi,” like that kind of thing.And then after I started blogging and went to a conference and like, people were like lining up to talk to me and I wasn’t one of the speakers, you know? And it was just the best hack of like, I hate introducing myself to people and I hate like, You know, all of them, I’ve done it a lot more, you know, the last decade I’ve gotten more comfortable.But yeah, when people just come up and say like, “Oh, Nathan, I love all of your blog posts.” You know, “Charli, I loved your video!” And you’re just like, as an introvert, I guess, “I wanted to meet you, I just didn’t want to have to put in the work.”That’s good.All right. Well maybe we’ll, we’ll leave it there.Where should people go to subscribe and follow all the things that you’re creating on the internet?Charli: [01:06:30]I think the best place would be my website: charlimarie.com. There’s links to my blog posts. Sign up for my newsletter in the footer, the videos, the podcasts, they’re all on there. The font as well, if you want to annotate your designs.Nathan: [01:06:44]Yeah. Buy the font, use it, send a screenshot to Charli.Charli: [01:06:47]Yes. I will re-share it on Twitter. Yeah.Nathan: [01:06:51]I like it. Well, thanks for hanging out. This has been really fun.Charli: [01:06:53]Yeah. Good chat, Nathan.

Robert Glazer is the founder and CEO of Acceleration Partners, a global marketing agency. Robert is also the co-founder and Chairman of BrandCycle, an affiliate marketing and content monetization platform.Acceleration’s accolades under Robert’s direction include Glassdoor’s Employees’ Choice Awards, Entrepreneur’s Top Company Culture, Inc. Magazine’s Best Place to Work, and Fortune’s Best Small & Medium Workplaces. Robert is also the international bestselling author of four books: Elevate, Friday Forward, Performance Partnerships, and How To Thrive In The Virtual Workplace.With a passion for helping entrepreneurs and organizations achieve success, Robert shares his insights in Friday Forward, an inspirational weekly newsletter reaching over 200,000 individuals and business leaders across 60+ countries. He is also a regular columnist for Forbes, Inc. and Entrepreneur on the subjects of performance marketing and entrepreneurship, company culture, hiring, and leadership.Robert enjoys speaking on business growth, culture, mindful transitions, building capacity and performance, and spends his spare time skiing, cycling, reading, traveling, renovating his home, and spending time with his family.In this episode, you’ll learn: The most important component for maximizing your content’s reach The necessity of giving your audience direct access to you Why the culture of your organization or brand is so important Links & Resources Entrepreneurs' Organization “This Is the Only Newsletter I Always Read. Here's Why” Rad Reads Friday Four James Clear “How a CEO’s Inspirational Emails Got a Worldwide Following” Benjamin Hardy Tim Ferriss Malcolm Gladwell Danielle Steel Robert Glazer’s Links Robert Glazer’s website Friday Forward Elevate Podcast Acceleration Partners Books by Robert Glazer Robert’s Twitter Episode TranscriptRobert: [00:00:00]Here’s how you should think about what is a mistake that you have permission to make: one of the things that was really helpful is we shared with the team a picture of a boat with a waterline, and said, “Look, the below-the-waterline stuff is going to sink the boat, the stuff that’s above the waterline, that’s not going to stink the ship. Let’s make mistakes, learn from them, and not make them again. What we really need you to do is watch the waterline.”Nathan: [00:00:31]In this episode, I talk to Robert Glazer, who built a newsletter called Friday Forward to a couple hundred thousand subscribers, which is really impressive.But then he also did it while running a full-time business while running a team of over 200 people. They’re growing really quickly. The company is called the Acceleration Partners, and they are an agency that works with all the biggest affiliate programs out there. So it’s fascinating the way that he took the content, the way that he republished on LinkedIn and wrote for Forbes, and, Inc., and others.We also get into other things like company culture. He runs a virtual team. We get into why he writes books and produces courses even as he’s running a multi-million dollar company. A lot of interesting things. There are questions that I’m asking kind of really for myself, because he has this interesting split of content creator and CEO, that I try to find that balance and walk that line as well.It’s a phone conversation. We've been friends for a long time and, haven’t caught up in quite a while. So, it’s just fun to chat.I hope you enjoy the episode.Bob. Welcome to the show.Robert: [00:01:34]Good to be here.Nathan: [00:01:36]So I actually haven’t talked to you in a long time. I was just thinking back to,Robert: [00:01:41]Pre-COVID probably. And then we reallyNathan: [00:01:43]Yeah, exactly. But we’ve had so many good conversations, like a few interesting things that we have in common is both running good sized firms, like as CEOs, and then also loving content creation and loving this side of it. So, I want to talk about all kinds of stuff related to that. But first, your newsletter Friday Forward, like, will you just tell high-level where that came from?Because as I understand it, you didn’t set out to start a newsletter. You set out to create content for your team.Robert: [00:02:12]Yeah, and even set out to work on my morning routine. So, I actually had come from a leadership event, pretty intensive event that Entrepreneur’s Organization had put on. I think it’s until I started a long time. And then you realize you’ve got to change your dates like five, seven years ago now.The real focus is on the morning routine, not the real focus, a big focus was on a morning routine, starting off the days. Because, you know, time for thoughtful reflection, reading something positive writing, which is a great routine for a creator anyway. And, we were given some stuff to read.It was a little too like rainbow and unicorny like, “You can do it!” quotes. Like it wasn’t my cup of tea. And so I, when I got back and I continued through the routine, I was like, you know what, maybe, maybe I’ll combine these activities. I have some stories that I like and some quotes and some things in this folder.Like, so I thought like our team was like 40 at the time, I think maybe 45 and we’re all distributed. We’ve always been virtual. And so I was like, I’ll just start writing this note to the team on Fridays. And it won’t be about our business or anything. It’ll be about a story or something kind of inspirational and motivational getting better.Started sending these things, I changed the name a few times. For a couple of months I didn’t think anyone was reading them. Then I did get some notes back saying, you know what, I did this thing, you talked about three or four weeks ago, or, “Thanks, that was really helpful.” And the other curious thing was I got notes like, “Hey, I shared this with my wife’s company,” or, you know, “My brother shared this with his family. He loves it. I’ve been sending it to him.”So, I was actually at another EO conference a couple months later talking with some other CEOs about like, this is, this has been really good. It’s been good for me. It makes me think about something, right.It’s been a great way to connect to the team. You know, you, you should all try this. And they said, Oh yeah, well, send us yours.” So, I sent it to four or five of them and like good entrepreneurs, like one started his own and did it this year. And the other said, “This is great. We’ll just send this stuff to our teams! This is super helpful!”So, at that point I was like, huh, I wonder if this people would be interested outside. I did not know about a ConvertKit at the time. So I, I found sort of a, a newsletter service that would just look as much like a plain email as possible. Cause I was doing this all via BCC.I threw like a couple hundred friends on it and family and other people. I expected like, “What the hell is this?” (unsubscribe). And, I just kept getting nice notes, and people were sharing it. Someone posted something on Inc. “This is the only newsletter I read.” And 2000 people signed up that day and now it’s like a couple hundred thousand people in 60 countries and it’s totally crazy.Nathan: [00:04:43]That’s yeah, that’s wild. I’m realizing that a lot of these newsletters. Are really high quality and people love start with something random like that. Like I think of, my friend Kay, who runs Rad Reads,like he started that, it was just like, here’s some links for some friends, you know? And it, it starts in that really simple.I love the idea of the CEO being like, “Yeah, I should have… wait, how about, instead of me writing it, you just write it?”Robert: [00:05:11]Well, th th there’s a phrase in EO or it called R and D, which is rip off and duplicate, which is, so yeah, they were like, this is good. This is my team will love this. Just send it to me on Fridays. and it made me that way in the slack channel and all that stuff.So, yeah,Nathan: [00:05:26]What are some of the things like as we fast forward, what are some of the opportunities and things like or favorite moments that have come from having the newsletter and then we can back it upRobert: [00:05:34]It’s, it is nothing about my business. And I actually got pressure from our team to be like, Hey, shouldn’t this be like under our brand or otherwise? And I think there’s people that I, I w my agency, you know, we run affiliate marketing agency. A lot of times people ask for advice.What kind of blog or things should I write to make money? I’m like, it kind of doesn’t work like that. Like these people, like this guy loves grills, this woman loves whatever. Like they, they get a following because they love the content they want to write about everyday. Then they think about monetization.I think, you know, something like Friday four to probably other ones that work. Like I just tried to create value for the reader every week. If I had had an ulterior motive, then I think the content wouldn’t have been good and it wouldn’t have spread. So it’s led to all kinds of discussions speaking all around the world, you know, my, my two books, for sure.And just, you know, a lot of times. Again, probably forward, like you would never know in a million years what I did or what my business did, but I will get an introduction to our business from a Friday Forward because it’s, I’m just in that person’s inbox every Friday. Like that’s the mental trigger, not, not the marketing content that we put out, like all over the place.So that’s kind of been an interesting learning for me. because again, it, well, it’s totally separate. There’s clearly been a, a nice halo effect,Nathan: [00:06:54]Yeah. Are there, does that happen a lot of business coming from Friday Forward or is it more just the, kind of the rising tide.Robert: [00:07:05]It happens a fair amount. And I will say a lot of times I’m reaching out to a client or prospect or partner in our industry and they will say. Something about love that Friday Forward or otherwise. I was actually an industry conference, PC pre COVID. And cause at the time some of this, we put out a ton of content or industry, like the best content or industry.We have an industry book or otherwise, and I’m walking around the big event party, like the night with all the people in our industry and people coming up and saying, Hannah, like, I love that Friday for four weeks ago. I loved that one too much. Like, no one’s talking about the five reasons to start an affiliate pro like I just thought it was like an interesting thing where, you know, no one for all the content we have those industry wise that wasn’t what anyone was talking to me about.Nathan: [00:07:48]Yeah, I was, I was thinking about, James clear is someone who I’ve been friends with for a long time and, and got to watch him build his newsletter. And he got to this point. Yeah. It was probably around maybe 50, a hundred thousand subscribers where he realized the level of person that was following and reading his stuff was like, he would reach out of, Hey, could I, could we do this?He’s got this long shot. Like, can I get an introductionRobert: [00:08:13]Yeah. And they thought he was like this, this amazing.Nathan: [00:08:17]Yeah, exactly. And they were like, oh, I’m already subscribed. You know? Like, and so I imagine you had the same kind of thing,Robert: [00:08:23]I actually, I, I do a hundred day check-ins with our clients and there’s a really big global client we saw, like in the news all the day and she’s like, oh, I’ve been a reader of your Friday, Ford for years. and so the sales team didn’t know that no one knew that, but, but you know, I, I have to think that that factored into the decision making process, even though again, has nothing to do with what it is that we do.She’s like, I used to listen to it on the tube to work, read it on the tube to work every Friday.Nathan: [00:08:49]Hmm. Do you do anything specific? Like to try to understand who’s subscribed to it. Like I know James at one point with his newsletter, like specifically, I don’t know how he did it, but he went and looked through it to find like what, which NFL teams were like had coaches that were subscribed or any of those.Robert: [00:09:07]All right. I’ll give you some product, you know, a feature or things that would help with this if you want them. But yeah, a lot of times I’d store by, I sort by, one of the tools that really helped me with sorting by most opened by person. And then when I opened that in the thing, it would show me, I could clearly see it was being spread around a company because that person’s copy of it was being opened in 200 cities around world.So, that would actually tip me off that it was like a company. And then I might go look at that company’s URL in the, in the sort of subscriber list and see if there are a bunch of people from that company. But that’s also be an awesome feature to try to join together, like a company statistic and show people or some sort of heat map about like, who’s opening it.But I, I, I, that is the one thing I do. I look every week at the total number of opens by it subscriber because it gives me a sense of if it’s being forwarded beyond the initial open. And then like, if someone has a 2000 next to them, like they’ve sent this to a lot of people. And so it’s just sort of a mental note in my head.Nathan: [00:10:12]That’s interesting. I like that. okay. So let’s talk about how the newsletter group, cause obviously going from, you know, a couple hundred people to a couple hundred thousand people is a lot of work. We don’t want to be hand-wavy about it. There’s, there’s a lot in that maybe like from that 300 people to say the first five or 10,000, did that part of the journey look like?Robert: [00:10:35]Yeah. So, look at, once it started getting momentum, there were a couple articles, there was a Boston globe article. There was an ink article kind of, again, this is the newsletter. I read saw some big bumps on that. anyone who emailed me, you know, it would be added to the list, you know, so I was good about anyone that I interacted with would make the cut.I actually had a tool that would scrape my inbox and do that, which is pretty cool. you know, because, and, and, and, and thinking through LinkedIn. So I was good about making sure that people I were connected to were on it. And then I started to just think more about touch points, you know, in terms of, if someone was doing a we’d sign them up for bee.I think that’s, you know, that’s something I focused on as the list has gotten bigger, but I really, I also, because it was being forwarded a lot, I tried, and I, you know, stole some, I ripped off a duplicate, like just, I tried to be clever with the lions around. Hey, you’re stealing this copy from someone else and it’s free, like sign up to get inside to get your run.So I tried to make sure that the people that were reading it or got forwarded one knew it was like a newsletter that they could get every week and try to get them to sign up. And, the other thing I was really good about is I would syndicate them on LinkedIn or I post on LinkedIn and I’d always say at the bottom, Hey, this is part of my Friday Ford series.You can sign up here and that actually generated a fair enough look, LinkedIn is one of the few media syndication things that lets you, you know, they’re not paying you to do, it’s not ink, it’s your channel. So I think the thing that people forget is they they’re, you can, you know, you can really actively drive signups to, to a newsletter list from LinkedIn.Nathan: [00:12:15]Yeah. And I remember when we were talking. In a long Uber ride from in park city. I think that something like that doesn’t surprise by it is that LinkedIn was driving a good number of subscribers for you. Was there a particular strategy there or are you just recently getting the content?Robert: [00:12:34]Look, luck is as good as strategy. So I got timing. I was one of the first ones to have the newsletter series and the subscribe button. Plus at the time I was part of a small group where LinkedIn was boosting the content. So I would publish an article. People would see the subscribe button and it would go out to hundreds of thousands of people.And I made sure to let them know that again, I think with a newsletter, when someone forwards a newsletter, the person receiving it could assume like this is a one-time thing, but if they really love the writing, like someone did all of his articles yesterday, brilliant thing, the person wrote. Yeah. At the end of the day, it said some, not this isn’t the language, but like I write things like this all the time, you know, get them directly here.I probably, I probably would have done that, but I don’t, I don’t think people think to think to do that as much. So, you know, if you, if you publish on or you publish on forums, is there any of these things? They really don’t let you drive to your newsletter list, but things like medium and Quora and LinkedIn, you know, you can, you can very easily drive to your own list.Nathan: [00:13:34]Do you think that, like that opportunity, obviously you timed timed it well through you don’t lock in that timing.Robert: [00:13:41]Yeah. I don’t know if it would work the same today, but that’s true for any of the channels as they’re taking off, right?Nathan: [00:13:46]Right. But the, the republishing idea is interesting because a lot of people will say like, no, I want that content on my own site. And I’m using James as an example. Again, that’s something that he did in his first business. He did a lot of like, he would write guest posts for everything. And then in, for James clear.com, he took the approach of saying, I’m going to only like the original content goes on my site, but I’ll resyndicate it, you know, Quora, medium LinkedIn, anywhere else.Robert: [00:14:12]Yeah, syndication thing. And again, I mean, I’ve done, I have columns on Inc and Forbes and you just, you can’t link to yourself. Right? So, I, if I put something on there, I have take it all out. what, if you put on LinkedIn core, medium, you can link to your own books, your own material, your own newsletters.So, I think there’s some positive value of that from an SEO standpoint, in terms of also putting it on your own site and getting people to link into that, that article. But, you know, I, I consider LinkedIn a great way to build like your own audience on LinkedIn. I mean, I think, I actually think the distribution of five forward is probably bigger on LinkedIn than it is the email just based on my subscriber count there.Nathan: [00:14:54]Interesting. Okay. I also realized I finally accepted your LinkedIn request from three yearsRobert: [00:15:00]I’ve been sitting there every day. for two years. Sounds like, what did I, how did I offend them? Like, I don’t.Nathan: [00:15:09]So, the, the Forbes and Inc like those columns, are you getting a good amount of like a good amount of additional attention from them? Like how do you think about that in your content strategy?Robert: [00:15:20]Yeah. I, I, I think to me, those, I try to focus on things there that where the authority is helpful. Right. I, I think where you’re writing a definitive piece. So like, for example, my, you know, you can syndicate anything on thereafter two weeks too, but, but when I’m coming out with the remote book, like the three things to, you know, ask your employer about remote work.I think if you’re sharing that with people or otherwise, there is an authority aspect of, of, of, of an anchor forms. One thing I’ve noticed though, and I, I don’t know how this impacting the stats though, the sites have really pushing towards log-in and paywall. like, this is a lot of stuff going on and I have a feeling like it’s probably reducing.Readership because even mean, even I now want to go read my article, you know, it’s like, you can, you got to get a subscription. So I assume that’s more limiting these days.Nathan: [00:16:17]We ran into that. When, earlier this year we acquired a company called fan bread, which is, email marketing for musicians and billboard covered the. Did, you know, broke the story, but it was behind a paywall and we were like, come on. You know? And so we emailed them in like an hour or two later.They’re like, okay, we’ll take it out from behind the paywall. But you run into that where you want the name brand, or you’re like, oh look, Inc. You know, or, you know, for like like a piece of content, but, but you’re right. It gets really hard when it’s bound to pay. Well,Robert: [00:16:47]Look, and I, I feel that like everyone needs a business model. No, you know what it is, but I, I, there’s a, there’s a, or like large, global newspaper I write for. And they asked me to work on a series of something I sent to them and they sent me the article I wrote back. And he, the guy was really receptive to the feedback.And I was like, honestly, I was like, I wouldn’t read this article. I feel like I’m being attacked by your banner ads. There is a full-size one, there’s a blinking one. There’s a video playing, this is terrible user experience. Like I can’t even find the content. And like, I know you have to make money, but like, you guys are a prestigious, like big, like this is horrible.I it’s just. I was like, and look, we know a lot of this from the affiliate space, Stu I’m like, look at what CNN and Buzzfeed and these folks are doing. I mean, they’re, they’re, they’re trying to tie, you know, write really good content. Then, then, you know, linked to the things are linked to the relevant things or put it in the text so that if you’re talking about this thing, buy it and make some money that way.But because a lot of these are just Google display ads, but it was really like, I actually felt like I was under attack, like on, on the page. And I was like, this is not the future. And he was, he was very receptive. He’s like, I know it’s bad. I’m like, I’m just not sure that putting a hundred display ads on a page is actually going to make you more money than putting the one or two right.Things that are contextual what’s beingNathan: [00:18:06]Yeah. Yeah, absolutely. So when you’re writing, like what’s the relationship between say Friday Forward and, like what you write for Forbes or Inc. Is it Reese indicated? Is it a version of the story that you then write differently?Robert: [00:18:23]Yeah. I have taken Friday Fords and adapted them to like ink or Forbes. not that often, like those need a kind of like 1, 2, 3 format and they really don’t want you to talk about yourself. And actually Friday before it usually has personal anecdotes, but like on occasion, like if there’s a concept that’s really good.I will rework that into that structure. But, but you know, the thing that I’ve come to understand from, from James and from other people, and I, I used to be from Ben Hardy. Like I used to be a little more, but like the title really matters. Like, I, I, it, you know, it, it feels like you’re being a little mark, but if you write a so-so title, the way the algorithm work, no, one’s going to read the thing.So I, I think as a writer, you have to flip your brain on this and say, like, not that you should have a bait and switch title or sensational, but increase to send me the top 10 titles every month. And it’s really clear the number one thing that the top two that, because either you see it and you read it now and it gets positive algorithm velocity, or if you think that I don’t need to read that now.And it doesn’t get momentum quickly, it drops to the bottom of the pile. So. You know, I have an editor and a title. I I’ll push them. And I’m like warm cup of tea. That’s one of my edits. Someone said that to me, once about my writing, like I was like, this feels like a warm cup of tea that you don’t need to re like.And, and I think as a writer, I actually think everyone needs to embrace that a little bit. Your, your titles, they shouldn’t be beat and switchy. They shouldn’t be national Enquirer, but they, they kind of need to make people want to read it now.Nathan: [00:19:54]So, yeah, I’m definitely guilty of that. Of all. I’ll write a 3000 word article that I’m really proud of. This is one of the things that I’m always going to refer back to, and then I’m like, oh, and the title, there we go. Yep. That’ll work for the deadline. You just kind of move on and then you realize like, wait, why didn’t people read it?Robert: [00:20:11]Right. And what we, we operate in this world, what goes up, it goes into feeds and like the stuff that’s quickly looked at and clicked on and acted upon rises to the stop. And so you’re talking about four to five times, probably the number of people that would read your article with the right title and by, and by the way, ink, ink forces AB titling.And I would tell you that I am, I am wrong more than ha like so wrong at, which is the, which would be the more effective title, which shows why it’s in the testing is, is interesting. But every time I get the top lists again, it sounds as if they are all, you know, you won’t believe why Delta airlines is firing all of its pilots, or this is the number one thing that all successful things haven’t caught.Like those are the ones that are constantly the most read articles.Nathan: [00:20:57]Yeah. Okay. So I want to ask about writing process because showing up, like when you’re running a company and you’ve got a substantial team now and all that.Robert: [00:21:06]Yeah.Nathan: [00:21:07]And showing up every week and like writing good, original content that people want to forward and share with, you know, with their teams and everything else.That’s hard to do. So tell me about your process for producing that quality content on The Nathan Barry Show – 044 – Nathan Barry_PROCESSED: [00:21:19] aNathan: [00:21:19]Consistent basis.Robert: [00:21:21]Yeah. So Friday Forward, I have a very good editor on my team, worked on them for two years. He could probably write an article and I couldn’t have told you, you know, if my, I mean, he knows my voice at this point, but, I once had someone write me on Friday at four and say, whatever you pay people to write these for you, like it’s worth it.And I was like, thanks, dude. Like I write them out. so, yeah, I will draft it. Like I can draft a thousand words pretty fast. It’ll just be a mess. Like it takes me four times as long to edit versus a good editor is like, can he edit and half an hour? What would take, take him four hours to write it? And it would take me, you know, four hours to edit it.So, I try to just get out that kind of concept draft quickly on Friday Forward. I usually get one, get one big edit back and then we’ll do one or two reds on tweaking. It’s kind of like, it just meant, like I write it on Sunday or Monday, Tuesdays edit day Wednesday, we set it up. It needs to go out by, 1:00 PM on Thursday.Cause that’s 7:00 AM. New Zealand on Friday, I which is the first, the first 7:00 AM. so, that’s the process on Friday Forward on other things I I’ve actually with the editor sort of embrace the scribe process. So, so like I did that this morning, which is, I said, look, here’s an article.I think we should write. Here’s the title kind of intro concept, main three points and I’ll, I’ll bullet it all out and I’ll say, we need, we need a data point on this or that. And I may even like audio record. A minute on it and then they’ll draft it up for me and actually works really well. and in terms of, cause sometimes it’s like, I think this is the point we want to make, but let’s see if we can find a stat that backs this up.So they’re always, my idea is it’s always my, you know, you know, framework, but I I’ve always leaned heavily on editors because I can spit out a lot quickly. And then to say, can you please take this mess and help me clean it up a little bit?Nathan: [00:23:21]Yeah. how do you go about finding an editor for that? Like you obviously have an editor that you’ve had a long long-termRobert: [00:23:28]Yeah. I’ve worked with different people. I, it takes about six months, I think to really get one of the things I would suggest is if you start working with the editor is really used track team. And this is like the same thing at delegation. Like when I would change something, I would explain why I was changing it.Right. Like I never used say always and never in my writing. I don’t want to say anything that can be disproven. Right. So I would always like go the ex like I make comments about why would like never use, like, if you can use such as right. so try to develop those rules so that as they’re editing, they really like understand my tone and my language. and that sounds awful.Nathan: [00:24:08]Does that end up going into a, you know, a standard operating procedure for how to write light bulb?Robert: [00:24:15]I think so. I haven’t seen it, but I actually think they have it, but that’s, I, I should check that, that we have that, but yeah, it probably has sort of like a, whatever those guides are, those standardized guides, right. Of like re what is the Bob ism? And it’s not proper English or grammar. It’s just, it’s funny.I always feel like, you know, something, this is a delegation, you know, something by God, but when someone forces you to explain it, what it is, it’s actually really helpful from a training standpoint. Like, I don’t like the sentence. Well, why? Because it says something that can be disproven. Right. So then, then you realize, oh, that’s really the, that’s really the core thing that the editor could, could learn from.Nathan: [00:24:53]Okay. So I have to ask you about saying something that can be disproven. Like there’s other writers that would be really trying to have like concrete statements, you know, and all that. So why, why are you on the other side of, of trying to specifically avoid that?Robert: [00:25:08]Well there’s opinion, in fact, right? So your opinion can be argued, but I don’t like to say, like, I think, for example, let’s say, I said like, you know, all email marketing, CRM companies, like make this mistake right. Or make this same mistake. Well then, you know, Nathan comes along and publishes an article and says, we absolutely don’t that.Right. I could write an opinion that says, you know, I think the vast majority, like, or something like, but, but, but actually I think it actually hurts your credibility. If you state something as an absolute, that someone can disprove that you can have a theory, you can have an opinion, you’ve got whatever they have can be disproven.Like for example, I have a, an opinion that you should never make counteroffers like in, in a business now. but if I said that counter offers never worked. That would be, someone would be like no work and I’d be like, no, but actually you’re proving my point. They work one out of 10 times. and so my point is that, why would you do anything that works one out of 10 times?What you’re all going to do is you’re going to tell me about those one out of 10, and you’re never going to talk about the nine out of 10. So we just do it as a rule because we know it has a 10% acceptance rate. So that’s the difference between stating that as like a fact that that is a proof point versus an opinion.Nathan: [00:26:23]That makes sense. I’m tracking with that. Cause people always latch on to like, oh, let me find the one exception to prove you wrong.Robert: [00:26:29]Correct. They’ll attack back and then there’ll be right, because they’ll post they’ll find the thing. Like here’s an example of what’s, like I even said, I knew it was going to happen and it was actually kind of funny, but in one of my Friday Forwards, I was talking about progress and like innovation. I was like, look, if you’re the best run horse and buggy shop in America, you know, you probably don’t have a great business.And so of course, someone sends me this horse and buggy shop in Lancaster, Pennsylvania in Amish country. I’m like, yeah. And do it. I know there’s like two of them, but like that wasn’t the, that wasn’t the point of the article.Nathan: [00:27:00]Yeah. that, makes sense. I want to ask about is the PR side, like how, cause you talked about in the early days. Getting some, like the, the newsletter mentioned in different press publications, stuff like that. What is your PR strategy? How does that fit into the growth of it? Or is it all just kind of organic and, and whatever comes.Robert: [00:27:21]Yeah, we we’ve tried PR over the time. What’s interesting is that we have found that a lot of the PR in our industry has not been very valuable. Like it’s just people know it’s our industry. If they want to talk about our industry, they’ll find us. They’ll include us in something like, it’s not, it’s still not a widely discuss thing, but, but actually these other stories tend to get picked up more like Acceleration Partners does a pay $500 to, for people to go on vacation and not check their email.Right. Or, you know, founder wrote this email and now 200,000 people read it. So, so it’s actually some of these other things that have gotten us kind of more, I’m still not convinced you can, it’s really hard to measure any of this stuff. So I’d rather get it organically, you know, do an hour. No. What wastes my time that to pay someone five or $10,000 a month to, to not actually be able to.Measure what, what we’re getting from that, I I’ve continually been disappointed with our corporate PR efforts, unless they are super targeted on an award and industry thing or something like that. You just, you know, if someone writes about how our industry is changing and we are changing, our industry is the wall street journal cover story.Like that’s going to help our business. But every article where Robert Glazer weighs in with one line, like we operate in partner performance, outcome marketing. So I’m always thinking about how is someone going to go from that article to researching my business, the buyer they’re never going to like it.So it might make us feel good that my name was in there, but I had to bet any amount of money that this would lead to business. The answer is no.Nathan: [00:29:02]Okay, that makes sense. And that’s kind of the way that I’ve thought about it as well. And I’ve seen these like ancillary things we picked up so much moreRobert: [00:29:09]Yeah, and those, those are free, right? You almost just get those from doing this stuff and people hearing about the policy at your company or, or, you know, people writing about this really cool thing that, you know, convert kids doing. And then someone says, oh, I need a new email company. So I like what they’re doing.And I respect that. Right. Versus like, again, if you tried to pitch the wall street journal on email marketing stories, I think you’d be, you know, wildly underwhelmed with the results that you’d probably get.Nathan: [00:29:38]Yeah.Robert: [00:29:38]I also think people had a really hard time in the last 24 months getting any PR any mass market TV PR outside of things related to the election, social justice.And COVID right. It’s anyone I’ve known as launched a book has had no success with mass market PR in the last 24 months. They just can’t get them to talk about this stuff.Nathan: [00:30:02]Yeah. So speaking of books and courses, you’ve got a few of each, and I’m curious, like when you set out to write a book or produce a course, what’s the, what’s the thing that you’re optimizing for in that? Like, is itRobert: [00:30:17]Probably probably a good question to ask for before I, started on that process. yeah, so I I’m optimizing really for my sort of why and purpose, which is to like share ideas that help people in organizations grow. That’s, that’s sort of my core purpose. That’s why when I figure out something I kind of wanna like crowdsource it.So, I’m thinking about what makes, you know, the, the, the impact, I think, as you know, like, and I’ve read a bunch of your stuff, like a book is sort of. The top of the tent, but really like if you’re not, Lane’s not like Tim Ferriss or Malcolm Gladwell or Danielle Steele, like you’re just not going to make a living off of, off of, writing books.And so if you do want there to be something that is more revenue generating, generating under that, then you’ve got to have sort of a logical thing that, that comes next then, you know, in talking to a lot of people and back to that sort of teaching thing, realizing that also the thing about books is particularly a global books, which might like I get the data six months later.Like I work in affiliate where we get everything real time around the world, and then the book data that you get six months later. so it’s been really interesting about courses is that, Look, if a book changed someone’s life, they might still not pay $30 more for me to, if I told you there was an app that was $9, you’d be like, oh God, a $9 app, but you’d go buy a $14 IPA, you know, this afternoon.No problem. So something about book has a limiting price structure and, and, and if you work with a publisher, you’re going to make like a buck or two a copy. so, but, but, but a a hundred dollars course sounds reasonable or a $500 course sounds reasonable. The margins are great and you get all of the data, you know, in real time.So, and I think the most important thing, and look, I learned this from the pandemic a little bit, and, and, and DTC. So think about the restaurants during the pandemic. So there were restaurants that had loyalty programs, knew their customers, all this stuff could reach out to them, could let them know that they were doing delivery.They were doing wholesale drops your kids. There are other restaurants that were packed every day of the week, who had no idea. They know you need the, Hey, Nathan, but I don’t know how to, how to get in touch with Nathan. Right? So, so I think it’s critical these days, whether it’s a course, a download or something, like if someone loves your book and your content, like you want a direct connection to that person, as best as you can.Nathan: [00:32:45]Yeah. And I mean, we saw that all across the board, in the pandemic of like, it kind of flipped, which businessesRobert: [00:32:51]Right?Nathan: [00:32:51]Well, and there were a lot that we’re doing.Robert: [00:32:53]The businesses that knew their customers were like 10 X better off than the businessesNathan: [00:32:58]Yeah, for sure. So when we think about putting out a course, the question that I have on, on the revenue side is right. You run a substantial business already. And so how do you think about it? W, the revenue from courses, is that, is that meaningful? Is that just like, you’re trying to get the ideas out there and it’s nice to get paid for it so that it pays back the production costs or is that like actually, a revenue stream that you track and are interested in growing?Robert: [00:33:25]I think it’s a little bit B plus C like in terms of like one of the things people don’t realize, I think people will get used to Friday for being free. You know, other stuff like I, you know, I offered when people bought the book, I think this is the creator conundrum of, of sometimes like, you know, I offered either you bought the nine, nine, said he booked during launch week, or you bought the full price, audio book or whatever book.And I gave you the $8 course for free. So of course I had three people, you know, say if I buy the 99 cent ebook, will you give me the $80 course for free? I’ve been delivering value to you for like three years. Like it’s too much to ask for like $5. Like it’s just sort of, you know, it’s insulting at the end of the day.So, I think it’s, I think it’s important to establish, Pete Vargas has sort of influenced me on this a little bit in terms of the, you know, w w w what is the sort of one to many versus done with you versus one-to-one? I think there’s an assumption that you are just out there doing this, you know, and available for anything I’m in and people asking me, can you come talk about this to my forum?Can you come do this? And then it’s like, you don’t kind of ask a lawyer for free legal advice. So, so I do think it is important to sort of establish like, Hey, the book might be X, but, you know, speaking has a price. This has a price. The content has sort of price. Yeah, I’m not, I’m not looking to retire on it, but I would like to cover the costs of a lot of, you know, and there’s a lot of costs and a content produce content produce a podcasts.But, over time, that would be a good income stream to have, like, to me, it’s the win-win, is there something I can deliver to people of real value that they can get, like the core value, of course, when they come out of that and they see that was life changing and you know, that can also be profitable.Like that would be great. because I think sometimes we have our profit and one place and our passion and the other, and I always say don’t people are really jealous of the world or golfers because. The guy made $3 million and won the masters on Sunday. He just wants to go do the same thing on Monday.Right. So if you can, if you can add value, connect with people and they’re happy to exchange like a fee for that, like then that’s, that’s sustainable. But I do think people sort of also get into that example. Don’t underestimate like what it costs and just, you know, you have a couple of hundred thousand person email list and a podcast and this service, and then that’s 10 bucks a month.Like the free newsletter could be a fair amount of money.Nathan: [00:35:54]Yeah. I mean, as the way I, that I know since the free newsletter is what drives my business,Robert: [00:36:00]Yeah.Nathan: [00:36:00]I know it can be quite a bit of money.Robert: [00:36:02]So if you own a newsletter company, so, you know,Nathan: [00:36:05]Yep, exactly.Robert: [00:36:07]Well, I thought I actually was reading some strategies last week on also people want to dialogue, they want to write, you know, me, it’s like, it’s a lot of people. Like I, I’m starting to envision what more of a premium community looks like. And again, to sort of bifurcate and say, I don’t think I want to charge for the newsletter, but if you want to talk about this, if you want advice or otherwise, like, I can’t, I, you know, for what I charge an hour for, like, I can’t, like, I can’t just be on the hook for everyone in the world to do that with them.So I I’ve, I’ve been open. Look, I’d be curious to your thoughts. I’ve been thinking about what is, what does that look like? I’m not sure I want to charge for the newsletter. but, but how do I have sort of a, a premium group of people who would like access or more dialogue and that, but, but that has to have some cost to it.Nathan: [00:36:52]Yeah, well, there’s a lot of people doing this, with their newsletters. And so I think it’s a good, a good model actually. there’s a startup called circle, that I invested in another set of like basically making this it’s effectively like community forums type software, but like a modern, modern version of it, and that works really well. Like here’s the newsletter. And then if you want to pay a hundred dollars a year, $25 a month, like any, anything, any version of that, a couple of things you don’t want to make a new treadmill for yourself, right? You have a treadmill that’s working very well. I tried to not has a negative connotation.Friday Forward isRobert: [00:37:33]Yeah.Nathan: [00:37:33]For you. It’s just a very effective treadmill. And so be careful to make another thing that you have to show up for and you have that obligation. Cause you don’t want to end up hating that. And so I would really make it about the connection to other people. And when you show up, that’s a bonus. because then people are like, who else reads Friday for who else is the biggest fan of Friday forRobert: [00:37:57]We tested it. Yeah. And we tested that. That’s what we played around with, with a free Facebook group. So I think we were going down that route. So that was good. Good advice.Nathan: [00:38:05]And then, then you can show up and it’s fun because it’s not an obligation. And then, you know, you show up every week or every month or whatever, andRobert: [00:38:12]That’s icing. Not, not cake.Nathan: [00:38:14]Yeah, exactly. So that’s the biggest thing. and then I would charge enough, especially cause you’re in the business market. Like whenever I see people putting these things out and it’s like $5 a month, you know, orRobert: [00:38:26]Yeah.Nathan: [00:38:27]Even $10 a month, just like, that’s not, that’s not enough. Like I would probably be.Robert: [00:38:32]I would say by you need, buy-in like, I, I very rarely give away things for free, even if I would want to, because I think that person’s not going to follow through. They’re not going show up. I, I won’t, I won’t, I won’t do speaking for free events for the most part, because I think the, you know, those people will tell you that there’s 2000 people coming and they’ll get 200 becauseNathan: [00:38:52]Right.Robert: [00:38:53]There’s no, skin in the game.Nathan: [00:38:54]Yeah. So I would do something like $500 a year as the price point, because then people are saying like, okay, I’m committing for a year. it’s like a substantial amount of money. You know, it’s not quite an impulse buy. It sets the barrier, like the bottom end of who’s going to, to sign up right. Someone who isn’t going to pay $500 a year to like troll your community, you know? And so it also sends a signal to everyone, like, okay, people who do this are going to be going to be invested and also turn on, on like membership style. Content is super high compared to software and specific. You know, in that sense.And so going in annual plan is going to cut down on significant churn and you have time to deliver value. Whereas if you like, or the pay newsletter that’s monthly or something like that,Robert: [00:39:43]Right. People don’t get value for two months. They’re on vacation and then they’ll turn it off. Yeah.I mean, do you say if you got to pay this interest, I mean, I went through all these, I read all the articles and you probably have some good ones. If you go to paid, you probably got to cut your audience 90%.So, you could argue those are the people that, that, that, that, that really matter. but, again, I think it’s more of like, what could you give the 10% that is above and beyond that rather than cuttingNathan: [00:40:07]Yep.Robert: [00:40:08]The 90%? Yeah.Nathan: [00:40:09]Yeah. And I think that’s the way to go of adding something for, for the premiums side. I actually, yesterday launched a hobby paid newsletter. I made it just a hundred bucks one time, like a one-time payment. And really, I wanted to write about like, what creators should do after that. Made the bar set was $200,000 a year.Like I’ve doneRobert: [00:40:30]Yeah.Nathan: [00:40:30]Writing about how to get to that point and that everyoneRobert: [00:40:34]Yeah,Nathan: [00:40:34]Gets there, which is amazing, then they’re like, what do I do now?Robert: [00:40:38]Or you should do like an NFT blockchain thing on it. So you sell a hundred, a hundred dollars subscriptions and that’s all you’re going to sell. Right. So then maybe they have like, they actually have to, you have to buy into it, right. If you want to get into, like, they could actually increase in value.Nathan: [00:40:52]That’s right.Robert: [00:40:53]It’s not this guy I’ve seen dumber ideas.Yeah.Nathan: [00:40:55]Oh man. I’ve seen so many dumb ideas and in crypto and blockchain, it’s amazing, but, but it imaginally works. Okay. one thing that I want to talk about is more the intersection between your content and, and the company. and, and specifically as you spend your time, how do you think about, like, do you think about them as separate things and I’m, I’m askingRobert: [00:41:20]Never did before, you know, we’re a little different now we bought on it, brought on an investment partner last year. And so like, I have to think about that a little differently versus like, Hey, it’s all my world. And I do do what I want to. so, yeah, I, I do think about that.Like, for example, look, I just came out with this book. It’s a bestseller. It’s not about our business on how to thrive in a virtual workplace. you know, we’re in a talent war right now. We’ve been doing virtual workforce as I’m sure you are in every other business in digital. We’ve been doing digital work for 10 years and now that remote work for 10 years, I think everyone’s remote, like a big part of our positioning.We know how to do this. We’ve been doing this, you know, forever. and so, you know, I just drafted an article this morning, you know, the four questions to ask, you know, a potential employer about remote work. And, and so the premise is like, it’s not all the same. Right? So that, so that’s a helpful. Piece for the book.It’s a helpful piece for our company and a value proposition. I always said to people, we, we do this a lot internally for our company writing. If you’re asked something four or five times, write an article about it, right. Even better publish that on Forbes so that when a candidate comes to us and says, how are you different, you know, from a remote, then you say, well, here’s the Inc article about the four questions you should ask, all companies.And I’ve given this tip to a lot of companies, my financial advisor, I’m like, look, you get asked it four times, you, right. Article, you have it published somewhere. And people are like, oh, like this person. Yeah, that’s what they’re talking about. Like, it doesn’t sound like you’re making it up on the, on the spot.And then all those things are our thoughts. So I do, I keep different lists where I’m like, this is kind of a Friday Forward article. So this is a industry head on, you know, why partner the marketing is going to be the next wave of digital marketing. And then there’s this stuff that’s in between around like it has some company value, it has some value outside.And I think that’s sort of like, you know, in PR we’re not paying for it. So that’s sort of like the PR that we don’t know what the value is, but we’re also not paying for it. So we’ll try to measure it as best we can.Nathan: [00:43:30]Yeah. I love that approach of having like for getting clients or in this case. The thing that we’re all trying to do is, is get cus or not customers get team members, right. recruiting is the biggest thing that we’re doing and you’re right.Like we used to have this huge advantage of being. You know, I don’t know what the stats were, but certainly not even one in 10 companies being remote, remote friendly, and now it’s like, oh, it’s a hundred percent, so, right.So you’re not thatRobert: [00:43:56]But, but you and I both know that they’re all just selling people. Oh, you can come work remote, but like, it’s very different for a whole company that’s built around that versus this whole teams in LA you’re in rural Pennsylvania. You’re gonna be zooming, you know, when they, when they pitch on this, I think this is like the difference in college and like difference between rushing a fraternity or sorority, and then pledging what, you know, it’s like, they’re selling you on a vision.I’m not sure that visions get turned out to be true in a lot of companies, but it’s going to take awhile for people to figure that out. So yeah, we want, it’s good for us that people to read that, ask those questions, know how we would answer them. I think you should always be publishing that sort of content around your, that, that strengthens your employee value proposition. Aall that stuff,Nathan: [00:44:38]Yeah. I love that of specifically putting it, like placing the content somewhere else. Like we have that content on our site. it’s soRobert: [00:44:46]Right.Nathan: [00:44:46]To link out to it and be like, well, I mean, you didn’t have to say like, here’s the article that I wrote for ANC. You know, you can say like,Robert: [00:44:52]Right. called me and I said, here’s some really good content for your weekly Inc column. Like, do you want to write an article about this? And I’d be like, yeah, that’s a perfect day. Right? I mean, this is, this is how the world works. And then you point to the coverage. I mean, this is, this is, this is how the world works.Nathan: [00:45:06]Yes. All the, all the strings behind the scenes.Robert: [00:45:09]Yeah. So I’ll expect to request from you nextNathan: [00:45:11]Yeah. I’ll have to think about what that is specifically, but, but yeah. We’ll make it happen. let’s see, what else did I want to ask you about? Oh, let’s talk about company culture. That’s something I’m trying to think of. If and I had met before we did a panelRobert: [00:45:25]I think we met like, literally on that panel, likeNathan: [00:45:28]Yeah.Robert: [00:45:29]That’s how we met.Yeah,Nathan: [00:45:31]Yeah, it’s a topic that we’re both super passionate about you at one point, I don’t know if this is still true, like things are in flux. You were the number one rated CEO on Glassdoor for aRobert: [00:45:43]I think I was, I was, Number two, for one year.Nathan: [00:45:47]To number one. That’s disappointingRobert: [00:45:48]No, no. We got to number one and it’s very hard to stay up there. my experience, and I think I was given this experience to share to, someone who’s in one of my farms last night, whose company is about a hundred people winning all these cultural awards.And I said, just be ready. Like, you’re about to hit. I can tell you, like, when you went all these things and whatever, you, you hit this point where then the people who are upset in any way, like, you know, make it their mission to to be heard. what,Nathan: [00:46:17]Oh,Robert: [00:46:17]Yeah.Nathan: [00:46:17]The, now you’re at like, you have this,Robert: [00:46:19]You’re you, now that you have all these things, you are going to be a target and it’s going to frustrate you.And you’re going to now start getting the negative reviews on Glassdoor and stuff, because you’ve put yourself on a really high pedestal and somehow someone’s going to be unhappy or whatever, and they are going to want to make sure that the world knows that you are not perfect. which no one really is, but I was giving him the speech last night because he’s, the company is great and they have an amazing culture and the winning, all these words, I’m like it’s coming.I, I, you know, we look a similar approach. Like I don’t, I don’t think. That we are the best place to work in the world for everyone. I think that a great culture is when, what you do, what you say and what you think say and do are in alignment. And, and every company has a unique value proposition. I say, it’s like universities, right?The university of, I don’t say Michigan, like 50,000 person campus, very different than a small liberal arts school in may and a 500 person in the class. They could both be great schools, but they are appealing to totally different demographics. They’re clear about their value propositions and they go with that.And I think the best thing a company can do is, you know, say what it does, but I don’t think any company’s great for, for anyone. You know, our, our job is to figure out the, we found it’s about less than 2% of the people that are really good match for, you know, our culture and how we work and our industry, our, our environment.Nathan: [00:47:42]How do you, like, what are some of the things that you use specifically Acceleration Partners to, to, filter for that or did to put out there? Like these are the types of people that should apply and that would find it a good fit.Robert: [00:47:52]I know there’s a lot of controversy around kind of this cultural fit thing, particularly around a lot of DNI initiatives. To me, this is like a vernacular thing. W no companies should be looking for carbon copies like of everyone. And I understand if that’s like the fit, but I, I believe, and as I think you do a cultural fit, I think this is true with your spouse, with your community, with your company, which is like on these big principles, like we’re pretty aligned.It doesn’t mean we’re the same. We have the same hobbies. We have the same way of thinking. But like, you have, like, as I, as I said, like, if you start a church group on Sunday mornings, you don’t want a rabid atheist in that group. That’s not why you’re there to do that. Like arguing with you about everything.Like there can be a group for that person and that’s fine. But for that purpose, like that’s not, that’s not the point of it. Yeah. And I think like if your company has some core things that believes in, like, it’s not looking for a homogeneous group of people, but like you have to be aligned around those things.And each company is, should really be different and it should be. Value proposition. Like we, we look we’re, we’re a virtual company. We’re, we’re a marketing agency. We deal with really fast client services. Like that’s not for everyone. if you like consensus, decision-making where you have a lot of time to do that.Like we’re not the right environment for you. Clients want action. They want fast. So we, we, we interview for cultural fit. And again, I’ll use the word, even though I know it’s a trigger point for some people, cultural alignment, I will say not, not, not. And, and then aptitude to do the job. So the cultural part, we have a whole bank of behavioral based interview questions around our core values, and then examples of what a good answer sounds like or a bad answer.So I’ll give you one, I always say, look, if people are interviewing and they do the research to find all these questions, and that’s the kind of person we want to hire, but Excel and improve is one of our core values. We are, we, we, we, we move quickly voracious learners. Like we need people that like that.So if I said, Nathan, what’s a, what’s a book you read, or of course you’ve taken or something you’ve done to get better in the last couple of years. And you come up with crickets, like you’re you can’t come up with anything that you tried to do to get better in the last couple of years. Like probably not a, not a, great fit for our environment.Nathan: [00:50:11]Yeah. And I think in that. I mean, you talk about culture, fit people, say culture, contribution, any of those things it’s important to talk about or or make it clear that we’re talking about values. We’re not talkingRobert: [00:50:24]Yes,Nathan: [00:50:25]Like backgrounds, like, let me go find someone who went to theRobert: [00:50:29]No.Nathan: [00:50:30]I did or anything like that.We’re talking about someone who says, like it’s trying to achieve the sameRobert: [00:50:33]Right.Nathan: [00:50:34]And,Robert: [00:50:35]You agree on the same again, if you’re a partner with someone and you don’t have this share overlapping the same values, there’s no way that relationship will work out because it means when you get to the big things, you’re, you’re not you’re in discord, over those things. So, so get our value of own it.There are just some people. Again, I can see it early on and they’re like, look, this thing got screwed up. Here’s what I could have done better. Here’s I’m going to share the learnings of that. Right. And then other people who want to duck and hide, and, and if, if you’re at this company and you’re someone who doesn’t have that mentality of just owning it, like it, it it’s really going to clash with the thing, but right.That is not a personality trait. It is not a, it is not an, it is not a gender. It is not a race. It is sort of, a belief set, about the type of organization that you want to be in.Nathan: [00:51:30]Are there anything that you’re specifically looking to be challenged on or as you hire people? Right. We talked about culture contribution,Robert: [00:51:38]Yeah.Nathan: [00:51:38]In that side.Maybe you’re seeing things in the, in the values that aren’t being represented as well as you’d like in the current team where you’re actually seeking out people to, to, either challenge value, maybe not challenge the value, but challenge the team and the execution or the value.Robert: [00:51:55]Yeah, so, so right now we’ve been open with a company about this. We’re super open about feedback. We have these discussions openly. I think for some people that haven’t been in environment anymore, it’s like a little getting used to, but so we have this value of Excel and improve, which is like excellence is doing things really well, but you always have to be improving them.We’ve been over indexing on excellence and not improvement. I think people have been a little too process oriented and they had just not had, we’re not taking the smart and the calculated risks. So, we talked this through with a company and we’re like, Like co like making a mistake, not following a compliance process, making a mistake for getting to do it.That’s not good trying something new that doesn’t work, but knowing that it wasn’t going to put you out of business or whatever, that is good. That’s what we need. That’s enough. Like failing to perform a compliance check is, is just a failure to follow a process. But we did have an open discussion that like, it feels like process is winning out over innovation, and we need to really get on the improvement side.And I think what you’ll find is that when you’re implicitly or explicitly rewarding as an organization is what’s getting attention. And I think we were celebrating two minutes too much that people that were doing things well and not the people that were taking smart risks.Nathan: [00:53:10]Yeah, that makes sense. I’m reading, which I probably should have read a long time ago, but the book Turn the Ship Around, and he’s talking about, you know, so it’s a submarine captain, who went through a lot of this and, and they had it, you know, obviously every single process, like down you, but it was all about not making mistakes, like under no circumstances, will you make a mistake?Robert: [00:53:33]On a nuclear sub that maybe is really important,Nathan: [00:53:36]Yeah. but he got of like, there, they got so focused on that, that they like kind of lost critical thinkingRobert: [00:53:43]Yeah.Nathan: [00:53:43]That they weren’t like the differentiation that you’re trying to make of the type of mistake. Right. Like messing up the nuclear reactor. That’s a, like the complianceRobert: [00:53:54]Well, there’s a commission and a mission, like the whole VW diesel scandal happened because the CEO was so intolerant of mistakes. When then they found out that the engine didn’t deliver the promise emissions and EPG that he had promised for two years, they were like, we got to cover this up because he’s going to fire us all.So, they used all of their German engineering, like with battery to figure out how to cheat the whole system rather than solve the problem. so it was a classic example. Yeah. You want, yeah. A mistake, like trying something new, understanding the consequences if it doesn’t work. And that is not a mistake, that’s aNathan: [00:54:36]right?Robert: [00:54:36]Right If every night at 12 o’clock, you’re supposed to check the boiler temperature and you fall asleep and forget it. Like that’s a mistake. Like that’s a mistake you need to fix.Nathan: [00:54:46]Yeah. Yeah. Are there some, as you adopt that, like, can you model that for the team? Are there areas that you’re pushing yourself or, like challenging to make those kinds healthy mistakes or take the risks that, you know, show the learning and growth?Robert: [00:55:05]Yeah, I think it’s less of, I think it’s coaching it and modeling it. We’ve actually like again, tried to coach our team. Like, here’s how you can think about this. Here’s how you should think about like, what’s a mistake that you have permission to make. One of the things that was really helpful shared with the team when someone shared this picture of a boat.So, with a water line and like, look the below the water line stuff is going to sink the boat. Right. We kind of really don’t want to make those mistakes. And in client services, I think it’s hard because mistakes are publicly facing. So I think it’s actually even harder to like put someone on their first call and have them say the wrong thing, because then you got some cleanup to do, but to, to get photos, like, look this stuff, that’s above the water. That’s not going to stink the ship. Like let’s make them learn from them, not make them again. What we really need you to do is like watch the water line basically.Nathan: [00:55:54]Yeah, that makes sense. Okay. Last thing that I’m curious about is your shift going from here, right? You brought on a partner like investment the business. It sounds like you’re freeing up even more of your time to do content and, and like be an individual creator in that way. Like where do you go from here? What are the next things that you’re, you’re putting time into?Robert: [00:56:15]Yeah. So, you know, I have a, a long time, number two, who’s really assumed most of the operational control over the business. Last couple of years, we’ve always operated that way. I actually think, you know, that we operate on the traction kind of U S model that like, a well-run fast growing business needs someone who, you know, it comes up with 10 crazy idea. These needs the visionary role, and it needs the integrator role, the person who keeps the train on the track and then the person who figures out where, where they’re going to go lay new track. and that’s our always been our role. And as it gets bigger, you know, mean I was like, look, what I don’t want to do.My greatest value is not in. Managing people like I I’m good at training teaching, leading, that sort of stuff, but I don’t, I don’t want to be in checking calls all day and, and, and sort of going through, there are people that are much better at that than me and they actually, they like that. So I, I think we continue to sort of formalize that split, where I’m working on our, like M and a strategy right now, and our new growth initiatives.I’m continuing to do all of our leadership, training, our culture, rolling out our new vision. just being honest about what do I like to do? What do I have to do? And then what are the parts of the job that Matt’s just better at, more qualified for? And that is always third lens. I think entrepreneurs screw up, and this is different in each part of the business, but what does the business deep?Right? What does it need it from him and from me at 5 million or 10 million or 30 million, because if I’m $40 million business and I don’t want to do any of the jobs that a CEO of a $40 million business needs to do, then I really shouldn’t let my ego put me as the CEO. I should. Create the role that I actually am.Nathan: [00:57:53]Yeah, that, that, makes a lot of sense. And you see people make the shift to, you know, chairman of the board or something else where they’re still heavily involved or, or, and can still have a title or, or whatever else, but they’re actually optimizing for the business needs rather than their own ego.Robert: [00:58:07]Yeah. The business needs and what they like to do. I think, again, they’re stepping their ego out of the way earlier stage. You see a lot of people who really started in sales and they’re the CEO, but really they’re the chief sales officer kind of wrapped in a CEO package. I, I. I always felt strong. I didn’t take the CEO title too.We were like 200 people and, no, sorry, like a hundred people, other countries. I just had GM. because I, I look, I think you can be a president. You see a lot of people have a $1 million business or a founder, CEO and president, like that is just a bad ego trip. But, but, but the president is sort of the person who runs everything that the CEO or the chief executive officer that would imply that you have an executive team.Right. So if you’re a CEO of a business where you are the head of sales, the head of marketing, whatever, like, I don’t mean like you’re the CEO of your own then, at some point. So I, I, I just don’t think that’s the right title. I think that you can be president, but I think a chief executive officer is actually has an executive team that they’re leading and managing. That’s just my definition of it.Nathan: [00:59:10]Yeah. That makes sense. Well, I’m excited to see you, the rest of the content that you continue to produce and, and like what this next chapter looks. for everyone who wants to subscribe and follow along, where where should they go?Robert: [00:59:21]Yeah, book, podcasts, newsletter signup is all now one place: RobertGlazer.com.I got that all integrated over the last couple years.Nathan: [00:59:34]Nice. Sounds good. Well, thanks for coming on the show.Robert: [00:59:36]Thanks, Nathan.

Ryan Sneddon is a self-described CEO and emperor of local news. Ryan is building a hyperlocal newsletter empire one city at a time, starting with Annapolis, MD.Ryan’s newsletter, Naptown Scoop, is an email to the residents of Annapolis containing all pertinent news and events. It's an awesome community of residents and business owners coming together to be good neighbors.Ryan has worked as an editor at The Daily Thread, as a business solutions consultant at Softdocs, and as an engineer for Grand Banks Yachts. Ryan has also worked as a project engineer at The Whiting-Turner Contracting Company.Ryan studied mechanical engineering at the University of South Carolina, and also worked as a cinematographer and photographer. Ryan has done volunteer work building relationships with high school students while leading a team of other volunteers at Young Life.In this episode, you’ll learn: How Ryan stays motivated when work gets overwhelming Ryan’s philosophy and tips for interacting with your audience  A great way to assess your growth and progress as a writer Ryan’s proven strategies for maximizing your social media engagement Links & Resources From Boise AppSumo Viral Loops on AppSumo Jason Calacanis Annapolis Rotaract Club Ryan Sneddon’s Links Ryan’s Twitter: @sneddymobbin Naptown Scoop Episode TranscriptRyan: [00:00:00]First advice would just be to “get started.” Second advice would be, “don’t quit,” every day. Third advice (this is not specific to a local newsletter. I would say this to any newsletter, any brand, anyone ever) just be responsive.The great thing about an email newsletter is that people can answer it: I can reply to an email cause it’s just a regular email. Answer every single one of those, because that’s how you build up a loyalty.Nathan: [00:00:30]In this episode I talk to Ryan Sneddon who runs Naptown Scoop, which is a local newsletter for the Annapolis region. I like it because I started a local newsletter called Boise, to just about a thousand subscribers. And, you know, Ryan and I were chatting back and forth on Twitter, just saying like, what ideas are we learning from each other?He was giving me some advice and I was like, you know, I why don’t you just come on the podcast and share the story, share what you’re doing.It’s pretty fun how it’s coming together. He’s working super, super hard on it, and we dive into all the details. So with that, I’ll get out of the way.Ryan, thanks for joining me.Ryan: [00:01:09]My pleasure.Nathan: [00:01:10]So give us the 30-second pitch. What’s the newsletter, and then from there, we’ll dive into, “Why start a local newsletter?”Ryan: [00:01:18]My newsletter is called an Naptown scoop and the 30-second pitch; I could really do it in 10 seconds. It’s just everything you need to know about the town delivered straight to your inbox three times a week. And I would do it more if it were a bigger city, do it less if it were a smaller city, but that’s just kind of the perfect number of times that gets you all the information, but it’s not too much.Nathan: [00:01:40]Yeah, that sounds good. So what was the inspiration to start it?Ryan: [00:01:43]There’s another company. I mean, there’s a couple of companies now that are out there doing this, but I lived in Columbia, South Carolina after college. I went to college there and stayed a little bit extra. And there was a company there that did it and I really liked it. And then I moved away back here to home, and I didn’t have that.And I was like, well, that was cool. I can’t be the only one that liked that. So I was like, I’ll just build it here. And, I wasn’t the only one that liked it. We were talking before we started recording. There’s not really a good original ideas in my head. So the fact that I wanted it was a good sign, because if I wanted it other people probably do, too.Nathan: [00:02:17]Yeah, that makes sense. I am fascinated by local newsletters. I started one on my own called From Boise.Ryan: [00:02:27]I get it; you got to see what everyone else is doing and your same space.Nathan: [00:02:31]Got to get some ideas. I saw Andrew Wilkinson do it in Victoria, British Columbia, which is one of my favorite cities to visit. And so I saw him do that and I was like, oh, well I love Boise as much as he loves Victoria, and wanted to do some local projects. So, so, it’s been fun, but maybe before we dive into the growth and all of that, what are some of the favorite moments from running it where you’re like, “Oh, this is actually pretty sweet?”Ryan: [00:02:59]There’s a lot. One just happened last week. I think it was, it’s been like a really long, last two weeks; has been a really super full and, I don’t use the “B” word. I don’t say “busy.” I’m not allowed to, but it’s been like a really full on hundred miles an hour, 20 hours a day, kind of lasts two weeks now.Like sometimes—no joke—sometimes more than that. But last Thursday night I was delivering cookies to people who bought shirts, because I made some shirts to sell for the brand. And I said I was going to deliver cookies to the first or 10 out of the first hundred orders, which was like super ambitious of me.I didn’t even think about the fact that like, I would have to sell a hundred shirts for that to happen. and I only sold 10 shirts. So I delivered the 10 cookies to the first 10 people instead of 10 out of the first hundred. But I’m delivering cookies to this one, and I just emailed everybody and said, if you’re not home, can I leave it in the mailbox?And they were like, yeah, our mailbox is a giant stone pillar at the front of the driveway. And I was like, giant stone pillar? Like, this is probably a pretty nice house. And so I put in the GPS and I’m like, oh yeah, this is a waterfront looking pretty good. I roll up to the house and it’s gorgeous.It’s probably like this three to $4 million house. I can look at it and kind of think I know who the architect is, because she’s pretty famous around the area. And as I’m putting these cookies in the giant mailbox, they roll up and they like the car honks, and they roll down the window. It was an Uber, they rolled out of the back windows and they’re like, “You must be Ryan!”And I was like, “Yeah!” And they were like, “Do you have time to come in for a drink?” And I’m like, “Yeah, why not?” it’s 9:45 at night. No, it wasn’t, it wasn’t a Thursday. I think it was a Wednesday because if it was Thursday, I would have had to go home and write the email for Friday. But since it was Wednesday, I didn’t have to get one out to the next day.So I was like, “Yeah, I have time for a drink!” And I ended up sitting on their back porch for two hours, drinking wine, just talking about their life, my life, the business, the guy, it was just the guy’s first day of retirement. He had just retired from being CEO of a giant PR firm in New York city. And this is their retirement house.It turns out it was designed by my favorite architect and it was just an incredible experience. I saw them the next day, too, because they live on this Creek called Mill Creek. And have you ever seen hydrofoils?Nathan: [00:05:24]Yes.Ryan: [00:05:25]So we were doing that the couple of days before. but we were doing electric ones, so they have a little propeller on them.They’re super fun. And a bunch of like, it’s really trendy right now. And there’s like three businesses that all started in Annapolis doing it. And, two out of, three of them have invited me out multiple times to go out with them. And so I’ll do it and put it on Instagram. And part of it is like, I do want to help these people cause they’re just super starting out.They’re like way earlier than even me. And also it makes me look super cool when I go out and do this thing. Every time I post this, it gets incredible engagement and people love it. And then, you know, this is a funny story about that. This guy, his name’s Rob and his wife, Tammy. They were like, we saw your friend James yesterday.And James is one of the people that owns these new businesses. We saw them out doing the foil and we asked them, we called them over to our boat and we said, are you Ryan? And he was like, apparently a super disappointed that he was like, no, I taught Ryan how to do this. Like, I’m the only reason you know him to do this.And they were like, yeah, we, he could tell that we were kind of disappointed that he wasn’t you, but now we met you. so it was just crazy. And we were out doing it the next day and they were on their docks at high. so just stuff like that, that like I never, in a million years would have written that as a story, but it happens and it’s just, it’s a great.Nathan: [00:06:42]Yeah. You, you had a tweet the other day about going out for a walk with the mayor, which on one hand that’s, that’s a pretty cool thing. You know, you’re like, oh, I get to meet. You know, meet the mayor and all of that, but then more people recognized you then the mayor just as you’re walking around town.Ryan: [00:06:58]Yeah, well, the mayor, so it is cool to go out with the bear, a campaigning event for one of our city council people or city council hopefuls. And, I went out just to meet her. I, no one else showed up except for me, her and him. And her, I think her campaign manager or somebody who works for her. And so instead of doing their normal walk where she walks around the Naval academy, football stadium and talks to her constituents or hopeful constituents, we went and saw the new bike path that the it’s one of the mayor’s projects and he just kind of hijack the campaign walk.And he still thinks that the Naptown Scoop is an ice cream. it’s kind of hilarious. I’ve I’ve met the guy a bunch of times, someday. Well, we’ll get them to know that it’s not actually an ice cream shop, but yeah, we’re, we’re out walking and he’s introducing himself and he’s got this British, not British, Australian accent and he’s campaigning for reelection.They all, there are like city council persons. She’s not on there yet, but she’s hoping to be on there. So she’s campaigning and he’s out. He introduces himself as, Hey folks like, Aw man, Buckley. This is I’m running for reelection. We’re resurfaced in this bike path, and this is karma. She’s going to be a great asset to this world when she gets elected.And then he gets down the line, I’d introduce me. And like, doesn’t know who I am. Doesn’t know how to introduce me. And these two people are like, oh, we know you. And it was just the funniest thing is like, yeah, you have to introduce you yourself. They’d actually didn’t know you were the mayor. They have no idea who this person is, but yeah, they know this 24 year old kid you’re hanging out with.Nathan: [00:08:24]Nice. Yeah. That’s what you get when you build an audience, you know, it works out. Yeah.Ryan: [00:08:30]And that’s the power of the internet that you can get to that level of recognition in 10 months, or? Well, he’s been the mayor for like four years already. but like he, I mean, he’s doing important mayor stuff. He’s not on social media building up at all.Nathan: [00:08:45]So let’s talk about the last 10 months. So, when, when exactly did you start it and what, like, I’m curious what the path was to the first a hundred subscribers or 260.Ryan: [00:08:55]First send was August 17th, 2020 that sent the, I started running Facebook ads like a week before I sent it. I, I made, I shortened the story a lot on the way in, I didn’t just like decide I was going to do it here. I was trying to hire people out elsewhere to do other cities, but I didn’t. I didn’t know how to hire anybody and I didn’t really have enough money to pay him. So I got a cup of kind of close with a couple of people. And then finally, like the last one we were about to start, we’re going to probably start writing like the next week. And he’s just like pulled out at the last second.He was like, Hey, this is, I’m not going to do this. And so that was just fed up and I was like, I’m going to start that here. So from the time. Told me on the phone that to the time the website was actually up was probably like eight hours. And then the Facebook ads were running a couple hours later. So they would run it for a whole week before I sent the first email, I think I sent the first email to 64 people and I sent the second one to like 120.So the path to a hundred subscribers was not like, you know, super long or grueling or really even tough. It was just like, oh, I’ll put up some Facebook ads.Nathan: [00:09:58]Yep.Ryan: [00:09:59]Everyone talks about how the first 100 is super hard and I’m like, No, I just had to pay for him.And I think set of that for 64, I’ve gone back and looked at this. Almost all of them are still on board. And this is a stupid, crazy fact, seven, at least when I last check this, which was like a month ago, seven out of those first 64 had opened every single email since which just blew my mind.Nathan: [00:10:27]Yeah. so first I’m here is like, when you’re paying for the Facebook ads, what was the cost per subscriber? Like how much did it, did it cost to get this off the ground?Ryan: [00:10:35]In the early days. I think those people were coming for like 50 cents, 80 cents each. I was like, this is great. Yeah. So that was great. it’s it’s more like,Nathan: [00:10:47]$3 a subscriber, I would have been like, okay, that, that makes.Ryan: [00:10:51]No, it’s more like, I try and keep it as close to a dollar as possible now. but usually ends up creeping up to around $2. And once it start getting up to like 2 20, 2 50, I know it’s kind of time to make a new ad and that one’s kind of spent, or just like put it on the back burner for a little while because people, they just get sick of it.And this is a small town, so the same people are seeing it all the time. So really I’m just kind of trying to convince the same people over and over again with different creators. So I still, I keep it under two 50. I, I kinda need to, but I, I would love I, when I’m down in the ones, I love it.Nathan: [00:11:24]Yeah, that makes sense. What’s the population.Ryan: [00:11:27]36,000 in the actual city.And then I cover a 10 mile radius outside of that, which opens it up to, I think 200 to 250,000 total, maybe probably close to 200. It depends on which population might be look at. It’s not a super well-defined area, but yeah, 36,000 in the city, probably around 200,000 in the next 10 miles.Nathan: [00:11:48]Okay. Yeah. So the city itself, yeah, that’s relatively small, butRyan: [00:11:53]Yes. Very small.Nathan: [00:11:54]Yeah.Nice. so growing from there, what, like what worked, has it been almost entirely Facebook ads or what, what are the things you.Ryan: [00:12:02]A lot of Facebook ads, I think probably half the audience has come from that. people are starting to discover it organically, like put some effort into ranking for certain things on Google. So people are discovering it. I think that so a decent amount of people are Googling it directly and I’m imagining the only way they’re doing that is if they’re free.Telling them about it or if they saw it somewhere. so I still count that as organic cause obviously that’s free. If you Google Naptown Scoop, it’s like, all you get is there’s nothing else that comes up, which is great. and I have a referral program as well. That’s accounted for. Almost 20% of the subscribers.So that’s a pretty decent chunk as well. And the way that’s set up, that’s mostly free. I got a lifetime license of viral loops from AppSumo super lucky on that. the first reward is free. It’s a birthday shout out at the top of the email and it works well because it’s a local place. Like you couldn’t do that on a national newsletter, but your friends might see that and you might want your friends to see that.So that’s a fun reward. And then at the second level, I have to pay for a mug and the next little I had to pay for a bag. But not many people get to those levels. So like a referral programs or as long if when the first rewards free referral programs can be absolutely awesome.Nathan: [00:13:12]Right? Yeah. That makes sense.Ryan: [00:13:14]And then also I do a lot of work on Instagram, so I’m a pretty big Instagram following.I’m sure some of that has come from the newsletter, but also it feeds the newsletter or people are discovering it through there. I made this kind of cool and like basically made my own link tree or Lincoln bio kind of thing where it’s just posted on my website. Apparently Instagram doesn’t like those, third party apps.So I’m like, well, they’re not going to punish me for linking to my own website and I can just make my own one of those easily. So I’ll do that. And I don’t have to pay for that.Nathan: [00:13:42]Yeah. Yeah. That makes sense. so like, let’s go through some of the numbers. W how many subscribers do you have now? What’s the Instagram following?Ryan: [00:13:52]Subscribers are 5,500. 70 I think is the last I looked today. it’s still, still not big enough where I can, like, I can spout off the exact number. someday we will, hopefully we’ll just say like, oh, like 15,000, I don’t know, you know, give or take a thousand who cares. but now right now everyone’s still matters and I would like everyone to matter forever. but Instagram, I think Instagram is like 4,700 something around there. So, yeah, people always look at the Instagram and they’re like, wow, it’s so big. And I’m like, but the email’s bigger and more powerful.Nathan: [00:14:26]Yeah. Yeah.What are some of the differences that you’ve seen when you promote something on Instagram versus promoting it in the email? Because I always say that, you know, the email is so much more powerful, but it’s fun to have specific examples.Ryan: [00:14:38]Well, it depends what it is. So like just. It depends on what platform you’re promoting. So with the newsletter, we had this really cool fundraiser a couple of weeks ago called rock the dock. You’ll hear a lot of waterfront stuff. Cause everything Annapolis is a waterfront town and it’s like very much focused on that.So rocket dock was a fundraiser by the broad racked, which is like the young person’s rotary and they put their tickets out on sale. And I think that sold a decent chunk of them, but I put it in the newsletter and it sold out in like hours. So that was powerful, probably sold like 50 or 60 tickets through that.And it sold out in like four hours and then they reloaded it cause COVID restrictions loosened. And I was like, okay, I’m going to sell it out again. And I don’t know that I sold it out again. Like the results were not as directly. they just weren’t, they didn’t seem that correlated. Like last time it was pretty clear.It was like, No 6:00 AM on Friday morning, it wasn’t sold out. And then noon. It was, and it was like, well, you didn’t do anything else today to really push it hard. it did eventually sell out the second time as well, but I don’t know if it was directly attributable, but that event is another one of my favorite times that we can talk about later.And, a lot of it wasn’t true. But so that’s when I say like the email can be really powerful if I’d put them on Instagram and just hard to convert, like I can convert you straight from the newsletter to the ticket link for the, for that event. That’s a really powerful thing. On Instagram. I can’t do that as well.I don’t have 10,000 followers, so I can’t like do the swipe up stories and store links. Don’t work in posts anyway. Like pretty sure Instagram will penalize you on the algorithm if you do use that. Cause all the posts I see with links are always at the bottom of my feed. but like. There’s a business that I’m visiting or like, and support, or like a new business opens.Then I see the power of the Instagram where it’s like, well, this new business opened up. Here’s like an I’ll post something about them and say, go follow this business. And you know, like one day they have a hundred followers and the next day they have 300 and it’s just a nice head start for them. So I see them be powerful in different ways.I think it’s much more practical the way the newsletters.Nathan: [00:16:48]Yeah. Yeah. I like that. when you do on the revenue side, like obviously growing an email list is, is a great thing that being involved in the community, all of that’s really fun, but, ultimately this is a business and you’re spending quite a bit to grow it. And so I’m curious, what’s worked for monetization.Ryan: [00:17:05]Yeah, spending quite a bit to grow it. advertising in the newsletter is the primary source. It’s kind of the way that I look at it now. And I don’t want to say easy, but it’s just like, if you’re building an audience, why not? Why not do that? I don’t see this as a product people would pay for, it’s not original reporting.It’s not, you know, investigative journalism. I’m just seeing what’s happening everywhere else and then summarizing it. So I feel like people would have a hard time paying for that. I don’t want to do donations. cause that doesn’t strike me as like a smart business and look for the brand. And that’s.So really it will be primarily advertising supported. I have thoughts of how to do a premium subscription, where maybe you get some more content. Maybe you have some deals with local businesses, but that’s kind of down the line. We’ll see if that happens. That would be great. Cause that could make my subscribers much more valuable than they were an advertising.And then also there’s secondary small stuff like selling these shirts and I would like to do some events. So those things aren’t going to make a ton of money. They’re not nothing.Nathan: [00:18:13]Yeah.Ryan: [00:18:14]So that’s.Nathan: [00:18:15]How has it been selling advertising? Like, is it easy to get sponsors lined up and businesses or is that, you know, quite a bit.Ryan: [00:18:23]That’s a lot of work and that’s actually the first thing I brought someone on to do. cause I don’t like doing it and I’m not good at it. And there are things that I am good at. Maybe even great at that only I can do. But that’s not one of them. So I brought someone on to do it. just recently she is about to close her first deal, hopefully today or in the next couple of days.So that’s exciting. I would definitely, I had to like definitely kind of discount and let her have some freedom on it, but I was like, I feel like it’s just more, like, it’s better for her to just get that first deal and have some confidence then like say, no, you actually can’t give them a discount, but like make sure they know it’s a one-time thing.Yeah. No, I want you to be confident going out and doing this again. So that is hard. I’ve had like pretty full out advertising for the last few weeks. It’s this kind of, it was like nothing, nothing, nothing. And then kind of all at once. so it’s been pretty full, but it is still just a small audience.I mean, I I’m charging on opens and only 2,500 people are opening each one. So it’s tough to charge. You just can’t charge a lot on that.Nathan: [00:19:30]Yeah.Ryan: [00:19:31]That’s just the stage we’re in right now.Nathan: [00:19:33]Yeah. Those early days are interesting. what are you charging, you know, for each sponsorship or, or each open?Ryan: [00:19:41]I like to keep it around. I like to think this is a high CPM also, as I’m working on something now for another local client, like as it just kind of a side hustle thing, I’m seeing what other people are charging and I’m like, wow. I could be charging a lot more. so I, I used to feel bad saying this, but now I don’t at all.I charge $70 CPM for a, a primary ad, which has a picture and a lot of texts and it gets your logo at the top of the email. And then I charge $35 CPM for our, I call them the secondary ads. They’re just little text ads that have 50 to 60 words, and they’re a little bit further down to the bottom of the year.But like I’m, I’m seeing other people who are charging $200 CPM for an email blast. And I’m like, this is not good. Like, cause I’m, so I’m working on, promoting a music festival right now and we need to sell a lot of tickets. So I’m like, well, we gotta pull all the levers. So I sponsored this newsletter blast.It was basically $200 CPM to reach just over 4,000 people. And I look at my, you know, right now, I believe that we have gotten two ticket orders out of it so that, that’s not good.Nathan: [00:20:57]We’ll have to wait and see how that return on ad spend comes in,Ryan: [00:21:01]Yeah. If, if this, if this is directly attributable to it and the one earlier this morning, was it because one of them was a VIP order for the music festival. So if those are both from it, it looks like we make the money back, but like nobody wants to like a one X return on ad spend,Nathan: [00:21:16]Right. Yeah. That makes sense. It’s interesting. If people can charge kind of. Almost whatever on ad spend, you’ll see people just make up something and it’s like, look, if the market’s there and people are buying it then great. And if not, then obviously you need to change your pricing, change your offering, something like that.Ryan: [00:21:35]Yeah, it’s this like black magic that nobody really knows how to do. Like there’s no real formula. You’ll like Google it and you’ll see numbers and stuff, but like everybody’s charging different things. And it’s, I feel like the advertisers that I’m working with are a lot less sophisticated than I thought they would be.Like when I advertise something I’m like, all right. Like I look at that blast and I’m like, I’m paying. $200 per thousand people. I’m going to reach, I’m going to reach 4,500 people or 4,000 people. Like I need to make X dollars back on that to consider it a success. And I’m like expecting all my advertisers to come in and be the same way.But I’ve actually only had very few ever who looked at it and they were like, yeah, we think the math works for us here. Most of them were just like, oh yeah, well you have 5,000 your list. And I’m like, yes, but like not all of them are going to read it. And they’re like, no, we do have 5,000 people on the list.That’s not the numbers. You need to care about 2,500 of them. We’re going to see it, not all 5,000. And they’re like, yeah, I don’t care how much it costs. And I’m like, okay, you guys. So we actually just took a provision out of the contract where I used to put it in like, Hey, this is based on this amount of impressions.And if you don’t get it, you’ll get a refund.And, I was like, nobody cares about this. So I just took it out and I was like I’m not gonna, if I. Yeah, punish myself for something that my advertisers don’t care about. If there’s happy with their ad spend and the return they get on it, even if it’s just from a brand building perspective, then who am I that say they can’t spend their money with me? Or should.Nathan: [00:23:04]Well, I think about the, some of the groups that have advertised in from Boise, you know, you get like the local chamber of commerce or like the, There’s a first Thursday, like series downtown. So it’s like a concert and, you know, vendors coming out and that kind of thing. And it’s beautiful promoting that.And they’re like, look, we’re just trying to drive awareness for it. We’re not actually like, there’s no click back to a ticket sale or something like that. So they’re just like, just promote it. And, you know, in this case, like we only have a thousand people on our, on our local newsletter, but, you just not into dollar amounts.Really register. And so they’re just like, yeah, a hundred bucks, 200 bucks, 500 bucks. I don’t know. It kind of rounds to the same number,Ryan: [00:23:50]And that’s the thing that I can understand, because I can’t afford to do that with, with my business. Now it’s like, if I’m spending. $450 on Facebook ads over these next two weeks. I need to know that I’m going to get 225 people out of that to read the emails, at least. And I don’t like I don’t have money to go in and put a banner up at our local golf tournament.Like I need to, I’m like very, very, very much performance driven on advertising right now. And so I just expect that everybody who wants to advertise me is going to be feeling the same way. Cause I think they should be okay. They’re not. And so I have to get used to selling that. And really now I don’t so much because I’ve got somebody doing it for me, but that was definitely something I did not expect.I was like, everyone else is going to be super concerned about what they’re getting out of this. And they aren’t, some of them are, but, but aNathan: [00:24:40]Yeah. Yeah. I’m curious. Is there anything offline that you’ve done or like you mentioned the golf tournament, right. As something that you’re not doing right. Like for our newsletter, I thought about, should I be putting a business cards? Should I be, you know, like, are there things in person to try and get subscribers or is like, you know, Facebook and other social ads, the best way to go.Ryan: [00:25:00]I mean, I think those are the best way to go from a. Getting a lot of people on perspective, but from the quality of subscriber perspective and from building a community perspective, the in-person stuff is absolutely the best way. And I have, I’ve got business cards right here. I just like pretty basic on the front, put on the back.They’ve got the QR code to sign up. So I hand out those basically I need somebody to go somewhere and meet people. I’m not just like handing them out, for the heck of it. Like, I’m not, I’m not like the guy on the streets. He was just like here. but if I meet somebody and they like ask what I’m doing, I’ll be like, yeah, here’s a, here’s a business card.You can sign up on the back. And those people, they. They always tend to be, or not always, but they normally tend to be very good subscribers and those are the people that tend to respond to the newsletter. And then the source time they get it and they’re like, Hey, like, I’m so glad you did. Like, I really liked this great meeting you.So that’s like the best way. I think that’s, you know, the classic story adage, like do things that don’t scale. I can’t get out there and get every person on the list. But when I do get the person on the list, cause they meet me and they liked me and they like, they get my business card. Then I think those people turn into really good subscribers.Nathan: [00:26:23]Yeah, that makes sense. What are some of the things that have been like really hard, a lot more challenging than you expected in getting this started? When you go from last August to now, you know, what was a lot harder than you expected?Ryan: [00:26:35]That’s a really good question. nothing pops out originally, like immediately, and that’s not just because nothing has been hard obviously, but. I guess I didn’t really go into this with that many expectations. Like I didn’t go into this expecting it to be super hard or super easy. I just kind of went into it, expecting to build the product that I wanted.So yeah, nothing was really like that much harder than I thought. it’s just kind of all been hard, I guess. sometimes it is pretty hard to keep going. Right. We’re not the only one doing all the things and I have to be out at all the events and then come home that night and write the email every once in a while the thoughts creep in when it’s like, Hey, you know, you could just not send this email tomorrow.Nobody would care. And you’re like, no people would care. Not maybe not that many, but like, I can’t do that. I’ve done 122 in a row now, and I’m not going to stop now. I’ve never missed one.So I think that’s probably. I have never. And this maybe it’s just because I haven’t really done a lot of super hard things in my life, but I’ve never really done anything where I was like, besides maybe even playing sports in high school and you’re at like a hard practice or something where you’re like, I want to quit this regularly.Like in college, I never thought about dropping out. Cause it was hard. I never dropped a class. I never like just stopped going to a class at my last job. I never. Just kind of quit on a project. I did quit the job to go do this, but like, that’s, that’s a little bit different, but this is something that I look at.And then like a couple of times a month, I’m like, man, this is really hard. Like just as a general thing overall, like you could quit right now and your life would get a lot easier. and then I. Very important phrase to me. I write at the top of my list every day is don’t quit every day. cause I don’t need the reminder every day, some days I’m like I’m going to do this for the rest of my life.And other days I’m like, I just want to go to bed right now. And it’s not like a, an unreasonable time to want to go to bed. It’s like 2:00 AM and I’m not done working yet. And it’s not like I’m just doing busy work. It’s like, no, I’m not done writing the, email yet. And that has to be out at 6:00 AM the next morning.Those are the times when I’m like, I really want to go to bed. I could quit this. But I don’t let myself,Nathan: [00:28:55]Yeah.I think that’s something that a lot of content creators can relate to of like you set this expectation and you’re meeting and consistently, and like, you know, whether it’s a weekly or three times a week email or anything like that. But then the, those moments come where you’re like, ah, I actually don’t like, maybe I want to have done it, but in this moment I don’t want to do it anymore.Ryan: [00:29:16]Yes. They’ve probably been less than that. I mean, honestly, probably less than five of those times. Like I’ve written 122 emails, probably only five. I’ve not wanted to send. And I have a secret for when that happens. I just put on, it was like a couple of songs that I really like, and I’ll just put them on repeat over and over again.But these headphones on and turn them up real loud and just right into it.Nathan: [00:29:38]Yeah, that’s a, that’s an important skill to be able to, you know, force yourself to power through and finish the task.Ryan: [00:29:45]Yeah. I mean, if you don’t quit every day, you’re going to get where you want to go. I guarantee it.Nathan: [00:29:50]I have create every day as like, it’s been like a slogan or a mantra for a long time, but I also like just don’t quit every day. That’s awesome.Ryan: [00:29:59]It’s kinda just like show up, but I don’t. Like saying show up every day. Doesn’t really imply. It doesn’t really like inspire me in the same way. Cause when I think about showing up, I’m like, well, you can just show up and kind of like go through the motions and like just be there.But like don’t quit every day makes it sound like you’re really pushing every single day and don’tNathan: [00:30:22]Right.Ryan: [00:30:23]That.And I promise if you don’t do that, you don’t quit every day. You’ll get what you want might take a long time, but you will get it just by the definition of the word quit. If you don’t do that.Nathan: [00:30:33]Yeah, that, I don’t know. I never thought of that before, but how show up is like, you know, put in some effort, I guess, but really that when you say don’t quit, itRyan: [00:30:44]Show up, doesn’t inspire the same confidence.Nathan: [00:30:46]Yeah. Cause it’s like, you’re really putting in effort if you’re actually thinking about quitting.Ryan: [00:30:52]I’ve never actually until really this year.Getting a tattoo of anything. But if I ever were to get a tattoo, I’d want to get don’t quit. Every day I write on my forum there, like it’s, you know, Casey Neistat and how he’s got the do more tattoos right there. I always saw that. And I was like, that’s a really cool tattoo, but I can’t just copy his, what would I put if no, I’d get don’t quit every day. I think there’s enough room.Nathan: [00:31:16]Yeah,Ryan: [00:31:18]I that’s like the only thing I’d ever thought about, maybe getting tattooed on myself. I don’t know if I’ll ever do it also because tattoos are just expensive, but also like, I feel like that’s pretty sensitive area and tattoos hurt a lot, so there’s no reason to do it. I can write at the top of my, to list every day and it’s just fine.Nathan: [00:31:31]That’ll that’ll work.Yeah. So as we’re talking about like this, this journey of a local newsletter and everything, one, we’re not overly glorifying it, which is good. Cause I’d hate for us to come in and say like, everything’s amazing. And then someone starts and they’re like Ryan and Nathan, you didn’t tell me how hard this is.So at least we’re saying how hard it is, but I’m curious. So someone’s starting from scratch, or if we want to use like my newsletters, this specific example at like one fifth, the size of yours, what’s some of the advice that you would give, maybe we’ll go first, starting from scratch. And then second, like baby traction.Ryan: [00:32:05]Starting from scratch. I’d say like, just do it. I did not know if anybody was going to care about my newsletter. I was like, I’m just going to write this. I’m going to get it out in front of people and I’m going to start writing it. Everyone, I think likes to build up the. the. process where it’s like, I have to have it all figured out before I start doing it.Now, just do it. I look back at the first newsletters that I sent and I laugh and how bad the writing is and how bad email template looked.Nathan: [00:32:32]Yeah.Ryan: [00:32:33]Everything looked. And I think if you don’t look back at your work a couple months later and laugh at it, then you’re not improving fast enough. Like you should look at it and be embarrassed because then you’d look at your current work and you’re like, this is much better than that.And then hopefully the same thing happens again in six months. So just get started. You’re not going to be perfect right away, no matter how much you prepare. and you’re just going to get behind by not starting. So first advice would just be to get started. second advice would be don’t quit every day. But then also third advice. And this is really for any, this is not specific to a local newsletter. I would say this to any newsletter, any brand anyone ever, is just be responding. That’s a great thing about an email newsletter is that people can answer it. I can reply to an email because it’s just a regular email answer.Every single one of those, even if it’s like somebody saying that they hate you and they hope that you get dropped your ice cream cone the next time reading it, respond to that and just say, Hey, thanks for taking the time to respond. Like, sorry you feel that way about the newsletter. I always respond.That is the biggest, most common. Not a compliment, but comment I get on the newsletter is like someone will respond with a clarifying question about a story I wrote and I’ll answer within a reasonable time, like a couple of hours sometimes within an hour, always within 24 hours. And they’re like, almost always the responses unless they’ve responded before.Wow. I didn’t expect you to answer. And it’s like, wow, that’s the baseline. That’s the hard to beat at all. Because most brands they don’t answer. And so if you do. It’s really not hard to set yourself apart because the expectation is that you won’t, so you don’t even really have to answer the question fully.I get. And I’m like, I’m a huge, I don’t know if I’d say perfectionist, but like, I have a very strong idea of like how I want to do things. Yeah. How I want to deliver results. So some have responded to actually a meme. I posted the other day making fun of how, like, none of the restaurants have employees right now, and they’re all hiring and this person responded to it and was like, Hey, like, do you know any restaurants that are hiring?I actually like, I’m really looking for a job. And so in my mind, I’m like, yeah, I’m going to get your list of every single restaurant in town that’s hiring. And then that’s hard, right? Like that’s a lot of work. So I.Reaching out to a couple of friends of mine who own restaurants or work for restaurants like higher level positions, like Izzy restaurant hiring, et cetera.I think I said our list of like eight restaurants that are hiring. And, there are our tourism board has a list of restaurant jobs, which is pretty cool thing they do. And I sent her this and I’m like, This is not good enough. Like if I’m grading my performance here, I’m giving this a C minus, like this is a passing grade, but just barely.And then she responded and she was like, oh my gosh. So thankful that you did this, like, I didn’t even expect you to answer. This means the world to me. And I’m like, okay. So for her, like, this was an, a plus, but for me it was a C minus. So it’s like, you don’t need the bars, the high, just answer it.Like I said, you don’t even have to fully answer it the way that you think it should be.Just answer your fans or your readers or whatever they are. And, like I said, the bar is not answering. So just by answering you’re way above it,Nathan: [00:35:49]Right.Ryan: [00:35:49]That’s probably like, most are probably my top three tips I’d give to anybody. It’s funny because none of them are really actually related to writing news.Nathan: [00:35:57]I think that’s how life as a creator goes. Like, it’s all about the other things than the actual, like the exact work that we do every day.Ryan: [00:36:05]Yeah.I mean, I definitely have like tactical tips of how you read a newsletter too. Like proofread it out loud, like reading the words out loud. That’s a great way to catch typos. but I think that’s less important than just first of all, starting second of all, not quitting and third talking to your people because that’s how you build up. Like I fully believe that if a competitor came in with more money and more people and they try to do exactly what I’m doing, and that was the difference, they didn’t do that. Sure. They might get any new readers, like anybody who has never heard of me, that they somehow reached with advertising or just reached first.They’re probably going to go to that new guy. That’s great for them. But I mentioned that very few of my people would actually jump ship and go. Because they know that when it’s eight o’clock on a Friday night, and I don’t know how you scale this up. Cause I don’t know if I can expect employees to do this same thing, but like when it’s eight o’clock on a Friday night and you messaged the Instagram account and say, why is my favorite pizza place closed?And I answer, cause I happened to see the Instagram posts from the pizza place about how they’re up and broke and then there’ll be open the next day. Like you get an answer then, but, and so you’re not going to leave that brand for someone doing the same thing. It’s not going to answer you. It’s just, I mean, it’s the best. To build up loyalty. And it’s not just fake, like by doing that, like forcing yourself to pretend to care about the people and I actually care. But if you did pretend to care and you still did that, I think you’d find it really hard. Not to actually care after a few weeks of trying that out.Nathan: [00:37:33]Yeah. I think you’re right. I’m curious more about the journey, say from a thousand subscribers to 5,000 and I can ask totally selfishly as, as a, you know, I’m casually working on the same thing. what are some of the things that worked in, in that? Was there anything different or was it just more of keep doing more of the same and just give it time?Ryan: [00:37:55]A little bit more of the same. it was, you know, refined techniques on Facebook ads and the creative use there. So like in the beginning I was just doing stock photos. Then they started to perform really poorly, even when I would make new ones. And I was like, oh, what’s going on here? And so I started get some feedback from some people in the town that were like, everybody knows that person doesn’t live here.Everybody knows that picture. Wasn’t taken. Like try something that’s a little bit more authentic. And I was like, okay. So I did now I do. And this works really well. I just walk around the downtown area and talking to my phone, selfie style and film, these little punchy, quick little ads telling people to sign up for this thing.And they knock it out of the park. Those things crush. I can get my cost of acquisition down below a dollar again. So refined techniques like that, just kind of getting better at Facebook ads. I’m getting better at Instagram. Like. What people like and what they don’t like. Like I used to post some stuff that just, it was useful information.It was like I’m posting the live music schedule from the newsletter on the Instagram. And it’s useful. That’s, that’s a lot of people’s favorite part of the newsletter, but on Instagram it just performs horribly. And so it was learning like, okay, don’t do that. Even though that’s useful, don’t put that there.And then trying other things. I didn’t do memes for awhile. And then I started doing meetings and I like started getting a ton of engagement on my Instagram. And I was like, okay, names are good. You know, I think Elon Musk said, maybe this is something just randomly attributed to him, but like he who controls the beams controls the universe and it’s just like such a good way to communicate right now.So I started doing that in the engagement shot through the roof, and then I was like, there’s this. Just other newsletter that does exactly what we’re doing called hate Kingston for Kingston, New York. And, at the beginning, they actually copied me so bad that if you would respond to their welcome email, it would email me.And we’re friends now it’s, we’re we’re friends and it’s all good. I told them like, Hey, I copied everything I’ve ever done. So like, I’m not mad about this. You just need to fix this because your people are trying to email you and they’re talking to me and, and, and they intended to talk to you, but they do these, they started doing these great local focus meetings.So it was like, Yeah, all the regular meetings that you see, but with a local twist and I started seeing them, I’m like, this is incredible. The guy’s name is Chris, who does it? I was like, I love this Chris. And he was like, well, just feel free to steal any of them. So I started like using some of their templates and then kind of making my own things.And once I started doing local means versus like just general memes, my, and I only do it on stories because I’ve learned the hard way that they do not do well on the feed for me. Cause that’s not what people are used to. but once I started putting those on my stories, So the engagement had already been up a ton because of regular means, but month over month, it went up 500% the the local ones were just so much more sticky and it’s so much better.So things like that, it isNathan: [00:40:42]There an example of a local meme that, that comes to mind that did really well?Ryan: [00:40:46]The best one ever. you know, so I didn’t even really know this until I started looking at the insights. Cause I really don’t know much about what I’m doing. I just figured out, I was like, oh,Nathan: [00:40:55]St. John.Ryan: [00:40:55]I didn’t even know you could share Instagrams. It’s a little bit harder than a post. Like, you know, how the procedures click the, a paper airplane, send it with a story.It’s not as intuitive. It’s like the three dots I think. And then you click share. So I didn’t even know you could share Instagram story, but I started seeing some of these memes get shared. And then there’s this one in particular that got shared. I think it was 130 times, which is my next, most popular one has been shared like 20 times.So this one just was incredible and it was, I, I, I don’t know anything about wrestling, but I think it was like a WWE match. This one guy is slamming this other guy to the ground. And I just overlayed the words on the guy getting slammed to the ground. It’s us trying to have a good time downtown and the slammer, I put the word tourists, because in the summer, Annapolis just gets overrun by tourists.It’s, it’s incredible. We need it because it’s good for the economy, but it also is just one of those things that, you know, you can always make fun of and people who live right. Will love it because there’s find it so annoying. So like, I, I now know what I can make fun of with the memes just because I know what people like, what grinds people’s gears, like make fun of parking downtown, make fun of the tourists, make fun of like the rich people that drive their boats down.This thing, we call it ego alley. it’s just like certain things always perform well.And that’s kindNathan: [00:42:15]Right.Ryan: [00:42:16]Learn doing it over and over.Nathan: [00:42:18]Oh, that’s interesting. Yeah. Cause there is that, that sort of thing. And what was interesting to me about it is that means, yeah, not something that I’ve used at all to grow an audience. So I feel like I’m, you know, as I see, on Twitter or what you’re talking about or everything else using that so effectively to grow an audience and spread ideas, I’m like taking notes.Cause I’m like, it’s not really my style, but at the same time, like I would, you know, the Boise equivalent of those names, I would die laughing, you know?Ryan: [00:42:45]But it wasn’t my style either. And that’s the thing is people are always like, are you just like super passionate about journalism and all this stuff? And I’m like, no, I just think this can be a great business. I just like figure out what I need to figure out. So I saw all these other people doing funny memes and I’ve never been good at internet funniness.Like I’ve been on Reddit for years, but like, Always posted stuff that I thought was hilarious and nobody else did like did awfully on Reddit. and so I was like, I would see, I saw this, Hey, Kingston guy posting stuff. And I’m like, well, I’m not funny like that though. And yeah, I’m not, or I wasn’t. And I say, now I am, because I just started doing it.I wasn’t funny in the beginning. And then I started to get a little bit better and it’s like realizing what people like and, you know, seeing the music Chris is making and kind of adapting them to be like, maybe I think of it and I’m inspired by it. It’s not the exact same meme, but like, it reminds me of a thing here that I can make fun of in a similar way.And so I just did it and got better. And I wasn’t good when I first started. And that’s, I mean, this is the thing that everybody needs to know about just about life is that most things you’re not going to be good at when you first started. I, I had this, my friends in college used to always say, like, I was good at everything I did.And it used to drive me nuts. Cause I knew it wasn’t true. I was like, no, I’m not. And then I started looking at it and I was like, yes I am. But that’s only because I only do the things I’m good at. So like, yeah, I’ll go. But you want to play ultimate Frisbee. I’ll go. You invite me out to play soccer. I’m not.And so I only do things I’m good at, so yeah, you do think I’m good at everything. And the first thing that got me out of that comfort zone was rock climbing because I love Heights. I’m like the exact opposite of the fear of Heights. I love standing on top of a thousand foot cliff and looking down it’s, it’s, a weird thing.It’s maybe a problem. I don’t know, but I always wanted to like rock climbing. I’ve never had done it. I just thought I would love it. And we had a wall in our school. And so I just started doing it and nobody’s good at rock climbing when they first start, because it’s really hard, never use the muscles like that.It’s just really tough and different. And I was like, no, I want to be good at this because I know I’m going to love it. And so that was really the first thing I ever did where I pushed through being super bad at it.And then actually got quite good at it. And haven’t done it in a year now because living where I’m living and I probably lost all those skills, but like, that was really what taught me.You’re going to suck when you first. And then just over time, you suck less and less.And so I’m super thankful for rock climbing one, because it’s really fun. But two, because I do think it’s part of why I am who I am todayNathan: [00:45:23]Yeah,Ryan: [00:45:24]Because I don’t mind being terrible at something now. I think it’s funny.Nathan: [00:45:27]Well, and then you’d be terrible at it for long enough and you get good at it. Just don’t quit.Ryan: [00:45:32]Yeah. Just don’t quit every day. You’re going to get good at it.You’re going to get what you.Nathan: [00:45:36]So you started, like you got into the local newsletter idea that you’re going to start at in other places and that didn’t work. And now, so you started it in your hometown. What, like where do you go from here? Are you now, like, now that you’ve got traction, they use that going back out and saying like, let’s start it in other cities or are you just looking to scale this one?What’s the path.Ryan: [00:45:57]No. I want a, what I always tell people is I want a hundred days. And, you know, in the next 10 years, I want to own a hundred of these cities, which is kind of crazy. It’s huge. It’s a big number, whatever people would say, it’s impossible. I don’t believe them. the, the only problem that I have is the resources like w obviously I can’t go write a hundred newsletters a day, and I don’t have the money to pay people and I don’t have the money to grow them.So I’m looking to get that somehow, whether that’s through creative, New ways to monetize this one to get bigger than it should be with just advertising or bringing on partners or investors. I never liked the idea of going out and raising money, but I realized now that like, yeah, that’s pretty much the only way to get where I want to go in 10 years.Otherwise it’s probably going to take 40 or 50 and, I just don’t. I love this and I absolutely love it. I’m willing to work super hard at it, but like, I don’t really want to work on this super hard for the next 40, 50 years. I don’t, I don’t see that being sustainable. Like I am exhausted the last 10 months.I can’t like you couldn’t do this for 40 years, 50 years. You, you would, you would die. You’d have no friends. Like it just, it’s not sustainable. I’ve heard a great quote. I think it was Jason. Calacanis saying like a startup is compressing your work life or your working career. As few years as possible by working as hard as possible.And that’s, I’m definitely not afraid to tell people. It’s like, that’s what I’m trying to do here. I want to be able to be done with this in like 10 years, if I want to be, if I don’t want to be, I can keep going, but I want the option to be like, no, in 10 years, I’m good on money and I don’t have to do this.So I don’t want to cause I’m just going to be so tired.Nathan: [00:47:43]IRyan: [00:47:44]You get that. You’re building a company in the same way.Nathan: [00:47:47]I feel it deeply more so than I believe I feel it deeply. So as we look to, or as you look to expanding into another city, how would you go about that as the first step to, to hire a writer there, find some local what’s the process.Ryan: [00:48:02]The first step would probably be to hire somebody to write in Annapolis and to do what I’m doing so that I could then spend more time. Focusing on somebody and ideally, you know, if the money’s there, it’d be great to hire somebody for an Apolis at the same time as the second city, because then you could train them at the same time.I’m like, just train them how to do what we need to do. And then we can set the person in Indianapolis loose and then go to the next city. And I can spend a little bit more time getting that one. Rolling. so ideally, yeah, the first people that hire a writers, I think, that’s kinda like, I don’t mind I can handle doing the growth stuff and I can, I can do that.That’s fine, but the writers are really, I mean, that was a key piece of it. That’s like it doesn’t happen without the writers. They are the most important part of it. And that’s like the priority as far as getting the money. We’ll see what happens. There’s I have a actually pretty large meeting about that on Thursday.So we’ll see how that goes.Nathan: [00:49:02]Fingers crossed.Ryan: [00:49:03]Yes, fingers very much crossed because I’ve had several people reach out, approach me and say, you know, we’d like to get on board with what you’re doing here. And, none of them I’ve been excited about until this one. So we’d love nothing more than to announce in the next couple of months that I have a really cool new partner and, and, and everybody will know who they are because they are a big.So I would love to do that, but we’ll see if that works out fingers crossed prayers. If you believe in that, I don’t know what you believe, but I’m definitely praying for that.And, yeah, I’ve really, I used to be like, no, I’m just going to bootstrap it. I’m going to go all the way. I’m going to bootstrap it.But now I’m like, no, to get it where you want to go, you need money. And actually getting outside money is not evil. You can still do whatNathan: [00:49:47]Right.Ryan: [00:49:48]As long as you get the right money, then you can, you can do what you want.Nathan: [00:49:52]Yeah. That makes sense. Thinking about number of subscribers and like the thing with a local newsletter that you always run into is that it does have a fixed, fixed reach to it. Write of, you’re trying to reach a specific population. Where do you think, like maybe first what’s your goal for the end of this year for number of subscribers and then where do you think it starts to cap out where you’re like, okay, maybe I’ve got actually everyone who wants.To follow this. And if I could get to this number, then I feel like I had market saturation.Ryan: [00:50:26]Goal for this year is 12,000, which is just about done. Now, it was 25,000 and I was like, that’s stupid. You’re not going to get that. and I very much am an optimist and don’t believe in telling yourself what you can’t do, but I was like, no, you need to be realistic. And if you make 25,000 your goal, just with the money that you have to spend on acquiring customers, like, you’re just going to feel like you failed this year.So make a more realistic goal and even getting 12,000. Yeah. So it’s kind of on track for that. It should, if it was going to do that though, it should have been at 6,000, like the 1st of June. but we’re not, not quite there yet, so, but, but it has been like starting to hit that exponential curve.So like, I think that the rate of growth will increase because of organic growth and the search stuff is starting to pay off And the social keeps getting bigger.So I think though that probably 40,000 is like the top, top, top. You’re not going to get anyone more. 40,000 of those 200,000 that could read it. That would be pretty insane. Market penetration.Nathan: [00:51:29]One thing that, add Sam part from the hustle on, we spent a little bit of time in his episode talking about local newsletters and that kind of thing. And one thing that, he said that was interest. Cause I was framing it as a total market size of being like everyone who lives in Boise or the Boise area.And he’s like, no, no, no. It’s everyone who has lived in Boise is thinking about living in voice. Boise has family in Boise, or is like, you know, has ever lived in Boise, right. It’s people who have ties that he brought up that, you know, the city that he grew up and he’s like, I haven’t been back in years, like for any meaningful amount of.But I still like, oh, I know that neighborhood. And I see it in the news. Right. Like I still pay attention to that. And I thought that was interesting that actually the, like the market size could be quite a bit bigger than we think we’ll see how it actually plays out.Ryan: [00:52:18]Yeah, I think that’s a definite thing to be aware of. I, I know Sam and I know that Sam. Likes to talk. And so he will say things like that and just be super confident in it. And he will make you believe that as you can run through a brick wall, cause he’s really good at talking.I think that is less of a factor. He would probably have led you to believe there. That’s definitely true. I have people that have, they tell me, they reach out and they’re like, Hey, my, I read this. Cause my son’s at the Naval academy or I read this cause I used to live here and I moved away or I read this cause I have a second house here and I spent half the year here or 25% of the year here that does happen.But I don’t think that’s going to swell the, the list size from like, oh yeah, it could be 40,000. If you really get your penetration to be like, no, it could be 80,000. I think that’s more going to be. You know, you could get 40,000 Macs in the area and maybe on top of that, you could get another 10%. And that would be like pretty intense because the thing is, you’re not searching those people out.You’re not going out and advertising for that. You’re all you’re relying on. There is people to move away and keep reading or to send it to friends who used to live there, send it to family. That’s really what you’re relying on. And I just don’t think that’s going to grow as fast. Cause you’re not trying to do that.And you can encourage that, but when you encourage something, how much are your subscribers really going to do it? I always write a different encouragement at the very bottom of email every day to share it with somebody new, I have written 122 emails. I’ve written 122 different things. So it’s been like, share it with your plumber, share with your electrician, share it with someone today who was a state championship athlete. Last week. I had one who was like, share with the person you’re going to call it a zombie apocalypse. So you could definitely do something like that where it’s like, Hey, share this with someone who used to live here. And actually I probably will doNathan: [00:54:10]Right.Ryan: [00:54:10]Cause I’m running out of ideas. I don’t think it’s going to be as big of a factor as we think,Nathan: [00:54:15]Yeah. No, that makes sense. It would be a 10, 20% lift on the total that you could reach. I think I thought of it because, right. Yeah. I thought of it because. Of the number of people like you do a filter and you know, I’m using ConvertKit for my newsletter. Of course, it’d be weird if I use anything else, but, you know, you do a filter down by location and see like, oh, 80% or 60% of whatever of our subscribers are in the Boise area.But then I’m like, what are the rest of these subscribers doing? You know? And, and some of them are friends and other people, but as I talked to more of them, I realized like, oh, you’re thinking about moving here or you used to live here or something else.Ryan: [00:54:54]Yeah.Nathan: [00:54:55]You know, we always wonder, cause Boise has this huge influx of population.If like advertising, like the realtor or Facebook groups or something like that would like somehow targeting the people who are moving here. It would be interesting.Ryan: [00:55:06]When you do it long enough, and you have like a big enough audience, you start to see patterns and, and how things happen. One of my very common emails I get is either a response to the welcome email, or usually a response to, I send an email a week after you joined and just say, “what do you think? How’s it going?”A very common, probably the most common response I get to that is, “We just moved here. This is the best resource.” And, so I definitely think that, and that is why I have put a lot of effort into becoming friends with the realtors in the area so that when they do sell houses to people who are moving here, they’re either talking about it on their stories on Instagram or their posts, or they just tell them maybe like, Hey, you know, you should sign up for this thing.I could probably start working some connections that I have with people who are giving their clients gifts and is like, Hey, you’re giving your people a Yeti mug, get clothes, like my business card. And, you know, I’m going to be interacting with you on Instagram and we’re friends and we’re pals. So like, you know, I scratch your back when you need it. You scratch mine here.Getting in with the realtors was one thing that I focused my efforts on very heavily, very early, and it has paid off and has the potential to pay off further. So that is a great idea.Nathan: [00:56:22]I like it. Well, I’ll have to spend more time with realtors if I’m going to keep growing, or as I keep growing From Boise, because we need to do the same.Ryan: [00:56:30]It’s not hard. I mean, just get them on Instagram, follow them, comment on all their posts or respond to their stories. Like that’s, it’s it’s not hard. It’s just a lot of consistency. It’s just showing up. It’s just not quitting everything.Nathan: [00:56:46]That’s right.Ryan: [00:56:47]Is a little bit about showing up on Instagram, though. I just get in front of everybody. Like, I like every post that I can find and comment, if I can think of something witty, just because I don’t want you to be able to go on Instagram and see like a business in Annapolis and not see, oh, like Naptown Scoop commented, and then you’ll see it 30 more times.And you’re like, who is this?Nathan: [00:57:06]Yeah. I mean, it definitely works. And then the businesses are paying attention. And then maybe they’ll do a sponsorship thing with you? or co-marketing in some way or whatever.Ryan: [00:57:14]Yes. It’s nothing that I do is, unintentional. Whenever I do something where I like doesn’t work out the way that I thought it could, or I can’t see the benefit, I’m like, ah, it was a waste of time.Nathan: [00:57:24]Yeah.Ryan: [00:57:24]And I don’t have time to waste.Nathan: [00:57:25]Well, thanks for sharing the details behind it. I’m curious to hear how it develops over the next couple of years, and where should people go to sign up for the newsletter or follow you? Any of that stuff?Ryan: [00:57:36]Yeah. If you want to sign up for the newsletter it’s a great way to learn about what’s happening in Annapolis. Even if you’re not there you go to NaptownScoop.com. I’m on Twitter is the only place I’m really on. I have a Facebook, but that’s only just to manage my ad account. I never post anything on it.So Twitter is where I’m at, handle: @sneddymobbin. But, this last two weeks has been, like I said, full on. I have not been put much on Twitter, but I try to, and I follow my own advice. If you answer or DM me on Twitter, I promise you I will answer unless you’re a spammer. I answer everything.Nathan: [00:58:12]Sounds good. Well, thanks so much for joining me and I’ll catch you later.Ryan: [00:58:14]Yeah. Thanks for having me, Nathan.

Cherie Hu is an accomplished musician, an award-winning writer, a columnist, entrepreneur, and self-described “professional overthinker.” Cherie specializes in analyzing, tracking and critiquing innovation in the global music business.Cherie earned her bachelor’s degree in statistics from Harvard, studied piano and music theory at The Juilliard School, and has taught as an Adjunct Professor at New York University. Cherie has worked for Forbes, Billboard, and Music Business Worldwide.Cherie is also the founder of Water & Music. Water & Music is an independent newsletter, research hub and community forum that is “dedicated to unpacking the fine print of commercial, technological and cultural change in the industry.”The Water & Music newsletter reaches over 10,000 free subscribers and 1,000 paying members. Subscribers represent numerous industries: music, film, fashion, advertising, gaming, investment banking, venture capital and more.In this episode, you’ll learn: How to leverage your life experience to dramatically improve your newsletter   Why freelance writers should focus on a core group of clients Why your audience needs a dedicated venue to find your content Links & Resources Zack Greenburg Forbes Billboard Music Business Worldwide Revue Greg Isenberg Kendrick Lamar Meets Quincy Jones on Hypebeast ConvertKit Creator Sessions Spotify Greenroom Twitter Spaces Tim McGraw Arnold Schwarzenegger’s newsletter Cherie’s Links Cherie’s Twitter Page: @cheriehu42 Water & Music Water & Music on Twitter: @water_and_music Water & Music on Patreon Cherie’s LinkedIn “Five Lessons From My First Year of Running a Patreon Page” Episode TranscriptCherie: [00:00:00]A 2015 interview between Kendrick Lamar and Quincy Jones, and Quincy Jones says the last two things to leave this planet will be Water and Music. I was just watching, and I heard that and it just immediately clicked with me. It’s been called a universal language for a reason. I liked that concept of always having that at the center, even of conversations about the business side.Nathan: [00:00:30]In this episode, I talked to Cherie Hu. Cherie is an entrepreneur journalist writer, and she writes about the intersection between music and technology. She has this popular newsletter in a community called Water & Music. We have a lot of fun talking about how she grew the newsletter, her journey from piano performance, through to math and then into journalism. We spend a lot of time in this episode on some trends in the industry, not just, crypto and things like that, but also, Spotify and podcasts, and how the world of music and podcasts and newsletters is all intertwined. It’s a fun episode.There’s a little less hard hitting tactics of, “Do this next to the newsletter,” and a lot more on: this is what’s going on in the industry and what you should pay attention to.Those are some of my favorite episodes, and this one is pretty great. So let’s dive in.Cherie. Thanks for joining me.Cherie: [00:01:25]Thank you so much for having me, excited to be here.Nathan: [00:01:27]All right. So I want to start with your love for music and the music industry. Where did that come from? You went to Juilliard for piano performance. Tell me more about it.Cherie: [00:01:41]Yeah, sure. Yeah. It almost feels like a past life at this point. Right? I guess to be more specific about that, I did the Juilliard pre-college program. It’s like a weekend program out of conservatory. And did that throughout high school where I would go to Juilliard, to the city on Saturdays, do private lessons, have classes in music theory, chamber music.And that, that was my path for a while, to just go to conservatory for piano and study that, and be a full-time performing pianist ideally. Very, very different from what I do now, but, still very near and dear to me. A lot of my closest friends, I kind of made in that environment, very intense, but fun environment.So, I guess my first and most intense involvement growing up with music was definitely on the performing and on the creative. At the same time academically, I was really into math and I was on the math team, did math competitions in school. I ended up majoring in stats in college, taking a lot of math and stats classes, but at the same time, a lot of music classes, and from a very early stag, trying to think about where those two worlds intersected.So, because I was more like a performer initially, I was thinking, applying math to music theory. I think that’s still a really interesting like application area. I guess also in spite of learning, studying piano for 10 to 15 years, I wasn’t even aware of the scope of what the music industry involved in terms of the jobs that were possible, the new kinds of jobs that were emerging, until I would say 2013, 2014.That’s when I had the opportunity just to explore, this career path, to do a two week, two to three weeks shadowing experience at Interscope. It was with their A&R team. In terms of like actual like tasks, I didn’t do that much because it was a short amount of time, but just that experience opened my mind, even to things like, like real questions, like what is A&R?I didn’t really know what that was before, being in the middle of it. And also at that time streaming had been around for a while, but I think that period of time was really when Spotify had just launched in the U S, and it’s really starting to pick up; Apple music with launch just a year or two later.So, the whole conversation around like who the main players were in streaming was also changing pretty drastically at that time. So, timing also plays a huge role in my journey to where I got to now. So, it’s kind of through that. I realized I was interested in maybe applying like my academic interests on the staff side to more of a data analyst, or data-facing role in the music industry, whether that’s at a label streaming service, music startup, et cetera. So, did a handful of internships kind of in that world, did some academic research on the music business from a tech perspective.So, especially looking at music, startups, and I’m super randomly at a career fair that my friend dragged me to, I very serendipitously read into my first freelance gig. I happened to meet an editor at Forbes there, his name is Zach Greenberg. He runs the entertainment coverage at Forbes, and he just happened to be looking for more music and tech connection. Columnists for the entertainment section, writing.So, this whole journey writing was never in the plan. I liked writing on the side for fun. I like had a blog that I would update for free occasionally, but I knew nothing about freelance writing freelance journalism, let alone newsletters, that whole world.But yeah, like very fortunately I think just my interest and my experience aligned really well with this, random, but really great opportunity to write about music and tech, for Forbes. So, yeah, that was my junior year in college. Very fortunately I liked that was kind of my way of diving headfirst into this world of writing.And, but very quickly I realized that writing is. Probably like personally my favorite and also think generally a really powerful. outlet for, especially packing, sorry, unpacking a lot of really complicated issues in music and tech. Like I was noticing at the time, in terms of like deeper analysis about what was happening in the music and tech worlds, it was mostly just kind of like one off news bites and headlines, not so much kind of deeper breakdowns of like the trends that were happening. So I decided to make that kind of my beat, like more like deeper enough. Of everything under the music and tech umbrella. So that could either be that you’re the biggest tech companies like Spotify or apple or the like, you know, latest emerging startups.I’ve, I’ve just like fell in love with the writing process, and I’ve stuck with it ever since. And yeah, I can talk more if that’s of interest of kind of how I shifted from that, to what I do now, which is, less freelancing and now like running my own newsletter.Nathan: [00:06:46]Yeah, well, I think that’s great. I didn’t expect, stats to be in there, like in the music to writing transition. Like I knew about, I guess the beginning and the end of the arc. I didn’t realize that math and stats and all that was, was in the middle. is there an element of that, but that’s still.I don’t know that, that you still use or is that sort of like, you know, that it was a phase of life, phase of college that you’ve, entirely moved on.Cherie: [00:07:17]I think in, in, in shockwave there definitely are, things that I’ve like learned are just like a more like quantitative mindset, definitely learning, not to take like a given piece of data at face value. even like, yeah, like very simple things, like understanding, be like correlations expected values, like in the context.Yeah, like understanding, Yeah, Anything from like streaming to ticketing data. it can’t be super valuable. Yeah. I usually don’t do kind of more like in depth, like hard coding, like data journalism, I’ve done a handful of those kinds of projects early on, on the side, I would say. Yeah.Most of what I do is, I guess like more like holistic, like business reporting, or like this is analysis, but, yeah, definitely just the mindset and the training.To, especially for like, a theoretical math proof. Like you might not necessarily connect that to the experience of writing an article, but just like the training that, that experience gives you to like really, have a sharp lens for like any loopholes in logic, for example, like, oh, this argument, like doesn’t really make sense.Like why are they skipping all of these steps or, yeah, I, I find like, not just in music, but in a lot of like business writing. A lot of people will make, you know, like just unfounded claims about anything and, people will kind of accept it as truth. So just, just that training to like really, you know, dig deeper into the actual reality of what’s happening quantitatively or qualitatively. I think that’s really helped.Nathan: [00:08:46]Right. Yeah.That makes sense. I mean, all of those things, I ended up serving people so much. Like we have a team member, who runs all of our, he’s an engineer, his name’s mark who work in Configit runs all of our onboarding and, and, like build out those processes for like the first one.You dig into his story and he’s like, got a degree in psychology and then he turns to marketing and then programming and all of this.And you’re like, oh yeah, I can see how all of those things like affect how you show up at work and why you’re so damn good at what you do, you know? But then you, like, you don’t realize that he did not follow a traditional path. Like, you know, like college, computer science, and then now I’m a programmer. It’s like this whole arc and it it makes for some really interesting viewpoints on the world. Like, you know, how you approach problems and all that. So I could see that showing up a lot in your writing.Cherie: [00:09:41]Thank you. Yeah, I’m glad. Yeah. I’m definitely glad that you pick up on that. I think, and this is something that I’ve definitely seen thrive in the world of, newsletters or like niche media generally, like B not being afraid to. I guess also not only focused on a specific beat, but also look outside of your beat for inspiration.Like I, loved diving into, and I think the music industry should do more of, you know, for example, studying lessons and takeaways from, the media world or from gaming or from film. Like there’s so many opportunities for just like cross collaboration and mutual learning. that I think is, yeah, definitely like under.Reported or kind of under-covered in media currently. So yeah, definitely in large part because of my upbringing and like really embracing that interdisciplinary nature. Yeah. yeah, so I’m, I’m really glad to hear that. It’s it’s it’s come out network.Nathan: [00:10:34]Yeah, well, maybe take us through, you know, so you’re starting freelance writing, you know, contributing for Forbes. where does that go from there through to running Water and Music now?Cherie: [00:10:45]So after college, this is, Around 2017 and fall 2017. I was very fortunate. And this is also a piece of advice that I would give to people who are interested in freelancing is, whenever possible, try to have, a small number of like regular anchor clients, but like publications you write for.So. I was very fortunate, not only to have this, you know, ongoing Forbes gig, but also a billboard at the time was looking for more tech coverage. So I was able to write a lot of tech articles for them. I had it, at, sorry. I had a column for music business worldwide as well under the trade publication, based in the UK. And I did do kind of like one-off pitches for other music entertainment publishing. But I would say those first three were definitely like my anchor, clients. And fortunately I was able to sustain myself on that for around two years. yeah, like very fortunately it wasn’t just like, you know, trying to just grasp, grasp at straws or anything.So yeah, it’s pretty regular cadence of like it’s freelanced, very specific, you know, industry facing tech coverage. At the same time, I did have, a newsletter that I started on the side. initially I use the platform review, which just got acquired by Twitter this year. and I wasn’t planning on monetizing it.It was just a way. to aggregate my freelance work elsewhere. and this is actually a point where I was, I was inspired by my reporting on the music industry and, you know, talking with especially independent artists, and hearing over and over again, the importance of owning the kind of relationship you have with your audience or with your fans, which is harder to do on social media platforms.I guess, in my case, as a freelancer, I was ha I was getting access to these, Huge, you know, legacy institutional publications, audiences that they built over years, if not decades, but of course I didn’t own that. the brand, the company owned that. So from an early stage, I did realize the importance of, owning, I guess, like my audience or having, at least some kind of direct outlet, to, you know, to my readers, to give them a direct channel to me as well.Even just like having that newsletter. Which, yeah, it was like a regular digest of my articles from elsewhere. was really interesting, like channel for sourcing. Like I definitely heard from people in the music industry who I would not have heard from like yeah. Who I’m not have heard from otherwise who like PR people would not have, I guess, like, served or like pitched to me otherwise.So, definitely, yeah. Grateful for that, but again was not really thinking about it, as a business at the time.Nathan: [00:13:20]Yeah.And growing that newsletter, were you able to have like the, in your byline go when you’re writing for Forbes or billboard, were you able to have a link off to your news?Cherie: [00:13:31]So, I think. As of now it’s still totally depends on the publication. So, with Forbes, you are able to customize your bio. Forbes has a lot of contributors also who do have full-time jobs elsewhere. So yeah, they’re pretty flexible policy of yet like sharing links to their company or like their other ventures, with certain other publications, Possible or it’s like, you have to go through a lot of like hurdles to even like customize your bio.Yeah. So it really does depend, with the exception of Forbes. I do think, other, sorry. Yeah. With the exception of forums, I think it’s mostly like smaller publications or like publications with smaller teams that are actually yeah. More lenient with that. but yeah, so I did get a lot of traffic from, from Forbes.Nathan: [00:14:16]Yeah, that’s good. I remember, I’m trying to think who it is. If it’s, I want to say it’s Greg Eisenberg, but it might be somebody else entirely. Cause I’m like attributing a random tweet that I read. He was basically talking about. You know, all this time is spent as a journalist writing for cure particular publication and, you know, like 50 million page views on his articles over five years or 10 years or whatever, and then going like, but I didn’t have a newsletter, you know, I didn’t have a way.And he referenced it. He was like, that is your pension, like as a journalist, you know, your retirement plan, your whatever else. The thing that you’re building is like that audience that you’re able to link off to. and I mean, that’s kind of how it, like you weren’t full time for any of these one, like any one publication, but you know, each thing that you wrote, you got paid for the article, and then you’re also able to get a little bit more of an audience, whichCherie: [00:15:09]Oh yeah, for sure.Nathan: [00:15:10]Allowed you to go, go out on your own.Cherie: [00:15:12]Yes. Yes, definitely. Yeah. So yeah, for the few publications, exactly. Like forums that where I was able to kind of customize and push the newsletter, or I guess also,I guess, yeah, the other tipping point in terms of the transition to now running my own newsletter, was starting to treat this newsletter, not just as like an aggregation of other articles, but as a source of original analysis.Right.So I would say like, yeah, that also around 2017, I started treating the newsletter more seriously as a place where you could,Iguess yeah. As an Aboriginal, you know, primary source for a lot of, especially my more like futuristic or like weird ideas about music and tech that might not otherwise necessarily fit neatly within these other publications I was writing for.I definitely treated it as a sandbox.And I actually saw a lot more growth, than previously, once I started making that shift to like, taking like, spent like, I guess dedicating time to, yeah, treating the newsletter as the source of additional analysis. And so I kind of did that for, around like a year, year and a half.And it grew to. where there was an established, I wouldn’t say community, but definitely like audience and readership. at that time of, you know, people who were interested enough in music and tech to like often to stay subscribed to these kinds of ideas, I was like, oh, maybe there is something here.Maybe I can try, you know? Yeah. I had like interviewed a lot of artists who, how to use Patrion and succeeded with it. and I hadn’t actually seen a lot of other writers take advantage of the platform. So I was like, oh, maybe there’s. Yeah place for like, I, this is a community that I would want also as someone who’s really interested in and like passionate about these topics.So, February, 2019 was a month. I decided to, launch the Patrion page from there. It’s still did take, a good part of a year, with that. And also like, I didn’t want to like, get rid of all my freelance income come overnight. I didn’t think that was a sound business decision. so I still. Yeah, kept that up for a good part of a year.Then th the timing is surreal, like a bit strange to think about, because it was, like February 20, 20, so like right before the pandemic, you know, change the whole world and just uprooted everything. when I was actually able to make the switch to. work on my newsletter full-time or like maybe equivalent of a full-time income from patron income.Bbut it’s yeah, super fortunate to be in that position and yeah, it’s grown thankfully a lot in the last year. I think as a people, especially the music industry have woken up to the importance of. Not just tech generally, but also being willing to experiment because there was like no standard in the pandemic.There’s like no standard, no rule for like, what does, like, what, what are, would not work? Because like, everyone was just like, you know, the live music industry was obliterated. a lot of artists just like lost, you know, the vast majority of their income. and I think a lot of people that environment yeah, were much more open to.New kinds of solutions, especially in tech for just, you know, connecting with fans online, let alone earning an income. So yeah, very grateful to be tapping that position to like help guide people through, this chaos and, yeah. So I guess like a year fast forward a year later, I just brought on two, part-time people to help.So now I’m thinking about hiring that’s a whole other, you know, question and learning curve that you of course have, have gone through as well. that, yeah, like kind of how to grow from just being like a solo newsletter operator to, you know, building a water brand where multiple people can contribute still figuring that out in real time.But, yeah, so that’s kind of the next phase of modern music this year.Nathan: [00:18:59]I like it. That’s fun really quick. Will you share the name, water, and music where that guy.Cherie: [00:19:06]Oh, yes, of course. So, yeah, initially, you know, on the surface, not related to like business at all, so maybe not the best name, but, but I like it. it comes from a 2015 interview between between Kendrick Lamar and Quincy Jones.It was on Hypebeast. I think the interview clip is still available.And at the very end, Quincy Jones says the last two things to leave. This planet will be Water and Music. And I was just like, killing time on the internet, like watching. I liked both of those. I like both of them as artists and as people. And I just was watching this and I heard that and just immediately clicked with me, like, you know, personally, that’s, that’s how I connect to music in terms of like the value it has in my life and the role it plays in my life.In hindsight there, if you really want to dig deep, there are a lot of, like similar or parallel, words, or like a similar vocabulary with Water Music, like waves and a flow. I’ve I’ve been like trying to make a list of those like, like puns related to Water Music. So yeah, it on many layers are a lot of similarities between the two.Yeah, and I just, I, I liked that concept. You know, always like centering music, as just something that so many people love around the world, it’s been called a universal language for a reason. kind of always having that at the center, even of like conversations about the business side.Nathan: [00:20:34]Yeah, I like it. You get people who get the reference right away orCherie: [00:20:39]No, that’s what you were wanting to know. I also think Quincy is only said this in. Two interviews that I’ve seen. So it’s probably probably a good thing. Yeah.Nathan: [00:20:52]You’re going to get them to say this a little bit more. Cause every time he says it, it’ll give us a little brand boost.Cherie: [00:21:00]There we go. Yeah.Nathan: [00:21:02]Okay. So I’d love to to throw some numbers in there. So if we go back to, I guess it’d be, when you launched thePatriot on like how many subscribers did you have and then on, you know, on the free side of the email list and then like, what revenue did you get over the next, like 30 days?Cherie: [00:21:19]Oh, gosh, so 30. Okay. The first 30 days, was not that much at all. And I guess also for more context, so the Patrion page, in terms of how I’ve communicated, its value to people. Has also changed pretty significantly between like 2019 and also 2023 now. So I started in 2019. I was, yeah, still mostly a freelancer people subscribe to my newsletter because they wanted to connect to me the individual, not so much like Water and Music as a brand.So I launched the patriarchy page.The same way that I think a lot of, artists, other artists, or like writers creators do on Patrion, which was as, as a more altruistic way for people to support my work, if they wanted to. And then as, as part of that, they would get access to, you know, this more specific community.You know, there’s a discord server integrated with the patron membership has a lot of, you know, other creators do on, on that. But yeah, but the framing was, you know, if you’re able to, we really grateful if you could support my work, I’ll like maybe write some exclusive, like articles, share some exclusive thoughts, for members only.And you can be part of this community. And so within 30 days, I, so the, the free tier at that time was, not more, it was around like 5,000, like 4,000, 5,000. So like not decent, but not. but so I still pretty small within the first 30 days. It was not that much at all. Cause I, I don’t think I like marketed it well, because I guess that wasn’t my goal necessarily.It was just like, you know, here’s a channel that’s available if you do want to and are able to support. So it must’ve been definitely on sub 100 people the first 30 days I say, so as far as conversion rates go, not very good. but yeah, again, like at the time I hadn’t really like settled on. you know, Water Music on the standalone brand.I think it was just kind of like testing the waters, by the end of year one. and I, I also published a, like a free recap, of kind of my first year of Patriana on LinkedIn. which I think if you search it on LinkedIn with my name should be able to find it. but by year, end of year one, I think I had, 250 paying subscribers. or I guess paying members is a term that,Nathan: [00:23:42]And the price from there started at $3. and and like what were the different price points at the time? Cause now it’s like $3, $10 and 15.Cherie: [00:23:51]So it was $3, which is the base parents just gave you base community access, $7, which is still like the main, definitely the most popular cheer today. It gives you access to. like exclusive articles. and also like now I do a lot of like research and gathering a lot of data. So access to kind of like research products, underWater Music.I, this process has been a bit delayed because of the pandemic, but I’m also writing a book on the side, about the concept of artists entrepreneurs. And so there’s a $15 a year, $15 a month tier that also gives you access to. I guess like, like yeah, book research,or like drafting updates. I kind of think of that as a kind of book advance, on the side that’s like crowdsourced and then, yeah, at the time I did have a tear, which I actually did.You don’t have any more and I can like talk through my thinking about it. I had a $200 a month tier that, was basically a way to fund like hourly consultations is how I thought about it. other patriotic. Yeah. So people who subscribed, who joined that tier, could have an hour long call with me every month.If they wanted to and just talk about, it was a lot of like startup founders, also people in the music industry who just wanted to, yeah, just like get more of my thoughts directly. One-on-one on a specific music. so yeah, I did keep that tier, on for a good part of a year as Water and Music and like the value I think of why people subscribe to the Patrion page has shifted from like a more altruistic, and like very individual focused, like source of value, like I’m subscribing and I’m paying for an access to like Cherie specifically to, More like, and so I think this is like maybe not the most, like positive term, but I think it is like the right way to think about it.Like, self-serving on the part of the reader. Like people are now paying for Water Music. because they want to get smarter about music attack that I want to like learn more insights on music and tech. It’s more for their own growth, as opposed to like more altruistic. oh, I guess the term I used in my recovery is utilitarian.Like it’s a utilitarian, community driven, but still utilitarian kind of. No reason to pay. as that shift happened, having like a direct consultation tier, that was very much tied to me. it didn’t really make sense. There was some kind of like clash with, kind of the branding and the ethos there, a Potter music.So I don’t have that anymore, but now I do have, in place of that, a lot of higher tiers work groups of, group subscriptions and group memberships. So there are a handful of, companies in the music and tech worlds that have come on. Like discounted group memberships, which, which is really great.Great to have more people on board also definitely easier to handle from like an accounting perspective. So, yeah. but yeah, so now, like it’s like now the tiers are from $3 a month. We’re still the lowest one to, like a hundred, $120 a month. But those are for larger groups of people.Nathan: [00:27:06]Yeah, I like it.And so then, like how many subscribers do you have on the newsletter now?Cherie: [00:27:11]So, I guess as of recording this, I haven’t, published the free tier in a while. I’m really focused on, like really honing the paid member experience. Yeah. So there are, around 1600 paying members. on, through the patron membership right now, the vast majority of them are also in discord server, but not all of them.And yeah, they’re all, I think that also represents the kind of pages under size as well. The free tier right now. as of the last time that I sent out an email, it went out to 12,000 people.I do want, I am going to revamp it and relaunch it this year. but yeah, I guess I think the paid tier is probably the most.Accurate or reliable, kind of signal of how big the community is just based onNathan: [00:28:01]Yeah.Cherie: [00:28:01]Of activities right now.Yeah.Nathan: [00:28:03]Yeah, that makes sense. And we had done like you and I met from, when converting acquired fan bridge. And then I can’t, and we did a live to an end to discord server, which was really fun because there’s just a ton of people really engaged and.Nathan: [00:28:19]When it comes to newsletters and all that school pay attention to like the total account.And they’re like, oh, you know, 2000 is bigger than 1000. And you know, we like count up from there, but we don’t ever think about, like, let’s say you were doing a piano performance in front of 1600 people. Like that is like, that fills a really good size, you know?Cherie: [00:28:41]Yeah.Nathan: [00:28:43]And so people are like, oh, like I only have a thousand people on my list.Or, or even if someone says, like I only have 10,000 people on my list. I’m like, that’s like a third of a football stadium.Cherie: [00:28:53]That’s a really good number. Yeah.Nathan: [00:28:56]That’s a lot of people. So I love that you have the, the smaller paid group that you’re especially investing in.But I’m curious about is why you chose that model, instead of saying another model of, monetization say like, Courses or, or books or like one time sale productsCherie: [00:29:15]Hm.Nathan: [00:29:16]Or even like sponsorships, you know?Right. Did you explore other models before settling on membership?Cherie: [00:29:24]Interesting question. I think at the time I, settled on membership just because that I think was the best. Model for also, yeah, I guess in the immediate context of launching the Patriot on page for people who wanted to support a writer or creator directly, I think having that like were regular, I was also thinking about, you know, as opposed to how freelance writing normally works and how writers normally get checks, like having a more, much more regular, predictable source of income.I don’t think like that about just the subscription slash membership model in general.Cause why would that, I have seen that. Again, this is not like a music specific issue, but, a lot of the biggest like trade publications, there are probably certain things that they can or cannot write about because of who their biggest advertisers are.I think it’s definitely, you know, common knowledge and it’s, it’s like a tricky situation, especially with like trade publications, I think, across business. And I just didn’t want to get into that, like situation did that conflict of interest. I decided to, you know, like, like just keep everything like ad-free for as long as I can, the one, area where I probably would want to bring in a sponsor in the future, is for in-person events.I think it makes a ton of sense to have a sponsor either like hosted at their office or, like pay for drinks, food catering, et cetera. So I think, yeah, that totally makes sense. So I probably will look more into that in the future, but, yeah, as of right now, I was just looking for kind of the.Simplest easiest to understand easiest, to handle like regular predictable sources of revenue and the monthly subscription slash membership model made the most.Nathan: [00:31:06]Yeah, that makes a lot of sense.I’m curious as you’ve been writing about tech and music and intersection yeah. Those worlds. What are some of those interesting things that you think are happening right now where you’re just like, you know, it’s the sort of thing that you’re out at, at, during your happy hour with your friends.And they’re like, okay, you talked about this a lot. And you’re like, no, but let me tell you more about that.Cherie: [00:31:26]This actually, I went, as of recording this, I went to, my first. Industry like dinner slash drinks event is literally a year and a half.Yesterday in New York it was very like jarring to like be in that environment. But by far and no surprise, like the top, the most popular topic of a night was crypto.And like the whole hype around NFTs, like where our music NFC is gonna go, are they useless? Like what is actually their purpose in the first place? So the world. Music NFTs and encrypto is particularly interesting to me right now because the music . Industry has been through this wave of hype before. I remember the very first industry conference I went to, personally was also the first time I even learned about what blockchain was.This was back in 2015. I mean even earlier stages. and it was a blockchain one-on-one panel and, and it ended up being a shouting match essentially between, this like representative from like very old school music industry, like from a performing rights organization, didn’t want to share any data, very skeptical about blockchain and, a startup founder who was essentially trying to disrupt that person’s company at that like really set the tone.In like a, in a maybe, you know, net negative way for just to how the music industry responded to blockchain, how they saw it as a threat. Unfortunately, this is a pattern, throughout, you know, the history of music, especially you look back at piracy, like seeing new tech as a threat, as opposed to, you know, adapting more to it and try to add value to it and then benefiting from it as a result.Yeah. The music industry has historically struggled with that, but I like about the. More recent wave of hype, even though of course. Yeah. There’s like tons of money being thrown around for, you know, who knows why around these, you know, digital collectible meme, you know, you, you, you name it these NFTs, is that there’s like less focus on how do we get these, you know, very, very large corporations, a lot of bureaucracy to agree, to share their data for this blockchain application to.We don’t need them. We’ll just, you know, start making money ourselves and like create entirely new kinds of markets and economies around art, music, creativity, et cetera. I personally am like much more excited by that. And I do think they have like bigger music companies are seeing that and being like, it’s probably not a good idea now to like stop this activity, but we do have to think about where our role, like what our role is in this ecosystem and how we can add value to that.So, yeah, that’s definitely like top, top of mind for me currently. something that is, will be really interesting to watch, especially in the next couple of months is how, what role, if at all, technology will play in the return to in-person life. probably another one of the big, like music tech, trends or shifts in the last year was, the rise of live streaming.And just, you know, the fact that Twitch, for example, now has a dedicated, you know, music team that’s really flushed out and a whole separate music category, on their page that, I don’t even know if that would have been feasible, you know, where it not for just the circumstances of the pandemic.A lot of artists were just, you know, not just performing shows online, but also engaging with, bands online through, through live streaming. and yeah, it’d be interesting to see, one like yo brother, the con, whether the concept of a live stream concert, will still be sustainable as like a standalone business model.There’ve been so many, like startups sounded that, in my opinion, essentially all offer the same service. I could be wrong, but, basically. Aloud bass ticketing, you know, bass like Twitch style interactive, live chat for a like, I guess for a performance that you watched through a screen. I think a lot of people would agree that it’s not as compelling.As you know, being in a venue in person, you know, being surrounded, you know, shoulder to shoulder by all these people who are all super passionate and excited to see this artist perform on stage. I, yeah, I, I personally am like much more excited about the line. That said, I do understand the importance of accessibility, and like, you know, making concerts more available, especially to people where it just might not be feasible for artists to tour there.So, that’s like one thing that they watching out for is how, you know, just this, unprecedented investment in live streaming, over the last year, how, if at all, that will carry over, to, you know, in-person touring, which a lot of artists, promoters, venues, et cetera, are like preparing for. Right.Especially as cities are reopening. hopefully I hopefully all that investment will not have been for nothing. but, but we’ll see.Nathan: [00:36:14]Well, yeah, that’s what I mean, what we’re seeing just on the ConvertKit side, pushing into music. And like we were one of those, those, companies that made the pivots related to the pandemic where like we took our entire. Budget. And since events were no more and we started running what we called ConvertKit creator sessions, you know, like booking these artists to do, highly produced at home performances and like storytelling and all of that.And like, none of that would have happened if it wasn’t for the pandemic. Cause the artists wouldn’t have had the time to do it. They wouldn’t have.Sure I’ll be hired for this. They’re like, no, I have like thousands of people in a, you know, in a concert hall, but I need to go perform for, so a lot of that changes, but then, yeah, I’m curious what, like what we’ll stick around, you know, it’s, it’s, sort of like the Clubhouse,Cherie: [00:37:02]Yeah, yeah,Nathan: [00:37:03]Rises like crazy, cause everyone’s like, I have nothing to do.Like it’s 10:00 PM. The kids are in bed. I’ve watched everything. There is on Netflix.Who’s having a conversation about the future of the music industry on Clubhouse. LikeCherie: [00:37:16]Yeah, exactly.Nathan: [00:37:18]Like I’m in, you know, from 10:00 PM to 2:00 AM, like. Sure. and then now, like if you would tune into some of those sessions, there’s nobody in them. Right. Because we’re all at happy hours, we’re, you know, like flying outside if we’re, you know, doing any of that. And so it’s, it makes me curious what of these things.There’s so much that changed over the last 14 months and what’s going to stick around, you know, and then, and what’s going to revert. do you have any take on which things you put in?Cherie: [00:37:50]So yeah, just thinking about it this week, because Spotify, just like launched their own Clubhouse competitor. they, I guess they’d acquired locker room slash Betty labs, which was kind of a, they’re developing a niche version of Clubhouse, more focused on sports. Yeah. Spotify, bottom relaunched, a Spotify Green Room this week.And I think so. Okay. One, one really interesting shift that I have seen Clubhouse make. I don’t think we’ll make it easier for them in terms of like surviving as a sustainable platform is that they seem to be shifting their branding from being an audio driven social network where, you know, you can lock on a Clubhouse and, you know, meet all these people from all over the world who have similar interests who otherwise would not have met on Twitter or Facebook.Like that was a draw to me early on from that to like a very, like programmed top-down. I think if it’s just like a live radio network. So if you think about how they have a whole like, actually both Clubhouse and Spotify and, probably some other companies in your future, they have these creator funds.So they’re funding. These shows that are going to be happening, you know, programs on a regular basis on the app, on Clubhouse. Even just like tiny features, like the ability to, type in a text chat in real time during a conversation and Clubhouse still doesn’t have that. And so it also is very, it’s a very dramatic difference.Like you’re either, on the Clubhouse stage and you’re, you know, like leading and you’re interacting or you’re company, the passive there’s no, like in between. And I think a lot of the, if you look at like Instagram lives or like Twitch, sessions, Twitch chats, a lot of the entertainment or like social communal value is in that kind of middle ground of interaction.Like being able to even like react with an emoji, let alone, you know, like type in a text chat or request, you know, like ask a certain question in text form. So, and Spotify does have like the kind of text feature that Spotify greenroom. So, yeah, so I, I am like noticing this, this shift towards, yeah, like funding, more formal shows focused on developing IP.I feel like the companies. We’ll succeed the most at that are companies like Spotify that already have that IP. So if you like open the greenroom app, I opened it yesterday when it first launched. And of course at the top of my feed was the ringer, which Spotify owns. and they were, you know, recording their like NBA podcasts with like bill Simmons was a guest briefly.So, you know, of course like Spotify now has that whole, I guess has like completely verticalized. Podcasting like every step of podcasting within its own company. So totally sense that they’ll use Grievant to kind of promote those shows. I do think so. Twitter spaces, I think is. Like has it interesting with different territory?I think they have a vision. That’s more about, holding audio rooms within specific communities. Like I know they’re working on building like a Facebook groups, competitor, like on, on their own platform. So you can like, host a.Twitter spaces chat only for people who follow a certain topic like VC.I think that makes a ton of sense discord, to their credit. They’ve had voice chat within like closed communities for several years. and now they, but they also have like a more, you know, properly stage like Clubhouse clone feature now. so it’s just a matter of like other tech companies catching up. So, but for, I guess, for those to like sum all this up, and those specific models of like, I guess social audio as a, communal feature, like a way to connect with other people that is very, it’s very, very hard to compete. I think with, these bigger social platforms that already own those social graphs, like try to create a whole new social graph through audio is, is really difficult.I think Clubhouse like really captured lightning in a bottle, like throughout last year and did do that for some people, but not.Yeah, all these other incumbent companies coming in, it’s really hard to compete with that. And then for like the, the live radio podcast network model definitely companies that own,I, I guess Spotify is, is in a unique position because they both own IP. And one of the biggest, you know, streaming platforms in the world, for, for audio, at least. So they’ll probably be the leader in that, but, Amazon now owns a podcast company they own Wondery. So it’s also like only a matter of time, I think before. other like other companies, other streaming services come in and compete for that model.So that’s kind of like the two areas that, that I’m seeing like fragmenting right now.Nathan: [00:42:34]Yeah.It’s fascinating. The amount of money that is coming to play in the space, you know, even.I think you see examples of this in acquisitions when like Spotify acquired Joe Rogan’s content, you know, acquired his show and, or I guess just exclusive rights to his show is all day quiet, but their stock price went up by so much just off of that announcement that it like way more than paid for, you know, so they were like, that was free.And so, you know, from a grassroots perspective, there’s not really. Because there’s so much money being thrown around that. Like, I don’t know that you can compete with these other platforms. Cause like Spotify is going to say, this is our platform. Oh yeah. And we’re already going to funnel everything that we have in here, you know?And so that, that’s just fascinating to me. Another thing on the Spotify side that I onlyrecently learned, actually from talking to people at Spotify. In their business model in hindsight, this makes perfect sense.But in their business model for music, they pay out substantial fees to the artists, all of that, right?There’s all kinds of licensing who owns the masters, who owns that individual recording, who wrote the song, oh, you like that? You know, the little bit of money for every stream gets parceled out so many different directions and it can be very company.Cherie: [00:43:59]Hmm.Nathan: [00:44:00]And in podcasting, it’s very simple, you know, in fact, all these odd casters, like a podcast stream, like someone who’s listening to this episode on Spotify right now is worth just as much as Spotify as like a song stream,Cherie: [00:44:15]Hmm.Nathan: [00:44:16]Have your attention.They have you.Cherie: [00:44:18]If anything it’s worth more because, I guess in, yeah, if you’re listening to music then, I’m actually, I’m not sure about like the actual fine print, but yeah. Listen, like they have to pay exactly. Except like 70% of their revenue,Nathan: [00:44:35]Right?Cherie: [00:44:36]Music to like rights holders. Whereas like podcasting is like a whole separate pool. Yeah,Nathan: [00:44:40]Yeah. And for, for better or worse as a podcaster, we’re not, we’re not going like, Hey, where’s my car.Cherie: [00:44:47]Mm,Nathan: [00:44:48]You know, cause we’re like the expectations, like you don’t get a cut, you know, you monetize through sponsorships through your other thing. And so Spotify sitting back like, yeah, I know you, of course you don’t get a kid.No one gets to, you know, when they’re over here and like going,Cherie: [00:45:00]Yeah,Nathan: [00:45:01]A way better business.Cherie: [00:45:02]I think the, yeah. It’s oh gosh, a whole other issue. So yeah, I do think in that. Podcasters are going through an almost like worse version of what, independent artists have gone through in terms of their critique of Spotify and like lack of, leverage and yet kind of like lack of this sense of they are also benefiting from the growth and, you know, Billy dollar valuations of, Spotify as a company that said, I, I do think kind of on the flip side pod-casters right now, could be a blueprint for artists in the future in terms of like Spotify, for example, and also apple they’re investing in a lot of like direct to podcaster or direct to podcast monetization models like apple, like they both are working on pocket subscriptions, apple just launched their, you know, pockets.Like show level subscription model, this month, and a lot of people in the music industry have been like, what are their biggest critiques of Spotify from the artist perspective? Is that it really there’s like few, if, any ways for the artists to be able to connect, to communicate with fans like that is, not the purpose of Spotify, the purposes to just make it convenient, to access all these millions of tracks, make it really easy to discover artists, but not really.Strengthen and maximize the value of the artist’s fan connection. and some people also joked, and like the Water Music server. Oh, like what’s stopping and artists from. Just releasing their songs as a paid podcast. And like maybe making more royalties from that probably probably they’ll run into like, if they own all their IP, they own all their copyrights. They could pull that off. If you don’t of course, like probably brought it to some kind of licensing issue, but, I’m glad those conversations are happening.You know, just the, yeah, the model of getting paid, an average of just a fraction of a penny per stream. Isn’t the only way, like, look at these other creators on the same platform that we rely on every day.They’re now able to make, an income directly from their listeners and supporters. Like why shouldn’t there be, that same option for, for musicians, for artists. So, I, I think that, yeah. That awareness of different, you know, models, business models for like on the artist level around streaming. And they’ve been really good, but yeah, to your point, for, for Spotify, it’s podcasts are just an easy way to kind of circumvent licensing and, really, I think they are trying to become the major label equivalent in podcasting and how aggressive they are about acquiring IP.Just because it doesn’t exist, maybe it’s harder for them to create these like direct to artist subscription features, for example, And music because they have these relationships with the existing major labels and they can’t really like tarnish that if they want to keep music on their platform.So definitely lots of, lots of layers there.Yeah.Nathan: [00:47:59]Yeah. And it’s fascinating. We’ll see a lot more, you know, like the Joe Rogan deal or the ringer or those sorts of things really stood out.But now like just the other day they announced the call me daddy podcast w was acquired.Yeah,Cherie: [00:48:14]The deal. Yeah.Nathan: [00:48:16]That’s amazing.There are startups that have raised crazy amounts of funding that don’t sell for $60 million. Yeah, so that, that, is fascinating. Let’s, let’s bring this conversation to thenewsletter side of things, because in, we have a lot of the same dynamics happening, or like same tensions happening in newsletters between large publications and solo newsletter, creators, and, and all of that.And like you’re as much in the middle of that world as you are the music side of it.So what are you seeing? And what’s your take on it?Cherie: [00:48:48]Yeah, I, oh, gosh. Yeah. I think about this all the time. I think there are a lot of parallels yeah. Between, I guess, thinking also on the, so yeah, sorry to backtrack. So there are multiple layers. You could look at this. a lot of like media companies and music companies face similar, challenges with, tech and social media platforms.For example, like the, the relationship between, like media companies and faces. it’s quite similar to the relationship between like labels and Spotify in terms of that tension of you know, who has more power, this, this struggle always with like, not be able to control the context in which, you know, you, I guess your work is delivered fed to potential readers or potential like audience member.The fact that Spotify is also even now, you know, creating a, an advertising product where artists and labels have to pay to reach certain fans that is literally a copycat of, you know, these existing social advertising platforms.So lots of parallels on that level, on the individual creator in this case like artists or writer level, actually think in some ways, writers, the, the individual writer situation is even worse than the music.Because I, so even with like the recent, you know, newsletter, boom, as a freelance writer for income, I feel like you do. Immediately rely a lot more on these by-lines of bigger publications to like, make a name for yourself, let alone earn income. There’s just by nature of the like freelance economy.It’s, it’s really, really hard to, you know, build a newsletter from the ground up. If you don’t already have like access to those bigger audiences. Somehow I think that is a reality of, of running a newsletter, especially from scratch. And there is a whole wave now of, like freelancers, actually very similar music, like freelance writers, try to unionize like collectivize around, you know, also asking for a better terms, in freelance contracts.But like a lot of the times. Yeah. So not only do you, like a lot of writers rely on these bigger, like brand names to, earn income, but depending on the publication, you, You might not, especially if it’s a bigger one, you probably don’t own your own IP. Like you’re spending hours and hours doing these interviews, writing these articles, but the, but the publication ultimately owns them.I think is the Washington post, is like in the middle of the controversy this week. as it recording because they are like making it a lot more difficult for writers to even like talk to, like an agent, a talent agent, if they want to like write a book. So like, I guess that’s more in the case of full-time staff, but it does translate to freelance contracts, like, you know, the right to use, this article you published in like a book they might write later on. So lots of, yeah. Parallel issues or like leverage around like IP ownership. and yes.So I do think now with, with newsletters, I am surprised that there aren’t more musicians who, like are investing heavily in newsletters in a capacity. That is not just like marketing. So like if you subscribe to exactly. Like if you subscribe to especially more on the label level, like a universal music groups, like newsletters, it’s just pure marketing. There’s no sense of it being like personal, not even like deeper copy. It’s like let’s just images and links to, you know, stream us on Spotify.Maybe it’s because like, not all artists are like comfortable with. Crafting and like writing these more long form, like text experiences, which, maybe that makes sense. but yeah, so, so now I do think in terms of like the newsletter academy of, I guess I’m thinking of like sub stack being the prime example of these, like, you know, individuals stand out personalities, building their own newsletter brands.Writers are definitely like leading the way in terms of that, like direct to bat. You know, or direct to reader direct to supporter, kind of like channels and income than the music industry is right now. but yeah, like historically there’ve been a lot of parallels in terms of issues that, that both like creators of both worlds have faced.Nathan: [00:53:13]It’s interesting what you’re talking about. Cause you’re, you’re absolutely right. That not very many artists. Personal like behind the scenes, get to know me sort of approach. A lot of small artists will do that. People who are up and coming and getting established, think about artists that are on like convergence platform that have been on for awhile, even like Tim McGraw, like he’s been on our platform for quite a bit, and it’s still a bit of a push to get them to do more storytelling and less marketing, you know?To make that distinction because they’re like, oh, here’s a single that’s coming out. One thing that they have done is like more behind the scenes video and things like that.And so we, as part of the reason we’ve built into ConvertKit like native video integrations where you can play it directly in the, by the video drip email, because like talking just with Tim’s team, for example, They’ll be sitting down to film something big and then they’ll be able to get them to film for like five minutes talking directly to fans, you know?And that’s like, okay, we’re already here. We’ve got a studio set up. Like, yeah,I’ll record something for the newsletter. The example that I love to see more of is like, oh, Schwartzenegger runs a ConvertKit newsletter and hit, this is so good. It’s like all the behind the scenes and the stories and like answering fan questions.Why, I dunno, what would it take to get Dereck to do somethingCherie: [00:54:36]Yeah, yeah,Nathan: [00:54:38]It would be amazing.Cherie: [00:54:39]Yeah,Nathan: [00:54:39]Be phenomenal. So, but that, that pivot hasn’t happened in music yet.Cherie: [00:54:45]Yes, I guess you mentioned Kendrick specifically. I think he’s a great example of an artist who is so revered and respected and it’s just like so talented. and like everything he does, but is also very private, like aside from album releases, he will like rarely do interviews. you’re very lucky that you can just get a handful and yeah, so this is on social media. Instagram, YouTube just very like quiet most of the time. and that works for him.I do think. Yeah, it is important for artists or musicians generally to like not let the tech Dick, I guess not let tech tell you what to do. Like.Only invest in yeah. Channels that you’re comfortable with that align with like what you’re really good at.Yeah. Especially with, I guess like text-based storytelling or more personal storytelling, like newsletters are great, but if you’re like not ready to do that, that’s fine. you know, you don’t have to, so, yeah, I think it’s, there, there is a bigger, I guess, trend to APAC in music as well of, This expectation among a lot of fans that artists are almost like a friend. I think this is the, like the, impact of social media also extends to like influencer culture. Like, oh, I’m following this influencer on Instagram. I, I saw what she had for breakfast. So clearly I’ve, you know, in her circle and like, I might as well be his, her, their, you know, their, their friend, and that like requires a lot of openness and vulnerability.That means. Yeah, I think certainly not all people let alone, not all artists are comfortable with. but yeah, I’ll say like the slow, steady rise up these letters. It’ll be interesting to see how it like meshes with that trend of just expecting artists to be a lot more vulnerable and open live streaming.Certainly. I think like fits into this category as well.Nathan: [00:56:32]Yeah, I think so. I, I mean the trend of only continue. So, and then like, as that’s been established, many times over email is not dead. Newsletters are on quiet, quite a ride.Maybe bringing it back to, you know, to Water & Music and everything that you’re doing.What are you looking to do next? as far as maybe the next milestones for Water and Music.And then how you think about growing to get to those? Like, what are the things that you’re doing to grow the audience or grow the revenue?Cherie: [00:57:00]So yeah. Next steps. There are a lot of, yeah. As different moving parts. So, I guess earlier I really briefly mentioned events. I think that will be really important. I guess after the pandemic kind of dies down and conferences come back, for example, as like an individual freelance writer conferences, where, by far like one of the most effective, just like marketing, audience, building networking tools, especially meeting people, in the music industry specifically who, who, yeah, I would not have met otherwise kind of through more formal, like PR interactions or interviews.So, definitely wanna invest more in that, especially around those kind of like industry conferences that happen every year. A separate new Water Music website is in development. that will definitely be a milestone in terms of being able to have much more control over the reader journey. Like the reader experience, making articles like I’ve published, I think over 150, like articles slash posts on the Patreon page at this point, but the search functions on Patreon are not the best.Very open about that. So definitely want to, yeah. The website would really help out with that. So that that’ll be a big milestone, definitely like hiring is like something I’m also like figuring out in real time in terms of what’s the. Like combination of people to bring on. So right now I would say the three pillars of a Water Music does, is like editorial, like long form editorial analysis.Research, very data, heavy research, and then, community in terms of your discord server and our Hangouts. So, in terms of like hiring, bringing on more people to help like manage all those three different parts that like work together, in a really, and so it works good in, in, in a really complimentary way.That’d be a big priority for, this year as well. yeah, I guess like the only other thing that comes to mind. And I don’t, I haven’t like figured out how to like formalize this or structure this. but going back to this notion of interdisciplinary, thinking about the future of music and about energy.I do think, you know, we were just talking about, Clubhouse and Spotify Greenroom, and podcasts. A lot of people might think of that as a podcast story, but it absolutely is a music story as well, because it could, you know, like Spotify pushed that feature like a new app to artists. And I think the music industry could use those kinds of features in really interesting ways.So that’s one example like music and podcasts conversion. Music and gaming. of course I think are, are converging a lot more, especially looking at the last year. So you know how to build and expand editorial coverage in a way that reflects that. that’d probably be into more in the form of like hiring more people who are able to like, who are experts, not experts, but are like fluent in like multiple areas of entertainment and how they merge together.Very like specific kind of, I guess niche, view on, on business, but definitely something I wanted to like take more seriously in the future.Nathan: [01:00:06]Yeah.Yep. That makes a lot of sense. Well, I’m excited to continue to follow everything you write about the industry and all of that. And for anyone else who wants to do the same, where should they go to follow you online and subscribe to the newsletter?Cherie: [01:00:20]So definitely the best way to learn about what, Water Music and all the different parts of membership is just to go straight to our Patreon page. it’s patreon.com/WaterandMusic, and all spelled out. I’m on Twitter @cheriehu42.You can also find the Water Music Twitter (@water_and_music) in my bio also. So you can follow, the membership slash newsletter there. And yeah, hopefully you can, hopefully those of you who are listening, some of you can join the Patreon page and you can find me in our Discord server as well.Nathan: [01:00:56]Sounds good. Well, thanks for joining and, and, we’ll talk soon.Cherie: [01:01:00]Yeah. Yeah. Sounds good. Thank you.

Jack Butcher is the founder of Visualize Value, a design, consulting, and educational company in New York City.Jack spent 10 years working in advertising for Fortune 100 companies as a creative director for multi-billion dollar brands that include Amazon, Nokia, McDonald’s, and Mercedes-Benz. It was a job he found enjoyable but constraining.In search of freedom, Jack started his own advertising agency, which he describes as “No fun, and even less freedom.” However, after two years of iteration, Jack figured out how to transition to highly specialized (and fun) consulting, and a product business that scales infinitely.Visualize Value is the product of that transition, a project Jack has used to build a network of mentors, a $1M/year product business, and a media platform with an audience of over 500,000 people.In this episode, you’ll learn: How to use your unique skills to stand out on social media Why repetition in your design is the fastest way to build your brand How designing for niche markets makes your job much easier How to scale your business without compromising quality Links & Resources DHH on Twitter: @dhh Jason Fried on Twitter: @jasonfried Basecamp Nick Huber on Twitter: @sweatystartup David Perell on Twitter: @david_perell Write of Passage Brian Norgard on Twitter: @BrianNorgard Anthony Pompliano on Twitter: @APompliano Maven Adviser Jack Butcher’s Links Jack’s website: Visualize Value Jack’s email newsletter: VV/155 Jack’s Twitter: @jackbutcher Visualize Value merchandise Visualize Value on Twitter: @visualizevalue Jack’s Instagram: @jckbtchr Visualize Value on Instagram: @visualizevalue  Build Once, Sell Twice Episode TranscriptJack: [00:00:00]You build something digital that runs on code or media, and can be served up infinitely at zero cost replication to you, something like a product or an information product you build at once, and you can sell it to a hundred, a thousand, 10,000, a hundred thousand people. The bulk of the value is created once.And then just becomes a game of how effective are you at spreading that story and reaching people that need the thing that you’ve done. Nathan: [00:00:37]In this episode, I talk to Jack Butcher. Jack has a really interesting visual style where he’s taking these complex concepts: it could be leverage, it could be this idea of build once, sell twice (that I’m super jealous of by the way), how he framed that… any of these things, he takes them and distills them down to these graphics:Black background, white text, white line drawings, slightly pixelated looking. It’s very distinct style and he’s used it to build a massive following; well-over a hundred thousand followers in social media, he built his email list, he’s doing fantastic revenue from courses. So, we dive in on what it takes to be unique.How a lot of marketing Twitter, you know, marketers talking about marketing is repetitive. A lot of people don’t have a unique angle on it. And so how he makes unique content that’s more interesting and engaging and stands out.How constraints really drive that.We talk about a lot of other things, exactly how he makes money and monetization. There’s a lot of great stuff, who inspires him, so much more. Jack’s someone that I’ve wanted to have on this show since I started it. And so I’m very excited to talk to Jack. Let’s dive in. Jack, thanks for talking with me today.Jack: [00:01:49]Thank you for having me, man. I appreciate it. Nathan: [00:01:51]Okay. I feel like so many people on the internet are—especially in the content marketing audience growth space—are doing the exact same thing as other people, you know, it’s just like, it’s similar playbook. Everyone’s going over it repeatedly. The amazing thing is that it still works. You don’t actually have to innovate that much to make like a hundred grand a year or more on the internet, which is mind blowing, but then you come out and you actually have like a really unique visual style.You’re doing something different instead of just like another random tweet thread, or like summarizing the same quotes that everyone else is doing. It feels like you’re doing something unique. And in, you know, in these little graphics, you’re explaining these same concepts that everyone else has talked about, but in a really condensed format.So, I’m curious, well, one, let’s just start with where that came from, and then I want to get into like what you think other people should do to differentiate and not be the same. Like, you know, it’s just copying everybody else.Jack: [00:02:52]Yeah, sure, so very quick background. I studied design in school, graduated in 2010. That was in the UK. I moved to New York and started working agency jobs in basically every different capacity. So design art direction, creative direction, worked for small boutique agencies that would build like, small brands to big global behemoths at work on like.Multinational billion dollar brand campaigns. And one of the skills, one of the skills I built up, I think, across all of those experiences was working on pitch decks. So what all of these different ad agencies have in common is you have to tell compelling stories to get the opportunity to work on a project.But the pitch deck is kind of a work in the agency, right? Nobody wants to be the last one in work on the pitch deck, waiting for everybody’s emails to say include this, include this. So, early in my career I sort of got stuck with that by default, but for whatever reason, not quite into it quite, enjoyed the process of distilling all of these different people’s ideas that would come at you from all different parts of an agency or trying to convey something to a business.Basically tell their story back to them in a more compelling way than they’ve ever heard it told. And that’s essentially what gets you the opportunity to work on these projects? So, yeah, a lot of late nights working on pitch decks was the, I think the eventual catalyst for visualized value as a style, I went through a ton of iterations to get there.Worked at agencies for eight years, started my own agency and then slowly narrowed down the type of work I was doing as an agency to that really, , specific aesthetic and that very specific deliverable. So before visualize value was a media company, it was a very highly specialized service business agency.Nathan: [00:05:13]Testing testing like in those pitch decks, were you creating, , graphics to distill these concepts down rather than using, you know, words or like, I’ve seen a lot of agency pitch decks over the and most of them are a decent amount of words with like, you know, someone went on the agency version of Pinterest and like mood board or something to go with Your style is very different from that.Jack: [00:05:39]Yeah, so I, I tried to, I try to differentiate because you know what you’re going to be up against with all the other agencies you are going to be up against the bulleted lists and the Pinterest mood boards and things of that nature. So what fascinated me and I think was a, , an edge in some of those environments where, you know, how can we visualize the…Either the opportunity. So some of the like some of the things came from understanding, like where our brand was positioned in the market and how to visualize that for them. Like here’s, you know, here’s where you’re positioned relative to competitor X or this, or here’s like a way to visually contextualize where your product is or who would buy your product.And that, that idea of translating those things that other agencies would show up with as like five paragraphs into one illustration is really the, I think the moment that you’re trying to create is, ah, the, this agency or this person really understands us and they can quickly summarize what we’re about because that’s what essentially what you’re pitching them as a service.So the first opportunity you get to demonstrate that you can do that is in the pitch deck. And the irony is that you don’t get paid. Well, that piece, that’s the thing that you do on spec and you compete for, and you spend agencies spend tons of money putting together pitch decks that you end up going nowhere.But, and that’s another reason why I think you have an opportunity to knock it out of the park too, is because there’s a, you know, a lot of people phone it in. So, , yeah, that’s working on that process and just having to, I think the other piece of it is having to stand in front of a room of people and, and walk through these things.Like, I was at that point in my career, just like so nervous about telling the story correctly, that I just wanted it to be so Bulletproof that I would go over and over and over and over it and, , refine it to where I felt completely confident explaining it. And the longer you talk, the less confident you sound.So I was just trying to distill it down as much as possible.Nathan: [00:07:57]Yeah. So did you notice, like those pitch decks really working and did you get credit for winning those, those deals and all of that?Jack: [00:08:07]Yeah, I would say, , there’s definitely a hierarchical structure in agencies where you, you don’t necessarily take the full credit for winning the business, but you’re the person who gets asked to work on the next pitch deck as a result. Right. So my role went from working on the business after it had been one to just being sort of like on the pitch circuit like that, you know, myself and a couple of friends, , strategists and writers you’d have this team of people that consistently can come in and take, , yeah.Take a, take a story and turn it into something super compelling and then fly somewhere. I present it when the work, and then you go on to another pitch and that’s a whole nother conversation about why agency businesses, at that scale are difficult because the people who are great at pitching are rarely the people who fulfill the work after the fact, because it’s the ROI on them pitching is so much.Nathan: [00:09:08]Yeah, I mean, at this point you’ve become. Like the best sales asset that they have. like, of course, we’re going to have you work on implementing it rather than, or sorry, on, on pitching rather than implementing, which then gets into a problem because you’ve demonstrated, like you understand the customer’s problem better than anyone else in your, even the one I’m working on.Jack: [00:09:29]That’s, that’s the that’s the game is it’s incredibly frustrating, but it’s also just like that human incentive behavior thing playing out perfectly.Nathan: [00:09:39]Right. So what were the, like, , your style now, you know, is these black images with, you know, light text and just really simple line illustrations and all of that. What were some of the early iterations of that? Like what did it, what did it go through to turn it into that style? Jack: [00:09:58]Certainly more complex at times. So when, when you would do it for a brand, you would take their color palette. They’re static they’re , that type face, whatever type face they using. And, it was still the there was still these like, I guess diagrammatic elements were consistent. So it’s gotten over the last maybe two or three is, is less reliant on style and more reliant on substance.So if I look back at something from two years ago, it may have looked. For, but there’s no like underlying logic to it or there’s less underlying logic to it. So I think, , just making that shift from relying on these like stylistic decisions is huge too, where if you can choose to of constraints, it becomes more about communicating the idea, then picking the color, making the typeface look interesting, like composition, all of those things.So, ending up there one for like function. So you show up and you’re not spending two or three iterations of the thing, just working on, , stylistic decisions, but also the equity that you can build by showing up with the same aesthetic every day. Right? It’s like after you’ve done it a hundred times, people don’t even need to read the name above it.They know where it’s coming from in the same way. A lot of established brands have, you know, you could recognize a Delta ad on the side of a bus based on. The typeface and the photography and the color scheme, all that kind of stuff. So that’s another hold over of what I learned in the agency world is you can never, you can never be too repetitive.Visually. I have a friend who’s got this great quote said great advertising, whereas in not out. Yes. And I think a lot of people, especially creative people, don’t like you abandon something before it gets recognizable.Nathan: [00:11:58]**Yeah. So that’s interesting. I’m a huge fan of constraints. I feel like you, you know, well, you and I have similar backgrounds in that we’re both designers turned, audience builders, marketers. I don’t know what you want to, whatever you call it now.Jack: [00:12:11]Yeah. Nathan: [00:12:12]Yeah, but I’ve always leaned on constraints. I just think that’s so interesting that you’ve been able to distill it down to something so unique because of the constraint.Right. So many people would be like, let me find 10 different visual ways to explain this concept of build one, sell twice. And you’re like, no, I’m just going to represent it in the exact same type of face and all of that. Because after I do some version of this a hundred times, like then people will immediately recognize it.That’s that’s fascinating. What do you think, going back to the question about, people being unique online, like what are the things that you wish people did more of, or how should creators think about these things differently when they’re and teaching concepts or, any of that to actually be unique rather than, you know, cocking what’s what’s so common. Jack: [00:13:10]Just I’ll preface this or a disclaimer for everything I say is going to be consistent with my experience. But I think the starting out with the service element is a really important piece of it. So being able to transition something that you delivered as a service and, you know, has, you know, it has been implemented with results in a business.Like when I started working on visualized value as a service specifically, I was building pitch decks for like the most boring businesses. You can imagine, like supply chain, , logistics for PL or companies. So I spend hours on the phone trying to understand the supply chain industry and then build these like simplified, , set of visuals that represented what made that company unique, for example.And then when you see that work, you’re like, okay, this is a. This is a thing that I know I would never ever run out of opportunity doing, because there’s an there’s, you know, millions of businesses that can explain what they do as well as they could be. , so knowing that I think gives you a level of conviction where all you’re doing is just becoming a magnet for people who need that.So you don’t need to, you don’t need to keep switching up what you don’t need to keep emulating audience building tactics of other people. You’re, you’re building from the asset as opposed to like being one step removed from that. I think it’s, , and that’s an easier transition to make because you’re, you don’t need the scale initially to live off it.If that makes sense. So the. With an audience of 500 people of, you know, people I went to school with and common connection, or like a mutual connections or one degree separation, I could win like one piece of client work a month by just posting portfolio work and get introductions. And then knowing that that deliverable has value, just build the brand around the, , the philosophy of that service or the philosophy of that, , that thing that you’re building for a client.And then your audience aligns behind that as opposed to aligning behind you for some miscellaneous approach to content. And then you have to reverse engineer a way to monetize that, , relationship or that, that, , That group of people, you don’t even really know what they have in common or what they’re, what they’re interested in.Right? So among the people who follow visualized value, you can kind of, you could think about them in fairly specific ways that people who either want to learn the skill. Like I wish I could communicate concisely with design. So there’s obviously a very specific way that you can help people learn that, or they’re business owners that want to hire you for your services.Or there are people that just want to consume knowledge in a more concise way. But it’s all the foundation of it is the it’s the, the craft, I suppose you call it. And I think it’s hard to. It just, it feels like a different game you’re playing when you’re just constantly trying to create content for content’s sake and then marry that back to something.And what you end up building is like how to build a Twitter audience or, , you know, some generic how to get attention product, but then there’s no underlying like, okay. W why? , so I would, and it’s a brutal process to go through the service business route and you have a design background. So you’ve done that too, but it’s such a solid foundation in my opinion, that you can always, , you can always lean back on.So I think designers have a bias for this, cause this is how we’ve been hired over the years is you build a portfolio, normally cares about your like degree or even the agencies that you’ve worked at, or they want to see is like, what projects have you done? And what, what are you capable of as a designer?Well, how, like, what’s your taste level? Like what tools can you use? And, that I think just creates a bias for publishing proof of work that is it’s like one step removed from like, just purely, the only motivation is to get people to like, and follow a, an account. So it’s a little esoteric, but hopefully that makes sense.Nathan: [00:18:10]Well, I think what I hear in that is this idea of show your work, right. Designers know that inherently. And then other, I think in coming from other industries, you’re like, why don’t people trust me already? Or that kind of thing. Like, look at the credentials that I have and designers are like credentials.Like the only thing that matters is your portfolio. And people are like, yeah, but I went to Yale or something and you’re like, you know, and so designers, no, you have to show the work. You have to show the progress. And I think more industries that adopt that, the more success that they’re going to have Jack: [00:18:42]Yeah. And I think the parallel to that is this like build in public idea. The, but there, there are degrees of building public, right? The, The there’s like the marketing side of it and the product side of it. And some content just feels like all marketing without the, , you know, without this underlying thesis or this, , product that’s being built. So it could be software could be like, , it could be software could be an information product, but there there’s two different layers.The audience building things just become a by-product of marketers marketing, marketing, right. It’s a, it’s a rabbit hole that goes pretty deep.Nathan: [00:19:30]Yes. Yeah, there, there’s a lot of, a lot of that. , we’ll go with rabbit hole instead of circle jerk, but, so you have this phrase, well, I feel like your entire business you’re using design, but is taking con , let’s see like complicated concepts and distilling them down to something really, really concise and specific as you have this phrase, I’m actually intensely jealous of, because I wish I came up with it because it’s trying to explain concepts that I’ve used, like, you know, a thousand words to explain in detail.And that’s build once, sell twice. Can you explain from listening what that means? Jack: [00:20:16]Yeah. So my background is advertising. So I was in the time of materials business for so long someone hires you and at the end of the job, or you make an estimate of how long it’s going to take you. You write an invoice and then you hope that it’s going to take you less time, what you estimated as opposed to a product business, which is way more common in technology, where you build something.And well, you build something digital that has, that runs on code or media and can be served up infinitely at zero cost of replication to you, but can capture value as, you know, as you reach more people. So something like a SAS product or an information product, you build it once you modify it and you can sell it to a thousand, a hundred, a thousand, 10,000, a hundred thousand people.There are incremental costs of, you know, your payment processes and hosting and things of that nature. But the, the bulk of the value is created once. And then just, it becomes a game of. How effective are you at spreading that story and, , reaching people that need the thing that you’ve built. So, yeah, trying to distill that down into a single phrase has been yeah, has been instrumental in being able to do the thing too.So, that’s I think, like a little layered lesson that I’ve learned in, , building something, building a product is obviously a huge part of that equation, but also finding a very concise way to talk about that product is, is the other half of that equation. So, you know, write something once and then publish it a thousand times is the same idea.And you can use that as a propellant for the thing that you’ve built. , and now we’re in this era of the like full stack creator where you can. Build the thing market, the thing like perform customer service for the thing from one laptop from anywhere.Nathan: [00:22:30]Yeah, it’s, it’s probably the single most important concept for someone on the internet to understand. , cause like in the same way that if a hundred people sign up for ConvertKit today or a thousand people sign up, it doesn’t matter. Like we, we built the thing. We can sell it as many times as we want within, you know, if like a million people signed up today, we’d have a few issues, you know, but like within a reasonable distribution, same thing for, you know, one of your courses, like one person, 50 people, a thousand people, it doesn’t really matter because…Jack: [00:23:06]Marginal. Nathan: [00:23:07]Yeah, exactly.Which is both amazing and can be painful because you, it often like a part that people miss is that the build once, when you are building it for an eye to sell it, You know, twice or a thousand times or more is actually more work. Like it’s a lot more work to build rather than if I’m just like, oh Jack, you’re my client.I’m going to build this one’s for you. Like I can get away with a lot of things, , and then get away with is even the wrong term. Right. I can simplify it. I can just, I’m just building it for you. know who you are. I know who my client is, but when I’m building it to sell, , you know, an infinite number of times, then I have an infinite number of circumstances, , that it could be perceived in.So yeah. Maybe talk about the difference between building something wants to be sold once versus building it to be sold many times.Jack: [00:24:04]Yeah, I think you’re right in that you have to anticipate a lot more. So if, if the thing you build doesn’t work without you, then it doesn’t work right. In a one-on-one relationship with a client, you can get on the phone and you could sort of call an audible. Or if you, if you, you know, you can wait until the last minute to fulfill this piece of the thing.And that that transaction is totally different, right? It’s the pitch, the sale. And then the work starts versus you build the thing. And then once, like the sale is basically the last part of the process, as opposed as opposed to the first part of the process. So, , well I think going through that process does though is really helps you identify it helps you build the story to tell people what the thing is.And that’s, that was the really frustrating thing for me about an agency business was like, Well, are we, what do we do? Like we’re a creative agency. We can solve any problem creatively, right? If you’re a car company, if you’re a, like a prenatal vitamin companies and other old client of mine, like finance, anything fashion, and you end up saying like, yeah, we can help you with your mock that we can write emails.We can build websites. We can do, , we could do all these different things. And until we, we are, I think a citizen of the internet, which I wasn’t until two or three years ago, you really, it’s very difficult to grasp the opportunity, unity that exists in a, in a very narrow wedge, right? You, if you’re, if you’re great at one very specific thing and you find a way to get that message out to the world on the internet, it’s very unlikely that you’ll run out of options versus you have this really generic message.You don’t get, you also don’t get the compounding benefit of working on the same problem over and over again. So I’ve friends who run agencies that are incredibly talented, but instead of building products, they just hop from job to job. And there’s no like there’s no, they’re not earning equity in, in a specialty or against a niche.For example, like ConvertKit is, , is a good example of some talented agencies would spec would build like 80% of ConvertKit for example, and then move on to another job. And to me that’s just bananas, right? They’ve just abandoned all of this equity and energy that they’ve invested. And now they’ll go and work on like a no real estate platform or something else.Not to say that the job is done when they’re finished as an agency is only just beginning, but it say. There are obviously pros to that business where you don’t have all your eggs in one basket. And I think that’s what keeps a lot of people in that world, because if it feels less risky to, , to sort of diversify, but in the age of the internet, that diversification is oftentimes unnecessary, but also, , and just cost you a lot of opportunity in the long run, not making a decision to, to own one thing or get really great at one thing.Nathan: [00:27:26]Yeah, that makes a lot of sense because as. People will create this work that they just throw away. And they think about like, oh, I don’t want to be pigeonholed. I don’t want to be the agency that only works with real estate clients, or I don’t want you know, put in this box, like I’m an artist, you know, or whatever I think.And what that means is that you are creating from scratch every single time. And then maybe eventually it’ll loop around. So you have a similar, you know, you have that second real estate client or, you know, something like that. And you’re like, oh, I get to borrow some learnings. And really when we choose this niche and focus in, then you’re, you’re borrowing those learnings every single time.And it really, I mean, that’s where things start to compound. ,Jack: [00:28:10]Yeah.Nathan: [00:28:11]Without that, you don’t have anything compounding.Jack: [00:28:14]Yeah. And it’s hard. Like, I think creative people, you said it, it’s like, I don’t want to pigeon hole myself. I don’t want to, I don’t wanna be working on the same thing every day. And I used to, I used to, they used to be one of my lines I would use in interviews. It’s like, why do I like, working at agencies?Cause you have a different challenge, a different problem, a different industry every day. But at a certain point it’s like, I’m not really like hyper competent at anything across all this stuff. And that’s, you know, that was getting frustrating at a certain point. And then I. There’s one realization I had someone told me this years ago was like identifying the feeling that you enjoy versus the, , versus like the tangible application of your skills.So it’s a slight shift in, , slight shift in perspective in that, , visualized value is just this vehicle for me to become a better designer and, and help me, , help me better translate difficult concepts into visuals and all of the constraints that I’ve placed on. It actually helped me get to that feeling faster.And that’s a hard thing to identify, but once you get to that, like then you start to take advantage of the compounding stuff. Cause you can solve a lot of different problems if you, you know, build and convert it. For example, like. No two days are the same. I imagine because you have this compounding, asset to work on, so you can go in and tweak something.And then that thing delivers a benefit months, years into the future. You don’t need to go back and visit until it breaks or until there’s a better way to do it. , and it’s easy to confuse. It’s easy to confuse working on one thing with not having new problems to solve. I think the opposite is actually true because you’re solving problems in code and making things that fix the problem that you can move on from.You’re constantly getting exposure to, , new types of problems and new ways to solve them. That’s really the, yeah. The what focus affords you in the long run is, and, and obviously the build once sell twice mentality and focus is, always exposing you to new problems. And, letting you build equity, as opposed to just trading your time constantly to work on different problems.Nathan: [00:30:49]Yeah, yeah, absolutely. I want to dive into your business a little bit. You’re very transparent with numbers. , and I want to like, kind of understand the flywheel of, you know, Jack Butcher. Maybe share some numbers initially and, , you know, on, , social following and, and email list and then getting into revenue.And then I’d love to hear kind of that arc of how, how each thing feeds into the next. Jack: [00:31:16]So social is at, I would say around visualized value specifically is about 450,000 followers, Instagram and Twitter. My personal Twitter is about a hundred and twenty-five thousand and email is actually one of, , Smallest audiences, probably about 20,000 email subscribers. , and this is a real focus of this year is, is dialing in email.I could go into it, but I’ve got Twitter accounts banned a few months ago, but, , the flywheel, like the, on the product side, we have, , education products, how to visualize value and build one, sell twice, , some smaller products. We have a planner, , some art, some merge, and don’t spend any money on advertising.I would say 80 to 90% of sales come through organic social. So the, a really simple system like that, the art gets posted to Instagram and Twitter. And the bio link in both of those is the store people. You know, if they discover it for the first time they click on the store. Or scroll through Twitter, , wrote, , worked with a lot of people.Who’ve been through the courses to write case studies and those do a great job of educating people who come in organically on, you know, the types of people that have leveraged the content in the courses to build things so that those case studies on the store get a good amount of traffic. And that feeds into products and then run occasional organic promotions, which are responsible for decent spikes in revenue.So that will be milestones. Like, you know, , the account has reached X Dunbar, followers or holidays. , there’s, there’s definitely an organic, , there’s an organic flywheel where the floor increases slowly with time, but the real big spikes in revenue still do because we’re not doing paid advertising do rely on these times.Promotions and incentives and getting people to act in a very noisy, crazy world. , and, and paid advertising is something that so many of my friends have, , tried to encourage me to do, but there’s just some resistance there for whatever reason, , because when we haven’t needed it so far, and two, it’s just such a interrupting thing that it feels like it might not be consistent with the way, , the brand is working now, but it’s all about execution.So not writing anything off. , but email is a big focus for this year and SEO, , like just, , the things that don’t rely on a stroke of creativity happening on a daily basis. I definitely want to keep that, that as a part of the business, but building up the floor as well. So where, , recent convert kit, , Customers on building out a bunch of different experiments on that.So excited to get that role in this year.Nathan: [00:34:34]That’d be fun to dig in on one thing just as I was going through, , or like revisiting more of your Twitter feed that stood out to me and it goes back to the constraints. It’s interesting. Right? You talked about the constraint and the visual style means that no matter what I do, someone will recognize this, you like, oh, this is visualize value.This is Jack, you know? And just because we have like the slightly pixelated, you know, like that exact font that look on a black background, And so when I come across it, you know, and I come across all your stuff cause I follow you, you know? Right. But you see it in a thread and you click into it. Cause you know, it’s going to distill some great concept down, but use the same style for like your Memorial day sale, which is, you know, really all you’re saying in this graphic is like, Hey, there’s a bigger discount on Friday.The discount decreases over time, but I’m trained. And everyone else is of like, oh, this is one I know exactly who’s running the sale. You And, and to I’m expecting that there’s value in the graphic that I click on. And in this case there is, it’s just that you have to like, it’s another step away. And so it’s fascinating.I believe that your ad for the target market works significantly better because of the constraints that you put on it. , because I’m trained to opt into that is that side of it intentional as well.Jack: [00:35:59]Yeah, I think one of the fortunate things about it is the transparency in the tactics used to grow the business.Like demonstrate the value proposition of the product itself, if that makes sense. So there is this dub, this layer of the more effective mock organicmarketing techniques that I can test and prove the, the better the content in the products becomes.So you have this, , which would not be the same if you’re selling like physical merchandise, for example, right. You can run really clever ads, but those ad mechanics, aren’t part of the product that someone is buying. So you gotta have this double layer of proof where I’m trying to, , test and document things that work for growing internet businesses.And in that practice, , you kind of get proof for the fact that these things are working by making your purchase. It’s kind of a. , Metta idea, but it’s been a, that’s been a really helpful part of the story is just being totally transparent about it and, yeah, like willing to fail in public. So you don’t have to on some of this stuff too.Nathan: [00:37:24]Right. There’s an interesting point about audience selection that is in there. And I think I first realized this when maybe paying attention to, , DHH and Jason from base camp. , it was sort of the thing of like, wait, they have a product and the more they talk about how they build the product. The more, it drives sales for that.And on one hand, you’re like, oh, that works for everyone. But if you break it down, like it actually doesn’t work for everyone. Right. If I run a pool cleaning business where you know, that is my agency, that is my service. And I’m out here talking about, here’s how I built that business. Those are two very different audiences.You know, that the other audience is people who want to start pool cleaning businesses, or maybe those who want to clean their own pool. I guess you can have that, but then you need to go off in the info product world, need to do all this other thing. And so it’s, it’s very different. And the thing that I love about my business and you have the same advantage is I can talk about how I run the business and the people who care about that are also the people who would buy products and be customers of the business.And so if you want to like build for longevity and you enjoy building in public, then it’s one of those things to make sure that there’s significant overlap between those two groups. Because I think we assume that most businesses have that. And the reality is. I think only like 10 or 20% of businesses actually have that audience product. Jack: [00:38:53]Yeah, yeah, spot on. And it would end up in you building two different products, right? You have the productization of the service as a secondary business. I read this great tweet yesterday. So the dog that has two owners dies of starvation. So the idea that that’s like basically building two businesses, it might not feel like it, but it is.And I think it’s very easy to get distracted by things like that, to where it feels like, oh, it’s just another revenue stream. Like none of it’s a totally different focus and a completely different empathy you have to have for very different type of person. Right.Nathan: [00:39:32]Well, so diving in on this, for an example that came to mind would be Nick Huber, who has put her handle his sweaty up his business. Like his real core business is buying, , self storage facilities and, you know, building those out, getting the recurring revenue from it and all that he has just happened to, as you said earlier, become a citizen of the internet and like go all in on that world, build a following of over a hundred thousand on Twitter.The more he talks about his business of how he built it. Not no one cares, no one who’s like buying self storage is like, oh, let me make sure that I get a NICU or like a storage box. Jack: [00:40:16]Right? Right. Nathan: [00:40:18]So he doesn’t have any overlap there. And on one hand, , you know, he’s able to drive new revenue streams. He’s able to meet lots of people.You know, he came out with a course and. I think he shared that publicly, that it made, you know, hundreds of thousands of dollars. , and that’s incredible. That’s two separate businesses. The interesting case is that it almost never hurts you to build that audience and to share because he has this sort of overlap of another element to the self-storage business is that he needs investors.He needs coming in and saying, , you know, like being the limited partners and putting up millions of dollars for that. And so he has two different customers already, and, and Twitter is very helpful for getting that second customer, not the buyer of the self storage facility or the renter, but the limited partner who’s going to put in money.And so you get this whole range of things. And so I guess I say all that to explain that it’s not one or the other, it’s not binary, it’s, there’s a whole fluid aspect to it.Jack: [00:41:25]I think that’s a great example where you have a, you have overlapping utility, like your ability to explain your depth of expertise. As an operator does perform a core function in your brick and mortar business too. Right? If he never sold a course, he’s still probably attracted multiple seven figures of capital into his investments by.Demonstrating that he knows what he’s doing or understands the mechanics of the industry. And then, because he found success doing that. It’s like, well, there’s also people who want to learn from me too. , I think there’s an interesting, I think there’s an interesting insight in that that is, that is maybe only uncovered in hindsight, but these things that have some ulterior motivation tend to be like the examples of people that I know were doing something either for themselves or to perform a different function.It wasn’t purely a, like, I want to, people want to use the NICU. For example, you didn’t stop that because you wanted to sell a course on how to build self storage facilities. It was likely the investor motivation that got him started. So this business is running. Need to like demonstrate my expertise online.My original publishing visualized value graphics was just to find service client service, business clients. So is it just a lead magnet? And it got big enough that it brought in more service opportunity that I could handle. So that presents a product opportunity to scale the, , first scale, the design element of the business by teaching people design as opposed to selling hours of your time to work on design.So that’s like a small nuance. I think that goes back to what we’re talking at the beginning of the conversation where the word selfish is, you know, you can interpret it however you like, but if there is no like drive to produce this thing for some selfish motivation more often than not, like just sort of get lost in the.In the, in the weeds a little bit, or you’re, you know, you’re just pursuing a metric that doesn’t have a, , a direct relationship to the success of a business. You already own, like, I could publish a hundred visualized value graphics. And if I got one message from somebody that said, can I hire you for consulting?That would have been a success as opposed to not having a consulting business publishing a hundred pieces of content growing an audience of a thousand people. And then what? So I think the service business, like a grind, and in the case of the Huber example, you’ve built a different type of business. And then the internet is, , you know, just adds additional leverage or opportunities to that business.And then 3, 6, 9 months down the road, you look at what you’ve built and you’re like, ah, okay, light bulb goes off. Here’s another opportunity to serve the people that are already subscribed to your stuff.Nathan: [00:44:40]Yeah, well, yeah. And it gives you that. Like success is going to take so long to actually achieve, you know, , you’re going to have to have the hundredth graphic or more before people start like, oh, oh, I see this was all the same person I saw pop up, you know, like I get it now. And if you don’t have that, the value coming back to you in some way, then you’re going to give up that like, you know, graphic 14 or something like like, oh, I did it for the altruistic, like just to create art, you know? And, and, and that will die out. You actually need things, you know, you need value coming back either into your pocket or to your ego or something else.Jack: [00:45:23]Some feedback loop has to exist for sure. Nathan: [00:45:26]So one of those feedback loops like this is ultimately a business show. , so one of those feedback loops is money. And so I’m curious, you know, courses are the primary thing. Are you up for sharing some of the numbers behind, you know, like what each of the courses earn. Each year at a high level,Jack: [00:45:44]Yeah, we did a 1.1 million last year. , and I say we, me and my wife, , there’s nobody else involved. , the breakdown of that, I think it’s about 60, 40 build one sell twice and how to visualize value. , this year it’s interesting in the last year was kind of a crazy time for online education and there’s so much concentrated attention and this really huge shift in remote work.So this year, we’re still doing, we’re still hitting good numbers organically. I’m running far less. , intensity of promotion and the products of, you know, they’ve been, they’ve been in the X-date guys for a little while now, so just have to be more creative about, , building up that floor and bringing new people into the audience.So we’ll be on track to surpass what we did last year so far, but there’s definitely, , there’s definitely a requirement to innovate on the marketing and the content side and, , you know, how to continue to build the audience and deliver value and also how to motivate yourself. Right. I feel like I’ve covered these topics in such depth and detail at this point, which may not be true to everybody reading.So you can definitely repeat the, we can repeat the playbook and use the things that are working, but there’s also this element of keeping yourself entertained and interested. And, , when you. I think you can feel the energy of somebody promoting something, , genuinely based on like how they talk about it and like, , going through those feedback loops in real time as the product launch, as a product launches definitely creates a different type of energy than sustaining it for years and years and years.So, where, yeah, it will be on track to, and I like to say double revenue this year. We’ll see. Nathan: [00:47:50]The point that you’re making about the energy and it being something new, right. As we create things, we’re looking for something new, it can often get us into trouble because you could have something that’s working and you’re like, oh, that’s amazing. That’s working now. Let’s do something new. And like this stops working for some reason.And you’re digging in. You’re like, why is that not working anymore? And I’m like, oh, cause I have worked on it in three months. You know, I haven’t put effort into it, but at the same time, it totally comes through when we’re following a personality driven business. If that person’s heart isn’t in it. Like, you know, we followed them along when they were super passionate about it.They were building in public, they were sharing like, oh, here’s how course is coming together. Here’s everything. There’s that excitement there. That’s an interesting challenge of like, what does it look like in year two or year five, , where it’s like, I still care about this, but I’m just not passionate about it anymore.Do you have, , either examples of people that you look to who have systematized that and solve that problem or your own things that you’re thinking about?Jack: [00:48:54]Yeah, David Perell is a good friend of mine and Write of Passage, is a great product. And I think it is probably, it probably does have something to do with the level of specificity. and , And , what’s the word I’m looking for? Not the timeliness, but the like writing. So of the two visualized value products.Let me backtrack a little while the build one sell twice was really popular last year, but I think out of visualize value is going to be the longer term, , the longer term, , asset or that asset is going to have the most value over the longer term, because as behavior starts to change and people stopped, like this starts to become more natural, right?And it, that business is just becoming obvious at a certain point, we still have a way to go, but, , last year culture shifted so aggressively that it feels almost try at a certain point to keep explaining these, these concepts that you know, everybody, at least in the circles that I occupied on Twitter was talking about this nonstop for 12 months.And as a world. So it comes back to life a little bit. It’s, , you know, people have other things to do and different things to talk about and like interests that they weren’t able to, weren’t able to pursue for a year, maybe. , so yeah, I think something that is more closely aligned with, , the craft, maybe that design for me is, is that, so I’m never going to stop producing on the visual side.And that pursuit I think is, , is eventually going to overtake that moment in time where we were talking about internet leverage, if that makes sense like that, that’s all still part of the conversation, but the visualized value brand is more about design than it is about like building replicable internet products.That was one of those, like. It was actually an audience inspired idea to build, build one, sell twice based on out of visualized value, being a product. So my transition from service provider to leveraged information, product architect was something that other people wanted to understand that weren’t designers.So doctors, lawyers, , video editors, whoever, how do you take this thing that you’re doing spending a ton of time on and earning zero equity in and build products? , I think it’s going to be valuable for a long time, but it does. , like I personally have more, , more energy for design over the long run than that.If that makes sense. Like once you’ve explained that a thousand times that that content exists go and find it. Whereas design is this thing where you could spend 500 years. You know, perfecting it and iterating on it and you’ll, , you’ll see like tangible, , results show up in the craft as, as you go. Nathan: [00:52:09]I think for me, like I always, I guess as my role has changed, you know, going from an individual like designer, doing design work at an agency for a startup freelancing, you know, and then working through to selling products and all of that. And then up to, you know, like leading a 65 person company, the now the skill that matters most is the ability to succinctly communicate.Complex concepts and do that repeatedly. And so that makes sense to me that you know how to visualize value as a product is one of those things that can apply even further, whereas builds won’t sell twice as amazing as it is, is like a deep dive on a single concept versus how to take it across everything.Jack: [00:52:59]Yeah. And I th I think for a different person that like, maybe the opposite would be true, but based on my personal like skills and, , interests, that’s where your instinct has to kind of kick in and be like, okay, what are we optimizing for over the long-term here? And, I think it’s that. And, and what is our actual moat?You know, what, what are we, what do we do better than anyone? Or what can we do better than anyone I’ve given enough time and energy? And I think design is, is more that answer than, , all of the different ways you can spin an education product around building online businesses. Cause that, that, again goes back to our earlier point in the conversation, which is like a lot of that noise has just reached deafening pitch at this point.And, competing in that world is just not something I’m, I’m very interested in quite honestly.Nathan: [00:53:59]How do you think about new courses versus continuing to grow? like the, the two that you have, you know, or like, I sometimes explain this as like strip mall versus skyscraper. You get, , more retail space, right. In each case we have, we have more retail space that we can rent out, you know, any of that, but like, are you building a whole bunch of things and doing urban sprawl or are we taking one thing and like scaling it 50 stories tall. Jack: [00:54:29]Yeah. So I, yeah, maybe, maybe, I’ll, maybe some more quote me on this incorrectly in years to come by. I feel like I’ve put almost everything I know in those two products, I could took 10 years of work to get the experience that went into those products. So it feels like you, you can con you know, what I learned in the last six months can go into those and iterate on thoseBut is there going to be some highly specific thing that I stumble across that I think is worthy of designing a new curriculum around? Probably not. And that’s another reason why the that’s another reason why the marketers doing marketing feedback loop is like ends up in you sort of producing these products that dilute each other in some cases.So if you have like 50 skews as an education business, that to me is like that kind of dilutes my objective, which is help people com become better communicators do build once or twice and how to visualize value need to exist separately. Yes, I think so. , but is there like nothing pops in my mind right now or I think, oh, I could like design another curriculum.Nathan: [00:55:50]Right. Jack: [00:55:51]This huge set of experiences that I have, that I haven’t already covered that, that right now that doesn’t exist.Nathan: [00:55:56]Yeah, that makes sense. And so not forcing it because I think a lot of people would look to maybe the interest waning in a, in a project or like that, that initial motivation, or they would say something like, oh, I want to double revenue next year. So let me double the skew count. and that, that results in a whole host of problems.Jack: [00:56:16]Yeah. And it’s a, it’s a much, like exactly. It’s like the short term solution to a long-term problem and diluting the work you’ve done to the point where someone visits your website. It’s like, well, which one of these? It’s like, it’s very simple right now. I mean, it’s like, do you want to learn design or you want to learn like how to build a leveraged it net business?Or do you want to learn both? That was your options versus like the. And, and the curriculums of both of those things are way more principal driven than they are tactical. So that’s another thing that isn’t, there’s no need to go back and update them every time a product ships, a, you know, , a new feature, because it’s not talking about like, here’s how to build a website or here’s how to like, run this line of code it’s is how you should think about this problem.Or here’s like a, you know, a mental reframe on an offline business versus an online business that this insight may not come to fruition in the next five hours for you. But it’s going to rewire the way you think about this to the point where, you know, you will have chosen different opportunities in 10 years time.So that’s also a, a different way to operate or a different way to think about these things. And when you’re competing against like get 9000% ROI today, Then, , you know, I feel like the last three months on the internet has been a very strange time for education products in particular, because it’s like, oh, well, I actually have to like put the work in and the time.And you know, there’s not necessarily going to be an infinite ROI on this thing on day one. That’s, , you’re competing against a lot of craziness right now.Nathan: [00:58:06]Yeah. Yeah. That makes sense. , I’m curious who you look to for inspiration on two sides. One would be, you know, on the creative side, if anyone comes to mind and then the other would be like on the business side, if you think about the business of visualize value in 2, 3, 5 years, like, who or which businesses is something that is like inspiring and saying, okay, if I can create my version of that.Jack: [00:58:32]There are definitely. Most of the businesses that inspire me, like nobody’s ever heard of. So like the, actually went to coffee this morning with a guy who runs a, a plugin for, Poshmark. It’s like a, this, this, this tool that, , helps Poshmark buyers make more money, essentially. It has all these different features and it runs purely on Google ads, SEO, and he’s never had a customer support phone call in his life at rice, like writes emails back and forth, but has a, like spends eight hours a day with his family has built this product where he just goes in and, you know, thousands in every couple features a week.And, yeah, it just has a ton of time to himself. The, I get, I get in the trap sometimes and be like, oh, what if you built a massive, like massive media business or a massive, , software company? Maybe that maybe there’s time for that. We just had a baby three months ago. So, , right now it’s like time optimization over everything and, , yeah, there’s certainly people I admire on the think in front vowel was massively instrumental in, , like shifting me in a direction of technology.Brian Norgard, great guy product. David, oh, I mentioned Anthony Pompliano like, there’s just like killer content produces like that. Guy’s an absolute machine and , yeah, that’s, that’s so many, that’s so many, , so many brilliant people. I think the amazing thing about the time we live in now is, you can just build such a unique business.And, I’ve always found that I try to emulate someone else’s model. That’s got me in trouble. So I’ve S I’ve seen like somebody, somebody, you know, being successful with some specific mechanic, like I can emulate that. And then it’s like, no, wait a minute. There’s a reason I didn’t arrive at that because it doesn’t fit with like, well, I’m interested in, what I’m good at.So that like introspection of figuring out like, , what gives you energy and what you can sustain is far more, , at least for me has been far more, , instrumental than saying I can, I can emulate that tactic and see how it works. , yeah, the, the idea that visualize value graphics, a sort of disk, like a.When inspiration strikes, you can make one and post it. And it leads to business results as opposed to having a structure, like a cohort based thing and show up five nights a week to teach something. For example, because there is plenty of monetization opportunities that exist that just don’t fit the way I, , I like working.Nathan: [01:01:42]Yeah. Yeah, that makes a lot of sense. , I was going to ask, is there an example that comes to mind of where you borrowed someone else’s or went to borrow someone else’s strategy or mechanic and realized later this doesn’t fit at all? Jack: [01:01:57]Yeah. So the cohort-based thing is, is the perfect example. So I’m an investor in Maven, do you know Maven? And I started working with the founding team there. It’s like the initial thing was like, I’m going to do a 12 week cohort-based course. And they have an incredibly talented team that work on the curriculum and help you structure everything.It’s like, how do you engage the audience and how do you do this? And how do you, and as I was going through that process, I’m just like, this is not me. Like, I’m not like some people are great at running like 15 consecutive sessions or two, twice a week for 12 weeks. I couldn’t do it. And I realized like three weeks into like building these things that it just wasn’t consistent with what I’m about.And then recently I just started talking to those guys again about running a course, like, oh, I’ll do a three day intensive bootcamp where I can get X, Y, and Z across that some pre-recorded materials and like I can deliver well, I know I’m good at, in, within those constraints, as opposed to adapting to this, to this format that was prescribed out of the gate.Yeah, I’m sure you could make it work, but it’s like, if it feels like it’s. No 10 X the amount of energy required to do something that other people do really, really naturally. That to me just feels like a, a waste of time if you have other options available, at least.Nathan: [01:03:24]Yeah. Yeah, that’s good. And you see these trends, you know, of like cohort-based courses or anything else come and, and then settled into like the natural, like audiences or communities that they’re a really good fit for. as they’re just being careful just because like, it’s sort of like, you know, there’s sort of this wave of like Groupon and living social and all of that in the or you’d end up with, like fab.com.And I’m trying to remember like other ones of that time period where, or like when everyone was launching a mattress company, as an either…Jack: [01:04:02]Example. Yeah. Nathan: [01:04:03]And there’s like a huge need for mattress companies. Right. And it provides a real like, and we had this stair step in innovation. We can, we can ship them directly to people’s houses, all of this, but that doesn’t mean that everyone needs to start a mattress company. You know, like only the people. Jack: [01:04:18]For everyone. Yeah.Nathan: [01:04:20]The people who deeply care about that And that is a good fit for them.Jack: [01:04:23]Right.Nathan: [01:04:24]Go that direction. Jack: [01:04:25]Yeah. I think some people, like there are a few people I’ve met that just like ruthless execute is, and that goes back to the like, figuring out what your, like, it might not be the product that you’re passionate about, but it might be like building a like system of like distribution or logistics and matches has happened to be a great fit for that.It’s like, it really is a really was tough for me to like figure out what, what feedback loop I could do every day without getting frustrated. And it ultimately comes down to like that very specific type of design work. And then. The business model has to fit that as opposed to the other way around, if you want to stay lean and small and all of these, all of these, you know, internet, citizen, buzzwords that we throw around these days,Nathan: [01:05:20]Yes, we have lots of them. Well, if people want to follow more of your, you know, your buzzwords and now I’m just kidding. , but everything that you do online, where’s the best place to follow you.Jack: [01:05:33]Twitter is the best. So, @jackbutcher and @visualizevalue, you’ll be able to find everything else from those feeds. Nathan: [01:05:41]Good. Well, thanks for taking the time to talk to me and, it’s fun. I love following your stuff and I’m excited to see what the next year and many years beyond that hold for you.Jack: [01:05:51]Likewise, mate. Yeah. Thank you for having me on.

Alex Lieberman is the co-founder and chairman of Morning Brew. Morning Brew is a media company bringing informative and digestible business news to your inbox every morning. They educate nearly 3,000,000 daily readers on the latest news from Wall Street to Silicon Valley.Alex also hosts The Founder’s Journal Podcast where he gives listeners a “backstage pass” into building Morning Brew, and in turn, helps them build a better business or career.Morning Brew is considered to be the largest email newsletter on the web. Business Insider recently acquired a major stake in Morning Brew at a rumored valuation of over 75 million dollars. In this episode, you’ll learn: The foundations for building a great media brand What methods and metrics work best for rapid subscriber growth How to optimize a referral program to gain explosive growth How to be the leader your employees need as you scale Links & Resources Business Insider Kara Goldin’s LinkedIn page Hint Water Pat Flynn Pat Flynn: Why I Switched from AWeber to Infusionsoft to ConvertKit KickoffLabs Viral Loops Robinhood Tim Ferriss Harry’s Razors Lenny Rachitsky Packy McCormick Guest’s Links Alex’s LinkedIn page Morning Brew Founder’s Journal podcast Morning Brew Accelerator (MB/A) Alex’s Twitter: @businessbarista Episode TranscriptAlex: [00:00:00]That’s the beautiful thing about just business in general, this diversity of what brings people joy. People who love building process and planning who have a foundation and building on top of that foundation. You have people who have zero foundation. They want to prove to the world and prove to themselves that the crazy thing that’s been in their head that they think is valuable, there’s no proof of yet, that the actually people will love it.Nathan: [00:00:30]In today’s episode, I talked to Alex Lieberman, who is the co-founder, and now chairman—formerly CEO—and now chairman of Morning Brew. They grew the newsletter to over 3 million subscribers, which is insane. Making it the largest email newsletter on the web. So if we’re talking about newsletters on this podcast who better to talk to than Alex.We get into why he transitioned from CEO to chairman. We talk about the exit: they sold a majority of the company to Business Insider rumored at over a $75 million valuation, which is really, really impressive. One of the things we talk about the channels that drove growth, their affiliate program, the referral program that so many people talk about and reference, what works, what doesn’t.We get his take on sponsorships versus paid content, details on the type of ads that they used in their paid acquisition when they were growing Morning Brew, so much.Anyway, there’s a lot of good stuff. I’ll get out of the way. Let’s dive in.Alex, thanks for joining me.Alex: [00:01:32]Thanks so much for having me, pumped to do this.Nathan: [00:01:34]All right. So I want to start with, your role has shifted. You just moved from CEO of Morning Brew to chairman. And tell me a little bit about that.What, what instigated it. What made it time for that move? I know a lot of people who have run companies for years consider a move like that.Alex: [00:01:52]There’s many months in the making. and I think in a lot of ways, the last year has kind of been like a unspoken transition, based on just the things that I was spending my time on and the things my co-founder Austin was spending his time on. You know, I think the, the way that I think about it is I loved—I’ve loved every part of Morning Brew, but like the things that have really given me energy is when I am building things from scratch, I love building things from scratch.And that’s what I was able to do in, in the early days of the Brew, you know, our original newsletter, our B2B newsletters, our podcasts, like really creating the foundation for something that could obviously become a large media brand. As we’ve scaled, obviously like, you know, you’ve, I’m sure experienced this in your role, the roles of a CEO change 50 different times.And so the way, you know, the way I think about it is the first role that I had at Morning Brew was every role Austin. And I had every role. I always tended to lean more towards sales, marketing, and content, like more the creative and people facing side of the business. Austin always, spend more time on growth product, and like the finance, the finances of the business.And so I wore many different hats and I loved doing those things. And then as we started to grow, as we got the flywheel going of creating great newsletter content, attracting audience and monetizing our audience through advertising. My role shifted. And I went from a hundred percent doing to what I would say is like 50% doing, and 50% managing.And I really enjoyed managing, like I loved, I loved coaching people, supporting people, but what I also learned pretty early on in Morning Brew is that managing there, there were aspects of managing that I loved, and there are many aspects of managing that I didn’t love. The way I think about managing is I think there’s two aspects to managing there’s call it like leadership and there’s operational management, operational management, really being about.Like goal setting, metric checking, and making sure that you’re holding someone accountable to continuing to do the job they’re supposed to do really important job for a manager. Then on the flip side, I would say the leadership side of managing is kind of the empathetic management part, which is how do you support someone in their career growth?How do you talk to someone about the things that are impacting them in their job performance, whether it’s things within their career or things in their personal life that are coming into their career, because that inevitably obviously happens as well. And what I realized is I really loved the second thing.I didn’t necessarily really loved the first thing. The reason I bring that up is because as we’ve scaled as Morning Brew, let’s say got to 50 people and. And at 50 people, we really, that was the point in time when we had to go from being reactive to proactive, where we no longer had one product we had at that point in time, we had two or three products.We were truly talking about this transition from newsletter company to media brand. And that was the point in time where it became very clear that proactive scaling process, senior leadership, what was, what was needed to build a brand, to transition from newsletter company to brand. And the reason I bring up what I was saying before about like operational management is because.In many ways. That is what Austin, my co-founder has always loved. And it, and as COO of the business, that is what he, oh, he did always did. And I think as we made that transition to needing more process going from let’s call it a one to two layer business to a two or three layer business. as we needed to set one-year three-year five-year plans, as we needed to hire senior leaders, I think it, it was that operational management muscle that became far more of the time necessary to run the business.And so over the last year, what I found myself gravitating towards is this stuff that I always gravitated towards, which is like, Building new stuff. it was more of like the culture and leadership side of management and it was being like a creator myself. Right. And, and so for example, like building new stuff, what does that look like?Well, most recently Morning Brew launched our paid product. It’s a, it’s called MBA. It’s an accelerator for business professionals. Like that is something that I spent a lot of my time on. And so all of that to say, like, this was a transition that was really difficult for me from, I think, an ego perspective.And I think this speaks to how even now, like a lot of the work I’m doing is reframing why I love building and really reframing it of like, you know, we talk about how it’s really important to build for the sake of like loving what you’re doing, like loving the building you’re doing and loving that you’re helping to serve people.But I think there’s always an aspect of people that’s. Ego-driven that’s driven by like what the outside, how the outside world responds to the things that you’re doing. And I think in a lot of ways, what, what this transition has allowed me to realize is that for the longest time I was spending time building for other people, and I’m making this transition to really getting to a place where I’m grounded and whatever.However, I spend my time moving forward, it’s doing it for myself, for what gives me energy. It gives me purpose and what gives me fulfillment. And so most recently with this transition, It was really hard because my ego was still latching on to, the role because the role had been my identity for the last six years.Morning Brew’s been a hundred percent of my identity since I graduated from college. And so to me, it was a really anxiety provoking thing to think about once you strip me of that title, once you strip me of as close of connectivity with the company who am I, and I think it’s a, it’s a really valuable thing for me to realize the really valuable thing for me to work through.But from a practical standpoint, I think it made all the sense in the world for this transition to happen. Because today, at this point in time, maybe I’ll like the things I’m talking about, like operational management, planning, process, all these things, maybe I’ll like that later in life or in a few years more.But at this point in time, I don’t love those things. if I don’t love those things, I’m not going to be the best at those things. Those are the things that my co-founder Austin does love, and he’s really good at. And I want to see the company succeed. I’m incentivized to see the company succeed. So why wouldn’t I put the person who is, who loves and is best at those things in the position to do those things.Nathan: [00:09:19]Yeah, that, that makes a lot of sense. There’s things that you said in there that really resonated with me. One is focusing on the early days of like, are you likely to start things? I like to start things. I don’t like to start things from scratch, you know? And so the idea of now starting something new and having an audience and having like the leverage that you have now, like, it’s like, oh, that’s compelling, you know, doing ConvertKit over again from scratch and doing Morning Brew over again.Like that. To me, there’s nothing compelling about it. Cause I’m like, oh God, so hard and painful, but I totally understand it. We were like, wait, if I, as who I am today with the networking connections and audience, everything that I have, oh, we want to spin up a new paid product. Yes. I’ll dive all the way in and great that.Alex: [00:10:03]Yeah, totally. And I think that’s like, that’s kind of the beautiful thing about just business in general is you do have like this diversity of what brings people joy, right? Like you have, you have people who loves, who love building process and planning. You love having people who, who have a foundation and building on top of that foundation. You, you, you have people who have zero foundation. They want to just prove to the world and prove to themselves that the crazy thing that’s been in their head that they think is valuable, but they there’s no proof of yet that there’s actually like people will love it. And so the fact that there’s all these different brains is an amazing thing.Nathan: [00:10:44]What do you spend your time on now? You know, you’re talking about we’re before we hit record, you’re talking about like open space and like, try not to make too many commitments for all the things.Alex: [00:10:55]The, the stuff that I’m spending my time on now, so how I describe it as for Morning Brew,I’m spending my time on basically three things. It is helping to ensure that the culture of the business scales as the company scales, you know, Morning Brew by the end of this year will be probably around 140 people.By the end of next year, let’s call it 200. Plus what’s been really special about this business is our culture. having people who are. Hardworking purposeful empathetic, who have a little bit of a chip on their shoulder to build something great. And the question is, is as you scale, how do you maintain that?Right? It’s like every scaling companies challenge, I get excited by that challenge. So, that’s one of the ways that I’m helping, the business still is to work with, Austin and with our head of people to think about ways that we scale this. This second is, is it’s interesting. Right? I was telling you before how I went from being super in the weeds or in the mud to being out of the mud in the clouds.And it’s like, I’m in a lot of ways back in the mud now, because now, like one of the things I spend a lot of my time on is as a creator myself. So building my brand on social building, my podcast founders journal, which I love doing. and the reason I love doing it is. I know that I would be doing it if I was involved in Morning Brew or not.And like, that’s a great mental model. My mind is like, if I would do something on my own time, not within the walls of Morning Brew and I just have the opportunity to do it within it. It’s a re it’s a good sign. So spending time creating content. So hosting founders, journal, creating content at the intersection of like, it’s almost like the, the w who I think about my audience being is like the mindful business leader.So like the person who’s looking to elevate themselves as a business thinker, as a manager, as a leader, but also just like, as a person, because they understand it’s all very intertwined. How you think in your life. Impacts the way you work as a professional, but also understanding business is really important to understand, to, to be a successful professional.So being a creator is a lot of my time. and then the third is honestly just acting as a top of funnel for opportunity by being a creator. It gives me leverage to have relationships by having those relationships. I can act as a top of funnel to funnel into the business in my kind of two major ways.One is on the advertising side. So as we scale Mortimer’s business, both with advertising and non-advertising having relationships with big brands and agencies is really important. That’s one side. The other side is actually on the creator side as morning, Bruce scales as a brand. And we start actually bringing in creators to Morning Brew’s platform to, to launch shows and products within the Morning Brew, ecosystem in kind of like our music amusement park, the, the, the house of Brew, Getting B building relationships with creators will be, I think, a really big asset to bring in people to the Brew in a way they get really excited about our brand, but also we can launch great shows with them.Nathan: [00:14:10]Yeah. That makes sense. There’s a lot of different directions I want to go. maybe before we dive into this, the scale and everything that you’re going into now, maybe just give us like the high-level timelines of founding one in Brew, and then through a couple of those key stages with like subscriber counts and, and some of those things.Alex: [00:14:32]Newsletter, not called Morning Brew called market corner was a PDF attached to an email newsletter was sent out in, December, December 6th of 2014. It’s when I was a senior at the university of Michigan. Austin was a sophomore, I didn’t know, Austin at this time. First Morning Brew went out March of 2015.So my second semester, senior year, this was after I saw some traction with market corner. I wanted to bring on someone to help me. Austin raised his hand. He joined me as a co-founder of this non not really business, but project first Morning Brew in email form launch in March of 2015,Nathan: [00:15:13]What made you pick a newsletter as the thing to launch? Were there people also doing it? You know, you’re in the finance space and all of that.Alex: [00:15:22]Yeah. It actually had nothing to do with other people doing it. It was really a function of, we asked ourselves two questions, one, what is inexpensive? Cause we didn’t have a lot of money to spend on whatever content we created, that there was no, you know, there weren’t easy, low cost ways to create content at the time.And then the second was. What is a medium that the college business student is already consuming, that we don’t have to reprogram their behavior. So, like for example, an app app was interesting, cost a shit ton of money. We didn’t want to, or have the money to spend on it. Website, website, not costly, but like how many websites are there that a person actually types in the URL, obviously, very few.And so the question was like, how are people going to find us then? Especially if we know nothing about like SEO or anything. So that’s what led us to newsletters cheap and doesn’t require behavioral change from the college of business student. So that was that, I ended up graduating from Michigan, worked in finance for about a year until there was a, to me just like a clear fork in the road had to do finance full-time or had to do a Morning Brew full-time.But doing both of them, wasn’t a viable option. I quit my job September of 2016, right. Austin graduated from Michigan in June of 2017 and joined me full-time. So we’re both full-time by middle of 2017. And I would say, yeah. So when I, when I quit, we were at, I think 70,000 subscribers,Nathan: [00:17:04]Okay. So it’s a lot.Alex: [00:17:05]We’re at 77,000 subscribers.We hadn’t made a dollar yet. we, so other other important dates, we from 2018 to 2019, we went from a hundred thousand subscribers. So just to give you context, it took from September of 2016 to 2018, it took that long to gain another 30,000 subscribers. And then from 2018 to the beginning of 2019, we went from a hundred thousand subscribers to a million subscribers.So that was like a big inflection point for the business. What caused that? That was honestly getting the flywheel going of paid acquisition. it was the way we always come conceptualized. Our business was when we had our first newsletter. If our newsletter was the business.It was step one, create great content to get that great content in front of a great audience.And step three, get that great audience in front of the right advertisers. Once we had that process going, we were getting money from advertisers. Then we could say that cashflow from advertisers, we can either invest in people to assign to one of these three steps to get the flywheel spinning faster, or assign it to paid marketing, which we had never done before.And so by ramping up, paid mark marketing and doing it in a smart way where we were trying to acquire high quality subscribers, which at the time we defined as someone who opens at least five of their first 10 newsletters, that’s really what got us to grow quickly between 2018 and 2019. And then 2019, starting in 2019 is really when we tried to go from newsletter, like, a newsletter as the company.To a newsletter company where it was a portfolio of newsletters, not just one newsletter. And then it was call it like 2020 when it was really thinking about newsletter company to true media brand outside of just newsletter as the medium. And those were kind of like the key dates in the company’s history.Nathan: [00:19:08]Yeah, that, that makes sense. and then when just verbose context was the, the sale to the SunSetter. It doesn’t require a majority stakeAlex: [00:19:17]Yeah. Yeah. So we closed on the insider deal in October of 2020. so however many months ago that was, you know, seven, eight months ago.Nathan: [00:19:28]I want to talk about the data acquisition side of it, because so many people are building newsletters through free content. you know, any of the original blogging crew, right? It’s been running, newsletters are transitioned. That would say like search is one of their biggest channels, you know, organic search for driving newsletter subscribers.But I think a lot of newsletters, especially like single author newsletters,really aren’t focusing on paid marketing nearly as much. So I’m curious, what are some of the things that worked? why did it work for you? When a lot of people get into paid marketing and, and they really struggle,Alex: [00:20:02]Yeah. So on the paid acquisition side, basically the idea is we wanted to accelerate growth. and we couldn’t try like newsletters aren’t inherently viral. Our referral program was doing well. And our referral program is what gave us the confidence to do paid marketing because every subscriber would be worth a little bit more than one subscriber since we could count on many of our subscribers to get referrals, but that wasn’t what was going to be like truly create hockey, stick growth in our business.And, and so in a lot of ways, that’s why, like, I think it’s so important to emphasize if Morning Brew did not spend on PA like people talk about the downfalls of paid acquisition and you obviously have to be careful in your relationship with paid acquisition. But if we never did paid marketing, like Morning Brew has 3 million subscribers today, we would maybe be sniffing a million right now, like maybe.And so it just was so important for our growth and it was important to do it in a, in a way where we were at least trying to be smart about acquiring the right subscribers and understanding what channels, did well for us. And so, for example, like. Email newsletters was one of the best other email newsletters was one of the best channels for acquiring other subscribers.And so, but if you looked at it just on a acquisition cost basis, and that was the only way you looked at it, you would have never kept, advertising on email newsletters because it was very costly because let’s just use the example that the average subscriber that we got from advertising and other emails was like eight bucks.And the average subscriber from Facebook was let’s just say like two bucks. If you only looked at, in that way, you’d only keep pouring money in Facebook, but the quality of subscriber, the, the number of opens of an email newsletter driven subscriber versus a Facebook subscriber was completely different.And so that’s why looking at acquisition cost of a high quality subscriber in the early days was like the number one metric we looked at for paid marketing.Nathan: [00:22:00]Yeah, so you have to have that longer term view. And that’s interesting that you’re saying of, you know, five open five out of the first 10 emails get opened because you have to have some kind of quality metric. Otherwise it’s just, if quality is defined as a record in the database, then, then you’re right.Like some random channel like Facebook or something else is going to be the cheapest, but not the best in the long term.Alex: [00:22:21]Yeah. And then again, like you’re just running the R the arbitrage that so many websites have been built on is if you just acquire cheap subscribers, but they’re not actually quality. At some point what’s going to happen is like the cost of you acquiring those subscribers and how much a brand is willing to pay you to get in front of them.Once they realize they’re not quality subscribers, it’s going to invert and your business model is going to be broken.Nathan: [00:22:44]Yeah, that makes sense. Were there other things so beyond sponsoring other newsletters, were there other paid channels that worked really well?Alex: [00:22:51]There was, there was, an Instagram creative that did very well for us for a while, which was basically, a fake, a fake text conversation between two people where it was like one person was like, did you see an X so-and-so or something? And something happened in the news. The person responds no.How to hear about that, that the person responds, oh, it was in Morning Brew. and then like, whatever, it was a fake conversation, but it was one of the first, I would say examples of fake conversations as ad creative that did extremely well, because I think it felt, even though it wasn’t authentic, truly, it felt way more native than a lot of different forms of ad creative.It wasn’t overproduced. It was just an experience that a lot of people felt like they could share because everyone texts. So that did very well. YouTube advertising has continued to do really well for us. So buying a direct. Ads from YouTube influencers where they do like their own reads of them reading and re video, recording them, scrolling through the Brew while drinking a coffee at their, at their table that has done very well for us as well.Nathan: [00:24:03]Is that a lot of, well, so the first thing that I liked about that is that the money is going from wanting through to the creator, you know, rather than like, that’s something that we run into that I can work at is like, do you really want to hand over all this money to Facebook and Google and everybody else when we could just give it straight to the creator?And so, I liked that approach.Alex: [00:24:23]It’s true. And, and to that point, yeah, to that point, it’s like, ideally yes. The, the, the biggest question just become scalability. Right? How do you scale that? Like, that was the biggest thing we saw with email newsletters is. How do you scale it for two reasons? fragmentation and, audience size. Like there are a lot of email newsletters that we burned through their audiences because we advertised in them so many times.So you just burn through audiences faster when you’re working with let’s just call like any form of micro influence or smaller influence than a platform that has multiple billion people on it. And the second is fragmentation, right? When you’re advertising on Facebook, Facebook is the one place. and then obviously, like they can decide whether to put it on mobile, in what format on Instagram, et cetera, with like email newsletters or YouTube creators.You like you, it’s a massive job. It’s a super time consuming job in itself. If you want to scale a channel to say spending. $250,000 a month in email newsletter ad spend, like you end up having to either have someone in your company that spends all of their time on it, or you’re hiring like an agency to be effectively the glue that takes the fragmentation of the email newsletter space and brings it together.Same thing for YouTube influence.Nathan: [00:25:43]Did you end up hiring someone in-house to do all that? Or did you first do it with an agency?Alex: [00:25:49]So we first did it with an agency. it was actually, one of the bruise investors in our, friends and family round. and then. So for newsletters, we were using agency for YouTube. We were, we were it’s interesting. So it went from agency to person in the business that was managing the agency because like, it was a job in itself.It, it sounds crazy, but it’s like a job in itself to manage the agency to make sure like they are optimizing the creators the right way. Or maybe some of these agencies, like don’t have all of the creator relationships. And if we come across a creator that we think is a good fit, like that is a job in itself to recommend it to the agency, the agency to vet to then decide if they want to allocate part of the budget to it.So we have generally gone where we use agencies, but there was a person on the marketing team tagged to working with the agency partner.Nathan: [00:26:48]Yeah, I was smiling then. Cause we can work. I have done the same thing. We’re like, oh yeah, there’s an that with a person on the internal team, running the agency, you know?Alex: [00:26:58]Exactly and an agency. I think the assumption should be much to say you have T you have 10 hours of work on something for a person in the company. If you go use an agency it’s not 10 to zero. It’s like 10 to four.Nathan: [00:27:12]Yeah, that makes sense. I like the idea of, or everything you’re saying makes sense about, managing the ads and the relationships. Cause then you’re like, yeah, let’s sponsor this. And it’s easy to fork over five, 10, $25,000 for the sponsorship, but then there’s like, what’s the copy? What’s the ad read winch, this all be timed.How did you handle tracking? That’s probably the biggest thing that I could have run into of like, you know, Facebook rolls up your ad buckets and all you’re tracking and you’re like, there’s your cost per lead? And in this case, right, someone doing their anger, you know, a pre-roll on their YouTube channel, it kind of sucks.Alex: [00:27:50]Yeah, they said that is, that is a, that is part of the four hours that, that like someone internally still spends on it. you know, it is literally managing a sheet of all of our growth partnerships. You know, it is working with our tech and product team to make sure we’re generating unique links for every new influencer or marketing channel we’re working with.Or we’re AB testing copy. We’re creating two links that have unique tracking and it’s literally our marketing team is, managing a full effectively like database of all of these unique tracking links. And over a period of time, I don’t know the exact period right now. They’re going in and looking at what the performance is.And for YouTube specifically, like YouTube is different than like email newsletters, right? Because for, for email newsletters, you can assume, I don’t know. In the first two days you’re getting. 90% of the subscribers you’ll drive from that advertisement, for the life of it. And then you’ll get 10%.That’s like the long tail for something like YouTube. My guess is it’s closer to like, you know, 70, 30 or 60 40, because YouTube is effectively just, you know, a Google video. It you’re going to con view like view count is going to constantly grow for the creator. Not just as more people are searching, but also if you’re kind of taking a bet on the, the growth of the creator, if say a creator we work with today who has a million subscribers has 3 million next year, you’re going to find a ton of growth on that video that you had this native promotion on, simply from them just growing as a creator.You don’t experience that same thing with email newsletters because obviously it’s scent and it’s kind of in the past, irrespective of the growth of the email newsletter,Nathan: [00:29:35]So, yeah, that’s true because the email has the upside of it’s clickable. There was a UTM parameter on that link, all of that. But it’s a moment in time promotion. Whereas the YouTube video is it’s tied to that video or that series of videos and it lives there forever, which is the same thing that podcastsAlex: [00:29:54]Yeah,Nathan: [00:29:54]The same ups and downs.Alex: [00:29:56]I think I’ll also say that I know was a really successful strategy for a few newsletters back in the day. I don’t know if anyone’s still does. This is, is like advertorials. so I remember, I think it was the hustle did an advertorial with hint water, where they wrote up like a, basically what felt like an editorialized piece on just the story of hint water, the story of their founder and CEO, Kara golden, and kind of like how they’ve revolutionized the flavored water business.And then what ended up happening was it lived on the hustles site. It had links out to hint, hint. Basically, they did all type shit ton of paid promotion to that piece on the hustle site. And they just kept putting money in it. As long as the return on ad spend made sense from however much money they were putting into Facebook and all these other social platforms versus how much people were actually buying hint water on the back of this article.And just from them spending so much money because they continue to see strong Roaz. I I’m pretty sure like hundreds of thousands of email subscribers came through that one advertorial,Nathan: [00:31:09]Email subscribers for the hustle.Alex: [00:31:10]Correct.Nathan: [00:31:12]So it’s even more,Alex: [00:31:13]The advertorial piece lived on the website and pop up for the newsletter, came up as you’re reading that advertorial.Nathan: [00:31:19]Oh, interesting. Right. Cause it makes sense. Like there’s a version of that, that we did in the early days of ConvertKit. And honestly, there are these things that I don’t know why we didn’t do more of when you think that word. Why, why did we only do that once?Alex: [00:31:30]Totally.Nathan: [00:31:31]But there’s like pat Flynn, who is Joe blogger podcast or he wrote this article titled why I switched from a Weber to Infusionsoft, to convert kit in like 2015, I think. And, it had his converted affiliate links in there. He presented to his audience that did really well. And then we went, that’s a nice headline. What if we like to have to tells a nice story?And so we started running that as a paid ad to his, you know, he was even, he was even getting likes off and everything and it just, it converted so well.Alex: [00:32:05]In that scenario. You were, you were, you were Hintwater and PatFlynn was the hustle.Nathan: [00:32:09]Right. But I hadn’t thought about that from the hustles perspective of they’re like, yeah, you fit the bill, we’ll write the editorial and lens the brand and the, you know, the website real estate.Alex: [00:32:23]Yep.Nathan: [00:32:24]Well,Alex: [00:32:25]I think part of the reason was that I think at some point Facebook started cracking down on it as they saw individual brands spending like. Millions of dollars on these advertorial pieces, which I’m interested in, why, you know, why, Facebook really cared. But yeah, I th I think that’s the only reason, but it definitely was something that worked, for a number of brands.Nathan: [00:32:48]Yeah, you have like a whole thing. The morning group is very known for, if we were to mention referral programs related to email, in relation to email, someone would be like, oh, like Morning Brew. so I guess two sides of it. One, what were the things that worked for them for our program? And tell us a little more about that.And then I’m always curious when two concepts get so closely associated, I feel like then there’s all these misconceptions that come from it and they’re like, oh yeah, good morning. Where did this? And it’s like, well, maybe they didn’t or did some aspects of it.Alex: [00:33:20]We, we definitely, we definitely did not create the referral that is for sure. we, you know, okay. So the way it worked was.It was just a very linear process of thinking about how we could scale. Right? So step one was we had market corner that original newsletter, the way I got people to sign up for market quarter, because there was no website.You literally had to tell me, email your email address, and I would sign you up manually. So I told my early subscribers, I was like, if you know people who are interested in this and give you permission, let me know their email addresses and I’ll type them in for them. and then I start getting email messages from random people saying, Hey, I heard about your, your Roundup called market quarter.Can you add me to your list? Serve? That was step one. Then step two was we launched Morning Brew. And we were like, how do we grow this thing? And Austin and I were still on Michigan’s campus. And basically we were like, We, we need to, we have to think about it as like a hub and spoke model where you have these hubs, which are people, classes, organizations that have access to all of these spokes spokes, being the right audience you want to get in front of.And the way you save time is you get in front of hubs. So you don’t have to go to every single spoke. And for us on Michigan’s campus, the hubs were business classes, business clubs. And so we spent, I don’t know, probably three or four weeks going to every single business class and every single business club on campus.And it was super successful. We’d go into a class. We would give the Brew spiel for two, two or three minutes. We’d say, Hey, if you’re interested in it, we’re going to pass around a sheet of paper, write down your email address and you can sign up. And that’s what we did in every club in class. It was a great, like early bootcamp and just like.Doing things that aren’t comfortable, like convincing a professor, why you should be able to sell something in their class. It was great for early selling and storytelling. And it was really good in thinking about just like an early exercise in conversion, because getting people to write on a sheet of paper, rather than asking them to take out their laptops and type Morning Brew into the URL, the old school more antiquated way did far better because you were just putting the utensil in the hand of someone and asking them to write it versus go through all of the steps.So that’s what happened. And then we were like, we’ve cleared out Michigan. We have a strong hold on, Michigan. How do we do this in other colleges? Because Michigan is not the only college where students are going to care about better business news. So we were like, how do we find the Austin’s? And Alex’s in other places, that’s what led to our ambassador program.So we had our ambassador program running and we were getting, you know, let’s call five to 10,000 new subscribers a semester by working with ambassadors. And there’s a whole story about the learnings of the ambassador program in the early days. But. Take the ambassador program, then we were like, okay. But we’re seeing that they’re actually people that aren’t ambassadors there that aren’t college students that really love Morning Brew because it’s just quick, it’s conversational.They feel like they’re not talking to a robot. And so we’re like, how do we make everyone an ambassador? That’s what led to the referral program? The way we start our referral program is we first found out about kickoff labs. That was the website we used at the time. I think there’s another one called viral loops, that we were looking at at the time.And we, we use kickoff labs and it was fine. And the reason we found out about kickoff labs I believe was because I think when Robin hood launched, I, if I’m not mistaken, they did their launch with kickoff labs to build up like a, the wait list for Robin Hood’s launch. And so we started using kickoff labs.It was good, but a law allowed for no flexibility in our website. And so we couldn’t do anything with our website. So we’re like, this kind of sucks. We have no flexibility. So we’re like, we need to, how do we build our own? We looked up how to build your own referral program. And of course there was, there was an article on Tim Ferriss’s blog about Harry’s razors and how Harry’s razors use their user referral program.When they launched the company to build up an email list of a couple hundred thousand people. And in that was like this, this, the actual code for building out your referral program. Then we were like, okay, let’s we want to do this. We went on Upwork. We found a developer in Ohio who we paid $500 to build effectively the Harry’s razors landing page.Like it was the same exact thing, just different referral rewards and a different background rather than the wooly mammoth that they had. And, And the developer we found on Upwork had said that he had built this referral program like three or four times prior. So he probably literally didn’t have to do anything.And it was just $500 in his pocket. And so we did that and then we ended up, as we brought developers onto the team to get it to scale, they rebuilt it in like a totally custom way. All that to say that we did not create the referral program referrals at their core, literally are just bringing scale to a friend, telling another friend about something they enjoy and being rewarded for it.That is exactly that is as old as time. And the technology is pretty old. Also like people think it’s like, like wizardry and it is really the simplest tech. but we’ve found it to be so valuable. The reason we find it to be valuable is we found rewards that incentivize our power users, and we feel really confident about a product that gets our readers really excited to share with their networks.If either of those two things didn’t work like the rewards weren’t good. And it was a friction lit, it was a high friction process or the newsletter and our content wasn’t good. The referral program would never work. And I think a lot of people say they want to do a referral program and they’re either not thoughtful about the rewards or they’re not thoughtful about why a referral program does or does not make sense for what their product is.Nathan: [00:39:17]What are some of those examples of rewards either in general that, you know, do, don’t work, or more specifically from what you learned in boarding group that worked?Alex: [00:39:25]So what I will say is a lot of people try adding a referral program to a, what I would say is more of a marketing driven newsletter. So people who have like a weekly newsletter that is a Roundup of links from their website, they strapper a referral program to it. And they’re like, we’re not growing really fast.It’s not doing anything. And I guess the question is one, do people actually give a shit about your newsletter? Why should they give a shit about your newsletter? If your newsletter is just content marketing for your website, you want people to give a shit about your website and your newsletters, just a vehicle to take them there.So why do you think people are going to share the newsletter and ultimately they end up on your website and the content they like is on your website. So that’s the first, the second is it’s always about like referral prize reader fit. And what I mean by that is like really thinking about. Who are the people who are going to want to refer your product and what is going to be the thing that gets them over the edge that takes them from mentally being like, okay, I’m on the subway.I like have five things I could do. And the thing I’m going to choose to do now is refer like what’s going to get them to that mental state. What is going to be the thing you give them that gets them to that mental state. And so it’s about knowing, like who are the people that are most likely to refer it’s most likely going to be your power users.So then it’s a question of like, who are your power users? And for Morning Brew, the power users are people who consider themselves to be a part of the Morning Brew community who feels so grateful that Morning Brew has become a tool for them to be a smarter, better professional. And for people who like really feel like they believe the Morning Brew brand, because they feel a part of the community.And so the question always was what are the rewards that make someone be able to either get more of the content. That makes them feel smarter and better in their career or what are rewards that allow them to show off their status in a community that they really feel a part of. And so that’s why like everything from morning routine shirts to Morning Brew mugs to Morning Brew, crew necks, those were a combination of things that accomplish two things.One. Give social status to someone who really identifies with the Morning Brew community, but also turns them into walking billboards because they’re products that you don’t just have in the comfort of your bedroom. They’re things you generally have either in an office on your desk that people see that like, that are seen in high traffic areas.The other was doing things like a Morning Brew, Facebook community, or our Sunday edition, the light roast, which up until very recently, you would only get access to if you got three referrals, like putting content before behind the referral world wall made people not only feel special, but felt like they were getting more of the content that they love Morning Brew for.And so it was that balance of understanding who would share, giving them a reason to share, and also doing so in a low cost way where we were really purposeful with picking rewards that were effective but efficient. So the acquisition costs from generating referrals, wasn’t super high, for example, like.Our Sunday edition, the Facebook community. Those are cost. If you want to add a cost it’s whatever the time cost is of the employee who has to moderate the Facebook community or write the Sunday edition for something like mugs, mugs are one of the cheapest forms of paraphernalia. It’s like 23 cents a ceramic mug.So the, the referral cost of a mug after getting it bought and shipped is super low.Nathan: [00:42:56]Yeah, that makes sense. Because a lot of people will default to these really expensive, you know, items or something like that. And I liked the connection that you’re talking about. It’s because it’s not the value of the reward or like the monetary value of the reward. It’s incentivizing more of those behaviors.Like the t-shirt isn’t like, oh, you gave me this thing that maybe I would have bought for 15 or $20. It’s like, no, no, no. I have this Morning Brew. T-shirt. That I can only get by, you know? Yeah.Alex: [00:43:25]We’re sending you your Jersey.Nathan: [00:43:27]Yeah. Oh, that’s good. Okay. I want to talk about monetization because you’ve been heavy on sponsorships and advertising, for a long time.Curious if you’ve done other things, but you’re also now into paid products. and so we take this in two sides. One, the like warning Brews are committed. We start there and then I’d love to also with go into newsletters as a whole paid newsletters versus, you know, all of that. Yeah. Give me your take.Alex: [00:43:59]So, okay. Well, I guess I’ll just give my thoughts onhow, like, how we made money with the Brew. So in the early days of the newsletter, first of all, we didn’t know the size at which we would be able to make. Money. I actually think in retrospect, we could have started monetizing earlier. And it’s funny in retrospect, because we were really worried about like the sanctity sanctity of the brand, which is why I think what delayed us spent, getting advertisers to spend with us in that, you know, now hindsight, like I think as long as you, as long as you’re doing native advertising with partners, you align with in a way where you don’t have too much ad load, it really should not be a concern.And if that’s a way you monetize your business, you need to do it in order to run a viable business or, or you should just think about other business models of you’re really against advertising. and so we, I think we got our first advertiser around 75,000 subscribers. I’ve seen certain sub stackers.Get advertisers with way fewer subscribers. probably at 25,000. I think the earliest I’ve seen a newsletter monetize itself, through advertising is probably 10 to 15,000. And again, you’re not making big money, but what you are doing is you’re learning whether your audience actually responds to advertisers.And you’re also building up a list of testimonials as you get bigger and bigger, that will be super helpful in selling advertisers, as you do scale, the, the initial advertisers. So the first advertiser morning, wherever worked with was a completely just through a relationship of one of our investors.One of our investors worked at an ad agency. He literally at the time referred to it as giving us some beer money. He got wa it was the first advertiser ever Morning Brew was, am Lockhart. And it was. College rings like college rings and like graduation stuff. They bought three ads in the Brew for 800 a piece, I believe.So $2,400 ad buy. And again, didn’t, it wasn’t a lot of money, but he got the process going about learning how to sell ads. And so basically from that point on, then the process was okay, how, what is going to be the lowest hanging fruit in order to monetize our newsletter? And what we said it was going to be is who are the brands that are most likely to advertise in the Brew?And what we came to the conclusion of is it will be smaller performance driven brands that could truly measure the ROI. or cared about the ROI of their ad. And so what that means is if they really cared about the ROI of their ad, they really don’t care where they’re spending, because it’s not about just getting their brand out in the world.It’s really about driving actual revenue. And so, you know, if they could advertise in a gas station TV, but that drives revenue, they’re going to do it. And so our view is like focused on more performance driven advertisers versus brand marketing, driven advertisers and to let’s start with what we consider like the chronic newsletter buyer let’s see.And what we literally did is we created, And email address of newsletters@morningBrew.com or something like that. And we signed up for 50 different newsletters and we would track every day in a spreadsheet who are the companies advertising in those newsletters? Because our view is, is if you see a bunch of companies advertising those newsletters or, companies that are advertising those newsletters, many times clearly they’re bought into newsletter as a marketing channel, which in the early days was a big point of friction because people, either thought newsletters were dead.They bucketed them in a certain place in their mind. And it was really hard to get people over the mental hump of should they advertise it a newsletter. So we went after performance driven brands that already had advertised in newsletters. That’s where we started our, our focus. We also, in the early days, worked with an agency that focused specifically on working with CA call it these like chronic newsletter brands to place them into newsletters then as T and the way that we scaled this was, we basically just said, Well, the content has to continue to be great.We have to continue to great get engaged readers so that we’re driving ROI for these advertisers. It also validated for us that we had really a really strong and, a really strong and just loyal audience in the early days, because it’s one of those things. When you work with performance brands, if your audience isn’t loyal and isn’t engaged with the brand, like you can’t fake it, it’s just like, you’re not going to drive revenue for these brands.So I think it was a really good early proof point for the value of the audience we were building and the way we scaled revenues, we literally just said, okay, let’s say we were charging a thousand in ad. Let’s just keep raising it. And we just kept raising it every single time. We talked to a new advertiser until the point in time at which.Advertisers said, Hey, like consistently said, Hey, we’re no longer hitting our return on ad spend targets. we need to like, we, we, we have to cut you guys off at it as a channel. Then once we got big enough and I would say big enough was really at like 200,000 subscribers. That’s what we were considered.I would say at scale enough. To work with big brands. I’ll also say that having the testimonial or like the case study of working with a big brand before that 200,000 point, also helps in getting bigger brands. So we worked with the biggest, the first big brand we worked with was discover card. The only reason we worked with them or were able to work with them is because we had a relationship with the CFO of discover card because the CMO of discover card was a reader who found out from their kid who found out through the ambassador program that we were running at their child’s school.And so this, we, we didn’t, it kind of like was the hack to, to not have to convince a brand marketer why they should advertise it a small newsletter because the CMOs saw the value of the audience. They were the audience and they didn’t care about that. They just said, allocate some budget to this Morning Brew thing.And so that case study not only created a mental confidence, that we could talk to big brands, but it also was something that we could show to big brands to convince them, like you’re not going to be the first one who has to take a risk on this small newsletter.Nathan: [00:50:33]Yeah. Having that, that proof point is so important. And like, we had the same thing with ConvertKit where like Tim Ferris would be a great example. Like so many people would come to us and say, can you actually handle this? Like the handle, the scale and all that. And then once we had Tim’s list on there that he goes, oh, Oh, Tim uses Yanga and like the whole list of like due diligence questions or whatever.They just like scrap all that. And, you know, and once you get that, it’s so important and your rights, and a lot of those initial things can come through like a backdoor aspect of it.Alex: [00:51:05]A hundred percentNathan: [00:51:06]What about like, what’s your take on, on the, paid products and paid newsletters versus sponsorship, like, in the sub stacked newsletter world, we take two examples would be like Lenny Rachitsky and, and Packy McCormick, right? So Lenny has his paid newsletter pack is like, forget that I’m going sponsorship. It needs a better model. And I always love people showing those, those two sides of it because you can do it a ton of different ways.Alex: [00:51:31]I don’t think there’s one way that works better. I think, hook, I think what sits at the core of this is are you building an audience or not? If you’re building an audience like a true audience, like a trusted audience, you can make either work, like I guess said differently. Do I think Paki could have a great livelihood right now?With a subscription based newsletter. Absolutely. Like I think people pay for package subscription. I think you’d be making as much as he made in his last job. Would his subscription business be as big as his advertising business right now? I don’t know, but to be honest, to be totally honest with you, I don’t know that it matters because I think once you get to a big enough size, you’ll end up having many revenue streams, not just a single one.And so I think it’s like many paths that lead to a similar place and same thing with Lenny. Like could Lenny be making a great livelihood with his more product focused newsletter? Yeah, absolutely. I don’t know how it would be doing relative to his paid version, but what I would say is it’s more about trade-offs right.So. I think by having a paid community by going paid first, it gives you the confidence and it gives you the relationship with your subscribers to do other paid things with a level of confidence. Like if you’re Lenny and you go and do. Courses, which he’s done. It gives you confidence to do that because you already have an audience that you know, is willing to pay for your stuff.And to me, this is just an, a, an LTV driver for a portion of the people who are willing to pay for your newsletter. You know, for Packy, maybe the trade off is harder because Packy won’t necessarily have the confidence day one to go launch a cohort based course, because he has no idea of the audience has the affinity to take out their wallet and pay for it.That said on the other side of the trade off is. Paki is going to have the ability to drive a larger audience because his content is able to like, you know, his content is able to maintain its vitality because it is open to everyone. And so, I’m kind of going to be Switzerland here, but it’s like what I truly believe, which is, I kind of don’t think it matters.I think it ends up converging where you monetize yourself in multiple ways. If you asking me, what would I choose to do? I would choose to CRE to keep stuff free for as long as possible to open up my audience as much as possible. But I don’t think there’s like a clear time in which I would close it off.I really do think it is based on field.Nathan: [00:54:11]One point that I hear in that is that the connection with the audience matters a ton.Alex: [00:54:15]It’s everything. You either have a real audience or you have no audience.Nathan: [00:54:20]I like it. cause that’s where all the monetization methods, everything else can, can get sorted out from there depending on what you do. So, I think that’s good. last question that I wanted to ask you about. And this is more like a, a meta business question and projects. And all of that is I see people like two different types of ventures that people start.One is the, like, I’m going to start a newsletter letter. I’m going to start a blog, any of that. And they build it up. It has like side hustle, the full-time vibes to it. I don’t know how else to describe it. And there’s other people who start something and you’re like, it’s a force of nature. And it like turns into something like one number where it’s millions of subscribers.You see it, even, you see it, startups agencies, like one person starts an agency. And like years later it’s like five people and someone else starts an agency and it’s the same business model and all that. And years later it’s like, I don’t know, VaynerMedia, or something on that scale. And so I’m curious when you see, how do you think about those things?As one of those people who’s taken like a newsletter, which is typically a small business and grown it into something massive.Alex: [00:55:31]When I, when I reflect on this, I really think it’s about ambition, right? Like, I think it’s based on ambition and risk tolerance.On one side you could say morning bruise, massive on another side, you could say, Morning Brew actually potentially could be bigger right now, if we raised more money, we are aggressive, more aggressive in our growth strategy.And for the people, like you say that their thing is less of a force of nature. It’s interesting because maybe their goal is if it turns into a force of nature, that’s great, but maybe they don’t want a force of nature. Maybe they just want something that literally opens up their time to do anything else in life.So, I don’t know. My answer would be that while to have the opportunity for something to be forced, to be a force of nature. I think it really has to be something that serves a specific audience in a really exceptional way. And it’s an even better case if it’s a growing niche. Like I think people think about niches as small.And obviously like now people talk about all the time about niches and small. It’s just focused the ideal scenarios where it is focused and scaling. So like, what is a trend you’re latching onto that say has a hundred thousand people possible audience today, but like 5 million people, five years from now.So, I think that is one piece of the pie where you have to have that to have the chance of being a force of nature. But then I think you have people who have not become forces of nature, maybe early making 150K with their product, but. Maybe the reason they don’t have that ambition is because ambition requires time.And that time they actually think there’s an opportunity cost too in spending that time elsewhere in other aspects of their life. And so, like, that’s kind of how I think about it is, it’s it’s ambition, you hear the word ambition and you’re like, oh, that means someone really wants it, or they don’t really want it, but maybe there’s actually more nuance to it where it’s like, Not that perse someone really wants or not really want something in life, but it’s actually the reason they really, maybe they really want something.Maybe they really want to make their thing, a force of nature because that’s what they’re super passionate about. And that’s where they would love to give their 70 hours a week. Or maybe you have someone who is not a force of nature. It actually is a great product market fit and it’s a scaling niche, but what they really want is giving 30 hours a week and the other 60 hours a week, they’re spending with their kids.And that’s not to say people spend 70 hours a week. Don’t want to spend time with their kids, but I think there’s a spectrum. And that’s how I think about it.Nathan: [00:58:08]Yeah, that makes a lot of sense. And I think we see people scale up any of these opportunities when they have leveraged coming in that they’re able to, to either scale something crazy, or they’re able to use that leverage and redirect it to something else.Thanks so much for talking today.Where should people go to listen to your podcasts, follow all the new stuff you’re creating and then yeah, everything else?Alex: [00:58:32]Yeah. you want to follow me on Twitter? It’s @businessbarista. And then podcasts just on any of the players. It’s called Founder’s Journal and, three days a week, eight minute to 12 minute episodes. And the whole idea is like accelerating your career as a, as a monitor business leader.Nathan: [00:58:50]I like it. Well, thanks so much for coming on and we’ll have to chat soon.Alex: [00:58:53]Yeah. Thanks so much for having me.

Eric Jorgenson is a writer, course creator, blogger, and podcaster. He is also on the founding team of Zaarly, an online marketplace for hiring home service providers.Eric has been publishing online since 2014, and operates a monthly newsletter. His business blog, Evergreen, has educated and entertained over a million readers.Eric is the author of The Almanack of Naval Ravikant: A Guide to Wealth and Happiness. Naval Ravikant is an entrepreneur, philosopher, and investor. Naval's principles for building wealth and creating long-term happiness have captivated the world.The Almanack of Naval Ravikant is a collection of Naval’s wisdom and experience from the last ten years. It's a curation of his most insightful interviews and poignant reflections.Eric’s current project, Building a Mountain of Levers, teaches “how to accomplish superhuman feats by playing a different game — building leverage.”In this episode, you’ll learn: The most important things to do when starting a newsletter What leverage is, and how to use it to exponentially scale your business How a random tweet blossomed into Eric’s best-selling book Links & Resources The Almanack of Naval Ravikant Naval Ravikant’s podcast @FAKEGRIMLOCK Ben Caballero Rework Anything You Want: 40 Lessons for a New Kind of Entrepreneur Peter Bevelin Poor Charlie's Almanack: The Wit and Wisdom of Charles T Munger Berkshire Hathaway Letters to Shareholders Eric Jorgenson’s Links Eric’s website: ejorgenson.com Twitter: @EricJorgenson Episode TranscriptEric: [00:00:00]Munger said the best thing a human being can do is to help someone else to know more. Everyone has something to teach. Everyone can participate as a student and as a teacher at different points in their lives. There’s always somebody who’s one step ahead of you to learn from, and always somebody who’s one step behind you that you can help.I think counseling and learning keeps us humble and keeps life exciting. Teaching is rewarding. The fact that we can all kind of be a part of it is really fun.Nathan: [00:00:29]In this episode, I talked to Eric Jorgensen, who is the author of one of my favorite books. It’s actually the book that I have gifted the most recently, and that is The Almanack of Naval Ravikant, which is a distillation of the wisdom writing podcast episodes of Naval. So Eric did this awesome project where you compile all this edited down into a book.And I know we talked about that at the end of the episode, but throughout the episode, we talk about online education, leverage—we spend a lot of time talking about leverage—which is sort of this thing that Naval has really made the centerpiece to a lot of his content that he’s produced.Eric has gone even further and produced a course on and talked about so much great stuff. Really important concepts that I think you’re really gonna enjoy. So I’ll get out of the way and we’ll just dive in.Eric, thanks for joining me.Eric: [00:01:18]Thanks for having me. You’re on like the Mount Rushmore of heroes of like bootstrappers, turned content creators, turned bootstrappers. So like I’m super excited to be talking to you in any context. This is going to be fun.Nathan: [00:01:30]Well, good. And now, now I’m curious who else is on Mount Rushmore?Eric: [00:01:33]I knew you were going to ask me that. And I don’t, I, I don’t know. I have not prepared for it, but we can start Photoshopping it up later.Nathan: [00:01:41]Yeah, exactly. That’d be a really good use of both of our time.Reading through all of your stuff online, you are obsessed with education, specifically online education. You’ve got Course Correctly where you’re like reviewing online courses with a friend of yours.You’ve got like there’s a lot going on and you truly care a lot about the details of online education, and I’m curious, like why, where does that come from? Where does the interest turn into obsession?Eric: [00:02:12]So long-term I think like going to Mars is awesome, and curing cancer is awesome, and like solving world hunger is awesome. But education is the variable with the biggest coefficient into all of those things over the long term. So, like all of us who are alive right now are kind of like, Oh God, we’ve got to solve all these problems that are like affecting us.But if we just kind of look at the species over like a few hundred years or a few thousand years, like our ability to educate ourselves. And then the next generation is like a huge, huge, heavily weighted variable. I guess into like the outcome that we achieve over a long period of time and like how we can affect that.And I think like there’s no, you know, the, the first principles kind of like where’s the laws of physics limitedness is like, we have the ability to be so much better at education than we are, and we are. There’s some specific context where we’re incredible educators. Like our doctors are incredibly well-educated; the rigor of like a pilot’s education or doctor’s education compared to, you know, somebody who maybe like a writer, like different creative pursuits or do an MBA, like is just, we’re just missing easy opportunities to kind to become significantly better.And the internet lowers the cost of that and increases the accessibility of it. And so I think we’re going to see like a really kind of cool transformation of that over our lifetimes. I was excited to kind of see it, see it come together.Nathan: [00:03:40]Yeah. So what I hear in that is there’s individual pursuits, you know, that will like advanced civilization. You know, in like one very specific and highly effective area, but then education is like the rising tide for everything of like, if you can help people teach well, you know, learn well, any of those things and make those, those tools and Content, everything available, then that can go in any, any, and every direction.Eric: [00:04:09]Yeah. Yeah. I mean, like Munger said, like the best thing that human being can do is to like help someone else to know more. And I think that’s a really, like everyone has something to teach and. We are all trying to learn. And, it’s something that everyone can participate in as a student and as a teacher at different points in their lives.And there’s always somebody who’s like one step ahead of you to learn from, and always somebody who’s one step behind you that you can help, kind of all the way. You know, through your, through your life. so I think it’s a really interesting thing and I think constantly learning keeps us, keeps us humble, and keeps life exciting.And teaching is fun and rewarding in a way to kind of solidify the things that you’re learning. It’s just a really, it’s an exciting thing. And like the fact that we can all kind of be a part of it is, is really fun and that the internet is making it much more accessible for everybody, and change, transforming it, right?You can learn while you’re doing while you’re like in the context of a project that you’re already trying to accomplish, is really cool and kind of a new thing. And. I, the rate of change is just so crazy that like the rate of learning has to match it and where I don’t think we’re quite ready for that yet.Nathan: [00:05:23]Yeah, there’s a lot of stuff in there, but what about when someone is maybe when someone’s starting a newsletter or starting online, like coming into this world of online business and audiences and all of that, what are some of those things that you really try to teach them that. Are like those two or three really pivotal things where like, when you understand this, you will see the world differently.Eric: [00:05:45]Yeah. So I think there’s. The first thing. I mean, if somebody is at zero, like the first thing I was, I was like, start doing like you, you will learn much better in the context of doing, which is not a thing I used to appreciate. And I actually wasted a lot of time, like trying to learn before I did. I think,Nathan: [00:06:02]You had a tweet at one point. I think you were saying like, and I’m trying to remember if you were like, find yourself reading something for the third time, or like learning about something for the third time. Like it’s time to start doing instead.Eric: [00:06:15]Yeah. Yeah. And it’s like, it feels good to learn and like, feel like you’re getting closer to knowing how to do it, but like, Learning how to do something is a cheap way to get a fraction of the dopamine of actually doing it. But it doesn’t really get you that much closer to doing it, especially if you’re on like your second or third rep through.So yeah, I would think like, you know, start that newsletter, like send an email to like five people throw up a Google form, like. It’s really, it’s easy to get started. And when you encounter a roadblock, like go learn how to remove or overcome that roadblock. but don’t try to anticipate too many steps out, just like get work done.Even if you do end up down a dead end, like that proof of work and effort will help you. Kind of contextualize when you hear the right answer or when you go, you know, find a friend or mentor or teacher and say like, Hey, look, I tried this thing and like, it didn’t work. And I don’t know why I’m like, that happened to me this morning.I was like working on this XY project and like, like I’m in a dead end and I don’t know what to do. And I call the front and he’s like, here’s what I would told you if you talked to me two weeks ago and I was a part of me was like, shit, that was, that was like expensive. Mistake time-wise. but it’s also like a lesson, a cute lesson learned. So I’m going to remember that one, much more.Nathan: [00:07:37]I like the idea of working towards something like until you get stuck. it’s probably 2011 to 10, somewhere in there is really getting into designing and building an iPhone applications, which I didn’t have a strong background as a developer. I was, I knew the design side, but you know, I was like objective to like, let’s learn this.Let’s dive in. And. One app that I was building, I would code until I got stuck and could not figure it out in one direction and be like, okay. But then there’s also the other feature I’d code that way until I got stuck in like stack overflow, couldn’t help me anymore. And you know, and I do that like three different directions.So I’m like, okay, I actually can’t really meaningfully work on this anymore before I, either get help or substantially level up my code knowledge. And so then on like a Saturday, I would go over to a co-worker’s house and. Say like, okay. Here’s the areas that I’m stuck, you know? And he’d been developing iOS apps for a couple of years.Well, it’s still pretty early, so yeah, I guess two years, three years at that point, And he’d be like, okay, I see where you’re stuck, but let’s take a step back. Let me under, like, let me explain number of types to you. Do you know about floats and integers? And I’d be like, now he’s like, alright, well, computer science one-on-one, you know, like some of those things, but it was really important to go far enough to where I got stuck myself. Rather than just being like, I don’t know. I need somebody to teach me how to build life on apps.Eric: [00:09:00]Yeah, that like is he has a similar thing. So when you were, w were you writing that book at the exact same time that you were like learning that stuff yourself for the first time?Nathan: [00:09:10]I had learned the design side pretty extensively and that’s what the book was about. and so it was probably a year before I wrote the book. and so I had been doing a lot of the design side and then I was also trying to do the development because sometimes there’s this weird debate that happened.Of like, is it better to be a designer or a developer, which is the dumbest debate you could ever get into, but you’d see it like popping up all throughout the internet. And I remember thinking in my head like, well, office is better be a designer because I am a designer. But then I had this moment where I thought about it and I was like, wait if a developer build something, it will function, but it’d be ugly.If a designer design something, it will look pretty. And it won’t do Jack, like it’s not actually useful. And so like in that realization, I was like, Oh, I guess I’m going to, like, if I want to keep doing like indie projects on my own, I’m going to learn to code. And that’s when I got into that side. And then probably a year later I wrote the book on, designing iPhone applications.Eric: [00:10:11]Yeah. That whole period, everybody, every designer was trying to become a developer and every developer is trying to become a designer, but like the same timeNathan: [00:10:17]Yeah, I it’s interesting. let’s see, where were we going with that?Oh, particular things that, so that people should learn. So we’re talking about like, the first thing is actually do it,Eric: [00:10:29]Yeah, just let’s start, like, yeah. Start putting skin in the game, like set a goal, set a mission.Nathan: [00:10:35]Yeah.Eric: [00:10:36]You know, open up a page, build something tiny, no matter how small, like, just start doing before you start learning. Cause learning like as important as education is like, you can spend your whole life learning and no time doing.And like it’s a lot like a designer designing an iPhone, have those like a very pretty wireframe. It’s like, wow, you have a lot of PhDs. Did you ever do anything with Elvis? He was like, Nope.Nathan: [00:10:59]Yep. That makes sense. One of the other things that you’re like really obsessed with that I’m also obsessed with and I love talking about, which would probably be what I would put in the list of like the second thing to teach people. it would be leverage you and just. How, how that works. I feel like so much of your personal brand online now is tied into like being the guy, talking about leverage, which is amazing because more people need to learn that.So how do you think about leverage and, and what are the parts of that fascinate you the most?Eric: [00:11:28]Yeah, I think it’s, I think leverage is super important to know. I mean, I think everybody should know the mental model at the very least, especially when they’re starting out. even if they don’t know a ton of the mechanics, it’s like compounding, right? Like. You’re told you’re supposed to like save money, but you’re not really sure, like what the point is, unless you get compounding.And then you’re kind of like, Oh, like I should be saving and investing because it means I’ll be able to retire like 20 years earlier. And leverage is kind of the same way. Like when you’re first starting out, you’re trying to figure out like what you want to do and how you want to do it and how to kind of plan for growth in your career over time. And if you don’t understand if you’re, if you are blind to leverage and like where that leads you, you’re going to end up down a little bit of a dead end or in a spot where, you know, you’re maybe in a job where you’re just trading time for money or you’re in a job that’s extremely unlevered and you end up feeling like you’ll never earn more than $60,000 a year because you don’t have a way to apply, leverage to what you’re doing.So I think like, it’s, it’s really interesting to see all the people. I think you are a prime example of this who kind of like without ever, probably using the word leverage, you’d like intuited, what it was and how to get more of it and build it over time, the last like 10 years. so I like leverage from my perspective and the way I kind of organize and share thoughts around this, kind of comes in four forms, which is tools, product people, capital.So tools being like anything from a hammer to a chainsaw, to Xavier, product being any form of like capturing and preserving your judgment or experience in code in media, you know, we’re, we’re recording a product right now. but it could be a blog post. It could be a book. it could be a movie and then working into people.So everything from like, Fiber. So task-based labor up through like building a whole team. and capital kind of comes in a variety of forms, but like usually money. so all of those kinds of things build on each other and you can sort of trade them for each other and you’ll end up with like constraints and bottlenecks and things, but like over time, you know, you go from.Starting a newsletter to writing a book, to building a course, to building a software platform. and you go from, you know, some very specific tasks based help. to maybe a part-time assistant to maybe hiring an agency to maybe a hundred people full-time, and the capital grows and the margins grow.And like you sort of increasingly reinvest in higher margins of leverage that are more self-sufficient and longer levers so that they can move, you know, have quote unquote heavier loads, and help you kind of accomplish more with the time and experience and judgment that you have.Nathan: [00:14:14]Yeah, it’s as simple as an example of that, like in my life would be going from designing iPhone applications for other people, you know, which is very. One-to-one like conveniently, it’s a high paid skill, so that’s better than other activities, but you know, it’s still not there. And then teach, you know, creating a, running a book, creating a course teaching that.Now there’s real leverage because money and time are disconnected. And then going up from there would be. What did I do now? I mean, I guess the next thing was like creating that leverage from software in a recurring way, or like the number of people that are going to buy a course or consume content compared to the number of people that now use ConvertKit.And the other thing is the. Because, like you said, the compounding effect and that’s the magic in SaaS and they’re occurring in the, you know, the recurring business. It’s like, you don’t even have to have that good of a growth rate, but it compounding over time, and continuing to do it for a long time, then it gets to the point that the leverage is just pretty incredible.And like now, you know, 350,000 people use ConvertKit and it’s like, Oh, well, that’s sort of a different scale than. You know, the, the like the hours I put into designing an iPhone app for, you know, an individual client .Eric: [00:15:32]Yeah. And it would have been correct me if I’m wrong. Like, I don’t know that the details of the story there, but I think it would have been really tough to just make that huge leap. Right. Like even if you knew you wanted to end up building a SAS app, you know, in a high margin business, like even if you knew that that was your destination, would you have been able to just kind of like jump straight there without some of those intermediate steps?Nathan: [00:15:54]I don’t think they think. So there’s so many lessons that you have to learn along the way of like, well, so I’ve read about this a little bit. In my blog posts, the ladders of wealth creation is like making some of these leaps between steps of like me selling you on something. One-to-one that there’s a certain amount of skills that I have to understand why you would want to buy it.And other things like that. But then me. Getting you to go to a website and buy the same thing without me talking to you when there’s real leverage in that, because now like a thousand people or one person could read the website and it works the same either way, but it’s really hard. Like that is a whole skill in building trust and copywriting and understanding and all of that.And so when you’re like, I’m going to go from a client work to a SAS application, there’s like a thousand of those skills. You know, there’s probably actually like 50, if we’re gonna break it down, you know? But,Eric: [00:16:48]It feels like a thousand. Yeah.Nathan: [00:16:50]Yeah. It feels like a thousand and that’s why like it’s so insurmountable.And if you want to try to learn all of those things in a single step, you, you can, there’s plenty of people who do it, but then don’t be surprised them that step, instead of you’re like, Oh, it should only take six months. and it takes six years instead, like, just know that because there were six years worth of lessons that you chose to do in one step. Whereas other people chose to do it in incremental.Eric: [00:17:15]Yeah. And, and in my experience has been that each kind of, one of those steps is gives you increasing resources and confidence and skills to like, know that you’re, that like the next one is in reach. Right. I actually use your ladders of wealth creation as an example in the book it’s like, of course the laboratories, it’s a very similar kind of framework to like, Hey, look, leverage is like this big, important idea.And it’s going to define your life. If you let it in the same way that compounding can, but one, you have to be willing to start small and be patient, but look at how we can connect the dots going forward. but you do have to. Respect to the idea and kind of pay homage to it in each little decision that you make for years before you start to see that payoff, just like compounding.I like that. It’s a painful, you watch that graph for so long. Look really flat until it takes off. And when you can layer, actually have some like graphs in the, in the course that show like, You know, here’s the margin of a book. Here’s the margin of a course. Here’s the margin. And when you layer these products onto each other, with increasing skill and increasing leverage in each one, the top of the graph looks exponential, but you can break it down into like what’s actually stacked up on top of itself.And it’s this very similar idea to ladders and wealth creation.Nathan: [00:18:38]Yeah, that that really resonates. And I think one thing that you reminded me of in there is like the leverage of relationships, because it takes so many relationships to build the SAS company. You know, not only in who you need to, like you’re talking about, you know, the cat, like, human leverage, you know, like getting wrangling a whole bunch of people and getting them to go in, in a single direction.You know, if you have relationships and reputation, that’s so much easier to do. And, you know, and see if you’re jumping right into that, people are like, no, I don’t want to come and work for you for less money for, you know, any of these things. I don’t even want to work for you for more money. No. You know?But in. In compounding reputation, from like the first, you know, the first of all iPhone app. So the book, so the building audience, then when it comes time to do this thing, you know, I hate when you buy this, people are like, Oh, I trust you from this. Like, I was just having a conversation with, Justin Jackson, over Twitter DMS.And so he’s the founder of transistor, who we used to host this podcast and doing amazing things. He’s actually the longest running, paying customer of ConvertKit. And I know him, you know, from like, blogging’s like that whole world, you know, it nine years ago. and like that relationship has been super valuable, I think for both of us, but it started. You know, way back here and isnow, you know, valuable to both of us as we run software companies. So I’m curious for you, like what’s your take on, on relationships and how those play into leverage and compounding.Eric: [00:20:16]Naval originally called it labor leverage, and I think I’ve reframed it as people because I think that’s so like, what you said is exactly true and people leverage is so much broader than labor, right? Like if you, if you’re stuckNathan: [00:20:27]Labor implies that, like I founded Walmart and now I’ve got a hundredEric: [00:20:31]Yeah.That is permission that I’m compensating people directly, that it’s like all or nothing that it’s, you know, you just kind of have that image of like people, you know, dragging stones around building the period pyramids. And you’re like today, People leverage, it looks much more like a network of kind of trusted, like high credibility people.It looks more like an audience. and that’s not, it’s not compensated leverage, right? Like some of those influential, like highly leveraged people on earth are just people with big fan bases. And that’s all kind of like double opt in. People are expressing themselves through their dedication to a person and an artist, you know, a writer, a musician, Or so there’s the, there’s kind of like the audience fan base.And then there’s the, kind of what you’re alluding to though, like friendship, credibility, network support, and then, then all the team and people that actually like who skills and vision and belief you need to kind of. Build a product that takes more than one person’s skillset. you know, we talked about building those 50 skills, but like practically what happens is, you know, you build 10 or 15 and you find other people with 10 or 15 and you kind of combine them into like, Hey, I’ve got this credibility and this experience and this audience and this product idea.And they’re like, Oh great. I have this engineering expertise in this, you know, this credibility and I can build a team and I can make architecture decisions. And somebody else comes in with like, You know, some, some Content expertise and like those, you, you are all, each other’s leverage. Like that’s the other thing that people want, which is like, leverage is a little bit of a.There’s this connotation that it’s like to get leverage over somebody like the mafia kind of leverage. and I think that some people will kind of hear people leverage and they’re like, Oh, I don’t like it. which is totally fair. Like this is not about coercion or persuasion or anything. This is about like, we are all using each other’s skills and expertise.And like, you know, you are writing a book to serve your readers. They are buying a book to serve, you know, to reward you for that. And like they’re getting 10 years of your experience. For $40, like that’s a bargain of a lifetime. so there there’s a lot of, you know, I think we need to get comfortable with that.You know, we’re all, we’re all serving somebody. We’re all somebody’s customer. We’re all, you know, somebody’s, somebody’s chef somebody somebody’s waiter, somebody Writer, somebody entertainer like.Nathan: [00:22:57]Yeah. And I think. Even on the relationship side of having the ability to email someone, and then, you know, have them say like, yes, I’ll make an introduction to this person or, or like you and I have built leverage in like personal brands where in both ways, right. I’m emailing you and say, Hey, will you come on my podcast because I’m a fan of your work.And you’re saying like, yes, I would love to come on your podcast. Cause I’m also a fan of your work.Eric: [00:23:24]I’m a fan of your work. Yeah, exactly.Nathan: [00:23:26]You know, and so that’s because we’ve both built leverage in those areas from like ultimately, but started with writing and teaching and, you know, in some way, and then that just compounding over time.Eric: [00:23:37]Yeah. And there’s no, one of the questions I get from people is like, do I have to like go be a public internet person in order to like, build leverage? and I know Lisa, like the short answer, I think there’s, you know, every, like, Industry probably has their own version of this. Like you still have reputation yourself, credibility, you still have network.You know, you don’t have to be out there writing blog posts in order to build, leverage through network and friendships and experience and, all those things. Although there is a unique dynamics to like an uncapped audience, like worldwide audience, that I think is worth people paying attention to.Nathan: [00:24:14]What are some of those other things? Right. So if someone’s saying I don’t want to be. The public internet person, which I think is something that people wrestle with a lot, especially today, as you see it, like it’s always been a really high upside thing, but we’re also seeing, like, it can be fairly high downside, you know, especially if you don’t have, a thick skin or, you know, like if you, you, there’s more to lose now.There was always a lot, but I think maybe there’s more examples of, the negative side of things.I’m curious. What other types of leverage you would point people to when they’re thinking of like, I don’t like the whole audience blogging podcasting thing, like I’ll stay as a reader, listener things.Eric: [00:24:55]Yeah. I think so. There’s, there’s definitely there’s people who are increasingly doing it anonymously. so there’s, you know, there’s, there’s the pseudonym, there’s the anonymous route.Nathan: [00:25:05]What do you think about that?Eric: [00:25:06]I support it. I support it.Nathan: [00:25:07]Yeah. Would you have, like, have you considered doing it yourself of like, as you, you know, spinning up?Eric: [00:25:13]Yeah. Yeah. I’ve always, I’ve always thought about like, if you had to just like drop a match and like get rid of your identity and like start over tomorrow anonymously, like what would it be like, how would you do it? What could you do? Like, I think that was like a fun mental exercise. And then people were doing, I saw some, I saw, I don’t know if it was a guy actually tweet the other day.He’s like, I just like abandoned my public persona with 30,000 followers and like started over with an anonymous account. And like, I’ll never tell you who I was, but like, here we go on while you’re unplugging and plugging it back in. and I think for some people that’s like, I think it will be increasingly common in the crypto world.Like we’re we can see a bunch of that already. I mean, there’s like. Anonymous accounts at the head of like a billion dollar Dow, treasury, like that’s crazy. but makes sense. It’s also like I was, I was thinking about this earlier. There’s like, have you read the sovereign individual and like all of the logic of violence and it’s like a very fashionable will kind of like crypto book to read.It basically says like the logic of violence determines the structure of society. and you can kind of get into this thing where like, if. No one knows who you are. Like the safest thing you can be as anonymous, in a world where like anybody could show up at your house at any time. Like the safest thing to do is just have nobody know who you are and where you are.Because if they know you’re in control of a billion dollar Dow, treasury, that’s not a good thing like this, like there’s no physical thing that can protect you or as much more expensive than just being digitally anonymous and untrackable. to the extent that you can. So I think there’ll be increasingly common.I think like it’s a very simple solution to kind of like workplace equity and fairness is just like your, your track record is associated with a pseudonym. not, not a real world identity or name or photo and like, that’s fine. I would have no problem hiring anonymous people. I kind of do it accidentally online already through marketplaces.Right. I don’t know if the person I hire on Upwork. Is that real name or no, there’s a real photo. Like I just know that they have a bunch of good reviews and I pay them to do the work and they do it. And that’s great.Nathan: [00:27:33]It’s interesting to think about. Like people doing that with audiences. And there’s plenty of examples that we’ve come to, like, you know, a Twitter account, like Ram capital or, or, you know, there’s, there’s plenty of them.And I don’t think it really holds you back. Like, in some ways, I wonder if it’s speed things like speeds up audience growth or, or leverage in some of those ways. So, okay. Ways it’s harder, right? I can’t be like, Hey Eric, Hey, you know, David who like texted a bunch of friends and be like,Eric: [00:28:05]Yeah.Nathan: [00:28:06]Wrote this post, will you promote it? That kind of thing.Eric: [00:28:08]For, for people who are yeah. Starting from zero without those friends and connections, it’s probably, that was probably a wash. but it’s definitely a challenge if you already have them. I think it’s a little harder to trust somebody. Like, it takes me a little bit longer to build a mental model of an anonymous.Person. but you can mean advantages. You can build a brand that’s much more extreme than a real world person is willing to be.Nathan: [00:28:37]Right,Eric: [00:28:38]I don’t know, there’s always been like a joke accounts that are justNathan: [00:28:42]Right.Eric: [00:28:43]Things. th that tend to grow really quickly,Nathan: [00:28:46]What was the, like, in the, start of space? Fake Grimlock.Eric: [00:28:50]Yeah, that’s what I was thinking. That that’s the name I was trying to come up with. Yeah. The like caps lock, dinosaur monster guy. I mean, startup startup called Jackson was a really famous one. yeah. And it’s like those accounts build credibility, like huge credibility. and I think, I don’t know, I don’t have a good example off the top of my head of somebody who’s like turned that into a really big business, but like, I think there’s plenty of people doing, doing great through anonymous accounts.Nathan: [00:29:16]Yeah. It’s interesting. Once it probably is harder to get traction in some ways, but then what you’re talking about of being able to take strong stances, you know, the internet, both rewards and punishes. Strong stances. Like if you’re out here going, like, you know, leverage is, is, is nice. Like if you can get it, I don’t, know.You don’t, you’re like all soft about it. No, one’s going to pay any attention. But if you’re like, Hey, this is a thing you have to understand. Here’s why it matters. And all of thatEric: [00:29:40]Yeah.Nathan: [00:29:41]But they’ll really pay attention. They’ll read the posts, they’ll share it.Eric: [00:29:44]So that’s a thing I’m like, that’s a card I’m pretty unwilling to play because I’m like a normal person who wants to actually represent myself as a normal person online. And like, it is pretty. I think it’s kind of trivially easy to win the like outrage retweet game. And there’s people who just like tweet hot takes in deliberately clumsy ways to like, get the reach of people, like quote tweeting and like dunking on them.But like all the time they’re getting more followers and people show up to defend them. And I’m just like unwilling to do that, even though it clearly obviously like works for gaining a bunch of followers. but like if you were to set off at a, as an anonymous account to do that, like easy, right.Nothing to lose. That’s your brand from the beginning.Nathan: [00:30:27]Okay. So we were, before we went off the anonymous direction, we, we were talking about, like other types of leverage that, you know, isn’t relying on, on that audience or reputation.Eric: [00:30:38]Product is leveraged and a very common like starting place. Right? So anything you can record, you know, at the end of the course, I kind of try to codify these like 10 laws of leverage. That’s like these little triggers to like remind you and like turn this into instinctive behaviors.And one of them is don’t repeat yourself, record yourself. So when you hear yourself telling the same story over and over again, you should be writing it down. You should be recording it as a video you should do as a Podcast, you should, whatever. And I think it’s easy to underestimate the power of like creating something that can serve hundreds or thousands of people in parallel and into the future.And like, you know, people will make a YouTube video and it only gets like a hundred views and they’re kinda like bummed about it. I was like, Like do the math on that, like ROI, like that is a miracle. Like if a hundred people listen to this podcast probably way more are going to, but if a hundred people listen to this podcast from one hour of our time, like, That’s a crazy miracle that couldn’t possibly have happened a hundred people in a room and I’d be like sweating, but like 5,000 people are going to listen to this.And that’s absolutely wild. so think like product leverage at almost any scale is like a miracle that we see every day that we’ve just forgotten is a miracle. and. When you are prolific with that, even if you don’t like you get good at it fast, and that leverage has its own kind of compounding, in, in, in a way being prolific is like its own form of credibility.Like you make a thousand podcasts, like you’re probably not going to suck by your thousands Podcast, no matter how slowly you improve, you just can’t not get better.Nathan: [00:32:23]What makes Seth Godin has this thing that he says, like, I will come on anyone’s Podcast. You just have to have recorded at least a hundred episodes. You know, and partially cause he’s going to, like, I want you, I want to make sure that you’re consistent with it. I don’t wanna be your third guest on your fifth guest.You know, like most Podcast die after, you know, probably three episodes. and so he’s like saying, I want to help you, you know, I like encourage that, but like here’s the bar that you have to get to. And hopefully you won’t be a terrible interviewer by the time you get to a hundred episodes, you know?Eric: [00:32:54]Yeah.Nathan: [00:32:54]Credibility and, and all of that, that comes with being prolific.Eric: [00:32:58]Yeah, that’s a great rule. And then you’re not evaluating it, then you’re not thinking about it, then there’s going to be, there’s certain to be like some sort of guaranteed minimum audience, probably by the time they get to a hundred episodes. yeah, that’s, that’s really smart.Nathan: [00:33:10]Something else, on productizing level or product as a leverage side of things that maybe it made me think of is we have a internal Podcast for that ConvertKit team. that is each team member being interviewed about their life story. by another team member. And so you’re like outgoing on your run.And you’re thinking about like Charlie, who’s our creative director and you’re like listening to her life story. And so there’s a bunch of, she records that once, for an hour, you know, and then now the 67 other people on the team, and then everyone who joins from today. Forward, like listens to that. And then now when I sit down or anyone sits down and talks to Charlie, then it’s just like, Oh, tell me about growing up in Brunei.And like this whole thing, like, we can shortcut so much for that becauseEric: [00:34:01]Yeah.Nathan: [00:34:01]story and she’s listened to mine. And like, weEric: [00:34:05]That’s as a brilliant application, as a brilliant, there’s so many, like so many. Onboarding’s have the like, Oh, like go get coffee with the whole team. And so like that just breaks so fast. As soon as you have like an onboarding class of five as like what, I’ve five coffees this week. Like I’m going to spend 10 hours, likeNathan: [00:34:22]Yeah.Eric: [00:34:23]hanging out with new members of the team every week.But that’s brilliant. And then you can just kind of wait until you’re like, Oh, I have my first meeting with Charlie next week. like I better. Go get some contacts and they hear what it’s like. Yeah. Listen to her episode, hear what it’s like to meet her here, like where she’s coming from, what she does here, what her goal is. That’s super, really, I love that.Nathan: [00:34:43]You said there’s 10 rules, or like the key things that you reminding people of? What are a few others of this.Eric: [00:34:49]Oh, okay. so one I have, that’s like the one I probably have to tell myself the most often, is, is do the things only you can do. I find myself like do the work only you can do is a really good way to remind yourself, like, what’s my highest invest use, how much stuff am I doing that? Like, Either doesn’t need to be done.Someone else can do for me, or could be automated, could be, you know, delegated, whatever. that one is, I catch myself doing that a lot. and then sometimes I’m like, no, I’m kind of enjoying this. Like, I’m good. Like, I’m fine with that. but usually the stuff that only you can do, is the highest impact, like.Longest term outcome stuff. It’s usually like talking to customers, giving, like creating a new sort of standard operating procedure, like figuring out, you know, some sort of high leverage like cops situation, which is speaking of, I have listened to maybe two or three separate interviews about your profit sharing system.And I absolutely adore it. I think it’s brilliant. I love kind of collecting the stories of like Nucor steel and Glen.Nathan: [00:36:02]yeah.Eric: [00:36:03]I feel like you are. In that lineage in a amazing way.Nathan: [00:36:06]Well, thanks. We’ll, we’ll give it some time to see how it all plays out, but those are also the kinds of stories that I, that I like to collect. I’m curious in the, in like the collection of stories, side of things, like what are some of the stories, like favorite examples of stories of leverage, you know, or in different types of leverage, applied that are your go-to.Eric: [00:36:26]I think, I really like this like example of, real estate agents. So I worked with real estate agents a lot over the last few years, and I kind of like Naval uses them as an example in the book of just being a high leverage job because your inputs and your outputs are disconnected. Most realtors are not actually it’s.Using that like, they’re not actually adding leverage, but the ability is there for any of them to add it. if they, if they choose it’s really independent contracting sales job, right. and most sales jobs have, this is just, everybody can relate to realtor. So one, one lesson I have in the course takes like realtors, four different realtors that are operating from like the first one is just like a very normal, basic, you know, Linear sort of time and money relationships.She does like 10 clients a year. It makes 50,000 a year. Okay. Normal, normal day job. The like best realtor in a typical office makes like. $400,000 a year. and it’s usually because they have like a full-time personal assistant or to the transaction coordinator. They’re usually spending money on advertising.They’re usually spending money on, tools like upgraded tools and systems. and they have like enough of a, more speaking of like opt in people leverage. They have past clients who are driving word of mouth for them. so like that is a really. That is a high leverage thing that people don’t think of as leverage, because it’s not labor is not even really audience.It’s just like happy customer base. and then you get into the order of magnitude above that, and you’ve got the realtor. Who’s like the number one realtor in the city. And they’ve got a team of 50 agents below them that are all doing the stuff that the best agents in the office are doing. They’re all paying for personal assistants, they’re all paying for marketing.And that person is like coaching and managing and recruiting all of those agents and building a team, a whole team of them in a culture that. Helps those agents become better and earns a percentage of all of their earnings. and this guy, I was wondering how far this went. And so I looked up, who’s the number one real estate agent in the country.And it’s this guy in Texas named Ben Cabalero caviar, I think is his name. And he started out as just like a normal realtor and he kind of found his way into this, like a niche of new home builders. And so he’s got now. this team, like, I don’t know a team dozens under him. And like half of them kind of work on these partnerships with new home builders who are companies that build like dozens to hundreds, to maybe thousands of homes per year.And they have to figure out how to sell them involved. And so they just don’t give him like here’s a thousand listings, like go sell all these houses. And then he’s got a software team that is building a platform to actually like manage the inventory of all these houses and all of their listings and all their sales.And then like, So he, he’s basically like a founder of a software company with a BD team and like designers and marketers and engineers, but he’s still functionally a realtor. And he earns commissions as a realtor on thousands of homes a year. And my napkin math is that this guy makes like a hundred million dollars a year.That could be like 50 million high or low, but like it’s crazy either way. And is the ultimate illustration of like, if you add system, if you systematically add leverage. Is of these four types. You can go from a very normal job, to an absolutely insane kind of like founder situation and the mindset and the instinct to like add leverage where you can and in a safe kind of, sustainable way.That’s manageable. Like. Is a huge, huge difference. You have to find your way into a place where you don’t have that ceiling and you can reinvest in that leverage and like you get the benefits of that. and there’s a lot of traps or places where that’s not as true. but if you can find that place and you can develop that mindset and like get into it as a habit and then go for, you know, 10 or 20 years, you can get to some crazy, crazy places.Nathan: [00:40:32]Yeah, it’s not that leverage plus compounding, but the two of them together, pretty powerful. You have another tweet, You talked about blockbuster. he’s a Netflix didn’t kill blockbuster being over leveraged, killed blockbuster. I’m curious some of the, like the downsides of leverage or people misuse it or, yeah, don’t understand what they’re flying with it.Eric: [00:40:55]Yeah, yeah. Leverage. I mean the lever goes both ways, right? Like leverage pushback. and that’s actually like, so leverage law eight and nine levers. A lot of our aid is live by the lever.by the lever. Like if this is the game you choose to play, like understand that it can hurt you. and levers a lot.Number nine is like leave room for things to go wrong. which is just kind of the like normal. Peterson way that all the investing nerds would say margin for margin of error. but there’s a difference between being over leveraged and being super leveraged. So like you can have really, really long levers, right?Like Warren buffet has a really long letters. he’s got billions of dollars. He’s got multiple many companies. He’s got, you know, 250,000 employees. but if those levers push back on him, they’re not dangerous amounts of large and he can. Absorb that pushback, kind of with equanimity, because it’s not just because this long does it mean the travel is high and doesn’t mean there’s like a huge force pushing on the other side.And so there are people who, you know, if you make $50 an hour and you hire an assistant for $40 an hour, And try to outsource your whole job and then like, there’s no room for things to go wrong. And if there’s pushback on that other side of that lever, you know, your revenue changes, your costs, change.Something happens like all of a sudden you’re in deep shit because that lever is pushed back too hard on you. You don’t have the like capacity to absorb that blow. and now all of a sudden this is like launch you into space and, and you’re done.Nathan: [00:42:31]Gross margin matters. When you’reEric: [00:42:33]Yeah.Nathan: [00:42:34]how, like, to what degree you can use leverageEric: [00:42:37]And, and as you layer things on top, right? Like if you’re making a hundred dollars an hour and $10 an hour system makes a ton of sense, but if you hire five of them like that stacks. And so all of a sudden, so like you’ve got to run the math and, and be cognizant of all the other levers, things like product leverage.Like we talked about the risk of being. Public person. And so like, that’s less quantitative, but it’s still intangible and it’s still a form of risk. but you can layer a lot of those on top of each other before you have like financial risk associated with that. but that’s not true, you know, when you’re, when you’re playing like leverage trading games and like, you know, I’ve, I’ve seen plenty of people lose way more money than they thought was possible because they were using leverage that they did not understand.And when those good. Multiplied out, things can move really quickly. and leverage, leverage just gets you more of what you’re already getting. It doesn’t change your outcome. So like, if things are going poorly and you add a bunch of money to it and make things happen poorly, faster, and more often than like you have not done yourself, any favors, except that maybe we make it more clear.What were you were already getting? so yeah, it’s a very, I, you know, I say to anybody, who’s thinking about the course, like this is not for people who do not know. What they’re doing, or do not, are confident in the direction that they’re heading and are confident, like investing money to get more of the results that are already getting.Nathan: [00:44:05]yep.Eric: [00:44:06]Is for like, getting more of what you’re already getting.Nathan: [00:44:08]Yeah, that makes a lot of sense. somebody else that I want to turn to talk to a bit is the, the book, the Almanac of involve Africa, which is, has replaced, well first rework, and then anything you want as my most gifted books. so thanks for, thanks for writing that. it’s just one of those things where I’m like talking to someone, whether it’s a sibling or a friend or someone else I’m like.This will change your world. Know like it is the most condensed way I can get them to think in a completely different way. So thank you for doing all of the work to, to put that together. I’m curious how that started. like, what, what inspired that project and then how did you start working on it?Eric: [00:44:51]Yeah. I mean that, the inspiration came really from a podcast that navel did with Shane Parrish. on the knowledge project, it was an awesome interview. I listened to it two or three times. and I was a little, like I’d been following them all for 10 years, right? Like, since 2009, maybe when he like, started writing on venture hacks, there’s really still an awesome blog.I’ve been following him and learning all these, you know, what are used, mostly talking about startups and investing for a long time. And this interview with Shane Parrish was the first time he kind of talked about like some of his, some of his like principles for how to build wealth and some of his principles that he had been like kind of teaching himself about the philosophies and practice and habits of happiness and building happiness, and that you are totally in control of your own happiness.And I thought this was such a good Podcast. And I love podcasts. I listen to them a lot, but I’m also very aware that like, most people don’t listen to podcasts and even if they do the discovery is not great of whole episodes or even within them. And I just thought it was such a tragedy that most of the stuff that of all is shared on Twitter and in Podcast is just in such a like difficult to access kind of subcultural like ephemeral format.And I spent. I mean, I’m, I’m, I’ve been curating and assembling and editing and writing for a long time. And, it was kind of between projects. I was like, all right, I’m going to go like, Just throw this idea out there. and I was like, you know, I saw the tweet is so dumb and I just thought up a Twitter poll is like, if I wrote the book of knowledge and like compiled a few of his important transcripts, like, do you want that?And like treated it and went to bed. And I woke up to find that Naval had retweeted it and like, you know, 5,000 people were like, Oh my God, yes, please do this. And Naval was like, I’m not gonna provide you all the materials, like rock on. And I, I don’t have any reasonably that he knew who I was. I had no connection or, kind of prior access or anything like that.And, I mean, he gave me an export of his whole Twitter history and everything else was public record. I just started doing transcripts of the podcasts and interviews and books and, just kind of like threw it all on the table. It was like, all right, let me like start kind of. Learning to condense this and makes sense of it.And I mean, it was well over a million words of source material that I just kind of like started organizing and distilling and lumping into ideas and categories. And, I just, I mean, I was excited to like swim around and all these ideas and like absorb them and learn them. And. spend time like reading and rereading and just do this giant, like weird conceptual jigsaw puzzle and make it easy for people to read and get these ideas in their own head and put it into a format that would last for, you know, hopefully decades and be relevant for people for a long time.Nathan: [00:47:30]I didn’t realize how early in the project didn’t have all got involved or like, you know,Eric: [00:47:35]Yeah.Nathan: [00:47:36]gave his blessing. That’s pretty cool,Eric: [00:47:37]Yeah. I mean, he’s got, I have no idea. He was probably like, yeah, sure. Go for it. Like there’s no chance you’re actually gonna finish it. I I’ve, I have no idea. but he’s, he’s pretty like, you know, and then we, we kind of came to terms he’s like, make sure there’s a, you know, free version available for everybody and, make sure that it’s clear that like I’m not selling it.And not earning money from it. because it would be critical to some of the material that’s in the book and all like done and done, like. Let’s go and it took me three years to finish it and publish it, but it’s, we got out there and I’m really, I’m proud of it. And I think it’s a really, I like, I really enjoy hearing that people got a lot out of it.I wish I’d had it at 18. but the next best thing is, you know, making sure that the next next generation can have it and are better educated than we were. soNathan: [00:48:27]right?Eric: [00:48:28]we all end up better off in the future, you know?Nathan: [00:48:29]Yeah. What are some of those other cool things that have come from it? You know, maybe unexpected you go from, I’m gonna throw out this random tweet and go to bed and then fast forward a few years and you’re like, okay. This, you know, this thing happened And, it’s because of what ultimately started with a tweet after it podcast episode.Eric: [00:48:45]Yeah. I mean, it’s, it’s a thousand little things, you know? just like getting DMS for people that are like, you know, I gave this to my 18 year old brother and like, it totally changed his life. people who are like actually made me drop out of law school and like go become a software engineer because I didn’t.I didn’t understand why technology was going to be so key. And, it’s just, it’s really interesting to hear, you know, it’s a bunch of individual stories, I think, you know, it’s been cool to like kind of come on podcasts and talk to people and meet them. And, I’m really excited about, this format.Like I think there’s so much valuable stuff that’s created in a femoral digital mediums, and I think books just will always have a place. And, and that kind of transformation and that, that practice of curating things into like something really timeless and taking somebody’s whole body of work. And.Turning that into, like this has always been my favorite genre of book, right? Like I love Peter Beth Mullins books, and I love Porcelli’s Almanac and the letters of Warren buffet and, like principles. I think, like it’s not, everybody’s going to sit down and write their own book and dedicate years to doing it.But I think the ability to kind of like condense someone’s best advice and worldview and things into, into a book that someone can read in a few hours and like really get the experience of a lifetime. Is really cool and valuable, and I hope we see more of those. I certainly intend to keep, keep doing them.Nathan: [00:50:21]Yeah. Yeah, that’s great. is there something that you’re working onEric: [00:50:24]not, not that I can talk about yet, but,Nathan: [00:50:26]yeah,Eric: [00:50:27]Yeah, I got it. I got a new spreadsheet. I’m working on it.Nathan: [00:50:31]I know they’re new million words of source material out there.Eric: [00:50:33]Yes. Yes. I know there are New million ways.Nathan: [00:50:35]That’s not intimidating at all.Any numbers that you can share from like the book launch or something like that? I’m always curious how, like the scale of something like this, especially when it has the free version. And so even in the number of people who read it or anything like that?Eric: [00:50:51]Yeah. I mean, we have like the site, the page views on the site are, are like, I think, well into the millions now. or somewhere in the mid six figures for, I think like digital downloads, that’s harder to track, but it’s like,Nathan: [00:51:09]Yeah.Eric: [00:51:10]Yeah. It’s a lot.Nathan: [00:51:11]And then I assume a substantial number of people going like, no, I don’t want the digital version. Like, I’ll take the, you know,Eric: [00:51:17]Yeah.Nathan: [00:51:18]like, I think I’ve bought eight or 10 copies of the book.Eric: [00:51:23]Yeah. Impossible. The answer is like what the effect the net effect has been like, does the free version drive more sales? Like, I’ve definitely have heard stories of people. Like I read the free version and it was a few chapters in and the like, then I went and bought the physical version or finished the free version.I loved it. And so like, I wanted it as a trophy, a physical version, or they read it and then they gift it or like, whatever. so yeah, it’s, it’s impossible to know, I think, but like, you know, my goal for this was just like, Please. I hope it gets back to cash that I put into like making it professional and like well-designed and well-published and, it has done that and more.Nathan: [00:52:02]Right.Eric: [00:52:03]You know, Naval seems happy with it as a like representation of, of him.Nathan: [00:52:10]Have there been like, did it result in more conversations in interaction with evolve over time or has he been pretty much like thumbs up from a distance?Eric: [00:52:19]Like, you know, we, we actually never spoke live about this. Like we did it all through email. I kind of kept them updated and he was kinda like, cool, let’s go ahead and like, as comprehensive, as that’s a lot, like yeah. yeah, so, no, I appreciate, I mean he was, his support has been like.Super super valuable. And I’m actually not sure that I would have felt good about doing it because like, there’s this huge risk of kind of like putting words in his mouth. and in opening him up to misinterpretation by just like recontextualizing all of this stuff, which is kind of like what I’m doing by definition.So it’s, it took a lot of faith I think. and I, I appreciate the kind of trust he put in me there to do it. and yeah, I’m glad to see it’s, you know, if I can, I can be positive, like a piece of people finding their way to him and understanding that better. Like that’s, that’s awesome.Nathan: [00:53:20]Yeah, that’s great. And I’m excited for more of that format, because like you said, there’s a lot of people who have this like wealth of knowledge and, and Content, but it’s not like packaged nicely that I can either read myself or like give to my brother or anything like that.Eric: [00:53:35]I can’t wait to do the Almanac of Nathan Berry.Nathan: [00:53:37]Yeah. hopefully I’ll be one of those people that like writes it all down myself rather than me, you know, but I’d be down, Yeah, well, I’m, I’m curious, like as we, as we wrap up, where should, well, first, what are you working on most right now?And then where should people go to, to follow you?Eric: [00:53:55]Yeah. My main project right now is a course on leverage. So, this is, this is all very top of mind for me. The biggest question I get from the books, people who read the leverage chapter and are kind of like, that’s awesome. I totally get the importance of this idea but, I don’t know how to apply it to my life.So I kind of have been really distilling frameworks and ideas and collecting stories and like putting them all in this course, that will launch soon. And it’s kind of like quietly in beta, letting people in as we get confident that like we got, the right kind of level of fidelity and things here.So, that’s, that’s a huge focus for me right now. I’m really excited to be like building my first course and like getting to kind of put my hat in this ring of education. And I think, I really am enjoying experimenting with like, I want to provide the flexibility and availability and like kind of perfectly available, of, of asynchronous, like evergreen course with a layer of kind of very light accountability and social connections, and community that comes with it.So I’m trying to pull the very best of like a high-end very expensive cohort-based course and, like, permanently available kind of course and like merge them into one here. So it’s a little bit of experiment in medium and like getting to explore this topic that I really like. so that’s really cool.That’s on my website: ejorgenson.com, And, I spend like way too much time on Twitter. So, if anybody wants to come hang out with me, like I’m easy to find.Nathan: [00:55:29]Sounds good. Well, thanks for coming on. We’ll both had our separate ways. We’ve got stuff going on this evening, but, it was good to catch up and I’m excited to see the course come to life.Eric: [00:55:38]Yeah. Great to talk to you. I can’t wait to, to flip the mix and, have you on my podcasts and, get to dive into more of the story. I think, I think you’re going to be a perfect, like exemplar case study of intuition of leverage and building that ladder. And I can’t wait to dig into it.Nathan: [00:55:54]I love it. All right. We’ll chat soon.Eric: [00:55:56]All right.

Steph Smith is a growth marketer, writer, and indie maker. In 2019, Steph founded Integral Labs. Integral Labs supports top tech companies with technical writing, content strategy, marketing, and analytics.In 2020, Steph became the Senior Manger of Trends.co. Trends identifies emerging patterns in business months before they become mainstream. In less than a year, Steph grew the number of paying subscribers by more than 400%.In this episode, Nathan and Steph discuss her proven approach to starting and running a profitable newsletter. They cover everything from pricing models to avoiding burnout.Topics from the show include: How to price your newsletter for explosive growth The best pricing model for dramatically reducing churn How to make your newsletter stand head and shoulders above the rest Links & Resources Trends.co TheHustle.co Sam Parr Twitter 030: Sam Parr – Growing to 2M Subscribers and Selling Your Newsletter Wolfram Alpha ahrefs JungleScout Keywords Everywhere My First Million Podcast Toptal 3-2-1 Newsletter Exponential View Guest’s Links Personal site: stephsmith.io Steph’s Twitter: @stephsmithio Episode TranscriptSteph: [00:00:00]Once you actually take the energy to write an idea down and it’s implanted into your brain, almost like a seed, it starts to grow and you start to notice other things around you that are aligned with watering that seed with different examples, with intentional research, with data, by the time you actually want to write about it or publish it, or even start a business around it, you’ve thought about it in many different ways and giving it time to breathe.Nathan: [00:00:28]Today’s episode has been Steph Smith who runs trends.co, which is the paid newsletter from The Hustle. So, they have their 2 million subscribers newsletter and they have their paid newsletter called Trends, which is a little smaller, but drives a ton of revenue. This is super interesting. We get into her approach to growth, to research, she’s actually a chemical engineer who turned into this whole world. So, it’s super fascinating; she’s got a bunch of tips and tricks that she shares around doing research. I love her thoughts on differentiating products. There’s so much more; she gets into business models, everything. She’s one of those people who’s basically running the show at one of the largest paid newsletters. She’s incredible. So anyway, I’ll get out of the way let’s dive in and, made stuff.Steph. Thanks for joining me.Steph: [00:01:17]Yeah. Thanks for having me.Nathan: [00:01:18]Okay. So I’ve got to start with the question. what’s it like working for a crazy person and specifically, how are you so good at managing up? And before you answer this question, did in fact come from the crazy person that we’re talking about?Steph: [00:01:34]I didn’t see that question.Nathan: [00:01:37]And he’s like, Oh, I don’t know.But you got to find out like how, how she manages to deal on a day-to-day basis.Steph: [00:01:44]Well, I think we all are on a spectrum of being so good at executing. Some people are great at executing, and logistics, and processes and all that stuff. And some people are just visionaries and just have so many ideas and it’s crazy to work with them, but in a great way. If you can just give them the space to like, be that visionary and not necessarily depend on them for certain things like processes and logistics.And so I’ve just learned over time to not necessarily bucket people, but understand what they’re great at and maybe what they’re not so great at. And Sam loves hiring operators. And he he’s hired CEOs or presidents to work alongside him. So I actually think one of the great things about working with Sam is how self self-aware he is because sometimes visionaries or people who are like the idea guy don’t realize that perhaps they’re not so great at some of the other things.And so I just like to give Sam the space to give his ideas and be the visionary. And it’s funny. Cause sometimes when people first start working with Sam, they’re like, Oh my God, he has so many ideas. Do I have to do all this stuff? And Sam will tell you like, no, don’t do all the things I say.I just love sharing these ideas and getting things out there, but you have to decide what’s important, what should be prioritized. And so I do think it was a little bit of a learning curve, but now I love working with him because he does actually just give you the trust to make those decisions.Nathan: [00:03:03]Yeah, that’s interesting. I think so many people run into that and I’ve had the same thing with our team at ConvertKit where people are like, Okay, you said this, does this mean I need to start working on it? And you’re like, no, no,Steph: [00:03:14]Yeah.Nathan: [00:03:14]I was just talking and I’m not even as wild and crazy as Sam is on that spectrum. Sam’s off the charts, but it is a good differentiation.And maybe I shouldn’t be more extreme that way people would know that it’s not humanly possible to do all the ideas and to just ignore most of them.Steph: [00:03:32]Well, I mean, Sam will tell you, like right away that he’s just throwing ideas out there. And I think that’s really great because you’re just like, okay, so we’re on the same page. I know how much of this I need to pay attention to. And then he will explicitly say, which I think is also helpful, when he does want you to do something, versus some bosses or some people you work with, it is a little more muddy and it’s hard to tell what’s important. What’s not.Nathan: [00:03:56]Yeah. That makes sense. Another thing that Sam was talking about that he wanted you to share more with listeners is, your process around organization and creativity. I imagine at The Hustle, there’s so much going on. There’s tons of content going into the newsletter side, that Trends side, everything.And, I’d love to hear more about your process for keeping all that straight, making sure you’ve got nonstop deadlines, crazy ideas. And what do you use for organization? Like maybe somewhat on tools, but even more so like.Steph: [00:04:36]Yeah. So I think so I will candidly say that on that spectrum where there’s people who are like incredible executor’s and organizers, I’m maybe a little further to that side than Sam, but like, there are people who are way more organized than I am and what I try to do to like orient myself. Cause I’m not like a task person or like a, a calendar person who’s super, super regimented is just to check in every.Like either every day or every week, and just make sure that you have like very, very clear priorities as to like, what would I be happy with at the end of this week, for example, like where would I feel like we’re actually moving towards something, and be okay with it if I did nothing else during that week, because I think it can be the case sometimes where we just get so lost in the weeds and we feel like we did so much, but then we look back and we’re like, the needle didn’t move at all.And in fact, I mean, I know burnout is a much more serious thing, but lately. Feel like some of my coworkers or other people I’ve worked with in the past will say that they’re burnt out. And honestly, a lot of the times they are. But one of the things that I’ve noticed is that sometimes people feel burnt out when they’re just working very hard and they don’t see that translate at all.Right? So it’s not even necessarily the degree that they’re working or, or the amount of time that they’re putting in, but it’s the lack of like a relationship between the amount of time that you’re putting in and then actual movement or progress. And that can be really defeating. whereas. I’ve seen, you know, people who work much harder, but don’t feel as like degraded because they feel like that movement.And so I’m not, again, I wish I could give better tools or processes or things like that, but I feel like everyone has their own thing. But one thing that keeps me like really motivated and really, excited about doing things and building things, is that feeling of progress.Nathan: [00:06:21]Yeah. I mean, that really resonates because there’s definitely times. You know, over the years of building ConvertKit and other, other projects where you’re like, I’m working the hardest I’ve ever worked. And it just doesn’t feel that hard because we’re getting results. And then other times you’re like, I don’t even necessarily putting in more time or it’s that much harder, but it’s just, it’s a slog because it doesn’t feel like it’s working.What do you think about like when you find yourself in that, that space of like, The inputs are not directly affecting the outputs, either from a mental side or process, like how do you, how do you handle that and get through it?Steph: [00:07:00]Yeah. So I think it’s, like I said, one just about like continuously revisiting what your priorities are and making sure that you’re like, if you imagine yourself as a vector, like how closely aligned is your vector and like your priority vector. Right. And sometimes they’re like, they’re always going to be a little off, but is it like.You know, perpendicular or actually aligned. and a lot of the things that we do, I tweeted about this recently, it’s just, just how much of your day is actually due to inertia versus like actual, like intentional thought of like, what do I, what do I really need to get done to reach my goals? so I think that’s something that we always just continuously need to check in on.But then the other thing is when you’re in that mental space where you’re really struggling and you’re not seeing progress is just to design really small wins for you. Right. Because another, another thing that I think people sometimes do is set really, really big goals, audacious goals, and that’s awesome.But then they don’t set up that. Building blocks on the way there. And so that can be again, really defeating to be like, I have this goal and I just don’t feel like I’m making any progress. And so if you find yourself in that head space, obviously take a break, do what you need to get in the right head space.But also just, one of the things that I think the most successful people do is understand the way their brain works and almost like learn to. To interact with their brain most effectively. And one of those things is finding those small wins. If people are interested in learning about the habit loop, for example, like one of the parts of the habit loop is like a reward, right?And so if you’re designing this audacious goal and you’re not spinning that habit loop of getting to that reward, you’re not, well actually, if you don’t have the reward, you’re never going to complete the habit loop. So I think it is just about learning about how your own brain works and getting those small wins along the way.Nathan: [00:08:42]Yeah. Are there small wins that you’ve introduced in your process of running trends that help you or, or are the big wins coming often enough that it doesn’t feel as needed?Steph: [00:08:54]That’s a good question, because it is different, like at different stages of each company that you’re working at, for trends, I think it, it really was about, at the beginning, just like. Creating something that people loved. Right? So that was a small one, like getting the newsletter out and just, you know, having people write to you and be like, I love this, or meeting people and finding out that they read trends and that, you know, they love the product.So at the beginning it was more of that. But then, you know, the small wins come with growing your user base and, and actually like unlocking a new channel right. Or something like that. But even on the way to unlocking a new channel, it’s like, The mini wins of like, how can I just like focus today on just this part of the landing page and running a test where I can get a small win.And I feel like I’m making progress, right? So it’s, you know, a small win can be anything from like, just getting a little piece of user feedback or actually seeing like a really tangible, but. Small change in your conversion rate, for example. but if you’re not seeing those small wins along the way, like the audacious goal is like grow trends to like X thousand subscribers.But if you’re not actually, you know, taking steps and reflecting on them, then that audacious goal is all of a sudden sounds actually like a crazy goal and you’re not motivated to actually reach it.Nathan: [00:10:05]Yeah. That’s interesting. Well, let’s dive in. But Simon can about trends in detail. And then maybe we’ll go back and, and talk through like how you got to The Hustle and Trent and all that. So can you tell the listeners, you know, what is trends and what, what makes it unique from other, you know, paid newsletters or communities and projects that it gets on it for?Steph: [00:10:24]Sure. Yeah. So trends is The Hustles premium subscription. And I always like to articulate how I remember at least Sam articulating trends to me, which is. You have The Hustle, which is our daily email of business and tech news. And The Hustle was always imagine your friend going and reading all of the tech and business needs for the day.And then coming back to you and just being like, here are the three, four things that you should know, no BS, no jargon, just like a friend talking to you. so that was The Hustle. And then the extension of that was like, okay, we have this audience of people who care about business and tech and trends was basically imagine that same friend going.I had five years, let’s say. And coming back to you and being like, this is what the future is like. Right. And it’s not even like the future as in like 40 years from now, like, this is what the new world will look like. It’s more so just like, Hey, here’s some things that you may be surprised to know emerge, you know, in a couple of years, or actually, if you knew this little.Tidbit or fact you could actually build a business around it that many other people haven’t caught on to. And so that’s what trends is. It’s basically, trends that people can learn about that are either like in the early stage or things that people can build businesses around, invest in businesses around. And it came at the beginning as a weekly newsletter, but now it’s a community and it has some other features.Nathan: [00:11:36]Yeah. And then how, how is it priced and, of the gels there.Steph: [00:11:40]Yeah, so it’s annual pricing, which is a little different than I think a lot of paid newsletters. and it’s $299 a year.Nathan: [00:11:48]why go annual on that versus, you know, someone wanting to sign up monthly? as so many people are like, I don’t know if they newsletter should be 20 bucks a month or 10 bucks a month,Steph: [00:11:56]Totally.Nathan: [00:11:57]I know it shouldn’t.Steph: [00:11:59]Yeah. So it’s interesting. And we are actually looking at toying around with the pricing model coming up, but it’s been that way since the very beginning. And I actually, I joined trends shortly after it started, but even by the time I joined, it was. Already just annual pricing, like set in stone.And I, I guess I can talk to a couple of reasons. Cause sometimes we get people who write in who are like, you must be predatory. And like, like why would you do annual pricing? If, if your product, if you were proud of your product or something like that. And there was a couple of reasons that people don’t think of all the time.So one of them is just, if you’re a bootstrap business that cashflow. Can actually accelerate your growth if you’re annual versus monthly, right? So you all, you get the year-long cashflow that you can reinvest into your business immediately, instead of waiting for that cashflow to come in. And therefore you can acquire more users, which is what we did.Right. We invested, we like every dollar we made, we reinvested immediately, which did accelerate our growth. there’s other things like sure. People might relate this to like the predatory aspect, but just churn. Right? So if you can really impress someone with your product immediately, They will pay for the two 99, be happy with it and not really mind that it goes around for a year, but when you have monthly pricing, there’s just that much more like, involvement of someone potentially thinking of turning, right?So they might love your product for three months and actually need it six months later. But in that time period, they may just cancel or you might lose them. And so. We have found that if you like equate an annual turn rate of ours to a monthly churn rate that most people have, our turn is so, so low. and so that’s helped us as well.It is definitely, negative in some ways. So people should know some of those aspects as well. Of course, some people two 99 just sounds like a lot, even though that’s only like $25 a month. That sounds like more for whatever reason. Right? So it can restrict people from buying your product. Of course, there’s just that like higher barrier to entry, but then there’s other things as well.Like a lot of people don’t know, especially because we have a trial that, even your credit card approval rates, like if people have heard of like dining flows and subscription payments, when you have that higher dollar value, you’re more likely to actually get rejected by banks. Even if someone’s approved it.So those are some of the things to keep in mind. But again, I was actually not even around when that final decision was made, but we are playing around with other models now. And in the next couple of months,Nathan: [00:14:17]Yeah. I think what a lot of people who get into paid content, I think like they see the appeal of SAS, right. Of I sold this ebook. I did this thing. You know how toWorkshop one-off would be amazing if that could recur. And, you know, look at SaaS, there’s a recurring revenue model there. So they dive into it and then are immediately shocked with churn of like, wait, no one told me that churn, like it doesn’t repair forever.You know, this is, and obviously people know about trend, but you don’t like you have to be in it before you understand the math of it, or likeSteph: [00:14:47]Exactly.Yeah. And if anyone’s thinking about whether they should even do opinions that are, and if they do meet monthly or annual, like you have to test it. Right. Because our business is going to be much different than others. And to your point, a lot of people think like, let’s just make this like, SAS, but think about what SaaS is.SAS is like, Oh, there’s actually this tool that someone’s like integrating into their business, that they need to continue running their business versus something like let’s be real most, Even premium content is, as people say, like a vitamin versus a painkiller. And so SaaS has such low turn rates because people are literally like implement, like integrating into their systems so that their people need it.They like require the software. And the only alternative is probably to switch to another piece of software, which has a lot of friction versus paid content is kind of like. I can either have this or I can actually be okay without this. Right. And so, that’s also something to keep in mind is it’s not the same business model.There’s, there’s like parallels, but you have to keep in mind that like paid content is not SAS.Nathan: [00:15:47]Yeah. And so having that advantage of going to an annual plan and even so many SAS companies, right. They push annual plans for the same reason because dropping churn is so key. And so. I think it’s a great point that the reminder once a month of like, here’s your receipt, here’s also, what’s coming up also.Do you want to cancel? You know, and, and then they’re judging it based on maybe not the experience as a whole of like, Oh, I got such great Content all of that months ago, it might be like, you know, the guests you have this month on transplant, it wasn’t that great.Steph: [00:16:17]Exactly right.Nathan: [00:16:18]But the guests we have the next week, the next month is like exactly who you need to hear from.And they may not know or…Steph: [00:16:25]Right. And tied to that. When you have a longer time horizon with your subscription, you can actually, I mean, we were bootstrapped, so this wasn’t quite true, but you, you can in theory have a longer horizon and improving your product, right. Because you’re not thinking about how do I retain someone tomorrow. It’s kind of similar to how people say, like public companies with their like quarterly earnings can be detrimental to their long-term success. if you’re focused on retaining someone next month, That can like cloud your vision to be like, what do we need to do to retain this person one year from now?Like that helps you to think a lot bigger about like, how can we improve this product really substantially by that time. and so that’s also something that I think is underrated about annual pricing.Nathan: [00:17:04]Yeah, that makes sense. So you’re in this world of, you know, you’re working on the paid newsletter side, with trends and The Hustle also has the, you know, the massive free newsletter running sponsorships. I’m all of that. So there’s different revenue streams. I’m curious for your take on the rise of newsletters over the last couple of years, and then the, well, these letters have been rising for a long time.Despite everyone saying email isdead. Every every step along the way. so maybe the rise of paid newsletters in particular and just sort of what’s your commentary on what you like, what you’re seeing in the market, and then what you would recommend as far as being in this world where you can see behind the scenes of, of both a sponsorship driven model and, and, you know, a paid subscriber.Steph: [00:17:46]Yeah, so I think there’s, again, not always a right answer, but what I would say is that, like you said, there’s a lot of hype right now around newsletters in general, but there’s also just a lot of hype around. Paid newsletters and getting your content. and that’s awesome because there are tools that have now enabled that and made it lot easier.But what I think people, or a lot of people miss when they’re deciding like free or paid, is that a lot of people who have paid newsletters had some sort of like awareness engine before that. And The Hustle was a great example where we had this massive newsletter reaching over a million people, such that.That was like, if you imagine a funnel that was the top of our funnel, right. And that was doing the work of like being easily shared and driving more people to trends every single day. What a lot of people I find do today is like, okay, like I want to start a paid newsletter. I want to start like making money immediately.And what they don’t realize is they’re putting their product behind a paywall and this might sound obvious, but that makes it that much harder to grow. Right. If you don’t have an, an awareness engine, how are you expecting that people are going to find your content. When it’s behind a paywall. and so you, if you actually look up.You can do this on Wolfram alpha and enter sub stack, in there. And you can look at their, their subdomains and how much traffic they get. So you can actually see exactly which sub stacks are the most popular. And I know sub stock has a page that does this as well, but you can see the exact number of page views actually, or at least will Wolfram’s, estimate of it.And if you look at them, most of them you’re like, Oh, that guy used to be a very famous reporter. Or this guy like has 400,000 followers on Twitter or whatever. And you’re like, Oh, okay. So it’s actually, you know, the, the story that they’re selling of like, you know, sort of paintings that are overnight and like be your own boss is great in some ways, but just know the reality that as soon as you get your Content, it becomes much harder to grow.And so what I tend to recommend if people are just starting out is to focus on. On free to start, like develop an audience and that’s their top of the funnel. And then some people later will either convert to paid or create a new product that’s paid or do something to monetize that audience at a later point.But I would focus if you have the runway to do so on a free audience. And of course you can monetize that free audience with other things like ads or. And donations or partnerships or things like that. So it’s not necessarily that you have to like, you know, Dr. a non-profitable business to start even cause The Hustle was profitable, Forte trends.So that’s the way that I view it. And, and another thing just on top of that is when people create any sort of. Paid newsletter or any sort of content is to kind of keep that vitamin painkiller model in mind. And that’s a spectrum as well. Right? Where if you think about it, trends really is more of a painkiller than The Hustle.The Hustle is news news is nice to have, but there’s so many outlets to get it, but getting access to information like trends that you can actually capitalize on and build a business on, that’s more of a painkiller. And so the more of a painkiller, your killer, you are the more, I think you can charge for your content versus if you really are a vitamin, just.It might be a more like prudent business model to stay free and just grow like a weed instead.Nathan: [00:20:49]Yeah. That’s interesting because all of these people who have successful paid newsletters do have that funnel. That’s still again. And you know, we see people make the transition. And then they’re so torn because you have this piece of content that, you know, is a flagship piece of content. You’re so proud of it.You know, maybe it’s like you’ve worked on over weeks or months as it’s kind of formed in your head that you’ve written it out. And then there’s this moment of like, wait, is this free? Because it will Dr. for people or do I put it in paid? So people go, Oh, this is the credible thing. I’m so glad that I’m a paying subscriber.And it’s. It’s a tough decision. And so I guessI move with us all, having the split where that, you know, there’s effectively two different jobs to be done. yeah. How do you think about what if you’re in that position of like an incredible piece of content or you’re advising a creator who has that of, should they put it free versus should they put it behind the paywall?What would you say?Steph: [00:21:47]it’s a good question. And the way that I would put it is again, there’s no right answer, but sometimes I equate, like paid newsletter as more like a bootstrap business versus a free newsletter, more like a VC model. And what I mean by that is. You’re basically, anytime you open up, whether it’s ideally, it’s a great piece of content, but even if it’s not, anytime you open up your content, you’re basically like trading your immediate, benefit, right.For a future benefit, right. By saying like I’m using this to build my audience, that I will later monetize the same way that like Uber grew four years and lost money. And then, I mean, maybe they know full profit, but like that’s the theory. Right. and so versus a paid newsletter is more like. Okay. I I’m okay with maybe not having a huge audience.But I, I can be really profitable and I can do that right away. Right. there’s no need to have this like trade off. And so it’s really up to the person because something, I also say to people, when they’re deciding between free and paid overall, and then also like where to put their content is just like, what are your goals?Because I mean, one of the aspects is money, but also like. I can say, I, I want to build an audience and I know other people want to as well. Right. And so if you really want to build a big audience, maybe you don’t, but if you do maybe kind of stray more towards the. Like free aspect of things, right.Because you’re on getting your content and it can work for you to build that audience. So I would write what I encourage people to do is like write down like what their goals are and pass just like, I want to build a newsletter. Like, do you want to build a brand? If so, do you want that brand to be you or someone else?Like how quickly do you need the money? like how does this integrate into any other projects you’re doing? Like, do you have a kind of paid product that you hope to launch in the future? and so asking those questions, I think will help you understand what your goals are and then you can align. Your goal is to like how immediately you want them to happen.Nathan: [00:23:34]Yeah, that’s a really good way to think about it because I think. Companies individuals and companies end up in one world. Like if there’s a lot of like the indie bootstrapped maker world, and if you end up in that side, there’s a certain set of tactics and ideas that you apply and you have this mindset and then you end up in the venture backed, you know, Silicon Valley, startup world.You might have a completely different set. And some of that I’ve always tried to do is play like in the middle of like borrowing things from, from both sides. Like. In the early days of, you know, when I, when I was self publishing books and courses and all of that, I was learning a lot from direct response, marketers, you know, about great copywriting, long form sales pages, but then I’d go to the startup world and be like, Oh, but they care about care about design.Whereas the direct response world they’re like design, nobody cares about design. So I had these long form sales pages. That were well-designed and then, and people were like, what is this thing? And it’s just like, Oh, it’s just something taken from this world. And then combined something from this world.And now it’s a new, a new thing entirely.Steph: [00:24:40]Exactly. Actually, speaking of Sam, he always says like, go look for the like scammy us companies, right. That are selling something that is really like, not a great product and go learn from them because don’t go create scammy products. But like the effort that they put into like, yeah, write incredible copy.Or like have these like long direct response landing pages is something that now people have associated with being scammy, but they work. Right. And so you can like, Use those same tools for something that’s not scammy and, and, you know, do even better because people actually will like your product. And so I think that’s great advice, like you said, to go learn from other industries that aren’t your own because they’re probably doing things that you’re not used to doing that you can almost certainly learn from.Nathan: [00:25:21]yeah, my favorite place, like my background’s as a designer. And so one of my favorite places to get design inspiration was actually like clothing stores, because you would go in there and they would have like their spring collection or whatever, and they would have, you know, like repainted and rethinking the store and like the tags.Stuff like that. Whereas everyone else was going to, like, I don’t know the CSS inspiration, like,you know, website galleries or whatever, for the most inspirational sites and copying from that. And it’s like, that’s why all your sites look the same. Like go, you know, but if you even walk into, I dunno, banana Republic or something, and like get inspiration from their fall collection, you know, on color schemes or whatever else and bring that to a site.No, one’s going to think like, Oh, it’s ripped off of something else.Steph: [00:26:02]exactly. I know we’re kind of going off track, but one thought I have, there is on this idea of like learning from other businesses is you can do the reverse, right? Cause you kind of just went like w take offline and like learn from it to implement online. But for example, one of the ideas I had recently that someone should go to.Take and build, I’m not going to build this is, you think about how many companies like Google or Facebook or Amazon that grew? I mean, partially because they’re just incredible companies with incredible operators, but also because they could AB test the hell out of everything. Right. because I could track and they could track those tests and implement them quickly.And you think about how many things in. In the offline world, you can’t AB test. And one particular example is now that all the restaurants have QR codes for their menu, something we actually wrote about in The Hustle a while ago was this idea that we’re actually this woman who actually does it, and she goes and redesigns different, restaurants, menu.So that. You know, the layout of the menu itself will result in like the average customer spending more at that restaurant. And she does it in just like a very manual way Write, she knows best practices, similar to how, you know, landing page, best practices. And she just goes in and designs at once, but she only has one go, right?Like she, she redesigns it and then it’s implemented. And I was like someone who needs to integrate into these like POS systems and actually create. this like AB testing protocol for different restaurants, where you have the same products, you don’t need to change your menu, like the actual menu items itself, but even just the orientation of where things are in the menu.And test that. I think that would be a really interesting business where again, you’re learning, you’re like doing the opposite where you’re learning from like online best practices and implementing them in a more offline setting.Nathan: [00:27:40]That’s fascinating. Cause yeah, you know, you sit down at the restaurant and you scan the QR code and you’re pulling out the menu on your phone. And who’s to say that two people are sitting at like tables near each other, have to see the same menu.It makes me think. I have a friend who runs a bar and they were like exclusively a bar, like craft cocktails and all of that.And then. They like added a little bit of food and, you know, they were able to open up like more of a full kitchen and out other things. And it was just fascinating. Their average order value went up so much, not just because they added food, so someone could buy that, but it was also like I’m here to get a drink or maybe two.But if you don’t have food, I’ve got to go somewhere else. And then once they added food, then it was like, Oh, I’ll buy that. And since I’m eating food, then I can stay for another drink. And so it was like turned into the cycle and I, I bet you could end up with very similar things. If someone’s sitting down like, Oh, I’m just here for a drink, but you could AB test that menu and get it designed really well where they’re buying otherSteph: [00:28:42]Exactly. Or you can just like, exactly start to design it like a webpage, right. Where you, they see the drinks. And as soon as they scroll down to the drinks, like a modal pops up and like, do you want some food or whatever? and so yeah, you could play around with it, but just learn from these, you know, different sides of the world and implementing them.I think. Like these are, I think, changes like that are going to be inevitable, but sometimes they just happen more slowly than, than others.Nathan: [00:29:04]Trends is very much a Research, different product. you know, and the way that you think I can tell, like you’re diving into things, just even what you’re saying of, you know, you’re like, well, obviously you’re going to Wolfram alpha and you’re like, drop it in. And you’d be like the page views of all of this.And I think a lot of creators don’t think that way. And so I’m curious, what are some of the other Research, you know, tips and techniques that you use that are just part of your daily workflow, where you’re like, like using Wolfram alpha in that way?Steph: [00:29:33]Yeah, so I’ll call it a couple tools and then I’ll just comment broadly on, on how I think people can like, be, just be more aware of what’s around them, but you know, certain tools like there’s so many plugins, like there’s a similar web plugin, which basically shows you like any website that you go to, how many pages it has, like, what sources those pastries come from, or sometimes I’ll just.Throw it in similar myself and browse around and even just like starting a habit of being, taking things that you’re already seeing and putting them in there. Sometimes you’re shocked at like, Oh my gosh, this site has like 90% organic traffic. Like how did they do that? Or actually they have like 90% traffic from this other source.And you start to look into and understand like how these sites grew and their relationships with other things on the web were off the web as well. other things of like during storing something into H refs, or if you think of a product, another great, Tool is jungle scout, because similarly you can throw in any, for example, when I was doing research on remote work, I was like, Oh, there’s a lot of like under desk treadmills.Or that seems to be a thing. So I throw it into jungle scout and you’re like, Oh my God. Like, so many people are making like hundreds of thousands of on these every single month. And then you start to do a little more digging and you’re like, Oh wow, there’s some cool other things like under desk ellipticals or, you know, other products that people are also making a lot of money off of.And so just the habit of. Like questioning what you’re already taking a look at and implementing, or putting it into some of these analytics tools. So just learn a little more and get a little bit deeper on it. And one of the tools I especially love is keywords everywhere because the things I mentioned so far take a little bit of initiative to be like, it’s not much, but to be like, okay, let me look into this.More, but keywords everywhere is inline in the browser. So when you’re actually searching for something, it tells you the keyword volume. It also shows how that’s changed over time. and some other things like secondary keywords, but, what’s so nice about that is you’re just going through your daily life and it’s almost just like, highlighting things for you that are interesting, right.Where you’re like. I don’t know, for example, in California, hard kombucha is, has been taking off. In fact, like in the grocery stores, you see harken boots, like at the entire section for heart kombucha. But if you go to Florida or I’m from Toronto, if you go to any of those places, like, I don’t see any heart kombucha.And actually like when I searched heart kombucha in my browser, completely unrelated to like, thinking about trends. you see it taking off, like you can see the search volume graph. and so the thing that I think is so great about that tool is again, just this idea where it’s actually like, just nudging you in the right direction to, to notice things.And that was the final thing I was going to say is that I think what I think we all can work on, including myself. It’s just. Asking questions about the things that are, that seem like really obvious around us. Right? So, on my first million, which is hustle Podcast, I think Sean gave a great example of one time where it’s like, you’re walking along the street and you notice like a patch of grass in between the streets.And most people like don’t even think about the patch of grass, but then you’re like, Who actually put the grass there. Right. Cause grass doesn’t just like show up on its own. and so who put this grass in between these two streets, right. and then who, like, why did they do that? Who funded this in this case, it’s probably the government, but like who takes care of it?Who makes sure that that grass is alive and all of those are some form of like business or, something that people actually invest in to some degree. and so you can do the same thing about just like anything around your home, or if you’re in another country, like why do they do things this way? Or.So interesting that, like I noticed this store that I’ve never seen in anywhere else in the world, like, why does it exist here? And not elsewhere? Sometimes the answer is like, Oh, cause like this is just like their tradition and you know, it shouldn’t exist elsewhere, but then sometimes you’re like, Oh actually, like it’s just because they started this thing and it could actually be shared elsewhere.Right. So it’s just this idea of like taking note of. Other things around you. and then again, you can use some of the tools that I mentioned to like dig into them more, but I think really where it starts and what we try to like train our analysts on, or just to ask more questions about the like really obvious things that already exist.Nathan: [00:33:29]Yeah.Yeah. That’s fascinating. And I think people get caught up in their own world or their own worldview, and they’re not expanding beyond that to try to see like, what are the things that challenge it. So I love the idea of having the browser plugins and, and like keywords everywhere and stuff of just like giving you these subtle nudges towards like, Hey, did you think about things in this way? Like when you have those ideas, you know, and you’re noticing those trends. Do you have a process for like making note of them or are you just dropping them in Notes or do you, do you have something, you know, more sophisticated where you’re keeping track of it so that you can then start to piece things together over time?Steph: [00:34:07]So it’s not much more sophisticated than just dropping them into Notes, but I, what I will say is that, Kind of almost what you were alluding to there. What I try to do is like piece things together. So if I have an idea, I’ll drop it in a note and sometimes the idea is terrible and I never revisit it.But once you start, actually, once you actually take the energy to write an idea down and it’s like, kind of. Implanted into your brain, almost like a seed, it starts to grow and you start to notice other things around you that are aligned with that, or that are similar, or actually contradict that. but it’s the same thing with actually writing online and how I write my articles is all like, you know, see a tweet that I’m like, Oh, that, that like struck a note with me.Or I will talk to a friend about a particular topic and, you know, really having a point, a point of view on it. And then I’ll just write it down and then I’ll notice. or I’ll just continually start to like, almost file things under that particular topic or trend as we were originally talking about. because I think that often, like our first encounter with something is actually not very sophisticated.Right. and often wrong as well. And so it is actually worth like, Watering that seed to use the same analogy with different examples, with intentional Research, with data. So that by the time you actually want to write about it or publish it, or even start a business around it, you’ve thought about it in many different ways and giving it time to breathe.Because often, like I said, sometimes I’ll write down ideas. And when I first think of them, I’m like, this is the best business idea. Like I’m going to quit my job and do this. And then like three weeks later, I’m like, actually this is a terrible business idea or Write. So I think it’s important to give these ideas time. And I will almost like almost like, you know, the Dewey decimal system in that library. Like you have certain, you have certain topics that you like set out and then after that you’re filing things under those topics. So that by the time you go back at some point, ideally you have more of like a full library of content that gives you a more full perspective.Nathan: [00:36:02]Yeah, that’s interesting. I, on the past ideas thing, I think that a lot and someone tweeted this morning, I can’t remember who it was in my like random scroll through Twitter of like, I always think I have great ideas, but then I look back at the past list of domains that I’ve purchased. And I’m like, what was I thinking?You know,Steph: [00:36:21]So true.Nathan: [00:36:22]You know, it comes up for renewal and you’re like, I can’t believe I spent $8 on that. ThatSteph: [00:36:27]No.And we’re, so it’s like digital hoarding as well. Right? Where even if we know it’s a bad idea, we don’t want to let go of the domains. So we’re like, Oh, I guess I’ll pay 30 bucks for this that I know I’m never going to use.Nathan: [00:36:39]Yeah, for sure. so I’m curious to dive into a little bit of your path to, you know, running trends of The Hustle now, because it’s a job that. Is pretty unique as far as the skill sets that it takes and all of that. And so, I’m curious, you know, where, you mentioned that you grew up in Canada. I, I’m curious a bit of your path to go from, you know, maybe starting out your career to, into The Hustle.Steph: [00:37:08]Yeah, so..Nathan: [00:37:09]But…Steph: [00:37:10]I know I’m like, how far back do you want me to go? But basically I, I did my degree in chemical engineering. I ended up. Going actually into consulting after that, because most people in chemical engineering, you either go work on an oil rig or in a chemical processing plant or something of that nature.And neither of those really appealed to me. And so I was like, what did I like about science? I liked problem-solving and, that did translate over to consulting. So I was a management consultant for a year or so, but I was living in Toronto, pretty classic like pre remote work story where I was like commuting two hours a day, living in a city.I didn’t love. Working way too hard. And I only spent like 10 months there before going fully remote. Then I worked for a company called top tower, which is a tech company. I did that for three years, but that’s when I really started getting into marketing and growth. and so I started on the growth team, led their publications team.And then after that I joined The Hustle and it was pretty random actually, because during my time at. Topsail, I had led their publication scene and I had started to write online on my own as well. And I guess my, my own personal blog had taken off, but I never considered myself a writer. Like I was only writing.You know, for on my own. And I had somehow found myself into this, like leading this publications team, but that, really was not like what I even saw myself as, but Sam had seen one of my tweets tweeting one of my articles, and he just reached out and he was like, Hey, like basically, you know how direct Sam can be something along the lines of like, Like we need you on trends or like, can I hire you like that?And it turns out that we actually were in touch for like six months or so really on and off. but the first role didn’t really make sense. And then, before actually when he first reached out trends didn’t exist, but then he reached out to me again and he was like, we’re launching this thing called trends.And I was just like, Oh my God, this sounds amazing. Right. Where you can just like, follow all your different curiosities and write about businesses. And so I ended up just like, it was also the right time for me to leave my job just going into this. But I had no professional writing background. I, really, I wasn’t like an, an analyst or anything of the sort, I hadn’t built my own business.So I was kinda like, I don’t know if I can be very good at this, but I, it was really, it was great. I wrote for trends for like eight months. Maybe more, maybe a year almost. And then I ended up leading the product. but I think that’s something Sam’s really good at is just like finding people online who maybe don’t have like the, like pre-recs to say, you know, as you would say for a job, but then just like, you know, Trump was the same way he was, he’s like one of our writers and he, he worked in finance before, but never really written, but he’s worked out well as well.So, that’s kind of how I ended up there. so it’s been totally, you know, random, I would say it, but, Yeah, I’m really happy that I ended up at The Hustle and trends has been like such a great product to work on because it really does just teach you how to like be analytical and follow your curiosities and then take your curiosities and translate them into something other people might care about.Nathan: [00:40:11]Yeah, that’s interesting. I didn’t realize that you had a degree in chemical engineering. What’s the, the process, w or what is it like that you think you still use today from that degree? And that you’re using a lot at trends in The Hustle?Steph: [00:40:26]Yeah, so I think I actually am so glad I took that degree because I mean, there’s so many other degrees that do this, but it just teaches you a lot of critical thinking and problem solving and just like being analytical right. Where, I don’t know how to size a pump anymore, even though I was taught that at some point, but same thing goes for anyone in, in most college degrees.Right. You don’t actually remember exactly what you learned, you just learned how to learn. So that was like, I would say the, one of the more significant parts of like, what. I remember. And the other thing is just, I love this concept of thinking like a scientist, which is this, you know, idea where actually nothing is true.Like nothing in this world is like a zero one true or false. And in fact, we don’t even know this sounds like a little woo, but we don’t know what the truth is. Right. And in fact, the scientist is just trying to be less false over time. Right. And if you actually, cause that’s really what you’re doing, right.Is like, I love and like, You know, grade seven or whatever chemistry where you learn about someone and their contribution to chemistry. And you’re like, wow, like that’s amazing. And then the next class they come in and they’re actually like, well, actually that’s wrong, right? Because a hundred years later, this guy or girl, you know, found out that, you know, that model was incorrect and this one is the one, and then that keeps happening and you’re like, Oh wow.Actually like. imagine being that scientist at the time, thinking that they had solved the world. And in fact, like they had made a major contribution because they got us to be less false, but they were not, they didn’t find the truth. And I think that’s really important when you’re like just even engaging online or building things, or being a creator is just to know that like your job is not to like.Let’s see what’s true or false. It’s just to like contribute to the world and get us to be less false over time. And then also to have an open mind where like anything, you know, today can be proven false in the future. So just like to be a little more open to learning about like what else is out there.And I think that actually did translate to trans who’s trans is all about like, W what can I predict about the future that like, maybe I would not understand today, right. Or not predict today. And so I do think it leads to you having that scientific mindset. I do think leads to people having more of an open mind cause they’re not locked into like them being right or wrong and more so just like finding what’s a little bit better.Nathan: [00:42:39]Yeah. Oh, that’s fascinating. I love the idea of, I mean, it sort of goes, it reminds me of strong opinions, loosely held,Steph: [00:42:46]Yeah, exactly.Nathan: [00:42:47]Diving into that. I’m curious. Are there things that in, in your career, either at trends that. Were those things. We were like, Oh, this is the way that you grow something. Or this is the, this is what works for Content are all of that.And then, you know, found, you know, new data and all that, that proved you wrong.Steph: [00:43:03]Oh, that’s such a good question. I mean, I’m sh I’m sure of it. I’ve been wrong so many times. I’m not sure if one, like super obvious one comes to mind. but Oh one, this is like a very simple one as a marketer. So when you first come into Marketing, you think that your intuition is going to be right about a lot of things.So you think that like, if you were to look at a line or a stack of like ad copy, you’d be like, Oh, I think these ones are gonna work. And I think these ones are actually really terrible. And when I first started at Toptal, I was on their growth team. So I was responsible for like running certain ads on certain platforms and things like that.And. We are, I was just so shocked at how wrong I was. And that was actually like an aha moment, in the first six months or so, where I was like, well, I’ve truly know nothing about like, what’s going to convert. and after that I was able to have a much more like, just test everything mindset, but that is actually, if you haven’t.Worked in Marketing. I think even if I tell you this, you’re not going to fully internalize it until you experience it yourself, where like you have to test things and then realize how often, and also like the, to the degree that you can be wrong, where you’re like, Oh, these are pretty similar. Like surely they’re going to, perform the same way.And it’s like, no, just like a button color changed can be like, Step change is better than something else. And so I think that was something that I had to learn, you know, on the job, which I really didn’t have the right mindset for going into it.Nathan: [00:44:28]Yeah, it makes me think of, we’ve been doing a lot more recruiting at ConvertKit over the last 18 months to two years or so. and I’ve had this thought always that like a short, personal email is what’s going to do the best, you know, like three sentences. It feels like, you know, maybe it was copied and pasted in some way.Right. But it doesn’t feel like this long thing. And we started testing. So Barrett who’s our COO, he wrote this email that is ridiculously long. I’m like, this is never going to work, you know, and we’re trying to recruit a VP of product and a VP of engineering. And he’s like, all right, well, let’s test the emails, you know?And so we started sending out both the versions and the ridiculously long email that has like all the information you would ever want in it. You know that, and it’s personalized somewhat, but everyone knows that someone didn’t like sit down and type out a 500 or a thousand word email, you know, about this role to one person.And it performed wildly better, like night and day difference. So we have like VP of design at like major tech companies is responding and going. Like I’m not interested, but this is a great email, you know?And so it just like shattered all of my preconceived notions about, you know, like I was even able to say, like, we’re not sending this email.That’ll never work, you know? And not only does it work, but people aren’t saying like, it’s, you know, it’s a step function above, you know, anything that they’ve received before. And so who knowsWell, actually, I thought the thing that I’m wondering is you have the advantage now of traffic and we have the same thing at ConvertKit of like, we can run all these AB tests because we can get to statistical significance sometimes not as fast as we would, like, especially if it’s a test is a ways down the funnel. what do you do in those cases where you don’t have enough traffic to reach statistical significance or, you know, there’s not quite a clean AB test that you can run.Steph: [00:46:26]It’s a good question. I think so one, if you don’t have a lot of traffic, like you are limited to the amount of AB testing you can do, but you can also there’s things like MTurk and you can, you can test things outside of like where you’re actually planning to test them. there are a lot cheaper, but even past that, I think.When you’re, when you’re early on, like, you don’t need to, optimize as much, like, obviously if you can. Great. But I think early on it’s about like, just getting something that’s pretty good. And then focusing on scaling and then once you’re at the point where you’re at scale, that’s what really, when you’re looking to tweak and like fully optimize.And so I wouldn’t worry too much about, like, another thing that is worth mentioning is that. There is an extent to which AB testing becomes too much right. Where you’re so focused on like tweaking and not actually focusing on like step changes. So, that’s something just worth calling out, but if you’re there early on what you’re really supposed to be focused on, just like validating the product, right.And not necessarily, fully tweaking your funnel so that it performs optimally. So that’s, I think an important takeaway if you’re at that stage where you don’t have traffic.Nathan: [00:47:32]Yeah, that makes sense. Something along those lines that I want to make sure we talked about is differentiation and. Like I’d love as very broad, high level question, but you recently wrote a book on this. And so I I’d love for you to just talk about how you think about differentiating products from each other and just differentiation as a whole.Steph: [00:47:48]Yeah. So I think when people create products, especially when they’re online written content products, they forget how important packaging is, right? So they focus so much on what they’re creating and not how it’s different. And we can start by actually talking about. Like physical products, right? When you buy a physical product, you often buy it because it’s cheaper sometimes.But sometimes because you like love the packaging or because you, you really like what the brand stands for, or it’s so much faster at achieving what you’re trying to actually accomplish or whatever, right. It’s something that you can like clearly articulate and say, this is better because of X versus whatever else exists out there.And what I find when a lot of people Write info or Content products, is they focus just so much on, like, I’m going to write a newsletter about. Business or tech or fashion or whatever, I’m creating a travel blog or, and it’s like, great. But like we’re at the point where we all know this barrier to entry is so low, that there’s so much supply of Content.So how the hell are you going to stand out? And what I encourage people to do is to focus on exactly that, that kind of question of like, what is your very, very, very clear differentiator that you could tell. Someone else. And also, so that anyone reading your stuff could also tell someone else, right? Like that’s how you would get word of mouth.And the way the exercise I encourage people to go through is basically go through your inbox. You can do this with newsletters or other products, but if a newsletter go through your inbox, write down your favorite newsletters or the ones you subscribe to write what you like about them in a sentence.And then parse that sentence into an adjective. Right. Is it like shorter? Is it more contrarian? Is it more, Weill Research? Is it funnier? Right? Like there’s very clear adjectives that you can normally, label something as, and if you can’t, you know, there are cases where this is not true, but most of the time it’s like, well, they actually don’t have a clear differentiator, and do the same thing with like something that.You remove from your inbox, right? So something you didn’t like where there’s often a clear reason as well, where it’s like, it just got too long or it became too political or, you know, something that was very clear and tangible, which is why you took that action to either subscribe or unsubscribe. And if you think about it, most of what you’ll find is again, most of the time it’s like, Well, the thing that you write that you like about it, isn’t like, I like that it writes about tech because so many things write about tech.You like how it writes about tech, right? You like how the person engages with you, how they show up in your inbox. and then the, what you should do is then go back and as you’re either at the stage of designing your own Content product, or if you already done that, go back and make sure you’ve, you’ve revisited the step of identifying what yours is.And I always like to give the example of Costco, cause this is actually advice. Spans, not just Content products, but I find that’s where it’s forgotten the most, but all products, services, startups, like you need a differentiator. And I always give the example of Costco, which is so good at having just such a clear in their name it’s costs.They’re cheaper than anything else that exists. And what a lot of people try to do is they’re like, okay, well I want to be funny, but I also want to be like, really well-researched and I really want to be like visual and I want to be like all of these things and it’s like, you can’t be. Everything to everyone.And so what Costco did is a great case study of where they said, you know, all we care about is having the cheapest items for our customers. And in fact, if you think about the laundry list of things that people might care about with, within like a general retail store, they might care about location.They might care about. Like ambience or package size or customer service or all of these things, which Costco was like, you know what, actually, we’re going to try it. All of those things off to get like the absolute cheapest goods for our customers. You have huge package sizes. Like you don’t really get customer service.It looks like a factory because they’re such big superstores are hard to get to. Right. But they trade it all of that off to be like, look, we have the cheapest gas or the cheapest, like. Donuts or whatever you buy from Costco. and so that’s like a lesson where if you want to stand out in a very, very crowded space, which pretty much everything in Content is today, then you really, really need to think through like, whatever your differentiator is.So again, like how you’re accomplishing something versus what actually you’re buildingNathan: [00:51:57]Oh, that’s so good. And I’m just thinking about the number of conversations I’ve had about newsletters, where people are talking about, you know, quality and consistency and. But really not that much about positioning and differentiation.Steph: [00:52:09]Yeah, exactly. And that’s why someone will like spend time with you, right? Again, whether your info product or like a physical product or service, it’s like someone will spend time with you because in their head they might not even be conscious of this, but they. They’re like labeling you. They’re like, I love ConvertKit.Cause it’s so seamless, right? Or it’s it’s, you know what some other brands it’s like, I love this because it’s so cheap. Right. And, and if you can’t really articulate that again, your customers can’t really even consciously or unconsciously articulate that to themselves. And they’re just going to be way less likely to be, to work with you or read your newsletter or whatever your product is.Nathan: [00:52:45]Yeah. Yeah. That’s interesting. so as you kind of do that exercise, right, you’re deeply embedded in the newsletter world, maybe what are some of those newsletters that you, you did that exercise with and have an adjective that come to mind? Like you follow this because they are the fill in the blank.Steph: [00:53:01]Yeah. So I’ll give you a couple: One of them that I think a lot of people love is James Claire’s 3-2-1, and people, some of the adjectives, like, cause I’ve done this exercise with people, who’ve read the book who are like concise stress-free right. And that’s like, again, some people might have different reactions to the same newsletter, but there’s something about it’s short, right?Where it’s just, when people see that in their inbox. Like you said some, you have to test all this stuff, but sometimes when you get a huge long newsletter, you’re like overwhelmed. You’re like, I don’t want to open this. Or, but that you don’t get that with his 3-2-1 newsletter. You love it. You know, he says even his tagline is something like “The most, value in the least amount of words,” or something like that.And so it’s like, you can clearly articulate, like, it may not be everything to everyone, but for the people who really value like, a thoughtful, concise. Piece of work in their inbox every week. Like it services those people and they love it. another one is charter. So Chartr, is chartr.co I think.And, it talks about business and tech similar to The Hustle, or similar to morning brew. Like there again, dozens, if not hundreds of newsletters that write about business and tech, what Chartr did. And they, I think they only started in 2019 or something in that like in the last year. Year or two, and they’ve just grown like crazy.And the reason for that is they are just purely visual and so that they do have some texts, but most of it is like these like really snappy, very cool infographics. I personally love Chartr. It’s again, these are the ones where I went through this exercise because they’re in my own inbox where I thought, you know, I do, even with The Hustle sometimes get overwhelmed.It’s a lot of texts. and it also, you know, as they say like a picture, is worth a thousand words where you look at this and you use the visual nature of it. You understand a topic more often than if it’s just written about, in long form. And so Chartr is, again, it sounds simple, but more visual again, you could also use things like stress-free because I can get through my inbox quicker.People love The Hustle. The most common reason that we get is that it’s just funnier, right. Or people might say something like more relatable. And where again, it’s no BS, no jargon. It’s like your friend talking to you. Right? So those are a couple of examples of ones that in my inbox and how, or why I continue to engage with them.Nathan: [00:55:15]Yeah. Oh, I love that. and it’s, it’s given me a lot of thought of that. I’m going to go through and do the exercise with, my own inbox and the newsletters that I write or that I read and then take that even to my own newsletter. Cause I think it’s easy. As a creator to fall into the trap of like, okay, I need to show up consistently.And then you kind of start to lose track of why you’re showing up consistently, and angle of why people subscribe to wasSteph: [00:55:40]Exactly and that’s it. That’s what it is, right. An angle. And, and by the way, like none of them are like, Black or white, correct. In the sense that, for example, some of the ones I just mentioned, I really liked that they’re concise, but another newsletter that I love is one called like exponential view.Right. Which is not super long, but it’s, it’s so interesting. And like, it’s, maybe it’s an adjective I would use as like intriguing or it’s kind of like trends where it’s like, I didn’t know this. Right. And it keeps me like educated. I feel educated when I read it and I feel like.Ahead of the game in some way. And so, that one does give me a little more like anxiety to open it sometimes. So sometimes I’ll like, you know, save them for like end of the month or something like that. But when I do read it, I feel like I get enough value. So there’s no right or wrong as something being short or long or funny or not, but for your audience, whoever you’re trying to target, and what they need, like having your angle is really important.Nathan: [00:56:36]Oh, that’s good. the last thing that I wanted to ask you about is. Kind of this balance between, you know, your full time thing with The Hustle and running, running Trends, and then your own content and everything that you’re writing. you know, you mentioned before we started that, or I think over Twitter DMs, you know, that you’re focused much more on The Hustle right now, but I’m curious how you, how you balance those things and how you think about having, a side hustle while you’re, focused on an all consuming product.Steph: [00:57:06]Yeah, I mean it, so it definitely depends on the person, what their goals are. But for me, I’ve written about this actually, because I’ve, I’ve been creating my own projects since I left consulting, which was in 20. What year was that? 2016. So for the last five years I, on and off, I’ve been creating my own projects and like doing things like learning to code.And so what I’ve found is, again, this is not for everyone, but the fact that I get paid for a job that I love actually gives me enough financial freedom to then go and pursue whatever the hell I want on the side. And it just turns out that I like writing. I like. You know, building, tinkering with stuff online.But I actually think that’s like an underrated thing where a lot of people think like, you know, there’s the like, you know, and for dropout stories where you’re like, I need to drop out to go create like the biggest, biggest businesses in the world. And that’s the only way I’m going to be successful, but I’m actually, like, I get paid to learn from a bunch of other people who are smart.I get to work on cool projects. And that gives me the financial freedom to do whatever the hell I want on the side. And one of the underrated parts of that is like, Because I don’t need to rely on them for my financial freedom. My projects are not only more fun, but like more authentic, more like I can do whatever I want with them.There’s no pressure to like turn them around and monetize them overnight. that’s why I could build my blog and my Twitter and all these things without like, we talked about like gating content before how that can really restrict your growth. I don’t need to do any of those things because like, I. I can just like, get my, my financial freedom through my job and then, you know, work on other things on the side.So, again, it really depends on the person, but I’ve found that to be really great. And then I just pursue my curiosities on the side.Nathan: [00:58:48]I love that. Well, thanks for coming on. And where should people go to follow everything that you’re doing and dig in more on differentiation and all of the things.Steph: [00:58:58]Sure. so yeah, we talked about Trends. You can find Trends at trends.co, or The Hustle at thehustle.co.And you can find me at, on Twitter is I guess, where I’m most active, which is @stephsmithio, because my personal website is stephsmith.io.Nathan: [00:59:12]Sounds good. Well, yeah, I’m, I’m excited to dig into more of your work and, and, there’s a bunch of Research things that I’m going to be using in my workflow now going forward. So thanks so much for coming on.Steph: [00:59:22]Awesome. Thanks so much for having me.

Nat Eliason is the founder of Growth Machine, a successful SEO and content marketing agency. Nat also teaches the popular Roam course, Effortless Output.Nat earned his B.A. in Philosophy from Carnegie Mellon University, and has worked for companies such as Zapier, and Sumo Group. Nat co-hosts the Made You Think podcast with Neil Soni.Nat also writes a weekly newsletter called Monday Medley. Each Monday Medley has ten articles, videos, discussions, pieces of research, or other interesting finds from around the Internet, spanning a broad range of topics.In this episode Nat discusses the evolution of his newsletter. He shares his strategies on developing online courses. He also explains how to find product-market fit before launching a course or product.Highlights of the conversation include: How Nat made $300,000 from his online course What separates a mediocre newsletter from a great newsletter The differences between running a newsletter and teaching a course How Nat balances work, family, and leisure Links & Resources Shane Parrish Farnham Street Sunday Brain Food newsletter Tim Ferriss Five Bullet Friday Azeem Azhar Exponential View airr Building a Second Brain Tiago Forte Wes Bos Derek Sivers Nat Eliason’s Links Effortless Output with Roam Nat’s Twitter Nat’s website The Monday Medley Made You Think podcast Episode TranscriptNat: [00:00:00]Build up little channels. There’s a lot to be said for having one thing that drives 10 grand a month. But if you’ve got 20 little things that drive $500 a month, that’s cool too. In some ways it’s a little more resilient because if one fails, you’ve only lost 5% of your revenue versus if the $10,000 a month thing fails, you’ve lost all of your revenue.Nathan: [00:00:26]In this episode, I talked to Nat Eliason. We talk about a bunch of different things ranging from his newsletter, the course that he’s running, you know, earning a crazy amount of money from the course, his thoughts on paid newsletters versus courses. Really just how he approaches life. It’s kind of a meandering episode as we go through those details.I love the way that he’s not trying to grow and optimize everything. And then also the way that he’s taking internet money and bringing it into like tangible, real world life experiences, connection with friends, things like that. So it’s a great episode. I hope you enjoy it. And, actually before we dive in, I’d love for two things.One, if you’re listening to the podcast and you just clicked through from random clips or things like that, and you haven’t subscribed, go ahead and subscribe in iTunes, Spotify, and, you know, wherever you listen to podcasts, really appreciate that. And then the other thing is, I realized I’ve never actually asked for reviews and it turns out reviews help, you know, with rankings and more people to discover the show.So I would love it if you would go on iTunes in particular. Is iTunes a thing? Apple podcasts, I guess you go on Apple podcasts in particular and subscribe and then write a review or just a rating. That’ll help more people discover the show. So thanks for doing that. And let’s dive into the interview.Alright, Nat, thanks for joining me.Nat: [00:01:40]Yeah. Thanks for having me, excited to be here.Nathan: [00:01:41]Why don’t you just kick things off by talking a little bit about the newsletter that you have, and I’m actually curious, you know, how long ago you started.Nat: [00:01:51]Yes. So my name is Nat. Hi, in the world of newsletters, I started my newsletter, which is called the Monday Medley or often just the Medley in may of 2015, no 2016.Nathan: [00:02:08]Either way it’s been awhile.Nat: [00:02:10]Yeah, it must be only 2016, cause I’m coming up on five years next week. I think it’s next Monday is the five-year anniversary.So, I’ve been sending it out every single Monday for five years straight, which is kind of absurd. I actually, I have no idea how I haven’t messed one up in that time, but here we are.Nathan: [00:02:34]At 200, what was that, 260 weeks?Nat: [00:02:37]Yeah, it would be what, 260? Yeah, three times five. So it’s a lot of newsletters.Nathan: [00:02:42]That is. So what made you start the newsletter? Were there particular people you were following? And you’re like, “Oh, I want to be like them.” Or was it solving a business problem for you?Nat: [00:02:52]Yeah. So I was originally following sort of the standard advice of emailing every time an article came out. And that was working fine. And this was for my personal site NatEliason.com. and I was emailing for every article, but it’s like too many emails. Cause I was writing like a couple of posts a week back then, and I didn’t like having to like write a specific email for each article. And it felt like there wasn’t that much like extra value with being on the newsletter besides getting updates on posts, which people can do if they were just like on Feedly and subscribe to the RSS feed or whatever.So, I saw Shane Parrish start his, brain food kind of newsletter for Farnam Street. And, Tim Ferris had launched his like Five Bullet Friday, around that time too. So the Medley started as very similar to those two where it was like, you know, here’s like something interesting. I read this week. Here’s like a video I enjoyed just kind of like a little, link dump.And it was kind of that way for two or three years probably. And then it transitioned into kind of a different vibe where I got a lot of inspiration from Azeem Azhar and his Exponential View newsletter, which is like really, really good. And I just loved how, like, he wasn’t really just sharing stuff that he found interesting.He was kind of like going in depth on each thing. And what I liked about his was I felt like a lot of the link dumpy newsletters were, they didn’t feel very like high effort or very high value. And it was just like, okay, like, here’s kind of like a dump of things, but you can kind of get that from Twitter or elsewhere, plus like everyone was doing it right.It wasn’t that special anymore. So I was trying to think of how I can make it higher value. Azeem’s was such a great model because he was like going into detail on each thing. So I shifted in that direction first, where it was like, okay, here’s, you know, five, six, seven things from this week that are interesting.They’re kind of like in categories. And here’s like my thoughts on them, or like a bit of, a bit of summary on them, if you don’t want to like go read them. So it made it a lot more detailed. and then in the last like three months, it kind of shifted again to being somewhere in between like a standalone, like news letter or like, like periodical kind of like what you would expect from a sub stack and that, like link roundups.So now when I do it, there might only be. Like two, three or four articles, pieces, whatever I’m referencing as like the jumping off points. But then I might write like 500, 3000 words about them and kind of like more of my thoughts on them, more how they tie into like broader themes of the newsletter reference things that I’ve shared in the past, trying to make it more of like a, like a journey through each week, instead of just like a, like a dump of information.So it’s evolved a lot over the last five years. and I think it’s, I think he’s evolution has been good and made it like better. Yeah.Nathan: [00:06:10]And so doing it for five years, interesting to me in that, like that’s a long time to show up consistently every week. has each iteration made it more fun? What are the, like, what are the things that have made it so that it’s been good to show up consistently and you’ve stuck with it for so long.Nat: [00:06:27]I think each iteration has come from me meeting to make it fun. So like it changes each time. I get bored of it is probably the best way to put it. Right. So like I got, I got kind of bored of doing just like, Oh, here’s like five things I found this week. So I was like, all right, let’s try to make this a little more interesting.And then I was like writing all of this stuff about each thing, but then it was all of this work to go out and try to like find a bunch of stuff to read and write about each week. And so that was starting to feel kind of like a slog where each Monday it was like, okay, now I need to go like read articles for two hours because I didn’t read enough during the week and then need to write about it.And so I was like, well, what if, what if I tried to be like, More selective and just picked a few things that were really good. Cause that was the other problem was that the talking about a breadth of things was actually encouraging reading shorter, lower quality stuff. Right. Because let’s say that I’ve got two hours to read material for the Medley, but I feel like I need to send six, seven, eight things.I’m going to read stuff that’s shorter and probably less good, just so I can like fill my quota. Versus what I like about what I’m doing now is I have good incentive to read, you know, a 30 minute or 60 minute article because I could just riff on that for the entire newsletter and it could be really good.So that’s made it a lot more enjoyable to me. And I think that, like one thing that I did from the outset that has helped it stay interesting is basically not branding it around anything or not theming it. and just being like. This is whatever random stuff I’m interested in this week. Right. So, you know, one week it’s going to be, it could be about like health and other week.It could be about like crypto stuff and then a week it’s about marketing. And then it’s about like knowledge management. I just sort of like, I mean, that’s why it’s called the Medley rice. It’s like, whatever stuff it feels like going out this week is going out. it’s probably helped with the longevity a bit too, because I think that if you have like a, a very specific niche newsletter Write or anything, right.Like you can grow really quickly, but it’s also a little more replaceable. People might like get bored of that topic and move on. when you have, when you brand new rap, just like trying to send consistently interesting stuff each week, I think it’s got a little bit more longevity to it. So, this worked out.Nathan: [00:08:43]Yeah, I think the same thing people often in the early days of my blog would ask why it had it around like Nathan Berry instead of, the topic, you know, and part of it is, cause I was talking about, like how to design iPhone applications at the time. That’s my, my entire site or 80% of my site was about that thing.And so it could have been called, you know, iOS design weekly or, you know, whatever else it turns out I lost interest in that topic. And I moved on to other things and because it was themed around my, you know, my name, all of that, then I could just move with me and I’m sure some people dropped off. You know, some people were like looking at, and I don’t care about designing web applications or Marketing, or cell phone wishing your newsletters, any of this stuff.And so they drop off, but most people, you know, stuck with me and followed that. And so I think what you’re doing of having it around your name and just like, this is what I’m interested in. If you don’t like it, like there’s an unsubscribe button. If you do like it, you know, telephone.Nat: [00:09:40]It definitely helps. I mean, I think it makes it harder in the early days, right. Because. People people almost need like an initial thing to hook on to you from Write. Right. And so for me, a lot of that was probably around like SEO and writing about like search engine optimization and content marketing, and doing all of that.And then kind of like letting it expand from there, just like what you were talking about, right. It’s like you started with iPhone app development and that was like the initial thing, but it was still under your name. And then as you expand it to other topics, some people come with you. Some people like fall off.I mean, it’s kind of fun talking about a variety of things because you, you get like very different people from all walks of life or from all areas of interest who, and, following your stuff. it also creates like these funny situations where you have like a strong opinion in one area. and you’re like, you do a lot of stuff in another area.So people follow you for this thing. And then you like talk about this other thing and then suddenly you get like angry emails about it. so that’s one downside.Nathan: [00:10:42]Do you have a specific example or two?Nat: [00:10:45]Yeah, I’m very against like fake foods or like, I think that fake foods are just like really terrible for us or bad for the environment, bad for everything. but I, and then I have like a lot of people who’ve come in through the like Roam Research, personal knowledge management, productivity space. So every now and then I’ll have somebody who like comes in through the Roam stuff.And then I like say something incendiary about Oatley and my newsletter. And they’re like, so those are always kind of funny, but, that, that does happen every time. Right?Nathan: [00:11:20]Yeah. I could totally see that, you know, but what did they say if you’re not hated by someone you’re not doing anything meaningful? I don’t know what it is, but.Nat: [00:11:29]My heuristic is like, if, if a, if a newsletter edition doesn’t get like 0.1% of people responding, like. Disliking it or being annoyed about something, then you probably haven’t said anything like that. Interesting in it. Right? Like if you’re, it’s something like, yeah. If you’re making everybody happy, you’re like not, I’m totally butchering it, butNathan: [00:11:56]Generally what we’re getting at. So the takeaways we’re bad at sharing quotes. I’m curious, what are some of the like, fun experience that experiences that have come from the newsletter of like either, you know, serendipity or like people you’ve met or opportunities that came up because of it. And we’ll get into courses and revenue side of the second, butNat: [00:12:15]There’s a ton, like I’ve made a decent number of real life friends from my newsletter. Right. and it’s, it’s hard to suss out whether it’s like the newsletter or Twitter. I think that they like go hand in hand very closely, but I believe at least half of my real life friends are now like came in some way from being an active internet person.Right. And so that’s super cool. have a lot of like, people send me really interesting stuff now each week, whenever I send out the newsletter, which is fun, and also. Kind of like daunting because I’ll, I’ll send it out and then I might get a dozen replies or whatever of people saying like, Oh, this is cool.You should check this out too. Or like, somebody will point out something that I got wrong and then, you know, like go down that rabbit hole and explore it. So it’s great because I actually learned a lot from the newsletter now, too, from what people sent back to me and that’s really fun. And it kind of like, lets me go down rabbit holes.There’s other cool stuff. Like, my favorite is when I share an article in the newsletter and I’m like talking about, you know, this is really great. It was interesting, you know, here’s what made me think about, and then like the author is on the newsletter and he replies, Oh, wow, thanks for sharing. And then like, boom, where like instant internet friends.Right? Like that’s happened a number of times and that’s always a really, really fun experience. I’m trying to think what else, like there’s obviously the business side of it. And I think just like, I. Seeing the newsletter, like help people, especially early stage companies or people who are just like starting to get the word out about stuff.And I mean, there was like, there’s this podcast app that I really loved called air air. And, I found out about it relatively early and got in touch with the founder. And we just like jammed for a bit and talked about like podcasting and note taking and stuff. And then I shared it in my newsletter and he texted me the next day.He was like, yo, that was our highest download day ever, like so far. And I was like, that’s super cool. Right? Like, that feels really good because it’s like, I found this thing. I liked it. I shared it. And it like made some small, meaningful impact in their business. Like that part. I really, really enjoy.Nathan: [00:14:21]Yeah, it’s amazing to have that attention to be able to direct to things I friends are doing or just that you think is cool. Like so often, you know, like the most value you could give to a cool project is like, Oh, let me click retweet. You know, which doesn’t really do much, but to be able to come across something and be like, Oh, this is amazing.More people should know about it. And, you know, be able to send tens of thousands of people. That direction is,Nat: [00:14:44]super cool. Yeah.Nathan: [00:14:46]this is a bit unrelated, but you’re talking about, you know, making friends from the newsletter and all that. Something interesting that I think you posted on Twitter is, or maybe putting the newsletter is really a focus on like, as the world opens up in a post pandemic thing of, like you’re saying, I actually just want to like make friends locally, like I’ve.I spent all this time, you know, like we could all get on the plane again. We could go to conferences and, and like expand our internet circles. And you’re like, look, there’s plenty of people here in Austin here in the area around, like what drove some of that thinking of like investing in local community and just making friends around you.Nat: [00:15:23]Yeah. I mean, I think that it was a combination of things, you know, one pre COVID. We were probably traveling like minimum once a month, like often, twice a month. So, you know, going somewhere every other week or every three weeks, something like that. And that was just a very normal for two years or more, I guess it was just like, Oh yeah, this is just like what we do, right?Like, you’ve got the ability to travel. Like you shouldn’t travel and you should like go these other places and like, see things like Instagram and whatever. And then, you know, COVID hit and, you know, I don’t know what it was like in Boise, but in Austin, especially in our community, we sort of like gave up on a lot of the.Like social guidelines very quickly where it was like, we had a very healthy, very young community. We were just hanging out with each other. We weren’t like seeing at risk people. And we were just like, you know what, we’re just going to roll these dice and not like spend a unpredictable amount of time, completely isolated from each other.Right. Cause it’s like, there’s a lot of risks with that too. Right. Like it’s incredibly unhealthy way to live. So we just like started doing dinners with friends, doing cookouts, going for walks, doing like random activities, like almost every single day of the week. And so like we would be going to someone’s house for dinner.They’d be coming over for dinner. We’d be doing cookouts on the weekend. And so Write, it was just like. Nonstop social, like group stuff that was at people’s houses and in their yards and not like at a noisy bar, and didn’t involve like having to get on a plane or like going anywhere. And pretty much all of us were like, Holy shit, this is so much, it was just like, this is, this is like the best way to live.This is awesome. we all got really good at cooking. Like a few of us bought like ranch houses outside Austin with acreage, or we could go like, hang out. I mean, it was just like completely new lifestyle. It was so much better. And so as you know, stuff is opening back up, we’re all kind of like, we don’t want to travel.Why would we go? And like, why would we do get on the plane and go somewhere? when we can just like, enjoy life here, like, why would we go to bars when we can like, have, you know, dinner or like drinks and party and stuff at friend’s houses? Or like, why would we go to. Any restaurant, except like the very few that can legitimately make better food than we can get at home.But it’s just like completely changed our relationship with like socializing and time. And I think there’s like this, this tough question of, you know, like who do you want to build a deeper relationship with? And I think, you know, and every time you choose to spend time with someone or with some place you’re choosing not to spend time with someone else or with someplace.And so every weekend that you get on a plane and go to somewhere else in your you’re like deepening a relationship with something or someone that’s like not actually where you live. Right. And so there’s this element of like, you know, I, I do have friends in other cities and States and I do feel close to them, but at the end of the day, like I need to prioritize the people who are actually going to like be in this environment and who, you know, are probably going to be in Austin for the foreseeable future.Cause it’s like, I think that it. It really highlighted how much stronger, like in-person friendships and stuff can be and why it’s better to just focus on those than to try to like travel all over the country. Like having relationships with a bunch of cities and people in a bunch of places. And it’s like, it’s kind of like a awkward or tough thing to say or talk about.But I think that people would just be a lot happier if they like didn’t travel, spend more time in their home.Nathan: [00:19:09]Yeah. And it’s just all about being, being deliberate in that way and choosing the things that, you know, you’re going to focus on. Cause you can’t, you can’t focus on everything.Nat: [00:19:18]Yeah, exactly.Nathan: [00:19:19]Okay. I want to start courses and then I want to talk like. W w w we’ll go to, back to ranch houses since, you know, courses help enable ranch houses.So the, it seems to me from the outside of the main way you monetize your newsletter is through, courses like you have the, of course, on Roam called effortless output. that is, is that the primary revenue driver or are there other things as well?Nat: [00:19:45]Yeah, that’s the primary revenue driver now. So, you know, there, there is other, there there’s a bunch of other stuff, like there’s, a bunch of like relatively high paying affiliate deals on the site. There’s a, I sell my book Notes as like a little like info-product, I’ve got an iPhone app. Like there there’ve been other things, but at this point, yeah, the course revenue just like divorce, all the rest of that.So that’s that kind of like in the last year, just like blew up as the main monetization channel for the site and it actually got another one coming out now focused on like SEO for solopreneurs.Nathan: [00:20:25]Bringing it full circle to what started the Content. And initiallyI want to ask him about the Day affiliates are there, like I don’t hear about affiliates, you know, and, that as a channel, as often for monetization of newsletters, are there some of those that, you know, you can talk about and share, share numbers on.Nat: [00:20:44]Yeah. I mean, there’s an honestly, I guess it doesn’t really come mostly from the newsletter, mostly comes from the site and from SEO. So if we’re talking about newsletter monetization, then yeah. That’s predominantly courses. but there there’s a couple of programs in particular that, I mean, actually it’s really like one that’s predominant, which is web flow.Right? So when Field probably is like 80% of the affiliate revenue, and I just like discovered web flow in 2017 and like really fell in love with it and started like promoting it hard. And they’ve just got like an awesome affiliate program. And my like my philosophy on affiliates is like, I’m never going to.Sign up for an affiliate program or promote something that I don’t already like love and use, but it’s something that I love and use has an affiliate program than like, yeah, I’m going to sign up for it.Nathan: [00:21:38]How much revenue is web, affiliate program driving for you? Like on a monthly basis?Nat: [00:21:43]It’s like a bit over a thousand dollars a month. So it’s like not insane, but it’s also like, that’s nothing to shake a stick at, right?Nathan: [00:21:51]Yeah, exactly. It’s funny. The time, like the things where, like, I have a couple of like, well, optimized blog posts on this or something like that. And it’s like, and that is driving, you know, it’s like half a house payment.Nat: [00:22:03]Yeah. That’s the thing, right? It’s like a, it’s fun to frame that stuff in terms of other things like, my buddy and I used to talk about random little. Affiliate passive income stuff is AAA money. All right. It’s like you you’ve paid for all of your Chipotle A’s for the month off of your like random you to me, affiliate revenue or whatever.Right. It’s like, and if you, if you work on stuff long enough, you know, and you, you build up little channels, right? Like it can get to a sizeable amount of money. I mean, there’s a lot to be said for having one thing that drives say 10 grand a month. But if you’ve got 20 little things that you’ve tried 500 a month, like that’s cool too.And in some ways it’s a little more resilient because if, if one fails, you’ve only lost 5% of your revenue versus if the $10,000 a month thing fails, you’ve lost all of your revenue.Nathan: [00:22:50]What was the reason behind diving into the Roam course, creating a launching that. And then I’m also curious how you price it. If you went with a cohort model or if it’s just always open, like how do you approach that?Nat: [00:23:02]Yes. So it link came about very. I guess serendipitously or randomly, depending on how you want to frame it. I mean, I, from having the newsletter and talking about personal health management stuff and being on Twitter, talking about PKM, I was just like very in that world. And probably like, if there’s a, if there’s a head of that world, it’s definitely Tiago and his chorus building a second brain.And I went through that back in 2017 and you know, I’d been like very vocally supporting his course and everything that he was working on. but I never liked Evernote. And I always had like a lot of struggles with Evernote as the tool for kind of like doing all of that. So when, Adam Kiesling tweeted about Roam in like November of 2019, I was like, Oh, this is kind of cool.Like, let’s go check this out and play with it. And, you know, like immediately fell in love with it. And I already had like my newsletter, right. I already had the Medley. And so I, I shared it in the Medley and I shared it on Twitter and then other people were like, Oh wow, this is pretty cool. And I think just because I’d been sharing stuff, I was interested in and share in like building an audience of other people, interested in personal knowledge management, people took to it very quickly.But it was, and still is kind of confusing and opaque tool. So I had a lot of people asking, like, how do I actually use this thing? Like you say, it’s cool, but it’s not clear at all why this is so cool. So. I was like, all right, well, you know, I’ll write an article about it wrote the article, the article, like hit front page of hacker news and like went mini viral on Twitter and got like, you know, some tens of thousands of views in the first 24 hours.And I was like, Oh wow, okay. There’s like a lot of interest in this. And then I had four or five friends text me saying like, Hey, you know, if you did a course on Roam, like I would take it. Cause like, you seem very excited about it, but I still have like, no idea what to do here. So, that was really the push where I was like, all right.If, if my, like, if my friends who are like, Smarter than me are like asking me for a course on this. Like, that’s probably a good sign. I should do one. but I’m also like, I I’m, I’m somewhere in between like intelligent, lean startup person and like exceptionally lazy, because I was like, I don’t want to do any work on this if no one’s going to pay for it.So, I just like put out a tweet and said, you know, Hey, some people ask for a Roam course, I’m going to do one. Here’s like the initial table of contents. just PayPal me $50 if you want early access. And I got like 50 ish PayPals in the first, like 24 hours, which was like, ridiculous, because it was literally like a yeah, from a tweet and like a picture of the table of contents.Right. So, that was like strong validation was like, Oh shit. Okay. I should actually do this. And also now I have to do this because people have Tape don’t want to just like, do a bunch of refunds. And so, yeah, I spent the next month, like recording everything, getting it out. and then, you know, you asked about pricing or something kind of funny happened then too, which was as I was like finishing up the course.So I, I said PayPal me 50 to get early access. the next day I put up an actual landing page and started charging 75. And then by the end of the weekend, I upped it to a hundred and I said, okay, it’s going to be a hundred while I finished recording all of the content and everything. But then when I release it, the price is going to go up.So that was recording everything and putting it out. and then as I was getting close to finishing it, the, the Roam teams, people who worked on Roam took the course and they liked it so much that they basically subsidized it as they’re onboarding. So they, and this was really funny cause they didn’t even tell me they were going to do this.I just woke up one day and they had put out this tweet that said like, Hey. we liked that score so much that if you take it, we’ll give you a hundred dollars in Roam credits. When we turn on payments, which was like incredible, because that basically made the course free, right. I was charging a hundred dollars for it.They were going to give you a hundred dollars in credit, but it basically pays for itself. and so after they did that, I said, okay, well, I’m not going to increase the price as long as they’re offering that, because it makes it such a no-brainer to buy. So I just left it at a hundred dollars. And I mean, it was, it was crazy.I mean, by, by the time I got, by the time September rolled around, it was wanting to do the second version of it. It had done like two or $300,000 in sales. On a, a hundred dollars a student, which is like a lot of money for, an online course. and especially one that like, you know, in all honesty, I expected to make 10 grand off of, you know, some friends and other nerdy people on Twitter.I definitely did not expect it to have like that kind of reaction. so that was just like, kind of wild and continues to be a sort of wild, thing to have created.Nathan: [00:28:01]When you did the second version, what did you change about it? and how did it change the pricing?Nat: [00:28:06]So the first version, you know, the, the great thing about building in public and doing like the whole lean startup MVP, whatever is that it lets you like validate as you go. And not like build stuff that people don’t want and don’t need the downside is that when you don’t have a plan stuff, kind of just like gets hacked together.It’s sort of like, you know, building like an MVP with like actual code or whatever and you have this like cowboy code spaghetti code, like mess of stuff that needs to go back and you need to go back and clean up later. So version one was very like disorganized and very, like just tutorial, right?It was like, here’s how to do this and here’s how to do this. And here’s how to do this. There wasn’t that much of a like user story through it or like a flow that would, like help somebody like understand the why of the tool. It was just like the, what the, how to do this, this, this. so for V2, it was like, all right, we’re going to do some quick, basic tutorial stuff. And then we’re gonna go through an actual, like a journey of using this app. So we’re going to like pick a topic that we want to learn more about, and then we’re going to do a bunch of research on it.And we’re going to organize our research in our database. They’re going to take that Research or we’re going to like distill it into like our lessons and our takeaways from doing all the research. Then we’re going to create an actual, like project to manage shipping the deliverable that we want from doing this research.And then we’re going to actually create something new from all that research, whether that’s like an article or a script, or, like, you know, some sort of other creative work or whatever. And that seems to resonate with people a lot more. Cause then it was like, Oh, I see why I would use this now versus just like, here’s how to use it.So for that one, Increase the price to two 50 and then also had a cohort-based version for 500 where you got the whole self paced. And then we met once a week for five weeks to go over implementing each of the five sections of the course. and. The cohort went fine. I just didn’t enjoy doing it very much.And it didn’t feel necessary for the type of course. So it was like, I think that if you’re learning, if you’re learning how to do something or how to use something, you don’t need a cohort based model. I think we need a cohort based model four is like when you’re adopting a new identity or doing something that requires feedback and like a continuous integration.So like David’s Write of Passage course is like the ultimate cohort-based model because you can’t do like a self-paced course on writing. Cause you need like social pressure to actually ship stuff. You need feedback on the writing, you need coaching. Like there’s a lot that you need to do that well. whereas like how to use Roam, you can absolutely do self-paced So I haven’t done another like five week cohort, but what I have been experimenting with, which I kind of like, is this a one afternoon intensive?So I did one of these last month. I’ll probably do another one, like next month or something where I called it and building Roam in a day where it was a four hour, like intensive where each hour we did one of the units with like a 10, 15 minute break. And that actually went super well and people really liked it.And it gave me an excuse to update some of the course content. So I might try doing that every quarter or something.Nathan: [00:31:26]You know, it’s interesting as you talk about that, I’m reminded of, James Claire for a long time, when he was building his newsletter, he, he was purely focused on growing the newsletter. You know, he, atomic habits wasn’t out yet. so he was publishing twice a week, you know, and then promoting republishing that content.And we always talked about like, Oh, how are you going to monetize it? And he’s like, ah, I just want to focus on growing total readers. But he did obviously need to make money. And so once a quarter, we would do a live habits workshop. And I think the first couple of times he did it, you know, like maybe the first one made 25 grand or something, you know, but then it got to the point where once a quarter he was doing these workshops and they were making like 250 grand each time just as that grew.And then for the entire rest of the 90 days, he could just focus on growing the audience. And so it was like once a quarter, he would take this little break, go make a bunch of money and then go focus on growth. And it’s interesting. Cause I could see, yeah, you doing a similar thing. Like it just reminds me of with the intensives of like, Oh, if I do this every couple of months, you get kind of this fun interaction with all the students.It’s another reason to like PR to promote, it’s kind of a mini launch of like, or a reminder of like all of them that’s Roam Content. So I like it.Nat: [00:32:47]Yeah. And what I did the last time was I charged a hundred dollars and then you just got like all the recordings and the tutorial. And what I then did is I saved all those recordings into a new course. And so now, effortless output has like a hundred dollar option and a $200 option. So the $200 option is the one that was two 50.And that’s like the full self-paced course, but you can also just pay a hundred dollars for the recordings from Roam in a Day, plus the tutorial material. So it’s like a condensed, like less in-depth version of the course. And that’s actually been working out really, really well. And what I’m thinking I’ll do for the next Roam in a day is basically say that, like, if you’ve taken either course, if you’ve bought outercourse, then you get to watch and join for free.So anybody who’s taken either one can watch it join for free, but if you pay like. 25 or 50 or whatever. I haven’t decided you can actually join live and like ask questions and engage. Because like, with, I think it was something like 4,500 students that have gone through it. Now, like if I try to, if I invite all of them to a zoom that could turn into a master really quickly.So having like two tiers where there’s like an engagement tier and a like watch tier, I feel like is kind of a, a good way to do it.Nathan: [00:34:05]Yeah. And it encourages people or like gives people something where they’re like, Oh, I’ve paid for the course maybe before Roman a Day existed. And so I can, you know, come check it out for free and people will appreciate that. what are you changing next time around as, you know, as you work on this, SEO course.Nat: [00:34:23]Yeah. So one thing that I’ve changed my mind on recently is kind of like pricing psychology with courses. So I think that. I think that you, you can make a lot of money and you can do very well pricing it very high. and I think, especially for cohort-based courses, you have solutions, you should charge a lot, but for self-paced stuff, I’m actually, I’ve gotten more of the mind that it’s better to try to create like a disproportionately incredible course for the price so that there’s no reason.For anyone to recommend any other course. So, there are a lot of SEO courses out there and a lot of them are like kind of expensive, and a lot of the inexpensive ones aren’t like that. Great. Right. so my, my goal is I’m probably, I’m probably gonna do like a two tier structure, just like I have with the Roam course where there’s going to be like a hundred dollars version at $200 version.And for the $200 version, like, I just want it to be like the absolute disgustingly best SEO course out there, where there would just be like no reason for anyone to recommend, like anything else, especially considering the price point. Because I think that once you like, get into that position of like, No, this is just the, of course you take, then that’s where, like you really start to get sort of like the incredible long-term like tail benefits from it.Cause I think that like you, what you might lose in short-term revenue, you gain in long-term Mindshare. And it was this interesting thing where like, when the Roam course was only a hundred dollars, there were like so many people taking it. And so many people talking about it on Twitter that it felt like it was everywhere, right?At least in that like very small niche community. But when I increased the price of two 50, like fewer people were taking it, it wasn’t getting talked about as much. It felt like. It was LA it had less of the mind share. Right. And so I think there’s, there is actually a lot of power in like at least starting very inexpensive building, a huge fan base of people who like, love what you’ve built and then either never increasing it and maintaining that mind share, or like increasing it later once you’ve kind of like established a baseline of a lot of people who really like what you’re doing.So that that’s sort of what I’ve leaned more towards now.Nathan: [00:36:44]That’s fascinating because just as like I got into selling digital products and courses back in 2012, and you know, the common price points were $29, $49, you know, like I had a version of mine that I charged two 49 for, and a lot of that was relatively expensive at the time. Whereas, you know, since then, yeah.Like a $2,000 course is not at all uncommon, you know, and then you, you get some that are cohort based, you know, there might be 3,500 or more in there they’re positioning against like a semester of college, you know, or, or something like that. which I think is great. And, and it’s enabled a lot of things and you can have, you know, a hundred students and make a crazy amount of money, which is fantastic.But I have wondered if it’s going to go the other way as people try to find the sweet spot. So I like what you’re saying about the a hundred dollar, you know, a hundred to two 50 price point and really, I guess all that, what are you optimizing for? And at this point you’re not optimizing for the absolute most dollars per email subscriber or something like that.You’re optimizing for Mindshare and that’s a great call app.Nat: [00:37:54]Yeah. And I think that there’s also this element too, of like knowing, knowing what you’re good at and knowing what you do and do not want to do. And for me, for one, I hate cohort based courses. I can’t stand them. like I have nothing against people doing them. It’s an incredible model. And a lot of people love it and they should do it.I’m like, I just personally, like I’m crazy add, I can’t like say engaged with something for like weeks and weeks at a time. Usually like, I want to download all the information in two days and then run with it. I can’t wait. Write, like I was, I was like the most annoying student when I was in second frame of Tiago.Cause I was like, dude, can you just give me the lectures? Like, can I just watch them now please? Like, I don’t want to wait until next week. Like, I’m surprised he put up with me because it’s a pain in the ass about it. but for me it’s like, okay, I know I’m going to do self paced. Right? Like I’m not going to do cohort.And then if I’m going to do self pace, like what in self pace do I not want to have to deal with? And the number one thing is like support, right? I want to, I don’t want to have to be like always responding to emails. And I think that if you’re like pricing at 500 or a thousand or something for self-paced course, people reasonably assume that you’re going to give them some amount of your time.Whereas if you’re in the like hundred to two 50 range, I don’t think people have that same level of expectation. And honestly, somebody I like look up to a lot in this regard is West boss. because he’s got these. Phenomenal programming courses like 25 hours of JavaScript training for a hundred dollars.Like the, the Delta between the value he’s providing and the value he’s capturing is like insane, but he makes millions of dollars off of his courses. Like the numbers on his site are like honest about how many people have gone through them. Like he’s printing money on those. And everybody recommends him because his courses are incredible and very reasonably priced.Like it’s a, it’s a very, I think underrated model, if you’re doing self-paced to just like, create this disgustingly huge difference between what people are paying and what they’re getting and let that just like, do all of your marketing for you. Like when I, when I put up the presale for the SEO for solar preneurs on Twitter, a couple of days ago, I got a number of people who were applying, being like, Holy shit, only $97, like that’s instant.Yes. Right. And I was like, cool. Okay. That’s like the thing that I’m going for here.Nathan: [00:40:18]When it comes to monetizing newsletters, there’s a bunch of different paths, you know, like, courses, eBooks, all of that has been really common. People have done sponsorships. I feel like a bunch of them are having, different forms of Renaissance, but paid newsletters are really popular right now with some stack and, and ghost and ConvertKit and everything else.I’m curious, you sort of like dip in both worlds a little bit where you’re most, it seems like from the outside, most of your revenue is coming from courses, but then you’re also putting content in not your own pain newsletter. Right. But you’re putting it in the, every bundle. what’s it, what’s the reasoning behind that?Nat: [00:40:57]I mean, I, every bundle, I think is just like a cool right Like I love what Dan and Nathan are doing Uh I think that it’s so I I had wanted to do some sort of paid writing thing And I try to membership for my site That was a mistake Uh didn’t go well for me considered it, for the same reason that I don’t like a lot of core stuff.Like I’m, I’m very good at like focusing intensely for a period, shipping something and moving on to the next thing. I’m not good at maintenance. Like I can’t sustain stuff very well. and when people are like joining a membership that sort of expecting a certain level of maintenance or like engagement or stuff, and like, I.Yeah, those are the things that I hate most are like doing the same thing week after week. Right. Whether that’s even if it’s like hosting a different workshop, like if I have a recurring event on my calendar, that’s, work-related, it’s just like the bane of my week. and so I just, I couldn’t enjoy doing the membership, even though there were cool people in there and it was making good money.Right. It’s like, I, it was, it was doing like a bit over five K a month when I launched it. And after a month, when it started the second month I like canceled it and refunded everyone. Cause I was just like, I’m sorry guys. Like, I just, I’m not enjoying doing this. Like glad I tried it, but it wasn’t the right thing for me.So like that didn’t work. I considered doing a paid newsletter, but then I was worried about the same problem, which is basically like, okay, if people sign up for this for 10 a month, then I have to ship something like every week so that they feel like they are getting their money’s worth. and I’ve, I know myself well enough at this point to know that the minute I introduce that, like incentive structure, I’m going to hate doing it.So, what I liked about every was since this is a collective you’re, if I don’t send something for a few weeks, there’s still a lot of other, really good stuff in the bundle people are getting access to. So I don’t have to feel like I need to ship on a set schedule in order to like give people their money’s worth, because I’m just like a part of a, a broader collective.And so I like that a lot. And I liked it there. Like, it’s, it’s a very wide variety of topics and they’re very like, hands-off with sort of like, just for the most part, letting me write about whatever I want to write about. And I’m also like, I’m definitely the odd one in the bundle and that my newsletter has like no cohesive topic that makes any sense.But that’s also like, if anybody knows my writing, they know that that’s just like who I am. and so it kinda like fit, like it’s good that they were willing to let me do that too. Right. So. It’s just like, I think it’s a cool experiment and I think that they’re going to like grow and it’s going to be cool to like, be in that community and it’s fun.And it’s like, it’s a good, it’s a good link exercise for writing too. Cause I don’t really have anybody edit the stuff that goes on my blog or that goes in my newsletter, but like, they’re very good about like editing and feedback and stuff. So it’s making me a better writer too. which I appreciate.Nathan: [00:43:57]Yeah, I love the structure that they’ve put around it. when Nathan was on the show, we talked a lot about the. Like writing process and editorial and, and how to have that group of people where you can riff on ideas with, cause we all do it, you know, but we do it with a random friend who’s over for a barbecue and we’re like, Hey, we’re like testing out, you know, material for another blog post.And, and so to have people who are like Hey there’s something here but this draft that you wrote isn’t it you know and actually like and say, Hey, if you put a couple more hours into this, it could actually be something that’s, that’s really good instead of like passable.Nat: [00:44:36]Definitely. Yeah. And they’ve got like weekly chats for like workshopping article ideas and people, you know, give each other feedback on stuff they’re working on. and it’s interesting too, because it’s like, it’s, it’s actually a very like politically diverse community. but everyone’s very like respectful.And so we can like, it’s, it’s cool because I think that a lot of publications are, you know, like we’re seeing this with New York times and whatever, like they, they become very politically homogenous. Whereas like so far there’s like a pretty big diversity of like etiologies, whatever, and the people writing for every, and we’re all like, we can, we can disagree very respectfully, like within the discord and like have really interesting conversations about stuff.And so I’m like, I’m hoping that that can like keep up, and it makes the newsletter more interesting too, because I feel like we can write about stuff that, you know, Different people have very different opinions onNathan: [00:45:31]Yeah, how’s the money side of it, of at work. Is it driving, any kind of meaningful revenue for you?Nat: [00:45:37]Yeah, it’s serving some, I mean, the way it works right now, and actually, Evan Armstrong who writes for napkin math, just put out an article on this, on every blog title is something like, am I, am I getting screwed by every, it was like, it was a clever title where he basically, he broke down the math of how like writers for the bundle get paid and whether or not it makes sense.And so it’s like basically you get 50% of all revenue from, people who like sign up and reference you as the reason they signed up. So the bundle costs $20 a month. And everybody who signs up either through my publication or who say that, like I sent them, I’m getting $10 of that revenue. So I think I’m making a bit over two grand a month from it right now.And I think that like, if I, I am, but I’m also like, not that great about writing as consistently as everyone else. so if I like do a better job of that, and honestly, I think that if I decide on a topic to focus that newsletter on a little more deliberately, that’s going to help with it too. Cause it is hard to know if it’s worth subscribing to something when you’ve no idea what you’re getting.So I’m playing around with a couple of topics to try to like narrow in on over there and then leave my like other Medley of ideas for the newsletter and personal site.Nathan: [00:46:51]What’s interesting to me about that is it’s like half a, your own paid membership or, you know, paid newsletter and half affiliate at that point. Right. Cause going through your have um you know like there’s several posts that you click into and it’s like here’s the start of it And then go read the rest of it on every um and so that’s like you know it’s just like go read the rest of it on my paid newsletter But even if you know a few years from now I imagine if you like were ready even less consistently for every you’d still have what’s effectively affiliate links driving traffic over and Hey, that recurring subscription.That’s interesting.So let’s talk about some of the things you’re doing offline.One of my favorite things is taking, I think Ryan holiday and I were talking about this at one point of taking like internet money and turning it into tangible, real life things. what are, what are some of your favorite, you know, real world uses of, of internet money?Nat: [00:47:47]There’s like, and this goes back to the COVID realizations about like better living. I mean, just spending time outside and away from screens. It’s like, I, I, and I think this is a fairly common sentiment at this point. It’s like time behind screens is to pay for more time away from screens at this point.So. Like with, you know, during COVID, my wife and I bought like a really nice, like five bedroom house, about 45 minutes outside Austin. on six acres, like in this sort of dense wooded area with this like huge like wraparound porch and just like a perfect house for like getaway parties and cookouts and stuff like that, and built a big fire pit.And we’ve got like three different grilling apparatuses out there and just like the ideal spot for everyone to like go and enjoy being out in nature. And I think that’s been like one of the biggest, like good investments in like quality of life that we’ve made. I think that like too much gets lost in the, in the financial optimization discussion.Right. Where. You know, you’d probably hear somebody say like, Oh, well, you know, it’s actually a really bad like investment to buy a vacation house because you could invest that money in like index funds. And then you could just like rent an Airbnb whenever you want to go do that. And it’s like, yeah. But like, then you’ve got to like find the Airbnb every time and it’s like, not exactly how you want it and you don’t have all like the grill stuff you want and you don’t like, there’s just so many downsides to that model that kind of like get lost by just over optimizing for return on capital.So, we’re, we’re like very pro you know, investing in like ways to enjoy life with friends, outdoors, and been like a lot of little things like that. I mean, also during COVID we like. Did a big renovation on our backyard in terms of like building out a big deck and everything. I got a sauna for back there, which I’m using like almost every day now.And it’s awesome. I moved my whole desk outside of it, which is like another awesome quality of life improvement. And it’s raining today, which is why I’m like recording this in my kitchen. but like that, I mean, that’s such, it’s been great. and I think that like, it’s really easy to forget how much better it feels being out in nature and having that clean air and that like healthy environment and everything.Until you like get back out there and remind yourself, because it’s like, it’s something about being in the city and like being in work mode, you forget how much better you feel when you’re out there. And then you go back out there and you’re there for even 20 minutes until like, Whoa like this is, this is how I should feel all the time.Like, this is better. So how do I get more of this? And how do I remember to go get more of this? Cause it’s, it’s again, it’s really easy to forget when you’re in that like downtown work mode.Nathan: [00:50:42]Yeah, I’m, I’m optimizing for many of the same things of like, you know, this evening after work, I’m going to go plant a two acre field with pasture grass, because I’ve got the, the seed spreader, you know, hooked up that I borrowed from a friend hooked up to my tractor and, you know, we’ve got like, I don’t know, 50 pounds of seed and, you know, that’s what we’re gonna do this evening.And it’s exactly that of like taking a phone call or something. And like, I can go, go for a walk and like, not even leave my own property, you know, as I’m like wandering around talking on the phone or, or anything else. And so it’s really fun. And then like, you’re talking about as well, having the space to invite friends over, you know, and, and like have the spare bedrooms of like, Hey, come visit.There’s there’s plenty of room for everybody.Nat: [00:51:29]I mean, it like socialization and like spending time with people is completely different when it’s, Hey, come have dinner and hang out for like six hours or the night. And, you know, like really spend a chunk of time together versus what we normally do, which is like, Hey, let’s go meet for an hour and a half dinner and then like run off to our next commitment.I think that you can actually get a lot closer, a lot deeper with people and like a single, you know, six hour long hang, then you can get in, you know, months of occasional dinners and whatnot. it’s like, it’s a, it’s a very different way of spending time with people. And I think just like so much more enjoyable.Nathan: [00:52:11]Yep. It’s good. we have now I guess, between the two properties that we bought and side-by-side, I think we have like eight. Spare bedrooms from like various houses you know, we can rent out on Airbnb. And so one of my goals is to just have, have more people come visit and stay. And we have a lot of work to do on this property as far as like, you know, there’s crazy amounts of bare dirt, everywhere, lots of trees to plants and all that.But that’s, that’s part of the fun.Nat: [00:52:38]That’s awesome. Yeah. And it’s like, it’s fun doing the work too. It’s very satisfying. It’s a different kind of satisfying from like working online.Nathan: [00:52:46]Still at the same creative mindset, it just is applied differently when you’re, you know, outlining a Roam course versus building a fire pit.Nat: [00:52:54]Yep.Nathan: [00:52:56]Let’s see, on the other side, I’m curious about things. Well, so from following you online, you have this interesting balance between like lots of things that are optimized, Write being the rum, Roam Research guy, you know, you’re, you’ve got all the systems dialed in, you know, I remember you talking about.You, I, I think you and your wife talking about perfect pitch, you know, and you’re like, Oh yeah, I have an article somewhere. You know, like, let me go dig it up. You know, I’ve researched this and like how to develop, how kids can develop perfect pitcher, you know, any of these things, right? You have extensive research and, and things that are heavily optimized.And then you also have like this whole other side of your life where it’s purposeful under optimization, you know, where, you’re either saying like you’re getting out of your agency and stepping back from that, you know, you don’t strike me as the person. Who’s trying to make the most amount of money in every area of life, or so I’m curious, how do you think about that?What are the things where you’re like, this is what I’m going to have dialed in, and this is the area where maybe you’re even actively preventing yourself from, optimizing some of those things. Yes.Nat: [00:54:02]Yeah. I think a lot of it comes back to, for lack of a better term, just like being kind of stubborn and like selectively lazy in the sense that I think that, I think that when I was a kid, you know, my parents would always say like, well, you’re going to have to do stuff that you don’t want to do. And I think there was part of me that was like, I’m going to show you.Right. Like I bet I can figure out a way to like, not do most of that stuff. and I think like realizing that the point of accumulating capital was to like, Design your life in the way that you want it. And not just to like accrue more capital, it was like a very helpful realization in maybe in college or something.I guess I had a lot of friends or peers who were going into these like wall street careers, where they were working 60, 70, 80 hour weeks and making great money, but just like being miserable. And, you know, I started down that track and then realized like, yeah, I don’t think this is for me. I’d rather like, you know, control my time more and get to do what I want.And I think that’s just always been like a very helpful driving force for me, where it’s like, I’m not going to optimize for like dollars in the bank. I’m going to optimize for, you know, free time on the schedule and like the ability to do whatever I want to do, work on what I want to work on. Right. It’s like I’m spending probably six hours a day right now, just like programming and learning more coding and development and learning about crypto and stuff.Because like, that’s what I’m really curious about right now. And I think that I like. I can do really, really good work and I can make really, really good stuff when I’m very interested in it and very like compelled to do it. But the minute someone like tells me to do something or the minute I feel like I have to do something, my like quality of output and everything just like goes through the floor.And I’m like, like, I’m the worst possible person that you could hire. and I think that like accepting that about myself and trying to like work with that, being my personality instead of like fighting it and trying to. You know, operate in the normal ways was like very, very helpful for like, you know, both work success, but also like psychological health Riley.I think that for basically all of high school and early parts of college, I thought that there was like something wrong with me. And I was like messed up because I didn’t care about grades and I couldn’t focus on schoolwork and, you know, like I thought this was dumb and didn’t like it, and you know, it was just like always this source of tension in my life.And once I kind of said like, like, fuck it. I’m just going to figure something else out. It, like, everything just went a lot better. So, you know, like even even dumb stuff now, right? Like it’s like, yes, I should. You know, obviously I have the time to like do my laundry and clean my house, but like, I don’t want to.And, and so we like hired a nanny who comes and helps us out, like once a week and, you know, like, Takes care of all, all of that stuff. And it’s just like being very okay with, not with optimizing, for like living in a way that’s like in line with how my brain works versus trying to like maximize, you know, finances or like, you know, do what you’re supposed to do or whatever.I think it’s just like, been very, very helpful. So I try to just like focus my time on the very few things that I’m legitimately good at and can actually focus on versus like trying to do everything right.Nathan: [00:57:37]Yeah, that makes sense. A question that comes to mind for me is, is balancing. Like not wanting to have commitments or be told what to do or that sort of thing, which I can very much relate to with like, pre-selling a course, you know, some people have this problem where they, I think Derek Sivers talks about like, not telling people you’re going to do something before you do it, because you’ve gotten part of the dopamine hit saying like, I’m going to do the same because like, wow, that’s amazing.That’s so cool that you’re going to do that, you know?And, but then you haven’t, you know, you haven’t done it yet. and so, especially when you’re, pre-selling something right, you now have this obligation. Is that not a problem that you run into? Are you able to like, just power through and, and meet the obligation or does it trigger some of those feelings?Nat: [00:58:22]No, that’s a, that’s a really good question. and I think that the reason it works is that it’s an obligation I want. Right. It’s like, I, cause it’s funny, like at the same time that I’m really bad at doing things I’m told to do. I’m also really bad at like, Shipping stuff. If there isn’t some reason to ship it, if that makes sense.So like, I respond very well to peer pressure or like having other people who are committed to the same things as me. So I find like, you know, workout buddies, like that works very well or committing with somebody to, you know, doing something for a month, whether that’s, you know, not drinking or like whatever, like that all works very well.And I think that’s because those are commitments that like I want and things that I want to do, but I might not have enough like willpower or focus to do on my own. So, you know, with the course stuff, like I’ve been talking about doing an SEO course since January, and it was on my like list of things to do this year.And I like had even I’d put out a tweet of, like two months ago saying like, Hey, I’m gonna do this sign up for the email list to like, know when it comes out. But like, none of those were enough to actually like get me to sit down and do it, whereas like. Something about collecting money is a very, very effective, like stick, I guess, for actually like making the initial progress.I think that like part of it is it’s something that I want to do, but it’s very easy to procrastinate on because it’s like, Oh, I can always do it later. I can do it later. I can do it later. But once I’ve like put a line in the sand, had some people commit to it, then I can like make a lot of progress really quickly.But you’re you’re right. That’s kind of like a funny, like, comparison or like example, or I don’t know what the exact term would be, yeah, yeah, yeah. It’s like this weird dichotomy I can’t do. I can’t think of things that other people tell me to do, but I can do things that I tell other people to tell me to do.Nathan: [01:00:26]I think we’re all or everyone who has creative output and is working in that way is, is looking for like, how can I like through crafting my environment, my friends, you know, understanding my own motivations and all that. How can I like harness this mind and body into doing the things that I want?Like did I say I want to do, but are actually hard, you know? And so it sounds like you’ve found a lot of those of like, for you, that is a tool that works, you know, you build up this momentum of like, okay, I want to do this now. I need a reason to do it now instead of, you know, later this year or next year or never.Nat: [01:01:06]months. Yeah, exactly.Nathan: [01:01:08]Yeah. That’s good. as, as we wrap up, I’m, I’m curious a bit more your relationship to goals, and maybe I’ll go with a different question. our friend clay Aber has a question that he likes of, if we were to meet a year from now with a bottle of champagne, What would we be celebrating? And so I’m curious to hear your answer to that question.And then I’m also curious for you to know more about how you set goals. And if you do.Nat: [01:01:35]Yeah. I mean, it would, it would be slightly late, but we’d probably be celebrating, my wife and I having our first kid, you know, I think that was like the most important thing to focus on for this year. and it’s, you know, I think once, once you decide to focus on like family and like community and building that, like all of the work stuff really just feels like it’s in support of all of that.So, you know, that, that was like number one thing, I think on the list for this year. And, you know, we’re, very lucky that we’re expecting in October. So, really looking forward to that. And, I think that would be like the number one thing, you know, there’d probably be other stuff too, but, you know, like our daughter’s not even here yet, but I can sort of already tell that it’s just like, all of the other work goals are gonna kind of like fade in comparison. and it’s one of those funny things too, where it’s like, if you’ve spent your whole life focused on or your whole life up until this point, right.Which hasn’t been super long, but as long as it’s been focused on work goals, then you, on the one hand, you’re sort of like, Oh, I’m gonna like lose motivation. And Dr. once I have kids and like, that’s bad because work is good, but it’s like, no, that’s good. That’s a healthy thing. Like, you’re your end all be all like incrementing numbers in like a database somewhere.There should probably be stuff in the real world that’s more important. So I’m excited about that. And I think that that’s going to be like a really just like awesome change of like life and energy and like, and unfortunately I think it’s like something that. A lot of like young, ambitious guys don’t like, or could probably focus on earlier and be happier with Write.And like, I don’t want to tell anyone how to live their life or whatever. I just, like, I think that I I’ve, I’ve never, you know, you don’t really hear people in their sixties, seventies, eighties saying like, I wish I had kids later and spent more time focused on Right. Like maybe there probably are some people who feel that way, but it’s much more common to hear the opposite.Right. So, I’m, I’m, I’m pretty excited about that. And I think that’s probably be celebrating.Nathan: [01:03:49]Yeah, that’s good. And we, to bring it back to what you’re talking about of, you know, some COVID changes, and benefits that came from, from that for us. we had our latest kid, let’s see, January 1st, 2020. And so I would have spent, you know, I would have done a couple of team retreats. I would have, you’d like every conference request, you know, it’d be like, Oh, I, you know, how much business will this do if I go speak at this or that.And I just had none of for the for an entire year Uh I was like the whole first year of his life I was there you know every day And that wasNat: [01:04:29]Awesome.Nathan: [01:04:31]And so yeah, you end up with this, a different focus on priorities.Nat: [01:04:36]And also it’s like, Oh, to, to your point earlier about just like having random articles and stuff about things, it’s like, Oh, this is what all that research is for. Right? It’s like, this is why, this is why I care about health stuff so much. Right. This is why I care about education stuff so much true. It’s like, The, like I’m I’m so I’m so jealous that she gets to grow up in this world where we have so much more information and like, know how to do so many more things and like understand certain things so much more than we did, you know, almost 30 years ago when I was born.Like, that’s pretty cool. And I’m like excited for her for that.Nathan: [01:05:10]Yeah, that’s good. Well, let’s leave it there. Where should people go to sign up for the Monday Medley and, and check out all the things you’re doing.Nat: [01:05:18]The best spot to go, just be NatEliason.com. that’s where pretty much all of the content. You’ve got the newsletter sign up on the homepage there. And then I’m most active on Twitter. If anybody wants to hit me up just twitter.com/NatEliason, since it’s really the main social media I use.So, say hi there and let me know if you enjoyed the episode.Nathan: [01:05:40]Sounds good. Thanks for joining me.Nat: [01:05:41]Yeah. Thanks Nathan. Talk soon.

Ann Handley is the founder and Chief Content Officer for MarketingProfs, a marketing and training education company with more than 600,000 subscribers. She is a well-known public speaker, and has been writing a newsletter called Total Annarchy for the last three years.Ann is also a Wall Street Journal best-selling author of Everybody Writes: Your Go-To Guide to Creating Ridiculously Good Content, and Content Rules: How to Create Killer Blogs, Podcasts, Videos, Ebooks, Webinars (and More) That Engage Customers and Ignite Your Business. Ann was named a top thought leader by Forbes and one of the seven people shaping modern marketing by IBM.In this episode, Nathan and Ann discuss: - Tiny-house offices - How to connect with your audience and grow your email newsletter - How to grow your social media following by mastering the algorithmsLinks & Resources Jeremiah Owyang Nat Eliason James Keller ClickZ FanBridge Rally Ann Handley’s Links MarketingProfs Personal site: annhandley.com Ann’s Newsletter: Total Annarchy Twitter: @annhandley Episode TranscriptAnn: [00:00:00] The notion of voice is essentially how you sound. It’s important to read things out loud. It’s a thousand little choices that you make all along the way that over time, grow your voice and add up to something that’s wholly unique. Find those small moments. Those small moments are the things that become a big differentiation for yourself. Nathan: [00:00:27] In this episode, I talked to Ann Handley. Ann is the Chief Content Officer for MarketingProfs. She’s been around the content marketing online business space for a long time, since 1999. She’s been writing a newsletter for the last three years on a lot of really interesting things. She’s also a really well-known public speaker.So in this episode, we talk about a whole range of things like what she thinks of the multiple rises of email newsletters over the years. The trend email is dead. The balance between email and social media platforms. We get into algorithms. We talk about really a whole range of things. Probably my favorite is when we get into talking about style and voice and how you write, how to make things fun. Her newsletter is called Total Annarchy.Annarchy, it’s spelled like her name. And so you can see if that gives you an idea of the way she likes to write, the energy and passion that she brings to a business and marketing topics. So, anyway, with that, I’ll get out of the way and let’s dive into the show.Ann thanks for joining me.Ann: [00:01:28] I am delighted to be here. Thank you for having me.Nathan: [00:01:30] So I want to start with something that has nothing to do with email newsletters, and it is just a shared love that you and I both have that I discovered in research and that is for tiny house offices.Ann: [00:01:41] Oh, really?Nathan: [00:01:43] Yeah, so I’m in my tiny house office that I built a year ago. I got it finished just before COVID which was good timing. If I understand correctly, you had a tiny house office built, like six or seven years ago.Ann: [00:01:55] Yeah, this is it. Yes. I was, it was, turned out to be a prescient move because who knew? This is very, so I’m in my tiny house office right now. It’s in my backyard. and yes, I built it, oh, six or sevenish years ago, something like that. And I built it at the time as a sort of place where I thought I can come and do my best work.It’s, you know, small enough that it’s just me in here, me and my, and my little dog who’s here with me now. Little tiny porch on the front and a hard wire internet connection. And that’s it. So I built it as a place to really, as I said, do my best work as a place to write, essentially that was just sequestered from everybody else that, that I couldn’t hear anybody breathe back here. It was just, you know, a hundred percent perfect. And then, you know, fast forward COVID happens. And suddenly my tiny house is now thrust onto the international stage. It’s, you know, now the backdrop for all of these online programs that I’m doing, which is fine.Just that I kind of had to clean things up a little bit. So, so yeah, its kind of been forced into that, the white hot lights of the internet suddenly and the tiny house it’s doing its best back here, but this is not necessarily what it was before originally.Nathan: [00:03:13] Yeah. So it started more as like sort of the writing shed, backyard office kind of thing. And now it’s the working full-time.Ann: [00:03:22] Yeah, exactly. I mean, you know, so MarketingProfs, my company, we’ve always been a hundred percent virtual, so I have a, an office in the big house where I lived. A lot of people think I live in a tiny house. I do not live in a tiny house. It’s a tiny house office only. So I live in a regular size house and I have an office there too.And, and I use that mostly, you know, like in the, in the deep winter, it, this place is not insulated. As you can tell by the plywood background here again, this was supposed to be just for me. I didn’t understand that this was going to be, who knew it was going to be a subjected to the internet on a daily basis at this point.But yeah, so it’s, it essentially built it, you know, for me, this is a place to, to come back when I really just needed some space and some quiet. It actually turns out to be probably, like the best investment I ever made. As a writer, it’s just been such a gift to have this place back here.And you know, even in pre pandemics times, that was true. But especially now, because it does feel like it’s a world away from anything going on, not just in my house, but in my town and my state and my community, anything beyond it, you know? So it’s kind of nice just to have this one, place that as a writer, as a creator, you can feel like, all right, it’s all mine.Oxygen is back here, you know?Nathan: [00:04:43] I like that. Yeah, for me, I, my tiny house office is just across the backyard, from my house and, and I have three little kids, and so getting outside the house, my old office is now our one-year-olds room and like, he can have that space. I can have this space and it’s perfect. So I think we’ll see a lot more people that build out tiny house offices or, you know, backyard things.It’s a good trend.Ann: [00:05:12] Yeah, exactly. And in really creative ways too, like my friend Jeremiah yang has it is a digital consultant. he speaks a lot about, you know, what, what’s next, the future of, of digital. Of the digital evolution essentially. and he put an Airstream in his backyard that he retrofitted with, you know, as, as an office.So, you know, there’s all kinds of different ways to do it. We did a clubhouse a couple of weeks ago. Jeremiah and I did in which we, we had people, you know, we invited people to talk about their own sort of backyard offices. People have crazy stuff, you know, not even. You know, structures like, like iron man or what looks like, like you’re in like wooden structures, but, you know, in addition to Airstreams, they have tents.They have, you know, sheds that have been repurposed. I mean, all kinds of crazy things. so yeah, it’s definitely, definitely a trend.Nathan: [00:06:02] Yeah. I have a friend Nat Eliason who has a space out in Austin, Texas, and he’s set like permanently set up. Is his office on his back deck, you know, I guess it’s, I hope it’s covered. I don’t know. I mean, you know, but like he’s like wiping the dust off his monitor and getting to work in it, you know, I like it.And then, James Keller, who’s our VP of product at, at ConvertKit. And she was at, working on the Firefox team before joining us. But she does the same thing where she like camps out on her back deck, like as much time as possible.Ann: [00:06:34] Yeah, that’s awesome. Yeah, I’m in Boston. So that’s a little tricky to do, except for, you know, certain months of the year. and for me it doesn’t solve that problem of like, in some ways that puts me more in the middle of everything. And I think that, especially in the, you know, in the midst of a pandemic, but even, you know, even going beyond this.The nature of, you know, as we’re thinking about offices a little differently now, just having a place where you can do some focused work, I think is just so important right now. And as much as I appreciated it, pre pandemic and I never. I, I didn’t quite appreciate it at the depth that I do now, because just being in this space, just, you know, it just feels, it feels so good.And I encourage anybody who is a, a writer, a creator, anybody who does focus, work of any kind, which is basically, you know, any knowledge worker just think about, you know, how do you create the sort of environment for yourself? For me, it’s really been a game changer.Nathan: [00:07:26] Yeah, I love that. Well, I want to ask about something that’s maybe a little bit selfish for me, which as the podcast interview I’m, I’m allowed to do, in the handbook, you have this interesting world of your own newsletter and then you also have Marketing products. Can you talk about the intersection between those two things?And part of the reason I ask is I’m in that same space of like ConvertKit is a much bigger company than, you know, me individually, but then I also have like my own newsletter and podcasts and often kind of try to figure out the interplay between those two things as they definitely serve each other, but then are sometimes unrelated.Ann: [00:08:03] Yeah. Yeah, that’s true. yeah, it’s something that I’ve actually thought a lot about. So, you know, I’ve been at Marketing profs, I’m partner in MarketingProfs. I’ve, I’ve been with the company almost since day one, since 2002. So. That’s like what, 19 years that I’ve 19 years, this spring, that I’ve, that I’ve been part of Marketing profs.And then prior to that, I, I I’ve had a startup called click z.com, which some people still remember, it’s still around, still offering online marketing advice to, to, all kinds of businesses. So I’ve been in this space for a very long time, you know, associated with a brand that was kind of bigger than me, essentially.So a bit of MarketingProfs, as I said last 19 years. And then, you know, the thing that happens as you go further, along in your career and not necessarily, you know, 19 years into it, but I think it happens, you know, pretty quickly as your, as your, as the company you’re with grows. Is that when you start touching things less, like when I first started at MarketingProfs in 2002, The newsletter was me.Any content on the website was me. I was the chief content officer. I touched every single thing I literally was, you know, putting together newsletters and sending it to our production person so that she could then, you know, mail it out to our list. I was touching it. All of it. and then as your career goes on, like I touched it less and less and less.And I found that it was, in some ways it was great because it freed me up to do more, you know, higher level things to more strategic things. But at the same time I touched it less. And so I got out of that day-to-day grind, so to speak. And I mean that in a good way, like, I didn’t know what it was like to really be in the trenches as a marketer, putting together.Things that, you know, that are, how do you grow an audience? And, you know, in, in the modern age, I mean, I knew what I did in 2002 and three and four, but like, so to stay relevant, to stay sharp and to also just stay in it, because that’s the fun part for me, you know, like as much as I love the strategy piece and, you know, the, the thinking piece and the managing piece and all of that stuff.At the same time. Like I love making things. I love touching things. And so I thought to myself, you know what I need, I need a little bit of a reboot, right. I need to do things on my own. and so nevermind the fact that I had, you know, books and I had a speaking career, like all of that was fine and great and going, well, I didn’t necessarily need in this case a newsletter.Right. But I wanted something that I could make. Like, I just felt that real need to do something right. And to communicate with an audience. I miss that one to one community. and so three years ago I thought, all right, what can I do? And so, you know, I thought maybe I should do something where people can see my face.Like maybe I should do a podcast like this, or maybe I should do a high-spec live regular series, or maybe I should do an Instagram live or any number of things, things that I could have done. and now of course the choices are even bigger. Right. I can just do like. I can do a clubhouse room. I can do, you know, all kinds of things are all kinds of channels, but I realized that essentially I’m a writer and my background is in newsletters.It’s in writing. And before I was in marketing, before I was in newsletter, I was a journalist. And so. Building an audience and thinking about what does an audience need for me is kind of in my DNA. And so I wanted to do that. I thought, you know what, I’m going to do that. And I’m going to find out what is it like to build an audience now?What does it take to. Put together a program, like how do you actually work with an email service? Like I was so far out of it, you know, that I just didn’t do that anymore. and so it was really fun. I actually have learned a whole lot about w w what does, how do, how do you connect with an audience these days?And just to go back to your original question about, like, how do you balance the two, they very much feed into one another, you know, if you are on my Ann Handley, Total Annarchy list, You see that I reference my work at Marketing process. It’s not a, a publication of Marketing process. Like it’s, it’s not a mouthpiece for it, or just another channel for marketing process, by any stretch, it’s all mine.But there are some things that are, I think would be interesting to my audience. The other differentiator is that MarketingProfs is a, you know, we have an email newsletter that we publish three times a week that it’s squarely focused on. B2B digital marketing of all kinds. So you can be an event marketer at, at, I don’t know, Cisco, or you can at the Adobe summit and you can subscribe to the MarketingProfs newsletter and find something there for you.But you wouldn’t necessarily find as much of that in my own newsletter, because my newsletter focuses on almost exclusively on writing on Content and on just, you know, the things that bring me joy. I got, I got a, a note this morning from a subscriber who recently lost her job. And she said that she, he was recessed to resubscribing with her personal email address because she lost her job.And you know, that email address obviously was going away and she said, I subscribed to, you know, learn from you obviously. But she said, the real reason that I subscribed is because you bring me joy. You make me in a good mood whenever I read your newsletter. And I just thought, God, like, how do you put a metric on that?You know, you don’t necessarily get that on the marketing process side of things, because. That’s not the intent, but that kind of is the intent on my side of things. so that’s kind of a long-winded answer, but I think the two feed one another, not necessarily in, in a direct way, but some actually that’s what true sometimes in a direct way, because when you sign up for my email newsletter, it says like, here’s what you’re going to get here.If you’re looking for more general marketing advice, you might consider signing up for MarketingProfs. And I have a. you know, a subscribe link there as well. So it does, you know, feed MarketingProfs to some degree. but you know, my focus is much narrower. I only publish every other week it’s fortnightly.And so just the, the, what I do is different. And from a psychic standpoint, for myself, it’s so important to me just to be able to stay in the game, so to speak.Nathan: [00:14:13] That makes sense. So you talked about coming back into the, like building your own audience world three years ago. I’m curious. What were some of those things that either surprised you or really stood out to you as having changed from previous this time that he’d done it?Ann: [00:14:28] You know, we grew the MarketingProfs list a lot through co-registration. So through partners essentially. You know, the Marketing prevalence is massive. It’s 600 and something a hundred thousand. I mean, it’s, you know, it’s a big list and it’s also been around for, you know, 20 years. Right. So it’s a, it’s a legacy product at this point in terms of the list.So it’s pretty significant, but we were able to grow it way back then from co-registration deals with, you know, some, some partners at the time, some of whom were, are still around. I didn’t do any of that this time because. For a couple of different reasons. but one of the reasons is because I, I.I wanted it to be, I wanted to grow the list more organically and I also just wanted it to be a relationship with me, ultimately, that would grow that list. And so, you know, in that, in that way, a co-registration deal with like, somebody like you, for example, like say that you said, you know, someone sign that sign is signing up for, you know, Nathan’s list.And then you’re like, Hey, you might want to check out Ann Handley too. It’s like, I don’t want that because to me that’s not. What I’m all about, you know, growth at any cost is kind of not a metric that I, that I want to pursue, or it’s not a strategy that I want to pursue. It was different, you know, 20 years ago on the marketing process side of things, where we did want to grow quickly and get as much traction as we could right away.So that was one of the things that changed. I would say that another thing that’s, that’s changed, at least for me personally, is that I, you know, I don’t use pop-ups or, or anything like that as a way to entice people, to sign up for my list. MarketingProfs does it, and I’m not saying there’s anything wrong with it.There’s a lot of brands that do it and you do it quite effectively. But again, it goes back to the goal, right? Of like, what am I all about here? I don’t think that that works with my brand, you know, so those are just, it’s not necessarily something that’s changed, but I think it was a shift in me personally, where I realized, well, yeah, just because it works doesn’t mean that I want to do it because when I put it through that second filter of, okay, so what, number one, you know, it works number two though.Do you want to do it, you know, does it work with you? and. So adding that second filter on like, was, it was an important takeaway for me. Like I, I wanted to be able to run things through that before I made a decision about anything.Nathan: [00:16:46] That’s interesting. Cause I’m realizing I do the same where if I was giving advice, I would tell people you should have, like a lead magnet or an incentive for people. Join your list. Don’t just say like join my newsletter. I send it every week at this time or every other week at this time would be like, you know, give them something right then.But if you go to my own site, I’m like, join my newsletter. I send it every Tuesday because I want people to opt in for the newsletter. And if you need more enticement than that, like where you’d sign up to get something for free and then like kind of lose interest. I actually don’t want you on my list because it’s like, look, I just want a small group of people that really want to be here.Whereas five years ago I wanted as many people as possible.Ann: [00:17:27] Yeah. Your goals are different. Right. And so, yeah. Yeah. I a hundred percent agree with that. Yeah. I mean, I think, you know, it, and it comes down to what are the goals that you have in mind for your own, for your own growth. And, you know, for me, it’s, it’s, it’s a little bit different than it is on, on the MarketingProfs side of things.And part of that is, is it’s like it tracks back to the business model, right? I don’t. I’m not doing anything with the Marketing, with, with the Ann Handley list, other than, you know, communicating with an audience, testing, some things, having a little fun, seeing what works, seeing what doesn’t, you know, using it as a so-called thought leadership opportunity for me.Keeping in touch with my community, nurturing those relationships. Like that’s, that’s all I’m doing. you know, I don’t have advertisers that I need to satisfy, so I don’t necessarily need a certain size of a list or a click through. I don’t need certain segments. I don’t need, you know, people in North America who work at companies of over 500 people.Like I don’t need that. It doesn’t matter. So, so really my goals there are different. And again, like when I go back to. But when we go back to like, why did I start this? I started it because I wanted to see what works. And I also just wanted to be creatively challenged and I wanted to be creatively engaged.And so those are, you know, those are very different goals than actually building a business around it. which isn’t it isn’t to say that this is not a business, but you know what I’m saying? It’s just like, the focus is a little bit different.Nathan: [00:18:55] Yeah, that makes sense. So you have over and you say it, you say 21,000 people on your newsletter. That seems like the sort of number that I would put on there and then forget to update after a long period of time.Ann: [00:19:08] Oh, wow. Is that on the newsletter?Nathan: [00:19:14] Do you have more than that now? Is that a little LOL automateAnn: [00:19:17] Yeah. It’s about, yeah. It’s like more than half that, I mean yeah. More than twice that, I mean, wow. That’s crazy. Where is that? Is that on the newsletter page?Nathan: [00:19:26] That is on at the end of every post, your suggestion form that says get the letter 21,000 people love to get. So it could be that you have 42,000 people, but only 21,000 people actually love it.Ann: [00:19:38] That’s what we’re going to. Yes. Yes. That’s what it is. That’s intentional. Yeah. Yeah. The other 20,000 or like take her to leave it. Yes.Nathan: [00:19:48] So I’m curious what, like that’s a sizeable list? well, I mean, I’m curious what has been working to grow that? What are the channels that have been driving the most growth?Ann: [00:19:58] Channels that drive the most growth for me are essentially current subscribers. When I, at the end, at the end of every newsletter, I say, if you’ve enjoyed this, you know, pass it along to someone else who will also enjoy it. So essentially asking current subscribers, so referrals from current subscribers, second thing is, speaking opportunities.So whether I’m speaking directly about email newsletters or whether I’m just, you know, giving a talk about Marketing, I always say like, you know, if you, it’s a soft, soft approach, it’s like, if you liked what you heard today and you want to hear more. you know, here’s, here’s a way to hear from me every other week.And, you know, I always add a, you know, let me know if you like, how you, how you got here, let me know that you were at this event. that’s the other way that I do it. and then thirdly is through referrals, not directly of the newsletter, but people talking about it on social media. So sometimes it’s me, but more often than not, I kind of forget that I should be promoting this.Which I know is like so lame, but, but again, it goes back to the goals. So it’s other people who, you know, we’ll, we’ll talk about how much value they get from it or how much they love it. And so that’s essentially how it’s grown. So through direct referrals, so the newsletter itself. Through speaking opportunities or podcasts like this one sometimes as well.And then the third, the third way is, my dog is like, wants to get outside and I’ll let him out in a second. the third way is through, you know, social referrals from, from other folks.Nathan: [00:21:33] Okay. So you’ve been around the newsletter space for a long time. And so you’ve probably heard like email is dead. Well, my favorite graph is like all of them. The rise of email, like shown over time. And then with all the email is dead. news articles, you know, like New York, times 2014, I was 20, 2018, whatever.I’m curious about your take on like the recent popularity of newsletters in the last, 18 to 24 months with the rise of sub stack and so many journalists leaving to, start a newsletter, whether on sub SAC or on any other platform. what’s been, what has it been like watching that change? and then what do you think, is it one that’s going to stay or, or do you feel like it’s, you know, just another fad in the moment and in a long trend that will continueAnn: [00:22:21] Yeah. so first of all, I was, so I, I did a. Webinar last week with an email service provider. And as part of my research for that, I was talking about, you know, the, the future of newsletters, essentially. And as part of my research for that, I went back to the very, very, very first, email newsletter, or I should say email marketing, column that I launched on click Z in 1999.And. What I, I saw, I found it on the clicks, the website, and it was all about how, like we’re launching this brand new column. It’s going to be talking about email marketing and. How marketers should really be paying attention to this channel, and the, the language. And it was really funny. I can send it to you.If you’re interested in sending it, just to add to the show notes or something, but the language in it is like, think about your own behavior. It was like, remember, this is 1999. So. Pretty social media, you know, pre, pre blogging, mostly like there was some blogs around, but not really, not quite as much.And pre just everything like that. We think about now, the world seemed like it was so much quieter, but even back then, I was kind of making the case for email marketing. And I was saying like, thinking about your own behavior, like, will you check before you go to bed at night? What do you check first thing in the morning or within an hour of waking up?And I was making the case for the importance of email. And when I read it, read it, read it last week, I was thinking. God, I could have written this, you know, two weeks ago and felt the very same way about it. and so, yeah, it’s funny to me just to see email and email marketing and email more generally just being, you know, they, they sound we as a society or as a culture.I mean, we sounded a death notice for it just like on a regular basis. You know, it’s definitely cyclical where it’s like, Oh, email’s dead. Now that clubhouse is here, you know, email’s dead now that, you know, Facebook is like, it doesn’t matter. It’s a, there’s always something that’s going to take the place of it.And I don’t think that’s true at all. Just, you know, and I’m guessing you don’t, you don’t agree with that either. but yeah, we are in sort of this Renaissance of email and I think there’s a couple of things that are driving it. I think partly is because. Email is the place where, you know, you and I have the opportunity and everybody listening here has the opportunity to communicate directly for you as opposed to, you know, trying to game an algorithm, to try to get in touch with our audience more directly, you know, the promise of social when it first came out was, you know, Facebook was saying, Oh, this is an opportunity for you to speak to your.Speak to your customers and your prospects directly. Wouldn’t that be fabulous. And then it turns out, right. They’re going to control that ability for us to communicate directly. And so it wasn’t quite so direct. The promise was never quite fulfilled or at least it was there. And then they. They sort of yanked it away with a cane.And I think that only gave rise to the fact that, you know, email being the only place where people and not algorithms are in control. I’ve talked a lot about that in the past couple of years. and that’s very much true. And so I think that’s one of the reasons why we’re seeing, you know, email being just increasingly part of, of the vernacular or part of the mix these days.The second thing though is like the whole notion or, or the whole. I don’t the whole, the whole conversation around that when something comes up and other thing dies, it’s ridiculous to me, you know, it’s like, it’s like saying that, you know, because TV exists, radio should die. I mean, that’s just ridiculous.It just, the world doesn’t function that way. Right. It’s like, we’ve figure out a way to make it. In addition to not instead of second thing, but the third thing is I think that the rise of newsletters, just as you mentioned, like the rise of sub stack, for example, it’s, it’s directly tied to creators increasingly just owning their own platforms.And I think we’re seeing this not only in the newsletter space, but across everything. And so. You know, newsletters or maybe a place where writers, you know, journalists are, are more comfortable just like people like you and me maybe are more comfortable. They are building our own relationships with our audience, but I don’t think it’s isolated to newsletters.I think we’re seeing it across, you know, across so many, so many things, so many creators are just, you know, taking their. Taking it into their own hands. That’s why we’re seeing the rise of Patrion and some other platforms that are helping creators monetize their own audiences directly, as opposed to going through the social platforms.And I think it changes, it changes the game for creators as well. And I think that’s why, why we’re sending it. I mean, the other interesting thing, just to go back to the, the, the social thing for a second is I think that’s why we’re seeing, you know, some, I think some of the social networks are freaking out a little bit, right?I think that’s why Twitter acquired review. you know, Facebook is reporting, building their own newsletter, the newsletter platform, and then LinkedIn is offering you now the ability to, to, to build a newsletter. But it’s not really that it’s just using, it’s still using their, their platforms. And so. If anybody here and, and I know your audience is pretty sophisticated, so they probably are, are very well aware of the fact that they should stay away from those platforms.If you want to build your, your own lists, take it upon yourself. Don’t do it through one of the social platforms. Nathan: [00:27:40] Yeah, I think you’re right, because the algorithms will play into it. What you were saying about the ownership, you know, it’s something we’ve preached a lot of own, the relationship with your audience, and that being so important. But the thing that you’re seeing across the creator space is more and more creators owning that content directly.Like we. For ConvertKit, we’ve been expanding a lot to music over the last, year, 18 months or so. And we acquired a company called fan bridge and announced that last week, which is email marketing for musicians. And you’re seeing that so much in music of before, you know, people, like individual artists not owning their masters and now they’re being.Right. Like Taylor Swift, my team jokes that I’ll work, I’ll work Taylor Swift into any conversation. Ann: [00:28:28] I was literally just about to bring her up. I was thinking, this is exactly the Taylor Swift issue. Right?Nathan: [00:28:34] Yeah. And so you’re seeing these creators. Yeah. There used to be at the mercy of whether it be a record label, an algorithm, the social platforms or whatever else. And you’re saying like, look, I’m not going to play that game anymore. I’m willing to own. The relationship, the things that I create, and it’d just be fascinating to see it play out in more and more circles.Ann: [00:28:53] Yeah, for sure. Yeah, for sure. yeah, a hundred percent agree. And I, and I think that this is just such an exciting time. I think, to be a creator. To be a newsletter writer to be a musician, to be an artist of any kind, to be a filmmaker. Because I do think that we’re going to see an explosion of opportunities that we have to yes, own our own, our own work, but also own our own audiences, which is a massive, massive shift.Nathan: [00:29:16] Yeah, it’s something brand new that I’ll, I confess to not knowing super well, but that you’ve been playing in that, in that world is sort of the cryptocurrency, the creator coins, you know, there’s NFTs and. now I sound like I’m old and out of the game. Yeah. it, like, I tried to buy, you know, a, an NFT, if someone’s writing, I tried to bid on it and I couldn’t even get, I couldn’t move the cryptocurrencies around properly to even achieve it.But I’m curious for your take on the space. Cause you did write about, you know, creating the, the word, crypto or the word creator coin. And so I’m curious what you think.Ann: [00:29:59] Yeah, it kind of plays into what we’re just talking about a second ago, because I think that, you know, creator coins are cryptocurrency is, is another opportunity for creatives to get paid essentially by their, by their communities. You know, if you value somebody’s work, you can. The creator coin will allow you to support them in that way.So, yes, I launched my own creator coin a couple of weeks ago, and I’m still figuring it out, still figuring out what exactly I’m going to do with it or how I’m going to integrate it into what I do. so I launched the word going through a platform called rally.io. And what rally does is allows creators to launch their own coins.The mantra is kind of like if you have a community, you can have an economy, right? And there’s different ways that you can reward people in your economy, just, you know, through giving them. Your own coin. So for example, I could give people who, you know, like are long-term subscribers of Marketing, profs, but sorry of my own newsletter, I could reward them for being, you know, subscribers, somebody shared on Twitter that goes over the weekends, that she’s been a subscriber for like two and a half years.And it’s the longest email newsletter that she’s ever subscribed to. Or it’s the longest time she’s ever subscribed to an email newsletter and I tweeted back at her. So I’m going to give you some word going for that because you know, it’s, so it’s rewarding longevity in that case. she could then take that word going and pass it along to somebody else.There are ways that, you know, I can maybe, people can buy Cory a word coins to get access. Like VIP privileges to maybe a concept with me, a shout out in the newsletter. it could be, you know, maybe, maybe just a, like a small, a small ad in the newsletter. Like that could be any number of, of ways that I think you can use that you can use a creator coin, but, but yeah, it’s a really, it’s a fascinating.Area. And I think one that we’re going to hear a whole lot more about, especially as you know, creators are sort of owning the, all that, the Content, the audiences, and figure out ways to monetize. I think we’re going to see, you know, things like creator, coins become increasingly relevant, you know, is as this world grows and expands and matures.So I did it mostly as an experiment, but I also think that, you know, again, just to go back to, why did I start the email loser? It’s I needed to get into it to sort of understand how to use it. And so that’s essentially what I’m doing there too.Nathan: [00:32:24] It seems to me like you’re launching your own. Little economy around a coin, you know, in your community would be a fairly big investment, not maybe on the monetary side, but in the, like the time side or the longevity side of like, Hey, this is just a little experiment now, but for it to be something within our community, like we’re going to have to do it for years.Is that something that you thought about it or are you just waiting to see how it shapes up?Ann: [00:32:49] Yeah. I don’t know if they need to do it for years. but, but yeah, it does take some managing and some strategy and some thought behind it, which is why I’m hedging a little bit. When I say that I’m at the very beginning stages of it. because I just, I launched it a few weeks ago. I haven’t like, I will a hundred percent honest with you.I haven’t necessarily implemented it in any specific way, but, you know, for example, one thing that I could do is like, I could have a page on my website that said, that says like, Hey, you know, you want me to be on your podcast like this, you know, you can buy, you know, 100 word coins or something like that.And so there could be some very simple ways that I could implement a program like that. I could, I could, Offer rewards for referring the newsletter, for example, for growing the list and that way. and so I don’t necessarily think it’s, it’s very complicated or they will take a long time, but, you know, it will require me to just like, honestly, just sit down, like put my button, the chair, and like think it through a little bit more strategically than I have at this very moment in time.So that’s all coming, but it’s, you know, it’s gonna,Nathan: [00:33:52] Yep.Ann: [00:33:53] That’s on me to just kind of make it happen at this point.Nathan: [00:33:55] I have this whole list of things that are kind of like that, you know, a referral newsletter is one, and there’s just a bunch of things where it’s like, these are all ideas I add to them and. It’s not really worth spending time on it until I can spend like two hours to sit down and really dive in and be like, okay, this is actually what I want to do. Ann: [00:34:11] Yeah. It’s exactly that. Yeah. It’s exactly that. It’s the, it’s a line item that keeps moving forward every week and I keep thinking I’m going to get to it. And then I just. You know, life happens and whatever, so, but it’ll happen. I’ll get there. This is going to take me a little bit longer to actually, for anybody in the audience to sort of see anything I should say.I’m thinking a lot about it. And you know, for me, that’s always the first start anyway.Nathan: [00:34:36] Yeah, that makes sense. I want to switch gears a little bit and go to writing specifically since that’s something that you are so well known for. And like, I love the quote of, you know, from that recent reader saying, like I’m in a good mood whenever I read this, you know, and that’s, that is the best testimonial that you can get.So how do you think about. Tone and voice when you’re writing and making it something that people aren’t like, Oh yeah, there’s another, there’s another email from man. You know what I’m saying? Like, Oh, you know, I’m really excited every other week when this comes out.Ann: [00:35:08] Yeah, I know. And it actually, it didn’t like its, its kind of goofy, but it literally filled my heart. Like when she said that I was like, Aw, like I had to take a moment, you know, where I was like, that’s like, I never thought about that, but. You know, I think about the writers who I enjoy reading that’s actually is true, like what they do for me.And I don’t think it’s just because of the choice of reading material that I have, like doesn’t mean that that’s always has to be an uplift, uplifting story, but to read something and feel like God, that was like, I feel so good after reading that I was like, wow, that’s actually a nice way to think about what, one of my goals for the newsletter, which I hadn’t thought about before. so when I think about writing the email newsletter, when I sit down to write it every other week, I think about two things. First of all, I think about one person, which is a little bit of a cliche and writing, and there’s a little bit of cliche and Marketing too. But for, for me, it’s the only thing that I can do it, it helps keep my voice conversational.It helps keep my voice, loose and just, you know, it just reminds me that I’m speaking to one person at one time and it’s true, right. Because it’s one inbox. One time you’re not speaking to an entire auditorium full of readers or opening up your newsletter at the very same time when you mail it on New, my case Sunday mornings, you’re speaking to one person at one time.So, you know, I think about just that one person, and I’m usually writing to a person based on a challenge or a problem or an issue that came up over the past two weeks. It’s something very specific. So, you know, I’ll, I’ll start out in my head with, you know, like, like a dear Judith or something like that.I don’t actually say that, but I’m writing to that person and it just helps me. Get into the mindset of the person that I’m trying to help. And that person of course, is a proxy for the audience, right? It’s not the, you know, the more specific I write, the more universal it tends to appeal. And so that’s, that’s how I approach it.I sit down and I write it straight through and then I usually do three or four edits on it. And each time I edit I’m editing for something very specific the first time it’s, essentially for, you know, am I, is the content clear? Like, am I making the point that I want to make. Is, you know, when I look at it from a broader standpoint, I call it editing by chainsaw.Right? It’s all of these points make sense. Or does this point maybe belong someplace else in a different newsletter or a different piece of content somewhere? Does it belong with the rest? So that’s the first pass. Second pass is what I call it, editing by surgical tools. And I’ll go through. And think very specifically about each sentence.Does it make sense? Does it earn its keep so to speak? does it really need to be in this newsletter? I’m hyper aware of the fact that, you know, my newsletter is, is long, but you know, a lot of good newsletters are long, but when someone feels like it’s long, that’s when I, I know I failed. Right. And so that’s why I’m very particular in.In the email newsletter more so than I would be saying a book, you know, I wouldn’t necessarily go through and think about each sentence, does it? Or does it earn its keep with quite the same kind of, you know, strictness, but, but I do it in an email newsletter because I’m very aware of that and I want it to feel tight and concise and not a word is wasted.And then the fourth, so that’s the third pass and then the fourth pass is for voice. And I go through and I read it out loud at that point. And I think it sound like me. Could I add a little more humor in, could I make it sound a little bit more fun? Funny, in some cases I’ll add in some of the sides.That’s the moment where. You know if, as I say, like, if you covered up the, the, from line a Honda, you know, in your email client, you know, would it sound like me, or could it come from Nathan? Right. It doesn’t sound like it came from Nathan, Arizona that came from man. So I want to make sure that it really does sound like me.And so reading it out loud really helps with that. But then also just thinking about, you know, thinking about voice, you know, more. More specifically as, as relates to me. So that’s kind of my process that I go through. And some of that voice comes down to, as I said, humor, it comes down to word choice. A lot of times even comes down to the greeting at the very beginning.Like I start every email newsletter, usually with some kind of crazy like, Hey sassafras or, you know, hello, sweet petunia. Like some of that kind of stuff, you know, just a way to differentiate again, to sound like me and not like anybody else.Nathan: [00:39:26] I think that’s a good line. And I’ve heard, you mentioned it in a few of your talks of, if I were to take your, you know, your website, your writing, whatever it is, and cover up your logo and any identifiable brand elements that like, could we, we know that it’s you. And I think that’s something that a lot of writers struggle with of like, okay, This is useful information that I’m giving you.This is, you know, maybe it served its purpose. It’s made it through the chainsaw, edit. what are some tips that you’d have for someone who is looking to add in a lot more voice and personality? How do you coach people through that? Ann: [00:39:57] I don’t know, like sometimes I struggle with this whole conversation around voice because I feel like people think that. It’s something that they try on, you know, but it’s, it’s not something that you step into. It’s something that sort of grows on you, which is kind of a gross analogy now that I think about it and I make it sound like a hole or like, I don’t know, some kind of WARP, but you know, the, the, yeah, the notion of voice is essentially just how you sound and you know, it’s not any more complicated than that.And so when I coach people on voice, that’s why I think it’s important to read things out loud. Because very often, that’s the step that even now, I mean, I’ve been writing for, you know, since I was eight years old and I wanted to be a writer, you know? So I’ve been writing for a long time. And even now when I read things out loud, I sound like not me.And that’s the point where I’ll say God, you know, that I could do better than that. You know? So it’s just, it, I think developing a voice is less a big. Big thing that you like, it’s not, it’s like, it’s not a platform that you step onto. It’s a thousand little choices that you make all along the way that over time, grow your voice and add up to something that’s wholly unique.So find those small moments like those small moments are the things that become a big differentiation for yourself. Nathan: [00:41:19] what are, so you mentioned the greetings, what are a few of the other small, small moments in your own writing?Ann: [00:41:24] One of the things that I do a lot is a call back. So I’ll start out talking about something, you know, so again, I write it as a letter.That’s, that’s another piece of when we’re talking about how do I write the newsletter? I focus less on the news and more on the letter. So it’s a one-to-one conversation with, with a, with a reader. And so. I focus on. So I’ll tell, I’ll usually start out with like a story, just like you would, if you were writing a letter to a friend or something like that, not an email, but a letter to a friend.Right. you know, it’s like, Hey, how’s it going? What, you know, this what’s going on in my world right now. And I’ll usually tell a story about it. So it could be a story about my dog August or could be about anything. sometimes, and then I usually will do a call back later in the day. Later in the, in the sort of letter portion of it or the essay portion, I guess is another way to think about it.So callback is another one for me, a callback just referencing something that happened earlier, sometimes that it kind of tongue in cheek or funny way is another way. let me see. Thinking about vocabulary is, is important to me too. I, I sort of liked just using quirky words, I’m kind of a quirky writer.Right. And so I use quirky words to express that. So that’s why I have a department of shenanigans, for example, you know, I could, I could call it the department of the absurd, but shenanigans is a word that I love, you know, it just is like, it just like screams fun. Right. It just screams something that’s a little bit crazy.So thinking through word choice, I think is another, another, a way that I, that I layer in voice as well. Nathan: [00:42:53] Yeah, I’m realizing we have another team commented. Oh, in that, you have, we both have loved ones named August. My son is named AugustAnn: [00:43:01] Yeah, that’s right. right. I think you did you mention that to me?Cause I feel like I knew that.Nathan: [00:43:06] I don’t know. I don’t remember what we talked about that, you had one last thing that you were in his head where Joyce Ann: [00:43:12] I don’t know. I think, I think, I guess one of the bigger point that I was making is that I just, I want it to be inherently readable. Like I want it to feel like a fun ride from the beginning to the end and so even doing some things that are sort of design choices, I think feed into voice.So playing with white space, like tons of white space, tons of subheads just making it very readable, I think is just, you know, just a smart way to go. I don’t want 1400 words to feel like 1,400 words. I want it to feel like you get to the end and, and you know, and that was a good time.Nathan: [00:43:51] Yeah. You carry that all the way through which is really good. And that’s where we can segue into is where people should go to subscribe. But just in the name of your newsletter being called Total Annarchy, Annarchy with two “n’s” in this case, and that’s, that’s up there with shenanigans just as far as great words, that should be, it should be used all the time. And so people know what to expect and you’re just carrying that voice through. Where should people go to subscribe to Total Annarchy and follow you?Ann: [00:44:21] Annhanley.com/newsletter. You can subscribe right there. And, everybody who subscribes gets a free puppy.Nathan: [00:44:30] I love it. You can join the 21,000 people who love the newsletter and the 21,000 people who, who knows what they think about it.Ann: [00:44:38] That’s crazy. I have to thank you for pointing that out to me.Nathan: [00:44:41] You’re welcome. Something I can do. Well, I only bring it up because someone went through my site and we have like some numbers about ConvertKit on like my own site. And it’s one of those exact sort of things where it’s like in the about page somewhere. And it was just like wildly out of date. Like the company is twice the size that I was saying then, and someone’s like, you might want to update this.I was like, "Oh, I forgot that that’s there."Ann: [00:45:04] You know, another word that I like is nincompoop. And I would use that for myself at this point. Cause I really should have changed that.So, Oh, well.Nathan: [00:45:12] Well, now you can. Well, Ann thanks for coming on. This has been really fun.Ann: [00:45:15] Yeah. It was a lot of fun. Thank you so much for having me. And yeah, it’s been a pleasure.

Dickie Bush is a full time Portfolio Manager based in New York City. He is a graduate of Princeton, where he received a degree in Financial Engineering and played on the football team.Dickie writes a weekly newsletter called Dickie’s Digest where he shares thoughts and links on growth of all kinds, including personal, intellectual, physical, network, economic, and other forms of growth.Dickie is probably best known as the founder of Ship 30 for 30, an online cohort based course where he teaches writers how to write better, grow their audience, and show up consistently.In this episode, you’ll learn: How Dickie runs Ship 30 for 30 How to build an online writing habit How to shorten your feedback loops to improve your writing Tactical tips to build a following on Twitter Links & Resources James Clear The Art and Business of Online Writing by Nicolas Cole 30 Days to Better Writing by Sean McCabe ConvertKit Jack Butcher Tim Ferriss The Nathan Barry Show 031: Mario Gabriele – From Lifelong Obsession to Thriving Business David Perell Andrew Wilkinson Sahil Bloom Julian Shapiro Dickie Bush’s Links Ship 30 for 30 Substack: dickiebush.substack.com Twitter: @dickiebush Episode TranscriptDickie: [00:00:00] One that accelerated my growth, every morning, Monday through Friday at 9:00 AM, you’ll get a question to reflect on where a lot of the replies become interesting pieces of advice. Right? I’m playing with one right now that I said, “Give the best advice you can in just two words.” It had 3,000 replies.The Twitter algorithm. When people respond to something, it shows up in more feeds.Nathan: [00:00:27] In this episode, I talked to Dickie Bush, who works in the finance industry, but has this wildly successful side hustle teaching writers how to write better, grow their audience and show up consistently, called Ship 30 for 30. This episode we get into a ton of great stuff, how to grow your Twitter list, how to stay accountable.We deep dive more than any other episode on the Twitter algorithm, what works, what doesn’t, some of it is pure speculation. Some of it are things that have been pretty verifiable. There’s a lot of good stuff. I think you’re going to enjoy it. I particularly love how Dickie has put together these flywheels that he’s refining each time he does a new cohort of the course. There’s a ton of momentum here. He’s just absolutely going to blow up. And it’s really, really impressive. So with that, let’s dive in. Dickie, welcome to the show.Dickie: [00:01:15] I appreciate you having me. Look forward to it. Nathan: [00:01:17] All of our listeners are very active on Twitter. And you can’t be active on Twitter in the circles that you and I run in and not see your Twitter growth. I see Ship 30 for 30 growing, like crazy everyone, you know, posting essays and all of that. Before we dive into all of that, there’s something that I actually didn’t realize until prepping for this episode yesterday.And that’s that everything we see online is just a side hustle for you. Can you talk about, at a high level, what you do day to day, and then, how you balance that with your wildly successful side hustle. Dickie: [00:01:58] Sure. So what I do, full-time, I’m a macro portfolio manager and the way I kind of describe it as my day job is to predict the global economy and how that unfolds. And there’s only so many charts and numbers you can look at on kind of a daily basis from seven or 8:00 AM to five or six. And so my writing online and kind of journey, and that has been just a, a way to kind of step back from kind of the madness of, of markets and economies and things like that.And explore just little interests to me. And that has evolved relatively quickly, over the last, you know, nine months.Nathan: [00:02:38] Oh, I’m glad you said the nine months time. I, cause that that’s roughly what I’ve noticed as well. What was that inflection point where you decided you’re going to really focus on building an online audience and, you know, start writing online?Dickie: [00:02:54] I guess a little bit of a backstory it’s probably longer than nine months. So I started writing online in January of 2020. With just a weekly newsletter. So I came into 2020 saying, I’m consuming all these podcasts and books and articles and just interested in learning. But my notes would end up in the back of a Notion notebook kind of into the void where, you know, there was no upside.And so I started kind of exploring, how can I start to have a forcing function to learn more about the things I’m doing? So I just started writing a weekly newsletter. I had seen people do it and you just curation and et cetera. So that was kind of my foray into it. And I did that for about 35, 40 weeks, and started writing on a blog, exploring dabbling in some things that I was interested in, but in July, I’d probably published 30 or 40 newsletters in a row, a couple of blog posts, but just felt like I was kind of stuck and had so many ideas that I wanted to explore, but didn’t have the medium to do it. When my feedback loop was slow, I was on the weekly cadence, but it was inconsistent, et cetera. And so coming into August, I started just tweeting more and getting through these ideas. And I’m sure we’ll talk more about Twitter. It’s kind of an idea refinery, right? You can just get these ideas clear the junk that’s in your head to find out what you really want to talk about.And so that was, you know, that was kind of the inflection point was when I made a new Twitter account in August and said, “I’m going to start to share these ideas that I think I want to talk about.”"Nathan: [00:04:27] As much as I want to ask there, but you said you made a new Twitter account. You just started more from scratch and kept, you know, forked off of an old one. What did you do there?Dickie: [00:04:34] So that one, I had a Twitter I’ve had Twitter since 2014, 2015, you know, big lifetime, just been involved with the product and loved it. And. There was a little bit of, okay, I’m going to pivot this. I had four or 500 followers at the time, had done some kind of thread curation and things like that. But my follower graph, I think was a little bit not damaged, but Twitter’s algorithm.If you went on my account and said, who are this person similar to? It was all inactive accounts from high school. And so I just wanted a fresh slate too, kind of start over. And so I made the new account and said, Hey, I’m making a new account when I kind of reset this thing. And so I didn’t also have like tweets from high school and things like that in there.so I just started fresh and it felt like a good way to do it.Nathan: [00:05:19] So you made a new account. Did you slide over like, you know, swap the same username or is it a different username?Dickie: [00:05:26] I swapped the username. So cause that one, it’s just thinking like, I didn’t want to lose it. So yeah. I changed the username on the old one, made the new one and then change back. So.Nathan: [00:05:34] Yeah. And you have that, that brief 45 second window where you’reDickie: [00:05:38] Yeah. And like sprinting, I’m like, Oh, there’s hundreds of people who are about to steal it. Yeah. They’re just counting down.Nathan: [00:05:42] So that’s the first time I’ve heard the, like the Twitter algorithm or this idea of a damaged account.Can you talk about that more?Dickie: [00:05:51] It’s a total hunch. Right. But now if you go on my account and it might’ve just been, I didn’t have kind of that breakthrough or followers, but it was. You know, now when you go on my account that people, similar to, or other people in kind of our Twitter sphere. Right. Whereas in the old one, I was engaging in that community, but it was just inactive.So I, you know, I have no proof to back it up, but I was able to kind of grow what, sell more quickly right after.Nathan: [00:06:22] Yeah, that’s interesting. And I wonder how that plays into it. But I could totally see that of Twitter being like, I don’t know, the guy’s just tweeted about random stuff for five or six years. Like, what do you want me to recommend them for? And then you’re like, no, no, no, this stuff. And you’re like, okay.But that’s like 2% of what you’ve ever tweeted. Yeah. Got it. So, Dickie: [00:06:42] Yeah, there’s something there, but I don’t know.Nathan: [00:06:44] I’d love for someone to run some experiments on that and see if, how much that matters. But, one takeaway from it that I appreciate is you didn’t just say like, Oh, here’s a new thing that I’m doing.Let me lean that direction. You said, no, no, no. This is something that I’m taking seriously. We’re going to go all in on. And really you didn’t, you weren’t attached to the sunk costs. You know, or like I, but I I’ve already 500 subscribers, then I’m going to throw that away. It was just the approach of like 500 is not going to take that long to getDickie: [00:07:16] It was almost like an acceptance of an inconvenient truth because I did have that sunk cost for like two months of like, Oh, I have 500 followers. And when I made the new one and said, Oh, I’m making this new one, like 45 came over. Right. So, so many of those were inactive accounts as well.So it was kind of this mental thing of like, Oh no, I can’t give this up. But it was clear that I really hadn’t done as much as I thought.Nathan: [00:07:38] So that’s interesting. Cause that’s the, you know, the person With an email list that they’re proud of, but with a terrible open rate and they’re still like, I have 10,000 people on my list and you’re like, yeah, but you have a 5% open rate, but you don’t have 10,000 people. And they’re like, no, I have 10,000, you know?And it’s just like, you got to accept the reality and realize that. Now you’ve got 500 people that actually are paying attention to you.Dickie: [00:08:00] Yeah, there’s, there’s tons of, like. Goodhart’s law or just whatever, whatever it is, where you have this indicator of like, Oh, I have 10,000 email X, but now you’re, you’re spot on.Nathan: [00:08:10] Yeah. So how many subscribers did you have, like last July when you sort of started to take Twitter and writing more seriously or just before that?Dickie: [00:08:17] On my newsletter, I had about 200 and that was over 40 or 35 weeks. And, you know, I probably signed up about half of them. And I, I hadn’t done much on the growth side. I just was kind of writing it and saying, now this is fun. It’s a forcing function. What have you? And, I started that Twitter account really with about a hundred.So relatively small, to start.Nathan: [00:08:43] You know, at that point it sounds like you, you transformed it from like journaling. Here’s what I learned all of that to actually focused on, on growth. Is that right?Dickie: [00:08:54] Right. It was, I started to just, I, I took a look at all these things, what I, to basically done in the nine months leading up to that was built up this idea of a blog post in my head where it’s like, Oh, I have to sit down and write this thing and edit it and get feedback on it. And so it just had this super slow feedback loop.And I had this massive list of ideas, like, Oh, all these different areas I wanted to explore, but no medium to do it. And so what Twitter became was just, I could share these one-off ideas, Write, feel like, do a little bit of writing, make these small bets on if things resonated. And then at the same time to kind of have just more eyeballs on there.So I wasn’t publishing into the void. I took what I was doing on my newsletter. you know, Podcast curation and started just summarizing the ones I was listening to. Right. And people appreciated that it made them more digestible. So it was kind of this, this, value add while I was exploring these more ideas.Nathan: [00:09:51] Yeah. And that’s interesting. I think, I probably do the same thing of like building up, like my favorite blog posts that I read are from where you can tell someone to put a huge amount of time and effort into it. And it’s polished detailed Research. Do you know whether it’s a piece from like someone like James clear or, you know, I love these like complete guide type posts.And so I find myself waiting, you know, And I might publish four of these a year or something myself, but. Exactly. As you’re saying, there’s a lot more ideas out there. And a lot of unrefined ideas that if you’re not careful, like that’s the unrefined ideas, what’s going to make it into your, like your long form detailed blog post.Dickie: [00:10:34] Well, I think it’s important. That’s an important point because now you can publish for a year because you have a credibility to it. Where in the beginning you could publish the ultimate guide, but there’s not really anyone who sees you as an authority in that area. Right? So in something we preach and Ship 30 is you have to just get these ideas out there and work through a lot of it.Where people are going to come to your blog later, once you’ve kind of built a small following versus people just finding their way onto your blog, right? So its kind of a chicken or egg problem. And that’s why I think the beauty of Twitter is you can start to accelerate these feedback loops, versus just kind of publishing into the void.Nathan: [00:11:16] Yeah. Yeah, that makes sense. So something that you’re doing A lot, and I’m curious when this started is playing around with different formats for tweets. You know, and, and really with Ship 30, I’ve seen you popularize that a lot of having a headline, you know, you’re leading in the tweet itself and then the essay, as an image, when did you start to notice that working and was that inspired by anybody?Dickie: [00:11:39] So I’ve seen it all over Twitter early on. not early on, but a couple months ago where I think the very first one was, I can’t remember his name, but he, he was doing like venture capital, blogs, like blogs in a single screenshot. And I loved the media. Right. It’s like Twitter is a horrible place for long form content.Well or medium form content. I should say, Write threads are kind of they’re just a little bit clunky, right? There’s a time and place for threads on like, Poignant advice and things like that, but there is a, sometimes you want to read something like that. And so the atomic essay is just a way to tweet something, expand on it all in the same medium.Right? So it’s like you said, with the lead in, you put something out there. If people want to read more, it, they can click on the image, read it, but it’s also kind of a standalone, whatever it is at the top. Right? So it’s like this optionality that you create. That leads and it’s kind of a, it’s a scroll stopper, right?People stop on images versus a, just a sea of text. And it’s easy to kind of scroll through.Nathan: [00:12:45] Yeah. And what’s interesting about it is also the load time. I have spent a lot of time in user experience. You know, I got started in designing mobile apps and, and just people have really interesting. behaviors when they’re on their phone, especially, if the, the internet connection might not be the best and all of that.And you just see so many people click through to a site, let’s say it’s currently popular on hacker news that day, and it’s overwhelmed. And the server’s loading slowly. And they’ll just click right back out and move on because it didn’t load fast enough. And there’s also just this unknown of sure. I clicked through this link, but what am I actually getting?And Twitter tries with the Twitter card, sort of give you a little preview maybe. but the expectations and the load time are Things that I don’t think you should underestimate with. You know, what you’re calling in a telematic essay of just clicking right in. And I know. You got to fit the whole thing in that screenshot.And so, you know, it’s going to load super fast and I only have to commit to reading it for, I don’t know, the next 45 six.Dickie: [00:13:51] And it’s, it’s something we talk about. And it’s a quote from Julian Shapiro. That’s where I, first of all, it is people don’t have short attention spans. They have short consideration span. And so it’s a, it’s an empathetic writing medium, right? It’s like, you’re not going to have to read very much. We try to say that you better grab attention even in your atomic essay in the first line, because people can just swipe it away.Right. So it’s like a, it’s a way, it’s a way of thinking of, we’re not asking you to do very much by reading. This is clearly not going to take you all day. you can swipe away if you want. And yeah, the load time is interesting too, cause it’s always right.Nathan: [00:14:25] You named it and atomic essay, is what impact do you think that has had on, on, you know, giving it a specific brandable name?Dickie: [00:14:35] It made sense to me as I see these as the building blocks for a lot of longer form content. And these, like you said, these, these blockbuster blog posts are really 15 or 20 writing sessions boiled down and kind of put all together where you could take one of the sections and it could be a standalone blog for a lot of them.So we see it as like this building block, atomic chemistry. What have you, physics, a lot of these longer form ideas. And so it just brings down the friction. It’s I’m not publishing anything long It’s I got to take one idea. I got about 200 words of space and I’m going to do it every day for 30 days.So all of these things kind of make it of lowering the, shaky hand to hit publish. Take all that friction away and make it as small as possible.Nathan: [00:15:29] Yeah. I love it. You know, so many people obsess over word, count, obsess over. I was going to say substance, I think, I mean more like making it really impactful. And so, you know, if you’re publishing on a weekly or a monthly cadence, then you’re putting so much more pressure on yourself. And so, or they’re doing other things where they’re saying I’m going to write every single day and it never leaves their computer.I’m curious as you made this pivot, Ooh, you know, last, last July last August, what did you notice different in your own writing habits and maybe what were some of those examples of ideas that got refined? You know, when they actually, I guess, hit the market rather than just being inside your newsletter.Dickie: [00:16:13] I think first and foremost, I learned to write quickly the part of the constraint is we say under 250 words, try to do it under 45 minutes and just get in the habit of being okay with B plus quality, with a plus consistency in the beginning. Right. Earn the right to focus on quality by getting through and building this consistency.And then. So that was kind of, for me, my ability to sync has gone through the roof to where it’s like, I have this every single morning, this Coliseum to do, thinking on a single idea where anything I’m kind of want to explore further, I get 45 minutes to an hour to try to refine it. And the. The constraints of it, of getting it down to 250 words really improves my ability to kind of work through it in a, in a simple way.So it’s all of these things that just bring my thoughts a little bit more coherent.Nathan: [00:17:15] Yeah. That makes sense. and then are you still bringing it to long form essays or you found that you’re really focused on, on the shorter, medium?Dickie: [00:17:24] So I haven’t, I’m disappointed in how much long form writing I’ve done, just because building the business side has kind of taken a lot of the long form content. So I’m still publishing along. I’m about to hit my 100 and at that point, I’m going to start to flip back through them because I’ve a lot of the things.Like my threads have been, you know, expanded upon atomic essays and things like that. So I had this foundation that I’m looking to put on a blog or on a whatever from here, but I just haven’t found the time. So I got this big backlog and eventually I hope to kind of pivot into, into the longer form.Nathan: [00:18:01] Yeah, well, it’s interesting. I’m, I’m thinking about the number of ideas that I’ve been putting down and writing into a book and found that because that format requires so much thought and structured and they all almost should be accompanied by. This other side of the really casual, like it here for a high friction of we’re going to put it into a traditionally published book.These are well-refined ideas. Then we should have the opposite of anything here is where there’s complete freedom. You have to publish. I love the time constraint of like, try to do an under 45 minutes, and just iterate quickly and refine those ideas.Dickie: [00:18:42] So we think the constraints are the biggest part of it, right? Any I’m writing a down on this now it’s like there’s seven or eight different constraints you can have as a writer and decisions. You can make, you know, medium platform, topic, length, time to Write publishing and. Every ounce of thought you put into those decisions takes away from your rights.So everyone that comes into Ship 30 it’s like here are the eight things you might have to decide, and we’ve already made them for you. Now go Write everyday for 30 days, we give you the templates. We give you all of the things you need. It’s like, okay, just explore 30 ideas now. And we, the creative freedom that we see it unlock is, is tremendous.Nathan: [00:19:25] Yeah. Okay. So let’s talk about, for a second about the format of Ship 30 and. So you it’s a, a course, you know, cohort based course that you’re running monthly. How many months have you been running it now?Dickie: [00:19:38] So it’s every six weeks just to give a two week break in between kind of reset. so the very first one was in November and we’re on cohort number four Day 16 and today’s April 14th. So yeah, we’re on the fourth cohort right now.Nathan: [00:19:52] I had, like in first reading, I had seen it as monthly and I was like, that must be crazy to go 30 days, like, and justDickie: [00:20:01] Yeah, we found it, with, with off-boarding and trying to make improvements like the two week between each one has just been a heads down sprint of how can we make this better? What can we learn from our off-boarding and how can we Ship as many new features? and so that’s always a fun time, but yeah, it’s about every six weeks.Nathan: [00:20:17] So is it a ramp up? And then like when I sign up as a student, isDickie: [00:20:23] SureNathan: [00:20:24] up over our first week? Or take me through that experience?Dickie: [00:20:26] You will sign up. We drip you through like a resources sequence until the start of onboarding week. So onboarding week will start one week before the first day of the 30 days. So on that Monday, You’re brought into the community Slack. We take you through a pretty comprehensive onboarding where, which is when you take the, how to Ship 30 for 30 course, which is, are just, it’s a, it’s a writing course, but it’s really a habit design course.We give you everything you need to set up your daily writing workflow, all the templates and everything, and then work you through some more resources. Get you introduced to the community, sets you up in your accountability partners, et cetera. And then on Monday, you’re ready to hit the road.Nathan: [00:21:05] Yeah. So, and then before that you’re talking about dripping it. So if I were to sign up say, let’s say I were to just miss, you know, sign up for one cohort and I’m like, Oh, the next one sounds interesting. I could buy that. Today. And then I would receive that Content timed out, you know, over a couple of weeks.Dickie: [00:21:25] So you wouldn’t have access to the actual how to Ship 30 course. We put that just as the week on this, these are more just how to improve your writing Podcast articles, you know, things like that. And then on the first day you are entered into a 30 day email course written by Nicholas Cole. Who’s just one of the most he’s my business partner.And. The master of online writing in my opinion. And he put that together every single day, you get a prompt if you’re running out of ideas and then kind of an actionable piece of writing advice on crafting headlines, gathering attention, distribution, those kinds of things.Nathan: [00:21:59] Nice. Yeah, that’s great. Something else I noticed that you do, in your pricing is that the pricing changes as it gets closer to the date. Can you talk about that?Dickie: [00:22:09] Yeah. The, we like to have a good sense of how many we are going to have. and there’s also a bit of the most public momentum on it happens at the beginning of each cohort. Right? So on day one through five, we’ve been on kind of a two week, two week break. And so during that first week and a half people that are unfamiliar are going to be greeted with a bunch of new essays.And so we try to capture that momentum in saying, Hey, if you want to sign up now, like you’re going to regret it later if you don’t pull the trigger earlier. And so it’s just a, it’s a way to incentivize early sign-ups and that gives us more clarity on the size of each one.Nathan: [00:22:50] Right. So it’s something I. I’m realizing I’m relying on a screenshot from my notes, but the pricing being like one 99 until April 5th and then two 49 until April 26th and then two 99 from April 20, 2016, up until close. So, you know, it’s basically saving 30% if you sign up today rather than say, Oh, that’s so cool.I’ll totally do it. And then in 20 days from now, when it’s actually time to sign up being like, Oh yeah, I’ve, you know, I’ve got busy or whatever else.Dickie: [00:23:21] Right. It’s all about taking action. And so that’s what we try to incentivize.Nathan: [00:23:25] Yeah. So how do you think, the balance in, right in the product that you’re selling of in Ship 30 for 30 it’s obviously courses, Content, accountability, and all that. How do you think about the balance between a course like in the, the content and the structure that you’re selling versus the accountability of like, look you have.You have all the ingredients, you, you just need someone to say like, like hold you accountable to Shipping and, sitting down and doing the writing.Dickie: [00:23:55] Yeah, it’s a, we try to front-load the. Here’s everything you need. And then the 30 days give as much accountability as we can. So we have office hours sessions. We have a, popping into Slack. We have accountability partners. It’s we try to say, okay, if you have all these things in place to sit down on the first day of the 30 days and start writing, no matter what Day 11 is going to be hard.And so how can we intervene in that and continue to give you new ideas, engage with friends, bounce things around, you know, that is so it’s like a Content Content Content course to begin. And then all about accountability.Nathan: [00:24:37] When you’re running the same cohorts, you definitely see those trends of like, alright. Day 11 is hard. I can totally imagine that. The number of times that I’ve had a daily writing habit. Start or any kind of daily habit practicing the piano, you know, running or whatever else.And you hit basically that like day seven, you’re like, yes, I’ve got a streak and then Day 10, 11, 15, somewhere in there. You’re like, damn it, this is hard. This is a lotDickie: [00:25:03] Exactly. And we track a lot of that data where we’re attracting the analytics to our web app, where you publish the essay and we’re able to see, as people started to fall off, what can we do? And we’ve learned from the first three lines. If you can get to Day six or seven with some momentum, you’ve got a good chance.And then you’re going to face another struggle around day 15, we call it the debt. Just, you know, Seth Godin’s the debt. It, it happens to everyone. And so we really intervene during that time. You get them over that hump and then they’re getting to day 30. So we’ve found kind of these places to intervene, to maximize the number of people that get all the way through.Nathan: [00:25:38] Yeah, that’s interesting. So you’re talking about this web app. So people aren’t just posting their essays on Twitter, or maybe to their existing email list there they’re actually publishing them inside the application as well.Dickie: [00:25:48] No. So the application is just kind of a text box that allows, so we started with just a Figma template. And distributed to everyone, but you can imagine the user experience is not that easy to maneuver a Figma template. So shout out to the first two cohorts, who’ve kind of put up with that. And then we had a community member build this web app where you get full creative control, but with a much easier interface.And then you export it right to an image you tweet right from there, but there’s no platform kind of for the images themselves yet, or thinking about something with it. But for now it’s just, just a standalone.Nathan: [00:26:25] Yeah. So how do you think about the, like the viral loops on this? I guess there’s two sides of it. One is for the individual creator, you know, of the audience of their building and all of that, but I’m, I’m work here is about for the product that you’re selling. Right. Of, The shift 30, it needs, you know, new, new creators to come in and participate in all of that.And you haven’t really conveniently that all of your students, you know, all of your successful students are doing your marketing for you. How intentional was that? And then what changes or what tweaks have you made along the way?Dickie: [00:27:04] That was not as intentional as I would like to say that I had this thing, you know, big vision, but when it hit me that the more successful you are. The more marketing you do for the program, every successful one becomes kind of the front end asset for it. It was, I knew we were onto something when that clicked.So I threw in, there was a little things like in the Figma template, if you want, you can put it your own URL, but if not, it just says Ship 30 to thirty.com. You know, we have the hashtag, we have people it’s a very ubiquitous thing, right. So there’s a lot of parts to, The branding of it, wherever it’s very recognizable and it’s working, right.The audience that each member builds wants to then do it. So its kind of a, it’s a beautiful loop.Nathan: [00:27:52] Yeah. Are there other, products or courses or things like that that you’ve seen with a similarly successful, viral loop?Dickie: [00:28:00] I’m not sure to be honest. I think it’s. Because of the nature of it being like a writing challenge, in a sense you there’s a lot of other courses, you learn something and then apply it to something completely different. But this is a very specific thing of what your goal is, is to write. And so by nature of writing, you build in that, that viral loop.Nathan: [00:28:24] Yeah. And it’s just, it’s taking everything that would be spread out over a long period of time. Like someone might be thinking about, okay, I’m going to do a cohort based course. I’m going to, I’m going to charge a thousand or 2000 or $3,000 for it. It’s this big thing. It’s, it’s going to be six weeks or three months, like a semester long, you know, or.All of this stuff. And then they’re going to implement what they learn over the next three, six, 12, 24 months. And that like, that’s interesting, but what you’ve done is you’ve just taken all of this and crammed it down into one thing with very clear deliverables. And so all of that momentum happens all at once and it’s fascinating to me.Dickie: [00:29:07] Yeah, and I think that’s why we’ve been able to grow relatively quickly. We started with 55 and the first cohort were 171. Then two 50 and now the current one is 335.Nathan: [00:29:18] Wow. Hmm. Okay. So, so those are some of the numbers get into the revenue side, right. how much have, have you earned from the business and, and what are you looking for going forward?Dickie: [00:29:30] So total we’ve, we’ve done some things with the pricing where in the beginning, In the January cohort, the price was $99 because we didn’t have the how to Ship 30 course. We didn’t have the email course. We didn’t have a lot of the things that we put in place now where we feel much stronger about charging.So now Write the price. As of right now is 250. And so our average price for every single person who has come through is about 135, but that’s increasing now. And so the revenue breakdown. From just shift 30 is right around a hundred, a hundred thousand. And we have now Nicholas Cole and I have launched a follow on writing course called the right to Ship, which is for everyone who takes Ship 30 for 30, and really wants to double down in kind of an immersive online writing masterclass.It’s the only way to describe a Nicholas Cole’s book, the art and business of online writing, which of course is based on his kind of head blowing emoji. Where he’s just been in this game for so long. and so he, he’s a primary teacher for that, and that has done about 45,000 between, so those are when the first quarter, and based on just our, our current trajectory where we’re looking to, I don’t have an exact projection, but we just start, it’s hard to forecast.Right. We’re just moving quickly and continuing to improve all the products. And, and on that side, we’ll see what happens.Nathan: [00:31:00] Yeah. Yeah, that’s good. One thing. Right? So those are all the really positive, exciting, sides of it. one thing that I want to ask about it, especially because it involves, you know, our community directly, is some of the, like when you first came out with the sales page and everything for, shift 30 for 30, like the cost and similarities to Sean McCabe’s, 30 days to better writing.And so I’m curious. One how that came to be. And then also, you know, how you handled a mistake like that. And then maybe the final thing is, is sort of this, this balance between, inspiration and us all being in the same community and learning from each other versus, you know, something like plagiarism, which is a big deal in the, in the writing community.Dickie: [00:31:48] Yeah, that that was a, drastic mistake on my side and caught up in. The idea I had was just market research on some are things. And I, to be honest was, it was just a terrifying moment for me when I realized what I’d done caught up in kind of a, a swipe file of notes and different things like that. And right when I kind of clicked two and three, it was, I need to own this mistake spot on.And so I said, Sean, this was a massive mistake. I, I. Take full ownerShip of it. I apologize. And I took it. I mean, it would have been up there for no more than a minute or two, no lie. And I took a step back after that and said, I have some, this has grown faster than I thought and had some work to do. And so I tried to, you know, took a step back and said, how can I prevent anything like this?I need to check myself and. That was a big moment of growth for me, where I kind of got shaken awake and I’m glad Sean was tremendously respectful and had every reason to be, you know, not as, as nice as he was about it until I’m very glad that we were able to, to kind of work that out.Nathan: [00:33:06] Yes, I’m in, Sean’s an incredible human I’ve known him for a long time. He actually lives here in Boise. He was over at my house like four days ago for dinner. and, and so I, he’s just so generous with his time and everything. And I think on the business side, there’s a lot of places that you can make missteps.I’ve certainly had them with ConvertKit over the years with my own writing. And so, you know, one, I think it’s important to talk about them, too, like exactly like you did, I’ve just own up to it. There’s this other angle that people can take of like, Oh no, I didn’t like let’s pretend that happen or something.And that is a sure way to take, you know, a small problem and turn it into a huge problem. cause the internet is very unforgiving of people who. Pretend that they didn’t make a mistake, you know? and so just like owning up to it directly and then sharing lessons learned from it. So, I love to hear that, you know, that was a point where you’re, you’re putting in more, safeguards or things like that.Is there anything that you recommend for writers going through your course or how they should, you know, make sure to cite sources properly or, You know, bridge this gap between inspiration and, and, like w wild side of inspiration and what they’re actually publishing.Dickie: [00:34:31] I think it’s a, you hear it to imitate then innovate where the more you can, all of these ideas are remixes and you want the best way to do it is say where your you are inspired from. And so it it’s credit in the footnotes or whatever it is, but the more you can take ideas and then expand upon them, remix them, bring them together with others, is something we preach heavily.Nathan: [00:34:55] Yeah. Yeah, that’s a good one. It makes me think of there’s this idea of, you know, leverage selling products, multiple times, all of this that I’ve talked about for a long time, you know, I wrote a book about it and back in 2013, All this stuff. And then I came across Jack butcher, you know, in the last couple of years, phrasing it as build once, sell twice.And that was just the, you know, the, all these concepts that he had just narrowed down into one really simple phrase. And it’s like, Oh man, one, I wish I thought about that. I thought of that because it’s such a good phrase. and then, you know, too, I want to use it in my work. And so it’s just like, okay, I.As a writer. I absolutely can. I just have to immediately say like, well, I learned from Jack butcher. You just have to give that, that credit immediately. cause there again, there’s nothing new under the sun. It’s all been said one way or another and it’s just cite your sources.Dickie: [00:35:54] Yeah, spot on. It’s fine.Nathan: [00:35:56] Let’s dive into the Twitter growth side. Cause that that Twitter account that you spun up, you know, starting from scratch, is now over 20,000 subscribers. So things have, have taken off. what have you learned in going from zero to 20,000 and what are we at eight months now?Dickie: [00:36:16] Yeah, I think it’s a, it’s definitely a consistency side where I think I’ve tweeted. 35 times a week for the last call. It, however long since August, have written three or four threads a week and Twitter, it’s a fickle platform because you have to consistently create content and continue to put it out.There is a way you can kind of put some Metta threads together and have, you know, ways of, of linking your old content. But at the same time, if someone visits your site or your profile, They get about four tweets or your bio to decide to follow you. So it’s a consistent kind of putting things out and also just having a clear value proposition either whether it’s in your bio or things like that, where the amount of optionality that anyone has to follow other people on Twitter, you kind of have to have a decent calling point.So all those points you can put in place to make that easy is the name of the game.Nathan: [00:37:17] So were there, like in all the different types of. Tweets. And I’m wondering if you even break this down. All right. There are things where you’re or if I look at what’s working for me, sometimes I’m surprised by it. Like I asked a question of, Hey, what is genuinely asking? what has made for a great Airbnb that you’ve stayed in because I own a few Airbnbs, I’m looking to level up the experience, et cetera.And that was like 350 replies and all this engagement and all of these followers. and I was like, I was just, you know, taking advantage of the fact that I have bunch of trends. That’s what our followers to get an answer to a question rather than, you know, looking for engagement. So I’m curious in all the different types of tweets that you could do, whether it’s threads questions, pithy, little perfect, you know, quotes like things that people will always agree with.What stood out to you that has worked in those, or are you just always playing with every different style?Dickie: [00:38:16] I have a couple consistent ones that I do. So in February, I for I’ve been journaling every morning for two or three years now and have kind of a staple of questions. And so this was one of my old blog posts that I published kind of into the void of my 10 favorite journal questions, 10 favorite questions to reflect on and where I found them.And I wrote up a thread on, on those, inspired by Tim Ferris. And in February he shared a link to my thread in his five bullet Friday. As a and so that was, for me, it was, I mean, I’ve listened to every episode. It was one of the coolest things to, you know, be just scrolling through and boom, get your name hit in the middle of it.So one that accelerated kind of my growth, but at the same time I’d been tweeting some reflection questions. And so now every morning, Monday through Friday at 9:00 AM, you’ll get a question to reflect on. And it’s just an interesting question for me. And so I find that these consistent formats where. You kind of become a Chipola like consistency, where people come to your profile and they know what to expect on a lot of things.Like I ask a question of the day on Mondays and Wednesdays of just, you know, what is financial freedom look like to you? Where a lot of the replies become interesting pieces of advice, right? I’m playing with one right now that I said, give the best advice you can in just two words. And it had 3000 replies.Had just because it was, and it was just a classic example of these constraints, creating creativity. but now those, the ones that are just engaging, asking questions, obviously scale is you have an audience, but they’re the most fun task. And as a nature of the Twitter algorithm, when people respond to something, it shows up in more feeds, right?So there’s that kind of, like you said, about the Airbnb, it was the reason so many people saw it was everyone else saw other people respond to it.Nathan: [00:40:10] As you look at that algorithm, are you seeing other things that are, you know, rewarded more? since Twitter does reward, you know, at first it was just retweets. You know, if you want to be seen in other feeds, it had to be retweeted and now favorites and replies are, are playing into it as well.Dickie: [00:40:27] Yeah, I think less so on that. What works? It’s the, what does it work or posting the links. And so if you try to take Twitter off, if. You can see it in the data of, if you try to post links to something, you’re it just gets crushed. I don’t, I understand why I don’t know how they kind of program it, but I’m sure it’s some algorithm to do so, but that is a reason to any kind of writing you do.And you’re seeing it more is you have to repurpose everything for Twitter. And that’s what their goal is, is like they are taking flight in this creator ecosystem, right. They want you to stay on the platform, create content there. And so if you have a blog post and you’re not, you know, I think Mario who was on the last episode does a tremendous job breaking down every post of the generalist into a thread.And that gets a lot of engagement naturally, because if he just said, Hey, here’s the breakdown, go click on it. One people don’t like to leave Twitter very much. And two the algorithm doesn’t like when you try to bring them off. Right? So it’s a double whammy that, if you’re repurposing, you’re going to get the best of everything.Nathan: [00:41:31] Yeah. And I mean, that’s something that we’ve seen with, YouTube quite a bit where YouTube does not like to drive traffic off of the algorithm or off of the platform and the algorithm, you know, you could say. It’s debatable, whether it penalizes videos that drive versus it rewards, videos that keep people on the platform.Probably some combination of both, when we have these, this Content that, you know, so I wrote an article, probably the last, like really serious, essay I wrote was called the billion dollar creator. And I wrote that on my blog. It’s, you know, I don’t know, 3000, 4,000 words long or something. and. That Twitter thread that I wrote of taking the highlights all the way down, you know, turning it into a threat and making sure there’s images for each thing.That’s probably the most popular tweet I’ve ever put out. but I’m curious when you’re thinking about taking long form writing and repurposing it for Twitter. When do you go to a thread? When do you go to, you know, an atomic essay or something put into, you know, a screenshot and. Is there a system there?Dickie: [00:42:43] There’s not that clean of a system, but my kind of mental hierarchy is everything starts as a tweet. And if it’s got a little bit engagement, I’ll explore it more for myself and posted it as an atomic essay. And then if that gets a lot of engagement, I know there’s people are more likely to share threads.I think just because the, you know, I think it’s a little more natural of like a retweet versus retweeting, the image. so that’s kinda my. Sot. And I think on the long form side, it’s definitely a thread because it ties nicely in to most of your long form content. It’s going to be a lot of not standalone things, but sectioned off things.Right. So you can repost each one is its own kind of standalone, all the way down.Nathan: [00:43:28] Yeah. That’s interesting. Somebody else I see is like, David Perell will often do this as he’ll go back to these old threads. or AIJ who created card? he’ll do, he has this thread, that’s probably like 500 tweets long at this point of like every update and improvement he’s ever made to card. How do you think of that as opposed to new ContentDickie: [00:43:48] Yeah, that, one’s a little bit of inside baseball, where if you, if you have a tweet thread and you respond to it later, it shows the top tweet and the most two recent replies. So I just wrote a thread in my most popular one, ever. And it was just 10 inside Twitter, like advanced Twitter tips. And that one blew up beyond my wildest dreams had 40,000 likes or something like that.And one of the tips was if you want to re, re bring Content back up to the top, just respond to it. And don’t retweet it, like add a new layer of thinking to it or something like that. And it naturally just brings it back up to the top as if you just tweeted it.Nathan: [00:44:31] And so then people are seeing this, this tweet that’s already, popular. It’s already maybe got 300 likes and twenty-five retweets and they’re like, Oh, this must be good. And they’re not paying attention to the fact that it’s, you know, six months old or six weeks old,Dickie: [00:44:48] Correct. Yeah, exactly.Nathan: [00:44:50] What are some of, of those other things? And then we’ll obviously point people in the show notes to the thread about Twitter threads. If we can get more meta than that.Dickie: [00:44:57] Okay. The first one of the big thread was just advanced Twitter tips and it was things like how to create lists, how to block, meet words. So that one is a little less prevalent, but I wrote one breaking down. Why I thought that one was successful. And that is kind of my approach to thread writing.And so a couple of just small ones, his eye of the camp that every tweet should act as a standalone. So I don’t number things because you’re able to engage and pop in and reply to single ones on your own. I think there should be. 90% of your thread success is going to be the very first tweet. And it’s just a exercise in copywriting.And we’ve seen all the trends of, you know, time for thread or capitalized thread, those come and go. And once people get sick of reading them, there’s a new one that comes out that kind of captures people. So that one is something we’re spending more time on than cause at the end of the day, like that’s the click-through rate, the better that you can get people to.You’re just clicking on an article in the same sense. Right? So however you can. Write your copy too, to bring that up. and then just, if you break down the virality of it, it’s people share things that are educational or entertaining. And so you should very clearly see which one, like Sean periods, clubhouse thread, that’s the funniest, one of the funniest things I’ve ever read.And there was just, no, it was as long, it was the longest thing I’ve ever read on Twitter, but there was no way I was, wasn’t going to go back up to the top and share it. And speaking of which, I guess one last tip is after you post one, you can quote, tweet it at the very bottom to give someone kind of a call to action, to jump back up to the top, to share it.So it’s, Hey, if you enjoyed this. You know, jumped back up to the top and, and share it with your, with your followers and then they can tap right on it. And it brings it back up because so often you get to the bottom and it’s just, you just swipe away. It’s, you know, I’m onto the next thing, but this is, this is a way to say, Hey, if you enjoyed this, you probably forgot that this started up at the top here.They can click on it right away and share it. So it’s just, you know, empathetic writing, getting them to do a little bit less work to go up and, and share it.Nathan: [00:47:01] Yeah. And that works well for you. And so one thing that you could do is if you had some popular threads in the past, you could even put that tweet at the very end referencing, you know, doing the circular reference and that, you know, would work well to, make the thread more effective going forward.And as you were saying, it would resurface the thread almost like a retweet would.Dickie: [00:47:23] Yeah. There’s like a, there’s a. Ecosystem of content you can start to create. Once you have a bunch of threads on a bunch of different topics, it’s like, Oh, I’ve already covered this here. If you want to learn more about it. So, and it it’s a, like a Roam Research of, of Twitter, which they don’t do a great job of, of working out.But there’s like a way to link all your content together in a way that’s almost immersive. Right? You can just jump around and stay down the rabbit hole.Nathan: [00:47:48] have you noticed something like on threads? You’ll see people, you know, do take Mario for example, with it, you know, club, he’s writing all of that up. And then at the end, he’s usually linking to like, go read the full piece. Ha when that’s buried a little further down in the thread, do you think Twitter penalizes that?or do you think that works fine to link people off if it’s at the end, right? Yeah.Dickie: [00:48:14] I think that works fine. I think it’s on the tweet level that you will, are penalized for a link. So it’s not that they like sense that you’re trying to do it at the bottom. I think it’s, if it’s like a simple statement of, if this contains a link like penalize share-ability.Nathan: [00:48:30] How that’s fascinating. What about media? Like, I think about a thread, from Andrew Wilkinson that he did on, it was like the. The real story about private equity firms and being bought. So it was like a mix of his, his experience plus general experience and all that. And his media all the way through was mostly like Scrooge McDuck, you know, gifts like diving into gold coins.And like, it wasn’t that relevant, but it didn’t make it a lot more engaging. And so I’m curious, does obviously the image to get people to click in and pay attention, but he had an image tied to every single one.Dickie: [00:49:11] Yeah, I have. I’ve noticed that I have, more pure text, mostly because I’m not creative enough to like figure out an image for every single one. But. Some like Sahil, Blum who writes tremendous threads on, on finance does a lot of images and everyone just to kind of give it some context and some texture, I think it is.And I’m sure it works for, for everyone. Right. But, it’s not something I’ve particularly explored, but I think it’s, I enjoy reading them when they’ve got some kind of image or a little video clip here and there. or gift that, that keeps the reader going.Nathan: [00:49:43] Somebody else that I want to touch back on is you mentioned you don’t number threads, or like, you know, this is tweet four of seven, which is something that always annoys me for whatever reason. when people number the threads, I feel like, I don’t know. It makes it feel like non-native Content.Like it doesn’t actually belong on Twitter. it, and like you were saying, each tweet can’t stand alone and often you’ll find that where you’ll click you’re seasoned and retweeted you back. Oh, that’s interesting. You click into it to see the replies, and then you realize that it’s actually tweet five of a 25 tweet thread.It’s not even the beginning of it. for some reason, it just seems less engaging when you’re putting something in there that is not necessary for the tweet itself. So I think that’s a really good point.Dickie: [00:50:34] Yeah, like the one flash, it just, it, it doesn’t do much, you know, it, it takes away from the flow of it. Right. That’s how I feel.Nathan: [00:50:41] Yeah, that’s good. Keep bringing it back to newsletters. so Twitter, these days is one of the biggest channels that people are growing newsletters. how has your efforts on Twitter? How has that played back for your newsletter? And what’s worked to drive, subscribers or followers from Twitter to newsletter subscribers.Dickie: [00:50:59] I haven’t done. So my newsletter is it’s just a curation of links that I’m interested in, on. I just really call it growth. So growth of companies, people, systems improvement, that kind of thing. I have had really three events. I think I have like 2,900, 3000 subscribers on my newsletter. because I’ve kind of focused more on Twitter.I feel like I could start to share my news that or more to drive traffic, but the three that had one of my very first successful threads, I wrote one on biology’s tryna Boston, that Naval picked up and I went from 300 to a thousand Twitter followers. And. From 250 to 800 newsletter subscribers, just cause I popped it at the bottom.And that was, I like to say it took 40 weeks to get to, to 300 in about nine hours to go to to 800, which is just how it goes. Right. but I have, my newsletter has turned more into just kind of a personal thing and the, the growth of it, I’m less focused on because there’s not. Everyone has enough curation his letters.I’m really writing it for me at this point. Will I take it to a different medium or something in the future, maybe, but, today it’s really just, you know, I’ll tweet it out and pop the link at the bottom. every, every Sunday when I write it, but nothing too, too crazy.Nathan: [00:52:25] Yeah. That makes sense. Is there anything that, as someone let’s say they’ve got 10,000 subscribers or 5,000 subscribers, they’ve got some traction. Is there anything that you would want to leave them with of things that have worked really well for you that you think other creators listening should, should take into account?Dickie: [00:52:42] Yeah, one of my biggest lessons learned on the content side was from Sahil, who I mentioned earlier and it’s create great content, but don’t underestimate the importance of distribution and for a lot of us Twitter, especially if, or whether it’s your newsletter. You want to feel confident in sharing the things you’re writing, right?So it’s almost this forcing function where if I say every thread that I write, I’m going to DM it to 10 people who I think will find it valuable. I know that I’m going to put more effort and more refining into my content, but at the same time, that’s going to force me to create better content. They’re going to be more likely to share it.And so I’ve fallen into this trap of, “Oh, I’ve, I’ve hit that 10,000 Mark enough people are reading.” You never know, they could be on an off day. And so hustle for distribution and take it seriously, I think is the biggest lesson that I’ve learned and the result is better content and just more growth.Nathan: [00:53:46] Yeah, that’s great. Well, where should people go to follow you on Twitter? Subscribe to the newsletter, check out the course and everything else?Dickie: [00:53:53] Sure. So on Twitter, I spend way too much time. That’s @Dickiebush, D I C K I E B U S H. I’m sure you’ll find me there. If you want to learn more about Ship 30 for 30, Ship30for30.com, and my newsletter is Dickiebush.substack.com. So I keep it simple. And yeah, the DMs are open. Reach out.I love to chat, and you’ll definitely find me on Twitter that’s for sure.Nathan: [00:54:21] I think what we’ve established for sure is that you’re very accessible on Twitter. Well, good times. Thanks for coming on and we’ll chat soon.Dickie: [00:54:31] Cool. Thanks Nathan. I appreciate it.

Jason Feifer is the Editor in Chief at Entrepreneur, an American magazine and website that carries news stories about entrepreneurship, small business management, and business. He also hosts a podcast called Build for Tomorrow, and he is the author of a forthcoming book titled Build for Tomorrow, Not for Yesterday.Jason is a unique blend of individual creator and polished corporate employee, so he offers a balanced perspective on work and content creation. In this episode, Jason and Nathan discuss: How to package your work How to pitch your content and get press as a creator Time management for creators balancing full time careers Links & Resources Entrepreneur Boston Magazine Men’s Health Fast Company Maxim James Burnett Marc Andreessen Pessimists Archive: @PessimistsArc Louis Anslow: @LouisAnslow Andreessen Horowitz Joel Weber Jason Feifer’s Links Personal site: jasonfeifer.com Jason’s Podcast: Build for Tomorrow Jason’s forthcoming book: Build for Tomorrow, Not for Yesterday Jason’s Instagram: heyfeifer Jason’s Twitter: @heyfeifer Episode TranscriptJason: [00:00:00] You make the thing that you want to make. You believe in it, and you don’t give up on it, and you spend years doing it. And if you’re good at it, and if you were right that this was a thing that was worth making, people will find it because good really does rise up. It happens slowly, but it does happen.Keep going. Nathan: [00:00:23] In this episode, I talked to Jason Feifer. Jason’s the Editor in Chief of Entrepreneur. And we dive into a bunch of different things.One, how he splits his time as an individual creator and, you know, running a very successful, very popular magazine. How he blends those things. He’s got a newsletter, he’s got a podcast, he has several podcasts. He’s working on a book, all of those things. So how he prioritizes his time. All of that.The monthly cadence that he works on, I found really interesting. We also dive into how to package your work. We talk about why he changed the name of his podcast and the research that went into that. Then finally we wrap up by talking about PR and how to get press as a creator, how to think about pitching each individual publication, the work that you need to do to actually get covered a lot of good stuff.So let’s dive in.Jason, welcome to the show.Jason: [00:01:15] Thank you for having me.Nathan: [00:01:16] So I want to dive in, you’ve got two very different things going on. They’re actually, I mean, they’re closely related, but, two different worlds, you know, with everything you’re building on your own audience. And then of course, as Editor in Chief of Entrepreneur, I’m curious just how you spend your time, as I would think the Editor in Chief is a very time-consuming thing. Then you’re building an audience. You’ve got two young kids, you know, you’ve been doing it all through a pandemic. And so I’m curious what, you know, what a day or a week looks like, in Jason’s life. Jason: [00:01:51] it looks like panic. It looks like absolute mass panic. That’s how I feel. Panicked. Okay? So first I’ve made this, I made this realization a couple, more than a year ago. I can’t remember when this took place for me, but I realized that I needed to maximize how my brain works, like work with my brain.Right. Which is to say, when am I best at doing various things? And then let’s make sure that I’m doing those things at that time, because if I can write a full, like 2000 word story, in, let’s just say two hours, which sometimes I can do, that’s going to happen in the morning. If I try to do that at 5:00 PM, it’s going to take four to six hours.So why on earth would I waste my time doing tasks when I’m not primed for them? So I clear out the for if I can manage it up to noon, but that’s almost impossible. So really can I safeguard the first hour and a half of my day for writing? And then what I do with that hour and a half depends upon the needs that are most present for me.So for example, sometimes it’s writing a magazine story. Sometimes it’s writing a chapter in my book. Sometimes it’s writing a podcast script and this is dictated by the deadlines that I have. And then the rest of the day, I’m trying to manage everything that needs to be managed. I’m answering a lot of questions.I’m getting on a lot of calls, but I will, Oh, I, if I can. If I can do it, which I can’t always do, but I can do it. Then I will not book anything back to back. I will always block out like a half an hour in between. And that’s because things are coming at me and they’re coming at me for lots of different projects.And it’s hard. You can, you think that you can switch gears really fast between one project and another one company in another, as I’m sometimes doing, because I have my own company and then I’m also working with Entrepreneur and I mean, I, I mean, I’m employed by Entrepreneur. and so I need that time to make those shifts.And the days that I hate the most are the ones, well, first of all, where I lose that time in the beginning, but also where I’m back to back and I never have time to catch up on any of the inbound because that’s when I’m working late into the night.Nathan: [00:04:13] Yeah, that makes sense. Are there other things that you’ve found? Right. So writing in the morning is something and I can absolutely relate to that where like 3:00 PM. Nathan is, he’s actually just legitimately terrible writer. He wants to do anything, but Write, are there other things that you’ve found of like blocking off days of the week to focus on.You know, one activity or one business or anything like that.Jason: [00:04:35] I don’t, I have too many constant demands to be able to block out full days. I would love to be able to do that. So instead, I tend to think about things in terms of goals for a week. So I know for example, here’s, here’s an example. I know that my Build for Tomorrow Podcast comes out on the last Thursday of every month and it’s a monthly show, which I know is not a great cadence.Yes, yes. I’m aware, but it is such a deeply researched, highly produced show. It is, it is a months worth of work that goes into every episode. And for reasons that we can discuss I’ve decided that that’s okay because the. Ultimate goal of a podcast. Isn’t always just to have a bazillion listeners of the podcast.Sometimes it can serve other purposes. And for me, that show is also an IP factory and for good reason. So anyway, we can go into that, but I, I, so that comes at the last Thursday of every month, which means that I get it to my, I record the previous Thursday. I give my editor a week to put it together because that show has like 50 different audio files and there’s a lot of editing that goes on.And so that means that I know. The leak the week leading into recording week is when I have to have that script done, I am polishing that script. So now that enables me to prioritize all of what I would think of as the kind of free writing time. So there are, there are, I’m pretty sure things during my day, what, what needs to happen?What needs to happen fast? What is the project that I’m going to be chipping away at for a week? And that is the week where that’s the project. What’s the week before that’s the book project, because that’s the time in which I don’t need to be focusing on the PO. Podcast. I can be chipping away at the book and these, this is the way I think about it.I almost have to kind of dual track everything. There are the things that are going to be required of me day to day. And then there are the things that I’m going to be working towards as steadily as I can. And I’m building in the time for the hiccups so that I know there’s going to be some day where there’s some unbelievable fire at Entrepreneur that I’m going to have to put out and which I’m doing right now, in between, us having this conversation, there are like 40 fires that I’m putting out.And so I had to shelve a bunch of my stuff. I’m not working on the book this week. Instead I’m dealing with like a cover that fell apart and me having to write two features. And that’s fine because I’ve built that into the expectations of, of how I set my deadlines and how I’m working on these dual tracks at the same time.Nathan: [00:07:02] So you, you tend to think about things then on this monthly schedule, is that, did that start from the Podcast being monthly or were other things already contributing to the way you view it in, in a monthly schedule?Jason: [00:07:16] You know, it started, I think, from running a magazine that’s right. Like I’m trying to think through what do I have to do? And then what are the patterns of work related to doing those things? And then how can I try to get them all to sync up? And so I know for example, that a, a monthly magazine. So, so let’s talk about the monthly magazine for a little bit.So when I worked, I’ve worked at a lot of magazines. My first magazine job was Boston Magazine. I’ve worked at Men’s Health, Fast Company, Maxim, Entrepreneur. Those are the ones that I’ve had full-time jobs. And then I freelanced for a ton of others. And there’s usually this thing called ship week at a magazine.Ship week is the week in which everything’s getting finalized and literally shipping to the printer. And that week at every magazine that I have ever worked at, but not run myself, which is to say every magazine that isn’t Entrepreneur that week is hell. Like when I was working at Boston Magazine ship week, I would be there till two in the morning.What are we doing? It’s a monthly magazine. What possible now? I think back. And I’m like, what? Possibly kept us there until two in the morning. That is insane. And the answer is that we were doing. We’re doing a lot of BS. That’s what we’re doing. We’re doing a lot of BS. Right? So what, what was happening? I think back to that now, and I promise to get back to the point, but I think back to that now, and I’m like, what was keeping us there?And then I think, Oh, I know it was that. My Editor in Chief would come by my desk at like eight or 9:00 PM. And he would have circled a caption on a photo. And he would have said, you know, I think that this caption can be funnier. And then I would have spent an hour writing 20 different captions, and then I would spend another hour waiting for him to finish whatever other thing he was doing so that he could look at these captions.And that’s how you end up at the office until 2:00 AM. And when I took over a mag, I took over this magazine. I have a much smaller staff than any other, any of the other jobs that I’ve ever worked at. We have a tiny, tiny staff making Entrepreneur magazine. You would be shocked if you know, Entrepreneur, the brand, the magazine, whatever.It’s a, it’s an international brand. It’s been around for 40 something years. It’s very, well-respected. The staff is tiny. And so I am, I I’m thinking to myself when I took over this job, how am I possibly gonna keep quality up with this few number of people? And the answer is stop doing all the stuff that doesn’t really matter, right?Guess what? Not a single person in the world. In the world has ever purchased a magazine because they think the captions are funny. Not Write, not, not that Editor in Chief who, you know, God love him. James Burnett. he’s a friend of mine now, but by editor-in-chief bust magazine was asking me to do stuff that ultimately didn’t matter.And so I’ve caught a lot of that stuff out. And consequently, we don’t have an Entrepreneur hellish ship weeks. We just don’t. Instead what we have is a steady, steady workflow. And so I reorganized the way that we do things and I just decided to stop caring about things that didn’t matter that are nice to haves, but not need to haves.And, and therefore I adjusted how this thing is produced and I created a level of consistency so that I know the general flow of what I’m going to be needing to do when every issue to get this thing together. And then I can start to schedule all of my other needs around it. So it’s nice to have projects that have long deadlines and short deadlines, a short deadline, for example, Is a story that I have to write in a week.Okay. I know exactly how to budget my time for that. Then I’ve got like a mid sized project every month. I got to produce this Podcast. Okay. Let’s set that schedule. Let’s know exactly when the deliverables are and we can work backwards from there and make sure that the heavy workload on that doesn’t correspond with the heavy workload for anything else that I’m doing.And then. You’ve got the super far deadlines. Like the book I got to turn, we’re talking, I am talking to you on, on April 5th, 20, 21. I got to turn this book in, in like September, October. So I got some time and that doesn’t mean that I want to burn that time. I actually always, I’ve programmed myself to think that I’m always behind.I, that’s another reason why I’m in a panic. I’m always behind on this book, even though it’s due in October. But the reason is because I don’t want to get to September and be like, Oh my God, he didn’t write the book. So instead I am always working on it whenever I don’t have anything else pressing to work on.And that is the way that I have these tiers of deadlines and these tiers of things to do so that whenever I don’t need to be doing one thing, I have another thing lined up, ready to go.Nathan: [00:12:01] That makes a lot of sense and I’m fascinated by it because I’m in this position similar to you of, you know, having a full-time job, running a company, running ConvertKit and then also being like, Oh yeah, I do a podcast and I have a newsletter and these other things, and it’s, it’s a challenging thing as a creator to have two jobs.But I think, you know, in this case you were an I R R. Running the show at those things. But, you know, a lot of people have that full-time job that they’re having to do, you know, the same thing. And so just thinking about that for everyone, listening is what are the schedules that your job naturally has?And then you hit, might have an answer to why is your Podcast monthly, or why is it weekly, or why does it have this cadence? And it might be because that is the natural cadence to my life and it, it fits in. SoJason: [00:12:47] Yeah. And you know, and it’s also look, you, you set on anything that you can, that you control, you set the rules. And so, a friend of mine, or yeah, a friend, a friend of mine, I was like, do I need to give more detail? No, I don’t. A friend of mine recently asked me a bunch of Day has been asking me a lot of advice about a small publication that she wants to start.She is employed at a large publication. She wants to start her own publication. And one of her questions to me recently was. Is it okay. She’s like, she’s like I have, you know, I have a bunch of material, in the bank because that’s something that I always advise people do is don’t put yourself on a crazy treadmill, have a bank of materials so that you’re not responsible for creating the thing.That’s about to go out the door. Like, do you have a buffer? That’s great. I mean, look, I’ll be honest with you. I don’t have a buffer on everything that I do, but, and, and she said, well, what if I, what if I, what if I start running weekly and I run out and I’m not able to keep up and then I have to skip a week?What then am I answer was well, Okay. You set the rules, you, you are creating this new project. You are establishing the expectations of the audience, whatever you say is what it is. So do the thing that is manageable for you, and then make that, the thing that your audience comes to expect, because there’s just no reason to set some rule for yourself.That’s going to drive you into the ground. Can you do it? Yes. Can you find some schedule in which you can do it in then? Great. Do that. You can always increase it later. You can always change it later, but don’t, don’t cut your, don’t make something so difficult for yourself that you’re not able to achieve it, fit it into what you have available and you know, Nathan you’re right.You and I, we, we run the show and so we have more, we have more, control in a way, but you know, Something, my parents told me that I remember about myself is that in grade school they noticed, and they always thought that this was a problem. And only later realized that it wasn’t a problem. They always thought that it was a problem that I would, I would get into class every, every school year start young, start middle school.I remember doing this and I would figure out what is the least amount of work that I need to do to do a good job here? What is, what is passable? Right? Because, I don’t need to burn myself out on this math class in ninth grade, right? What is the least amount that I need to do to pass this thing so that I can spend my energy and time on other things that I care about.And that is frankly, still how I operate. That is how I’ve operated my entire career. Put me in a job. I will figure out how to do a really good job doing that with the least amount of effort that’s required. And then I’m going to take the rest of my effort and I’m going to build other things for myself.This is what I do.Nathan: [00:15:49] I’m curious, what other, you know, lessons or takeaways from how you run Entrepreneur, other creators who would want to see, like, I think that that hell week that you described is, you know, at a, at a previous publication is what a lot of people are used to, you know, as they’re writing their weekly newsletter that comes out every Monday or something like that, like they’re experiencing hell week.But kind of every week and they have the worst possible boss who is themselves. And so like, what are some of those other things you’d recommend to go to that smooth fluid process?Jason: [00:16:22] Yeah, it’s great. It’s great. So, I mean, you know, obviously everybody in Entrepreneurship rightfully talks about culture, creating the right culture and one of the big things, and I don’t know how many people ever think to do this, but because I came out of this world where there were these hella ship weeks and there was hours and hours spent on captions.I’ve started to, I created a Cory culture and Entrepreneur that we pride ourselves on not doing what we all previously did at other companies. Yeah. Like that’s, that’s a point of pride because I have, I have an amazing, it’s a small team. It’s an amazing team, right? It’s, it’s a team that have worked at just the greatest magazines in the world and they are all for one reason or another working at Entrepreneur now.And, and, and we, right. So, so Judith, my photo director and Paul or creative director, I mean, you know, these guys are guys are working at the New York times, T style magazine and, and, and Paul’s has been the creative director of like three different magazines. And we all know what BS looks like. And so a big part of our culture is we are doing things differently.Like we are, we are not going to sweat the small stuff. We are going to make a really high quality product, but we’re not going to drive ourselves insane doing it because we’re only going to focus on the stuff that really matters. What do people care about? What is quality and how do we be realistic about what we can create within the resources available?Because we all know. That if you were to give us millions more dollars and like a giant staff that was 10 times the size we’d make a different product. Yeah. We would make a different product, but that’s not what we have, what we have or the resources available and the talent available, and we can still make something awesome.But we have to think about it differently. And so I, I would say, you know, to, to your, to your question, number one is you, you set expectations in a positive but realistic way. What is the best damn thing that I can do with what I have available to me without focusing on what I don’t have available to me?Because if I showed up to work every day thinking, Oh my God, this team is so much smaller than what I had when I was at men’s health. Well, then I wouldn’t get anything done. So I’m not focusing on what I don’t have. I’m only focused on what I do have. And then, you know, the, the other thing, you know, as I, as I think through what we do at the magazine is we.Cultivate. And then we work within trust. So I trust the hell out of the people that I work with. They don’t hear from me probably as much as they should because frankly I’m super busy. And so I trust them. I let them, I let them do you know when Paul and I, Paul, my crave director, we both worked at Maxim together and Oh my God, the amount of like reviews that we all had to go through, there were 14 different reviews.We’d sit around the room and we’d look at every photo and we decide, okay, well, these are the photos, but now let’s review it again. In two days, we don’t have time for that. I don’t have time for that. I trust Paul. I trust Paul and he’s going to make those decisions. He’s not going to run it by me. And I’m going to look at it eventually.And every once in a while, I’m going to have some feedback and Paul’s going to have to tear something apart and he’s not going to get annoyed at me. You know why? Because I gave him so much leeway in every other aspect. and I just find that this is a better way to operate, have a team, trust them, know that you are all doing something great because you’re doing it differently than, than others.And you are going to make the best thing possible without driving yourself into the ground, because frankly, you got to do it all all over again. Next month. I, I can’t, I can’t afford having my team stuck in the ground. We gotta be moving.Nathan: [00:20:13] Yeah. And th that’s a great point about, you know, you got to build for longevity because nothing important is going to happen in a month or six months. And if you burn people out in that amount of time or burn yourself out in that time, then you can’t do anything longterm.So when it comes to all this stuff that you’re building on your own, cause.One thing that, you know, people point out to me when I’m trying to do everything. So like, you know, you don’t have to Write, like you don’t have to have a podcast and a newsletter and a blog and, and like all of these other things. So talk a little bit about why you’ve ramped up the personal side, you know, your brand, your audience, your Podcast, all of that more so when you already have an audience through Entrepreneur,Jason: [00:20:58] Right. So I, out of curiosity, this’ll fit into my answer. Do you have an answer to what the point is? What’s the point.Nathan: [00:21:07] that’s a good question. I mean, the first thing that came to mind is like, at this point, I’m just having fun of like, what are the things that interest me, you know, like, I mean, rebooting this Podcast, like I did this Podcast. I dunno, six years ago or something. And then I brought it back mostly because I found that I was sitting at home and not talking to anyone.And like, I had all these questions for people that I like and respect. And I was like, this is the best format to get onto it. Lots of people listen to the show. That’s great. I don’t care.this is the part that I’m optimizing for in this case. And so, yeah, that’s not an answer to what’s the point, butJason: [00:21:45] No. Okay. Well that’s fine. I mean, no, but, but you answered it, you answered it because you have the, you have the same answer that I have, which is that I’m not really sure. Right. That’s it. That’s your right. We know, we know that we like it. It’s enjoyable and it gets us things, whatever those things are, they could be all sorts of different things.But what’s the, what’s the ultimate point. I don’t know. What’s the point is to do it. So now let me tell you my philosophy called work, your next job, because this is really the answer. Okay. Here, here’s something that I, throughout my career, even when I was a rookie reporter at a small town newspaper, which is where I began, I.When I was a rookie Wilkie when I was, when I was a character on star Trek, when I was a rookie reporter, as I worked at the gardener news, 6,000 circulation, daily newspaper covering nothing, nothing was happening and in garden messages. And, and I really wanted to work for giant publications.That’s I didn’t know what I did. I couldn’t have explained it to you. I was fresh out of college, but I was like, can I work for the New York times, the Washington post, just large publications. And, and eventually I realized, you know, these people who work at the places that I want to work, they are never picking up my newspaper.They are never reading this great story that I just did about the middle school play. And they are never reaching out to me and saying, kid, bring me up to the big leagues. It’s never happening. Right? Like it’s never happening. And so I needed to go to them and that was the only way I needed to go to that.I needed to go prove to them because you know what I wasn’t going to do. I wasn’t going to follow the normal path of like a tiny paper to a larger paper, to a slightly larger paper, to slightly larger paper, because I would be 89 years old. But before that, before I reached anything and so I was like, I’m going to skip all these steps.And, and that means I’m going to quit this job. And I’m going to freelance and I’m going to just go pitch and pitch and pitch to these, to these publications. And, and, and after like sitting in this tiny apartment next to a literally next to a graveyard and Holden, Massachusetts, I, for like for like nine months pitching, I, you know, I got some stories in the Washington post and the Boston globe and a couple others.And then I took this, I took another small newspaper job because I was lonely and I needed better income. And then I just kept freelancing, on the side because I realized, okay, I’m going to take this job. I’m gonna work this job. It’s gonna pay me. And it’ll, it’ll serve some kind of function in my, in my ladder, up in my career.But I think that the real answer here is actually the freelancing that I’m doing on the side. And so I’m going to keep doing that and that’s, and then I just kept doing that throughout my entire career. And I eventually, I eventually came to this philosophy about it and it was called, I call it work your next job.So work your next job. You may, everyone listening to this in front of us right now. And yesterday and tomorrow, all the time are two sets of opportunities. Opportunity set, a opportunity, set B opportunity, set a is everything that is asked of you show up to work. What does your boss need? What are your KPIs?What is asked of you opportunities to be is everything that is available to you that nobody’s asking you to do. And my argument is that opportunity set B is always more important. Just always, it has always throughout my entire career been more important, which is not to say that the jobs that I work or not, because I, you know, obviously I guess, I guess if, if the.CEO of Entrepreneur was listening to this right now. He’d be like, wait a second. You’re just telling me, you’re telling me that you are deprioritizing Entrepreneur. And like, you know, like it’s important. I get it. It’s important. I want to do a great job. But when I think about the future of my career and not knowing where it’s going and not knowing what opportunities are ahead, what I know is that focusing on opportunity, set B prepares me better for the future, then opportunity set a alone does because if I only focus on the things that are asked of me, that I’m only qualified to do the things I’m already doing, but opportunities at B is where I learn and where I grow and where I become better.So how did I become Editor in Chief of Entrepreneur magazine? Well, there’s a lot of answers to that, but here’s one of them. One of them is that like many, many years prior, I worked at fast company and I was a print editor. My job was to edit front of book sections and print features. And then they started a video team and I.I had really no experience on camera. And nobody asked me to be a part of the video team, but it sounded interesting. And so I started doing it and I developed a knack for it. And I absorbed everything that the video director said. And I ended up, I created two series, like I had like a weekly, weekly series and then one where we actually traveled around.It was super cool. And I got a lot of experience and, and I got really comfortable on camera and because I got comfortable on camera, I also had the raw material to get comfortable on a microphone. Like you hear me right now and also get comfortable on stage. And then what was that for? I don’t know. I didn’t notice for, yeah.Did I ever get a TV show? No, I didn’t got a TV show, but years later I am interviewing to be Editor in Chief of Entrepreneur magazine. And one of the reasons that they really like me is because I can represent the brand really well. I’m good on camera. You can put me on stage and I’ll be really good.Where does that stuff come from? It came from me doing it at random, at fast company that nobody asked me to do. It was opportunity set B and now it is creating a new opportunity at Entrepreneur allows me to be Editor in Chief because I’m good at this stuff. So that’s why I do it. Why did I create the podcast?I don’t know, because it seems like it’d be useful. Why am I doing the newsletter? I don’t know. It just seems like it’ll be useful. I’m just doing it because I don’t know what the ROI is, but I know over and over and over again, because my entire career has proven this to me, that focusing on opportunities at B is more important.So figuring out how to do it, find, find a way, find the time. That’s my philosophy.Nathan: [00:27:42] I like it. And I think I’m driven a lot, the same way of like, what’s going to, you know, what’s going to push me. What, where am I going to learn? If I have two options in front of me, like air B. Like, it’s always choosing the one where it’s like, I am going to have to learn something I’m going to have to end up being a front person to achieve that goal.Whereas this one is like, I don’t know. I think I could do that with the skill sets that I have. And so it’s pass on that and go to the one that requires a newJason: [00:28:08] Yeah.Nathan: [00:28:08] a new set or something.Jason: [00:28:10] I mean, look, I, I, I’m sure that there are, I’m sure that there are people for whom they develop a skill set and they’re good at it. And then they’re really satisfied just doing it throughout their career. And if, and if that’s you, then congratulations, because you found an easier path and that’s wonderful, but if that’s not you right.And it’s not, it’s just, yeah. Like what you just described. It’s not me. I remember a couple of years ago. Well, more than a couple of years ago before I was an Entrepreneur. And I had, like, I had always aspired to be a really good magazine features. Editor only I could be a really good magazine features editor and, And then I became a good magazine features, editor.Like I just know how to do it. You know, it’s like, it’s a formula. I apply it. I just know how to do it. and then I remember editing some story. I can’t even remember what it was. And I was just like, Oh, is this it? Like I got here and not now, do I just do this forever? This is terrible. Like, I hate this, this thing that I really wanted to do now, I hate, I felt trapped in it.So I always want to be adding. And you know what, when you’re constantly adding, it means that relying on the things that you know, how to do can be comforting and satisfying. And also you discover that things that you became really good at in one way are, are, are actually. Useful raw material in learning something else.So, I mean, do you listen to how, I didn’t know how to make a Podcast, but I, I, what I did is I was like strung together these skills from other things talking on camera, but also I learned knowing how to write a magazine feature, translated into knowing how to write a Podcast script. They’re totally different, different styles of writing.It took me a while to figure out the pacing is different. The needs are different. You got to signpost everything over and over again. Oh. But like it’s the raw material was there. And so it felt like I was utilizing something that I had worked hard at, but without being trapped inside of it, because I was using it in a different way.And that in a weird way, felt liberating.Nathan: [00:30:02] well, I want to ask about that because with the Podcast, almost everyone just doesn’t interview show. And I feel like we can make fun of interview shows. Cause we’re on one right now. And it’s like, you know, you and I both know they’re there, they’re easy, like 30 minutes of prep. You’re, you’re good to go.I’m all of that. And it’s fun. Like they get engagement. All of that. Now the show that you’re doing like Build for Tomorrow is not an interview show. It is the high production, like crazy amounts of work goes into it. All of that, I guess. Well first why do that type of show? And I say that from the point of view of like someone who wants, like, I would love to do that show.I just know that I’m not willing to commit the amount of time to make that happen.Jason: [00:30:48] Yeah, no, it’s true. It’s a great question. I ask myself all the time. Why am I doing this? It’s so much work.Nathan: [00:30:53] The due date comes up. You’re like, what am I doing?Jason: [00:30:55] Yeah, I’ve made this so hard on myself, right? Like this is a really hard show to make. Right. So, you know, for, for, for those who don’t know, built for tomorrow is a show. My tagline is it’s a show about the things from history that shape us and how we can shape the future.And the idea is to understand the context, from history, of, of something that we’re experiencing today and then see what it teaches us about how we can be creators tomorrow. So our, my most recent episode for example, was it’s about, you know, the, you know, the, the thing that people always say, old people, I’m just gonna call it bold people.I’m insulting you old people. What old people say about young people, which is that they all got trophies as kids. They all got participation trophies, and that’s why they’re entitled now because they never learned that winning takes. Work. so that’s a thing that we’ve all heard and we, we could agree with it or we could disagree with it, but w but I will tell you, as I discovered, and this is what the episode is sort of hinges on, will tell you that we have all swallowed.A falsity about this story. And it is in fact, weirdly the most verifiable part of this story. And that is the idea that participation trophies are New. We talk about them as if, Oh, this generation, the young people today, they grew up with the participation. No, you know what, actually, if you look through the history, people have been getting participation trophies for a hundred years, one zero, zero, a hundred years.So all the baby boomers who are like millennials today and they’re participating, no, you guys got participation trophies. You did. I know you’re going to tell me you didn’t, but that’s because you don’t remember them because it wasn’t that important, but you did. You did. And so I, so I, to, what I want to know is, okay, well, where the hell did they come from?Which actually is a question about where did youth sports come from? And tell the whole story of where participation trophies came from and then apply that to today so that we can come to an understanding about what it is that we’re really frustrated about when we’re, when we’re talking about like generational changes.And blah-blah-blah because to me, my view of it is that like every generation is basically exactly the same, but we always talk about them as if they’re like some weird new species. And I think that that’s completely, self-defeating like the, the very logic of it falls apart on its face. If every generation was worse than previous generation, then you and I wouldn’t talking through riverside.fm.We were to be rolling around in mud somewhere because we wouldn’t have invented any of this stuff. But, but in fact, every generation gets better, not worse, so, okay. That’s the point of this, the show and. and so how do I do that? Well, I don’t just go interview one person. I interviewed like a bazillion people.And then, and I also dig through, newspaper archives and historical research and I, and then I like pull it all together into this script that goes on for like 9,000 words and has 50 different pieces of audio and the sound effects and music. And I hire actors to like read these old newspaper clips.And it’s a whole thing. Why to your question, why do I do this? and I will tell you, the answer is not to make money because, this show does not make as much money as it should for the amount of work. why do I do it? I do it for a couple reasons. One, because I’m okay. Doing something without knowing what the point of it is.I start without knowing what the ROI is, because what I want to do is create. And push myself. So I wanted to create a show that pushed me and I wanted to create a show that said to the world, Hey, I can do this really good, complicated thing. Right. I got, I, I just can, and I’m going to learn it and I’m going to become even better at it.I’m good at this. It’s a showcase. And what is it for? What’s the showcase going to do for me? I didn’t really know, but I’ll tell you what happened because I did it. What happened is that it developed an unbelievable community of really, really smart people, right? Like it’s like, it’s like when, when you get into bed and check your email, when you get into.When you get into bed on it, this is a real anecdote. When you get into bed on a cruise ship and your honor, and I don’t really like cruises that much, but I’m on a cruise ship because I was hired to speak on the cruise ship. So that’s pretty cool. And I saw getting into bed on the cruise ship. Where I was hired to speak.And I look at my email and I’ve got an email from Mark Andreessen telling me that my podcast is his favorite podcast. And when’s the book coming well, you know what? I did something good, right? Like, I don’t care. That’s what happened. I don’t care if the, I don’t care. If the, if the show doesn’t make that much money, it doesn’t, it makes some ad dollars.But like, I don’t care because it, it has attracted this unbelievable community of people and those people now I have access to, and they’re listening to me and they’re thinking of me as a kind of authority. And then like a foundation came to me and started throwing money at me, which is true. That happened.And then, and then I, I sold a book deal, which is going to be called Build for Tomorrow. Not for yesterday. It will come out in 2022. And it’s based a lot on the research that I did for the podcast. This is what I’m talking about. When I go like that wouldn’t have happened. If I just created a, like a little, a chat show, you know, people could do that.That’s great. That’s fine. And I don’t hold it against anybody because you know what. I’m marshaling my skill. I am aware of what I’m good at and also what I really like to do. And, I mean, whatever, I’m not gonna, I’m not going to dance around it. I’m a good writer. I’m a good writer and I’m a good performer.And, and I, and I want to, I want to harness those skills. And so I do. And, and I put it out into the world and took, Year’s Write Mark Andreessen. Didn’t email me like five minutes after I posted my first episode. He emailed me years after making this show, but he emailed me and now I can email Mark Andreessen whenever I want, because he likes my shop.And that’s awesome. So that’s what it’s for.Nathan: [00:36:47] Yeah, that’s interesting. I love the approach of quality over quantity. And I think about, you know, a lot of shows like that, like a hardcore history, for example, it’s one of those things where you’ve Notes. They don’t even have a consistent schedule. You’re just like, there’s nothing, no hardcore history episodes.And then like all of a sudden it comes out and you’re like, this is amazing. And people are talking about it and you know, that’s exactly what you’ve done is there’s the conventional advice of like, show up at the same time every week, you know, be super consistent for your audience. All of that prioritize consistency over quality when one of them has to go and I love it when you’re going the other way of saying like, no, let’s go quality all the way.And let’s find a cadence that okay. Works for that.Jason: [00:37:30] Yeah, I think that’s right. I mean, look, there’s something to be said for following standard practice. And if I could make that show, Ooh. If I can make that show on a weekly basis, I would. And, and maybe, maybe one day I will, who knows, but it’s not going to happen now because I don’t have the time. And so to, you know, it goes back to, I mean, it is you’re right.It is, it is not being hung up on quote unquote best practices, but it also like a lot of it is in what I was talking about a little earlier at Entrepreneur where I said, okay, I, our ethos is to be aware of the resources that we have available to us and then make the best damn thing with those resources.Right. And so I’m looking at myself for this podcast and I’m like, well, what are the resources I have available to me? I mean, to start it with just me. Now it’s a little bit more because now I have, I have some funding and I can hire like a reporter to help me out, but whatever, it’s still not that much.So I have, I have some resources and I have some time, not a lot of time. I got some time. What is the best damn thing that I can make given all of this? I guess I could have made a weekly five to 10 minute show, but I don’t want to do that. I want to go like crazy deep. I want somebody to listen to this show and end it and be like, Holy crap.Like that was everything I need to know about that. Right? Like that was the full story. And that’s just, that’s just how I wanted to make it. There were other ways to make it, but this is, this is how I wanted to make it. And sometimes I, it’s not going to, I realize this is not the way the world works and not everything’s going to be like this, but sometimes you just go out, you make the thing that you want to make you believe in it and you don’t give up on it and you spend years doing it.And. And, and if you’re good at it, and if you were right, that this was the thing that was worth making people will find it, it doesn’t, it doesn’t matter if it’s on a weird schedule. It doesn’t matter if it’s like a hard to explain. It doesn’t matter. People will find it because, because good really does rise up.It happens slowly, frustratingly slowly, but it does happen. And if you’re willing to commit to that, and if like making the thing that you want it to make is so satisfying, that it will propel you through all the years where like nobody cares where Mark Andreessen is not emailing you. Well, then, then keep going.Nathan: [00:39:52] Yeah. And I think so many people are looking for that. They hear that, you know, if you do the work, if you put in the quality, like that will rise to the top, but they’re underestimating, I guess, two things. One the amount of time that that might take, because that could take one, two, three, five years or more.but there’s also a packaging element to it. Like you recently changed the name of your podcast for you to, to talk about that because you’ve been doing the work and then you realize that you’ve been putting it in the wrong backpack.Jason: [00:40:21] That’s right. That’s right. And this was, this was an unbelievable lesson. This, this to me is really, I mean, there’s a lot of lessons in this, but I’ll just tell, I’ll tell you the story first. Okay. So the show was not born as built for tomorrow. The show was born as pessimists archive and pessimists archive was originally a Twitter feed.It’s still is a Twitter feed run by a guy named Louis Anslow and five years ago or something like that. I stumbled across this Twitter feed. And I don’t know if you’ve ever had this experience. Have you ever like come across something? And it was like, hi, I made this, but I didn’t make this, like, this looks exactly like something that I would make, but I didn’t make it.Have you, is that a, is that just me? Have you ever had that.Nathan: [00:41:04] Yeah. I’ve, I’ve definitely had that before.Jason: [00:41:07] Yeah. So for me, pessimists archive was that because I was obsessed yes. With this question of why our fears repeat across time. And I was like, I was a fast company at the time and I was digging through old archives and I was like writing these stories for fast company about this.And then here comes pessimists archive, which is doing the same thing. It’s like clipping out these old newspaper clippings about like why radio is addictive and, and all that stuff. And so I was fascinated. I was like, Oh my God, I didn’t make this, but I made it. And so I DMD pessimists archive and Louie responded, I didn’t know who it was.And we started talking and I was like, look, if there’s any way to like partner up, I would love to do something. And we decided to make a Podcast. He didn’t know how to make a podcast. I didn’t know how to make a podcast, but I had a media background. So I thought I could figure it out. And so I, we started, we started making the podcast, the first podcast, it took three months to make.And the second one is going to have three months to make a, this was a slow process. And, eventually it, it got traction and it started to get some of that attention. It was really exciting. And, and so the podcast is called pessimists archive and, and Louie ran the Twitter feed and I ran the podcast and, and it was, it was great.And then I hired mutual friends of ours, Adam and Jordan Bornstein and their, and their company, a pen name, Content. And, and they, I hired them to do growth on this podcast. And the very first thing that they did is they, we did some with, with, one of their team members, Rochelle Devo. They did some, she did audience insights, audience insight Research, talk to a bunch of my audience, dove deep with them and came back with this mind-bending report.And this report told me a couple of things. One of them was that the name pessimists archive was amazed, major barrier to entry. People thought that it was a pessimistic show. And I had heard that anecdotally people would have that and I’d be like, ah, idiot. Haven’t listened to the show, but now I’ve got like Research showing me people don’t understand the show because of the name and the logo.And, and like, if somebody can get over that barrier and start listening to the show, they’ll tell friends about it. And the friends won’t listen to the show. Like I was just, it was really, really interesting. And then also, I, in the earlier days of the show had really thought of it as a history show and Rochelle’s Research.Okay. Day revealed to me that people listened to the show. Not because they think of it as a history show, but because it helps them feel more resilient about the future, which is to say that I was making this thing, that I was thinking of his kind of like, you know, slightly academic and highfalutin. And in fact, people were having a kind of self-help experience with it.They were, they were listening and they were taking something away for their own lives. And when I had those pieces of information, I realized, wow, like, I can, I can take this and I can write, make it even more relevant to people’s lives. And I can take down the barrier to entry and open it up. And that’s going to be scary because change is scary and like changing the name of this podcast is going to be scary.And, it’s going to, it’s going to alter Louie and my relationship, which, which, which ultimately, for a number of totally mutual mutually agreed upon reasons ended mute Louie and I are separate entities now. Right. and, and, and I thought let’s, let’s do it. Like I preach that change is opportunity.That’s like the conclusion that I’ve drawn out of studying history and studying Entrepreneurs is like adaptability is where the opportunity is. So I got to do it myself. And so I, I changed the name of the show and I pivoted a little harder into where my audience was telling me they were. Right. Instead of it used to be the show used to exclusively be about like, why, why did it take 500 years for people to use forks?Which is, which is an interesting question I will have, you know, it’s actually a fascinating question, but, Write, I was interested in the repetition of fear across time. And like, people didn’t use forks for like most of humanity, forks are like a new thing. relatively speaking. And so, so, but I thought, okay, but if I can, if I can go the extra mile and find these historical stories that also inform our lives today in a very tangible way, then I’m going to have something that’s like taking the things that I love doing and keeping the tone and the essence of this show, but also making sure that it’s really delivering exactly the kind of value that I’ve just learned from my audience that they want.And. And that was, that was transformational. And that was, that was the thing that got me to the next phase where like, I couldn’t have sold the book. I sold this book to penguin random house for, you know, it was a nice deal. I couldn’t of done that without that transformation. I couldn’t have sold the pessimists archive book, but I could sell the bills for tomorrow book.And, and, and again, it all goes to, I couldn’t have possibly predicted any of that at the beginning. If I thought, well, I’ll start this podcast. It’ll lead to this and this and this and this and this and this. And then I’ll have a book. Well, I would be a first of all, I’d be Nostradamus, but like, that’s not how it works.You just do it. You do it. You don’t care about the ROI you get in there. And then you discover the opportunities along the wayNathan: [00:46:06] Yeah, absolutely. And I mean how you package it and, and you know, the quality of work you put in, but then Hey, position package, it makes such a difference. And so that’s kind of the last topic that I want to talk about is the PR side. Right? I think a lot of, a lot of people think about press and news stories and a lot of creators think about that, of like, Oh, that’s something that a big company can do.You know, someone Entrepreneur will want to write about Google. They will want to write about the startup, that Andreessen Horowitz just funded with $50 million or something like that. But they won’t want to write about me as an individual. even though I’m doing the quality work part of what I’m taking from your story is like, yeah, you have to do the quality work and package it in the right way.That makes it interesting. But I’m curious, what would you say to creators who, you know, are looking to get more conventional press coverage and more than just being mentioned in blogs or something like that? what systems should they put together? How should they think about their work?Jason: [00:47:01] Yeah. So there’s a lot to say here. Okay. Let’s, let’s start from what I was just talking about before audience insights. So if, if you’re in business, the idea of getting insights from your audiences is not a foreign one. Right. You know, you know, to do that. but people. Don’t think about how important that is or version of that is when they’re trying to get press, which is to say, if you’re trying to reach out to your audience, you want to get some insights about what that audience is looking for so that you can cater your pitch as much as possible.That’s how press works, too. You have to understand the publication that you’re pitching because big people tend to think and people tend to think because, and I get it that people don’t understand how media, people often treat media as if it is a service provider. I will get emails and the emails will say, how can I get a feature in your magazine?Which I read as, how can I get a hamburger at your hamburger? Right. I don’t sell hamburgers. I’m not a service provider. Right? I don’t, I don’t have ups. I don’t have a service for you. so, so what, what, how do you reach out? Well, the starting point. Is to understand that a journalist and, you know, and just speaking broadly here, a journalist doesn’t care about you or your business.They don’t, they just don’t. And you know what? That’s not a bad thing because they do care about something. You just have to understand what it is, what they care about is they care about their reader or their viewer or their listener. They care about their audience. They want to deliver great value to their audience, and they do that through storytelling.So they’re not here to serve you. They’re here to serve their audience, but if you can figure out how they serve their audience and the kinds of stories that they tell to their audience and the way that they tell them and the takeaways that they’re looking for, and just basically the thing that they are delivering value on and the form in which it comes well, then you can figure out how you can be valuable to their audience.And once you’re valuable to their audience, then you’re valuable to them. And that’s how it works. So what’s the customer insights. Let, I’ll let you I’ll use Entrepreneur as an example, if you go through Entrepreneur magazine, Entrepreneur.com is, is slightly different because print and digital products are, they’re just a little different.I can explain it, but let’s just make it simple Entrepreneur magazine. If you go through Entrepreneur magazine, what you’ll notice, if you think hard and close about the content that you’re looking at, you will notice that every story in some way or another is about a problem solved. It’s always about how somebody thought through some kind of challenge.It’s always about some kind of insight that somebody had some counterintuitive decision that they made something that drives them towards solving a problem and growing their business or growing their life, whatever that is not an accident. That’s the mission of the magazine. I’m not writing stories that are just like, I’m not, I’m not writing a Chronicle of every company that hit 20 million in revenue like that.That wouldn’t be interesting. Who cares about that? What I’m looking at is like, what can my reader, who is. Anybody, right. Anybody anywhere, what can they learn from this person that I’m writing about? And the answer is that if, if I’m writing about somebody who makes widgets, the person who’s reading, it may not make widgets.So they don’t care about how to make a widget, but they might care about what to do, know what to do. Like when the widget factory ran out of money and this person had to like figure out some solution. Well, that’s something that’s pretty relatable solving. The problem is broadly relatable. So that’s what I do.So when people reach out to me and they’re like, you know, What is the w w what are the qualifications of, of being covered? Well, there are, there are no qualifications, right? It’s not how, it’s not how it works. It’s not like, Oh, send me, send me a year, like financial disclosure document. And then I’ll take a look at whether you deserve coverage.That’s not how it works. What I’m looking for is value for the reader. Do you have a story? And do you have insights that are valuable to my reader? Yes. Well then I’m interested. No, well then I’m not a service provider. That’s how to think about it. So, so yes, you can get coverage. You don’t have to be Google, but what you have to do is you have to figure out who you’re pitching.You have to understand what they’re looking for, and then you have to cater your pitch to that.Nathan: [00:51:20] Thinking back to when you were the freelancing journalist, that you were doing all the way back then of coming up with stories and, and very actively pitching it to each individual publication.Jason: [00:51:32] Yup. That’s exactly what I was doing and getting ignored. Just like everybody who pitches media gets ignored. And, yeah, that’s what I was doing. I was pitching, I was cold pitching. I was trying to try to foster relationships with people. I was trying to get any kind of crack open in the door. And, and, and the way that I did it was that I spent time.I mean, you know, again, I’m pitching to be as a freelance writer, but it was really not that different. I was, I would, my first major piece was in the Washington post health section. How did I get it? Well, I spent a hell of a lot of time reading the Washington post health section. Like, what are they covering?How are they covering it? What. What did they just do in the past month? That leads me to an idea that isn’t what they just did in the past month. But seals feels like it fits in with whatever conversations they’re having over there. And then writing a pitch that’s catered to it and showing them that I’ve got the goods, right.That, that, because sometimes people will pitch things that, that have nothing to do with what you’re doing. And they think that just because they showed up, you’re going to like change the rules, right? Like, like people will, people will, people will send me their poetry. We will write poetry. Have you ever picked up Entrepreneur magazine and found poetry in there?No. Well then we’re not going to knit. Not once. Not once. We’re not going to start with you. Right? Like, it’s just, you, can’t just, you can’t just like assume that people are going to move the mountain for you. You can cook, go to the mountain. So, yeah, that’s what I was doing. I was studying the place that I was pitching.And then I, I didn’t know the person, Susan Morris. Yeah. The like health editor at the time, 20 years ago. I don’t know what she’s up to now, but she’s, she’s who responded to me. I didn’t know her. I couldn’t figure out anything about her, but I figured out her publication and I figured out what she likely was looking for.And, and, and I was right.Nathan: [00:53:19] I think that it might be projecting here, but, I’ll just do that. I’ll project my thoughts on to just all creators, because that sounds interesting. so you know, a lot of creators, myself included would think of it as like pitching a story, you know, about my company, about my creative venture or something like that is like, almost feels too forward, you know?It feels like, Oh, we should do this thing. That’s. You know, ancillary Daily related, and then it’ll get covered in the w we’ll get discovered or whatever else. And it sounds like what you’re saying is you should find the things that you’re doing in your business that match the way that that publication writes stories and all that.And you should like craft a pitch and write, you know, a meaningful amount of that story. Is that right?Jason: [00:54:07] That’s that’s. I mean, you don’t have to write the story for them, but you want to deliver the information so that they can see that there’s value. Yes, absolutely. I mean, right. It’s not, if you go out there and you’re focused on your agenda and I understand your, obviously the Royal, your Write, and everybody had been, you walk this, you want coverage and you don’t want coverage, to contribute to the marketplace of ideas.You want coverage to drive business. I get it. I understand. But, And, and so you might, you might, I mean, the way that you just framed it, there, you might have, you might feel some heads. I suppose somebody could feel some hesitation because they’re like, Oh, well, you know, who’s going to, who’s going to write this like glowing article about me, who am I?And yeah, you’re right. Who is going to write that glowing article about you? Because, because the, the, the profile, the like just general, here’s this company and they’re doing great things, but that’s not interesting. It’s not interesting to anybody. So what is the thing that you do that is distinct and that fits what this publication is looking for?Hey, here’s a, here’s one of my favorite examples. I got this email and this woman named Joelle is years ago and she has product called buttery. It’s a butter dish and it’s a butter dish on a hinge smart here. Why do you, why do you want a butter dish on a hinge? Like, you know, it’s just to save it. There’s like the bottom part of the butter dish and the top of the bedrooms and each sort of like, eh, like it opens up on a hinge.Why would you want that? Well, you would want that because it turns out you don’t need to refrigerate your butter. It’s not a thing that you actually need to do. You can keep your butter out and then it’s nice and soft and like spreadable. It’s great. But the problem is of course that soft butter is just super messy.So if you have a normal butter dish where you like lift the lid up and down all the time, you’re going to bump into the butter. It’s going to become big mess. But if it’s on a hinge, then it never bumps into the butter. It knows exactly where it is. Smart. Okay. That’s not for us, but that’s smart, smart, smart product idea.Because by the way, when I say solving problems, I don’t mean for Entrepreneur. I don’t mean that you like solved a consumer’s problem. That’s literally every business, right? Every business of solving a consumer’s problem, I mean that you solved a problem in your own business. So, because that’s the thing that’s gonna be relatable to other people.So, so she, she emails me about this buttery thing and I’m like ready to tune out. And then she tells me this fascinating little thing that she did, which sounds silly. I’m sure she thought it was silly to share, but it was great, which is that when she was first developing this thing, she was trying to, she was trying to figure out some basic questions.What’s the price point? What are the colors that I should sell this thing? And what do know? And she wanted to do some market research. She wants to market research company. She was like, how much would it cost for you to do market research on this? And they said $10,000. So she didn’t have $10,000. So what’s she going to do?Well, she doesn’t really know. And then one day she’s sitting at the airport flying somewhere and she looks around. And she has this revelation. This is pre COVID. She realizes the airport is full of people who have absolutely nothing better to do than answer questions about butter dishes. There’s, ain’t nothing better to do.Just sit in there. And fact, you could start at gate one and by the time we got to gate eight, everybody had gate. One is New. You could do just do it over and over again, and you can show up, right? You could, you could, if you’re flying out of an airport at 5:00 PM, you show up whenever you want show up at 8:00 AM.You have the whole day nobody’s going to kick you out. Right? So, so this is how she does her own market research. She goes to airports every time that she’s flying out, she spends like hours and hours going around asking people or just sitting around and answer questions about butter dishes. She doesn’t say that she’s the.Inventors, you just, you know, I’m doing some market research and this is how she does it. She saves $10,000. This is how she gets out into the marketplace. This is a wonderful story. I love this story so much because everybody Write people want to Podcast. Can’t skitzy you, but you’ve been smiling throughout the story because it’s so delightfully clever, but also relatable.And everybody in every business, it doesn’t matter what you’re in. Can appreciate the story. You hear it. And you’re like, I love that I can do something like that myself. Right. That’s what I’m looking for. Nobody cares about the butter dish. Everyone cares about how she did market research. Those are the stories that I’m looking for.That’s what I respond to. So, yeah. And you would only know that if you spent some time paying attention to the publication,Nathan: [00:58:15] Yeah. Well, that makes so much sense because when you talk about Entrepreneur as solving a problem, everyone is like, okay. Yeah, I solved all these problems for my customers, but you’re looking to solve problems for your customers. Your customers are the business owners, you know who, and so in this case, market research is a problem.Like there’s so many of these things that every business owner faces and they’ve all been like, Oh, I’m going to hire this agency. It’s going to be great. $10,000. I don’t know how, you know, everyone has encountered that. And so then, and you know, having that story to solve that problem is. Is really compelling.Is that something, do you feel like each publication Write sitting out Entrepreneur side, each publication kind of has that, that hook or that formula or their own style along those lines?Jason: [00:59:04] Yes, they do. They’re there. They’re all going to be different. And I don’t know how to articulate them for each one, but they, every publication has a, has a reader in mind and a mission statement. All right. So, so when I, when like my friend Joel Weber, who’s the Editor in Chief of Bloomberg Business Week.We had launched a couple of years ago and I, and I was just curious. I was like, Joel, what is the mission statement for, for Bloomberg business week? And, you know, I can’t remember exactly what he said, but it was, it was some version of, it was some version of like, we, we will tell we like what leaders need to know, or like, what is a leader in business today?Need to know? We’re going to tell them that started, it’s Write like major leaders in business today. What do they need to know? We are going to tell you, that’s not, that’s a that’s that makes sense. Now I read that magazine and I’m like, Oh yeah, that’s exactly what it is. That’s not my mission. Right? My mission.Isn’t what, like what major leaders need to know? My mission is an Entrepreneur is someone who makes things happen for themselves. And, and I’m going to show you how to do that. and, that’s, that’s my mission. And, and when I was at fast company, fast company, fast company has a different Editor in Chief.Now I don’t, I, I don’t, I don’t know how to speak to their mission. Now, when I worked there, it was really, it was like, how do we ha what’s next in business is kind of what it was like, what’s next in business. And so that meant that Entrepreneur or fast company was super interested in things that seemed like they were industry changes.If you were a small startup, you, you had some, you had something show for a different idea in a way that you were shifting an industry, fast company was interested in you because they were interested in what’s next in business. So, yeah, every publication has that. And I, and I realized that it’s easier to hear it, or somebody say it than it is to like spend time figuring it out.But if you just, if you just read a bunch and you’re always thinking, why did someone make this right? Like this exists. Somebody worked on it. A whole team of people worked on it. What, what were they thinking? You know, you can reverse engineer it pretty fast. It’s like, if, if you, if you’re watching, if you’re watching a TV and a Subaru ad comes on, you can figure out who Subaru’s targeting pretty fast.Right? Look, who’s in the car. Where is the ad shot? Well, you know, like what’s the, what’s the music in the ad, right? Like all of those things are signals that tell you Subaru sat down with their marketing team and they’re like, this is, these are the people that we’re targeting right now. Make an ad for that.You can see it. And the same is true with editorial. You can see who it’s for. You just have to think analytically about it.Nathan: [01:01:45] Yeah. And it’s good. I’m realizing that I, when I read all of these different publications, I think of the blend or the amalgamation of everything that I’ve read across publications, rather than drawing the lines of what I read in the same publication and then tying it to, okay, what do I know about the publication?What’s their mission statement. You know, what have I read in interviews with, you know, their editors or their founders. And, I’m realizing now that, yeah, it’d be, it’s maybe not easy, but it’s straightforward to deconstruct that and take your own notes and see, okay, this is the kind of story that they’re interested in.And then to look at my own life and business and say, okay, where does that match up? And instead of having one pitch that I’m like sending to everybody, then I, you know, tweak versions ofJason: [01:02:31] Sure.Nathan: [01:02:32] how it matches to these three publications.Jason: [01:02:35] Customize it customer, right. It’s it’s I like what you said there, right? It’s not, it’s not hard. It is time consuming. And this is, this is one of the reasons why people would hire a publicist is to not have to do that themselves. But. I mean, you know, most publicists are pretty bad at their jobs. Let’s just be honest.And so, you know, hiring a publicist is not, is not like an end run around this. I mean, they’re all great publicists out there. They’re great publicists out there. I have friends who are great publicists, but, but a lot of them are bad at their jobs. And, and, and that’s because they’re not doing this thing that I’m talking about either they’re not customizing, they’re not thinking about exactly how to target.And so the more that you either surround yourself with people who can do that work or do it yourself, the more you will increase your chances.Nathan: [01:03:22] Yeah, I like that. That’s, that’s probably a good place to wrap up. We’ve taken a bunch of your time. I’d love for you to just tell listeners where to go to subscribe to the newsletter, follow you on the podcast, all of those things.Jason: [01:03:35] Yeah. Sounds great. I know. Look at that. The word newsletter only came up once in his podcast. How’s that?Nathan: [01:03:40] It’s all tangentially related too.Jason: [01:03:42] That’s right. I’ll tell you three things, I guess, number one, if it wasn’t clear already, boy, would, I love you to listen to Build for Tomorrow.So go check that out. Build for Tomorrow, wherever you get podcasts. Number two newsletter. If you go to Jasonfeifer.com, that is my name turned into a URL, J A S O N F as in Frank, E I F as in Frank, E R.com, you will be prompted to sign up for a newsletter, but you could also go up to the top to click on free training where you’ll get this free audio course that I created about how to become more adaptable.And when you enter your email address to get that free course, what do you know? You will also be subscribed to my newsletter. Little trick, maybe you haven’t heard about that one. And then finally, I will say that I’m pretty active on social media, particularly on Instagram @heyfeifer.So you can follow me there and DM me. I respond to literally everybody’s DM. So if you’ve got a question, I’ll answer it.Nathan: [01:04:47] Sounds good. Well, thanks so much for coming on.Jason: [01:04:49] Thank you. This was so fun.

Veni Kunche runs Diversify Tech, a newsletter-based business all about helping people who are underrepresented break into the tech world. After working as a Software Engineer since 2003, her main goal now is to help make the tech industry inclusive.Veni’s got a really interesting business model: a mix of sponsorships and also a job board, taking advantage of the robust community that surrounds her newsletter.Nathan and Veni cover everything from how she transitioned from working in tech to starting her business. They dive deep into the mistakes companies make when seeking to hire a diverse team, and and what they can do differently.Veni also shares real numbers. Listen to the end to hear:• How much she’s making per month from her newsletter.• How her revenue has changed over the last year.• How the pandemic has affected her sign-ups.Links & Resources Black Tech Pipeline Techqueria Out in Tech Veni Kunche’s Links Diversify Tech Business & Ally Newsletter Personal site: veni.dev Twitter: @venikunche Episode TranscriptVeni: [00:00:00] Companies write job descriptions, they’re writing for mainly men in tech. Also they’re writing for younger people. Oh, we have ping pong. We have pool at our office. Those are the benefits. My community don’t even care about that. What they care about is focused on how the company will support them in their career.And so those are the signals that they’re looking for.Nathan: [00:00:26] Today’s interview is with Veni Kunche who runs a newsletter-based business called Diversify Tech, which is all about helping people who are underrepresented break into the tech world. She’s got a really interesting business model of a mix of sponsorships, a job board, which I think is a business model on newsletters that we don’t talk about enough when you have that community.There’s a great opportunity there. Anyway, it’s a great episode. We cover everything from how she got started, transitioning from tech to starting her newsletter. We dive deep into companies who are looking to hire a diverse team and mistakes they make and what they can do differently, how transparency really matters.So there’s a lot of good stuff in there. Towards the end of the podcast, she gets into sharing the exact numbers behind the business, how much she’s making per month, how that’s changed over the last year. I think you’re going to love it.Let’s dive in.Veni, welcome to the show.Veni: [00:01:16] Thank you so much for having me happy to be here.Nathan: [00:01:19] So I thought I’d just start. If you could tell listeners a little bit, what is Diversify Tech and, you know, at a high level, like what’s the business model behind it.Veni: [00:01:30] Yeah. So Diversify Tech is a curated newsletter, primary purpose is to connect people who are underrepresented in tech with career opportunities. So I share scholarships that are available, jobs, events that are happening, around the U.S. so the main purpose is to connect, people who are underrepresented, to these opportunities.The reason I started it is because when you’re underrepresented, when you’re in your workplace or in your college at college, or wherever you feel where you’re alone, and you don’t really have a network, of people like you. So I wanted to bring something where I could be that resource for people.Nathan: [00:02:19] Yeah, that makes sense. So when you were working as a software developer in tech was this an idea that you were thinking about for a long time and you’re like someone should make this, and then you realized that that someone was you, what was that? What was that leap?Veni: [00:02:37] So actually like, had no intention of starting something like this. It was, I actually just wanted to start a business. I didn’t know what that was. so I was a staff engineer for quite some time and I didn’t quite fit into the corporate world. I kept switching jobs a lot, so I was like one day I was like, you know what?I think I want to try something on my own. So I started exploring how does one start a business? How does one? And I, you know, I learned that, you know, it takes quite some time to figure out who your customers are, customer market fit, you know, all of that. And as I was learning, I was also volunteering for the women who code chapter in DC here.And, as I was volunteering, I connected with a lot of women in tech and that’s when I realized that there are a lot more, floods than I thought, and blah, and everybody was trying to find each other kind of, to feel connected and to kind of talk through this, you know, our issues. and I started doing just online office hours.So I was like for 30 minutes, I would just get on Google Hangouts and talk with people. And I got connected with so many people from across the U.S. just by offering that. And then that’s when I realized, okay, everybody’s. It’s facing similar issues and we’re all discussing the same thing over in Oregon.So I thought, Oh, why don’t I start a newsletter where I can reach more people. So prior to Diversify Tech, I started a newsletter called Code With Veni, and I was like, Oh, I’ll share what I’m learning. And I will also, you know, share what other women in tech are doing. and you know, it was more supposed to be like inspirational and, you know, that’s how it started.And after a year of running that I started getting requests for sponsorships. People want it to sponsor the newsletter. People wanted to post jobs. Uh that’s when it finally clicked that I was like, Oh, I’m starting trying to start a business. And I think I actually started, okay. So that’s what it is like, Oh, once I started getting, receiving his foundation of, so I was like, Oh, this could be my business.So that’s when I was like, then I kind of pivoted off of good with many. Cause I didn’t want the branding to be just me. So, and then I also wanted to include not just women, but everybody who’s underrepresented in tech. So that’s when I kind of like Diversify Tech from that. Nathan: [00:04:54] It’s always fascinating. How, when you build an audience, sometimes like the, the business model will just come, you know, or the business will just come and you’re like, I don’t know what it is. And then over time, someone’s like, Oh, could I do this? And you’re like, I mean, I guess so like, sure. Yeah.Let’s talk sponsorships. That’s a great idea. Let’s you know, and then I imagine people are like, great, can I sponsor with my job listing, you know, or something like that. I’m trying to get it in front of a more diverse community. And so it was that where like the job board came in,Veni: [00:05:25] Yes. As I started growing the newsletter sponsorships kind of, didn’t make it like, but sense because the demand was higher than I, because I send the newsletter every week, you know, I can’t have that many sponsors showing ads. So I was like, Oh, okay. Maybe I’ll start a job board itself. And I will include job ads in the newsletter plus also on the website.So that’s how the idea came. Nathan: [00:05:49] What was a moment in that process where you thought like, Oh, this could actually be, be the business that I’ve been trying to start.Veni: [00:05:58] Yeah. Yeah. I think that, you know, the first time was, you know, when I got my first sponsor, with coated venue, and it was what they were willing to pay me was much, much higher than I was expecting. I thought I would get like a hundred dollars or something. And I thought, and my first sponsor with all the whole package, they signed me up for like a three month contract.And I think they pay me like $10,000 for it. I was like, Holy cow, like, this is how much money one can make.Nathan: [00:06:28] How many subscribers did you have at the time?Veni: [00:06:30] At that time I heard about 1500 hoping.Nathan: [00:06:33] Yeah, so that’s a substantial sponsorship.Veni: [00:06:36] Yeah. Yeah. So that’s when it finally clicked that I was like, Oh, I can do this, turn this into a business. and then with diverse tech, when I started again, I started with smaller numbers.It took a while for the job board to gain traction. and because I think I was very strict in who I wanted as customers. and then after a year about running, I think it worked it spread through word of mouth. Cause I’d run the job board slightly differently compared to other job boards. I asked companies for like their demographics, you know, are you actually diverse right now?And also like, what are you doing exactly to, you know, diversify your company? What are you doing to include people? And so I have all of those questions, so it took some while to get traction, because I don’t think people wanted to share that information at the beginning. But as time went on, I think people realize the strength, the strength in like growing a diverse team and, and too word of mouth.The job board itself started growing. that’s man last year at the beginning of last year, I quit my job. I was like, okay, I think, I can do this, run this as a business. And I wanted to focus on growth and that’s when I quit my job last year and started working on the newsletter and the job board.Nathan: [00:08:00] Nice. I’m curious for that different angle that you took on. I guess asking each of the companies who want to post a job for like, okay, but what are you besides paying money to post a job? What effort are you actually putting in? What progress have you made so far? was that a hard decision, especially in the early days?Or was it something that you’re like, no, this is the way that, you know, diversified texts are actually create change.Veni: [00:08:28] Yeah. so it was, it was a hard decision in the sense that when I got my first few sponsors, what had happened was I was sponsored by a company, you know, on the surface, everything looked great. but then it turned and they did hire somebody from my community. And then a few months later, I found out that, this person, a women of color who was hired by this company was having a terrible experience of this, company.And that’s when I realized that, okay, I can just expand whoever, I need to do. because this had like a real life impact on somebody just because, you know, I chose to take them as a sponsor. And that’s when I was like, okay, this is like serious. I need to really need to figure out who I’m having as a sponsor.I think at the beginning, I didn’t realize. What that meant, you know, by taking somebody as a sponsor, by having somebody on the job board, I was giving a message that this is a safe place for people who are underrepresented in tech. so I didn’t quite understand that, but once after that situation happened, then that’s when I realized.So when I started oversupply tech on the job board, I was like, I have to make sure, you know, the sort of thing doesn’t happen. I mean, I can’t, I don’t have full control over it. Right. But I try my best not to have that situation happen again.Nathan: [00:09:56] Yeah, that, that’s interesting because you know anything from your newsletter that you link out to, or all of that people take it as some sort of an endorsement, whether, you know, it’s not, you necessarily signing on to endorse and love everything about that brand, but. Right. You have this trust and credibility and, your readers are like at once.You wouldn’t have linked to it, if it wasn’t good, which kind of puts you in a hard place because you don’t have necessarily enough information to make a full endorsement of a company. And so I liked the way that you’ve done it with, with systems like, for, you know, everyone listening. If you go to Diversify Tech.co and go to the job board, right.You call out specifically, that it’s remote, you know, the, the countries that, you know, the company’s hiring from the salary, and you know, a salary arrangement. So many people are just like, yeah, well, we’ll share the salary when we get to the final interview stage and you go through this whole thing.And you’re like, I was expecting a salary of 140,000, and now they’re offering 110 because maybe they, I think they can get away with it or, you know, whatever other things. Or, you know, as, as you’re applying for this company, I imagine people are like going to the about page and looking at a sea of a hundred or 200 faces and going, what team would I be joining?Am I going to be the only one? And so I love that you call it specifically. There’s three people on the, on the team, in this role. One is a person of color, you know, one is a woman, you know, and, and you’ve standardized that really well. So anyway, I am a huge fan.Are there things that you tried to standardize in, you know, in that listing that didn’t actually work, you know, information that you tried to provide up front that, you know, maybe you weren’t able toVeni: [00:11:48] I think at the beginning I was a bit, yeah. relaxed, in the sense that I made it, all of those fields, optional. so when I made that optional, I realized that people just weren’t sharing it. So that’s one thing I did is like I made the salary, required Field. I made, you know, the team members required Field.Don’t so things like that. And I also made, you know, ask them, you know, what, what are you doing in terms of making a change within your company? So all of that over time, I actually made them required. and when I did that, I thought I would get less and less customers, but it turns out actually I ended up getting more and more customers.And then also, people started sharing that information willingly, which built trust in the community, which means they, you know, spread the word out more. so it like worked out in both ways. so standardized in the way that I made, I am a little bit strict and like what I ask.Nathan: [00:12:48] I like that. It makes for a more unique community and a more unique product that, you know, that you’re putting out there because someone can scroll through that and you’re, you’re effectively saving them much time. Cause they were going to jump over to the about page and try to like piece together some of this information.And so you did it for them. So I like that. we’ll come back to the, the story of growing it and all of that, but we’ll, while we’re on the topic of. You know, actually, you know, diversity and tech and all that. I’m curious, what are some of those signals that, you know, job secrets from underrepresented minorities pick up on in the job postings and maybe on the other side, what are the things that, you look at when you see a listing?And you’re like, Oh no, what are you, what are you doing? You know? And then maybe some of the things that you really celebrate and say like, okay, this company is putting out a great effort.Veni: [00:13:41] Yeah. Yeah. I think, people who are represent underrepresented, they kind of want to know what they’re getting themselves into kind of, so that’s why I asked the demographics, because some people maybe they’re used to being the only person on the team and they’re fine being the only minority on the team, but they know that information upfront instead of, going through the whole interview process.And some people are very strictly, like, I will not work for a team that is not diverse, but so they get that information upfront. And, and in terms of, job descriptions, people do want to know kind of, I think traditionally when people and companies write job descriptions, they, I think they have, you know, they’re writing for mainly like, men in tech, specifically like men in tech and are like, they also might think they’re writing for a younger people.I don’t know. That’s what it seems like. You know, they like, Oh, we have ping pong, or we have a pool at our office, you know, that that’s, those are the benefits that they list. and like my community, like a lot of them just don’t even care about that. They don’t care if they have, you have food at the cafe, you know, at the office, or if you have, you know, if you do happy hours, like they don’t care about that stuff.What they care about is like, you know, well, how much paid time off, is material? How much maternity leave are you going to give? Are you going to support us in our career? Like, is there a stipend for learning, like a learning for coaching? so they’re more focused on, they’re trying to get a idea of like how the company will support them in their career.And, and as, as them as a person. So those are the signals that they’re looking for. And in the most generic job description, it’s very hard to tell, because they don’t give that information. So people have to go to the, as you were saying, like, well, page, see who was working there. and so, so I think that’s, I think people need to, companies need to shift their mindset from like, okay, we’re writing something and we’re trying to attract a much, much broader group and, you know, have to think about what they care about.Right. and, yeah. And, and the things are, sometimes the job description, again, targeted to men. So they might say he will be doing this, you know, they actually use, like the. Say something like that. Yeah. So they think that there are tools out there. There’s one tool called the gender decoder, I think, where you run, put the job description and then it’ll tell you if you’re using, feminine, coded words or like, like it does the job description, seem like it’s being written for like masculine, coded words.So things like that you can check through. But in general, I think it’s before writing the job description, governments really have to think about like, okay, we’re not writing how we used to. We need to change. And we need to think about who all or all the different kinds of people, that we’re writing for.Nathan: [00:16:51] Even calling, calling out things like, yeah. Time off opportunities, flexibility as parents, you know, those sorts of things versus talking about hustle and bean bag chairs and ping buying and you know, all of that.Veni: [00:17:10] Yeah. I forgot to mention, on top of that, as we were saying, you know, salary is very important to have to on the job I’ve been seeing more and more companies do that, which is awesome, because, depending on the look, the location and what people are shooting for, you know, that doesn’t fit, they can choose not to go through the whole interview process only to learn later that, you know, the salary doesn’t match them.And other things. I also, actually, I started asking companies like what, their interview processes, like, that’s been a big thing because my community has basically told me that if they do buy important reviews just don’t have them. So I actually made that again later. I was like, if your company does whiteboard, interviews, I’m sorry, we’re not a good fit cause nobody’s going to apply to it.So that’s been another thing to kind of share what kind of interviewing, that that companies are using because based on that interview process also can like, you know, make it exclusionary to second people. For example, I’ve never, ever done well on a whiteboard interview. I am somebody who cannot think.Right, like right on the spot. and somebody who has to think Passage that Ella tell over that answer. so that they are take-home makes sense. Who, which can be much long, which can take quite long for some people. And they can see other job board. If it’s it’s something that will take them hours, they’ll probably choose not to do it.You know, things like that. So for companies also have to think about like the interview process, what are they, who are they making it easy for and who they might be excluding?Nathan: [00:18:54] Yeah, I like that. I’m realizing the product that you’re providing, you know, both the companies and, you know, but especially to your community is really all about expectations and saying, I’m going to give you as much information as possible about this job opportunity upfront so that it can set your expectations.And so exactly as you’re saying of like, if you’re one of those people who is okay being, you know, the only one in a category on, on their team, you know, that upfront, you know, you know what the salary is upfront, you know, all of this. And, you know, I love that like hiring is such an opaque process like you and I, from our side, we try to make like, run our hiring processes as best we can, but even we’ll find times that, like we went through a whole bunch of candidates and we waited a week longer to send a letdown email to people that, you know, we weren’t going to move forward with then than we intended to or something like that.And so, just setting those expectations is huge. I’m curious on the hiring process, you know, or, or things that other companies are doing in that, like what makes for a great hiring process when startups asked you like, How should we, how should we improve? You know, what of the things that you point them to and make sure that they want to change so they can have more success.Veni: [00:20:19] Yeah. As, you know, as you were saying, I think transparency is one of the most important things because there’s a lot of stress and anxiety in world, when people are interviewing, and the ma the more of the company can be transparent about everything, like salary of the interviewing the timeline, when they’re going to hire all of that, you know, reduces that anxiety quite a bit for candidates.I think the other thing is I think a lot of people also want feedback too. If things didn’t work out, why it didn’t work out. I know it’s hard for, to give feedback for everything. but that’s something that our community asks for a lot. and, and one of the things that I, I hope companies move away from is kind of like the culture fit, injuries, sick.They do a lot of underrepresented people in tech. Think of culture, fit interviews as a way of basically, excluding people who are not like the founders or who are not like. Who are not like the managers. So that means a lot of my New, these will not be cultural fits for a lot of companies. If you think of it that way, or, you know, some companies think culture fit as something that’s values.Like maybe, the company has certain values. and, but nobody really knows. So every the interviewer, thinks one thing, the founder thinks one thing, the manager. So they all have different views of what, what culture fit actually means. So at all these different processes, they use their own version of culture fit, and there might be excluding people who are actually qualified.So I really hope like companies move away from that. because right now, a lot of underrepresented people think of culture fit and reuse as basically racist that they’re just excluding. if people who are not, who are not like the founders, I answered the Mo mostly those, and in terms of, diversity, one of the issues that has been coming up is companies try to put, they put a lot of effort in branding and marketing, rather than the actual process.Whenever somebody says, Hey, we do care about diversity. We want to do this. So they put all their effort in like Marketing. Like they want to seem like they are a good company. Which maybe they are, or maybe now, but they don’t actually go through the work of internally seeing our Day, you know, how, how they treat their employees.Is it, do the current employees like the company, do they feel okay sharing whatever’s on their mind? so they don’t do the internal review instead when they choose to, they, they go more outward, like, okay, we are, are we, that’s what they keep proclaiming the message. And sometimes when, you know what, some of us will believe it, and then we will go interview, we’ll get hired and then we’ll go.And then it’s like, Oh gosh, this is not what you said. you know, so I think companies also need to kind of look more internally before they try to recruit more candidates.Nathan: [00:23:51] Yeah. I mean, the process matters so much. And so I love spelling out the steps in the process and, and. An all of that. I’m curious, let’s see, just thinking about these companies and there’s so many of them that say like, okay, we’re going to, this is the way that I feel like company would talk because it’s the way that we stopped at different times of like, okay, as we hire for these eight roles, in 2021, we’re really going to work to increase the diversity of the team.What are some of the things that, especially from a company that’s not already diverse, you know, what are some of those things that they can immediately do to start to, move down that path and have like jobs that to be well received. And, and all that one thing that even you touched on a second ago is you can even spell it in your job listing.We will give feedback to every candidate who we interview. Maybe we’re not gonna, we can’t give feedback to every candidate who applies and maybe. But actually, I guess if you wanted to make your job listing stand out, you could offer to do that. And you might give feedback to 150 200 people or something.What are the, what are some of those other things that, companies can do when they’re really just starting that journey?Veni: [00:25:12] Yeah. I think for setting, making connections with communities, I know like some companies, you know, will have connections with the university of different types of universities. If they’re hiring for college grads or they’ll have connections with meetups or organizations. so similarly I think they should diversify that, you know, that’s a good way of like networking to CA with candidates.So there are like so many meetups communities, online, like there’s black tech pipeline, there’s tech, Korea. there is out in tech, there are so many organizations now. I think, you know, first step would be do, Connect with those communities and get to know them, and see what they’re are looking for, like what their candidates are looking for.And in terms of, the hiring process, I think recently I had somebody post a job and they had to immediately take it as two days later because they got so many job posting, so many applications. And one of the things they did was in there for the interview process, they said, Oh, we’re just going to have a casual conversation about what you had previously done, for your work.And candidates loved that because black people who have experienced, they are very, very tired of going through the same process that everybody is going through of like taking a coding test to go doing this. There’s like so much. And when you’re applying for jobs, it takes, it’s a lot of effort.Sometimes it becomes like your part-time full-time job just to apply and do all these take on exams. So one of the ways this company stood out was that, Oh, we’re going to review your previous experience to see if we’re a fit. so I think, you know, where to stand out is actually to make it easier for the candidates.I know it’s harder on the company side when you get, but I think if you know what you truly want, I think you can make your job description a little bit more transparent because if you list like 10 different things, candidates know that you’re not expecting them to know all the time, different things.So people from all of those. Different requirements will apply. So you’ll get a lot of applicants, but if you’re aware of strict and say, I want these things, and that’s actually what you want. I think it helps the candidate to know, okay, this am I a good fit or not? and also truly list, I guess the big problem with job descriptions is that no one actually knows what the job is based on the job description, because it’s just seems like you’re going to do everything.Which, which I know is that, is that the actual actually true? I think being strict on both sides, like, describing what actually you want and also interviewing for exactly that, Nathan: [00:28:01] Yeah. And so one thing that I hear in that is a level of transparency, like we talked about before, but also I’m saying that as a company you’re willing to take on some of that work, right? Because in a lot of interview processes, you know, the company is getting hundreds of applications, I think for a typical engineering role at ConvertKit we get between 200 and 300 applications.And so it’s very easy to fall into this habit of like, okay, we have really limited time. So how can we screen the candidates and put as much work on the candidates as possible? You know, so that it saves our time as a company. And so if you’re trying to stand out, what you’re talking about is like, no, we’ll actually take on more of that work.We’ll give resumes at detailed review it, we won’t put you through the same canned process of like, let me ask each person these same exact five questions and all of that. And instead you’ll jump on a call and be like, Hey, it’s great to meet you. You know, like be conversational, personable, and just be like, let me learn about you, you know, in a genuine conversation rather than like this sterile formal interview process.And it sounds like those are things that people would really like.Veni: [00:29:20] Yeah. Yes, I think so. I think everybody in part, part of a lot of, different communities and everybody’s so tired of just the interview process mainly, you know, they applied and also app applications and writing cover letter for each of them and uploading resumes. I mean, if they’re, you know, on the company side, you know, it might be that you’re getting, you know, 200 applicants, but on the candidate side, they might also be applying for that many jobs for, but for each job, they had to put an effort for the application, for the, you know, the resume, the cover letter.If there’s a take-home exam, if there’s a code test at the beginning, all of that, like really, really adds upNathan: [00:30:07] Later on in a hiring process, you know, if you’re doing a code test or a homework assignment or something like that, what are we doing? I ConvertKit is we do have that project. I think it’s capped at five hours and it’s, I’m trying to remember the exact details. I think it’s paid at $75 an hour, which is not like an incredible, you know, rate for anything like that.But we’re trying to demonstrate like, Hey, this is the time that you’re putting in. This is, Everything else. So I’m, I’m curious, is paying for the, you know, those homework assignments, something that is really well received by candidates.Veni: [00:30:48] Yes. Yes, definitely. I just got an email this morning from somebody saying that they went through an interview process and they didn’t know about it, but they did get, paid for the intro, the take home part. And she said that that was really nice of the company. So yes, that definitely helps if you do take home exams, and take home tests.And, another thing is when there are take-home tests, some companies are making it a little bit. Too much. Like sometimes some of these, they take like a whole week, to work on the project. So if you’re applying to a lot of job working on a take-home project for like that it’ll take four hours.That’s a lot, that’s a lot. So I’m glad that, you know, for ConvertKit it’s, you said five hours. So I think that’s like a reasonable time. And on top of that, if it’s paid, but there, yeah, I think companies need to be mindful of that too, because the candidates are applying to a lot of jobs and they can’t be spending all their time just doing a take home exams.Nathan: [00:31:50] Yeah, that makes sense. When they realized that we used to do at ConvertKit, that we don’t really do anymore. And I’m not sure why is we used to do a lot of like, contract to hire. And so, you know, we would find someone that was really good. And, then we’d say like, okay, we think we want to do this, but let’s do for 10 hours a week for the next three weeks or something.Well, they have their other role or, or something like that. Let’s do this actual project that we’re paying full rates for that is legitimately useful to us. But we’ll have been straight that like, we work well together, you know, as a candidate, you’re a good communicator you can deliver on the code and that kind of thing.I feel like that used to be a thing maybe three, four years ago in the industry. And now it, I don’t think it is at all anymore.Veni: [00:32:39] Yeah.Nathan: [00:32:39] take on thatVeni: [00:32:40] Yeah. I think that’s a hard one. and again, it’s the whole time aspect of it because people don’t want to quit their other job while they’re, so they’re still doing their other job and probably have, you know, if you’re a parent, you have, other things that you’re taking care of. So on top of that to do another, you know, contract work, I think that might be the main reason, for my community.At least that’ll be a hard one for them to do. More work on top of that of things. but in terms of assessment, I agree that is a good way to like, get to know the candidate and see if you fit. But I think it’s the time constraint. That might be the issue.Nathan: [00:33:17] As, you know, more and more people are being hired into tech. And, people trying to break into tech are in a better and better position. You know, it’s one of those things where, you know, a really talented candidate might have quite a few offers. And so if one of them has like this, yeah, we’d love to have you.And we’re just doing this contract project to make sure. And this other one is just like, we would love to have you, can you start, you know, then you’re like, ah, I think I’ll go with this one. Yeah. And so then just to be competitive, I mean, it’s sort of, I don’t know if this is a good analogy or not, but like I think about re you know, real estate markets in, like in Boise where I am, the real estate market is absolutely insane right now.And so it is a hundred percent in the buyers, or sorry, in the sellers favor right now, you know, and that’d be the same thing we’re in, in tech, the, the job market, it feels to me to be very in the candidates favor right now. Wow. Which is amazing. Cause then it’s going to bring in, you know, salaries, keep climbing and everything else.Veni: [00:34:21] Yeah. I’ve been seeing a lot of like really high salaries lately, which is good as well. I do want to add that it seems to be, candidates side, if you’re like more on the senior side though. Unfortunately for like entry levels and people who are trying to get into tech, it is highly competitive for them.There are, especially because companies just don’t seem to be hiring anybody on the entry level side. Which is, which makes it hard. And in, and in the past few years, you know, like bootcamps, all of these, like whole lot of people have generated lots of people who want to get into tech. but because there isn’t that much demand for entry level positions.Right now there’s ton of people who are still looking for their first job. So on the, you know, on the people who are trying to enter tech, it’s a, unfortunately it’s pretty hard for them. and for, people who aren’t represented, I know some people who’ve been looking for a job for like the past two, three years, and they still haven’t found a job.And when an entry-level posting does open up, it’s just like, they get so many job applications that they have to like close it off right away. Yeah. It’s hard. So it’s like, it depends on where you’re in your career. Like for the beginners is definitely hard for them right now.Nathan: [00:35:41] That’s interesting. and I, I’m thinking about the entry level positions that we’ve posted and you’re absolutely right. They have a three, four times the number of candidates that a mid-level or senior physician would have. How do you think companies should balance that? Right. Cause obviously the company is trying to, they have their goals.They’re trying to ship software on the schedule, but then at the same time, you know, building a diverse team, it’s not just in background and all of that. It’s also in skillset and level of, You know, how experienced is the team? What new perspectives are they bringing in and everything from there? how do you encourage companies to, to think about hiring entry-level to all the way up to senior and the mix that they have on their teams?Veni: [00:36:30] Yeah. I think, I think what’s happening right now is that most companies are hiring mostly like mid-level or senior. Like when I first started the job board, all the roles that I was getting were only senior roles. and my community was kept asking me for other roles and I’m like, you know, it was a hard position for me because that’s what companies were hiring for.And lately I’ve been, asking the companies, you know, please do share, you know, mix of, roles, not just senior roles. that seems to have helped a little bit. I definitely have more mid-level roles now. I think in term for the company itself, well, I’ll give you an example of in my previous company, I used to work for the us geological survey as a software engineer, and it was a pretty mixed group.Like I think we had at least, I think it was half and half. We had like five folks who were junior and rebel five folks who were senior. And we were pretty well. you know, we didn’t feel like we were, the juniors were taking that much, more of our time or anything like that. I think even there, I think it’s, when you set the expectations, I think, or the seniors that, you know, part of your job is to, you know, help the juniors and bring them along.It helped them along in their career. I think, and the way we worked, you know, we were able to meet our deadlines. everything worked fine. I think there is. one thing I do want to say is like tech is also like. Always changing. So I feel like people are newbies sometimes to you and the seniors are Sundays newbies in certain technologies.I know that people say, I want only a senior year, you know, developers or senior designers, but at the same time, they’re also new bees and they’re also continuously learning new things. So if you think about it from that way, you know, hiring a junior and helping them along, it is not that much different.I think I know companies, they might be looking at the bottom line too, but in terms of like diversifying, I think if you want to, you know, include more on grips and people, I think it has to be from all levels. so if you think of it that way, I think you become these do need to figure out how they can.Helped you in years. and, and so on. and also like every senior has to start as a junior, right. And I feel like the company that does help people who enter the market, they’ll be more loyal to them. For example, I was very, very loyal to the first company that I were hired me. I worked with them for two years.I went to grad school and the end a few years later actually went back to them as a senior engineer. And I worked with them because I knew it was a GAP company. And I had, you know, I felt like it sounds weird loyal to them because they were the ones who helped me break into the industry. right now, when everybody wants to hire seniors, while it’s hard, it’s very competitive.And they’re going to have to spend a lot of money into recruiting if they have to spend a lot of money for their salaries. but if, you know, if they spent all that effort and money on growing a junior, you know, they could, you know, And get somebody up to that level in a few years, you know that, but I feel like eventually the industry does need to hire at three levels, folks, because you’re not going to be able to get seniors all the time.Nathan: [00:40:11] Yeah. I mean, the industry just needs so many more, more people and you know, that news for the companies, you can’t keep just trading the same senior engineers that you have to actually grow the pool. cause we just, we need more software engineers. I’d love to shift back to, Diversify Tech and, and your business.Would you mind sharing some numbers as to, you know, where you’re at for subscribers and then, you know, any revenue numbers, anything like that, that you’re up for sharing?Veni: [00:40:43] So was FinTech. And so I started it in 2018. I was before I was looking up how many people I started with. So at that time, when I started, there were like 300 people in December when, July, 2018. That’s when I started, it was about 300 people. and since then, right now, we are at about 80, 8,600 subscribers, who, for the newsletter for underrepresented people in tech, and for revenue.When I started, there was no job board. I started the job board around. December of 2018. I was getting above $500 per month in revenue at that time. And it took some time to grow and in last year, and in 2019 it grew to about $1,500 per month. and at that time I wasn’t doing any marketing, it was all through word of mouth.So that’s when 2019 kept being consistent around 1500 to $2,000 per month. That’s when I was like, okay, I think I need to focus on it to grow it that I think I can make it bigger. That’s when I quit my job in 2020. and, unfortunately because of the pandemic, Asher did not have a chance to grow the.I didn’t have time to, but the effort into it. but fortunately word of mouth still continued. and in June of last year it actually had like double, quite like the revenue jumped up quite a bit. I started making about $10,000 per month of June of last year. and right now I’m averaging about $17,000 per month in revenue, this year.Nathan: [00:42:30] Yeah. That’s that’s fantastic.Veni: [00:42:32] Yeah. It’s, I’ve had a few spikes here and there. but that seems to be how it’s going now.Nathan: [00:42:39] And so is that, or how does that split? Because you have Patrion, you have the job board and you also have sponsorships, is most of that driven by the job board.Veni: [00:42:48] Yes, it’s about 80% of it is from the job board. and then sponsorships, I haven’t been taking as much lately, but sponsorships are about 10%. and Patrion, I actually didn’t include Patrion in the number of sessions, but, right now I get about a thousand dollars per month. And through patrons.Nathan: [00:43:10] Nice. So let’s say a solid baseline for, you know, expenses for running the newsletter and all that. Yeah. That’s good. What do you think about different ways to monetize a newsletter? You know, there there’s so many different people do paid newsletters, people do sponsorships, they sell products, everything else, you know, you’ve settled on your product, your main product being the job board, where there other monetization things that you’ve considered or, and I guess this makes it broad questions, but, just if someone’s coming to you and they’re like, Hey, I’m going to start a newsletter.You know, what would you say to them about…Veni: [00:43:48] Yeah. I think, you know, it totally depends on their audience and you know, what the topic is. I know a lot of, lots of newsletters that are similar to mine. They have, paid version of it or they have a community. So one is paid where version, and which gives them some extra bonus, Content or they have a separate community.And they charge for being part of the community and for extra perks, for me that didn’t quite. Fit with, my team and my audience, because one of the things I’m trying to do is, connect them with opportunities. And I don’t want to create any barriers for people. So that’s why I didn’t want to go the membership route or so I don’t actually charge my members for anything.The newsletter itself is free. So I, that was that’s part of the mission to, to help now to help them, you know, connect with them opportunities. So that’s why I didn’t do that. But whereas for me, it’s, mine’s kind of like a tomorrow cited marketplace. So have my users who are underrepresented in tech.And then, I have the customers who are trying to. You know, reach this audience. So that’s why for me, it made sense to go towards the other side of it. So companies who are trying to, you know, advertise, so initially sponsors ship is where we’re what I wanted to do. but it became a little bit tricky for my audience because sponsorship usually goes more towards branding and marketing.And I didn’t know if that’s what I wanted to do. I wanted companies who are actually doing the work versus who want to make it seem like do it in the work and it becomes very tricky. so that’s why I’ve been reducing sponsorships a little bit, because I have to do a little bit more digging and I can always find information I need.So job boards, it’s more like the companies are themselves applying to be on the job board. so I made it a little bit more. Strict. So that’s how the job board, I feel like it goes in theme, but my audience, so for me, the job board has been working out, and also do ads. so other ideas to just do any kind of ad, in the newsletter.So I do have ads, like, you know, sometimes bootcamps want to share that they’re opening up applications or there is a, event that is looking for more speakers from a diverse group. So they’ll share their call for proposal and they’ll do an ad. so, so yeah, those are the different, the things I’ve been doing is, you know, the job board, some sponsorships, some ads, and for other folks, you know, depending on their audience, like paid memberships, Smith, I’ve been seeing a lot of folks doing paid and newsletters and then, the communities, yeah, It’s pretty cool.Like when I started, there were barely any newsletters now it’s just like, there’s so much going on and it’s cool to see what other different things that people are doing.Nathan: [00:47:00] Yeah. Well, one thing that I really like, I love about what you said is the mission driving the business model, because you’re absolutely right. That you can have. There’s a lot of different groups involved, right? There’s the candidates, it’s the members of the community. There’s companies who are hiring there’s the bootcamps and all of this.And you could try to build a business model where you’re making a bit of money from each group. But when you’re saying like, no, I’m trying to, my whole mission is to get underrepresented people in tech. And so there can’t be any barriers on that side. Over here, you have all of these companies that have initiatives.some like you called out are purely Marketing and others are real genuine efforts to, build a diverse team. Then it’s like, great. Let’s, let’s find a way that they can fund the business that they can pay for it because. You know, they’re the ones who are going to be paying out large salaries and everything else.They have the budget for it. So from a mission sides, have them pay for it. And that’s perfect. I love that. I think for a lot of, newsletter creators and just business owners, you know, when you’re looking at all these different opportunities and trying to decide, Oh, should I go this way or that way? And it’s like, what matches the mission?And let the mission be the thing that, that decides the business model.That’s good. what’s working for, for growth, you know, you mentioned, you know, you’re approaching 10,000 subscribers on the newsletter. where are those subscribers coming from now? And, and, you know, what are some of those other things that, that are working to bring in new subscribers?Veni: [00:48:34] Yeah, I’m all of it has been through word of mouth, which has been amazing. it’s been mainly word of mouth and some of, and some of it through Twitter. So I guess word of mouth on Twitter has been the largest largest way. we have been getting subscribers and I’ve been trying to think of more ways to kind of grow it, to kind of increase the growth rate a little bit.I haven’t found anything particular yet, but right now I’m trying out a different program because word of mouth is what is working. So I want to do and make it easier for people to share and refer more folks. So that’s what I’ve been working on now. and for, I’ve been also getting requests to kind of make the newsletter for more groups.So, so I’ve been getting, folks from Europe, like a lot of companies from Europe want to share. things on the job board, but I didn’t, I didn’t grow that part of the community. All of our members are in the U.S. so, we’re actually launching our newsletter for the Europe region, Europe and UK region, in a few weeks.So that’s another way I’m, growing the newsletter and the job board, yeah, depending on how that goes, you know, maybe cover more regions, around the world. Yeah. That’s, that’s what I’ve been doing now.Nathan: [00:49:59] Do you have a team or is this all you what’s? What’s the process behind the scenes?Veni: [00:50:04] Yeah. when I started, it was all me, I have somebody who, have a contractor who helps me with some of the data and stuff. like all of them. Things I collect, she helps me, you know, put them into our database and that they show up in the newsletter on the website. So I have somebody that, and for the Europe, one had the, I didn’t want to take that up on my own.So where the Europe one, I’m working with somebody who I, I, I partner with somebody who she’s going to be running, the Europe newsletter. So right now it was just the three of us.Nathan: [00:50:37] Yeah, it’s I mean, it’s amazing what you can get done with a small team. And then it’s also amazing how much, you know, an additional human coming in to help makes a big difference. I wanted to ask on, on the affiliate program, or the referral program, a lot of people are thinking about doing that right now.You know, it. I think on one hand it feels like something that like, Oh, you could spin this up and growth could accelerate by, you know, 10, 20% a month or something. And then on the other hand, you get into the logistics of like, okay, what do I offer as rewards? how is this actually going to work? Well, people share.And I’m curious what that process has been like and just how you chose the rewards that you did.Veni: [00:51:15] Yeah. it’s going back to how you were saying, you know, I tried to try tie everything to my mission. So one thing I’ve been doing is so hard to pick her words for their whole program. W what I’ve been doing is picking, products written by people who are underrepresented in tech. So the first few divorce were books, written by women of color.Or, and next, I think I’m going to do, like maybe stickers that were made by women of color are t-shirts made by other, people who are underrepresented in tech. so those are the rewards that I’ve chosen. I like that because I feel like I’m supporting their business, which, which is what my mission is to support other under-represented people in tech.So, and then also, hopefully it’ll help, with the growth with the newsletter too. yeah.Nathan: [00:52:06] Yeah. So let’s talking platforms for a second. what, what are you using to put together the referral program and how’s that been working?Veni: [00:52:15] The first, when I started, I actually built my own. but it, it was, it was still beer. I was like, I should, I was like, I should not be spending my time doing this. and then actually I’m using spike loop, which is integrated into kind of red kid bread. So, so that’s what I’ve been using now. yeah, it’s, it’s a, I’m just trying, I just started it like about three months ago.So I have still have to figure out, you know, what kind of words will work, how, I need to optimize all my subscriber forums and all of that to, to get better results.Nathan: [00:52:52] Yeah, well, it’s, it’s always fun to the test and experiment and figure that out. I’m at the point where I think I’ll launch a referral program for my newsletter in the next month, two months, you know, kind of one of those when I get around to, but I have those notes where you’re like penciling in ideas.You’re like, Oh, this could be a reward. And then you’re like, Oh, that would be a terrible reward. It’s not new that, so it’s good. And of course they’ll also be using easing spark loop just because it’s so integrated and, and the team over there is great. What are some of the things that, are next for the newsletter in the community?You know?Veni: [00:53:31] Right now I’m well I’m waiting for the pandemic, and vaccine and all of that, because it’s been hard to manage everything since it’s, it’s all of this started. my intention when I quit my job was to grow the community and the New newsletter on the job board. fortunately the job board has been growing, through word of mouth.The subscriber rate, for the newsletter has reduced a little bit. So I’m trying to increase that. So I’m focusing on that now. yeah. I’m taking it slow, I guess I just I’m happy that things are working, trying to enjoy it for now. and I think one of the next things we’re we, me and Nyamata, she’s been, she’s going to be working on the Europe newsletter and so, for a, that, and he probably in the next two weeks, and it’ll be interesting to see what that market is like.It’s kind of cool to be in a position to, launch something when you already have an existing the center groin. That’s a completely different problem than when you’re just starting out. So, so yeah, that’ll be fun.Nathan: [00:54:41] Yeah, you’re spot on with that, that having an audience and a following and, and connections in the industry, then when you go to launch that next thing, it’s still a ton of work to be clear, but it is you get that, that kickstart, to it. And so that makes a big difference. also I love the angle that, you know, you hadn’t, you were just talking about of like enjoying the process and saying like, I always think about this trade-off as, as a founder, you know, as an ambitious person, between gratitude and ambition and how do you live in both of those places at the same time and this feeling of like, I have enough.And I’m so grateful for the company, the community, the team, like everything that I have, like, this is incredible. I get to, You know, I’m not working for another company. I get to do my own thing. And then also, like, I’m always trying to grow it too, to be bigger. And I think it’s hard to live in both those places.It sounds like, you’re doing a job with that. I’m curious if you have more thoughts, if that’s something you struggle with as well,Veni: [00:55:51] No, I definitely struggled with that, but one of the reasons I did start my own business was to have that, so that I took, I tried to remind myself of like, okay, the reason you quit corporate. And it was because you wanted more time on your hands. So sometimes I have to like live by myself out of bed, otherwise, otherwise, you know, it’ll be the same world where I’ll be just working all the time and not enjoying life.So one of the reasons to start a business was to have that flexibility. So, or remind myself to take the time. and the other thing is that with COVID and everything, life has been very, very stressful, like so many unknowns, all of that. So I definitely feel a little burnt out on that sense, like from the life side of it, you know, being a parent, now with everything that’s going on is definitely hard right now.So that’s another thing I’m like, okay, it’s not. I definitely need a break from all of it. So I just, you know, but can’t exactly take a break. so that’s why I’m trying to be a little bit more, like go at a slower pace.Nathan: [00:56:56] Yeah. Yeah. That’s exactly. That’s great that realizing that you can set your own pace and do that. I’m curious, you know, I’m thinking back to when I was working at my last startup job and, you know, we were doing many of the things that started doing, I don’t know, we’ve pulled all nighters. Like what, what was even the point of that?You know, I’m just looking back and that was eight years ago now, but there were so many things, when I wanted to leave that job that I was looking to like, Oh, what. I could travel. I could, you know, have freedom in my time, you know, w even things I do now, like going for a walk in the middle of the day is just like, it’s amazing, but I’m curious, what’s something recent that, you’ve kind of celebrated in your life of like, wait, because I don’t work in corporate anymore.I was able to do this, even if it was small.Veni: [00:57:50] You know, there wasn’t a fender. Like I would totally just go take a vacation. but lately I’ve been just, like we’ve been enjoying, enjoying little things. Like my husband works from home too. Like we’ve been taking walks and lunch, or, you know, one day we just kept her, my daughter goes to daycare one day.We just decided to keep our daughter at home and we did nothing besides hang out. so yeah, things like that.Nathan: [00:58:18] Well, I think that’s such a good reminder that. Even in all of the growth and hustle and everything else that we do for our own businesses, realizing that like, okay, take a step back. Remember from her why you decided to be your own boss. You know, that’s funny.I actually think about if you would write your own job listing, you know, for a diversified tech, you know, you’re like now hiring a CEO and all of that or whatever role you’re like, wait, would I be a good boss? Am I do I treat myself? You know, well, or am I like now you have to be hard driving and get all of this done.So that, it’s just a good reminder that as a founder, as an entrepreneur, like you are the boss and like treat yourself well, treat your employees. Well, even when that key employees, you. well, thanks so much for coming on. I’ve I’ve loved this conversation and learning more about the inside of your business and, and, and especially thank you for sharing everything about, you know, how to build diverse teams and mistakes that people make.Why don’t you tell people where they should go to follow you online, subscribe to the newsletter support rate, what you’re doing and all of that.Veni: [00:59:34] Yeah. I’m on Twitter a lot. I’m at @venikunche. That’s my handle. And for the newsletter, if you go to DiversifyTech.co, you’ll see a Subscribe button and you can sign up for it. So if you’re in groups and in tech, you can sign up for one of those newsletters. I also have one for companies and for allies who want to understand diversity more.So that one’s called Business & Ally Newsletter. So you can sign up for that one too.Nathan: [01:00:01] That’s perfect. Well, thanks so much for coming on and we’ll see you around on Twitter.Veni: [01:00:06] Sounds great. Thank you so much for having me.

Venture capitalist Li Jin left Andreessen Horowitz to start her own firm, Atelier Ventures. She started Atelier to fund a specific vision of the world: a world in which people are able to do what they love for a living and to have a more fulfilling and purposeful life.In addition to being an investor, Li is a prolific writer and podcaster, producing not only a newsletter but also writing articles for major publications.Find out whether you should really be writing content every week, or whether your effort is better spent on longer-form, epic articles. Should you be publishing in your newsletter, or in publications like Harvard Business Review?Li and Nathan don’t just talk about content, they also get deep into business models for your newsletter business, with Li sharing her perspective as the founder of a venture fund. Don’t miss Li’s unique combination of deep investment knowledge and artistic creativity!Links & Resources Andreessen Horowitz - Software Is Eating the World LiveJournal: Discover global communities of bloggers who share your unique passions and interests. Myspace Zynga The Nathan Barry Show 028: Packy McCormick – How Much Are 30,000 Subscribers Worth? Evernote Harvard Business Review - Ideas and Advice for Leaders The Nathan Barry Show 023: Tiago Forte – Building a Second Brain & Lessons From a $1M/yr Newsletter The Nathan Barry Show 017: David Perell – Mastering Twitter to Grow Your Newsletter and Make Money Li Jin’s Links Newsletter: Li’s Newsletter Website: Atelier Ventures Podcast: Means of Creation Twitter: @ljin18 LinkedIn: Li Jin Episode TranscriptLi Jin: [00:00:00] What are your goals and what is the content that you’re creating and why are people subscribed and reading it? The business model needs to fit what your content is, who the audience is, who the creator is, what the platform is. All of those things need to be aligned. Direct user monetization is totally in vogue in the form of donations, ad hoc payments, subscription payments.It’s always charging the user for something. Nathan: [00:00:28] Today’s episode is with venture capitalist Li Jin. So Li was at Andreessen Horowitz, and then she recently left to start her own firm, Atelier Ventures. We talked about a lot of things that I find interesting, like business models for your newsletter, for example, should you monetize through a paid newsletter sponsorships or what she does through running a venture fund?We get into whether you should write content, you know, consistently every week, or should you publish it once a quarter and put out these incredible long form posts we get into writing about, or excuse me, writing for publications like Harvard Business Review versus your own newsletter. There’s so much good stuff in here.So I’ll just get out of the way and we’ll dive right in.Li, welcome to the show.Li Jin: [00:01:14] Thank you. Thanks so much for having me, Nathan.Nathan: [00:01:17] Okay. So I want to dive in and just immediately talk about revenue models, all of that, because you have this tweet that I just loved, that it was like dying, laughing when I saw it. And the gist of it is I have a paid newsletter. It’s my monthly LP update. You were talking about how either those business models is everything else.And I imagine saying like me, why don’t you launch a paid newsletter? So could you talk through how you think about, you know, your business and what you meant with that week?Li Jin: [00:01:50] Yes. So I joke that my LP update, which I send out quarterly as a email is basically my paid newsletter. And I think it’s, it’s basically a riff on the joke that we used to make about a16z, which is the firm that I used to work at the VC firm that I used to work at. We used to joke that it was a media company that monetized through venture capital because a 16, Z as a firm is so prolific in creating content.They have a podcast, actually, a network of podcasts, the blog. they have a series of different clubhouse shows now as well. they just do a ton of different media and content creation activities. And so people used to joke like, Oh, this is actually a media company that happens to monetize through venture capital.And I think of myself now as kind of a miniature version of that, where I’m a solo. Content creator. and I monetize through venture capital. Like that is my revenue model. I have a venture capital fund that I raised last year, called . And that is, you know, my day job. That’s where I spend the majority of my time.And then the content that I put out into the world, It’s free. It’s, it’s mostly free for founders to consume. It’s really designed to help them build companies, and to guide them and their strategies. And I don’t monetize the content at all. And the way that I monetize the content is through investing in the best companies that come as a result of the content creation.So, yeah, that was, that was the Genesis behind, the tweet. And so the LV newsletter, I mean, the LPs are like the investors in the fund and that’s how I monetize it.Nathan: [00:03:33] Yep. That makes sense. And I think once you have this attention, Then there’s so many ways that you can monetize it. I was talking with Trey, remember who wasn’t a past episode. we were talking about how people have alluded to Nike being like they’re just an ad agency who happens to realize that the best model to monetize is through, you know, shoe and apparel sales, but really their core strength is advertising and marketing.And so I think there’s plenty of examples of people who have, like, the. Have this audience and then an unconventional way of earning a living.Li Jin: [00:04:09] Yeah, precisely. And I think to build on that. Like there’s a lot of examples of newsletter writers who do a similar thing where they’re operating a syndicate. Like I think Packy who you’ve had on the show has a syndicate that he invests in deals through. there’s other newsletter writers. I know that angel and fast Lenny Rachitsky is a very active angel investor too.So yeah, a lot of them are sort of blending different business models because newsletters are such a great vehicle to, to build an audience. To get reader attention, to communicate your thoughts into the world and kind of mind-meld with a lot of really interesting folks. And then the best way to monetize that might not be through a straight up subscription or pay.Well, it might be having upside in the businesses that they built. and I think. Content creators are having that realization too in the broader content creation ecosystem beyond just newsletters. So now I’m seeing content creators from the Tech-Talk Instagram, YouTube worlds, getting into investing angel, investing into startups, because that is a way that they can monetize the brands and the attention that they’ve built and also diversify themselves beyond just being a single content creator.Nathan: [00:05:28] Yeah. I mean, it’s, it’s wild when you see it. Like, I think. You know, a lot of people in the, the acting movie world have, are doing it now, but like Ashton Kutcher was pretty early with startup investing and, you know, he’s taking this money and fame and attention that he has and putting it into to startups.And you know, now it feels like everyone’s got, you know, some sort of started that they’re involved in or a liquor brand or something else where they’re basically saying, saying like, yes, in addition to. Getting paid millions of dollars to show up in this movie or to sponsor this brand on TED talk or, you know, like do a sponsored spot for the brand new talk.You know, why don’t I have equity? And I’m curious where you see that going. Do you think that trend is just going to continue?Li Jin: [00:06:15] Yeah, I think in any crowded market with a plethora of different options that folks can choose from brand is going to matter brand as a differentiator matters. and so. Like venture capital is no different from that. There’s so much capital available right now for founders. Founders probably get like a ton of inbound offers to give them capital.And so founders are now in a position of being able to choose, like who do I actually want to accept capital from? and I think I first heard this from first round capital. one of the partners there said like something like. venture capital is a product that you buy with your company’s equity.And so yes, as a founder, you’re choosing which product to buy with your equity, your equity is worth something you can purchase like a venture capital investor to work with through that equity. And so, the implication for VCs is like, how do I, how do we make our product the most attractive product and how do we distinguish ourselves and be the, the venture capital provider of choice for founders. And this was actually one of the driving factors behind me announcing my fund a couple of weeks ago on product hunt was tapping into this ethos of actually investors are products. We are building products. We have to provide differentiated value to founders just as they are trying to build differentiated startups, to compete in a crowded landscape of different software.So I think content creators, getting into investing is just another it’s emblematic of this. It’s like, how do, how do we differentiate our capital from all the other capital that’s available out there? And especially in the consumer world when consumer attention is now so scarce and spread so thin across so many different options, having.Captive consumer attention and having distribution into consumers, it’s such a huge leg-up for any consumer company and content creators represent that they represent so much built-in distribution power into, tons of different consumers. And so I hear from founders all the time, like they want to bring in content creators into the round, and they sometimes have specific criteria of like content creators who have a big following among, you know, Gen Z on TikTok or, um, moms on TikTok if they’re selling some sort of children’s education products.So they’re identifying like who are the end consumers I’m trying to reach and what are the con who are the content creators that can help me reach those, those people.Nathan: [00:08:58] And are they in those cases they’re taking, It’s not a straight advisor deal in that case. Right. It’s there, it’s still taking investment from the influencer or from the fine and then saying, but really the money is just the table stakes. Now it’s like to differentiate, what else are you going to provide as far as access to the audience or whatever else is that right?Li Jin: [00:09:21] Yeah, the way that it’s structured is, it, it, there’s no like, one single way that it’s structured. It can be sometimes just an advisory agreement, that we’re all used to, or it could be a combination of advisory. Plus like investment to the company and with dollars. or sometimes it’s just, you know, a normal equity investment into the company.I think founders usually for, that the Creek is an investor into the business because then they have more skin in the game. but you’re right. That like, it’s more about having access to their distribution and their brand than the actual dollar amount itself.Nathan: [00:10:01] That makes sense. Were you always thinking about, like as you left a16z starting your own fund, or as you started a new newsletter and all of those things, did you pursue kind of all that rate, like the whole range of options for how you could monetize.Li Jin: [00:10:16] the, the plan was always to start a fund. So I knew that going in. I mean, again, I guess, going out that was always the plan and, Aye. But in tandem to that, I also kept creating content, which was an activity that I had been doing when I was at a16z. And even before, like I I’ve always been very active in writing online and writing publicly.A lot of people don’t know this, but I kept a food blog throughout college, where I would Chronicle like all of the meals and things that I would cook. and before that I was blogging about like my everyday life. Very boring, in high school and in middle school. So I’ve always been a very prolific writer.And so, as I’ve been on this journey of, building my own fund and, and getting started investing, I’ve just continued to create content and primarily written content because that is the format that I feel most comfortable in.Nathan: [00:11:23] Yeah, that makes sense. I think a lot of people, you know, you have this like overnight success type of story, and then you dig back and it’s like, yes, but I’ve been creating content consistently for. I don’t know, a decade or two.Li Jin: [00:11:39] Yeah, I I’ve been writing Daily. Like I first started writing Daily. I remember this moment. Very clearly. I moved to the US when I was six years old from Beijing. And before that, I didn’t know English. So I learned English in first grade through ESL classes, and I happened to win a diary, a physical diary.It was a Lisa Frank diary, like multicolored, rainbows, plus dolphins on the cover. I won that at an afterschool bingo game in the first grade at the same time that I was learning English. And I started writing in this diary every single day. as a six year old and throughout my childhood, I just went through so many different physical diaries, like I wrote consistently every day and then the internet happened and I went onto the blogging platforms.But yeah, writing has like been a consistent daily habit for over 20 years.Nathan: [00:12:38] Yeah, that’s wild. What was the first blogging platform that you went on to was that LiveJournal or my space?Li Jin: [00:12:43] I think it was Zynga.Nathan: [00:12:45] Yeah, I didn’t, I published on LiveJournal, butLi Jin: [00:12:49] I was on LiveJournal to you. LiveJournal was great. LiveJournal was what I used in high school. It was where all the cool kids were.Nathan: [00:12:56] yeah. I’m trying to think what happened to LiveJournal. I actually hadn’t thought about LiveJournal before this moment. Didn’t.Li Jin: [00:13:03] I, you know, I tried to dig up my old LiveJournal and all of my old things, and I think it’s been deleted like after some period of inactivity, I think they just deleted everything. So it can’t find it so that like, it represents years of memories, which I’m quite sad about. So I think there’s still value in keeping a physical diary.If you want to remember your life.Nathan: [00:13:27] I think there’s things that on one hand like that I’ve published on LiveJournal that I would love to have. But I’m also very thankful that the broader internet isLi Jin: [00:13:37] Right. Yes. It, it was very like it’s, it’s doc’s proof basically because they deleted everything on our behalf.Nathan: [00:13:45] Well, maybe taking a step back. I think there’s a lot of people who have built a newsletter in are trying to decide. The best way to monetize it. and haven’t thought about investing, or maybe they’re thinking about like, Oh, maybe they like me right now. Right? Because of my Content, I get asked to invest in a few things.And so I do a little bit of angel investing, but I’m curious what advice you have for someone who is now going, Oh, I have 10, 20, 30,000 people on an email list. they’re starting to be this deal flow. You know, is starting a syndicate or maybe even becoming a full-time investor of direction with resilience.Li Jin: [00:14:32] so I think you really have to consider, like, what are, what are your goals and what is the content that you’re creating and why are people subscribed and reading it? Like, I think the business model needs to fit all of those things. So I talk about the concept of like, business model fit, like the business model needs to fit, like what your content is, who the audience is, who the creator is, what the platform is, all of those things need to be aligned.So I think right now is a moment in which like, Direct user monetization is totally in vogue and every platform is introducing new direct user monetization features, typically in the form of like donations, ad hoc payments, subscription payments. but it’s always charging the user for something. And I, I actually don’t think that that fits every writer.There are actually lots of different business models that you could play with and experiment depending on who your audience is and what the content type is. like I think Packy is very successful doing sponsorships and like if he moved to subscriptions like that would block access for a lot of people that he’s able to reach.Right now through sponsorships. I think there can even be like new business models that get invented that we haven’t even seen yet. That could be really well aligned with writers. so for instance, there’s a platform called mirror, mirror.xyz. Is the name like a reflection mirror. and it’s a crypto blogging platform.So they’re built on crypto rails and you, so you can program all sorts of different new business models that previously hadn’t existed. So recently there was a really interesting experiment that a blogger, named John Palmer ran where he actually crowdfunded his, his essay, his upcoming essay. And so, people were able to.Place bids and crowdfund his essay. And he ended up raising $13,000, but the people who were crowdfunding it didn’t just do it. So out of altruism, they did. So in exchange for tokens that they could then trade and that represented ownership in the essay itself. Which is really interesting. so that’s like a new business model that gets unlocked by crypto, which previously hadn’t existed.So, so I’m interested to see more of these experiments happen in the future that aren’t, you know, one size fits all because I think the subscription business model is really great for writers who are writing consistently, who are delivering consistent kind of constant value to their audience, but it doesn’t work for everyone.Nathan: [00:17:11] Yeah, that that makes sense. And like, in this case, if you were to. Not publish for a few weeks. That would be entirely. That would be totally fine because your business model isn’t dependent on that extent or like continuous value.Li Jin: [00:17:24] Exactly. Yeah. I think the issue right now is like, For writers who write a really high quality piece, maybe two or three times a year. There’s no good viable way for them to monetize that. Like, they can’t really justify a subscription. Maybe they couldn’t collect donations, but like that just depends on people feeling very generous and charitable.And so the only good way to monetize that kind of cadence of writing right now is like through investing, I think, through being a venture investor, But yeah, like I think that type of writing also deserves a good business model.Nathan: [00:18:03] Makes sense. I think the biggest point for someone listening in is that there’s the business models that you see at face value of like sponsorships, or, you know, paid subscription access probably are the two most common. And then it’s also like, and there’s so many more possibilities and I’m always the most fascinated by the businesses where you’re like, wait, I know they make money, but how do they make money?And when you really think about it often there’s some other, you know, side thing, like for example, I know the people over at link fire and they provide these like little landing pages when for artists, you know, so Taylor Swift comes out with her new single here’s a single page that has all of the links right.To. iTunes, Spotify, et cetera. You know, they’re used by all the major labels and you go to their site and they make money through subscriptions. You’ve paid 15, $20 a month to use their service, but they actually make a lot of money through the affiliate revenue from iTunes and Spotify, and for all that for driving the traffic.And so, you know, just really encouraging people to dig under the surface a little bit and, and at least consider some of the less obvious business models.Li Jin: [00:19:15] Yeah, absolutely.Nathan: [00:19:19] I think that, well, I want to shift gears a little bit. There’s, an article that you wrote, titled the creator economy needs a middle-class I’m curious one, let’s start on the research side. That is like a, a there’s like quick blog posts that you can write. You know, you have an idea, you write it out, you fire it off.And sometimes they really resonate. Other times they don’t, And, you know, maybe it’s like three hours or five or 10 hours that goes into that. this post is the opposite of that. And I’m curious, what is your research process look like? How do you go about writing a substantial piece like that?Li Jin: [00:19:56] Yeah, I would definitely say like, all of the writing that I have published is not of that sort it’s of the like a hundred hours went into this, or like, that’s why I only published like four times a year. it’s because I work on each piece for like two, three months. So, yeah, a lot of research goes into these things.There’s a lot of time I speak to a ton of people. I have a ton of people read them, critique them, offer different angles and perspectives. and so, yeah, I, it takes a really long time. It’s like writing a thesis in school. how this one came together was. So I had written a piece like a year and a half ago called the passion economy and the future of work when I was still working at Andreessen Horowitz.It’s a blog post that was. I think pretty widely read and a lot of founders, were really positive about it. But one of the critiques that I got in the aftermath of the publishing that piece was, this is great. And like so optimistic and like very positive. And we really want to have this come true, but it feels like, it feels like this is only a viable, viable path for so few people like.There’s only so few people who can even make a living this way and who can participate and be successful in the passion economy. like, is this too optimistic? Was there feedback? And that question has been like in my mind ever since then, like, because as an investor, I want to back things that touch millions of people like that can, you know, transform society and how we work, not just enable a thousand people or 10,000 people in order.To to monetize. so I’ve always been really interested in like, how do we actually unlock the ability for many, many more people, like tens of millions, hundreds of millions, of people to be able to participate in the passionate economy and to be able to do what they love for a living. So the piece was inspired by that.And, in order to write this, I had to go very broad initially and like study, how did the middle-class come about in the real world? Like I looked at. The history of this country and like how, we got started in the trends around inequality in the middle class, in all developing countries and, and.Developed countries, Europe, the US et cetera. I looked at like policies. I researched specific policies that we had passed in order to encourage the growth of the middle class. And that contributed to like rising wages in the middle of the 20th century. I looked at unionization, deregulation, the trends like since the 1970s and the shareholder revolution, like so much research went into this.And it was very like concisely summarized in the end piece and piece really focused on the crater economy. And how does the crater economy, support and middle, but yeah, there was, there was a ton of background research that went into it and it was informed by stuff in the broader world as well.Nathan: [00:23:09] Lot of questions about that, the first one is what’s the reason. That you take the approach of say like for flagship pieces of content a year versus maybe some of the more traditional advice of like publish super consistently, you know, every Monday at 10:00 AM or something like that.Li Jin: [00:23:28] I mean, I kind of do that because I use Twitter. And so Twitter is like my kind of ongoing, I Write tweet storms. And like, these are just my quick thoughts. It’s nothing like super groundbreaking, but it’s like interesting and thought provoking. And like, I’ll just publish that on Twitter. for my long form pieces.I don’t know, that’s just kind of the bar that I hold myself to. And like, I think things are more evergreen when they go really deep and when they are extremely cohesive and pull in so many different strings and like just give rise to so many more questions and lines of thinking. and that’s the type of style that I think.I, I prefer to write in, and I feel good about my content when I publish it. there’s a lot of like stuff that I don’t publish that never sees the light of day. That is perhaps of the sort that like I could quickly publish if I wanted to be more frequent in my writing. But I just don’t think that they’re groundbreaking enough.Like my bar is kind of like, does this get people to see the world in a completely different way? You can’t do that so often, like it’s hard to do that regularly, every single all week. but that’s kind of just the bar that I’ve given myself as a writer, because I want my pieces to have longevity. I want it to be like, every time I’m in someone’s inbox, they feel like they must like clear their calendar and feed this thing.And in order to. Maintain that relationship with my audience. Everything has to be really good.Nathan: [00:25:06] Yeah. I definitely, I have a few pieces that I’ve written that. Are sort of that those flagship pieces of content, like for me, it’d be the ladders of wealth creation and then the billion dollar creator where, you know, they really, they come together over a long period of time. It’s usually like it started 18 months ago with a conversation with a friend that kind of sparked something and then it sort of iterates from there.But I can’t get any consistency towards those ideas, you know, it’s definitely when they come in and they, you know, I shaped them for a long time. So I’m curious. Do you maintain a list of like these ideas that might turn into something or what’s, what’s sort of the notes process on that side?Li Jin: [00:25:50] I do the notes process is really disorganized. So it exists like in my brain, I have a list in my brain of things that I’d like to write. Sometimes that list gets dumped into Evernote, but not really consistently. sometimes I’ll think of something like really late at night when I’m not in front of my computer.I’ll just like, jot it down in my phone or like text myself. so the ideas are kind of scattered around, but they’re there, they’re there somewhere. And. Sometimes I catalyzed by either like an external thing or something internal that I read. and that just inspires me so much. I feel like, okay, now is the time to take that idea into like, actually.Build a piece around it and, and, and write it out, that there’s like way more ideas that I have that never turned into one of those flagship pieces and only a small percentage of them actually get written out. I actually think like for everyone, who’s saying like there’s too much writing in the world, like there’s too many newsletters.I actually think there’s like way more ideas that should be written out that currently aren’t just because writers don’t really have the time to do it.Nathan: [00:27:02] What I love that of the. The bar that you’re setting for one of these flagship pieces being like you should finish reading it and your worldview should be different, or you should at least have all of these questions about your current worldview.Li Jin: [00:27:15] Yeah, it changes someone’s life.Nathan: [00:27:24] What do you think about, you know, where are you published these pieces? Right. Because a lot of people would say has to be on my site. I need the, The search rankings, the backlinks and all of that. And you’re going like, no, I’m going to publish it on the Harvard Business Review.Li Jin: [00:27:41] Yeah. I, I, I’ve been sort of like, I’ve evolved in my thinking around this. well, so firstly, like when I was still working at Andreessen, everything had to go on their blog. So, I published on their blog and so a lot of my older pieces are still at dot com. since then I’ve been utilizing my own newsletter, my Substack newsletter as mine primary channel. and I like that because I think the ethos of having like access to your readership and being able to reach them directly without any sort of intermediary, I think that’s great. especially since like the way that I typically reach people is through Twitter and through this algorithm, like that feels a little shaky and unsteady.And so if I can collect people’s emails, that’s awesome. and then. HBR HBR came about in like the most random of ways, honestly. I hadn’t been intending to publish it at HBR. I was intending to just go through my newsletter as normal. And then at the last minute, basically when the piece was already done, I sent it to an HBR editor that I knew, and I was like, Hey, what do you think of this?And, and his response was, this is great. I would love to publish it. So can you hold your newsletter? and, and I, I basically, I was like, okay, like, let’s test this out. Cause I think HBR, like HBR is one of those publications that I would be willing to bend on my, like, Collect user emails rule. Like they have huge distribution, they have way more page views than my newsletter gets.And so I thought it was, it was a worthwhile experiment to run. And so, yeah, I gave them that piece. I also publish it in my newsletter that same day as well. but I I’ve been driving traffic to the HBR version and, you know, the response to, to that has been so interesting, because. When people read the piece in HBR, I think they just immediately viewed it as more legitimate than when I published in my own newsletter.People were like, Yeah. People were like, Oh, this piece must be so good. It’s an HBR. And I was like, have you read any of my past writing? Are you saying it’s not good? Like, cause it’s, it’s the same bar as I always have had for myself. It’s just that this one happened to get picked up by HBR. It’s like, my, all of my writing is like best, but like for some reason, because it’s an HBR, I think a lot of people just viewed it differently, which has been absolutely fascinating.And it kind of throws a wrench in the whole creator economy, narrative, right? Because we’re all about institutions over individuals and how like a personal brand is so much more powerful than like an institutional brand. But I firsthand experience that when I’m affiliated with this like powerful institution of Harvard Business Review people to take me more seriously, or at least there is a segment of people who took me more seriously.Nathan: [00:30:47] Well, I think it’s what you’re talking. I think about brand being the most important thing. And, you know, HBR has this brand, you even, you walked through the airport and it’s like, HBR has top reads all of this stuff. And so we know that the content is going to be really high quality and, and the packaging does matter, right?The packaging of the being an HBR versus, being on your blog or a newsletter Substack, like. And you’re just immediately in that of that caliber. And so it’s interesting. I’m curious if you think more authors are going to be pushing them to publish their content, you know, there, the Atlantic, you know, some of these other like publications that sort of have an increased amount of credibilityLi Jin: [00:31:32] I think they should. I think they should. Just as we kind of diversify our different revenue, streams and business models as creators, I think we should also diversify where we publish content. in order to expand our reach. It’s, it’s sort of like the idea of, Content collabs that we do with other creators.Like how do we leverage each other’s audiences in order to grow? I think, writers can accomplish the same by. Distributing elsewhere and tapping into an established publications audience. so I think if there is a publication that writers really admire that they think. Could be, harnessed for audience growth, where that publication probably has a large base of users who would also be interested in your writing.I think it’s definitely worthwhile to do that. I don’t think it needs to be done constantly and like exclusively. I don’t really believe in doing anything like all like the same all the time. but I think here and there, like writers can choose to leverage other platforms for growth.Nathan: [00:32:42] What were some of the results that you got from it? Was there anything unexpected or, Li Jin: [00:32:46] So the one unexpected thing was like people who I thought already really liked my writing were like, wow, this is so good. Like.That was one thing. like my brand, although I thought it was like already a legitimate, it was clearly not as legit as HBR’s Franz. I, yeah, I did get incremental new subscribers from it because my, my publication was linked at the bottom. I think it also, it, it was an interesting experiment for them.Cause I think their reader base is not as Silicon Valley centric as probably our information diet. Like we are reading all these blogs and like all of these sub stocks constantly and thinking about like the creator economy, I think a lot of their readers probably saw it and thought like, what is a creator?Like what is, what is the CR what is the greater economy? so I’m not entirely sure if like, My target audience mapped to theirs. there were definitely some comments of like, this is so abstract and like out there, and like first we need to define what a creator is. so that was really interesting.Cause I think. I think HBR is one of those publications that has such a broad reach across the planet. Like there’s middle managers in Europe and in the middle East who are reading HBR and might not be as like deep in this particular particular topic. Whereas our motion as newsletter writers is to go really deep and to be really aligned with this particular niche and not write for the public audience, but to write for like our specific single target audience.So going to, A more general readership target, targeted publication. it kind of taught me that I am kind of like inhabiting this little bubble.Nathan: [00:34:44] Well, one thing I was just thinking about is that you kind of have two different, demographics that you’re serving right. On one hand, you have the, the companies that you want to invest in, right? So if they’re reading your newsletter and someone’s thinking about, okay, I’m ready to raise then.They’re already a fan of you. And so your, your capital to come in has a significant advantage over any other VC fund, but then you have the other side of, you need to go raise from LPs. And so I’m wondering if being in a place like the Harvard Business Review or something else, or other places you might put your Content might actually help attract, new LPs.Li Jin: [00:35:24] What’s really interesting is that I’ve found that to not be true, like LPs don’t go on Twitter by and large, and they don’t read some stock newsletters that are written by practitioners by and large. And so. It was, it was really interesting, honestly, in a ton of my conversations with traditional LPs, they didn’t know where to create our whys.They didn’t know what the passionate economy was. They like never visited, you know, the blog, the a16z blog, like all of these concepts they had never heard of. And like, they. Never saw my Twitter. Like they, they might not even have a Twitter account. and so they’re, they’re kind of like inhabiting their own ecosystem and I’m not entirely sure, like what I need to write or like what topics I need to cover to reach them.I would say like among founders, like the stuff that I write does have an audience and like is widely read, but the LP stuff, like the Content has given me no advance.Nathan: [00:36:25] That’s interesting. Cause like I have this ideal that maybe it would give an advantage, butLi Jin: [00:36:32] I would love that, but that’s not the case.Nathan: [00:36:36] And raised from LPs, is it, you know, just a lot of introductions and meetings and that’s the whole thing,Li Jin: [00:36:43] It’s a lot of relationships, introductions, warm instructions, getting your LPs to introduce each more LPs. It’s such a, yeah, it’s a really fascinating like opaque worlds. None of them publicize themselves. You don’t know who they are, how much they invest, what they’re interested in. They’re not like on Twitter broadcasting that they’re actively investing.They’re very private about it a lot of times. so it’s yeah, it, it, it’s, it’s a whole separate universe. It’s actually really, really fascinating.Nathan: [00:37:13] Yeah, well, I’ve been at, this is going back to the side of running a venture fund, but what have been some of the hardest aspects of it?Li Jin: [00:37:21] Everything.Nathan: [00:37:25] It’s not, you know, VCs, don’t just kick back and, you know, like Write random pieces and live an easy life. It’s actually challenging.Li Jin: [00:37:34] Yeah, the, the thing pieces are definitely part of, but that is done like middle of the nights and weekends and on Christmas day, like that’s when I do my writing. And then during the day, it’s like a ton of pitch meetings, founders meeting with portfolio companies. It’s, it’s just this constant onslaught of like everything that you need to do constantly.No everything about it, husband. Like a really interesting exercise and I’ve, I’ve been going through it for the first time of year, because this is my first fund. Like I used to work at a firm that had 200 people. And so I didn’t have exposure to all of the different elements of running a VC fund. I didn’t, I didn’t use to have to fundraise.I never had to talk to LPs. I never had to, there were like teams internally that. Supported portfolio companies after the investment team decided to invest. And so that was also less a part of my job before and now I have to do literally everything. so yeah, everything has been challenging. Like fundraising was challenging.Keeping on top of all of the deal flow has, is, is like immensely. This huge, it’s a huge time commitment. then making time to support your portfolio companies. Is this other big, like. Pocket of, where we spend our time and then, and then just like a company as well. We never stopped thinking about fundraising and like the future fundraises, I thought it was like, you raised the fund.You could just like, go deploy the fund. And then someday in the future, distantly, like you you’re like, Oh, I have to raise another fund. I’ll go do that. But it never ends actually. It’s just like having a startup, like we it’s like you close fund one. Then at that time, a ton of people are like, Oh, you have a fund.Like, let me invest in you. And then you have to like, keep them warm. So the second fund, and then like you close that. And then the third fund, like you never stopped thinking about that side, which is, yeah, it takes up a ton of like mental resources. In addition to like the core Day job of deciding where to put capital.Nathan: [00:39:43] Yeah. So for anyone listening in who is currently a founder has been considering being a VC regresses. In fact, not greener.Li Jin: [00:39:53] Well, I think the grass, I don’t know, the grass may be a little bit greener because if you’re able to raise the fund, you have like this built in revenue stream for the next 10 years, which is nice. and you don’t have to deal with like, All of the, like the scale of the people issues that you have to deal with is not the same as like scaling a huge organization.But it’s definitely not a walk in the park.Nathan: [00:40:19] Yeah. I believe that, I mean, just a little bit of, we were talking a little bit before we started recording a little bit of angel investing that I’ve done thinking about like eight or nine, investments. And even then I’ve been like mediating things between founders and stuff like that. And there’s just wherever you turn in, in the wonderful world of business there’s issues to deal.Li Jin: [00:40:41] Yeah, exactly. There’s, there’s no easy jobs unless you’ve like inherited something. I think.Nathan: [00:40:48] Another interesting thing that you’ve been doing, that I’d love to talk about is your course on building for the creator economy. what, what sparks, why to create the course and, and hasn’t been going so far.Li Jin: [00:41:00] Yeah, absolutely. So the backstory is. Well, two things. One is like, I’ve been asked to write a book, create a course, like do more Content by basically everyone. Everyone is constantly asking me to like, write more, publish more like synthesize my thoughts more. And I’ve always been kind of pushing back on that, like, I don’t have the time to write a book right now or teach a course or like, you know, build more content.But like I knew that the demand was there. And then coupled with that, I invested, end of last year into a new platform that Goggin Biani and West cow co-founded it still does not yet have a name named TBD, so we shall call it. And what’s this new company. So I invested in going in with this new company, which is a platform to help experts.Builds and offer cohort-based courses. And so, when I was chatting with them about the company and the idea and the fundraise and everything, we were brainstorming about how it could be really good for me to be one of their initial instructors. And, you know, there’s this initial instructor batch on their platform actually has all sorts from their cap table.Like me, Lenny saw hell pump, we’re all investors in this company. And so. It’s kind of like where we’re, co-creating the platform with them and, you know, flagging issues as they come and really, helping them to realize like here are the opportunities to build better products. and so that was how the course came about.It was the combination of both, this platform making it much easier for me and taking a lot of work off my plate in terms of the logistics and everything behind the scenes of. Creating this course. plus the fact that like I knew that there was market pool for it, and the creator economy is such a huge area of interest right now.But I felt like there wasn’t a really good cohesive, sequenced, like package of information that was all like very carefully curated and packaged together into something really useful for founders. So I decided to build it myself.Nathan: [00:43:14] It’s, it’s been fun to see all the cohort based courses come together and, and, you know, Yeah, it was basically on his name is terrible. He’s been on the podcast before Tiago Forte, Tiago done with, Building a Second Brain. And, it’s just amazing to see in David Perell as well, right. With the two of them together with Write of Passage. it’s been amazing to see the different business model and it’d be like, So much more effective than even everyone was doing three years ago or five years ago of like, here’s all the videos you go through it, you know, maybe it’s a $300 price point, but most people drop off or something.And so in this case, you’re seeing a thousand dollar price point or 2000, or I think I just have one that somebody launched it, you know, it’s a $5,000 for the course and it’s starting to really feel like, Oh, this is an in-depth. Uh, it’s like a serious college class, you know, whereLi Jin: [00:44:17] Yeah.Nathan: [00:44:18] Everybody else and, and everything.Li Jin: [00:44:20] And I think people are, it’s really interesting. The variation in prices, right? Because a newsletter is basically priced at. A hundred dollars per year, roughly that’s probably the average price point of a newsletter, like $10 a month, a hundred per year. The typical CBC is priced at like a thousand dollars.So 10 times the yearly revenue that you’re getting from a newsletter subscriber. And so over the course of a year, are you communicating just as much content as the course provides? Probably. And so what does that Delta, what does that 10 X Delta representing? I think it’s representing. Accountability, like accountability of actually getting through the content rather than just getting access to the content and not going through it.I think it’s community, of like light like-minded peers who are going through the content in the course with you, who also enhance the learning experience. And then I think it’s the direct line of access to the expert, the course instructor who’s. Whose brain that you’re tapping into in a very direct way, versus like having, like reading a newsletter by them, it just feels a little bit more, impersonal and less direct. And so I think that’s what the GAP in prices represent, but it is really interesting to see. Especially firsthand now that I have this course, and I’ve also been, co-writing a paid newsletter with the guys at the, everything, every bundle, just to see like the huge chasm in price points, like there’s.Just huge variance in price points and how profitable each activity is. And, yeah, I think we’ll see more people start to have our cohort based courses. And I, I hope that like more creators realize that this is an option. I would caveat that it is like a ton of work to create a cohort based course.Like I’ve probably put. A hundred hours into the content development for this thing. Like, I didn’t have a Christmas last year because I was building out slides and doing research for this. so it, it is a lot of work, but it’s pretty high ROI.Nathan: [00:46:34] Yeah. Well, I like what you said about. Making 10 X the, I guess it’d be the ARPU, the average revenue per user, you know, a thousand dollar course versus a a hundred dollars a year subscription because one of them, you have to show up 52 times a year with high quality Content. And then the other one, you have to do a whole ton of prep work.But you can. You know, you can reuse that you can run the course multiple times a year or multiple years. and then you probably like, as you’re in the middle of this now, you know, you’re, you’re dedicated. It probably is your primary life. in addition to it’s your other full-time job as youLi Jin: [00:47:15] Yeah. Yeah. When you run the course, that basically is all consuming of your life and in the weeks leading up to it, it’s pretty intense as well. Whereas I think writing a piece of content, you kind of do it on your own schedule. If you get busy, it’s like, Oh, I’ll just do it next weekend. I’ll write it next weekend.You can’t like delay the chorus because it’s on everyone’s calendar and there’s a start date to it. And that. You know, you’ve accepted student’s payment, you have to deliver the course. And so there, there’s also accountability for the instructor to, to create all of the content in a way that doesn’t really exist for a passive subscription.Nathan: [00:47:54] right. How’d you think about the price point on it? What did you debate price that you settled on?Li Jin: [00:47:58] 1250. Yes. It’s 1250. I, it was determined in conjunction with, Gargan and Wess company team. They should really find a name. And I think, it was, I mean, it felt premium. Cause I think all of the other courses that they’ve run so far were less than that. but like it felt fair because, For a few reasons. One is like, there’s a ton of original content that I haven’t talked about written about. Like it’s, it’s brand new from my brain.Like these are students who are accessing it for the first time out of like any people on earth. So that’s pretty special. secondly I think it has real business value to people like it, it, the Content has the ability to really shape company strategies and to like inform the products that they’re working on at the time.And that they’re building. And so what is the ROI, if you’re able to make a better business decision than you were before, like that’s really high ROI. so the price point ultimately felt fair to us. I was a little bit nervous about it. Like, are people willing to pay this much, especially since I’m already pretty prolific in terms of, podcasting and writing and to my surprise, it was like wildly, wildly oversubscribed. And honestly, I think we could have probably charged more, but I don’t, you know, I don’t want to go too high, especially for the founders that I’m targeting. I think there’s also opportunity to like better price discriminate in the course world. Like for founders, I would love to offer a discount or have them be sponsored or something versus for investors and VCs who want to take my course, like I want to Jack up the price because they could probably pay anything.Nathan: [00:49:48] That’s interesting. If, if, if you said, you know, the price for the course is $2,500. but if you’re an early stage founder, you know, apply here, we want to make sure that you’re serious. You’re all of that. but apply here and you can take it for a thousand dollars or something like that.Li Jin: [00:50:04] And that’s what schools do. That’s what universities do through financial aid, through need-based financial aid is they perfectly price discriminate every single student based on their capacity to pay. We just don’t think of it that way.Nathan: [00:50:16] Right. Oh, that’s fascinating. How does the course fit into the rest of your business model of, you know, how do you think about how it intersects with the investing and everything else?Li Jin: [00:50:28] Yeah. I think if it has like, hopefully a really great way for me to build relationships at scale, with a bunch of really high quality founders and to tangibly provide value to them, such that I become their investor of choice. So it definitely has that intersection with my day job. but beyond that at a broader level, beyond just the relationships that I’m forming with my students who represent a ton of early stage founders, I think it also has been this amazing opportunity for me to crystallize my thinking and to put down a lot of thoughts that have been swirling in my mind, but like we’re kind of disorganized honestly, and, and weren’t structured in any sort of cohesive way and it helps me.Crystallize and sharpen my own thinking such that I’m able to better like guide my existing portfolio companies or better able to offer value to the companies that pitch me.Nathan: [00:51:18] I like that. Okay. Last question. On the, on the course side, you had the application side, right? When someone, they can’t just come and buy it, you have to goLi Jin: [00:51:27] Correct. There was an application process.Nathan: [00:51:29] How did that play out? And what was the reasoning behind it?Li Jin: [00:51:31] So the application process was because we wanted to cap the course. We want it to cap the course at a number that felt kind of still intimate and it wouldn’t be like, 10,000 students in the course live learning from me. so it ended up, so right now the course is 150 students. So we reached like the hard cap, and we got way more than 150 applications.And so we had to unfortunately turn people away and. You know, tell them to stay tuned for the second cohort. timing TVG. So the reason why there was an application is because for a cohort based course, you need to have constraints on capacity because like people are paying for your attention and your time and access to you.And that access can’t be scaled, infinitely.Nathan: [00:52:23] That makes sense. I imagine it would also play a role in conversion rates as well, because as someone fills out an application, they’re probably getting more invested and then there’s, there’s next between that. And when they actually have to pay, and then there’s also this feeling of like, Oh, you got accepted in.Okay, now I shouldLi Jin: [00:52:41] Yeah.Nathan: [00:52:42] Pay and right. There’s the accountability side of it. Okay. Now I should follow it through and actually make it happen.Li Jin: [00:52:47] It was, yeah, there was such interesting things that happened that I learned throughout this application process. One is, well, the application was actually kind of involved. Like they had to put in a lot of information. And so I thought like, Okay, well, we’ll probably get really high conversion off the application.Like if you went through this form, this type form, like you’re probably in, but that wasn’t the case. Not everyone actually confirmed after the application. So there was a bit of drop-off like, I think every time you add a step there’s drop-off, and then, what was the other thing I was going to say?The other thing was like, every time there was a milestone or a checkpoint to get through, like the application from application to like. Conversion or acceptance to conversion. Like people shared those moments on social people, screenshotted their emails. And they were like, I got accepted into this course and I was like, this is mind-boggling that like, you’re basically tweeting about like paying a content creator.And like, and, and like celebrating that, like usually people don’t celebrate giving a content creator money for something like that’s pretty rare, or like it’s even rare that people tweet about like buying a product. But like for this course, I don’t know. It, it it’s like college admissions people. It is a milestone.And so it became a milestone. Like we created a milestone for people and it continues to this day because the course is happening right now. People are tweeting about like just finished workshop one. And it was, you know, it was awesome here. All of the things that I learned, like everything has become like a milestone and it’s, it’s honestly incredible to see.Nathan: [00:54:29] Yeah, that’s amazing. Well, we should leave it there. I love the chat for a long time, but where should people go to follow you and learn more about the fund and subscribe to your newsletter?Li Jin: [00:54:39] Yeah. So the fund website is atelierventures.co. My personal newsletter is li.substack.com. People can also follow me on Twitter, that’s probably my most active content sharing channel. I’m @ljin18 on Twitter and yeah, I think that’s about it. Thanks so much for doing this.Nathan: [00:54:59] All right, thanks. I’ll see you later.Li Jin: [00:55:01] All right. Take care.

Mario Gabriele is the founder of The Generalist. His mission? To bring the most interesting tech writing to your inbox, every week. And he’s not doing it alone, either: Mario works with a team of contributors to deliver new ideas from some of the most original minds in venture capital and tech.In this episode, Mario talks about how and why he left a career in venture investing to build The Generalist, and his lifelong obsessions with writing and technology. The Generalist is not only a really successful newsletter, it’s a thriving business, too! Tune in to hear how Mario did it.You’ll learn about approaching and collaborating with the people you only dream of working with. Mario talks about how he went from merely admiring certain writers’ work to joining their “club” in 18 months!Mario also shares the most reliable way to advance your career, and the safest ways to accelerate it. There’s a lot of good stuff in this conversation!Links & Resources Stratechery by Ben Thompson – On the business, strategy, and impact of technology. Exponential View by Azeem Azhar The Nathan Barry Show 028: Packy McCormick – How Much Are 30,000 Subscribers Worth? Acquired Podcast Atonement by Ian McEwan Norwegian Wood by Haruki Murakami All-In with Chamath, Jason, Sacks & Friedberg Webflow: The no code platform for web design and development Pico - Signup and payment tools for the internet’s most passionate communities alexdanco.com – subscribe weekly at danco.substack.com Mario Gabriele’s Links Personal site: The Generalist Twitter: @mariodgabriele Episode TranscriptMario: [00:00:00] I just really love writing very, very much. And so, as soon as I got the width that like, maybe I could make this a real thing, then suddenly like a flip switched in me where I was like, all right, I have to go as hard as possible and feel like the value was accruing directly to me. As soon as I was like fully on my own thing, I suddenly felt like, Oh man, I’m unchanged to go after this. Nathan: [00:00:30] In this episode, I talked to Mario Gabriele. Now Mario runs an email newsletter called The Generalist, which is focused on tech venture capital and investing. He comes from the venture capital world himself, and then he really brings forward all of that into the newsletter. A couple of things really impressed me about Mario. One, he really collaborates, well, he’s got something called the S–1 Club, which is where they do tear downs of filings that companies make before they go public. And he really brings in other creators and they write them together. He also has something called RFS, which is Request for Startups and he brings in other venture capitalists and operators and everyone else to share startup ideas.So he’s got this interesting mix of his own Content, Community Content, and he’s built it not only into a really successful newsletter, but also a thriving business. So it’s a lot of good stuff. Let’s dive in.Mario. Thanks for coming on the show.Mario: [00:01:25] Thanks for having me, Nathan.Nathan: [00:01:26] Okay, so you have this line. I think you said it on Twitter and a few other places that I just want to start with. You said, it sounds ridiculous to announce your dream is to build a great newsletter and then you go into like, you know, but that’s what I’m doing, you know, my love of technology and writing and everything else. So maybe just start with why, like, why did you want to start a newsletter?Mario: [00:01:52] Yeah. I mean, honestly it wasn’t, something that was necessarily in the back of my mind for a long time, it really sort of happened organically. and I think work is often like this where for a long time, you’re not really sure exactly what you’re doing. And then. When you sort of find something that actually feels incredibly right, you can sort of trace back all the little things along the way that brought you there.And so for me, that was really two main, explorations. One was that, you know, from a very young age, I’ve always really enjoyed writing. and so I did a lot of that in school. and then after I’d left university, I started to take night school classes and fiction writing at NYU. Starting in 2012, I started to like write a novel every morning, getting up early, you know, spending an hour before work, just sort of like practicing, practicing, practicing.And it was just sort of this hobby I had. And then simultaneously where I was really building a career was in technology. so. You know, on the operating side, at a few companies and then on the investing side in sort of a few venture firms and, starting The Generalist really was just a way to.You know, I express that hobby in a slightly different way. I had folks be like, all right, cool. You’re spending all this time writing. Like what, why don’t you write a thing or two about, about your actual work? and so just started as sort of a side project on the weekends and then bit by bit, it just was absorbing more of my thought.More of my excitement, more of my energy. And it started to really feel like it was pulling me in this direction. And, once I felt like it might be possible for writing to become. My life’s work and be a viable career, which had always been sort of the reason I hadn’t tried to go full-time as a novelist.You know, even though, you know, unless you’re JK rallying, it’s pretty impossible. newsletters felt like a way I could do that and really write the stuff I wanted to write, and make, make a living out of it. Hopefully.Nathan: [00:04:09] Yeah. So, it’s, we’re recording this in February, 2021. When was it that you started The Generalist?Mario: [00:04:16] So I start, I wrote the first ever post in August of 2019. And honestly was sort of an accident that I started it as a newsletter. I had just been seen seeing people like switch over to Substack over Medium. This is before I had heard the gospel of ConvertKit. So, yeah, I was just like, cool.I’ll do this instead of Medium, like whatever. and then. That first post, even though it was very small circulation just led to so many interesting conversations and people started to sign up. And so it suddenly became like very clear why you should make it a newsletter versus a blog. and then I would say the other sort of critical point was in August of the following year. I went full-time on it. And the growth since, since then has been like significantly different, I would say, just like being able to put more time into it.Nathan: [00:05:15] Yeah. So, there’s a few things that I want to dig into there, but, I think there’s all these creators that we look up to and admire, right? The newsletters that we read, that YouTube channels that we follow, all of that, and there’s sort of this. Feeling of maybe otherness, we’re the person watching it.And they’re the, you know, the famous person creating the content, whether it’s the Casey Neistat or the Ben Thompson or, or whoever. And I’m curious who were a few of those first, like newsletters that you were reading where you’re like, Oh, maybe, maybe I want to be like that.Mario: [00:05:48] Yeah, definitely. Ben Thompson was like the first person I saw doing this in where I was like, is this, this guy’s job? Like he’s obscenely smart. And it seems like he’s doing well. but I didn’t realize you could do that. so, so he was really one of the first and then. Azeem Azhar writes something called Exponential View.I don’t actually know if it’s his full-time job. Cause I think he’s also a venture investor, but, it’s certainly a business. and so that was another one where I was like, yeah, this is a brilliant tech commentator who seems to have it as part of his career stack. And it just felt like, you know, the very least it was going to be a massive advantage to any traditional career I wanted to do.And, you know, hopefully the, the way to build a career.Nathan: [00:06:41] Was there any feeling of moving from? So from my perspective, you’ve moved from that, like the consumer, who’s just, you know, reading these tech news letters to someone who’s. Part of the clubs, right. if you’ve got all these other newsletter creators who are sharing your work as a great example, you come up in conversation like, Oh, talking PARA who I was talking to.It was Jason from Pico and I, and a few other people chatting. And there’s like, everyone’s just like, Oh, we love Mario’s stuff. Right. Has, has that been a shift for you? Or like, is there anything pricing in that shift of going from the consumer to like part of the creator clubs?Mario: [00:07:20] For sure. Yeah. I always, it always feels like a little bit of a trip. Like for example, last night, on Twitter spaces, me Packy McCormick, and of Not Boring and the two hosts of Acquired, David Rosenthal and Ben Gilbert. I’ve been listened to Acquired for a long time. I think it’s an amazing podcast and Packy and I sort of have come up at a similar time.And I remember talking with Packy about it offline. And I was like, man, isn’t this a trip that like, we get to jam with these two guys that a year ago or 18 months ago, we were just like really admiring their work. and I think that the real takeaways for me are just that like, One, the Content can really speak for itself as long as you are putting in a ton of work and, being really, really, really consistent about it.And that just like can accelerate you way faster than you might’ve imagined. I think, I constantly underestimated what I might be able to achieve alone as a solo creator. Both in terms of like, you know, traditional growth and just in terms of like being a part of these conversations.Nathan: [00:08:33] Yeah. I mean, that was exactly it for me, you know, and this is back in probably 20, 2012, 2013 of you just go from all the people that you read in mire. And then, you know, at some point you realize like, Oh, I’m, I’m part of the group. How did that happen? And it really, it, I mean, it just comes from that. There’s not this huge gap between the person consuming the content, the person creating it.It’s not like the creators, this legend or anything like that. It’s just like, Hey, just showed up and, and made stuff. And it works really well. Yeah. something else that I was thinking about is you mentioned like your career, you know, so working in, in tech and then getting into venture, and then as you start the newsletter, right?There’s a couple of different paths. There’s a lot of venture capitalists who have newsletters and, you know, drive incredible deal flow. So like that’s one path. It doesn’t sound like that was your primary path. You’re like looking to. You know, leave venture and, you know, be a full-time, newsletter creator.But one thing that I, that I was thinking about is there’s probably no faster way to accelerate your career than to go create an online presence. Go create a newsletter and teach and everything, because maybe you could just speak to this, like the amount of time it would take to move up through venture versus like, short-cutting that entire process by building your own audience.Mario: [00:10:05] A hundred percent and it’s sort of frustrating because it’s a piece of advice. I think a lot of people will give you early on in venture, which is like, Hey, you should really start blogging and like building an audience. And even for someone like me who was like writing every day, regardless, I still always discounted it as like, yeah, but I mean, what do I know I’m new to this industry?You know, there’s so many other people writing about this. Like there’s no way I’m going to generate an audience. I have to wait until I know a lot more. and I’m already a partner for anyone to care. And the truth is like, it’s the opposite. It’s the, you know, obviously a partner can generate that interest maybe off the back, but they kind of don’t need to, and there’s way fewer impediments to you, gaining that audience than you think.So. Yes. I think one, if I was starting my venture career, earlier on, I would’ve just like started a regular newsletter off the bat and recognize that like the quality curve would be hopefully, you know, a little steep. and the first, you know, it would take a little bit of time to get up and running, but yeah, I think if you wanted to start a fund today, I would probably start with audience and Content first.And I think writing is. Probably the best thing, for, for tech, I mean, definitely there’s some great audio formats as well, but, I think for some of the complexities of tech, writing is particularly good for it.Nathan: [00:11:39] Yeah. What’s interesting. Is as people dive into this, well, I speak for myself when I start something new, I’m always like, Oh, what if it fails?And so I always like kind of map out what, what does failure look like? One, the, the true failure would be that you write like three essays or something, and then you just stop. But let’s say that I write an essay a week or even an essay a month for, a year. Like my worst version of failure in that is that I’m going to have some number of people paying attention to me.And then the next time I apply for a job that they’re scrolling through and they’ll click to my website. And instead of seeing like something that was updated in 2016, they’ll be like, Oh, He can write, he can communicate these they’re interesting ideas. He seems proactive, right? That’s one like actual worst case scenario.If you show up is that it will make you more employable. And then the second is like, it would meaningfully accelerate your career. And then the third, you know, the third option is like, you could actually have a path forward as a creator. And that’s where I just, I mean, I encourage everyone to write.Mario: [00:12:48] Hundred percent. Yeah. I mean, as you said, at the very least, it’s an extremely valuable skill to have and will make you better at your job and, and more attractive to others. And, you know, on the outside or, you know, frankly, probably more accessible than, than many of us realize, like it can really be a career in and of itself.Nathan: [00:13:08] Yeah. What, what advice would you have for someone who maybe is in tech is consuming all of this content, and doesn’t have that writing background, you know, and it’s like, Oh, but I’m not a good writer. How, how should I practice? What should I do? Yeah.Mario: [00:13:23] I mean, unfortunately I think there’s sort of no huge shortcuts. I think it’s all just like putting the work into, to keep getting better. and for writing specifically, I think. No, you got to just like show up and do an hour, or at least, you know, some amount every day or at least a few times a week, I think, to get really good.And I’m still very much on the path where I feel like I have a lot more to learn. I hope to keep improving and like honing this muscle over the course of my life. and then, you know, you have to read really widely, I think. and in particular, my, Evangelism is I think people should read much, much more fiction.Then is common in business circles. and in tech circles in particular, for a few different reasons. One, I think like a great deal of nonsense section is essentially a Podcast of an app power that has been, you know, bloated to eight hours. and that you can really get most of the meat in a short amount of time.This is not always the case, but I think it’s a good amount of time, the case. And second, like. The cadence and imagination and insight of fiction is like, has a less expressible ROI, but it doesn’t mean it doesn’t exist. It’s just because it’s like more ineffable. and so that is the other thing that I think like hugely helps.My writing is like, because I very, very rarely read nonfiction and has been obsessed with fiction for years. I think that at least helps me stand out from a storytelling perspective.Nathan: [00:15:06] Right. Is there, if you’re trying to hook someone into the world of reading fiction, what are like one or two, series that you would start with?Mario: [00:15:15] I would say my favorite writers are, Ian McEwan, an English author, most famous book is called Atonement. Like I, I think that’s a pretty accessible book and really awesome. He has a very, very short book called, On Chesil Beach, which is like a beautiful small novel. I think like Murakami has a great book called Norwegian Wood, which is weird, but not like full-bent, Murakami weird.So I think it’s like a good intro book as well. but yeah, I think all of those things like. When you’re writing about tech or anything else, having a story to frame this may be more wonkish world and makes it so much more accessible and interesting. And I think helps build an audience.Nathan: [00:16:00] Yeah, that makes sense. Something that you’ve done with The Generalist that I think is really interesting is you’ve brought in, like fellow writers. You’ve made these clubs to try to, get a lot of different people’s takes, but it’s also play this role of, Getting more friends and advocates for The Generalist and, and participants it’s it reminds me of the advice that YouTube would always give to YouTubers of saying like, go and do collaborations.That’s the best way to grow your channel. And you’ve like, systematized it. where did that come from to do it? The S–1 Clubs.Mario: [00:16:38] Yeah, so I think initially it was like pure happenstance that. Things were constructed in such a way as to be so collaborative. I think it was probably ultimately came out of, you know, a strength than a weakness. Like maybe the strength is that I really do enjoy, meeting with other people. I really enjoy learning from other people.I try as much as possible to like, listen less than I. And I sort of speak. and then I would say the weaknesses, you know, from a perspective of insecurity, you know, especially as you’re starting as a creator, for me as a VC, what about like a large public company? I was like, Oh, I’m not the guy who did two years of investment banking or, you know, work that a hedge fund, like my really going to be able to break down this business.Well, but I clearly want to like talk about it. So, how do I like make this amazing? and what I think I learned after sort of the early version of all of this and also RFS, which is like also a collaborative, sort of, project. Is that just like. Yeah. So RFS is, basically my Friday email, every Friday, you get five startup ideas that are curated from some of the best and brightest VCs and founders from leading firms around the world.So you’ll get like a GP of Andreessen Horowitz sharing a startup. They hope it gets made, or. You know, the CEO of like a unicorn company being like, if I wasn’t building this, maybe I would like, think about building this. and so I think it’s, you know, helpful, hopefully for folks that are just sort of going down the idea maze.I think like, you know, at the times when I’ve considered maybe starting a software business, and I think flick anyone in tech has vaguely, entertain those thoughts. I was always like keen for vetted ideas. and so that sort of this, the premise of this, but again, it’s like fundamentally collaborative there I’ll share some ideas of my own, but really they’re everyone else’s and I’m just sort of playing the role as curator.Anyway, all to say that. It sort of came about by accident, but I think to your point, like very quickly early on looking at folks, that, that use YouTube and even audio, it was just like very obvious that collabs help you drive growth in a very different way. And I think they also. Create a very different product, that feels differentiated.So, you know, increasingly the way I think about The Generalist is like a multi pelt, a multiplayer experience that you’re tapping into. so I, I need to do more work on that, but, that’s like informing a lot more of my strategy at the moment.Nathan: [00:19:37] Yeah. I’m just realizing so many creators do it as a, as a fully solo activity, which could work really well. And a lot of people, you know, grow quickly, or like they have the brand of the newsletter as, as their name. But. Like the thing that I noticed about The Generalist is how many people are like in your corner rooting for you and, and for the amount of time that you’ve been doing it, right.We’re two years into this, not even 18 months, basically. Right. and so, and I think that this, as you described it, the multiplayer experience is a big part of it where you’ve built in these two systems where it’s not just like. Hey, we’re fellow creators. We’re all in it together. Like, I’m commenting on your story and saying, Hey, I particularly love this one.Or that kind of thing. Cause we’re friends are interested in similar things. It’s, you’ve actually built in these two systems of the S–1 Clubs and the requests for startups that are every, you know, every week, sometimes we’ve asked one club four or five times a week because it’s been wild. And I’m just thinking about how other people could do that.Like, say if you were writing your newsletter every Monday at Monday and Wednesday, and that was the thing that you were writing, but every Friday, you know, you’re going out and you’re saying I’m. Doing like, and you just make sure your readers know this, I’m doing a cross-post from one of my favorite writers.And so it forces you to do two things, one, go out and meet new people. And then like, to the people who you follow it and admire, like you actually send them the email and be like, Hey, do you want to collaborate? Because I need, I need someone to fill the slot. And I think it really accelerates growth.Mario: [00:21:31] I totally agree. Yeah. I mean, again, Packy I think did a really great job with this, with his Thursday post. Like he writes a Monday post and a Thursday post, and sometimes he writes the Thursday post, but a lot of the time, it’s someone else who, you know, is an expert in something. So. he had, I think one of the founders of managed by Q talking about sort of like the, the new sort of food ecosystem and logistics, and like, this is someone who’s clearly thought about the future of cities, the future of spaces very deeply.And you know, maybe that Dan isn’t running a newsletter, but still takes a lot of value in sharing his thoughts. with an in-built audience and Packy derives the benefits of, you know, his audience in turn. So I definitely think there’s many, many ways to do it.Nathan: [00:22:20] Yeah. Are there other examples that come to mind of, creators who sort of have that collaboration built in?Mario: [00:22:27] The, the one that comes to mind beyond that is not newsletter newsletter related. I would say the, have you ever listened to the All-In podcast?Nathan: [00:22:36] Yes. Yes.Mario: [00:22:38] Yeah. So like that sort of now has just become sort of another Podcast. But I think at the beginning, like really sort of emerged from that same spirit of like, cool, we all have these, these separate audiences, like let’s come together and see what happens.And you know, now it’s a piece of content in and of itself, but, I think it sort of emerged from that same feeling. but yeah, I don’t, I don’t know a tonNathan: [00:23:02] so for anyone who doesn’t know that all in Podcast that’s, Jason Calacanis and and, who else. David Sacks.Mario: [00:23:09] Freeburg and David Sacks.Nathan: [00:23:11] Yeah. Yeah. And I feel like it just started as them. They had like, they want to talk about specs maybe. I don’t know.Mario: [00:23:19] I think so. Just like kind of shooting the shit. Like I don’t, I think it was, just Jason and Chamath to begin with. And then they sort of just like brought in the Davids initially as sort of guests that sort of morphed into full-time, you know, co-hosts but I think, you know, there’s lots of ways to do that with, with newsletters.One of the things that like, I really want to try out soon is. a debate in newsletter format. So take another writer who writes about tech, find a topic where we have a genuine disagreement and, you know, sort of interrogate the two different sides in writing in a newsletter that we both shared with our audiences.And so finding conversation in writing I think is, it’s something I’ve found really, really useful.Nathan: [00:24:14] Would that makes me think about, is like all of you think about collaborations as one plus one equals two, right? Where you have your audience, I’ve got 20,000 readers, you’ve got 20,000 readers and we’ll we’ll cross promote, and we’ll both get this bump and that’d be great. The debate that you’re talking about.Goes and make something that’s bigger than the combination of the two things. Right? You have multiplicative effects because now it’s like, Oh, did you see Mario? And whoever debate that, like, it was so good. And it, because, you know, we both have big enough platforms to get some level of attention, you know, then the fact that the debate is happening turns into a larger thing and it is its own event.And then we might get way more attention.Mario: [00:24:59] Yeah, I think that it adds a fun, fun element in general. I would say that like my, practice for collaborations now is always about pulling someone in to make a piece of content together rather than I think it can be fine to cross-post to, and I bet that like works really well, but I especially enjoy it when I can say to someone like Greg Eisenberg, who, you know, is the founder of late, late.Check-out really thoughtful about community. Has written and shared a lot of public’s thinking about Reddit, where I can sort of like tap him and be like, Hey, I want to do a deep dive on Reddit and why it’s this crazy undervalued company? Why don’t we do it together? and so, you know, that’s something we released over the weekend, but I think it was a good example of like, I don’t think alone either one of us would have made it as good as it became.And, you know, it was, it was valuable for both of our audiences and still achieve the same growth bump.Nathan: [00:26:00] That is interesting. I feel like I have these topics that I riff on with friends. Like for example, I wrote a post called the ladders of wealth creation, which is an idea that I started with and then got input from, from friends, but like probably a third of the ideas in the post or more are from James clear and like him and I riffing on it.And so that would be the same sort of thing of like, I guess finding those topics that you, you know, you and that particular friend are talking about, you’re both obsessed with and just say, let’s go make this together. Cause then the other thing that we’ll do is then the two of you, like, you have to promote it more because you wrote your friend into writing it, you know, you can’t be like, Oh, that’s just the Thursday post.I got it out. Cool. What’s onto the next week. You’re like, I pulled my friend into helping write this. Like now we’re both going to actually promote it and share it and make it worth while, which is of course better for everybody.Mario: [00:26:53] Yeah. And it also just like leads itself to Content extensions more easily, right? Like you can then have a conversation around it in a clubhouse room if you wanted or something else. And like, you already have this other person who is like deeply invested in it with you. and like, you know, you get that conversational aspect to it.Nathan: [00:27:14] Yeah. Do you have like a list of people? that back when I did a lot of sales, I for ConvertKit, I would have like, sort of this dream 100 list of people that I wanted to have on ConvertKit or like, do you have that for collaborating?Or you’re like, okay. Here’s who I want to reach out to, but I’m a little nervous to send the email or something like that.Mario: [00:27:33] Yeah, I have, I have a list like that where I would say it’s not so much that I’m nervous. I’m just like, I have to know. Exactly what the right project is. so for example, a person whose newsletter I love and I’ve collaborated with him on an S one club, is just engage, who writes technically great newsletter.And like, I know I want to do a collaborator with him, but I didn’t have a clear idea until recently where I was just like, okay, this is it. And so we’re going to, we’re going to do something that’ll come out soon. and so I think that’s the, that’s the pitch. And then sometimes, obviously like I’ll pitch someone an idea and they’re like, eh, I I’m too busy or but that’s okay too.Nathan: [00:28:18] Yeah. Well, that’s good. I think having the list written down like potential ideas and then people you want to collaborate with and just keep adding to those. And then sometimes they overlap and you’re like, you know, or you’re like, I really want to work with this person, but I don’t have the right idea yet.And then when the idea comes, then it’s like, Oh, I got the perfect thing.Mario: [00:28:37] Exactly. Yeah, I think it, I, I definitely like having the list because it also just like, even just writing that list, it gives you so many ideas.Nathan: [00:28:44] Another thing about the lists is sometimes I like anything that will be a snapshot of like your current, a worldview of what’s possible.So for example, early on for ConvertKit. That list had people like Tim Ferriss, Gretchen Rubin, other people as like who to get as customers. And so when you write that, when you’re like, Oh, it would be insane to collaborate with this level of person. And then like a couple of years later when it happens, you’re just like, Oh yeah, well like their peers, you know, of course we know I have like 10 friends in common, so we just finally made it happen.But by writing it down, you get to have the snapshot of like, Past me thought this would be incredible, you know? And so just like you’re talking about with, you know, wrestling with the guys on the, on the Twitter spaces the other day.Mario: [00:29:33] Yeah, a hundred percent, I think. well, there’s, there’s some, I think it’s Aristotle, or one of the, the old philosophers, which is like, you know, the, I can’t remember the exact quote, but they just have, it is essentially like, don’t forget that you have things that you once desired greatly. and like, I think that’s often the case where you sort of, treat happiness or pride in your work as a moving target that is really fleeting.And those lists, I think, help remind you that like, yeah, it wasn’t that long ago that the idea of collaborating with this person or having this person send a nice note about your work would have like blown your mind. and now it’s like, cool. Yep. That’s awesome. Next.Nathan: [00:30:28] Yeah. Yeah. For sure. One of the things that’s really impressed me about how you’ve grown The Generalist is you’ve taken it really seriously. I don’t know if it was from the beginning, but from the point that you and I met, which was probably what maybe April or may of last year, June, somewhere in there.Yeah, that sounds right. And to the point that you, talk to, did you recruit a formal, like board of advisors or informal advisors?Yeah. But you, you had a pitch deck for it. You outlined the business model. like what made you take it so seriously rather than, you know, kind of be like, Oh, Write every week and see what happens.Mario: [00:31:11] Probably a mixture of like personality defects and, excitement. I think like, I just really love writing very, very much. And so as soon as I got the width that like, maybe I could make this a real thing, then suddenly like a flip switched in me where I was like, all right, I have to go as hard as possible.And honestly, like I would say that switch had not. Been flipped in me since college, like as a student, I was an absolute animal. Like, that’s not a very cool thing to say, but I was just an absolute nerd. I was a relentless studier. Loved it. And, I think it was because. You know, I felt very empowered to study whatever it is.I wanted like go as deep as possible and feel like the value was accruing directly to me. and I think the struggle for me as an employee was always like, I’ll give you 90%, but I don’t want to give you a hundred percent because like, I kind of need the 10% to do something of my own or, you know, because I sort of resent it.And so. As soon as I was like fully on my own thing, I suddenly felt like, Oh man, I’m unchanged to go after this. and then I think the second piece of it was just that, I wanted to convince myself to a certain extent, that this could be real. And so making a business plan, bringing on people who I felt like could support and advise me and like make me better.All of those things started to convince me that. Okay. And maybe you’re not crazy. Like maybe other people seem to see something interesting here. and your math adds up more or less that like, maybe you can make this work.Nathan: [00:33:08] Yeah. Yeah. I think that, well, one, if you’re looking for advice from anyone showing that you’re already in motion and that you’re going to make it happen, like the number of people who reach out and say like, could I pick your brain or whatever else?And they don’t have any track record that they’re going to implement it. You know, is, there’s just, there’s so many. And so when someone comes along, who is like, Hey, I need advice on this specific thing. And you’re like, yeah, there you go. And they take action. And then they come back like a month later and be like, that works really well.Hey, could you help with this? It’s sort of addicting to help those people. And that’s what I found early on for ConvertKit where people like Amy Hoy and Heaton Shaw and Patrick McKenzie, and so many others would come and help. Because I would like immediately turn around and try out theMario: [00:33:55] Do it.Nathan: [00:33:56] That they said. And I see you doing the same thing.Mario: [00:33:59] Thanks, man. Yeah, I definitely try to, I think it’s, you know, early days you just got to keep a pretty high velocity as much as you can.Nathan: [00:34:07] Yeah. So let’s talk about growth. if you’re up for it, I’d love for you to share some numbers of where The Generalist is at now. And then we can dive into, how we got there on the growth side.Mario: [00:34:19] For sure. Let me actually pull up the, the live, the live look so I can be exact, ConvertKit tells me I have 27,147 subscribers. So thank you to every single one of them. And opens are 53.52,Nathan: [00:34:43] That is a very impressive open rate.Mario: [00:34:45] Thank you. Thank you. it’s weird. It went up as I’ve grown, which I did not expect. Now it’s more or less stabilized, but I think when I went full time, it was at like, I dunno, I have to look at the deck, but somewhere around 49 to 50. And it’s now con consistently above 53. I mean, it’s a small improvement, but like, I like to see it.Nathan: [00:35:09] Well, I mean, especially when you multiply it out over a larger, you know, a growing number, right. When you multiply gets 10,000 versus 20,000, It’s a lot more. and I always encourage people to track engaged subscribers as like their metric, you know? So total subscribers times open rate, because then when something comes along, like if you have hung your whole like, self-worth on, total subscribers, you know, and then it comes along and you’re like, Oh, I got these 10,000 who are just dead weight and don’t open anything.And you’re like, I can’t cut that because like having a newsletter of a hundred thousand people is like, Part of my identity or something, you know, but if you’ve been focused on engaged subscribers, then you’re like, I don’t lose anything if I cut those people.Mario: [00:35:53] That’s really? Yeah, that’s a, that’s a great point about just like tying it to your identity. I love the engagement score you guys have, by the way. I don’t know if I’ve told you that, but ah, so nice to see that.Nathan: [00:36:03] Yeah, it’s a fun, a fun little feature. And then on the, so you went, you went full-time in August about six months ago. how’s it been on the revenue side?Mario: [00:36:16] So I didn’t, monetize until. One month ago, almost exactly. It was January 24th. so that was the day I opened up memberships and was also, shortly after I started to like circle back to a few folks that have been interested in advertising and sponsoring in the past and was like, Hey,Nathan: [00:36:37] There, there was no way to pay you or for you to make money from it up until that point?Mario: [00:36:41] No, it was all free. and honestly it was like, There wasn’t probably a good reason for that. I think it was partially because I wanted to build a little bit more of my own stack with Webflow and Pico. And of course you guys, and I didn’t want to start it on sub stack. I was already switched over at this point for a long time.And so I wanted to have like a really awesome site and home for the Content before I switched on memberships. And it felt a little bit strange to accept sponsorships before that point, just because it wasn’t really the way I expected to make the majority of revenue longterm. so yeah, flipped it on, on January 24th and, it’s gone really well so far.Nathan: [00:37:33] Nice, nice. You were mentioning like how it compares? This is before we were talking, how it compares to, you know, past salaries, Do you track that? I guess like percentage of salary?Mario: [00:37:47] Yeah, I think that’s like a nice way for, for me to look at it. and this definitely validating. So in the first month, I have to check, but it’s something it’s around 85 to 90% of my best ever salary. In the first month. So that was like, I know it’s not always going to be like that. I think there was a huge, like initial bump and because of the types of memberships I did, like, I have a believer membership where someone buys five years effectively upfront.There’s a bunch of like essentially bookings pull forward, but still the growth has remained really good throughout the month. There’s still a good base of people who are on this sort of monthly or annual plan. And it really feels very much like it can be a business. So, you know, it’s now really up to me to make sure I don’t blow it. And you know, just keep executing as well as I can.Nathan: [00:38:48] Yeah. I mean, that’s exciting to have that much traction, like the moment you turn it on now, like, as you said, you waited awhile to, to monetize right.Of having, you know, well over 20,000 subscribers, by the time that you turned that on, but it means that you can come out and have this big splash, which is great.Mario: [00:39:04] Yeah, it feels, it feels good to like get, get a, sort of a nice bump to it. But I think there’s plenty of other people who start much earlier on and then, you know, that can work wonderfully as well. And you probably get a lot of interesting learnings. From, you know, monetizing early, finding out what people actually are willing to pay for.Like, those are all things that I’m now just learning, which is like, cool, what should be in front and behind the paywall? You know, what’s the sort of messaging even that converts people, because I really haven’t spent time thinking about that today.Nathan: [00:39:37] Yeah. How did you structure what’s in front of him behind the paywall? cause that’s something that I think a lot of people run into of I’m putting out this content and it’s really good. So it should be behind the paywall, but I want it in front of you in front of the paywall so that it can help me attract more readers.Mario: [00:39:55] Yeah, the tricky thing I would say is that because of the, like multi-player elements of The Generalist, it’s not that easy to put a lot of the content behind the paywall, because the people who contribute on an S–1 Club, like a lot of them are. The GPS of a venture firm or a CEO or an expert, like they’re doing it because they’re really interested in this subject and genuinely want to share their thoughts and trade ideas with other smart people, to limit the view of it feels like probably against their interests, even if I’m not sure they would necessarily.Express an issue with it, but it kind of doesn’t feel totally right to me. so those things I think are easy to put in front of the paywall and those are things also that are easy to monetize with sponsorships. So that’s great. then there’s, I would say like a lot of more intimate or deep content that goes behind it.So every Sunday folks get a briefing from me, which dives deep into some. Area of tech or the financial markets often it’s, you know, sort of unpacking an investment that I think might be interesting or a technical trend that I think is worth keeping in. and you know, or free members, free subscribers get one of those a month and paying subscribers, get four of them.And then the other piece of it, I would say is, you know, there’s a bunch of other parts, but the, the core. Element, is this community, so I now have a, a community which is only for, for paid members. it’s ended up being like very senior impressive group of folks. and so it has more of a feel of like a private conversation.That’s ongoing with people that it would be probably like hard to get access to otherwise. that I think has also proven like a really. Useful conversion tool and also a, something proves the content itself because often before I write something, I’ll post about it in the community and then five or 10 people will say, Hey, have you thought about this?Have you thought about that? And so it sort of has a nice, nice effect in that, in that regard too.Nathan: [00:42:22] Yeah. And is that a community that you’re hosting on circle or Slack or somewhere else?Mario: [00:42:27] Yeah, circle. I thought a lot about, you know, where to host it. Ultimately I felt like circle was going to be the best call and, and so far I really like it.Nathan: [00:42:37] Yeah. It’s been interesting of, of seeing communities become such a core part of a lot of newsletters. have you found, like, are there any downsides to it? Is it a pain to manage? Is there anything else or has it just been all upside?Mario: [00:42:53] I don’t think anything SaaS, upside, I think like, you know, everything, everything has downside. the downside of community is time. I think. it’s just, I don’t think it works if you just sort of flip it on and expect it to take off. And actually I think like that’s potentially a trade-off versus. live chat platforms like discord or Slack or telegram versus something that’s asynchronous like circle.If you start a Slack group with 50 people, it very quickly feels busy and lively. once you hit 500 people, it very quickly feels noisy and chaotic. Whereas I think circle is sort of the other way around, which is, you know, 50 and maybe feels a little sleepy. and so you have people sort of like. Maybe looking for how to get the conversation going.But my hope is that really, as you scale, it leads to more focused, thoughtful discussions rather than just sort of like incessant back and forth and people like self-promoting stuff in this channel all the time. and those sort of things. So the, the trade off is time.Nathan: [00:44:05] Yeah. Yeah. That makes sense. And so I could see circle being something that you have to grow into. Whereas Slack being something that you would probably grow out of. And so that’s a good thing to think about, of like, what’s the long-term play for this community. And are we going to get into that, you know, 500 members and beyond, and if so, like go for a platform that’s a good fit for that.Mario: [00:44:29] Yeah. I ran a bunch of like Telegram groups on the side that weren’t like formally part of The Generalist, but I would, as part of the Friday startup ideas newsletter, like allow people to join this group if they applied, And it was great. I really liked it. but at a hundred people, it was already occasionally like quite noisy.And I didn’t think it like created a compendium of knowledge in the same way as something like circle can where you can suddenly search like, you know, RPA. And there will be a really interesting thread that someone wrote and bunch of smart people commented on that, like is now this living document, in a really scannable way.Nathan: [00:45:11] Yeah. That makes sense. What about pricing? how did you come to the pricing that you chose?Mario: [00:45:16] Yeah, I actually, I want to write about this. probably not in the newsletter, but, maybe on Twitter or something, to explain it because I think people it’s either two reactions. Either someone thinks it’s a total no-brainer at 19 bucks a month. and you know, sometimes even folks will be like, I think you could push this higher off the record.Or you get folks that are like, why is this 19 bucks when Netflix is 12? and The Economist is 12 or whatever it is they are at. and the answer really is like a few different things. But one is that I think I’ve engineered as much as possible. The Generalist to be able to return your value like 10 or 20, or, you know, maybe even a hundred fold.In a few different ways, like the ways that I think someone gets to the point where they are really like ripping me off, let’s say, is if I can get them into a company that they think is really interesting and investment that they think is really interesting either in the public or private markets, that I helped them find a co-founder or a key hire for their existing company.That I give them a startup idea that they then are able to use to build their next company. or I introduced them to just like an amazing colleague, whether that’s another investor or, you know, a fellow founder, whatever it is. And so in each of the pieces of content and the community, I think there’s the potential for that.So you have the Friday newsletter, which has five startup ideas. If one of the, you know, 150 that I think we have right now from these great theses and founders, like resonates with you or gets you closer. I think it’s a total no-brainer it was obviously worth 20 bucks a month or 19 bucks a month. if the S one club helps you make a smarter decision about whether to invest in a stock or not.No brainer. If the weekly briefing gives you either, again, a stock that you’re interested in or a private investment that you might want to make as a VC again, no brainer. and then the community, hopefully like stitches a lot of those pieces together where it’s like, cool. I know that you were interested in this startup idea because you told me about it.Now it’s time for you to meet this engineer who like also said they were interested in it and like, maybe you guys should jam on that. and so this is something that I sort of tried to outline in an interview. I did with Alex Danko who writes one of my favorite newsletters. And it’s just like one of the smartest people in tech, in my opinion.I think there’s a real. sort of almost mismatch in how consumers pay for a newsletter and how they receive value. Like consumers pay on this really linear timescale. It’s like 19 bucks a month, 19 bucks a month, 19 bucks a month. Realistically, you probably won’t read every piece. I write if you’re a subscriber.And you probably won’t see like every comment in the community, but as long as each individual piece of content has the ability to be worth like. 500 bucks or a thousand bucks to you. Like, I can take it my time. Hopefully if you’re willing to be patient as a reader and you might not read one, two or three, you might find four boring, but then five might give you your startup idea or, you know, in the six week you might meet your cofaq.So I think there’s like a linear line on the consumer side and a super lumpy one on the value realization. so that was a very. Inside baseball, look at how I think about the pricing, but, that’s sort of where my head’s at at the moment.Nathan: [00:49:12] Yeah, that makes sense. if you know some of this other stuff you had, what was some of the split between like monthly and annual and of course you probably launched your biggest fans.And so it’s probably going to be a higher split annual. Upfront,Mario: [00:49:25] I don’t, I don’t know what it is actually. I think when I looked last, and this was a few weeks ago, so it’s like a little bit out of date. I think I would make 5% of my best salary per month. So it wouldn’t get me there on a yearly basis, but like, you know, would get me part of the way there. And then plus the annuals I’m yeah.I’m not sure what the split is. There was a good amount. I want to say maybe 10 or 15%, maybe as high as 20, that were believers. people who bought the five years upfront and, that is like amazing for me. One, because like, It’s very nice that people like are excited to be a part of this for five years.And to also, because I think it hopefully allows me to like, reinvest that money in, in continuing growth.Nathan: [00:50:29] Yup. Well, I love that you gave people that option, you know, like I think someone who would launch just with monthly and say it’s 20 bucks a month and then go like, okay, I guess I should have an annual version. People say that churn is better, so sure. I’ll do that. And you’ve added this, this third tier of saying like no pay, is it $600?Something like that.Mario: [00:50:50] Yeah, it’s a $642.Nathan: [00:50:53] $642, you know, just say like, Hey, all of this upfront and the way you message it around, like, you know, the believer tier, I think is really good. Cause for a lot of people. Especially in your audience, right. You’re going to have the whole range, someone who’s going to be like, Oh, 20 bucks a month. Yeah, no, it’s worth it.Like, I’m going to go for that. And you’re going to have other people who are like $600. It’s it’s going on the company credit card. Like, it just doesn’t even, it just doesn’t even register. And so, but that person would have given you $20, if that was the only option you’ve given them. And soMario: [00:51:25] A hundred percent.Nathan: [00:51:26] Always give them the other options.When I was selling eBooks, I would do, like. Books into courses and do tiers and your $39 $99 and then $249. And like a quarter of the people bought the $249 options, but it represented like 55% of all revenue.Mario: [00:51:46] There you go. There you go. Yeah, that makes sense. yeah, people have asked like, Oh, are you going to get rid of the believer tier soon? And I’m kinda like, I don’t really think so. I think I’ll just like, you know, maybe as prices change, maybe I’ll adjust it or something like that. But like, if someone is excited to sign up for five years, like,Nathan: [00:52:05] Right. I might even play with it of decreasing the, like, if I think if I were flying with this, I wouldn’t do five years.I would do two years or something like that. And maybe there’s some other perks in there. but it is this high price that renews, like what if, what if the believers here was a thousand dollars a year? And maybe it has some extra things in it, but it really is like the believer tier. And I don’t know if they would go for it, but I’m curious if they would, and if I were doing it or maybe it’s $400 or $500 a year. And I would just be curious if people would sign up for it, my guess. Is that, that some wayMario: [00:52:49] I think you’re probably right. I’d love to get to the point where I can like more explicitly message. What are the things I’m doing for those people right now? I’m like, cool. You get fast-tracked into the community. You are going to have some like extra events and channels within the community. So like, you’ll have these moments of intimacy that like you are sort of getting, because you are so, such a believer in this, but I think you’re totally right.Like, it probably is, is something I should think about of like, how do I build that extra two 50 or 300 bucks of value for someone on an annual basis that, that makes it worthwhile.Nathan: [00:53:31] Right? Yeah. I would even, you know, put a badge on their profile in the community, you know.Mario: [00:53:37] It happens.Nathan: [00:53:38] Oh, good.Mario: [00:53:39] Yeah. I’m a big believer in badging.Nathan: [00:53:44] At all.Mario: [00:53:47] I think people like it and I think it’s fun and, you know…Nathan: [00:53:50] Yeah, good stuff. Well, thanks for coming on. This has been really fun to dive in and talk through all the details of The Generalist. Where should people go to subscribe and then to follow you around the web?Mario: [00:54:00] Awesome. Yeah. you can sign up, ReadTheGeneralist.com, and, I’m mostly active on Twitter. So, if you look up @mariodgabriele, on Twitter, That is me.Nathan: [00:54:15] Sounds good.Mario: [00:54:16] Know, still free to shoot me a DM or an email sometime.Nathan: [00:54:19] Perfect. Well, we’ll link to both those in the show notes and we’ll chat soon. I’m excited to keep watching, watching the newsletter grow.Mario: [00:54:26] Thanks man. Well, fingers crossed. I can, I can continue to deliver and that, you know, I have to thank you. And, and the team so much for one making a dope project, a product, and, to helping so much along the way with your advice and support. So I appreciate it a lot.Nathan: [00:54:43] My pleasure.

Sam Parr founded The Hustle, a top-flight newsletter that he grew to almost 2,000,000 subscribers… and just sold to HubSpot! Tune in to hear the whole story of how Sam grew a successful newsletter to seven figures per month in revenue, and the roller coaster ride of selling his small business.Despite his success with a paid newsletter, Sam has lots to share about what people are doing wrong when they launch a Substack. Plus, he gives Nathan ideas and tactics for growing a new, local newsletter that focuses on Boise.In this wide-ranging conversation, you’ll also hear about the art of writing quickly, whether writing your newsletter is something you can (or should) delegate, and whether running a solo newsletter is even the right business for you in the first place.Links & Resources HubSpot - Inbound Marketing, Sales, and Service Software Product Hunt – The best new products in tech. DailyCandy - Sweet Sorrow Thrillist - Find the Best and Most Under-Appreciated Places to Eat, Drink and Travel Fool.com: Stock Investing Advice - Stock Research James Clear Gumroad Glossier - Skincare & Beauty Products Inspired by Real Life Sam Parr’s Links Subscribe to The Hustle Daily Trends by the Hustle - Your next business idea, delivered weekly Twitter: @theSamParr Episode TranscriptSam: [00:00:00] I think they’re making the wrong mistakes. The first example is pricing. Most people charge way too little, but if you actually want to make a living at this and provide value, you’ve got to charge more money. How are you gonna make a living if you’re charging $4 a month? That’s really, really hard.So charge way more. People tend to like that stuff more. If they paid money for it, they usually appreciate it. Nathan: [00:00:25] In today’s episode, I talked to Sam Parr from The Hustle. Now Sam and I have been friends for a long time. And he’s got some pretty wild news in that, HubSpot just acquired The Hustle. There’s a lot of crazy things that went on with that, but, we dive into the story there. How long due diligence took everything else.It’s a long ranging free-form conversation. But we hit another things like, my new local newsletter that I’m starting. He has some growth ideas and tactics that he shares there. We get into what he thinks people are doing wrong when they’re launching Substacks, which is pretty wild since he has crazy revenue.I think, you know, there are over a million dollars a month in sponsor revenue and getting pretty close to that in paid memberships revenue for The Hustle. And we get into growing the newsletter to almost 2 million subscribers. There’s so much good stuff. I’ll warn you. It’s a very rambling conversation, but we have a great time.So I hope you enjoy it.Sam, thanks for joining me.Sam: [00:01:18] What’s up, man?Nathan: [00:01:19] So you would have been friends for a long time. It was hung out in a lot of different circles. You’re wildly popular on the internet today, not today, over the last couple of months, a couple of weeks. Sam: [00:01:30] Not as popular, popular as you.Nathan: [00:01:32] Exactly. I don’t know, but you just sold The Hustle and we were talking right before we hit record and you’re like, dude, just hit record so that we can have the whole conversation for everybody. On the first question I was asking is how long did it take from when, when HubSpot reached out to the deal actually closing,Sam: [00:01:53] About 90 days. Well also, had you ever sold this business before?Nathan: [00:01:57] I have not, I can’t say what business I acquired, but this week I acquired a company. it just closed. Sam: [00:02:06] Was it a big deal?Nathan: [00:02:07] It was a medium deal.Sam: [00:02:09] Okay. That’s great. Well, we,Nathan: [00:02:11] If you bucket deals into small, medium and large, it was a medium deal. So.Sam: [00:02:15] Well we, We, like, I didn’t know. I mean, I had been part of a company selling before as a shareholder and like a investor, an advisor, a very, very close advisor, but I still didn’t know. I didn’t know like what closing meant. I didn’t know what signing meant. I didn’t know. I didn’t know anything. And so I didn’t, I didn’t know what a LOI was.I didn’t know. I mean, I had heard the words, but I didn’t really know like what that implied. And they reached out to me around September or October. They cold emailed me and we had been recruited or, you know, buyers have talked to us for a long time. And like the first couple of times I took them really seriously.And I was like, Oh my God, like, I’m going to dress up nice and fly out to their office. And I’m going to show them all this school stuff. And then after awhile I was like, I just didn’t take it seriously. And I just said, I would send them like, I would like write up like a one pager and I would like tell them all the reasons basically why they shouldn’t bias where, I mean, I was like, look, we’re really good at this.We are horrible at this. the reason why you should buy us as this, the reason why you should not bias as this, if you are, the, the, the expectations for pricing is around this. If you want to talk, call me and like, it was a pretty straightforward thing. And, they liked that. And most people don’t, most people don’t like that.And so they emailed me and then we, we, the deal was announced, like the last day of January and they emailed me in October.Nathan: [00:03:47] So I feel like that’s pretty quick.Sam: [00:03:49] Is it? It certainly doesn’t feel quick.Nathan: [00:03:51] You mentioned on, on your podcast, that due diligence was. I think hell was the phrase.Sam: [00:03:59] It is so bad. It’s so bad for a bunch of reasons. But first of all, I sold to a public company.Nathan: [00:04:06] Yeah. Sam: [00:04:06] I’ve never sold a company for $300 million, but I have a feeling selling for 300 or 500 or actually have been the same amount of work as for what we sold, which was less than 300 million. it’s a ton of work.And the difference between my small company, it was that I didn’t have a team of like, I don’t ha I had like one woman named ed who works on accounting and finance. And then I had outsourced a lawyer, you know, like an outside law firm. I had an outside tax firm. And then I had me and I had to do a lot of this in private.You can’t really tell employees. And it was very, very hard. They basically, I had an Excel spreadsheet that had like eight tabs. One was like real estate. So you like your office leases and things like that. Another one was like it. So like your computer setups and all that. And then another one was like, Like rev, P and L like FP, a what’s it called financial planning and forecasting and, and, and your profit and loss forever.And then another one was like the Daily email. Another one was trends. And then there was like three more. And each of those tabs. Literally had 150 questions on it, like a PO like, so it was like post revenue every single year since starting posts like aging account receivables every year for the last five years.And I’m like, I don’t even know what aging accounts receivable means. and it felt like that for like everything. And I’m not, I’m not bullshitting you. I probably gave them, I probably gave them 700 things. maybe 500. It was just really hard. I mean, you’ve been through it, but it’s just, and the thing is, is that I think founders and CEOs are a little bit different.Like I didn’t talk to the founder of HubSpot too much during the deal, but I did sometimes, and I ha and he was like, He would make jokes, but I have a feeling they weren’t entire Joe, they were, he was kind of being serious. It’s kind of not, but he, you know, he, the folks were doing a lot of the work and he was, have we closed yet?I’m like, no, man, we’re not going to close for another three weeks. He was like, man, they should hurry it up. Like he would make, he would like tease, like he’s ready to do it. But like, you know, the, the people doing the work, they, they, they need a button, everything up really tightly. And maybe you and me, if I bought a company and you just did buy a company, you’d probably probably be a lot more lax because you’re like, We’ll worry about the details later.You know what I mean?Nathan: [00:06:22] Well, that’s how I was. We got to, so in our acquisition, when we started the conversation in September, and then by like late November, there was actually a thing like seriously talking and then just before Christmas, We got an LOI signed and I thought like, great. Now it’s just like verify that everything is correct and accurate, you know, we’ll, we’ll take like two or three weeks to do that.And then our attorneys were like, no, no, that’s not how this works. And I mean, we, it still took us only. It was like 50 days to.Sam: [00:07:01] That’s crazy. That’s still so long, right? Nathan: [00:07:04] I was like, I thought we should do it in 30.Sam: [00:07:07] Yeah. When someone talks about, like they said, like, All right. They’re like, all right, we have, this LOI and then we’re going to close before 90 days. And I’m like, I don’t even know how I’m gonna want to sell in 90 days. I don’t even know if I’m going to like, you know what I mean, 90 days that’s a whole, is that a quarter?Nathan: [00:07:21] Yep. That’s a quarter of aSam: [00:07:22] Like, I don’t even know what mood I’m going to be in. Like let alone, I don’t even know if I want to do this in 90 days. How am I going to sign up? You know what I mean? So it is pretty crazy.Nathan: [00:07:30] So I’m curious, like on the announcement side of things, one thing that I saw, I saw two conflicting things, right? Axios reporting, a purchase price of 27 million or whatever. And you saying like, that’s one I’m not ever saying with the purchase prices and two that’s not it. so I’m curious how, how did that price get out and your take on it?Sam: [00:07:52] I don’t know how it got out. I didn’t talk to anyone. I’ve never taught. I’ve never talked to anyone about the price. The only one I’ve ever talked to is probably my wife. How it got out. I don’t know. I’m not going to confirm or deny it, but I’ll tell you this. Brian, I told HubSpot I’m like, I don’t want to reveal the price.I told them that. And Brian, the CEO got wind of it and he goes, why, why? He goes, he goes, because Brian was cool. He was like, have you ever talked to him in Dharmesh?Nathan: [00:08:22] I know Dharmesh from years ago, like at business of software and all that, but I’ve never met Brian before.Sam: [00:08:27] They’re cool. Like they’re, they’re I bet they’re billionaires rich guys, but they’re still like, down to earth. Cool folks. And he was like, Hey, he’s always been like, Hey, just like, if someone gets in your way or someone keeps you guys from, like doing what you want to do, please let me know. Like, he’s really cool and great.And he was like, Hey, I noticed you didn’t reveal the price. Did our people tell you not to do that? Because you can, if you want. And I go, no, it was me. And he was like, well, why? And I was like, Brian, don’t you think it’s weird that I can Google your salary? You know? Like I just saw that you sold, sold $3 million worth of shares.I saw that you did this, this, and this it’s all public. And he goes, yeah, I think that’s weird. And I don’t like it and it makes me uncomfortable. And I was like, yeah, that’s why I didn’t want to do it. It’s kind of like a weird thing. I don’t think it’s important, Nathan: [00:09:08] Yep. Sam: [00:09:08] But a lot of people like gave me a hard time because on my podcast, I’m the guy who asks all of these important money questions, but, I always am respectful.If someone says they don’t want to talk about it. And in this case, I didn’t really want to talk about it, but I’ll say this, that when it came to business, I read a bunch of books about like life philosophies, and I could tell you about the books or whatever, but my goal was to make enough money by about 35 that I can live a incredibly lavish life and still leave a huge sum to my children.And this deal allowed me to do that. and the reason why I did that was the way that I set my business up early on, I raised a little bit of angel money and I don’t entirely regret doing that because it’s hard to say if this would have happened without that. But I do regret doing that because I wish I never would, like, I don’t ever want to sell anything ever again, you know, I want to own stuff forever, but that would have been against like my duty, if I promise someone something like I have to.I got to do it. So the reason why we just decided to sell was it L it got people return and it allowed me to achieve a personal goal.Nathan: [00:10:21] Yeah, that makes sense. I mean, on the selling a company, that’s something that I think about, like we have opportunities to sell ConvertKit and I. You know, always have the same answer of like, no, we’re never in a cell. but I have a little bit of a problem in, I want to figure out how, like, I, I have issued equity to the team.And so I spent a lot of time thinking about like either a company buy back program, for anyone who wants to sell or like some version of like angel list or, like Carta has their car to X, you know, or something like that, where the team can sell shares without selling the whole company.Sam: [00:10:58] And I actually based a lot of my philosophy off of your blog. So you, on your, on ConvertKit values, it was like, independently reach a hundred million in revenue. I think. Nathan: [00:11:09] Yep. Sam: [00:11:10] Is that right?And then you’ve also said that you were not going to give any equity. And then about a year ago, your opinion changed and you gave equity.And you’re like, my opinion changed because even though we’re not going to sell, it makes these people feel like they’re part of this and I want them to feel that way, so I’m going to do it. and so I agree with that, but I don’t entirely like the solution that you came to, I think is still not optimal.I S I think it’s the best of the worst. and because you still need them to sign off on some stuff every once in a while now, I don’t know exactly how you set it up, but if someone’s an equity holder, they, even if they’re a tiny equity holder, they can still have a little sayNathan: [00:11:50] Yeah. So in this case we have options for everyone. And so, you know, they they’re holding options rather than direct equity. so, you know, they have things like information rights, but they don’t have to sign off, on a deal. Now I know other people who are like, Would never get, even give information rights, you know?Cause they’ve had someone who’s like a VP get to a VP level and then switch. And now they’re having to send out like, there, you know, like quarterly reports to all their shareholders and one of their shareholders now VP at a competitor, you know, and thatSam: [00:12:26] Yeah. And it’s weird, right? Nathan: [00:12:27] Yeah.Sam: [00:12:28] But I’m okay. I totally agree with your premise though, of like, I want people to share in the success.Nathan: [00:12:33] Right.Sam: [00:12:34] I want them to be bought in. If someone works really hard and provides a lot of value to the company, I want them to have a cut of it. I actually, you have a profit sharing thing that I try to do at my company, but it didn’t work because we didn’t, I didn’t set the business up the right way.So like I’ve actually built or I wanted to build a lot of my stuff off of the things that you’ve done. But, the way, just the way that I structured everything early on, I, it, it’s pretty much very impossible, almost impossible to like reverse it, to do some of the things that are probably more optimal.But I, I think that like, I wouldn’t want to sell for a long time or ever, but like I got sick and. July or September or something. I got Lyme disease and it wasn’t quite like deathly, but it was like really bad. My face was paralyzed and I couldn’t move my face and I was struggling to talk. And I was like, it would be nice to be wealthy enough that an emergency, like this wouldn’t ruin me.Nathan: [00:13:34] Right. Sam: [00:13:35] And, and it also made me reflect that like maybe business isn’t the most important thing. And so that’s one of the reasons why I did the deal, but I, I don’t know how you feel, but I mean, you’re one of like the people I look up to in business, but, I think that most days you don’t ever want to sell, there is a few times where you’re like fucking them out.Nathan: [00:13:58] Yup. Oh, for sure. But most days, like, I don’t know how you feel on having the platform and the reach side of things. But when you get to the point that you’ve got, you know, hundreds of thousands of people paying attention to what you’re doing and the case of The Hustle, you know, millions of people, it just takes, I remember what it was like before that and how much work it was to get attention for something.And so a lot of what I have is not wanting to give that up of like, when I have something new come out, like you can launch it. You can. You know, get traction really quickly because you have that whole platform. So that’s where it’s like, I would, I don’t think I’d be excited about starting over, even if it was the pool of money.Sam: [00:14:39] Yeah, I think that’s it. Like I just sold, like we have close to 2000 or 2 million subscribers.Nathan: [00:14:45] Is that that’s how big the guy I had, I had 1.5 million. So you’re you’re even to of course numbers keep getting bigger, but.Sam: [00:14:51] Yeah. I mean, we’re adding a lot of people. It’s not quite 2 million, but it’s pretty close. And then we also had tens of thousands of paying subscribers. Nathan: [00:14:58] Right.Sam: [00:14:59] so yeah, it was big. and like our open rate, like the other day we had 900,000 people open. so like it’s, it’s pretty big. Sam: [00:15:13] But, and to start what we started, like, when I say back then I’m referring to like literally four years ago, but it’s way harder now.It is way harder now.Nathan: [00:15:25] What, what do you think is different now?Sam: [00:15:27] There was less competition. I, when I told this, I like made a list of like heroes or like people I looked up to. And business. And I emailed them and I there’s, a lot of them are media executives or media CEOs. And I told this one guy who, if I told you his name, you would know it I’ll tell you after.But he was like, this business will never make more than $2 million a year. And I was like, why not? He’s like the email. He’s like, that’s stupid. Who makes an email? Like you guys need to do video or, Nathan: [00:15:54] Something trendy in now.Sam: [00:15:56] Yeah. He was like, how are you gonna get traffic to your site? I’m like, you don’t get it, man.Like, You’re on your phone, like who cares if that four inches of white screen is on Sefaria in the mail app? Why does it matter? And in fact, it actually matters for email because I already can do the math that this person, if they only unsubscribe every, at a 5% rate throughout the course of a month, I know what my churn is.I know what my LTV is. I know how to win, then what I can spend to acquire a customer. Like I’ve just like, you can’t do that on your website. And they’re like, yeah, but like, people don’t want email and now that’s totally changed. You know, you have sub stack, which is awesome. ConvertKit you guys started?That would be easy. I started a year before us.Nathan: [00:16:36] We were 2013, but we didn’t get any real traction until 2015.Sam: [00:16:40] We started around the same time, like, so you guys are big now. We’re big now. And then there’s like the morning brew there’s um, sub stack has made it quite popular. I mean, everyone has an email now and it wasn’t like that just three or four years ago.Nathan: [00:16:54] we can get into how I feel, but I’m curious how you feel of it. Being the first, like starting an email newsletter when everyone’s like, it’ll never make money. It can never be a real business, you know, or something like that. And then you’re trying to convince people of that. And now like the wave has come or the wave is here and everyone’s like, I’m starting a newsletter.Sam: [00:17:15] No. I like, I don’t feel hate like, Jay, I’m not jaded, so I’m not like, Oh, I’m sorry, an email. And I’m like, Oh dude, that was, but every once in a while, someone’s like community and newsletter is like the new media company of 2021. And I’m like dog. That was the media company of 2014. Like we started then.Okay. And like, if like the beta company of 2021 is something that you aren’t talking about. Probably because it seems stupid right now, and it’s not going to seem stupid in five years, but that said, I do like, what’s the, what’s the biggest difference in email over the past 20 years? Is it like the promo tag on Gmail or the promo inbox?Like it’s pretty stagnant, right? It hasn’t changed significantly. Like there’s superhuman and other things like it, but it’s relatively been like. N zero change or close to no change. I have a feeling that’s going to remain the case over the next 10 years. Maybe like some, some small changes will happen, but I still think it’s a pretty safe bet to rely on email.And so if someone says they’re launching it, I say, yeah, I think that’s smart. I would say, don’t copy us. Or like, if you do copy us, like, yeah, you might be successful, but like try something a little bit different. That seems silly now. And then it might be cooler in a couple of years.Nathan: [00:18:28] Does it annoy you since you have a paid publication called Trends? That there’s another free publication called Trends, but itSam: [00:18:38] Oh yeah. I emailed that guy and I was like, Hey man, like Sam: [00:18:43] Was like, we’re, I think we’re going to make this big and I don’t want to disrespect you, but do you want to change your name? we, I was like, we did start first and we are bigger. Like we’re going to, I think we’re going to make this thing big.And he wasn’t having it, but that’s okay. No, I don’t annoy meNathan: [00:18:58] I’m curious for more of those things, you said it’s harder now cause of the competition. Sam: [00:19:03] And to acquire customers. So we spend money on advertising to acquire customersNathan: [00:19:09] What are you spending now too? Like to acquire a subscriber?Sam: [00:19:12] It ranges. I mean, we have all these new sources that we never even knew about, but like on Facebook I remember on Facebook four years ago, it was like a dollar now it’s like three, Nathan: [00:19:23] Yeah. Sam: [00:19:23] Or four, maybe, maybe four, but we use all these other sources and we can get them for way cheaper.But like, we built those, like, that’s that those source, although finding new sources is that’s kind of like people think of you have good content. You’re going to make it. It’s acquiring users is it’s like, is as important as the contentNathan: [00:19:42] So like, what are some of those other sources that, that are working now?Sam: [00:19:46] So we do a lot of this thing called co-reg. So let’s say that, and we work with like literally a hundred websites. So let’s say that you, you go to a website to, to apply for a tech job. Or yeah, to apply for a tech job, you apply for a job to work at Facebook. And then after you sign up for Facebook and submit your resume, it says awesome.By the way, while you’re waiting, do you want to sign up for The Hustle as well? Just click here. We already have your email, just click here and you’ll get that your first free daily email. so we do things like that all the time. another thing is if you look at product hunt, so product hunt has the same thing as well.Product hunt has your email and you’ll see The Hustle or trends on there listed as a product. And it’ll be like, do you want a free daily email? Just click this button right here. And boom, you’re you’ll have it. So sources like that, we call them. co-reg co-registration so someone who’s already registered for product hunt.They just click a button and then they’re automatically registered for us at The Hustle. Now that stuff is not nearly as turning, like click and play or whatever as Facebook, you actually need to build out some stuff in order to make that possible.Nathan: [00:20:53] So is that something that you’re getting you’re paying per lead on that, like, you know, aSam: [00:20:59] Yeah, but you can actually do it a little bit differently. You could pay, pay per lead, or if you’re, if you’re, if you’re spending a fair bit of money, like tens of thousands or hundreds of thousands of dollars a month, you could tell them I’m only going to pay you if this subscriber is a power user, so I’ll pay you a dollar, but only if they open the email.At a 75% open rate for the first 10 days.Nathan: [00:21:22] So you’re guaranteeing success, not, not long-term, but at least, you know, midterm and not like a bunch of bots signups or whatever else.Sam: [00:21:30] Exactly. Yeah. Yeah. And that that’s quite effective. I think that stuff has always air has existed for years, but it took us a long time to like, learn how to do all that. when we’ve launched. Like there was companies doing what we have been doing. Right. There’s the Daily candy. There was Thrillist, there was Motley fool.And there probably was literally hundreds more that I don’t even know that they exist. So I don’t want to act like we invented this, but in a sense, we did kind of invent it because I didn’t know how anyone did it. And there certainly weren’t enough to show us the way. So I’m sure that when I say we invented, we came to probably the same conclusion that many others did, but we had to learn all this on our own.Like there was no one to teach us and. We’re now probably one of the, like, it’s us, the skim and morning brew. We’re probably the biggest. And so like, we can learn from each other, but there really wasn’t that many people teaching you how to do any of this stuff.Nathan: [00:22:22] Yeah, that’s interesting. What do you think about. Like people running these largest newsletters that are, publications versus someone like James clear who are you know, running a million subscriber email list as an individual, like what what’s different on growing one versus the other of the tactics that you try.Sam: [00:22:41] Not that different. I mean, there it, doesn’t James Clear use you guys like, he. W H he has like a four-person operation or it’s like a small operation, right?Nathan: [00:22:51] Yeah, I think it’s just him and I think two employees,Sam: [00:22:54] Not that different. I mean, there is one big difference, which is like, your life sucks. If you’re like, I used to, when we started, I was the writer, Nathan: [00:23:02] Right.Sam: [00:23:04] And I was the growth marketer and I was the admin and I did the accounting, which wasn’t good. And I booked the office space and I recruited people.And when you’re doing that for a Daily email, it’s sucks. It is really hard. It’s hard, hard, hard, hard, hard. and so it’s, you know, in order to create an asset, that’s sellable people have to be interchangeable, right? Because you don’t want to, like, if you’re going to buy, like, can James Clear ever sell James Clear maybe, but it would be really hard.Nathan: [00:23:33] Yeah, it’d be kind of weird.Sam: [00:23:35] Yeah, it would be weird. I mean, like James Altucher just sold it and, but he eventually had to like hire people. So it’s, it can be hard. It’s hard to sell something that’s just based off of one person and it’s hard work. It’s really hard work.Nathan: [00:23:47] Is that something like I’ve gotten this feeling of when you were traveling around and everything that you’ve done? Pretty good job. At least of being one step removed from the day-to-day operations of the Sam: [00:24:00] Yeah. So before, right before we sold, I hired us. Like I, I had, I sent an offer to a guy to become the CEO of the company.Nathan: [00:24:07] Okay. Sam: [00:24:08] And then I got the offer and I was like, Hey man. I got the software. I have to take it. So I had to rescind my offer to him and he was cool about it. And we’re still great friends and we’re gonna work together somehow.But yeah, I’m the type of guy who I like to start stuff and then hand it off.Nathan: [00:24:24] But then, I mean, at that point you’re still four or five years into The Hustle before you hired for that role. Right.Sam: [00:24:30] Yeah. But I should have hired from that role earlier on, but I always hired people. Who were like pretty good at what they did. And I was always hands-off, like I would be in every meeting I would participate, but like our sales team, like I had, I sold the first $150,000 worth of advertising. And then once I hired someone, I literally had never sold again and I completely stayed away.And I just said, all right, guys, let’s agree to some revenue targets. And they go, all right, cool. here’s what we think we can do if you can get us to grow this much. And I go, all right, cool. See you go do it. And then I will go to the grow team and I would say, Hey, we’ve got to grow this amount in order to hit these targets.And they would say, all right, we can do it. See you. And then if, and if either of those teams, didn’t hit targets or were struggling, they was say, Hey, we’re, It’s not looking good. We need your help. And I would just drop in and see what I could do to help see if I can make an introduction to some person.See if I could come up with some creative ideas, see if I could use my personal brand to like, promote something, things like that. and then whenever we wanted to launch something new, I would always, I would lock myself in a room and do it almost by myself. Like when we, so trends, trends was almost going to be like, we were on track to have like close to an eight figure subscription business.Nathan: [00:25:42] Wow. Sam: [00:25:43] The first $50,000 in pre-sales I got from Gumroad, I got ungovernable on my own and I would literally call the customers and ask them, why did you buy this?And so I did all the early product stuff, and then once we show that it might be a little work, we had people at our company who are significantly more talented and skilled at running it.Nathan: [00:26:05] So that that’s it. It’s interesting of like, Start something. So it’s like the tip of the spear. And then as soon as possible, hire someone to run it and then just basically like understand their goals and otherwise leave him alone unless they need help.Sam: [00:26:17] Yeah, I think that like you, how many people work there at 50?Nathan: [00:26:22] Yeah. 60.Sam: [00:26:23] Yeah. So you guys have been a fair bit bigger than us, but we, I think that, most people, most humans, not my company, but human being suck at starting stuff. Right? Like it’s really hard to give someone a blank piece of paper and tell them, create magic, create something cool. It’s really, really hard for a lot of people, but you know, you, you, I I’ve been reading your work for.Almost 10 years or eight years now, whenever you launch authority, like guys like you and me, I don’t know if it’s something you’re born with or if it’s a skill that you just get my muscle, you’re just kids get used to flexing, but. Like, let’s just focus on our strengths and most people are not that. And it’s not to say one’s better or worse.In fact, they’re both important because without either you don’t create anything meaningful, but if most people are not good at this, and if you have one person who is, then it’s just like go all in on that and focus on creating new stuff. And that’s kinda like what we did. because someone like me who would try to run something on a day-to-day basis, not only would I be bad at it, I could ruin it. If a company gets add, it can be, it can be ruined.Nathan: [00:27:35] Right. That’s interesting. I’m noticing. Like, I’m good at starting things, but I’m not great at handing them off. And so I’m like following your playbook. Exactly. Except I’m staying involved, which is a pretty key difference in the playbook. And so that’s the transition that I’m making right now.Sam: [00:27:52] Well, you’re a perfectionist. I mean, I’ve known you for a while. Like you’re, you’re a craftsman. Like from your Airbnbs to, like I could tell, like from your background of this, of this, zoom call, like you’re a craftsmen. And I think that being a craftsman is, is a blessing and a curse. It’s a curse, or it’s a blessing in that.Like everything Nathan Barry makes is like pretty awesome. And I want to be, I want to see everything he does. It’s a curse because it’s like an exhausting, it’s like an exhausting place to be in because you probably don’t let too much slide.Nathan: [00:28:22] Yeah, so, I mean, now I’m trying the approach of like, instead of hiring people and training them up, I’m like hiring people who have done it all before. And so. we just hired like the, director of design from mozzarella on Firefox to run, to be our VP of product. And we just hired a senior exec from MailChimp to be our VP of engineering and like just filling in roles in that way with people who really know what they’re doing, we’ll see how well it works out.But I think so far it’ll be good.Sam: [00:28:53] So someone taught me that same thing. And so when we hired people, you know, you can’t afford anyone at first, so you can only afford someone who’s willing to work for 40 grand a year. And that 40 grand a year a person is probably pretty smart or high energy or, or real, but really inexperienced. Or some combination of all those, you know what I mean?Like you, so you can like, you have to pick like, you’re smart, but you’re unskilled or, you know, you have to pick like, like two of the three and then it’s like a blessing once you get big enough.Nathan: [00:29:27] You grab the skill, but you don’t have driver.Sam: [00:29:29] Right. And so you’ve got to like pick a choose, like who can, you can hire for $45,000 a year. And then, once you get big enough, Andrew Wilkinson, who I’m sure, you know, Nathan: [00:29:39] Yep. Sam: [00:29:40] Taught, he was like, man, Because I was like, Hey, I’m thinking about hiring the CEO.And I showed him this role. And he was like, but this person has never done it before I go. Yeah. But like, they built this other company. That’s like, it’s a software company and that’s kind of cool. And like, they’re really smart. He goes, no, no, no, no, no, dude just go find someone who’s already done this before.And I was like, why? And I wanted to get like cute and creative. I’m like, Oh, you know, he could apply this. He goes, no, just get someone who’s done it all of this before. It’s way easier. Like if you’re gonna get a mechanic, do you want a mechanic? Who’s like, Been a good electrician before? Or do you just want someone who’s a really good mechanic, like just get a good mechanic, like someone who already knows what they’re doing.And I did. I agree with you, that’s the way to go,Nathan: [00:30:18] Yeah, that makes sense.Sam: [00:30:20] But like, you want to get cute, right? Like you want to get cute and like find unique ways of going about it, but maybe that’s not necessary.Nathan: [00:30:28] Well, I always want to think that all the rules and best practices don’t apply to me, you know, like I can figure out some way around it or like, I’ll train this person up in some way. And I like to give everyone lots of chances, which has resulted in some amazing people that work on the team. but then it’s also hard when you get to this level, especially for like manager and executive roles where it’s just like, Now I’m fully in that higher people who’ve done it before camp.Sam: [00:30:55] Yeah, it’s just way less headache.Nathan: [00:30:56] Okay. So I’m curious, there’s on the writing side, was that a hard thing to hand off or was writing something easier? Cause I think a lot of newsletter creators, you know, they start writing everything themselves, and they have this really close attachment to it. And then that’s the biggest hamster wheel.Right?Sam: [00:31:17] It was a little bit, so if anyone ever wrote anything and they may put my name on it, I would say I have to approve it. You can’t send that out because sometimes people would write like, like a re-engagement email. So if someone’s quit and they would write an email from my name, because it would get a higher open rate just because when you have a name on it and I got really mad, I was like, you guys.I’m so thankful you took initiative, but if this is my name, You’ve got to tell me about it. How would you like it? If I said, Hey, you know, I’m just making, I’m just making this up. This isn’t true. Hey Steph. by the way, I just told all these people, you just said this you cool. so I was like, so that was a challenge setting boundaries, but, handing it off.It was yes and no, because like, I’m not saying this is the reality, but I felt I was the best. So, I felt my perspective is about, Sam: [00:32:06] yeah, and it’s, it’s actually not true. Like we’ve actually hired people that are way better than me, but I, so I thought I was the best, but I didn’t like it. It’s really hard.Writing is hard. It’s a hard work. Like when you’re writing your book, like you want to kill yourself while you’re doing it, but afterwards you’re like, yeah, this is awesome. It’s finished. It’s exact, it’s still, but imagine doing that every day.Nathan: [00:32:28] Writing is one of those things that I feel like only I could ever write in my voice or in the style that I like or something like that. And then I’ve worked with some really good editors and they take some of that. Right. And then add a whole bunch to it. And it still sounds exactly like me and I’m like, Oh, Okay.So when a professional comes in, it’s a different game.Sam: [00:32:47] I can write like you, I know how you write. I like it. You and I can, we can Write somewhat similarly. but I think I could write, like you I’ve read, I’ve read it so much of your work that, do you know, what do you know what copy work is?Nathan: [00:33:01] No, I don’t.Sam: [00:33:02] So it’s when you, they used to teach us in the school years ago and then something changed in how they thought people learned and they quit doing it. But basically a great way to learn how to write is you take other works. And you just copy them word for word. It’s kind of like what you learn, how to play an instrument.You know, you don’t like write your song right away. You typically play jingle bells and then you figure out how to play. Like some song you like, and then you like learn how to play. Like, you know, you copy like green day and then you copy foo fighters. And then after you doing that for five years, then you like, Write your first rock song.So that’s how I learned how to write is I copy other people’s work and I would copy your work I would copy. A lot of people’s work, any author that I, I thought, like had a really sharp tone of voice. I would copy it out by hand. So I’ve copied some of your stuff. And so like, if you do that a little bit, you can, you can learn how to write just like them.Nathan: [00:33:51] That’s fascinating because I would do that with design, where I remember when I was first living in design, you know, you didn’t have any clients or things like that. And so I’d just be looking for something to design because you didn’t want to just follow the tutorial. You needed more than that. And so I’d find a website that I loved and I would just go recreate the whole thing in Photoshop.Sam: [00:34:10] It’s it’s it’s I think it’s the most effective way to learn. Like, do you realize how, when we do your kids play any instruments or they’re too young?Nathan: [00:34:16] I’m just trying to get them started. I actually took up playing piano, 80 days ago to try to inspire my kids, to play the piano andSam: [00:34:24] Oh, awesome. Nathan: [00:34:26] Like he had no interest in playing the piano and then like about 45 days of me practicing every single day, he like is hanging out in the other piano and then he’s doing it.Sam: [00:34:37] Do you know how to play anything.Nathan: [00:34:38] I can play. but he, he got me back by playing baby shark on the piano and I wasSam: [00:34:43] That’s awesome. So like, you learn how to play the piano in 80 days. That’s pretty remarkable. Right? And you maybe aren’t great, but at least you could play something. Nathan: [00:34:54] Yup. Sam: [00:34:55] And it’s the same with writing. So I think you can take someone who’s bad at writing and make them a little bit better or a lot better in a very short amount of time by doing this.Nathan: [00:35:03] That’s interesting. So basically find. Five 10 writers that you really enjoy reading. You love their style, or even maybe their style is completely different and you want it to use it to stretch your own ability. Sam: [00:35:16] Yeah. Yeah. So for example, do we have anything up here that I’ve done copy work with? So, I don’t think I have anything. So like, what’s the guy’s name? Who wrote the book? Thompson. What’s the, what’s the guy’s name? Who’s like the, a drug addict writer, um, who wrote like, um, why can’t I think of it, the guy who wrote about the hell’s angels and going to Vegas and do drugs, Sam: [00:35:43] Hunter S Thompson.Nathan: [00:35:44] Okay. Yeah. Sam: [00:35:46] Okay. So his writing is like kind of interesting, and I don’t really want to write like him, but I want to learn what makes his writing special. So I would just write that novel out or, J D Salinger, wrote Catcher in the Rye kind of like kitty kind of a kid’s book. so very simple language, but pretty interesting storytelling.So I learned how to, I would have copy of that book and then I would learn how to, I really wanted to learn how to be a good copywriter, a good sales person. So I would take old advertisements, long-form advertisements, and I would copy them word-for-word And so I start learning like, all right, wow.This here’s how you sell. Here’s how you storytell. Here’s how you use simple language to describe complex topics. or let’s say you want to learn how to write comedy, so you can just literally write out a script from a movie, Judd Apatow. Does this all the time, or he said he did. He, what’s the guy’s name?The Jewish, director from, New York who wrote, who wrote penny, uh, frickin, Andy, what’s the guy’s name. He ended up dating a stepdaughter.Nathan: [00:36:50] Oh, I, I don’t, I don’t know. Apparently I’m bad with names.Sam: [00:36:53] What’s the kind of same, it’s the same. Everyone’s gonna be like, be scrap. Everyone’s gonna be screaming this, but he’s like, anyway, Annie hall, the guy who did Annie hall, what’s his name?It’s going to kill me. Woody Allen.Nathan: [00:37:10] Woody Allen. There we go.Sam: [00:37:12] What do you out? The guy who, so Judd Apatow wanted to be like Andy, like Woody Allen. And so he just got a bunch of Woody Allen scripts and you just wrote them out word-for-word or he also wanted to be good at writing sketch comedy. So he took Saturday night, live skits and wrote them out word-for-word It’s a very, very, very effective way to learn how to write,Nathan: [00:37:29] Yeah. And would you re type them or are you actually writing them long form by hand?Sam: [00:37:34] Keep them right here. So I have like, I don’t have them here right now. I have, Big old stack of notebooks. And I wrote them up by hand and I still do thisNathan: [00:37:43] Do you think that that helps, you know, you pick out patterns and all of that versus typing?Sam: [00:37:49] Verse. Yeah.Nathan: [00:37:50] Yeah. I mean, obviously you do, if you’re Day, if you’re putting the time to do it,Sam: [00:37:54] No, I think handwriting was better because you could, you hand write slower than you type. You can type a lot faster than you could hand write. So it’s a forcing factor to keep you slow. you know what I mean? And so it’s like maybe now that you’ve learned how to play simple music, I don’t know if you have gotten to this level, but you’ll be listening to the radio and you’re like, Oh wow, there was a chord change or, Oh wow.He’s using like the, the ACD chord structure. I don’t know anything about music. I’m making this up, but you know what I mean? Like maybe you like start because you’ll have figured out the texture, you start seeing that out in the wild. And you’re like, Oh, I just unpacked it. That’s how they made this unpopular.They did this thing, you know what I mean? And so you could do that with good writing. And now if you learn how to write well, you’re like, Ooh, you see how they, their opening line, like, cut straight to the story as opposed to doing this, this and this, or they’ve described this or the rhythm of their sentences has changed dramatically.And they did that to make you feel X, Y, and Z, or this person’s writing at a fourth grade. Reading level, but they are describing like what, what it’s like to be floating around in space in the universe and wondering what’s men’s ma what’s man’s purpose and office like a complex topic, but they’re writing, using syllable words that don’t have more than three syllables.And anyway, it starts when you start seeing that, I think it’s pretty cool.Nathan: [00:39:17] Well, one example that I can think of is. I would write a lot from my own experience for the most part. But then you get to a point where you’re trying to pull in examples, you know, of like, here’s how this creator, you know, grew their audience or build a business with these other things. And I would always share examples.Like I could only do a few examples per piece because if I wanted to talk about someone else, it took me like three paragraphs to introduce who they were, talk about them and like make my point with their story. And then I’d read Ryan holiday and he would in a single sentence. Like he has his points and then he would introduce someone you like make a point and move on in one sentence.And it like, as readers, just as engaging as what I was, or like communicated just as much as what I was saying in three paragraphs. And so I remember, it was obstacle is the way it was his book where I would like go back and be like, wait, what, how did you communicate that much so quickly? And that was one that I started copying his style on directly.Sam: [00:40:16] Yeah. And it’s, you could learn that really quickly by just finding the segments that he did that and literally writing it out by hand. And if you do it like 10, 20, 30 times, it can become a learned behavior relatively easily. VR, because writing can be like everyone. A lot, many people think they’re bad at writing and it’s like a pretty.Like you don’t need to think that much in order to get good at it if you use this tactic.Nathan: [00:40:40] Yeah, that’s interesting. Are there other areas of your life or business that you apply that tactic?Sam: [00:40:45] Yeah. I mean, like, I think that, like the goal is basically to remove a lot of emotion and a lot of like decision fatigue out of learning a skill set. So like, if you want to get good at something like you try not to, the goal is ultimately to just copy what has worked in the past. So you can actually get good at the exercise versus thinking about what exercise you should do.And I do that with writing and then I also do it with extra, like literally working out. So like, if I want to get, if I go, if I want to run fast, I like to train to be a sprinter. I was a sprinter in college and I still like to do the training. I always hire a coach and I say, make a plan for me. And so all I think about is showing up to the track and getting the work done as opposed to deciding like what I need to do.I do that with weightlifting. I like, I have a personal chef, which sounds bougie, but it’s not that expensive. and so like, if I want to lose weight, I’m just like, alright, I need to eat 1800 calories a day. Just do it so I can grab it and eat it. So I like to do whenever I have a goal, I like to remove as much.I like to put blinders on. And, and so I kinda, I, I, it’s a little bit of a similar process as copy work.Nathan: [00:41:54] Yeah, that makes sense. yeah, cause I think on so many of these things, it’s, it’s just about doing the work consistently. Like I, or I was talking about talking to my brother-in-law about weightlifting the other day and just how. You can kind of, it’s not that you can do whatever, but you kind of just need to pick a religion and stick with it rather than like debating the pros and cons of, you know, every different method.Sam: [00:42:20] Do are you trying to get strong?Nathan: [00:42:21] I w I would like to, I haven’t been to the gym. Sam: [00:42:24] Can I brag really quick,Nathan: [00:42:27] I saw on Facebook, can I break for you?Sam: [00:42:30] Dude? That I was working to do that for a few months. I finally hit it. So I hit the 1100 about the 1100 pound club. And do you want to know something crazy? I mean, I’ve been exercising for a long time, so, I don’t know if you have or have not, but it’s definitely an unfair advantage if you’d been doing it for a long time, but I filed the five by five plan.You know what that is? Nathan: [00:42:49] Yeah. Sam: [00:42:50] It was the best I got. I got so strong, so fast. All it is is five sets with five reps of bench, squat and deadlift. That’s pretty much all it is. You could do a few other things, but that’s basically it. And you do it three days a week and it takes about 45 minutes and it seems fairly stupid and repetitive.And it made me very strong. I highly recommend that.Nathan: [00:43:12] Yeah. And so for anyone who doesn’t know that the thousand pound club is, would be the, the milestone that most people are trying to hit. Those three weights or those three lifts adding up to a thousand pounds.Sam: [00:43:22] Yeah. The next goal, I don’t think I’m going to do it because I don’t think you need to have big muscles to like, like my goal is to live to 120 and just be able to be healthy. You don’t need to have big muscles to do that, but I think the next goal is going to be 300, 400, 500. So it’s a 300 pound bench, which I did the other day.So I don’t need to improve that a 400 pound squat, which I can do almost. And then a 500 pound deadlift, which I can’t do. And so three, so how much would that be? That’d be 1200 pounds. so that’s like the next thing. And I think you can do that just by doing five by five. It’s like an, an incredible routine that whoever made it up, it’s very effective.Nathan: [00:43:57] Yeah. Mark. B, everyone listening to this is going to be like, you guys don’t know the names of a single person, but that’s okay.Sam: [00:44:08] What’s a guy named Mark Texas. Is that his name?Nathan: [00:44:10] Now it’s, I think Starting Strength is the book and anyway, it’s not important. That’s what everyone has to do before.Sam: [00:44:18] Yeah, sorry. We’re like I said, like, you know, that director, so, and I, Can I ask you,What do you think is going to change about email?Nathan: [00:44:27] That’s a good question. Well, the fact that I don’t have to tell people that it’s a good idea to do email anymore. Like, that’s, what’s nice about what has changed because, you know, three, four or five years ago people were like, yeah, that’s great. But like isn’t email dead or something. And now everyone’s like, email is the greatest thing.And so that’s fun. Sam: [00:44:47] Can I give you an analogy to use for that? Nathan: [00:44:49] Yeah. Sam: [00:44:50] So here’s what I tell people. I go email is like your pirate ship. And every new subscriber is a little bit of wind in your sails.Nathan: [00:44:57] I like that.Sam: [00:44:58] You can steal that one when you’re trying to explain why email is important, but sorry, go ahead.Nathan: [00:45:03] We’ll be off, you know, marauding on the seas. What I think is going to change is I think that one of these email, whether it’s a Hey or superhuman or one of those we’ll, get enough traction that they could actually change how we interact with email.Sam: [00:45:22] It should. Nathan: [00:45:24] I think we’re still quite a ways off from it, and I don’t necessarily think it’s going to be any of those, like those that do it.I used to think it would be Gmail. but now I’m not convinced that like, it’s not going to be Gmail. the ship has sailed on that. Like if they were going to do it, they would do it with their inbox product and they didn’t. so that’s the first thing.Sam: [00:45:46] Wait, can we talk more about that? So like, so to anyone who doesn’t entirely understand what he’s talking about, basically like Gmail Day never has never evolves. Nathan: [00:45:56] Right. Sam: [00:45:57] You New, you can’t. They they’ve evolved a little bit. They, what’s that called accelerated mobile pages. So amp amp, you can, they have amp and email, but no one uses it, but it is pretty nifty, but no one uses it.But basically like in your email, you should be able to buy stuff or you should be able to, like, you should be able to see a video or you should be able to swipe, or I don’t know what else,Nathan: [00:46:23] Well, so a bunch of that is coming. Like we’re building video in email right now and it’ll. just have fallbacks, it works on most Apple devices, or it works on all Apple devices and a lot of other ones, and we’re just building it where it has all the fallbacks, so that, on like the crappiest version of outlook, it would just be the like click the image or click the animated GIF is what it’ll be and it opens.But then on, you know, your iPhone or Apple mail or, even in some cases, Gmail, it’ll play the video in line.Sam: [00:46:58] How, so when I say video in line, we’ve always just used GIFs. I thought it would have been cool to like put in a GIF, like part one, and then make the user hit, refresh to see part two.Nathan: [00:47:09] That can work. so basically HTML5 video is a lot more supportive than people think it’s just no, one’s willing to do the work for all the fallbacks. and, and so it’s not actually, like I dove into researching it. actually there’s a company called tailored mail. that said they had it and I was like, that’s nonsense.Sam: [00:47:31] A lot of people have said they have it. Nathan: [00:47:33] Yeah. And I dove in and realized like, Oh, it’s actually like, you can’t get it perfect. But you can get it pretty close. and, and there’s a whole bunch of work to it, but I think a lot of that will get better. Sam: [00:47:44] If that exists. I think that will change. That might change storytelling because if you’re like the New York times, you don’t need a website ever. And you could tell story in someone’s email or like, You can send live alerts about a breaking news story and like have a live video in someone’s email. And I think that’s like really, really, really quite revolutionary.Like I’m not even being sarcastic like or hyperbolic, like that’s legitimately it will change how someone receives information.Nathan: [00:48:15] That’s fascinating. I didn’t think about like a live video. Because obviously, if you can do video that you can do live video. but I didn’t think about the implications of that.Sam: [00:48:25] Well think about it. Most people’s emails are static, right? They send at the same time every day. That’s not how it should be. News doesn’t happen at the same time every day. So if you’re following, if you have a, you, you bought a local publication, right.Nathan: [00:48:39] I’m building one. Yeah.Sam: [00:48:41] Like if you are in Boise and it’s like, there’s a shooter in Boise. Like they got to tell people right away. Or if like the election results for the mayor of Boise, like it’s coming down to the last minute. We’re actually here now where, you know what I mean? Like that’s pretty phenomenal, I think. And they should like have that in real time.Not at 8:00 AM every morning.Nathan: [00:48:59] And they’ll, you know, use email to push things out. One thing that I think is really interesting is using. server generated images to change the content in an email. Write Sam: [00:49:11] That’s what I was describing yet. Nathan: [00:49:13] Yeah. So like, countdown timers are the most common example. We’re about to roll that out natively and ConvertKit, but what’s actually cooler is when you’re doing things like, like shipping status or something like that, and it keeps changing in the email.Cause that’s just an image that they’re generating off the server. I just wish you could do it in an accessible way.Sam: [00:49:34] I think that that’s exciting. Like, I mean, it seems kind of nerdy when you’d like to talk about it like this, but I’m like, no, I like the implications actually can be pretty big. Like if it could be, because what ConvertKit and other people are doing, like you’re building the Legos and then maybe like someone like me who likes to put Legos together, like you’re giving me these new parts and I’m hopefully going to turn it into some amazing art that you didn’t even know that you were intending to use it for.And that’s cool.Nathan: [00:50:00] I mean, there’s other things like, I don’t think this is in any other platform, but for the longest time, if you sent out an email and you click the link and it’s broken, then you hit reply and you’re like, did you just email the million people with a broken link? and one thing that we realized is that link hits our servers.And so we can actually let you edit the link after the email has been sent. And so I don’t think any other tool is out of that yet, but when you like obsess over these problems enough, then you canSam: [00:50:28] But you want to know something funny that, that tactic of emailing the wrong link and then emailing them again to let people know that you’ve fixed. It always gets moreNathan: [00:50:38] Oh, it does. Okay. You should tell everyone about your black Friday.Sam: [00:50:43] Okay. So I’ve done this twice. Most people don’t know I did this twice. I actually did this in 2014. When we first started, when we only had about 40,000 subscribers. So back then in 14, what I did or 15 or no, when we launched, we launched at 16. So I didn’t tell him 16. I’ll tell you what I did black Friday, and I’ll tell you what I did now.And, or back then. So back then I, we accidentally sent, like, it was, the day was Thursday morning. We accidentally sent the previous Wednesday’s email on Thursday. And so people got like the same one over and then we immediately sent a reply. And it was a screenshot of my Slack, where it was me slacking to our writers saying like, you really screwed up, you know this.Right. And then being like, Oh my God, I can’t believe I did that. It’s like, and she’s saying like, well, what do I do? And I’m saying, you better fix this or you’re out of here. And she was being like, well, you gotta give me some suggestions. I go, yeah. I don’t know, just take a screenshot of this and put it in the email.And if it gets a lot of opens your to keep your job, if it doesn’t you’re out of here and we just screenshot of that and put it in the email and it got the highest open rate and a lot, some people didn’t get the joke and they got mad at me, but I was whatever. but the other day we made like $800,000 in one day.And what we did was, This, this is like what I’m saying. Like you, you ConvertKit creates the Lego pieces and it’s fun for us to manipulate it to great, cool stuff. We, made an email, which is actually really hard to make an email look like a Gmail email. it’s like not intuitive and you’ve got to like, kind of do weird stuff, but we made an email look like a Gmail email.And we made it look exactly like I was having a conversation with the team and I sent them an email. It said art, everyone are big black Friday sale. It’s totally ready. Can you guys please make sure all the links work? um, this is going to go live and it’s actually like our biggest discount ever. I’m kind of think that we’re giving too big of a discount, but, whatever, I guess we’ll see what happens.Just let me know if it works and then we’ll and we’ll hit send tomorrow morning. And then they reply. And so that email, it was sent to a million plus people or something like that. And we made it look like it was, it was an accident. You know, I accidentally sent it to our whole list as opposed to our company.And we got so much traction so much, there was tens of thousands of people on the website buying. And I got literally 10,000 emails and we send it from Sam at The Hustle up my personal email. I got so many subscribers people saying, including my friends like Nathan, or, Andrew Wilkinson, like smart techie, entrepreneurial friends being like, they called me and they go.Yeah, they go, dude, you just sent this out to your whole list. This was not meant for, this was you were not meaning to send this to me. And my reply was like, Oh no, really? And, it just crushed it. Yeah. It was like the biggest sales day ever. I think we, I think we stole that idea by the way, I’ll give credit.I think it was Chubbies who I stole it or Brooklyn and we stole it from someone, but it was really effective.Nathan: [00:53:48] Yeah, that’s amazing. I just love the idea that someone receiving that email would think that, like there’s another email address of like entire list@thehustle.com or whatever they’ve you send to that? It. Like, I love that someone thinks that’s a mistake that could actually,Sam: [00:54:02] The people at HubSpot emailed me. This was during our due diligence. And they’re like, Hey, like they called me or texted me. They’re like, I don’t think this is meant to go to everyone. And I was like, Oh my God. I know it was a joke. It was a hit, it was a huge hit. It was great.Nathan: [00:54:18] That’s amazing. I’d love to talk just for a few minutes about monetization and, and, any of that since you have this split between sponsored revenue and, and the paid revenue and all that, maybe share some of the numbers behind trends, at least at the highest level that you can. And then, I’m curious why, why you keep those two models?Sam: [00:54:40] So when, We were, we were probably going to do 20 million in revenue in 2021, Nathan: [00:54:48] That’s amazing.Sam: [00:54:49] Independently. but now things changed, you know, we’re owned by a $20 billion software company and they’re less interested in our revenue and more interested in the revenue we can create for them as a New, you know, cause their hotspot only has like 100,000 customers and they do a billion in sales.So they’re like, yeah, we don’t really care about 20 million in revenue. That’s cool. And all, but can you help us drive like 5% more customer base? Because that’s like a huge jump for us. but, and I just made all those numbers up by the way, except for the a hundred thousand that’s public, but don’t, now that we’re owned by a public company, I gotta be careful what I say.You know, I’m not saying the customer base is going to jump by 5% or they even want it to, I’m just making that up for argument’s sake. so when we started the business, the goal was to build up this massive email list and build trust, and then create profits early on with advertising and then use those profits to build stuff, for the audience.And I think you actually had that wonderful blog post called like the billion dollar blog.Nathan: [00:55:52] Yeah. Yeah, exactly.Sam: [00:55:53] Is that what it’s called?Nathan: [00:55:55] Yeah, it is.Sam: [00:55:56] And you were like, there’s a lot of companies that started as a blog. And then they launched other things. So for example, ConvertKit was kind of like this off of Nathan barry.com. Then there was, um, what’s the makeup company in New York.Nathan: [00:56:10] ASam: [00:56:11] Gloss into the gloss,Nathan: [00:56:12] Yep. Sam: [00:56:13] Into the gloss, turned into Glossier. And there was like, you had like five or 10 examples and that’s before I saw your blog post, that’s what we wanted to do. And we were just using the advertising early on to bootstrap, and then we launched trends and because I was researching which products we should make, and I was doing a ton of research and I would send it to my friends and they were like, dude, this is sick.Can you actually research this other thing for me? And, we were like, Oh, maybe this is the product like as research. and then we built a Facebook group for it. And they were all talking to each other about other stuff they were researching. And I was like, Oh wow, this is cool community and research.That’s the product. so the idea was not to be an advertising driven company. It was just be an advertising driven company early on, and then launch trends. I mean, we didn’t know it was going to be trends. We were going to launch something. and it was actually pretty hard to pull that off, but we did a pretty good job.I think we would have built it to a hundred million dollar a year business. If we, if we just waited a few more years or maybe five or 10 more years, but like it’s a pretty proven track record. If you can pull this off and subscription revenues. Awesome. It is really, really, really cool. It is awesome.I used to look at ConvertKit’s, bare metrics numbers all the time to see what your monthly churn was. To try to beat it. And in reality, it’s like, you don’t even compare the two, you know, Content and software, like it’s two totally different things. But I would like, I was just like, Oh, what’s a good churn.Let’s look at ConvertKit. um, but anyway, it was awesome. it gave us a lot of freedom because when you have, what, what do you rely solely on advertising? You can’t say certain stuff and I didn’t want us to be in that position. you know, you. If you say something inappropriate or you say something that not everyone agrees with, they can, they can pull their ad and that’s cool.That’s the Write. but it just stinks that that will hurt you if you’re, if you’re reporting on something and I didn’t want that to be the case. So we pivoted, and it was pretty successful. It was really hard, but very successful. Oh, you asked me to say numbers, trends had, has over 15,000 subscribers.Nathan: [00:58:26] How many of those were from a Black Friday in particular?Sam: [00:58:30] I don’t remember exactly. But that day or that like campaign drove, like he got her thousands of, probably 3000 customers. Nathan: [00:58:40] That’s amazing. Sam: [00:58:42] Yeah. Because 3000 times 300 is nine. Yeah. We, we drove up. Yeah, we drove about $800,000 in sales that day. So whatever that divided by, I think it was 200. It was the price, whatever that divided by 200 is how many we gotNathan: [00:58:56] So what’s like, what’s the breakdown between, sponsorship revenue and, you know, the trends revenue as the like percentage of the company.Sam: [00:59:06] By the time we sold advertising was about, was over, as it was over, it was over a million a month in sales. Nathan: [00:59:15] Wow. Sam: [00:59:16] And Trends was going to be close to eight figures this year. but we counted our revenue a little bit odd. Like when you guys do annual billing, how do you count? What do you call that? Just deferred revenue.Nathan: [00:59:31] Yeah, well, we were on an accrual basis and so we divided by 12 and, and then, uh, crew, a portion of it every month.Sam: [00:59:41] So I hate that because I’m like I have the money in the bank and I could spend this money now. So we would call it net cash receipts because I, so anyway, like we want it to have like cash in the bank, like 20 to 22 million in 2021.Nathan: [00:59:57] Okay.Sam: [00:59:58] I think advertising could have been about 14, 15.Nathan: [01:00:01] So, so is the majority is still at, is advertising, but trends is a kick-ass business.Sam: [01:00:08] Yeah. Cause the renewal rates so freaking high. Yeah. Like our renewal rates really high. And I think we’re, we undercharged Write we’re not going to raise the price anymore, but the reason why I’m not sure what 21 would have been is because we had tested raising, like tripling the price and conversion rates were the same.Nathan: [01:00:23] What do you think about like everyone going with paid newsletters now? You know, so it’s all created and say you’re at 25,000 subscribers or 20,000 subscribers.Sam: [01:00:31] I think they’re making the wrong mistakes. I think there’s the Substack is cool, but I think it’s helping people make bad mistakes. I’ll give a few examples. The first, the first example is pricing. Most people charge way too little. if you’re creating a B2C thing, then I understand why you would want to charge like $5 a month.But if you actually want to make a living at this and provide value, you’ve got to charge more money. Like, most traders typically are bad at this. They think that certain information should be free, but it’s like, man, how are you gonna make a living? If you, if you’re charging $4 a month, like that’s really, really hard.So like charge way more. So I think people need to charge a lot more money. particularly, yeah. Or I would say, yeah, more yeah, 50 bucks a month. Sure. Like I would say like the difference between a person buying 99 a year and two 99 a year. I bet you, those rates would be the same and you just made three X more money.And then the difference between two 99 and four 99 also probably isn’t like that big. So I think you should charge more in not only is charging more good for you as a creator because you get more money and you can put more of into the business, but also people tend to like that stuff more. If they paid money for it, they usually appreciate it more.You know, it’s like if you worked really hard to buy a car, versus if the car was given to you, you’re going to treat one of those differently than the other. So I think people tend to treat higher end stuff nicer. So I think you should charge now. I don’t think this isn’t like blanket advice for everyone, but I think a lot of people could use that.The second thing is I would actually do annual billing only, not monthly billing. so if you could pull off doing annual only put it as like, you know, 20. Five bucks a month, but charge it as two 99 a year. because once you, yeah, I just think that’s the better move and you actually would probably have a far more educated opinion on this, but from Content that’s what I’ve seen.Nathan: [01:02:34] Well, the, I mean, I agree with that because we’ve seen Content on membership sites or sorry, turn on membership sites or Content businesses. Being quite a bit higher than software in general, especially when people are implementing it poorly. And so then what happens is, you know, you’re just playing this churn game.And especially when you have high churn on a $9, $15 a month products, it’s reallySam: [01:02:57] Impossible.Nathan: [01:02:59] And so I exactly what you’re saying of going for a year upfront now, it’s interesting. A lot of people go like buy a year for a discount and you’re saying like, just don’t even offer a monthly price.Sam: [01:03:11] Yeah. Oh, well, if you’re going to awfully offer a monthly price, make it like crazy expensive. So it puts an acre. So it makes the annual a no-brainer.Nathan: [01:03:20] So like 50 bucks a month and, or $250 a year. So it’s like double orSam: [01:03:25] Yeah, only pretty much. The whole goal though, is to get annual Nathan: [01:03:30] Right.Sam: [01:03:31] And we have never done monthly. And the reason why is I went and talked to the information I talked to the athletic, I talked to the New York times. I talked to the Motley fool. I talked to like all of these companies and, and. Pretty much across the board.They were like, we only drive people to animal. And I was like, all right, well, I’m not even going to have a monthly, we’re just gonna get rid of it entirely. like why, why even do that then let’s just cut. Cut that. the third thing I would say is. Have a long form sales page as your homepage. A lot of people will think that they’re the New York times and that they can just make their homepage or the page that they drive all the traffic to make it like a, like give a lot, give away a lot of stuff for free and just hope someone will convert, that, that will work if you’re the New York times and everyone knows to trust you and to get to know you and they know exactly what they’re getting themselves into.I think if you’re like not them, then you should probably have a pretty hardcore. like sales page and I don’t mind, my opinion is not to do freemium. Do you have to pay money to get it? you could do like a one, like we do a $1 trial, which is interesting. but, I would say like, make your homepage a sales page.Like if you go to convert or sub sub sub stack pages, it’s just like a one-liner that. Like doesn’t sell the product. So I think you need like a sales page kind of like your book authority. Like you had a sales page.Nathan: [01:04:55] Well, what I was trying to do. With authority was take the best that I could learn from direct response copywriting, and then bring in design from the startup world and try to merge those two things. Cause like the design startup world, they would be like, no, here’s the buy button. You don’t need any convincing.And the direct response world would be like, it doesn’t have to look pretty, but it’s going to be 10 pages long convincing you everything about it. And I was like, can we just, can we just combine these two things?Sam: [01:05:21] That’s exactly what I do. I totally agree with that premise. I, 100% agree with you and that’s exactly what I do. And, I completely agree with that. and then maybe the last thing is what I would make it, what I would make, tell you to do. If you want to grow a paid newsletter is, on the sales page.What should be your homepage? I would make it. So you have to enter your email to see the next, the checkout page, because what’s the average conversion rate, like 3%, but you can collect probably 10 or 12% of those people’s email and pretty much a hundred percent of the people who gave you their email that were already going to buy.Aren’t going to continue to buy, but now you’ve just created a huge lead list. So you can email them all the time and provide a ton of free value and like sell them on your ideas and your product. And White’s good. And then you get increased your sales significantly.Nathan: [01:06:09] Yeah, that’s good. And then, I mean, that’s where you have automated emails, right there going from the free into paid that’s super straightforward.Sam: [01:06:17] Yeah. So those are some tips I would do to be paid. Also, if you want to be a paid, like have a paid newsletter. Go out and find the scammy stuff you can find. And you they’ll probably be doing a whole lot better than like the people on sub stack. And don’t be scammy. Don’t be, I mean, be ethical, provide value, but try to understand why these scammy people are winning.So for example, there’s a company called the Gora. You know what a Gora is.Nathan: [01:06:43] I do. Yeah.Sam: [01:06:44] So not everything they do is scammy, but they cause they, they own like 30 companies, but some of the stuff is, and they’ve been sold. They’ve been sued for selling like a diabetes cure, which is like a book which like, is like horrible that’s you should go to prison for doing that.Right. and they’ve been sued for it, but they make about a billion dollars a year selling newsletters. And so you have to ask yourself like, okay, even if you don’t agree with the ethics, which I don’t let’s let’s figure out what they’re doing. That’s really good. And maybe apply that to a good product with a high integrity team.And so that’s what I think you should do. I don’t think you should copy people on sub stack because only a few of them are doing that pretty well. I think you should copy companies like, like Motley, fool. No one talks about Motley fool right now. I bet you, they make half a billion dollars in sales a year, or I’m a Gora or James Altucher everyone.James is my buddy. Everyone makes fun of James because he had these scammy looking, ads. I bet that makes like 60 million bucks a year. And I’m not again saying like, go against your ethics or anything like that, but just ask yourself why do some of these people succeed significantly better than these other people who we talk about all the time and try to combine, interesting tactics?Nathan: [01:07:56] Yeah, I love it. Well, Sam, I should probably let you get back to, an evening and you know, all of that. You’ve had a busy couple of weeks, a couple months, really? So.Sam: [01:08:06] Yeah, I’m, I’m happy. It’s over though. I’m happy. I get to hang out with you. Are you, what are you going to do with your Boise publication?Nathan: [01:08:16] I’m going to, well, I kinda want to grow a newsletter again. and so I just said it earlier in this call, I didn’t want to start something from scratch and here I am starting something from scratch.Sam: [01:08:30] How much did you invest to start it?Nathan: [01:08:32] I’m setting aside 25 grand. Sam: [01:08:35] That’s it.Nathan: [01:08:36] Yeah. Should I set aside more? I dunno.Sam: [01:08:39] I mean, if you can get it done with 25 grand dude. Yeah. That’s bad ass. I would’ve thought it would’ve been like a quarter of a million, at least. Are you getting someone full-time on staff?Nathan: [01:08:47] I’m starting with someone. I hired someone on contract, to start, so she’s working on it. Part-time I have like relatively small aspirations for it initially. and I want to get that traction. Sam: [01:08:59] Dude that’s bad app launched this. This is like the, this is like the most baller thing you’ve done. This is cool.Nathan: [01:09:04] One idea that I have, I have no idea if this would work. and so I’m curious for your take on it. I looked at my own newsletter list, right? So for my blog, I’ve got, I don’t know, 27,000 subscribers or something. And like four or 500 are in Boise, which is makes sense. Cause I’ve lived here and grown up here forever, all of that.But I’m curious if we went to friends who have, you know, like 50,000 subscribers or a hundred thousand subscribers and you like did the location search. And it was like they had 800 and Boise or 300. I’m curious if like them emailing and being like, Hey, my buddy, Nathan is starting a newsletter in Boise.That is you’re in Boise. I thought you might like it. One. I have no idea what the conversion rates are. And two, I have no idea if anyone would agree to it, like to actually send it out, but I was thinking about it and I’m like, that would be a really quick way to grow.Sam: [01:09:56] Aye. So we wouldn’t agree to it because it’s a lot of work. It’s a lot of work to attract those 800 people, but I think many others would, and I think it would work. You want to know how I would grow? It is I would write a new article every three days and that would make it like. You know, you’re from Boise, if.dot, dot, and then have like a listicle of like, or, or here’s another thing I would do is I would, I would say the eight stereotypes of Boise and I would have an infographic that like might like, do you have like a Boise neighborhood?That’s like the frat or like the Boise area. That’s like, the hips are one. So, so I actually did this tactic. I had an, I had an iPhone app, years ago, a roommate matching app and we launched in Boston Manhattan. Chicago and four or five other places. And all, I, I had never been to Boston and the way that we launched it was we put the stereotypical roommates of Boston.And when we had us, if you Google, Google my name and like info, you might find it. But we made these infographics. And each there was a cartoon of like the woman who was like the hit in the hip certain area. And I’m like typical roommate of the mission in Boston, shops at blank. while drinking a coffee from X, can be seen walking her pug dog, that with a sweater she got from whatever.And, and the whole point of the thing was to two things. One name has many local vendors from that neighborhood. Cause I knew they would share Nathan: [01:11:23] Right. Sam: [01:11:25] Make fun of in a nice way that neighborhood. Cause I knew everyone in that neighborhood would share. And with their friends, like, Oh my God, this is so us or whatever.And I think if you did like, like things like that, that would actually probably grow faster than if you,Nathan: [01:11:40] Did like the partnership side or anything like that? Yeah, that, that’s interesting. I’m, I’m super curious how it’s all going to go. So, I mean, I started hiring a writer and, You know, we’ll get the initial subscribers and the biggest thing, right. We’ll be getting an editorial calendar and getting everything going, but then I’m curious how, how it will go.I think my goal is to get to 10,000 subscribers by the end of this year for a side hustle. So we’ll see from there.Sam: [01:12:11] Well, that’s good, man. Congratulations.Nathan: [01:12:13] Thanks. Okay. where should people go to, to follow what you’re up to? What do you, what do you want to address? Yeah.Sam: [01:12:21] Twitter does @theSamParr. I am there a lot. Don’t email me. Don’t text me. Don’t I won’t reply, but if you talk to me on Twitter, I’ll probably reply. TheHustle.co is our newsletter and then Trends.co is the trends thing we talked about.Nathan: [01:12:36] Sounds good. Well, it’s always good to hang out and, I’ll catch you later.Sam: [01:12:40] Thank you.

Codie Sanchez runs the amazing newsletter Contrarian Thinking, whose topics include passive income, generational wealth, contrarian investing, and learning from strivers who think big.Her motto is “Question everything and stack income streams”, and that’s exactly what we talk about in this episode. Not just “how to build a newsletter”, but one of Nathan’s favorite topics: how to build wealth!You’ll learn how Codie went from journalist to investor to partner in a fund, and how she runs her 100,000-subscriber newsletter plus other companies besides. Codie talks growing a newsletter from 100 subscribers to 1,000 and beyond, but that’s not all.Tune in and find out: Why Joe Rogan’s deal with Spotify was a huge mistake. Getting people to promote you… without sounding thirsty. How to build an all-star team for your growing business. Whether ads or sponsors are a better way to monetize your newsletter. It’s a great show!Links & Resources Unconventional Acquisitions Zero to One: Notes on Startups, or How to Build the Future by Peter Thiel Joe Rogan Howard Stern Mr. Beast Noah Kagan Marketing & Business Blog - OkDork.com Sam Parr CEO at The Hustle Jonah Goldberg - The Dispatch Charles E Gaudet II » Predictable Profits Contrarian Cashflow Codie Sanchez’s Links Newsletter: Contrarian Thinking by Codie Sanchez Twitter: @Codie_Sanchez Instagram: @codiesanchez Episode TranscriptCodie: [00:00:00] The funny thing about audience is money doesn’t care if people care about you. So capital as a leverage source, doesn’t care about relevancy, your dollar, as long as it stays in the market. And you keep reinvesting will have compound interest. The thing about audience is, it can be a depreciating asset. If you don’t pay attention to it, if you don’t upkeep it just like you would a house, then your audience is going to think that you’re not relevant.Nathan: [00:00:32] Today’s episode is with Codie Sanchez. Now Codie has a fascinating background where she started in journalism and there, she was covering a lot of things in Mexico and on the US-Mexico border. So she has crazy stories from that. And then she goes into investing, right? Like it goes to Goldman Sachs and Vanguard and goes to the whole investing world.And then now she’s in not just investing, where she’s a partner in a fund, what was the investing in cannabis companies, but she’s also running a newsletter, with over a hundred thousand subscribers, which is pretty crazy. And we get into how to monetize the newsletter, how to grow it, her take on the creator economy, so many other things. So it was a great conversation and let’s dive in.Codie, thanks for coming on the show.Codie: [00:01:19] My pleasure. Thanks for having me.Nathan: [00:01:20] So you and I have we talk newsletters and everything, which we will, but first we have a shared love for the same topic, a topic that some people love to talk about. Like we do, and other people dance around and think is weird and awkward and everything else. And that is building wealth. Like you and I both love this topic.Why is it something that you, what about so much on all your social channels and your newsletter and everything else?Codie: [00:01:44] Yeah, well, I mean, yeah, I nerd out about this. It might be just because I’ve been in finance for 72 years, but, more than that, I think if you want to. Control the art, you have to control the resources behind the art. And so I’ve always loved creating, I mean, similar to you in multiple different ways, whether you’re creating a business or a newsletter or whatever the case may be.I like the act of creating and if you don’t have the financial resources to actually do the creative, and then there are all of these pressures that get put upon you, and I don’t think you get control of the art. And so that would probably be one of my main reasons. And then secondarily, I just think financial freedom without financial freedom, you don’t have any freedoms. And so that’s sort of one of the building blocks, I think, crucial for people to get.Nathan: [00:02:29] Yeah, that makes sense. So, one thing that you talk about quite a bit is leverage and finding leverage on, you know, as a tool for building wealth, maybe explain some of your thinking behind that and how you’d like to encourage your readers for your newsletter and, you know, companies you invest in to find leverage.Codie: [00:02:46] Yeah, well, we were kind of talking about this before, you know, I thought I was like brilliant and some of these ideas, and then I realized that like the internet also now has caught up and some of this stuff is more normalized, but, You know, when I thought about leverage, I thought about it with four parameters.And that was first you had labor, then you had capital. Then you had code. Then you had audience. Now Naval Ravikant talks about the first three. he doesn’t mention the fourth and the fourth I think is really, in my opinion will be sort of the next frontier, the creator economy, and leveraging your audience in order to get different revenue streams.Because audience is really fascinating in that it’s like an annuity, meaning that it can cashflow consistently, but instead of annuity—only having one revenue stream, you know, they pay you out based on the investment that you make—audience can have have a billion revenue streams. And so anyway, when I think about leverage, I don’t think about it as a financial way.Lots of people think about leverage. Like you loaned me a dollar and I take that dollar and go do something else with it. but the world we live in today that was old school leverage, you know, that was the leverage that created. Basically the biggest Titans of industry in the US: the Rockefellers, the Rothschilds—they were all created right after banking was established.So the banks came out, capital was created. These guys made a ton of money, and then you had code come out, software, right? Robots in the form of software and the next biggest billionaires were created. That’s the Jobs, that’s the Elon Musk, etc. And now in the next realm, I think those with audience will be the next sort of wave of billionaires that are created.And they’re all enabled based on code to some degree. but I think that’ll be the next evolution. So if you are able to understand leverage in a modern day format meaning not just human capital, the most inefficient form—labor like you and I working for living and renting out our time—and not just money like me and the fund, having a bunch of other people’s capital behind me.But instead code paired with audience, it’s going to be so, so powerful. And I think we’re just starting to see the fruits of that labor.Nathan: [00:04:55] Yeah. And when you get the audience going, like you said, there’s so many different channels that you can drive revenue from. And so I love that. I hadn’t thought about it, of. You know the difference between an audience and an annuity of one channel versus many, because so many people are finding that, right?You can do a paid newsletter, you can raise a fund and have the deal flow from that. You can bring a lot more than just money to the companies that you invest in. Codie: [00:05:23] Yeah, I was just going to say, you know, I’m in finance, right? And so I have a lot of partners that are older than I am, and they like, kind of don’t understand this internet thing. They’re brilliant at structuring. They’re brilliant at deal flow. but when it comes to the internet and creating an audience, they’re kind of like code of your faces on everything.It’s weird. Like, you know, do you just want to take selfies all day and like film these videos, they’re really like, they’re serious. They’re sincere in those questions. And, that makes a lot of sense because that was their wave of capital creation and wealth creation. And it’s, you know, we, humans calcify as we get older, we don’t like change, but what’s fascinating for me is that they’re just now starting to get it, because we’ve been able to raise millions and millions of dollars based off an audience that is a newsletter and that is social media channels.And so I think it will change, but I’m not sure it’ll change for the generation before us. It’ll be our generation. And the next that really capitalize on it.Nathan: [00:06:16] Yeah, that makes sense. okay. I want to dive into the creator economy. so many other things, but maybe before we do that, we should take a step back and, and, you’ve had an interesting career going from journalism to the most traditional forms of finance to now, you know, a lot more unconventional, sides of exactly what you’re talking about, where the older partners are like, wait, how do you do business?You know? And so I I’d love to take a step back. what got you into journalism initially, and then, then we can tie it all the way through to running a newsletter, you know, later in the conversation.Codie: [00:06:51] Yeah. Well, I mean, what got me in initially is I love to write, I think the power of the pen is unparalleled and, continues to be one of the most important things that you can do. And you obviously think the same because you have so much about copywriting. In everything that you do. And, you know, most people think about writing like journals or books or literature, but in fact, it’s also sales and it’s also marketing and then it’s also brand new in it.So many things. So that’s what started me off in journalism. but what was fascinating, I think is what less, why I got into journalism and more why I got out, which is I realized that. In my opinion, this was a little bit different of a time. We weren’t. So opinionated in journalism, then you were supposed to really have an unbiased perspective.But what was fascinating is I could spread this awareness. Like we won the, Ethel Kennedy award for print journalism and the Howard buffet award, for, journalism and all of that was great. We had our 15 minutes, but we were writing about these heart wrenching. Stories in Latin America, about humans, separated from each other at the U S Mexico border.And what I realized is we got a bunch of press, a bunch of people heard about it and nothing changed. And so I was just upset a little bit that you could raise awareness and have no material impact. And, what I started to realize is that the thing that actually makes things change is, is money. It’s the green language that we all speak.And power really stems from who controls the money and who can then make control of the laws or legislature or whatever the case may be. And so I actually got out of journalism and into finance because I wanted to understand money, not because I liked financial spreadsheets and it’s probably the best decision that I ever made because I could be an investigative journalist behind the scenes asking questions.Why do you do it this way? I don’t understand it. Can you go deeper? And I could draw all the information in to understand this language of money, while simultaneously. Kind of keeping it dumbed down, which is what journalists are supposed to be good at take complex contexts and sort of skinny it down so that you and I can understand.And so, ever since then, I’ve realized that, you know, I still believe in the power of Penn and sharing, but in a way that was not on somebody else’s platform in a newsletter or in a newspaper, sort of how we used to do it old school, I wasn’t interested in that.Nathan: [00:09:13] Yeah. And so you went all the way from, you know, pure journalism, straight to jumping into Vanguard and Goldman Sachs. was that a hard transition to make?Codie: [00:09:22] Well, I certainly didn’t know what a mutual fund was back then. I knew nothing about the stock market. I mean, I couldn’t have told you what a stock ticker was. So it was hard in the fact that I had no idea, you know, I didn’t know anything about this space. but the part that wasn’t hard is, as a journalist.All you’re doing all day is getting a new and interesting topic. Getting curious about it, opening 572 Google tabs going really deep into all of them and eventually pulling that data into something that resembles a storyline. Right. And so I could do that with finance too, and that’s probably how I got through it.And it’s why I think. You know, my newsletter Contrarian Thinking is all about the tagline question, everything and think critically. And it’s because if I had to hire on one basis, it would be your ability to ask questions. Are you willing to do it? Are they good questions? And do you actually put yourself out there in a place of vulnerability as opposed to ego?And, and if you can do those things, you can be an incredible investor and you can usually get to the heart of most problems. And so it wasn’t that hard from that standpoint. the only thing that is hard in finance and money is so much of it is generational. You know, when you go to Goldman Sachs, everybody went to Harvard and Yale and Stanford, and I went to Arizona state for undergrad, you know, so they were literally like, Who are you related to?Who do you know, or who did you sleep with? You know, and I’m like, Oh God, you know, I’m just here trying to figure it out. and then I did go on for the advanced degree at Georgetown later to sort of like, make myself feel better, that I was capable of being there. but that part was a little bit hard.It just, you had to prove yourself a lot. but then the trick and you know, this is, you just work harder than everybody else ask the right questions, learn each time and outwork everyone else. And. And usually, especially in something like finance that’s so playbook oriented, you can have pretty massive success, I think.Nathan: [00:11:18] Yeah, that makes sense. And then take us through, into joining the fund that you’re at now and investing in the cannabis space.Codie: [00:11:25] Yeah, I’ve always looked for emerging markets. I don’t believe I’ve ever been smart enough to go where the market’s really competitive and beat out everybody else. Instead of doing that, what I try to do is find where is there a space where the narrative. The common narrative or a common sense is different from the actual numbers.So we tell ourselves a story over here, but the numbers show something different. And anytime there’s a disconnect between the two, we have what I call contrarian arbitrage, and that’s what I’m looking for in every deal I do. And that’s what I’m looking for in every opportunity. And I saw it in cannabis because cannabis was hugely stigmatized.There was no money going into the space. And so I said, well, wait a second. If no money is going into the space, but people have used weed for millennia and they like it. I think that there will be an opportunity going forward. And so I started to allocate some investments to the space, which is what I usually do when I find an area that I’m intrigued by.See if I’m right. and it turned out there was a huge opportunity. And so it was very similar to what I did Latin America, where I found an emerging market in Chile. it was a new financial market that was opening up to exchange traded funds. And so I opened up our Latin America business for a company called first trust.And the only reason we had success and we’re able to build a billion plus business, and assets under management, not revenue, is because, Nobody else was doing it. And there was this disconnect. People thought it was dangerous. You know, they didn’t know if you wanted to go down South. We did some business in Columbia.They were concerned about that market. I knew that it wasn’t the Columbia of old. and I think it’s actually the same thing in the crater economy today. And we’ll see more and more. VCs and Gen Z investors and individual corporations, or what I call “You corps”. because that’s the next move is that, you know, media is in just as much of a mix up and disruptive state as cannabis was. And I, and I think that’ll be one of the next frontiers.Nathan: [00:13:31] Yeah, that makes a lot of sense. I love the phrase, contrarian arbitrage. maybe let’s start with that in the creator economy. Where do you see the contrarian arbitrage right now?Codie: [00:13:42] Yeah. Well, first of all, I think, the biggest opportunity is to look at yourself, you know, as a You Corp. So instead of an S-corp where we’re, you know, in a corporation, how can you individually be a company, right. And what are all the revenue lines that you can have as a company? For instance, right now I have, you know, Contrarian Thinking, which is a sort of a media business.It’s got a newsletter underlying at a free version and a premium version. We did a founding membership, Uh, you know, opportunity that was an annual subscription, a little bit more expensive. We’ll do a monthly version. we also sell another product for another company I own called Unconventional Acquisitions, through Contrarian Thinking.So I use my own business instead of having ads. On there. and then I have another couple of businesses that support the ecosystem. So a podcast production business that I invest in and we’ll do more audio through. we also have a business that does digital media. Which we own a portion of it that does, PPC.And so, you know, I’ve used this, whatever social media following and following, I have a contrarian thinking to add on these other businesses to it so that, you know, from my peace of mind right now, too many of us think. In a ridiculous way, which is that, you know, we read Peter Thiel’s Zero to One and we were like, Oh, we got to do the one thing and we have to be massively focused or we’re not going to be successful.The problem is you’re not diversified then. And so I think that’s the biggest change is you’re going to see people diversify their revenue strands, and you’re going to see you corporations that treat themselves as a corporation that have many revenue streams in it, as opposed to being not focused. so right now, you know, I probably have like, 15 revenue streams that come from different business lines that are all related to my media businesses.And that’s going to be in my opinion, in the future. And we’ll. Increasingly because we don’t trust institutions as much anymore. And this sort of divided world that we have, I think we’ll start trusting individuals more. And I think we’ve already seen that happen with things like the Joe Rogan deal. and I think we’ve seen it happen with some of the cults of personality of these other people, whether you like them or not on each side of the equation.Nathan: [00:15:58] Okay. We’ve got to dive in there cause you have, you have strong opinions on the Joe Rogan deal. I think a lot of people have said like, Oh, this validates the creator economy, this is amazing. Joe got a fantastic deal. And I know from our conversations that you have a little bit of a different take.Codie: [00:16:14] Oh, I think Joe Rogan made a massive mistake. And the only reason I know this is because I was digging through media businesses and looking at their P and L and balance sheets. Right. So, Because I’m a nerd. So I go back to finance. You go back to the numbers and you ignore the narrative. If you hear the narrative, it’s that Joe Rogan is rich and he’s moving to Texas and he’s avoiding taxes and he built a weird podcast studio and it’s super cool, right. But the truth is when you look at the numbers, it’s fascinating. And there’s been a few people who have written about this as well in regards to Howard Stern. And what the, the The funny thing about audience is money doesn’t care if people care about you, right? So capital as a leverage source, doesn’t care about relevancy, your dollar, as long as it stays in the market. And you keep reinvesting will have compound interest, right? It’ll keep growing as you keep adding to it. And you really you’re pretty passive. You don’t have to do much with it.The thing about audience is it can be a depreciating asset. Meaning if you don’t pay attention to it, if you don’t upkeep it just like you would a house, then your audience. Is going to think that you’re not relevant anymore. And a perfect example of that is, Howard Stern, Howard Stern built Sirius basically.And the numbers are incredible. If you look at Sirius radio and the amount of users that they kept, because Stern was on there. Now, if you were to ask a Gen Z-er who Howard Stern is. They don’t have any idea. I mean, I want to do these, the effort here, cause I wasn’t cause like no idea. Right. And and why is that?It’s because he gated himself and he allowed a platform to own his own company. So he became less relevant, which means that his audience depreciated and his compounding interest lessened because he couldn’t keep putting it back in. And I think Joe Rogan’s done the same thing. So Joe Rogan, by going to.So Spotify has had to stop posting videos on his YouTube channel, which had 8 or 9 million views viewers and has had to stop on, you know, Apple iTunes, where I listened to his podcast. So I no longer listen to him and has basically cut his audience—we don’t know he hasn’t shared the numbers, but have to imagine—at least by half. And I would be amazed if he kept half of his audience on Spotify. so we’ll see, they don’t share that. and instead of doing that, what I’m baffled by is who gave him the advice on this deal, because it is so easy to see with, you know, 150 to 180 downloads, which is what he said he had per month.And with, you know, an audience. In double digit millions per month. if he had put any sort of paid gate on it, just, just a premium payment a month, he would have gotten just as much in revenue. Let’s call it 65 to 100 million dollars instead of a clean 100 million dollars. I have a spreadsheet that I kind of worked this out in because I was so I was like, I can’t be this wrong about this.And, and so he would have recouped his entire, at least three year, Spotify deal. I’m guessing it’s a three-year deal again, this isn’t disclosed, but usually those it’s definitely not a one-year deal. It probably can’t be a two year deal because that’s not a long enough to grow a business. It’s at least three or maybe more.And, and he did it for a hundred million dollars, which he could have gotten in a year. And so that to me is astounding not to mention now he can’t productize on YouTube. and he’s had some hiccups in the platform actually, whether or not it’s true, you know, letting him play some of the more controversial episodes.And so, I think that is. Gonna be something very different in the future. And you’re never going to see like a Mr. Beast go and sign an exclusive deal with somebody because you can monetize content in a way that you can’t monetize music. People will pay for a Joe Rogan and China is the perfect example of this.They’re doing it all over and I think we will do it in the future as well. And we’ve already done it with newsletters. Podcasts are just a matter of time.Nathan: [00:20:13] That’s interesting to think about the continuum between say like Howard Stern and Mr. Beast of you’ve got different business types and then, you know, different generations and Joe Rogan sitting like being the transition, the, you know, the transition creator in there who is using a lot of these new ways to create, you know, on the forefront of some podcasting and stuff like that, but still you’re being attached to this older business model of letting me do a big deal with Spotify rather than pursuing, you know, product lines, memberships, et cetera.Codie: [00:20:46] Totally. I actually had an interesting call with one of the very high execs at CAA, and I got connected to her because her brother’s an investor in one of my funds. And when she heard about Contrarian Thinking that I grew by a hundred thousand subs, and I know she was thinking in the back of the mind, the Joe Rogan thing and like, Oh, I should, I should figure out what these people are doing with newsletters.And I should like get a board seat. Right. So she wanted a board seat on Contrarian Thinking; I’m like, I don’t even have a board. Like we’re just running. We don’t know what we’re doing right now. And, and she said to me, well, you, you know, you too, Codie could like do a, a big, obviously not Joe Rogan, but like you could do a deal at some point maybe.And that’s what she was going for. And I had to stop her and say like, you’re, you’re missing the business model. The business model is not that I have like a platform or a brand that allows me to monetize the business model is I go direct to the people. They helped me monetize and then nobody ever owns me ever again.And if I want to do some deal on a one-off basis on something that I do, like series or something fine. but. For the future. I don’t think anybody will sell out to, a network like that again, or if they do it’s because they really don’t want to run the business and they’re over it and they’re kind of slowing down and that I could see it.Nathan: [00:22:02] Yeah, that makes sense. Because the other side of it is I think it’s an amazing deal. For Spotify, where, when they look at the long-term benefits of, you know, what a subscriber is worth to them, you know, I obsess over like freemium business models, free to paid conversion rates. And Spotify is the gold standard of, you know, in like software and SAS have free to pay conversion rates and then they do great on retention to everything else.So for Spotify there they’ll print money off of this deal. It’s just not the win for the creator.Codie: [00:22:34] Oh, you nailed it. I mean, they had a $3 billion uptick in their stock price after Joe Rogan closed a hundred million dollar deal. I mean, that’s how, you know, the deal is shitty and it was great for Spotify, but not for Joe. and not to mention, I mean, I doubt he got equity in the company. Maybe that’s some of the upside that he got.But you know, if you see the. The value of Spotify today versus then, and the continual capture, like they’re winning as the platform, as opposed to the creator. And I think creators are waking up to that more and more and more, especially as they’re able to pause, you know, the like traditional celebrities, the actual Hollywood celebrities, I think are usually running gun in competing from you to movie deals, whatever the case may be.But now that. The movie theaters and, or I’m sorry, the movie studios get to decide who gets to work. I think people are slowing down and saying, wait a second. You know, I don’t need these guys. Like I used to. And, you know, and even they, and they need massive budgets, you know, to do their films, podcasts. It costs us nothing.Look at what we’re doing this for right now. You know, I have like a camera I’m sitting on like some pillows at a higher chair. So the views okay. Behind me, like this all costs 20 bucks. Right. You know, it’s very cheap. and so, yeah. Yeah, I think going forward, you don’t need the platforms to give you the money to, for you to make cool things.Nathan: [00:23:54] Yeah. What do you think about the amount of capital and attention that’s pouring into the creator economy right now? Like we’ve seen, so ConvertKit is totally self-funded and we don’t. Take on capital and any desire for that, but the amount of outreach, lately it’s absolutely wild. Like, I got some of them, Google ventures reached out and I was like, okay, I’ll take like one call every quarter or something, but it was the founder of Google ventures, the former CEO of Google.And I was like, there’s a level of money and attention coming into it, into the space that, you know, a year ago, 18 months ago was not the case at all. So I’m curious for your take.Codie: [00:24:34] Yeah, well, I mean, I think we have a little bit of a. Short-term memory. I mean, everybody thinks about Apple and like Steve Jobs is like doing a $10 million seed fund or seed raise. Like that’s not what happened, you know, they self-funded by selling the hard, you know, motherboards to a bunch of mom and pop shop shops forever.And so, I think. You know, people caught on to tech, but they caught on later than people remember. And this, you know, a wash of money, that’s common to not just the creator economy, but every single thing that can be VC backed right now is VC backed. you know, I was, I have a good friend. That’s a partner at Andreessen Horowitz and, and he told me.You told me verbatim that capital is a commodity to them. They have so much money that it’s not interesting. They turn it away and Sequoia perfect point. They don’t take new investors unless they’re non-profits or pensions. If I had a hundred million dollars and I went to Sequoia, they would tell me to go pound sand, like that’s wild.And so to your point, I don’t know, I’m of two minds, because part of me is like, wow, well, when you have that kind of rocket fuel, you can grow like crazy. Right? And so there’s a real benefit to that. And there’s the scary part is they try to scare you. If we don’t fund you, we’re going to fund Joe. And Joe is going to sweep the floor with the amount of money that I have, but I’m going to give him Write, which is what they do.So there is that. but I also think in this world today, you know, if I’m sitting in your shoes, I, I mean, I’m not taking, I don’t, I don’t want to take funding. Why? Because I don’t really want to exit contrarian thinking ever, you know, and yours is a SAS business, much more equitable. but, you know, you probably don’t want to exit right now.You want to build something cool cashflow for a long time. And if you do exit, you don’t want to do it because of pressure for a 10 year fund return and to have, you know, To work for another boss, which is investors. So, but you’re rare. Most people do give into the money. so it’ll be interesting to see what happens, but I do not think that capital is the only type of rocket fuel anymore.There’s so, I mean, perfect example is like, look at what we’re seeing on Twitter. I mean, you and I go back and forth on Twitter all the time and I’m amazed, like. You know, Sean Perea and having him in country and thinking on Friday with him raising three and a half million dollars, like on Twitter and 30 days from like total strangers.And, you know, there’s just so much money a wash, that it does. It makes me a little nervous, but I get why you won’t take it because then you work for somebody again.Nathan: [00:27:06] Right. Yeah. So let’s, let’s pivot a little bit and dive into newsletters since, that’s, you know, what’s on the, on the label of art of newsletters. I’d love to hear, take us behind the scenes of growing concern and thinking and what it’s been like to, to grow it to the level that you’re at now versus how many subscribers do you have on contrarian thinking?Codie: [00:27:25] We have about, yeah, we have about 102,000 subscribers now, so that’s awesome. Thanks. You know, we, there’s a couple of things that led there. Like one, you know, I had a newsletter list that was maybe like 10,000 or something like that, that I had just never paid attention to. It was called the struggle.Isn’t real back in the day. and I hadn’t emailed them and like, Yeah. Year’s I don’t even know. And so I started with that and then, you know, you and I both have been kind of public, not like trying to be public failures, but relatively public on social media. So I had like some social capital built up.I’d never asked. Anybody for a dime. I’ve never asked anybody to subscribe to anything. for years I just kind of talked out there and if somebody was interested. Cool. but what happened in January of 2020 is to be fair. I saw. A world in which we were not open to thinking critically anymore. It was a world where questioning things.Wasn’t okay. And I’m a journalist. I think that is the most important thing that we can continue to do is ask why, why, why, why, why, why, why, why? And people weren’t doing that. And I think that’s really dangerous. And so I emailed a group of my friends and I kind of went to the ones that I thought were most influential. And I said, I’m going to start this newsletter. It’s just going to be for us. If there are 10 of us on here having real conversations while we’re locked in our basements during this pandemic, then awesome. We’ll have cool conversations and it’ll be hopefully compelling. And I hope you disagree with me on some things.And if, if that’s all there is then great. So that was sort of, the impetus was thinking critically. And then, it grew from there and, and I did, I’m not one of those people. That’s like, Oh, they just showed up. And one day, like I created this thing and then the millions of people just found me and like, Oh, it was so sweet.Like I never believe that I’m always like, no, not like what happened. Tell me the truth. So I did, I’ll get to some of the Marketing things I did. I absolutely did do that. But when I started, it was really with this sort of idea. And then, how it evolved slightly was I realized like a lot of the reasons why we aren’t questioning things is because we’re scared about our financial freedom.We’re scared if we questioned things, we’ll get de platformed or, somebody won’t agree with us or whatever the case may be. And this isn’t a political thing. This is just like broad based questioning. And so I started it. Some people got interested. They shared it with a few people who had other big platforms and it started to grow.And then I have a link if you go to Contrarian Thinking, that says how I went from, you know, basically my first zero subscribers to 10,000. And on there, you can see the hustle, the LinkedIn posting, the social media posting, you know, the emailing, all of my contacts, asking them if they want to join. I did all that stuff.And it was a slow roll. But I’ve never used ads and I’ve done a lot of, organic promotion and cross collaborations like this, which has probably been the fastest way that I grew was like, you know, this’ll be great. And then, you know, Noah hooked me up, Noah Kagan hooked me up with talking about it and Sam Parr at the hustle and trends.And, I think when you’re saying something, because you can’t shut up about it, like you just have to say the thing, People tend to respond to that. And that’s how stuff seemingly goes viral. And I haven’t ever had anything go crazy, crazy viral to like the tune of hundreds of thousands, but definitely thousands and tens of thousands.And it’s spread.Nathan: [00:30:57] Yeah, that makes sense. So when you’re putting together, you know, a partnership or someone you’re wanting to do a crossposting with, I know newsletter swaps are, are kind of a popular thing. I’m curious how you go about that. You, and I have a bit of an advantage in that we’ve been, we’re friends with a lot of people already.And, you know, so it’s kind of just like texting a friend, like, like Sam Parr, and saying Hey, let’s do this thing, but how do you go about planning those out? Or are they all just purely?Codie: [00:31:29] Yeah. I mean, it’s, I think it’s really hard. I was just, I have a little bit of a team now I was a one-woman show forever. And then. basically last month or the month following Noah again, yelled at me and was like, like, this is a real business. Why don’t you treat it like one? And I was like, why don’t you mind your business and go back to talking about tacos.And he, basically was right. And so, I hired a few people and I’ve been having them do try to do cross promos and to be perfectly frank, it doesn’t work with strangers for me. Like it doesn’t work for a couple different reasons. One because. I think it comes off as like thirsty to people. You know, if you’re like, Hey, will you share my newsletter?And I’ll share yours, unless it’s a newsletter that curates other newsletters or other specific things, and it’s hyper targeted. broad-based outreach hasn’t really worked for us. the thing that has worked is like you said, You know, providing a lot of content and value to people for years, and then finally calling in a favor, then also engaging a lot with their stuff.So like to people that I like, I’ll S I’ll write about something that they’re doing authentically. No expectation. And then I’ll share it with them I’ll be like, Hey man, I’m doing this thing. Like, and this was cool that you did this. So, I wrote about it and maybe you get a few new subscribers or whatever the case may be.And, and so that’s helped, but I think the biggest thing is authentic connection and, and actually giving to people before you ask, we tried piping for awhile, which was like newsletter. cross co-lab like a site. and you’ll have to tell me if anything’s worked for you, but I found it was a lot of, it was wasted time, you know, you’d reach out to somebody they’re mostly one man shows, so then they’d reach back out to you and they’d be like, yeah, I’m interested.And then you’d get into the nitty gritty and then they’d like fall off and then they’d come back a little bit later and be like, Oh yeah. Well, where are we going to do about that thing again? And, So I, I didn’t find that was hugely valuable. It’s much easier in my opinion, to retweet people, to, you know, ping back and forth on Twitter, to repost people on Instagram, to like post people and Instagram stories and use other social media platforms and then circle them back around to the newsletter, which is usually what we do.Nathan: [00:33:48] I like what you’re saying about writing about people. Because that brings it, that ties back into being a journalist, a journalist, right. Of taking their story. Anytime you see someone doing something interesting, right? Like you wrote about Noah and his, his video and everything. He posted about getting to a hundred thousand subscribers on YouTube and you can do it from such a genuine perspective where you’re like, Oh, Really they’re doing that.Like, anytime you come across something on the internet where you’re like, I hadn’t thought about it that way, instead of just like putting it in your private notes and archiving that and remembering to circle back to it later, like write about it in your public notes and say like, Oh, it’s amazing how Sean went and raised this fund on, you know, on Twitter or like other things he’s done.He had a paid newsletter and he shut it down and you could write about that and you know, anything you’re fascinated and then publish it. You know, or send it to the person before and saying, Hey, I’m about to publish this. You want to give me any commentary? Or like, would you mind making sure, like fact check a little bit, make sure I got everything correct.And that’s such a great way to, to meet someone and get to know them when they’re like, wow, you care deeply about what I’m doing. You understand it more than like a quick glance at Twitter. but you know that at that high level, and if you find it fascinating, you probably think like I do. And so great.Sure. Let’s be friends. And by the way, thanks for sending me.Codie: [00:35:07] Yeah, exactly. And also one of the things that’s worked for us is like reaching out to people that I think are doing interesting things and just saying like, Hey, this is really interesting. I might want to highlight this and here’s where I’m at. And maybe this is useful to you or maybe I’m too small.I don’t know. but like, what do you care about and what are you actually focusing on right now? Is there something cool that you’re doing that I should know about and that I should push out as opposed to the stuff that’s already out in the marketplace. And that just happened with, Hmm, I’m blanking.But another person we’re going to do a cross promote with. And, and he basically was doing a panel on SaaS evaluations and was like, well, you know, the newsletter cross promo doesn’t really work for me, but if you want to share this thing, why don’t you come on my panel, it’s going to be to a thousand people.And maybe we get, you know, mutual contacts from there. And so leading again with like, what do they care about? It’s a pretty selfish ask for me to reach out and be like, Hey, bud. Trying to grow. You want to go ahead and give me all those followers you created. That’d be awesome. and instead saying, Hey, what do you care about?And then I’ll try to help you grow that. And you know, it’s the used car salesman way. Honestly, we’re trying to do it in a nice way, but that’s why they give you the hot dog or they give you the soda or they give you the lollipop. They like almost make you take something. And that’s because it works. It’s called reciprocity.If I give you something and you take it, you feel like you have to give me something. And, and humans are funny like that.Nathan: [00:36:31] I’d like to get into a little bit of those nitty gritty tactics that you did, you know, for someone listening, who has, you know, they’ve started their newsletter, maybe they’ve got a hundred subscribers or, or 500. What are some of those things you’d recommend to get them to 1,000, 2,500.Codie: [00:36:45] Yeah, well, first of all, you know, this, it, like if you want to do a subscription game, it is a, it’s not a viral one-and-done situation. Sorry, not going to happen. So if you don’t have a consistent process for moving forward on client acquisition or, you know, email acquisition every day, I don’t think you’re gonna make it.Maybe you don’t have to do it every day, but at least like one day a week, you’re spending two or three hours thinking about how do I get more eyeballs on the stuff that I do. a lot of people think if I build it, they will come. And I think you’re crazy. That’s not how it works. and so the, the couple of things that I did are like, here’s some hacky stuff, like for instance, in your Gmail contacts, If you go to all your Gmail contacts and you click on it inside of actually all of us have like six different emails we’ve had from different companies over the years, and you click on all of them.There’s a whole host of other contacts, which is basically anybody that’s ever emailed you of all time. Now you gotta be really careful for email laws. But you can reach out to these people on a non-spam basis. So individualized or through mail merge, and basically say, Hey, I started this thing we’ve been in communication.I was really honest about it. I was like, we’ve been in communication at some point in time. You could have been selling me an ice cream cone in Mexico city, or we could be buds. Like, I don’t really know. There’s a lot of you on here. but, I’m starting this newsletter. Here’s why, here’s how it might be interesting for you.You’ll only get one email from me. It’s. From me direct, I’m a human on the other line of this. And if you want to join along, that’d be rad. so, and here’s Here’s the thing. Some people are going to respond. Like when I wrote that somebody, like, I got some nasty comments on, on my newsletter, Like if anybody did that to me, I would never speak to you again.And it’s like, okay, great. Right. Well then don’t speak to me again. Like we obviously okay. and so, you know, just put yourself out there, but I think that that Google contacts hacks kind of fun. And then you can download all your. You know, phone contacts, which I did to just make sure to not auto subscribe people that’s shitty.But I thought about it, like, you know, people email me all the time with Christmas cards every year that I haven’t seen in decades. And I’m like, okay, thanks. So you’re, you’re you’re cool. Emailing me like a picture. Of your Christmas card or your baby’s announcement. And this is just my business baby.So I’m going to tell you about it and you can decide if that’s cool or not. And then, some of the other stuff I did was just using tools that are very straightforward, you know, like being really dogmatic about buffer scheduling. You know, a tool for scheduling on social media consistently, being really dogmatic on asking some of the people who are centers of influence in my life.I mean, we’re all six degrees away from Kevin bacon, right? So we’re probably six degrees away from everybody else. And so asking people that I know have some influence, even if it’s just with the PTA, Hey, I’m creating this thing. Would you be open to sharing it? Like, you know, do you have anybody else that you think.You know, would be interested in this and those little tiny ads probably got me to my first, you know, 1,000 2000. And, I didn’t know, a more viral way to do it than to go sort of modern day door knocking. and that’s what worked for me.Nathan: [00:39:58] Yeah. And I think if you think about it like a flywheel, those are the first few times, like those first rotations are a lot of those really hard, hard things. And then now future rotations with flywheel, like if you think of a fly or a turn of the flywheel as like an additional thousand subscribers, that first one is really hard. And so you all the scrappy stuff but now Write we’re talking let’s go from 102,000 subscribers to 103,000 subscribers And you’re like over here and you’re like give a flywheel spin you know like you’re there we You know we got And it’s still a bunch of work, but, not to the same level that it was in the early days.Codie: [00:40:37] That’s exactly right. Yeah. And you, your, your goals shift. So you’re like, if you’re the type of person that’s into this, you’re never happy. Like every time I have a week, that’s like less than 500 or a thousand new subscribers. I’m like, Oh, what’s happening. And then, you know, back in the day, that would have been the Holy grail.And so I think just. Trying to remember where you’ve come from and the journey along. And then also not forget, you know, the reason we create any of this stuff is good because we think that there’s, somebody might want it. And so if there are so not to forget and to engagement, instead of subscribers is one of the things I have to train myself for, because I.Who cares if I have 500,000 people on the list, but nobody’s really engaged. Nobody’s commenting. Nobody’s asking questions. That’s worth much less to me than a 50,000 person really engaged email list.Nathan: [00:41:25] On the engagement side, you have, an interesting writing style in a couple of things. You’re very conversational and you’re very like straight to the point, whatever. Someone else would dance around, you know, or say with, nuance. You’re just like here it is. Exactly. And I’d love to is that because that’s naturally who you are or is that trying to drive engagement?How do you think about it?Codie: [00:41:50] That’s a great point. you know, I think it’s probably a pushback for the fact that I’ve been in finance for so long and we have to be so, you know, prim and proper all the time. And, and it’s exhausting and I don’t think it’s very efficient. And as a sales person, you’re always just like listening to the other person and pretending like, Oh yes.Tell me about what you did. Johnny’s soccer game last night. Like I cannot wait. and so with the newsletter, it was a chance to not do that. I was just like, fuck it. You know, I’m gonna have to say what I want to say. If people don’t like it, that’s all like, we don’t, it doesn’t, it’s not in your face.If you don’t want to listen to it, you just unsubscribe. And so it’s not mean it’s just, you know, I’m not your cup of tea. No problem. and so. I think that’s probably a natural, it’s one, you know, all of us have so many segments, right? There’s like the Nathan with your wife. And then there’s like the Nathan with like, you know, the CEO of XYZ company.That’s coming to you to give you a bunch of money. Like we’re all a little bit different. And so this Codie is, yeah, she’s kind of in your face because I think. Maybe we need a little bit of that as a society. and also, because it’s fun to write that way. And I think some of the best newsletters or writing sources in general, it’s, it’s a, it’s a person, you know, it’s like when you read a novel and you hear the voice of the main character, the protagonist in it, and you associate with them and the main voice when it’s, you know, I dunno if you think about like the Hobbit, when it’s.You know, the Hobbit and you have the original cast, the voice is one way. And then when you move along and the characters change the voices another way. And so, that is the cool part about writing is, is you can change sort of who you are in that moment. and I have a lot of fun with it and I think.You know, if you’re going to talk about subjects like wealth creation and revenue streams and compounding interests, like, you know, immediate snores mill, you have to do it in an interesting way because I picture it like every single reader when they’re reading contract and thinking, and they have their phone out, they are simultaneously driving.With the music at top speed with the person next to them, blaring some tick talk nonsense with the people in the back recording for IgE TV. And it’s like a clown car of attention, grabbing things. And I have to like slap him in the face with what I’m saying, and it’s hard to do and writing. And so, my favorite writers do that.Like I think Sam and his team are geniuses and that. aspect. And I think Jonah Goldberg from the dispatch talks about politics and this like incredibly funny way. and if you’re going to write a newsletter, you might as well do it with some personality.Nathan: [00:44:29] Yeah, well, and it just brings so much of this. I don’t know when people are saying like, Hey, I’m doing this business and I don’t know, it’s hard and you’ve just come. And you’re like, Oh, of course it’s hard. Like, you know, and this tone of you can still be kind, but instead of having to dance around any issue, you can just dive right into it.Codie: [00:44:47] A hundred percent.Nathan: [00:44:50] One of the other things that I want to talk about is, monetization. So with a newsletter, when you taking all the way back, when we’re talking about building wealth audience, being this pillar of it, and you can, once you have the audience and the attention, you can earn money in so many different paths.I’m curious what you’ve explored with the newsletter for monetization, and then you do have this, paid component to it. And so I’d love to hear why you chose that.Codie: [00:45:14] Yeah. You know, it’s also funny because once you go down this monetization realm and I’m sure you’re the same, right. It gets overwhelming for me because there are so many different things that you can do and everybody is right when they talk to you and they can be very convincing. And we run in a lot of friend groups with very smart people.So I listen to one person, Charles Gaudet. And he’s like, you’re crazy. If you don’t just sell $5,000 products and do it this way. And then this other, person’s like no $19 newsletter and sell it for 300 a year and get a million subscribers. And both of those things are, are right. You know, it just depends on what business do you want to create.And so the hardest thing for me has been. Being like, okay. Input, input, input, input. And then nobody talk to me for 48 hours and I’m going to figure out what kind of business I want to create, because if it’s not fun, it’s not going to be sustainable. And you’re going to be in the graveyard of newsletters that exist out there.And also if anybody’s selling a newsletter, I want to, I like buying them. So, so shout out for that. If you’re not doing anymore and you want to sell your, your, your newsletter hit me up, But, so, the way that I first Monte wanted to monetize was, not selling anything from the newsletter. I had a separate company that does an affiliate code with my newsletter and I own this other company and we sell.You know, $500 and $3,000 products that are related to M and a buying businesses, selling businesses, how to do that. So it’s like an education business. And so we posted some stuff organically and contrarian thinking and that business. that was the only way I marketed that business. And that business did a $50,000 launch basically on the back of Contrarian Thinking. We really didn’t know what we were doing. You know, we’d like just kind of like, like, Oh, here’s an affiliate code and here’s a little story. And now that business, I think we’ll do about a million dollars this year. So that’s cool. and, and that’s a million dollars gross. Like I don’t, you know, margin wise, it’s, it’s not the same thing, although we don’t do ads, so we have pretty decent margins.And then in Contrarian Thinking. I did want, I like each of my businesses to be profitable. I don’t know what you think about this, but like, I like each of them to be incentive aligned so that I can have team members that I’m like, okay, you are focused on this creative thing, but also this creative thing drives a monetary thing.And it’s very easy for you to know if your actions drive revenue because the business has a profit line to it. And so. we launched a founding membership. It’s $500 and it’s a lifetime yeah. Membership to start. And we’ve done about a hundred thousand dollars. So that’s about like 200 members, something like that.And I think we’ll, we’ll cap it. If we get there, we’ll cap it at like 300 members. There’ll be some exclusivity for the fact that they joined us early and then we’ll do a paid monthly mechanism. And I’d be curious on your take, but I don’t think I’m going to go cheap. I’m not going to go 10 bucks. I’m not going to go 19 bucks.I’m going to go. 29 to $49 a month. And I’m going to have a bias towards an annual subscription because I’ve heard churn is pretty aggressive in most newsletter businesses. And the premium version is not just another newsletter that people get. It’s a live recorded call on a specific topic related to cashflow.So this one’s called Contrarian Cashflow, and it’s with an expert, somebody like John Perry, who’s raised a couple of million on Twitter or somebody like rebuilt, who grown a hundred thousand Twitter or YouTube followers and makes about a hundred K a month from his Airbnbs. and what it is is it’s not just like Codie.Tell me your story. It’s very tactical. Sean, what exactly did you do to raise? What was your tech stack? How do you value the companies? Do you have models for all of those things? And so the goal is each month over the course of a year, you’ll have 12 ways to cashflow and you’ll have a playbook to do it, and we’re going to try it for a year and see how it goes, but I’m having fun with that right now.Nathan: [00:49:17] Yeah. Well, what I like about that is it doesn’t get you caught up in the problem of growing the list with free content that now is behind a paywall and you can’t use it to get new subscribers. You’ve actually got. A distinct thing where, where you can grow the list in the same way that you always were.And yet you don’t have this like huge burden of New, you know, premium content that you have to create.Codie: [00:49:40] Okay. Yeah. I mean, I don’t think anybody opens their inbox and it’s like, God, I wish more emails were in there today. That’d be awesome. so I try to avoid that.Nathan: [00:49:48] What were some of those other things, when you, when you came to that monetization, like, were you considering sponsorships or. You know, more premium products, you know, of the courses and other things, or, you know, like when you did that whole download and then unplugged for 48 hours and send like, okay, stop talking to me, I’m going to sort this out.What were some of the other factors that went into that?Codie: [00:50:11] Well, I looked at the ad model, which is interred and a few people reached out to, have sponsorships or ads, but it’s so non-scalable, you know, that’s not there it’s, it’s not automated. so you know, each person you’ve got to negotiate with them and then they want to know what you’re going to Write.And like, I started this thing because like, just like, like don’t tell me what to do. I’m like a four year old, No. And so if I have to get ads, then they tell me what to do again. And I hate that. And like, maybe at some point I’ll be big enough where. That won’t be necessary, but for the short term, for a hundred bucks or 500 bucks or a thousand bucks, which is a lot of money, but it’s, it’s control and it’s time.And I think if you were to average out the amount of hours, it takes to get ads and sponsorships in your newsletters divided by the actual amount that you make on them, the ROI would actually be really low. it’d be interesting actually, to try that. and so I, I didn’t, I don’t want to hire a sales person to do it right now.Now, as we get bigger, maybe that actually makes sense, but I don’t want to do it myself. And so I said, no, thanks to ads and sponsorships. Then I did look at doing the course thing, but I have unconventional acquisitions as a course. And my real interest is not creating a Codie business. It’s creating a media business.And so I want people to come for the content. You know, I want to have a community that they stay for and I want to have some, I don’t want it to feel like you’re in a copywriting funnel. Like, you know, like they come to Contrarian Thinking, and they’re getting sold down the funnel to my big products.Like, that’s not, it, this is actually a media business where we are trying to give you incredible content that is actionable, that we take action on ourselves and we do it in a way that doesn’t bore you to tears. And, that seemed interesting to me. But I do think like, I think we could have had a $600,000 launch.If we did, like an actual funnel with multi thousand dollar products. and, and, you know, maybe one day we’d do some part of that, but I, I would even do it. I would do like a sprint or something. I would do like an eight week maybe educational course or something on something that I’m interested in. I wouldn’t be tied explicitly to a revenue. Yeah. Forever.Nathan: [00:52:28] Yeah, that makes sense. One of the last things I wanted to ask you about is building a team. I think a lot of people, you know, get to this point where they, they start an audience, a newsletter, maybe it’s at 10,000 subscribers or 5,000 or 50,000, somewhere in there. They’re like, this is more than I can handle.And so they’re listening to you and you’re like, yeah. And I spun up this thing and I like it to be, you know, operate on its own and have its own, you know, profit and everything and, and all of that. Well, you make it sound pretty easy. So what, what advice would you have for someone who’s ready to make that shift and go like maybe beyond an assistant or something and actually start to build out a team for their business.Codie: [00:53:05] I mean, it’s not easy and I don’t have it all figured out and I screw up all the time. but I’ve hired a lot of people in my career, in finance. And so I’ve learned a couple of things. One is fire super fast. So like when I first started thinking of building out a team. Start with what you’ve already created.Start with the people who are already obsessed with what you’ve built, which is your subscribers. Every single person that I’ve hired for Contrarian thinking is a subscriber to Contrarian thinking naturally, I don’t go out and search for them. I don’t go out and find them. I write in the newsletter that I’m looking for, these certain types of things.And then I ask them to come to me with some. Some showing of them wanting to be part of the, of this movement. and so they do in funny ways in videos and whatever the case may be. And so, and then I, and then I try to pay them well. so, that would be one is like go to your subscriber base and find people who are irrationally into what you’re doing.Everybody’s got like, even if you only have a thousand people on your email list, I bet there are one to 10 people that love it. And they just read it and they love it and you get the emails from them—find And so those people to work for you. And then second, a bunch of those people are not going to work out and they’re going to love it, but they’re going to be totally inept.What I basically do is I do projects. I don’t hire anybody straight away. As employees, everybody’s project-based And the first project is usually something really tangible, like put together a proposal for me on how to grow and then show me the three different ways you want to try to execute on it.I’ll pay you 500 bucks or something for that. And then you go try those three things. I’ll pay you another 500 bucks when you try it. And you tell me what the results were. And you’ll be able to tell pretty easily if, if somebody is good or not, and then. Sometimes they sneak back that past that phase and they’ll get in any way.And, if you don’t get rid of non high-performers upfront, they’ll bring the whole team down. So, but usually they’ll self-select if you’re on top of them. So like we use Slack, we use something called the top five, which is we go over on Mondays and Fridays. everybody writes in their top five. You won’t believe the amount of people that won’t write in their top five by Monday morning.And naturally right They’re over the weekend, they forgot about it on Friday. That’s a great self selector. and so if you don’t fill it out, it’s like Hey That’s what we needed. Sorry. Like this isn’t a good fit for you. and then I think the other thing that’s important is being really self-aware like most of the time, if it doesn’t work out, it’s my fault.Either I picked the wrong person or I didn’t explain it properly. And most of the time I am. I’m still the choke point. You know, I still am the one that’s involved in too many things. And so, realizing that and trying to pull yourself out and let you know other delegate to other people. Oh, and if you find a good copywriter and you don’t write all your own copy, never let them go because they’re so rare.Nathan: [00:56:03] Yeah, that that’s so important because that’s probably the last thing that people feel like they could ever give up. They’ve been writing a newsletter and it’s like, Oh, this is my voice. This is, how it is, which you should put a ton of your attention into that. But when you find someone great, I editor copywriter and they come back and write something exactly as you would write it, you’re like, what is this? This is magic. That’s better than I would have written. So I agree.Codie: [00:56:29] A hundred percent and then it just opens up your time to focus on the content pieces that you’re obsessed with, you know, and go really deep into those. I’ve only ever found one good copywriter and I’m trying to make her mind forever. And we’ll see if that works.Nathan: [00:56:43] Yes, that makes sense. Well, thank you, you so much for coming on. Where should people go to subscribe, to concern and thinking and, follow you on social and everything else?Codie: [00:56:53] Yeah, so, the website, we’re actually building a new one, so you’ll have to tell her that’s wrong with it. If you go check it out, it’s a contrarian thinking.co. so check it out, subscribe there. the blog and all the old newsletters will be on there right now. It’s it’s on sub stack. And the only thing you can publicly see, and then I’m pretty active on Twitter and Instagram.It’s just Codie Sanchez, @Codie_Sanchez. So I’d love to connect and if I can answer any questions or, you know, yell at you and the tone that I usually do, I’m, I’m happy to do that.Nathan: [00:57:25] It’s it’s yelling with your best interests at heart, you know? And so, you know, that’s Write or, you know, it’s that older sister or someone else who’s like, come on, you can do better. I know you can do better.Codie: [00:57:42] And believe me, I do it to myself in the mirror all the time. but I, I certainly appreciate everything that you have built and everything that enables creators to create. So thanks for all. ThatNathan: [00:57:53] Yeah, well, it’s good to connect and we’ll chat again soon. 

Packy McCormick writes the popular newsletter Not Boring, which is all about strategy and investing, from big companies to small. Packy was the VP of experience at a company called Breather, but when he left that role to start another startup he ended up creating a blockbuster newsletter instead! Not Boring has grown to over 30,000 subscribers.Packy’s newsletter is generating fantastic revenue, and his business model is a little different from the paid subscriptions that are popular right now. He dives into all the specifics. If you’re curious just how much you can make from a 30,000-subscriber mailing list, don’t miss this episode!In additional to business models and why he chose his, Packy also talks about the tactics that worked to rapidly grow his newsletter past 30,000 subscribers, the difference between being a writer and being an investor, and more.Links & Resources Prof. Scott Galloway: Overhauling Twitter Breather - Unique Meeting Rooms, Hourly Offices & Workspaces David Perell - Write of Passage Roam Research – A note taking tool for networked thought. Benedict Evans Clubhouse: Drop-in audio chat Packy McCormick’s Links Not Boring by Packy McCormick Home page: packy - Beacons mobile website Twitter: @packyM Episode TranscriptPacky: [00:00:00] It is about sitting at your computer for hours and hours and hours every week. And making sure that you’re getting it right. And then you’re finding the right angle. Find something that you actually care about if you’re not interested by the things that you’re writing in. So you could probably bake it for a little while, but I think it really comes through when the writer is really interested in the things that they’re writing about.Nathan: [00:00:25] In today’s episode, I talked to Packy McCormick who writes a really popular newsletter, Not Boring. Packy was the VP of experience at a company called Breather. And then he left that role to start another startup and then decided to start a newsletter instead. And Not Boring has grown to over 30,000 subscribers.He’s got some pretty fantastic revenue. He dives into the specifics. So if you’re curious how much you can make off of a 30,000-subscriber mailing list, we talked about that. One of my favorite things is we get into business models. Paid subscription, is that best, or selling products or sponsorships?And so we dive in Packy shares why he chose the model that he did and why he thinks that’s the best for his audience. So it’s a really fun, wide ranging conversation. I think you’re going to enjoy it. Packy, welcome to the show. Packy: [00:01:12] Great to be here. Nathan: [00:01:13] Thanks for having me. So I want to just dive in and hear a little bit about what are your, some of your favorite things to write about?Packy: [00:01:19] Yeah. So my favorite things to write about, and I actually, it took me a while to kind of get back to my favorite things to write about. I was writing about community and sleep and like just kind of all over, just doing the, I think the normal early newsletter thing of like thinking that you’re a fantastic curator of the internet.And what I really loved writing about recently is as business strategy companies, big companies, small, and mixing that with finance, that’s taken a couple of years, but I think I’ve kind of hit this sweet spot where it’s a more fun approach to these topics that are kind of. Not super fun normally, which is business analysis and finance and the stock market.So I’m just trying to, you know, make it approachable, fun, and enjoyable while you’re learning something. Yeah. Nathan: [00:02:01] So what’s an example of one of those, of like a business strategy for a particular company that you’ve, you’ve enjoyed. Packy: [00:02:06] So I, this past week I wrote about Twitter, and, and wrote about, you know, how Twitter is this company that has been, you know, that I think a lot of us use and are on all the time, but it’s done.An absolutely horrendous job of monetizing. So talked about it through the lens of professor Scott Galloway wrote a piece. And so what was wrong with that piece? And then what I thought that Twitter should do and why I think that Twitter is actually undervalued and this idea of like, you know, once things start kind of changing for Twitter, there’s so much love for the company that I think people are just gonna pile into the stock.A lot of this is about being lucky. I wrote this on Monday, they reported earnings on Tuesday and it’s up like 27% since I wrote about it. So just got super lucky on timing there, but there’s a lot of that like kind of combining how they should think about business strategy and then how that parlays into the market.So it’s less really quantitative and more like, here’s kind of what everybody’s saying about this company. Here’s what they’re doing. Here’s what maybe they should be doing. And if they do that, here’s what it might look like today. For example, I wrote about, Y angel at early stage valuations are not as crazy as they seem based on the fact that Amazon and Apple and Facebook and all these huge companies have grown actually way faster than the average startup valuation has round by round by round.And so just kind of walking through that, but then weaving in. The movie up as an analogy and, you know, the four minute mile. And so just try to like, make it super fun and approachable. Nathan: [00:03:31] Yeah. I like that one. And I have to say, I, on Monday, last week, I read your Twitter post, especially as you know, you’re diving into the creator economy and all this stuff that.It’s just so much fun. and then I was like, this is a compelling case and I’ve owned, you know, Twitter stock for years, but not very much. I bought more, after that article, so you’re already making me money. Packy: [00:03:52] That’s, that’s amazing to hear that scares the hell out of me. So I wrote about Slack a couple of weeks before they, before they got acquired and, had this, like really this, this case of like, I love this company.They’re just being mistreated by the market, all these things and, and made a, I think a fairly compelling bull case. And then they popped for totally different reasons. Something that I did not write about, but people came out of the woodwork and were like, Oh, thank you so much. I bought Slack because you said to buy Slack and bill.And I got a little bit scared, frankly, because I was like, I’m not a professional, I’m not a registered advisor. I’m not like. Amazing. If you like, then go do your own due diligence, I love that you’re investing, but it’s scary now that the audience is big enough that people are actually putting money behind the things that I’m writing, which is why.Nathan: [00:04:33] Yeah. You don’t want the like yep. I put my kid’s college fund in there. Like it’s going to be fully funded to whatever school now. Thanks to your advice. And you’re like, please, no!Packy: [00:04:43] Exactly. It works through, I mean, like the whole thing. And one of the things that I’m nervous about, frankly, is that the way that I write and the things that I write about work really, really well in this ridiculous bull market that we’re in the middle of where every tech stock is just totally up and to the right where I could throw a a dart at a dartboard and then pick a stock in that way.And probably it’s going to go up a little bit and then I can look smart. It’d be really interesting to see just kind of what general. Reader interest is at a time when the market is a lot more boring or flat or down or X, Y, or Z thing when the market changes. I feel I’m lucky that we’re in this spot right now that the thing that I care about and enjoy writing about the most is also the thing that is doing the best in the market. Nathan: [00:05:26] Well, I think it would be interesting because if I’m, I might be reading into this too much, but you’re trying to write about the longterm. Things that make the company and the business model and the strategy interesting, rather than like what the stock is going to do this week or this month, or even quarter this year.And so that would be like, you don’t want people taking away that like right about on Monday, it’ll make money on Tuesday. That’s the wrong thing. It’s more of like, Hey Twitter as a whole over the next year. Five 10 years is probably undervalued because of all of these things.Packy: [00:05:56] A hundred percent. Yeah. And that’s the way that I approach it.And then what ends up happening? I think particularly because there have been things like the Twitter or Slack or whatever else, what ends up happening is that people just buy the next day. Cause we’re like, cool. I mean, if it’s a long-term and so did up by big caveat always is that I have no idea what’s going to happen in the next month, day, year, week, whatever but term, I think these companies are in a really good spot and I think.People in the markets are just not used to companies with as massive a Tam or a massive, a potential market to address as a lot of these companies have and the business model that these companies have. And so if these things do well, and I don’t think they’re constrained necessarily by even, Apple’s kind of current $2.2 trillion market cap, I think there’s massive upside and a lot of these companies, but yeah, for sure that will take a long time to play out.Nathan: [00:06:41] Yeah, that makes sense. I want to go back to. You know how the newsletter has changed over time. And maybe before that, what made you start a newsletter in the first place? Packy: [00:06:50] Yeah, so I actually, so it was a company called Breather, which did kind of on demand meeting and workspace loved it, but was there for, you know, I was in year number six when I started the newsletter.And so I think after you’re at a startup for that long, it gets a little bit stale. We brought in a professional exact team, which made it a little bit staler and I was like, man, I need to like. Exercise my brain a little bit, because I’m not getting that at work right now. And so I took David Perell’s Write of Passage course and loved it as part of that. You know, one of the assignments was just go start a Substack. And so at that point I probably had 300 followers on Twitter. this was April, 2019, so 300 followers on Twitter and. you know, nobody obviously subscribed to the newsletter. I had to beg the first time I set up my stuff at Substack I sent out a tweet please, just like, I need to get 20 people to subscribe to this.Like, please just sign up. So I don’t have to ask people individually. And so that’s, that’s kinda how the whole thing started and really it was this exploration for the first year or so where I was just sending links. And sometimes I’d go a little bit deeper on something, but it was things that I was listening to and reading.I think it’s a really good way to start doing that and kind of summarizing other people’s work and getting that muscle. In the beginning. I was petrified. Every time I hit send, but like there was this text chain going on among my friends. They were like, what is Packy doing? He went to a good school.He worked in finance for a while and now he’s like, he’s sending this newsletter every Sunday, just random internet links. Like what the hell is going on here. but did that for a awhile while it was in the middle of starting a company, never thought that it was going to be my, my full-time thing.Company was like Bri, they’re kind of a physical place base thing, left breather kind of at the end of 2020, or the end of 2019 to start that. and then COVID it. And so I was like, Oh man, all right, I’ve grown this newsletter to like 350 people now. And that is like the asset that I have professionally because this company is at least on pause and maybe dead.And so let me just see if I, you know, reading this thing from per my last email, which was called to Not Boring and start writing some essays, like. Could this be enough that it at least pays rent and gives me time to figure out if this company is going to be the thing that I do, like pretty much anything to help me avoid getting a job.And so set a couple of, kind of short-term goals for myself. Like, all right. Hopefully I can get to, I think my goal on January 1st, 2020 was let’s get to a thousand people by the end of the year, then COVID hit and it’s like, let’s get to 5,000 people I’ve ended the year. And then the goals kind of kept falling and it kept growing.And so then like at some point in the summer, I realized that this is probably what I want to do full time. So I was like, you need to start monetizing this thing. And so then I figured out, like, could I, you know, should I go paid or should I get a sponsor? And if I get a sponsor, how do I do that? So just put together a deck and tweeted that out and got sponsorship interest.And so it’s been a series of like, none of this was intentional and I never set out to be a professional newsletter writer, but. Each step along the way. I think even as kind of the list grows cooler and cooler opportunities open up. And now I feel like I’m in a spot where I get to do this thing that I really liked doing and have all this serendipity with no real plan.Nathan: [00:09:50] Yeah. I love it. It’s fun to see how that’s grown. It’s crazy that, so what, in, in 10 or 11 months, you’re up 30,000 subscribers. Is that right? Packy: [00:10:00] Something like that. Yeah. Up to 33,000 now. Nathan: [00:10:04] Yeah. Okay. It’s, it’s crazy how fast, newsletters can grow. And we were talking about our mutual friend, Mario. Who’s going to come on the podcast a little later and you know, he’s grown incredibly fast and, and just sort of this thing of when you’re putting out great content, then there’s not really a ceiling on how, how fast or how high the newsletter can grow.Packy: [00:10:23] Totally. And I think Mario is such a good example of. One of my favorite, like kind of meta hacks, which is just experiment a ton over the past year he has tried so many different formats has brought in a bunch of different collaborators. You know, sweat made the switch before a lot of people, which I think is coming from Substack over to ConvertKit He did all of these things first.And I think more than even actually what you try, just trying new things is such a valuable thing to do in growing and growing a newsletter. So he’s been so much fun to watch. Nathan: [00:10:54] Yeah, that’s great. In that process, right. We’re talking about adding 33,000 subscribers in a year. What are some of the things that have worked?Packy: [00:11:02] Yeah, I mean, it’s really, frankly, most of that has just come from people sharing the newsletter, which has been great. Like my main two toolkits are spending a ton of time writing and then tweeting about it and that’s like, Really most of the plan in the beginning when I was at like 500 and figuring out how to get to a thousand, I made a list of a hundred different things that I wanted to try.I tried a few of them actually had a friend who was leaving his cushy job, come and help me for a little while. And we did a few things like put together a referral program, which is good, but a lot of effort, We launched on product hunt, which was huge. I was at a thousand subscribers. Then we launched on product time, just put together like a very simple landing page, just as an excuse to go on product hunt that got to, I think 2000 plus people in a few days went from 1200 to 30, 200, just from that product, something.And then. From there. The biggest thing was, you know, even when it was, I think 200 people probably I started saying like, all right, I’m at 200 people. Here’s the chart. Like next week, I’d love to be at 210 people. And I think just being that kind of open with everybody from the time that it was very small, has just built this feeling that we’re all in it together, which is totally true because none of this growth happens without people.Responding giving feedback and sharing and all those types of things. So that’s really been, frankly, the big thing I know, community is an overused word. And certainly like, this is more, I guess, technically an audience and a community. Cause they don’t have a Slack, but I don’t have any of that. But all of the growth has come from people reading and talking about it and sharing.Nathan: [00:12:29] Yeah. That makes sense. I love the way that you’re inviting people along for the journey. Like so many people. Take like a, I am the expert. I will teach you things as the audience, you know, or, or that sort of thing. And I’ve just always loved it when someone says like, Hey, I’m a guy I’m trying to get from here to there.You know, if you want to subscribe, that’d be great. If you’d tell your friends that would help me hit this next milestone. And I mean, I did that in the very early days of ConvertKit where. it actually started with what I called the BA the web app challenge, which was trying to get to from zero to $5,000 in MRR in six months, and like blogging the whole way along.It didn’t hit the goal, you know, in the short term, but it worked out in the long run. and I just think that more creators could bring their audience along for the journey. Packy: [00:13:16] Totally, and I think a huge part of this too, is like, you know, I saw people that I thought were just these, like, gods, right?Gods and goddesses who had big audiences. And, you know, we’re always in the conversation on Twitter and got hundreds of likes and everything they did. And I was like, I doubt I’m ever going to get there. But in case, like, let me just kind of timestamp all of this stuff, because if it works, then, you know, I can show people that I’m a random idiot sitting in a basement, somewhere writing a newsletter.Like you could also be a random idiot doing this thing that you want to do, whether it’s writing a newsletter, doing something else. I think it’s so cool to be able to just kind of timestamp everything. Along the journey to show that this is not some like mystical thing that happens. It’s just about putting in the work over time and having fun with it and finding something that you really like doing, I think.Nathan: [00:14:02] Yeah. And I think the approach that you’ve taken with the content of, you know, making the switch from just like, here’s the things that I’ve read recently to actually doing, you know, long form essays, trying to make them Not Boring. I think that’s, that’s. Paid off really well. Are there, I want to hear more about your writing process, right?So you’re publishing twice a week. Is that right? Packy: [00:14:22] Oh, usually twice a week. Now that was kind of accidental at some point I was. So I write every Monday I read kind of like my feature essay of the week. Typically it’s about a big public company, sometimes about a broader trends. So today’s piece on valuations was about a broader trend, but last week was Twitter.There’s a Slack piece of Facebook. There’s a bunch of just deep dives on a company. And then on Thursday, Probably yeah, six months ago. I was like, maybe it’d be nice if I do go sponsored at some point to have a second spot. And I want to be able to bring other people into the process and they want to experiment and all of these different things.So I opened up a Thursday that I really thought was going to be like, maybe once a month I have a guest or something else. And those that filled up. So Thursdays, I do. investment memos on startups that we’re investing in through the syndicates. So Not Boring now has a syndicate that invests in startups together, or a sponsor deep dives, which is a company will pay me money to write up the company.And that’s a fun one to dive into too. And I think goes pairs nicely with kind of letting people in on the process the whole time and, and my thought process on. Like, obviously I could be writing something that I don’t believe in here or whatever, because they’re paying me a lot of money. So you need to really trust that I’m only choosing companies that I actually would write about anyway, even if they weren’t paying me and then I’m writing honestly about it and all of that.So Thursdays are mainly those two things, and then sometimes I’ll have a guest post. So this past Thursday I had Dan Tran, who was the CEO of manage my Q a, write a piece on third-party food delivery and, and. Kind of like the impact on restaurants that we’ve seen over COVID from restaurants having to pay 30% of their profits to third party delivery companies or their revenues, I guess, and what that does to their economics and what a better way forward is.And so Thursday still is kind of this experimental thing, but mostly is, you know, the best memos and, and deep dives. So, yeah, so it ends up being a ton of writing. It’s like, you know, I’m writing probably 10,000 words a week, which is not. Something that I thought I’d ever be capable of. Nathan: [00:16:27] So. Yeah, well, I mean like this, the first thing when people talk about, Oh, I want to, I want to start a newsletter.You know, maybe they want the Twitter engagement. Maybe they want to be one of those gods or goddesses that they look up to. And I’m always asking them like one that’s amazing Two you’re totally capable of it. Three. Do you know just how much writing is involved in that? Like just to set the stage, like you’re signing up To be a writer as your profession. And sometimes they’re like, yes, absolutely. I have this background in journalism or whatever else, like. I can nail it. And other times they’re like, Oh, okay. I thought that the polished thing was just what you, you know, like that was the process. Packy: [00:17:03] Totally. Yeah. You remember essays that you had to write in college, like imagine doing like that final paper twice a week now.And that, that’s what it is. I was talking to somebody, on Twitter the other day, somebody that I quoted in my piece today and we were talking and he had to write something for a job interview. And he was like, man, like I really thought this newsletter thing was cushy until I had to write one thing for a job interview. And I was like, Oh man, this is really, really hard to do. Yeah. Nathan: [00:17:28] It’s, it’s fun to see how, like so many people develop that muscle though. because it is just a muscle. I think, you know, we put a lot of great writers on pedestals and that’s because, they’ve done the work.They’ve learned how to do it. It’s it’s, you know, it is really difficult, but at the same time, I think it’s pretty approachable. And I, I think people like you and I prove that. Look, if you’re going to sit down and put in the time. You can put out content, you know, I’m not going to win a Nobel prize for it, but a lot of people are going, yeah, sorry. I didn’t mean to cry. Packy: [00:17:58] That’s my goals. Now I think that the Nobel Nobel prize was, was really what I was after with this, this whole thing. But I think you’re absolutely right. Right. Like it is about sitting at your computer for hours and hours and hours every week and making sure that you’re getting it right.And that you’re finding the right angle. I think so work is the number one piece of it. I’d say the other thing that you need to do. Is find something that you actually care about writing about and not fake it, because I think it’s impossible to put in the work if you’re not interested in the things that you’re writing in.So you can probably fake it for a little while, but I think it really comes through when the writer is really interested in the things that they’re writing about. Nathan: [00:18:39] Yeah. That makes sense. What’s more of your process on researcher stories that you put together? You know, I talked to someone with, I’m asking purely for myself because I’m trying to figure out even more of my system.Right. I hang out with someone like Ryan holiday and he has this crazy like note cards, you know, in folders and all, you know, as he’s writing all these books and I’m like, I have Apple notes with an assortment of random ideas that I jot down in there. And sometimes they make their way from like, Idea to rough draft and on from there, but I’m curious what, what your process is.Packy: [00:19:12] Yeah. You’re more organized than I am. So I, I use, I use Roam because I think that you’re supposed to, and that at some point, like all of my backlinks are going to start coming together and like, My mind is just going to start working like humming my second brand. I guess it’s going to start humming here once, once my room starts working together, but frankly I have like something called Not Boring ideas where I put in a new tag.Whenever I have an idea. I think maybe once I’ve gone back to that list, it’s probably like 35 ideas long. And so I’m like, okay, cool. Like I have this backlog of things that I might want to write about. And then every week on call it Wednesday for a Monday essay, I’m like, All right, let’s go look at the list.Like, what should I write about this week? And they all end up kind of seeming stale. And so every Wednesday or Thursday, I sit there like panic thinking. I have no idea. I’ve written about every company that I’m interested in. I’ve written about a return that I’m interested in. Like, I think Monday is the day that like, I’m just not going to have anything to say.And so at some point there, I spent a lot of time on Twitter. I see something that interests me or reading something else. I see something that interests me. I wonder if I have a unique angle to take on that thing. And then if I do. I had set up to kind of a Google docs. I set up like the, you know, V1 draft doc.And I said at the outline doc, And I’d probably dump a few links in some, some in Rome and then some in the Google backs than there are all over the place. And there’s nothing kind of special about it. And then I’ll try to do an outline and I’ll probably get like four bullets into the outline. And then I’m like, I’m just gonna start writing.And then I started kind of just writing the piece and hammering it out and doing a lot of the research kind of on the fly exactly how you’re not supposed to do it. If they were teaching this in college where they’d say like, look at all the evidence first and then like figure out if there is an argument to be made there.They’re not like. Certainly looking for confirmatory evidence, but also I’ll ask like smart people around me who know more about the subject than I do. Like if I’m totally crazy on this, or if there’s actually something there and really look for, you know, things that will disconfirm what I’m thinking as well.And certainly just cause I’m maybe a coward, like we’ll caveat the hell out of things that I’m not certain on as I’m, as I’m writing them, then, you know, like there’s this panic and ecstasy and whatever the whole kind of Wednesday through Sunday. Again, if you, if you want to. Really get a newsletter writing.Like I have not, I’ve taken one day off, I think in the past year that I’ve been doing this full-time cause every Saturday, every Sunday, I’m just kind of like sitting there writing. and then, you know, at some point I’ll have a draft that I don’t feel terribly embarrassed sending to my brother and my wife, my wife, her job as editor is to kind of say like, you know, this was interesting to read or like you do not have this yet.And my brother is, is to be a younger brother and just totally rip apart. What I’ve written and tell me when I sound like I’m too full of it or whatever, throughout the paper. And then also like grammatical stuff, or things that I’ve missed or different things. Like, luckily he’s also, he works at a company called Parade.So he’s also kind of in the startup space. And so he like knows also the material and the conversation that’s going on. And so it can really help there he’ll do that. Meanwhile, like half the time I’m probably in Figma just making terrible graphics because they help me think through things as well. I throw it all together, dump and stuff, stack.On Monday morning, I do another read. I’m like, ah, this is good. Or this is terrible. I don’t know. Try to make some last edits, record an audio version of it and hit, send and violent eight 55 in a cold sweat every, every Monday morning. And then do the same thing on Thursday.Nathan: [00:22:38] And then just rinse and repeat every week.Packy: [00:22:41] Every week. Yeah, I’m actually 12, but I look 34 because it’s aged me. Nathan: [00:22:49] What do you think about like, there’s this thing with newsletters that I think everyone should be aware of is sort of this hamster wheel you can get on and you have to be, I don’t know if it’s careful of, and but maybe just know what you’re signing up for.You know, we always talk about the incredible upsides of growing a subscriber base. We’ll get into revenue and business models in a second. and, and the upsides are phenomenal, but one of the downsides is that. You know, you are showing up, you’ve spent all of your weekends, you know, or at least consistently every weekend for a while.Right. Of working on these posts. And so I’m curious how you think about those trade-offs and if you’re looking towards systems to try to improve that in the future.Packy: [00:23:28] Yeah. I mean, thankfully I have an incredibly patient wife, we just had a baby, so that adds another level of complexity and, and happiness and all the great things to it as well.But. I don’t know. I mean, I, I really genuinely enjoy doing this, so I don’t mind it. It’s more about thinking about the other people in my life and being like, I wonder if they mind that I’ve been in the basement for the past seven days, just writing and chances are they probably do. But the good thing is, you know, there are times throughout this process that I have nothing, you know, like I’m just sitting there and I’m blank. Then I can go hang out with the baby for three hours in the middle of a Wednesday, which is really, really cool. Or, you know, go to dinner with my life and not kind of have a set schedule knowing other than the fact that I know that Sunday, I’m going to be totally panicked and spending all day writing throughout the rest of the week.It can be a little bit more all over the place. My wife and I keep having this debate about. Whether or not, I’m inefficient. And like, certainly like she’s an operation. She’s the most hyper-efficient person in the whole world. Whereas I’m like certainly spent a lot of time just kind of scrolling Twitter.But I can, I think when you’re a writer, you can really justify an awful lot. It’s like working or research or whatever else. And I, I lean on that and I’m like, what do you expect? I’m an artist. Like, I can’t just sit down at a keyboard and just type on ton demand. So, you know, there’s a little bit of that.And so I never feel like, Oh man, I just worked. I was in investment banking out of school. I’d never feels like that where I’d feel like I’m just stuck to something and I have to be there, but in the daytime, it’s really like, I really liked doing this and it’s a little bit flexible. It’s all on me. You know, it’s all on yourself, which is is one of the good or bad things about this. It’s like, there’s no one else to blame. There’s not a boss making you do anything. The downside, obviously, is you can let that run away in terms of systems, I keep making excuses for myself there too, where I’m like, I don’t know. I’d love to hire an intern.I think it’d be really fun to have an intern, but I don’t know what I would have them do because like, like I said, I sit down on Thursday with no idea what I’m going to write about. And so I can’t tell somebody to pre-research. So much of the research happens in the process, or if I get an idea as I’m in the middle of the sentence and I go look something up, so it’s really hard to plug somebody into that.So I I would love to put systems in place around this. And at some point I’ll have to, but for now I kind of like, you know, just the rawness of going through it every week. Nathan: [00:25:53] Well, I think it comes through like the rawness combined with the interest and excitement comes through in the writing, you know, and that’s what makes it exciting.And I think there’s probably a version where you can be like, We have planned out our content schedule three months ahead. And you know, all of these things and every article was perfectly researched and all of this, you know, and whatever else and people would be like, Packy I don’t mean to say anything bad, but this latest one was a little bit boring, you know?And then you’d be like, Hey, you know, this way we can guarantee, that it lives up to the name. Packy: [00:26:23] Totally. I mean, doing it this way, at least you can piggyback on a lot of the things that are happening. And so I think that’s part of the growth thing too, is, is just being in kind of the conversation and knowing Oh, wow.This week, people really care about Twitter because they acquired Revue and they’re launching spaces and they’re like maybe making this play for the creator economy. I wrote that they should do this a bunch of months ago. now it feels like a time for me to jump in and do this, this piece.And so having that flexibility allows me to Do something people, are going to be interested in because they’ve been talking about it a lot that past week. Yeah. Nathan: [00:26:56] That makes sense. another side effect that we see. Well, so, um, another newsletter author. Who’s, she’s going to come on the podcast later, Legion, she had this line about, how her paid newsletter, is her, is her like LP update list, right?I’m talking about how, as an investor, you know, she has this newsletter that, is generating. You know, deal flow and revenue and all of that. I just loved the line. but I’m curious how, you know, as you’ve been investing in starting a syndicate and all that, how the newsletter has played in. Packy: [00:27:31] Yeah. So Lee and I were actually just having this conversation a couple of days ago about how investing and writing are just like two antithetical processes. They work really well together. The results work really well together, but the processes are so different, right? We’re writing. You want to be sitting down with a bunch of time to just think and not have a bunch of meetings. And then the investing side, you always want to be meeting people and helping those companies in any way that you can, once you have invested.And it’s like this very kind of unstructured time where if somebody is like, Yeah, we’re, we’re racing around and we’re closing on Friday and can you meet and diligence it and put it up on AngelList and do all of this. And the next three hours, it’s like, I’m going to figure out how to make it happen, but it totally jams that like kind of two day window that I’ve given myself for the writing.So from a process perspective, they do not work together at all, but from a results perspective, like I have no business being an investor, having anybody kind of trust me on my startup investing ideas. I’ve probably done between the syndicate and personal investments over the past six months. 12 investments.Like I’m not an experienced venture investor, but because I’ve been writing for the past year, twice a week, and like putting my thoughts out there, people have a pretty good kind of corpus of the way that I think about things. And so they can think. All right. Packy, like probably has thought through this in a similar way to all the other things that he’s thought through.And so either I think that’s stupid and I’m not going to invest with him because it’s out there. And I think he’s an idiot or, you know, at least like, know the way that he thinks. And I appreciate the way that he thinks. And so I’m sure that he’s thought through this one, the other benefit of this for the company is because we’re Not Boring.I’m pretty nakedly commercial about the whole thing. It’s a little meta where we write about business, but then like really building this business and. I hate to use billing and public, but building this thing in public where like, like I said, I can write these sponsored deep dives and people actually really enjoy them because I try to write them the same way that I read a normal piece, write an investment memo where 90% of the value that I’m probably going to add to a company that I invest in comes on day zero before I even put any money into the company.Cause I’m like, look, I’ll send out. An investment memo on your company. If I’m excited about it to a list of 33,000 people who are all in tech and finance. And so you’ll probably find some hires, you’ll probably find other investors. You’ll definitely find customers. And that’s a huge part of the value is just being able to help the company tell their story upfront.So from that perspective, I wouldn’t get into half the deals that I’ve been able to get into. If I weren’t writing and path is maybe being. Generously, maybe I wouldn’t have gotten into any. Nathan: [00:30:05] Yeah. I mean, it’s fascinating to see so many, angel investors, venture capitalists, see writing and building a newsletter as like one of the most effective forms of deal flow and like online, a lot of what we’re doing is just trying to, to gather attention, right?So we’re, we’re putting out articles, we’re putting, you know, essays, Nike’s putting out ads, all of these things, right? We’re, we’re putting out our best version of content so that we can get attention. And then it’s what, what can you channel that attention into that has, you know, the most enjoyment for you and the highest return and like, you know, that’s where people joke that Nike is an advertising company that just happens to sell shoes.Because they found out that was more profitable than, you know, like being the next Wieden+Kennedy and just making ads for other people. Now that’s apocryphal. That’s not actually how Nike came to be, but you know, that’s how I think about it. And so w when you have this attention, you could monetize it through sponsorships, through paid products.Or as, a lot of investors, I I always read to Tomasz Tunguz from Redpoint and he’s had this newsletter going for a long time. It’s totally free. All these things. He’s not launching a paid newsletter because he’s like the deal flow into Redpoint is the highest possible return that I can get.And so I think it’s amazing to see, you know, like angel investors like you and I be able to do the same. Packy: [00:31:34] Totally. I mean, it’s, it’s been fascinating to where. But that’s one of the main reasons that I want to keep this open is because it does just kind of create this surface area for opportunity and for new people reading it, who might be starting a company, or want to share a deal that might be interesting or all of those things.But even the sponsorship itself has helped me find investment. So companies that have sponsored deep dives Daenerys around, and now I know the story and I’m really familiar with the company. And I know the people on the team because we’ve worked together on the thing. And so either I try to get the syndicate in, or if I can only write a personal check, then I’ll do that.But yeah. Even just like that the sponsorship piece is also great at generating deal flow. So the whole thing just seems to work together really nicely. And I don’t want to think too deeply about the business model beyond this because what’s happening is working and I’m sure other things that feel natural.And, you know, I think the number one thing is like, keep the audience’s trust and keep them engaged and keep writing good stuff. And if I can find other ways to monetize that fit with that. Awesome. But I don’t know, we can talk about the sponsorship thing versus paid, but one of the most fascinating things to me is that like consumer sponsors have come, like let’s call it a hat brand and that’s not a natural sponsor, but if a hat brand comes, I’ll actually sell.Fewer units or get fewer clicks to that hat than I would to a $2,000-a-month SAS product, like just by number of actual orders that have gone through. And so figuring out kind of like what people actually care about then allows me to kind of build a monetization around. The content that people want to read.Nathan: [00:33:08] Yeah. Well, I want to dive in. There’s more because, for a long time, people have monetized newsletters by selling products, and sponsorships. but then in the last say 18 months or two years paid newsletters have really had this rise. And, you know, you were on Twitter last week talking about like, yeah, sure, that’s awesome. But I think sponsorship is a really underrated, method. And so as you think about it, like you could launch a paid newsletter right now, it would do very well. you would have that recurring revenue. and so I’m curious, you know, like make the case, why, why are you staying with sponsors?Packy: [00:33:42] So I ran the math when I was thinking, when I kind of hit 5,000, which was like, my I’ll get to 5,000 and then I’ll figure out monetization. So I started thinking about it, then didn’t monetize till 10,000, but I was like, all right, cool. So the 5,000. Substack says that you can probably get 10% of your audience to convert.I’ve never met anybody. Who’s converted 10% of their, their readers to paid. So let’s say it’s five. So if I get 5% that I’m at 5,000 times, 5%, I have 250 people subscribing. And if they pay me, I don’t know. Even if generously, they pay me $10 a month, then I’m at $2,500 a month. And all of a sudden, either I need to find like three more days in the week to write that paid piece.Or I’m putting something behind a paywall. And so this growth that has been like the most fun part of this newsletter from, you know, it was more of like a game kind of than a business. When I was just trying to grow it from a thousand to 5,000, I never thought I’d actually make money on this thing. so at that point I was like, what am I going to shut off the growth or not sleep and write it there.Another piece. And the count, the quality of all of them will probably suffer from adding anything more. So we’ll be in a spot where I’m making $2,500 a month growing more slowly. Not having people to share and talk about it, not opening up that surface area to other potential opportunities. It just like, you know, it’d be maybe a nice side thing if I weren’t putting as much effort into it, but that’s not, I can’t feed a family on $2,500 a month.Whereas you know, the 10,000 I, I sent out a deck on the sponsorship side, filled up. This was end of August, pretty much from a tweet thread filled up the rest of the year, in terms of sponsors. And like didn’t know sales efforts. And like, that’s one of the downsides of doing sponsorships is that if there’s not that kind of pull, then you have to like go out into the market and cold email people.And that takes more time. It’s a painful process. And I really like marketing, I guess, more than sales. I like just putting something out there and seeing what comes back versus having to ask anybody for anything I’m not petrified of, of that. so, you know, filled up to the end of the year, I was like, cool.I’m at least like making money and can prove to my wife that. There is a path here. If I start bringing in some money and then that started working really well and sponsors started telling other sponsors. And so this year, you know, there’s really like three formats that, that I do for sponsorships. I have my kind of Monday top of newsletter sponsorship.I have my Thursday, top of newsletter sponsorship, and I do different rates for the two of them because Mondays typically get shared a little bit more than Thursday pieces. Do. And then as I mentioned, I have the Thursday deep dives. And so with the three of those I’m now, you know, at least my run rate is more than I was making as an executive startup that raised a hundred million dollars and also have the investing piece of kind of like recreated a really good startup comp package through the syndicate and through the sponsorships.Nathan: [00:36:32] Well, that’s interesting. I hadn’t thought that you have both the salary replaced and then of course you, you know, you own a hundred percent of. You know, your, your new immediate business. but you also have the equity side covered because you’ve got the syndicate and the other investing. Packy: [00:36:49] Exactly. And again, this was like, you know, it could seem in hindsight that there was some plan where I was like, I’m going to synthetically recreate a startup compensation package, but it was really halfway through.I had spoken to a friend of mine who was launching a company. and trying to raise money and wanted to help telling his story. And so we experimented with me sending out an investment memo and sent the demand to somebody else and it worked. And so, you know, decided to start the syndicate and then halfway through, I’d probably three deals.Then I was like, wow, this is actually kind of like, I have equity and I’m making money on the sponsorship. This is kind of like, you know, what I was making before. And so now it’s kind of there, which is, which is great. And the fun thing about it is there’s not. Upside thing. I don’t have to go to my boss in a year and say like, all right, you know, it’s, it’s the new year.Can I get a 3%, 8%, whatever raise it’s. It is a direct result of how quickly the newsletter grows and how effective it is for sponsors. Nathan: [00:37:41] Yeah. That makes sense. So what are you charging for those different sponsorship slots? Packy: [00:37:45] Yeah, for Q1 Mondays or 5,000. There’s days are 3,000 and ER, Thursday kind of top sponsorship is 3,000 and the deep dive is 20,000 because that’s a ton of work and I think really good exposure for those companies.Nathan: [00:37:57] Yeah. That makes sense. Okay. So you’re pulling in a significant amount of money from this. Packy: [00:38:02] Yeah. I mean, like I’ll, I’ll do I’ll, you know, I’ll do package discounts on some of the stuff and all that, but you know, a good month would be. 30 so far, a good month is like 30, 40. and like I said, growing, so that, that part is awesome.Now there’s, you know, it’s also no cost, but there really should be. As I said, I should probably hire somebody and build an actual website and do all of these things and there should be the cost side, but right now it’s kind of like, The only cost is the fact that I’m spending 60 hours a week writing and then doing the other stuff on top of it.I love it. So that part’s great. Nathan: [00:38:35] Yeah. So, I mean, it’s just like a startup job in the fact that you’ve got the crazy long hours and then, you know, a questionable boss just in this case, the crazy boss.Packy: [00:38:42] Yep. Yeah, exactly. Nathan: [00:38:45] That’s interesting. So I think you’re underplaying the numbers that you would get from a paid newsletter.Like, I think there’d would be higher than what you, what you threw out there, but I don’t think they’d be higher than what you’re making off the sponsorships. Packy: [00:39:00] I, I think I agree. I think I’m more competent. I think it’s 20,000 recurring, 20,000 recurring, I think. Yeah. I think at this point with 33,000 people, I, I could, I could also do like a more premium price point now because like, I get the comment a lot, which is like, Yeah, like you said, I made money on some of the things you’ve written.This is, I’d rather read this than an equity research report and all of those types of things I could do, maybe a hundred dollars a month sponsorship that a few people decided to subscribe to. There’s a bunch of different ways to take it. But again, the big bottleneck right now is time. And the main source of enjoyment is having people kind of share and discuss the things that I’m writing and like have this conversation happened around the things that I care about and get to talk to smart people about them.So, yeah. I think the combination of the fact that it would be a little bit less than I’m making on the sponsorship side. and the fact that it would slow growth. I think those two things combined just make me want to lean away from that and then did a sponsorship plus because of stack charges that are cut on sponsorships and not on sponsorships, because they don’t want to, you know, they, they want to ignore the fact that sponsorships exist.It’s actually from, from a cost perspective. Pretty good. Nathan: [00:40:16] Yeah. I mean you’re saving 10%. yeah. Plus plus drive fees. Yep. That is true. it’s something else that is interesting with your sponsorships is a lot of people when they start entirely free and then go into sponsorships there. Like weirdly apologetic about it, of like, Oh, we’ll get to the content really soon.Like, I’m sorry that, you know, like, sorry for this interruption or whatever else. And you’re just like, boom sponsor right across the top. Let’s start with sponsor, you know? And like you’re not apologetic at all. and you’ve built that into the, the brand. Was that intentional? Packy: [00:40:54] Yeah. I mean, I think that comes with this whole thing of like, I don’t know, guys, you want to, I’ll see if I can grow this thing together and like help out.Maybe if you want. And then the next one was like, I do have a baby on the way and like a family. And so like, I’d love to make money on this. And so sent out, you know, before I, I got the first sponsor, I sent out the survey and said, I’m doing this because I want sponsorship and they want to know about you.And so that works. I chosen sponsors for the most part, for the entire part that they actually think. The audience would care to know about. And so, like, I got really lucky that public was one of the sponsors that the trading app, and then they’ve had this meteoric rise over the past few months. They were all over the Robin hood debacle, like the whole thing.So such a fun sponsor to get, to be associated with. They keep sending me cool gear that I’m like very proud to wear. And so, I don’t know, like as long as I’m choosing sponsors that I think the audience actually cares about, then I don’t feel bad about it. at all. And I’m trying to write, copy that, you know, that, that, the sponsors happy with, but the people actually enjoy.And so put it kind of in the same voice as the, as the newsletter. so all of that kind of works. Well. The one that I was a little bit apologetic about was the deep dives cause like that is really just like. Yeah. If I, I never pretended to be a journalist. I don’t want to be a journalist, but like I went to journalism school, they would pull away my diploma for saying like, yeah, you could pay me $20,000 and I’ll write a piece on the company.But I’m like from day one on those, I was like, here’s how this works either. I do a CPM where they essentially pay me because there’s a bunch of you here. Or I do a CPA where. They pay only if you click on something and sign up for something. and so like each time I do it, I’ll tell you which one it is.I’m not going to pressure sell you into anything, but like, just know that this is how I’m getting paid on this one. And then a couple of days, or one deep dive ago, I’ve just wrote up my process and put it in a Google doc and share it with everybody on how I choose the companies and what I’ll write about and how the writing process is with them behind the scenes and what I will, and won’t say, and like that I won’t just.Get paid to talk shit on competitors or like any of those things that it’s really like, please don’t tell these sponsors that I’m writing about something that I care about and would write about anyway. And they’re paying me all this money for it, because like that’s what I wanted to come across that.So I’ll do you know, I I’m bad and I I’d love tips on how to just manage my own email as someone who puts a lot of email out into the universe, like between email and DMS, like. I get a ton of inbound requests, particularly for the deep dive. That’s another one where even though it’s a higher price point, I get more demand for that than I do for a Monday or Thursday sponsorship.But I’ll just, if it’s a company that I don’t think people are going to care about, I’ll just kind of ignore them and then it, you know, it would just bad. but I just like, I I’m overwhelmed by the, by the inboxes and all sorts of different places between Twitter and mail and text and whatever else. So one screen is just that I’m an asshole and I’ll, I’ll just not respond to people.If I don’t think the audience is going to be interested. And then two there’s plenty of conversations that I’ll have with companies where I’m like, frankly, I think like you’d be a really interesting Monday or Thursday sponsor, but is your company doing anything like. Different that would be cool to write about.And it would be worth three or 4,000 words. And some companies are like, no, totally like we’re very straightforward business. And I completely understand that you wouldn’t watch her write 4,000 words on what we’re up to. And like, maybe we’ll come back and talk if you have a product launch or something coming up.But otherwise I think that’s helped that they’re very clearly companies that I would have written about anyway. Like you’re not going to see a state farm insurance. Sponsorship probably sponsored deep dive in anytime soon. And they’re probably on the more interesting side.Nathan: [00:44:32] Yeah. That makes sense. Well, I love kind of bringing things full circle.They like working in public, sharing the journey, bringing people along for it. And then that allowing you to actually generate more revenue because then your audience is like, I love that he’s got these sponsorships and that, you know, he’s putting them front and center. I love these brands are supporting, you know, my favorite newsletter and, and it’s completely the opposite of like, What a lot of people get of like, Oh, he’s a sellout or any of these other things.And it just goes to show you, bring the audience along for the journey. Then they’re in your corner a hundred percent.Packy: [00:45:06] A hundred percent like this one, and I’ll give them a plug, even though it’s not gonna this, this might not air until after I read it. But I’m writing about this company. Also IRA on, on Thursday.Yeah. Essentially that you set up a self-directed IRA, which means that you can do all sorts of things. Like I know that people who read not were in care about, which is take your 401k money, which is just sitting in like a mutual fund somewhere and invest it through Angeles, invest it into crypto, invested into masterworks, which I’ve written about and invest into all of these different things that I’ve already written about.And so like, That one is an absolute no-brainer because we have a syndicate on angel list. We’ve written about mastery. Like all these things just kind of like come together. And so I think that’s the other fun part about writing about things even on the sponsor side that I care about is that that then attracts other kind of like companies.So, you know, they came in when they saw a piece on masterworks. And so it all just feels, I think very natural because it is very natural. Nathan: [00:46:01] Yeah. Does that make sense? Something else that you’ve been doing, that I find interesting is you record the audio version of each article and you, you release those in separate posts.And that’s, I guess I’ve seen a few people doing that, where they have, you know, a related podcast or something. when did you start doing that? And, and what, what drove that? Packy: [00:46:20] So my pieces are really long, right? Like compared to a normal piece, the main feedback I got when I was doing these, like. One to 2,000 were links pieces.It was like, Oh man, these are really way too long. You should cut down. Even from one to 2,000. And then I went the total opposite way and I, I wrote, I think a 9,000 word piece on Facebook and the average length is like 6,000 words. And so I think it’s only fair to people who want to consume the content.That there’s an easier way where you can just throw some AirPods in and listen to it for half an hour, instead of like. Trying to schedule time in your calendar on Monday morning to read enough worrying. So that’s, that’s the Genesis of it. It is truly painful that most Monday mornings I’m getting up right now.I’m in Miami. We have our own place. I woke the baby up to kick them out of his room and recorded in here this morning. But normally it’s in my in-laws basement where we’ve been living for the past few months since we had the baby. And like, I’m just praying that like the water heater doesn’t turn on or that like somebody doesn’t run the water upstairs or like.That something doesn’t mess, mess up the audio. So it’s like really painful to wake up at six every Monday morning and do this, but it’s also open up this thing now where, like, I just kind of have a podcast and it’s like this thing that seemed hard to do before that, just because I hit plane published an anchor.Now I have like kind of descript anchor. I got my Yeti microphone over here. Like I have a little setup. And so now, you know, if I’m writing about a company, I can invite the CEO or somebody on the team on, and just have a quick conversation. I really liked that about audio, that it’s so easy to just kind of work with, I think, for the podcast, the audio version and for the writing itself, like part of the reason I’ve been able to do it is that.I don’t care about it being perfectly. I want it to be right, but I don’t care about it being perfect. And so like the audio quality sucks. Like if you listen to the audio quality on my podcast compared to anybody else it’s terrible, but I’d rather just kind of get started. And then at some point, like I’m starting to talk to audio editors now who can help fix that.Maybe they can’t fix that, you know, the hissing from the water heater, but can picks a lot of it and professionalize it. But I think the biggest thing is just like getting over the hump and getting started. And a lot of that stuff is easier than it would seem to just dive in and do. Nathan: [00:48:28] Yeah, I think that’s the right approach of whether it’s writing or audio is to start and then improve over time because the hardest thing is showing up and doing it consistently.And then everything else is like optimizations on that continual effort. Totally. Yeah. Okay, what else should we talk about when we get into platforms? You, I mean, you write about platforms all the time, so I’m, I’m curious for your take on the newsletter platform space. I’m obviously, you know, full disclosure to come into the conversation.I’m a little bit biased in that. I own one of these platforms. you know, you and I both talk on Twitter extensively, they now own review. I’m, I’m curious for your take on, on newsletter platforms as a whole and where all this is going.Packy: [00:49:12] Yes, I’ve been on sub stack the whole time could not be more grateful to Substack.Like I said, because I do a sponsor model and they ignore sponsorships. I paid $0 for the platform it’s free. I paid $0 for the platform on top of which I’ve built this business, which I am eternally grateful for. I now have my own custom domain and Not Boring.co. So like, like they’re making improvements and, and it’s.It’s nice. I think from a, like putting my analyst hat on perspective, they’re in such a tough, tricky spot. They have so many different types of writers on the platform who all want different things and who are all looking at the other types of writers. And so obviously with the past year, they’ve made a big push to bring on people.Who are journalists or NBA stars or who have kind of existing audiences and bring them onto the platform and do all sorts of sweetheart deals, where you’re getting, you know, libel insurance and maybe health insurance. And you’re getting a legal staff and you’re definitely not paying 10% if you’re coming on and they’re pulling you over from the New York times or somewhere else.And so there’s these like bespoke deals happening that the next class of people, which I’ve kind of put my self in, which are like people who have kind of built an audience there who are more like the business. Analyst type who are annoying and loud and like, like me kind of pontificating on what some stacks should do, even though I’m not there building the company.And like, we all see that that’s happening. And so always kind of gripe about the fact that there’s this 10% fee and that everybody’s going to leave, but I think that’s true. And I think another really interesting wrinkle there is that. In a Ben Thompson’s written about this. I think Benedict Evans has that, that you know, what they need to do is solve for discovery and help people build their audience.If they want to keep them a platform and keep people from leaking, once they’ve hit, you know, 10,000 paid subscribers or whatever that number is, or the math no longer makes sense. And I think that’s really tough because I don’t think, and you know, this better than I would having more of a bird’s eye view, but I don’t think people necessarily want newsletters.Right? Like, I don’t think people very often go to. Sub stack.com/discover. And they’re like, I’d love to find a new newsletter to read. Cause my, the 37 that I get right now, like aren’t quite doing it for me. I’m looking for that 38 that I think it’s going to do it. And so I think they’re in a tough spot in terms of bringing in new demand.And so that otherwise what you’re doing is like kind of pulling the, you know, the limited hours and attention that each. Reader has to different places. If you’re trying to solve discovery for the readers that you have on your platform. And so in the beginning, when I had 2000 followers or subscribers, like I was like, yes, I would love if stack helped me solve discovery.And now I’m kind of like, I think I’m in like the top 10 free, like, do I want them sending attention to other people? Cause like they only have so many hours in the week and don’t maybe, maybe they don’t solve this discovery thing and I’m happier that way. And so I, I think they have like all of those kinds of tensions up and down the stack that are going to make it really, really tough.They’re doing an amazing job. Obviously they reported numbers that are great and people are making a ton of money on the platform. And so all of that’s great. They’re hugely responsible for this boom and for what I’m doing myself into, like really, really grateful and have enjoyed writing on it. But. I think they’re in a really tough spot and I’m interested to see how it works out long term.Nathan: [00:52:31] Yeah. It’d be interesting that the discovery thing is fascinating because I agree with, what you were saying or, you know, quoting Ben Thompson and others talking about like, I think that’s where they have to provide value in order to retain people long term. It’s a problem that like, I have my notebook right here of like lots of time spent on.Is how can you solve this? Is it a way that it can be solved? Like looking to companies like Shopify and others that have found this balance between you own your brand entirely, you know, all of this. Oh, but you want a network effect with Shopify pay or shop pay, you know, and they’re pulling off some of these little things and that’s what I’m fascinated with of like, could we do that with ConvertKit?Also, You know, just playing around with clubhouse the last week or so seeing the audience sizes and that people are generating, like, you’ll see someone on a clubhouse who has an audience 20 times the size of their Twitter following. And they’ve been building Twitter for like 10 years and then clubhouse for five weeks or 10 weeks, you know?And how is that possible? Is there a mechanism that you could create in newsletters that could allow for audience growth of that size and. And I just don’t know. So it’s fascinating to look at.Packy: [00:53:43] I mean, I wrote about this last week, I think Twitter is in, you know, please Twitter product team, get this one right. But I think Twitter is in a really interesting spot here where they actually have a lot of people. I I’d say probably of their, you know, 190, monetized daily active users or whatever they call them. Like a hundred million of them probably actually want to consume newsletters. Like it’s a very kind of intellectual, da you set.And so they have this like thing where they know the tweets that you like, they know who you follow. They know all of these things, they know what topics you’re interested in. They made a big push around topics. And so could they push you to another newsletter or could they do a better job of alerting you that somebody that you follow actually wrote this longer form thing?And I bet you’d like the last 10 of their tweets. I bet you’d love to read their, their thing and subscribe and all of that. Who knows if you can trust the Twitter product team historically, I think it’s actually, it seems like it’s better now, but historically you would not have been able to trust the Twitter product team to get this right.Maybe now you can, but then to like turn those people into, you know, Twitter spaces, people, so you can have the conversation. I really do think they have this really interesting ecosystem. That’s not zero sum discovery wise, but I think, you know, I think otherwise it’s tough. I mean, I’d love to hear how you’re thinking about it, but you’d probably have to spend money to bring people in as ConvertKit you have to spend money to bring people in or convince writers to cross promote other writers, which is tough because there’s limited newsletter space.And it’s like, it just feels like, unless you have a lot of that audience, they’re already looking for new ideas, it feels like a really tough behavior to like force people into. Nathan: [00:55:21] Yeah. I mean, it’s so interesting because. I w I think I’ve done 10 episodes of this podcast, or so, and probably eight out of 10 people I’ve said that Twitter is their primary channel for growing their newsletter.Packy: [00:55:32] I certainly had writers cause I was thinking about a newsletter related fund back in the day. I think everybody who’s written a newsletter goes through this where they’re like, these are recurring revenue businesses. What if you just took on some debt and bought the things and whatever. So was thinking about that for a little while.And so, and survey people, and I think it was out of 40 writers, 9.5 out of 10. Twitter as their main channel.Nathan: [00:55:53] Yeah. And it’s wild. And so Twitter now in that and saying like, Oh, we are everyone’s distribution and discovery method and there are other channels, like, you know, I think you’ll see search KickUp over time as your newsletter is around for, for longer.And, and things like that. It’s driven. My newsletter is about 25,000 subscribers and, and probably a third of my subscribers come from search that long table over time. But still like, Twitter is massive and in there for everyone. And so Twitter saying like, great, we own the distribution channel. Why don’t we own the newsletter channel as well?So it’d be fascinating. Like, you know, from ConvertKit perspective, I’m like, are you going to make that open to more newsletters or is it going to be like, no, just review newsletters. And then does that become. In the same way that a lot of creators, like James, Claire for example, would write on his own site and then re-publish to medium and Quora like, is review going to become this place.Or something that people are republishing on to get favorable rankings in an algorithm. Packy: [00:56:58] And it’s easier. That’s the beauty of Medium. And even the beauty of something like Ghost as like probably the number one thing that I’m looking for in the next platform is the ability to take something from a Google doc and dump it into something which is actually one of strong points.The ability to take a Google doc, dump it somewhere else and have it pretty much show up the same way that it was in the Google doc and right. Review I tested when, when Twitter announced they bought it and I was like, I can’t do that on review yet. So I’m not going anywhere quite yet. Nathan: [00:57:27] Yeah. Yeah. That makes sense. I’m curious, maybe just as we start to wrap up who are a few of the other newsletters that you look to and who do you follow both for content and then also like for ideas on how to grow your audience. Packy: [00:57:41] Yeah. Oh man, this one’s so tough. Cause the newsletter community is, you know, is like. This very tight thing where I’m in a chat mood, a bunch of newsletter writers.And like they’re all my friends written really depends often on the topic. Like they have to save Ben Thompson. Oh, G has influenced a lot of, uh, you know, the way they write, but then, you know, Mario who we talked about, but then there’s like, they’re really, I think I probably subscribed to like, 60 newsletters.And depending on the topic, we’ll open each one and I’ve really tried to start going more niche into different things. So like, if I was writing about NFTs and web three, the other day, I subscribed to like three newsletters on that. So. I can see, you know, even if it’s just a skin what’s going on in that space, that I’m now becoming more and more interested in, or, you know, if somebody writes really, really good at it really, really well on social media and I’m interested in Twitter and Facebook, then I’ll subscribe to something very specific.So I have the people that I’ll just pretty much read whatever. And then I happened to my 40 newsletter friends, so I read a lot of their stuff. And then I’m starting to try to find more niches. And again, if somebody is. As disorganized as I am. This is as you would imagine a total nightmare, but I do manage to pull some good stuff from that.Nathan: [00:58:51] I like it. That’s good. Well, where should people go to, to follow your newsletter and all your musings on Twitter and everything else? Packy: [00:58:59] Yeah. So it’s NotBoring.co. That CO, which I just put live. that’s the newsletter. And then @packyM on Twitter. Nathan: [00:59:11] Sounds good. Well, thanks joining me.Thanks for hanging out. And everyone just goes, subscribe to the newsletter and follow you on Twitter because I am quite entertained. It’s definitely Not Boring. And, It’s fun to watch your growth.Packy: [00:59:23] Appreciate you saying that Nathan and grabbing me on this was a blast.

Today’s interview is with Nathan Baschez. There aren’t too many people more familiar with the creator economy than Nathan. He started his own company with Hardbound and was the first employee and VP of Product at Substack in the early days.Now Nathan runs a company called Every, which is a bundle of premium newsletters. In this episode we dive into how Nathan creates tons of high-quality content every week, and how to facilitate your ideas with a newsletter “mastermind” group.We also get into a great discussion about pricing and churn for premium newsletters, and what it means for creators to have Twitter, Facebook, and other big media companies getting into the newsletter game.Links & Resources Gimlet The Nathan Barry Show 023: Tiago Forte – Building a Second Brain & Lessons From a $1M/yr Newsletter scuttleblurb – A Value Investing Blog Clubhouse: Drop-in audio chat Andreessen Horowitz - Software Is Eating the World Slow Boring Substack Teachable: Create and sell online courses and coaching Gumroad Nathan Baschez’s Links Every Twitter: @nbashaw Episode TranscriptN Baschez: [00:00:00] At the end of the day, writing is an act of communication. It’s a good form of communication. When you have thought deeply about what you want to say, and you’ve really crafted it, but in order to get to that point, you want to start with the more informal, casual, everyday way of talking. I think the feeling that this is a fascinating conversation is the key thing we want to get to because that’s the spark that you’re trying to like recreate for readers down the road. Nathan: [00:00:29] Today’s interview is with Nathan Baschez. There aren’t too many people more familiar with the creator economy than Nathan. And so it’s really fun to talk to him. He’s got a great background. He started his own company with Hardbound and he was the first employee and VP of product at Substack in the early days.And he was at Gimlet Media for awhile. And now he’s running a company called Every, which is a bundle of premium newsletters. They’re really focused on incredibly high quality content. And this episode we dive into how to write great content, facilitating your ideas with sort of a mastermind group.There’s a fun discussion around that. We talked about Twitter and Facebook and others getting into the newsletter game and what that means. Otherwise monetize your newsletter pricing churn. There’s actually, it’s a great discussion on insurance. You’re gonna want to stay tuned for that. Anyway. There’s a lot of good stuff,So let’s dive in and I’d love for you to meet Nathan.Nathan. Welcome to the show.N Baschez: [00:01:20] Thank you for having me.Nathan: [00:01:22] Yeah, well, we can have the Nathan and Nathan talk newsletters show.N Baschez: [00:01:27] Two white guys named Nathan talk in the newsletter business.Nathan: [00:01:31] Exactly. We have all the diversity of newsletters represented right here. I just want to call it out right away. So I love, first at a high level for you to tell listeners whatever he is and, you know, kind of where it’s at right now and, and what you and Dan have done with it.N Baschez: [00:01:50] Yeah, totally. So Every is a bundle of business-focused newsletters. And basically we cover right now, mostly strategy productivity, and then we’re kind of getting into some industry specific stuff, but that’s pretty nascent. So we have a newsletter that covers the passion economy called Means of Creation.We also have some podcasts that we do that are kind of, they’re very related to the newsletters, but basically it’s just this cluster of people that work together to create cool stuff. But there’s kind of, a lot of, we don’t really publish anything under the Every name. We publish it all under one of our individual publications.And each of those are incredibly kind of like specific is the goal. and, the interesting thing about our bundle is we’re structured as this. Thing that we’re calling a writer collective where it’s somewhere between getting a job at the New York times and running your own paid newsletter, like, you know, on, on your own sort of like whatever convert kit or sub stack or whatever other platform.And it, it gives you some of the upsides of, you know, having an editor, having some financing, having some distribution, all that kind of stuff, that you’d get by working at a traditional media company. But. Unlike working at a traditional media company, you’re building your own creative vision. Like you’ve got the final say on edits and stuff.And you know, you have the most important thing is obviously the shared upside. So you get like a huge chunk of the profits. We typically split them 50–50, but it’s a little bit case by case, depending on like what kind of team we’re assembling around a specific newsletter. And sometimes there’s more than one, you know what more than one person working on one.But roughly it’s like a 50–50 split. And, we’re also trying to kind of come up with creative ways to split the IP. But anyway, long-winded way of saying it’s like this interesting kind of new experiment, at least interesting to me, a new experiment in how to structure a media company.Nathan: [00:03:31] Yeah, I love it. So, as an example, let’s say I have a newsletter that I’ve started, I’m running separately, and I want to come to you guys and say like, Hey, let’s do a paid thing together. You know, I don’t know. I’ve got 10,000 subscribers and I’m looking to join every, what does that look like as far as what are you looking for?And, and, you know, some of the more mechanics of that.N Baschez: [00:03:55] Totally key thing that it all starts with for us is we’re really focused now on. W things that wouldn’t exist otherwise. So if you’re starting, if you’ve got your own newsletter and you’ve got 10,000, you know, free subscribers on your email list and they love what you do and you know exactly what you want to do to, to, you know, create a paid subscription around what you offer, where you’re going to maybe write one thing a week, and now you’re going to write three things a week.And two of them are going to be for people who are paying or whatever. Like ma maybe it’ll make sense to work with us. I think that it really depends on kind of like, your goals, but we’re more focused on things where like, maybe we’re really helping you like really deeply edit thing. Cause there’s like a thing you’re trying to do that, that you really value this sort of like editorial feedback.And you’re kind of figuring out what you’re writing about as you’re going. or, maybe you already have a newsletter and you want to create a new sort of like. Version of it. That’s like, maybe it’s more researchy and we could like help find someone who like, can, can do some of that research or crunch some of the numbers or whatever.And kind of like build a team around it. or maybe you just want to show up and like, we can kind of cue up some, like you’re an expert on an industry and we like aggregated a bunch of news and we’re like, Hey, here’s what happened in the industry this week? Like, what’s important. Like, what does it mean?Tell us. And we’ll like record the conversation and turn it into a newsletter. Like there’s a lot of different ways. That we might work with people, but yeah, for the most part, we’re looking for things now, another way that things may not exist, otherwise it’s just literally money, right? Like if you’re a freelance writer and you’re, you know, want to start a paid newsletter, then you’re basically cannibalizing your, the kinds of articles you may pitch to, you know, I would say you’re normally getting paid like a pretty good fee for, and a lot of cases.And so it’s hard to get the subscriber base up to the point where it might make sense to do that financially. And so we could be like, sort of hopefully a better version of, of, of, the normal kind of client you’d sell to, because you’re really building your own creative vision and it’s building towards this sort of like profit share thing.That can be a great, like long-term long-term thing. So those are some of the examples of like, how we think about it, but really every project is kind of like. Case by case basis. And we’re really figuring out a lot of the patterns that, we think can scale and where we make the most sense. And, but the core of it is just w you know, as consumers we realized we really wanted a bundle of these kinds of things.Because you know, it’s hard to, there’s a lot that we really like out there, and it’s hard to subscribe to a bunch of it separately, and it’s really hard to discover a lot of it separately. but then also, just as writers, we just prefer kind of like working together, like really value, editorial feedback, feedback, feedback, and like developing ideas with people and kind of like creating a community and a culture that, can help unlock the best.I think people are meant to like operate in groups and that doesn’t mean every group needs to be structured as a writer collective or whatever. Like, you know, plenty of still a newsletter writers form their own sort of ad hoc groups. But this is just the kind of group that felt like it worked for us.Nathan: [00:06:47] Yeah, that makes sense. So we’ve had, for example, Tiago on the show before, and, and, he’s got a paid newsletter as part of every, so how does that work when you know, his main business model is courses, you know, and he’s mainly monetizing this newsletter. There is it individual articles he’s writing a little less frequently that are become part of every, or, or how does that work?N Baschez: [00:07:11] Yeah. So in the case of Tiago, his, yeah, he had his own paid newsletter for like a while and it was doing really well and had had a bunch of subscribers. but he felt like, you know, it could make sense to also offer it as a bundle. So you can still subscribe to . Newsletter independently, but basically we struck a deal with him where it’s like, okay, cool.Like if people want to buy as a part of the bundle, then we’ll share the revenue back to you from that deal. But in his case, a lot of it is really about the archives, because for years he’s been writing this great stuff, that’s behind a paywall. And so it was like sort of a win-win for him to, make content that’s still behind a paywall, but like gets discovered.Discovery from like a little bit of a new audience, you know? and then for us to have more great stuff behind her paywall that like is, is content we believe in, from a creator we really love. so that’s, that’s another one of those unique situations where it’s, it’s kind of a, it’s like, it wouldn’t exist without us or whatever.It’s like, well, it already did exist, but like, you know, the whole reason to do it is like, we, you know, Basically to extend his existing paid content, to like a new audience, and introduce his work to new people, but like keep it behind the paywall so that it’s not like he has to like, you know, make everything free and shut down the subscription business or whatever.Nathan: [00:08:22] Yeah, that makes sense. you mentioned any, a few numbers as far as where you’re at on subscribers.N Baschez: [00:08:28] Yeah, we, so we just basically we’ve been around for a year in some form or another before we, before we launched. And so we just hit the 2,400 subscriber Mark and, launched kind of like officially we had, we were operating sort of, it’s sort of weird, cause it’s like, we’re kind of joked that we were like in stealth, but we’re a media company and like publishing articles and building anNathan: [00:08:49] You can’t you be invoked N Baschez: [00:08:52] but like, you know, we were just like kind of a sub stack basically for a while. Right? Like, and then we’re a collection of sub stacks and then, you know, then we sort of launched it. We sort of said like, Hey, like, you know, we’ve been doing this thing for a year.Here’s kind of like the model. Here’s how it works, et cetera. but yeah, it’s kind of, it’s kind of funny where we, we, we had this name in mind, every cent for like a year and we were like built up this whole subscriber base. And then we it’s like, we just launched the company, but also we’ve been operating for a year.It’s like kind of weird, but anyway, it was fun.Nathan: [00:09:19] I think it goes to show that you can feel like you can launch these things, iterate, figure out what you’re doing, and you can have a clear idea of your end state. Like every right now is a custom built rails application. We can dive into that, you know, and talk about, more there. So you can know what it is and you don’t have to like, build exactly that before you can start working on it.Right? Like you launched on some stack, they handle the payments, it’s working, it’s growing, you’re getting subscribers. And then you, then you migrate everything. And it’s sort of, there’s some entrepreneurs who come in and they’re like, Nope, I cannot make a sale until I have a logo and business cards and everything.And you’re like, No you need, in this case, you need content and people to read the content, you know, you need a product and customers, and then you can iterate everything else from there. And it sounds likeN Baschez: [00:10:11] Yeah. Yeah, totally. And it’s just so, so important. And so core to our kind of like DNA is like first, just see if you can do the thing and don’t even worry that much about like what kind of response you get, just like you try and do it and like, see if it was good. See if you can do it again, do it three or four times.And okay. Now start thinking about whether or not. People like it and what people liked about it and how to get more of like a hit when you do the thing. And then once you do that, then you can think about charging or, you know, trying to convert people to paying. And then once you’ve done that, then you can think about like, whatever, more growth and like sustainable like marketing channels, whatever.But we try and do things very incrementally and very like step-by-step, just because there’s a lot of really important stuff you have to learn at every step of the way, and you just can’t learn anything if you’re trying to do everything at once, you know? So, it’s really important to try and like, you know, strike a balance between, you know, whatever, trying to like deconstruct the process to do just one thing at a time and like, you know, moving quickly enough, all that kind of stuff.Nathan: [00:11:11] yeah, that makes sense. Along those lines, I’d love to dive into some of. You know, those lessons that you learned, but maybe let’s zoom out in the newsletter industry for a little bit, which first of all, it feels a little weird that newsletters industry, I don’t know that a year ago or 18 months ago, anyone would’ve would’ve said that.But what are some of the things that you see that make newsletters great. You’re plugged into so many of these newsletters and I feel like you, and maybe you’re in your co-host on means of creation Lee. Are two of the most like plugged into the newsletter world, people that I know. And so I’m curious, what are some of the newsletters that you’re just like, I love these and here’s why here’s what makes them great.N Baschez: [00:11:53] Oh yeah, totally. I mean like the one that I always say first, because I love his work and also because it’s massively, I think underrated and under the radar still is, this guy scuttle blurb. So scuttle, scuttle blurb is, it’s, it’s a value investing newsletter, but it’s very, it’s like, it’s like literary almost it’s super well written and researched and each.Company, he analyzes, he goes super in depth on. And, it’s funny cause like there is a newsletter component to it, but it’s more of like a website kind of a thing. Like it’s like I think he uses member full and WordPress. uh, but the email, you just get like an email saying a new post has been published and like the headline in the first paragraph, you know?So it’s like any publishes them infrequently. Cause they’re super in-depth so, you know, maybe one a month or something like that. and no, it’s just so good. Like there’s some. There’s some posts on there, like, like about random companies that like, they’re not buzzy companies. Like there’s one, there’s one on Gartner that was just like, yeah.Like Gartner and Forrester. Like what’s the deal with those companies? Like, why is one better than another? Why do you want to grow faster? What’s the like competitive advantage or moat or defensibility or whatever you want to call it. Like. you know, and like he uses, I think the right amount of finance for me, you know, it’s not like overly financial or quantitative, but like the numbers are there and he’ll tell a story about how, like they were getting increasing, operating leverage, and you can see that in their cost of goods sold as the thing scaled, you know, like, and, and I will have to look up some of those words every once in a while, but like, it stretches me and just the right amount, you know?Just really an in-depth and good. so I love scuttle Barb. I mean, I can’t, I can’t not say Ben Thompson, because I think that the reason why I’m writing the kind of stuff I’m writing is, in no small part due to Ben Thompson. and I think through him, I got into like, You know, clay Christianson and Michael Porter and a bunch of other Hamilton, Homer, and a bunch of other people that really are more like academics or write books rather than are kind of in the current newsletter thing.But, in terms of like strategy theoreticians, you know, like that’s like the kind of stuff that I, that I really like. And, so I, I love, I love reading all those people. What else is good. just as in terms of like more kind of like current stuff, like media industry stuff, diesel links by daily at Chi media light by Mark Stenberg.Those are both really good newsletters. Just kind of like, what’s the latest, like what’s going on in media, kind of like quick, really, really voicey fun, kind of like tone. there’s yeah, there’s a lot of good. There’s a lot of good newsletters. There areNathan: [00:14:28] There are, it’s so much fun. The amount of content that is being produced right now from a unique perspective. And. And like the commentary that you’re getting in your ways, I think really fun. what are some of the things like as you’ve watched these newsletters that you’ve really tried to build into every, some of these, these takeaways, either from strategies that they’ve employed or, or like voice or any of those other things?N Baschez: [00:14:52] It’s so interesting. because like, I think we think about ourselves as like we deliver our posts via email. but we think about ourselves as like trying to write, articles or essays in most cases more than we think of ourselves, like a newsletter. But then like now we’re rediscovering some of the more newslettery elements of what we do are like, yeah, we could have some formats that are more like topical and timely and a little bit more like you’ve got a formula like every week there builds some familiarity, which I think readers really love, or, or even every day or more frequently than every week.And it’s been so fascinating to try and figure out the balance with the mix of what we do. The stuff that I feel like has worked the best for us so far is the stuff that’s more like we’re going to spend a couple of weeks polishing an essay, kind of a thing, and then we’ll deliver it via email to let people know that it’s out.But like, you know, I don’t know what percent of people like read it in their inbox that day versus go on the site later or, you know, whatever. we really think about it like, you know, like ideally looking back 20 years, it’ll feel like we’ve created something. That’s kind of like a modern version of a magazine or something like that with really high-quality feature writing.And also like more snackable kind of like shorter, more timely series. But, it feels like the feature writing is kind of like the backbone of all of what we do. and, at least. Definitely for my own writing. But I think also for, for other parts of the, of the bundle, that seems to be what people like best, which is so interesting because of people say like, Oh, you know, attention spans, whatever.Like, but people really like depth. Cause it’s, it’s, not about how many people find it. Okay. It’s about how many people love it, you know? And so it’s fine. If a smaller number of people like actually get all the way through, if the people who do get all the way through are like, this is so great. I’m so glad I’m like paying for this, you know, like that, that’s the, the core goal.Nathan: [00:16:48] Is there actually, I’m gonna grab something real quick. We have. So my, my question is, is there any plans to like, bring those into other media forms? Cause like, we have this I’m a creator we did in the first edition that was Island blogger, like coffee table books of the stories that we’ve done. And I was just thinking.You know, I imagine every subscribers, every subscriber, no subscribers to every, I don’t know. Yeah. we’d like, you know, to, to pick up, like, to have some of that in-depth articles in maybe a long form, yeah. In print. I was going to say in a hard bound format, which ties back to your previous company, what are you thinking on that?N Baschez: [00:17:38] Yeah, I think we would love to do that. One idea we had is like to do a sort of yearbook thing almost where it’s like every year we do an anthology that’s like sold at cost or something to subscribers. That’s kind of like, you know, there’s probably a little bit of new material, but we’re kind of like, here’s like the best of this year or something like that.I dunno. That would be cool. I don’t know. I don’t know what the right thing to do is with print right now. Our, our whole focus is really like. Building an editorial culture and organization because, you know, I think we’ve got the first year, this past year was really a lot about like figuring out a lot of the basics of like, are we going to do this at all?Or what are the, like the B, like how to basically, how do we work with people and what, you know, all of that. It’s like doing things for the first time. And now it feels like next year, And it kind of culminating with being on our own platform, honestly. And now it’s like, all the pieces are basically in place and now we need to like, kind of grow into it, you know, like, okay.Like, We’re on our own website, but we need to make it like amazing. And we’re, we’ve got like a team of people, but the team needs to really gel and we need to like go through a lot of cycles working together and like we’re writing articles, but like, you know, how do we write better and more consistently and all this kind of stuff.And like, we’re working with people, but how do we really recruit new people in a way that’s a little bit more structured and systematic. So. I think a lot of this year is about just sort of like fo doing the things we already do and like doing them as best we can and learning how to do them. Just like staying really, really focused. so, I forgot Nathan: [00:19:12] makes sense. Well, I mean, It goes into this idea of solo versus versus a team, right? With the rise of Substack We’ve seen so much of people making the jump from a big publication, right? Where they they’re part of a larger editorial team and then going entirely solo. I come from the world of, you know, individual bloggers, podcasters, where people have always been doing it solo.And now honestly, some of them are starting to, eye a team and say, Okay. I’m earning enough that I could have help. I can speak for myself when I’m working on a book right now, and I have an editor for it. And The times that I’m like, Oh, this is good. I’m a good writer. And then I submit it. And the editor just tears it apart.And I’m like, what are you doing? And then I go through all their suggestions and I rewrite it based on the areas they push me and I’m like, okay, now, now it’s actually pretty good. And so I’d love your take on, on this, this idea of solo versus team then. And when. Creators should think of yeah.Going one way or the other. N Baschez: [00:20:13] Yeah, this may be a kind of weird thing, but I think everyone needs a team at some point in their career and they may not always need the team once they really figure something out. But like, and the team may not always be literally a team, like of people that you are employed with or whatever, but like, I don’t think anyone can do it in a vacuum, and like start from scratch and be totally in a vacuum and then like succeed from scratch.Like I think people either have a good friend or like a, like a partner, whoever that, like, they are always running their pieces by, or they, you know, maybe used to work somewhere where they had an editor and they like learned a lot. From that. And then now that it’s a little bit less necessary, but they probably still have people that they send their pieces to and all that kind of stuff.It just feels like, I mean, I don’t know, at least for me there’s maybe there’s, but like for me, and for most people that I talk to it’s, you know, to create really great writing, it’s like, it’s, you need to sort of be inculturated in it. It’s like any other thing, if you want it to be a really great product manager, how do you become a great product manager or to be a great software engineer?How do you become a great software engineer? You have to be in an environment where you can see other people who are better than you doing at it and pick up how they do what they do. you learn all the little things to look for little, little things like, you know, Little vocabulary words, almost like, Oh, you know, these sentences don’t fully connect or like this section wasn’t really motivated, you know, like there’s just like little things you can kind of pick up on that, that I think you can incorporate into your own consciousness, but start somewhere else.That’s just like basic. Why are humans a special species of animal, is it because of like this cultural kind of like learning things? So we’re not born with it, like it comes from traditions basically. and you’ve got to get those somehow. so I think, I think everyone does it. then maybe, you know, our goal is to create a group that is very intentional about those intentions and spreading them and making osmosis happen.By, you know, creating structures that facilitate it rather than just like rolling on everyone to figure it out on their own. Or maybe, you know, I think that the sad thing is a lot of people probably come to the conclusion that like writing isn’t for them because you know, it’s hard and maybe they don’t get super positive feedback after publishing a couple of pieces or whatever.They think a lot more people would succeed if they had a little bit more support and accountability. and so, I mean, certainly for me, I don’t think that I would have written nearly as good of stuff as I wrote this year. Not saying it’s like, whatever, amazing, but just as good as it is, it would have been probably about 50% as good, if not less, you know, in terms of quantity and quality, than, than, than it, than it was because I had, you know, like Dan and Rachel, and there’s just like a lot of people who I work with on pieces that I really value their feedback.Nathan: [00:23:05] Yeah, that makes sense. I think even like in the range of things you could have, one side would be, it’s just you writing completely solo. And then kind of the next step is like the informal editorial advisory board, which is really just like four of your friends that you respect. I think about two of my pieces, that I’m proud of is the ladders of wealth creation and the billion dollar creator, which like, Barrett Brooks our COO at ConvertKit and James Clear.Who’s a good friend and part of a mastermind group for the last. Eight years. Like I riffed with them on those pieces for probably, you know, off and on for 3–5 months before it turned into the final thing. And then like they gave lots of feedback and some of the sections that I was the most proud of.They’re like, like just cut it out. You, you already said that in these two sentences, you don’t need to say it in three more paragraphs.N Baschez: [00:24:01] Yeah, totally. No, it’s crazy. It’s crazy how important that stuff is. And another thing that you said there that I, that stood out to me is, you know, especially for it took you 3–5 months or whatever you said to like where you were like kind of riffing and you’re, I think that. Period of distillation is so important where it’s like you have some time to think about something and to notice things and to pick up little you’re like accumulating little moments where each one individually is like, kind of interesting, but when you give yourself a little bit more time to like experience life and, and observe things and learn things and notice things that are all kind of gathering.It’s almost like a crystal having time to grow. And it’s like, you’re finding all these things that connect, you know, like that process is really important. And I think essays that come after that are way better than essays where it’s like, all right, I got three days, like, what am I going to write? You know what, you know what I mean?And I think a lot of times when people experience, the agony of writing it’s because they don’t know what they want to say. And, You know, sometimes you just need more time to like know, you know, and, and it’s really, but it’s really hard to do that. If you have your own solo paid subscription audience, like you need to publish something probably every week to make a paid subscription newsletter work.And so it’s pretty hard to carry that on your own shoulders. If you want to write the kinds of things that take a month of like, Chewing on an idea or whatever, and accumulating, insights or, or perspectives or whatever. but that, that, that’s the cool thing about the bundle is, people are subscribing for a collection of people rather than just one.And again, this is like nothing new. It’s like the new Yorker, you know, if you, if you get in every, every week or two, like, and you look at the table of contents, it’s not the same writers in there every single time. They kind of rotate in and out because it takes a while to create one of those things. and so hopefully we can have a similar type effect. and it will be a lot easier to justify the paid subscription then than as a standalone. But as a reader, it’s like even better because every week you get something that has been distilled for like a month or longer potentially. rather than whatever I could come up with in like three hours.Nathan: [00:26:04] Because I send my newsletter at the same time every week and three hours is coming up really soon. there’s two sides of that. I wanna dive in on the paid newsletters in just a second, but, on the other side, what systems do you have in place or you’re like you encourage for the writers as part of every, to have in place to sort of start on those ideas early and then be able to refine and develop them over time.Right because that requires somewhat of a research system. It requires some productive procrastination, I guess. Like it’s more than just like working on this article for five months. There’s there’s gotta be more of a process.N Baschez: [00:26:42] Yeah, totally. Oh, this is so interesting. And we’re actually just starting to develop some of this and I’m so excited to like, see just what happens over the next year as we really like start to systematize it. So, basically, what we realized is we were thinking about it, like how we imagined, You know, a magazine or a newspaper might handle this kind of thing, which is like, you have a pitch meeting and like, you come up with an idea for what you want to write and you roughly know like kind of vaguely, this is the headline.This is what the story is about. It may not be the exact wording of the headline, but like you basically, you know what the piece is going to be. And, you come and you’re like pitch it to people and people say, if it sounds interesting to them or not, basically, and then you move on and we, and we S we did that a little bit, and it was just like, this sucks.Like, this is not. This is not it. so first of all, whether something is fully formed or interesting, or not as like sort of a spectrum or like a binary of like, just how interested am I? It’s like, that’s not even the point. Like the point is, I, and like just the sort of adversarial ish relationship between like a pitch.It’s like, I’m, I’m selling you something and you’re deciding whether or not you want to buy it. You know what I mean? Like, Really, what we want is what comes prior to that, because I think there is a time and a place for pitching stories, but it’s after you’ve done a lot of the work to figure out what the story really is.And so how do you, what is that work like and how do you, how can it be made more efficient or better? by the sort of like. You know, by, by the fact that you can do it with other people. So we, I don’t know if we’re actually going to call it this, but my, my goal is for us to call it inkling cultivation, where you have an inkling about something.That’s interesting. And I think another thing that we’ll probably actually call it is what’s interesting. It’s just a meeting called what’s interesting. And you show up and the goal is like to get into interesting conversations, basically. Like if they’re, if people are enjoying talking through an idea, then like it’s working, it’s, it’s all about that feeling of actual, like enjoyment, you know, But the by-product of it is, I can say like, Hey, you know, I was thinking about like clubhouse and I think that I’m not sure if it’s like a feature or a business, like clearly there’s something compelling about the audio room format, but like, is that just going to be a thing that exists in a lot of products, like Snapchat stories or is that going to be like its own network effect, business type, type thing.That’s like going to be, you know, an important company with like some real defensibility and revenue and all that stuff. Like, I dunno. I just, you know, it’s interesting question to me and I’m like, Then other people will tell you what they think, and you can get into a conversation about it and it’s fun and you can take notes and stuff.And then, then you’re in a much better position to like write a draft or do some more research or whatever. Then if I had just kept that thought to myself, you know, yeah,Nathan: [00:29:15] When I can see, someone saying like, Oh, well, that’s. That reminds me of this article. Right. And that someone else wrote and they share with you and you might be like, Oh, okay. It’s been written already. I’m done. But most likely you’d be like, no, actually I disagree here. I like, yes, it has a similar title, but I think it’s going to go this direction.And so, you know, that’s the sort of thing that your very first commenter is going to be like, ah, this has been written before. And so if you have them read that article, because someone in the, in this what’s interesting meeting, Uh, brought it up then you can like, it’s a better research, more thought out piece,N Baschez: [00:29:53] Totally. I think that, I think the core idea is like at the end of the day, writing is an act of communication. And so it’s, it’s, it’s a good form of communication when you. Have thought deeply about what you want to say and you’ve really crafted it. But in order to get to that point, you want to start with the more informal, casual, everyday way of talking.And I think the feeling that this is a fascinating conversation is the key thing we want to get to because that is ultimately, it’s like, that’s the spark that you’re trying to like recreate for readers down the road. It’s like the thing that feels interesting now, Is ultimately the same feeling in some ways that the reader is going to have later, you’re just serving it up to them on a platter in like a guided journey, as opposed to like the sort of like rough, you know, loose thing that happens in like life live conversations.Nathan: [00:30:38] What I love about that is not just the refinement of the ideas, but you’re also taking writing, which can be a very solo. Sometimes lonely task and turning it into a, a, a social engaging, you know, having that connection. And it’s something that, right. Someone might start a newsletter it’s growing and they get advice like, Oh, you should hire an editor, they’ll push your ideas.But then you’re like, look, I don’t want to spend hundreds of dollars per article on an editor yet. I’m not quite there yet, but you could make your own like, I’ve recommended mastermind groups a lot,N Baschez: [00:31:12] Yeah,Nathan: [00:31:12] And so you can make your own like, What’s interesting group of like get together with four or five newsletter creators in the same space and have a weekly or a monthly call where you just kind of riff on each other’s ideas, on, so it’s amazing that you’re creating that for, you know, members like, publications inside of every.N Baschez: [00:31:32] Yeah, totally. I’m so curious, like mastermind, I didn’t even make that connection, but I think it’s completely apt. Like, are there any structures from masterminds that you think would be useful for, you know, groups of writers talking about what stuff they’re interested in, potentially writing about.Nathan: [00:31:47] Well, there’s two sides of it. One with the mastermind. It’s using that word. It’s more commonly going to go to, to like, how should I grow my publication? What strategies should I use? And so a lot of people are going to fall into that side of like, Oh, well, Nathan, if you did this, then you would grow 5% faster per month.And that has its place. and can be like highly recommended, very useful. I think what we’re both saying is you need both. Yeah, like that’s the business side. And then for a second, let’s just set aside everything about business and growth and let’s just talk content and make sure that those stay like there’s a wall between those.Yes, exactly. that would be funny if you’re like this. This is Church N Baschez: [00:32:37] Church. Yeah. Oh my God. We should totally call it church. That is actually a great idea. And then we can have another meeting called state and it’sNathan: [00:32:46] Yeah. It’s just about the business logistics of everything else. What’s the conversion rate on that in, and you’re like, I don’t care. This is a church meeting.N Baschez: [00:32:55] Oh, my God. I actually kind of love that idea. I mean, there is a problem with media companies where there’s sometimes too much separation between church and state, but I think having a cheeky plan that could be like a really fun, I’m going to pitch Dan on this. Okay.Nathan: [00:33:06] I love it. So structured for the mastermind. You know, I’ve, I’ve seen, hot seats. You know that that’s probably the most common one where say, if you have four people in a mastermind group, they’re, they’re rotating, who’s in the hot seat every week. Another important thing would be accountability. often you have these ideas that maybe you’ve you’ve pitched it or thrown it out in a what’s interesting meeting.N Baschez: [00:33:32] Right. And then you follow up and you’re like, so whatever happened, did you write that thing?Nathan: [00:33:37] Right. And so there’s some visibility, let’s say there’s like five or six of us on the, on this meeting. If there’s some visibility into what’s in your rough drafts article list. And you’re like, Hey, that one is actually good. Like I have one from quite a while ago. It’s like, Oh man, it’s probably 70% written.Or at least the first draft of it is, and it sat there and I haven’t worked on it in six months. And so to have that accountability where someone is like, Hey, You got to actually put work into it. Like you went from productive procrastination and now you’re just straight up procrastinate.N Baschez: [00:34:11] Avoidance. Yeah, totally. Or anything. If you want to join the collective, there’s always a seat for you at the, yeah.Nathan: [00:34:18] I might just have to be.N Baschez: [00:34:20] Interesting meeting or should we call it church?Nathan: [00:34:22] Yes, exactly. I like that I’m being recruited to church. I did not expect that on, I don’t know.Well, I love that approach of getting more support beyond like the editorial. Are there other areas that you think of, you know, individual, newsletter creators should be looking to, to add some more support?N Baschez: [00:34:47] Yeah, I think, I, I mean, there’s a, there’s obviously a whole bunch of, kind of like just the logistics of running a subscription business. That it’s really nice to not have to, you know, like someone wants to cancel and, you know, they just emailed, you cancel me instead of clicking a couple buttons or whatever, like doing customer support, email is like, you know, always, never, never fun.And when we were on sub stack, they did that for us, as they do for all of their writers. but you know, like we do that now. but I actually liked that. Like, I think it’s really good for us not to be insulated from those types of things and to have the control, to make it a better experience or whatever.If we want, like in whatever way is like best, best kind of like suited to our, to our strategy and to our customers and all that stuff. but like as a writer, you know, you don’t necessarily want to be doing, doing a ton of that. what else? I actually think it really helps to have someone to help you look at your data.Cause understanding kind of like benchmarks and the gotchas and like, it’s really like. Being able to confidently draw insights from data is requires a decent amount of, of, experience. Just like understanding how the technical systems work that create your data. So whether, you know, it’s, even if you, even if you’re on sub stack and you’ve got like sub stack has certain data, but it’s kind of a black box or whatever to you, you know, you still have your Stripe account.And there’s a lot of different tools that can help you visualize your Stripe account and like every sub stack. You know, paid subscription, writers should be looking at their cohorts and you can do that in subs or in Stripe and in other services that you can connect to Stripe, but like it doesn’t show you what and sub stack.And it’s like really important to look and see if your cohort performance is improving over time. Nathan: [00:36:27] At a high level. Can you share what you’re looking at in cohorts? Cause I think, you know, coming from SAS, both you and I spent tons of time diving into cohort performance, ensuring and all of that.N Baschez: [00:36:37] Totally.Nathan: [00:36:37] I think a lot of other people won’t have that same context.N Baschez: [00:36:39] Yeah, definitely. I mean, at the highest level, basically, if you’re running a subscription business, you can really only grow so fast or you can only go so far if you have high turn. Cause even if you’re signing up a bunch of new customers all the time, if just as many customers are canceling, then you’re not gonna end up with a business that has a lot of longevity.Whereas if you have a very small percent of your people leave, then you don’t need to add as many norms. As many new customers in order to grow. And even maybe if you haven’t quite figured out your marketing or whatever, it can still be a pretty quickly growing business. just by the sheer fact that everyone’s sticking around.So like churn, churn is incredibly important. and a lot of ways more important than, how, how well you can attract new subscribers. because it shows if there’s really like. Longevity there and like real value being created. and you know, the best way to measure that is just by looking at how long people stick around on average.But it’s interesting because it’s more useful to look at this in some sort of segmented way than just in general. Like if you’re looking and you’re like, okay, Whatever, like 2000 people have ever signed up and I have 1,600 that are active now. So I’ve got like, whatever percent turn that, that would turn out to like, that is one way of doing it.And it is, it is like a somewhat useful metric. But if you want to get pretty actionable and figure out like, okay, Why are people churning or like, can I co can I connect any of this churn to like trends or whatever? It’s nice to, it’s nice to segment it in some way or another. And the most common way to do that is just based on cohorts, where it’s like the cohort of people who signed up in may, what percent of them were still there in June?What percent of them are still there in July? What percent of them were still there? And you can kind of like draw these lines almost that it’s like the X axis is months since joining. And the Y axis is percent that are still around. And so it starts in the top left at 100%, zero months since joining.Okay. A hundred percent of those there. And then in month one, what percent and what to what percent and what three, what percent, and you want it to basically flatten out at some point, if it just keeps going and it’s approaching zero, then like, You know, overall the business’s revenue will eventually approach zero.And, and, but, you know, good is it’s hard to benchmark. It’s like, that’s always, the hard question is like, what is good? Well, it’s like good, bad, whatever is less important than just doing the math and extrapolating what your business is likely to do. You can make projections based on these kinds of like averages.But you know, it’s probably, you want to have greater than like 50%, terminal cohort retention, especially after like a year of being around. And, if you don’t, it’s important to kind of like really figure out, like it’s probably important to refocus efforts and say like, Oh, we’re not going to focus so much on new customer acquisition.We’re going to focus on really understanding what’s going on with our existing customers and why, they, they seem to be leaving so frequently. so anyway, that was kind of like a long-winded answer, but it’s, it’s really, really important for any subscription business. consumer, you know, media subscriptions is really no different in principle than like.SAS B2B software and a lot of ways, once you get to the really core principles, of course, They’ll have different, you know, once you start to get into more of the nuances, there’s very different levers. There’s different specific numbers you may want to look at, but like at the core, looking at your retention on a cohorted basis is like really, really nice.And also you want to see it go like up over time, ideally. So it’s like maybe you had some cohorts that churned a lot early on, and then, but as you’re making improvements to your, to your product, whether that’s an editorial product or any other type of product, you hope that new cohorts tend to stick around better.Cause that sort of shows that you’re actually creating. Value like the things you’re doing to improve your customer’s experience are, are actually creating value. so anyway, it’s been interesting to us to observe what kinds of things make a difference in what don’t, it’s, it’s, it’s its own whole big thing to dive down, but yeah,Nathan: [00:40:26] One thing that I’ve often seen in intern cohorts is the very first cohorts, tend to do decently well, the next there’s like this Valley, the next hole don’t do so well. And you climb out of it. And basically what happens is you get the people who love you and would buy anything and pay for it forever.And they signed up the moment you launched. They’re just like. And they’ll never cancel. And then after that, you’re into the people who are like, okay, I’m signing up. Cause you say it’s good. You know, I’m, I’ve been marketed to when I converted, but then your product isn’t that good, you know, as in they cancel and then the product gets better over time.And as more people sign up, then they’re like, Oh, this is actually what I expected to get. And, they’re sticking around because of the product, not just because of an existing relationship or they’re a true fan and that’s what you want to see. Like, so don’t be. You were sad when it goes down immediately, because when you goN Baschez: [00:41:19] Yeah,Nathan: [00:41:20] Fans to just, you know, subscribers, but you do want it to climb over time.N Baschez: [00:41:24] And, it’s so interesting, like learning what causes it to go. Like you’ll try different things and there’ll be some things that. You think will make a huge difference in it? Like maybe honestly can’t tell if there’s any effect in the data. Like maybe the turn got a little bit better, but you’re not sure what exactly caused it.And then there’s other things where there’s like, it’s a pretty clear difference. And for us, what that thing has been, you know, without giving away too much of the secret sauce is, when someone new joins the bundle that people already like, it’s like, that’s the feeling of the value proposition of the bundle is like, Oh, My price didn’t go up, but I’m getting more value now.And it causes the expectation of like, this is going to keep happening. So I might as well stick around and kind of like, see what’s going on here. You know, even when we have like a hit article, it’s kind of like, not as powerful as someone new joining the bundle.Nathan: [00:42:14] Oh, interesting. Okay. I was also going to ask how pricing plays into it because I noticed that on the new site you’re pushing, you know, the annual plan is the default. So $200 a year for every, $20 a month is available. You know, but it’s sort of like, Oh, okay. Yeah, yeah. In the FAQ, if you want the monthly, here it is.N Baschez: [00:42:33] Yeah, I couldn’t decide if that was like bad or not like to do it that way. I really don’t want to design anything. That’s like user hostile. but I really didn’t want to prioritize the monthly thing very much in the design. And it’s hard to like, what’s the difference between like having a dark pattern and just having something that’s like deprioritized prioritized in the design.I don’t know. Yeah.Nathan: [00:42:55] Well, I think, I mean, you’re S you’re saying this is the product that we’re selling, that doesn’t work for you. We do have other options, and I feel like that’s different than like, I don’t know, dark patterns and user experiences, a whole different road, and all you’ve done. Is like on the site, your, your user interfaces is just copy.N Baschez: [00:43:15] So the question was basically like why the $200, why focus on annual, all that kind of stuff.Nathan: [00:43:20] Yeah. And what effect has that had on churn?N Baschez: [00:43:23] That’s an interesting one. So we have very few people that have been around for over a year. So our initial customers from when we very first launched, paid subscriptions, are a lot of like, sort of true fans that signed up, like on day one ish. And so those have retained fantastically, well, we’re a little bit more curious about what’s going to happen.Like come, I think June-ish is when we start to really get beyond just like people that knew us, you know, and like, yeah. We’re kind of hitting a stride with some of our writing and we added, Tiago to the bundle and all that kind of stuff. That’s when we start to get beyond a little bit. And, when those yearly renewals come up, it’ll be more of a true test.A lot of the reason why we decided to focus on annual instead of monthly is because if we can convince you to be around for a year, that gives us a lot longer to improve. Whereas if it’s a decision every month, like we’re only going to get so much better in a month, but in a year, we’ll have a lot. I mean, I hope we’re going to feel like very different in a year, you know?And, so it just lengthens the decision time. And like in exchange, we give you $40 off because you would be spending $40 more if you stuck around for a year on a monthly plan. and also in exchange, we give you if it’s only $1 for 30 days and then we charge you for this. So there’s a pretty long, it’s not a free trial cause we want to make sure, like, you know, you’re a little bit bought in and kind of like there’s some skin in the game to like, Give this a real try and like read some stuff, because I do think that there is some activation energy around like reading things.Like it takes some effort in order to get the benefit out of it. But once you do that effort, you may be bought in, or maybe you’re not. And in which case we need to do a better job, or maybe you weren’t like the right target, kind of like the right kind of person we were targeting. But, Anyway, that was the kind of theory behind the $1 for 30 days.Thing is like, you should have a pretty good idea of if this is like, basically good enough for you to like stick around for a year. And then once the year happens, like then we have a year to get better, to Nathan: [00:45:12] Right.N Baschez: [00:45:12] Prove, improve the productNathan: [00:45:13] Yeah. That makes sense. Is there anything else that you’ve learned on running the paid subscription that, you know, people would want to know if they’re either thinking about moving to paid or they’re, you know, they have the free and a paid and they’re thinking about, okay, how do I drive more value or increase revenue?N Baschez: [00:45:30] Yeah. I mean, I think if you’re thinking about going paid, the key thing is if you’re not already paid, is that because it’s sort of like a part-time thing for you and there’s something else you’re doing for your primary income. And, if so, like how much it focuses you really going to be able to dedicate to the paid thing?Because it is like really hard. It’s some people do have them as side projects, like paid newsletters, but. I personally feel like there’s this kind of bifurcation that happens and that most people in this sort of like buzz about paid, paid, paid, paid newsletters right now, like aren’t focused enough on which is like, these things tend to either work and then work really well.Or people try am for a little while, and then it’s not right. It’s not right for them at that moment or whatever. And so, Most people who it’s not right for are the ones who had a newsletter that was free. And they have some sort of other job that’s like takes up pretty much their full time. And then they want to just tack on a little bit to what they’re already doing.And then they, they struggle with it. because it is hard to sustain a solo subscription where it’s like, you definitely will have those people that are just like your super fans that are going to buy anything you do, because they love you. and if that’s so many people that. You know, you don’t even have to almost write that much and people will still stick around and that’ll support you then.That’s great. That’s awesome. There are definitely people who are in a position to do that. Like, you know, when slate, star codex moved on to sub stack and like, it was the first time he’d ever offered, paid subscriptions for his writing. I’m like, I don’t care. Like, just as a thank you for like all the years of like, Whatever, like hard work that love his work that I loved.I’m just like, I’m paying, I just want like to be on the list. It’s like, so, you know, and so, so for him, it doesn’t even really matter what he’s putting behind the paywall, because he has such a big audience of people who like, love it so much. whereas like, you know, for me, I have to prove a lot more value.And I haven’t, I haven’t built that thing up yet with very many people, maybe like a couple dozen, but not, you know what I mean? Like people with, you know, whatever in my family or something. so, you know, I think that’s a real thing for people that are like considering going paid. there was another part to your question though.I forgot what it was. Cause I rambled for a long time.Nathan: [00:47:52] I think just noticing what your other commitments are in life, that’s really important. Right. Cause if you’re like, yeah, I’ve got the newsletter. I do that on the side, then I’ve got the full-time job and then like, Oh yeah, I just had a kid or I just got married, you know, or some other things.And it’s like, yeah, let’s also do a paid newsletter. And it’s like, no, no, no, no. Versus if you’re like, you’re like, okay, I’m at the New York times as a journalist, I’m going to, I’ve been building up my free newsletter on the side and I’m going to leave this and now do a paid newsletter as my job. and not only do you have the professional experience of like, yeah, I write on deadline every single day, you know?And I have that habit, but also I’m going to be able to dedicate, you know, 10, 20, 30 hours a week just to this paid newsletter. That’s very different from just like, there’s a quick opportunity to say I’m going to stack one more thing onto my list of side hustles.N Baschez: [00:48:45] Yeah. And I think that is, it kind of speaks to what I was getting at earlier with like the inculturation thing of like, you know, if you like have been a full-time journalist and you have a beat and you have sources and you know what it’s like to publish like a couple of things a week, on a regular basis, like, yeah, you’re a really well, and you have the audience or whatever, like you’re in a great position to like, do your own Substack and like.You know, more power to you. That’s amazing. We’re big fans of Substack We’re glad that that, or just in general, the idea of having a solo subscription newsletter, right? Like that’s, that’s awesome. that’s not going to be right for everybody. Like, you know, maybe, and that’s not to say that, you know, like, I think if you wanted to write something that just like, you want to write one thing a month, you know, like some people maybe that would work as like a solo subscription, but like in a lot of cases, I think that may end up being tougher.So I don’t know. I think, I mean, in terms of really tactical advice, I really do think frequency matters a lot and it really, if you can get up to like three, four times maybe even like daily or like weekday weekday-ly Like those do tend to do better. I, I don’t remember a lot of the specifics of like when I was at Substack and I had access to the numbers and stuff, but like there was, we did look at that and there was a real correlation.Nathan: [00:49:58] Yeah, that makes sense. let’s talk platforms for a little bit, cause we’re seeing obviously sub stack has grown. Like crazy. we can get into the broader macro things of review and Facebook and Twitter and everything else. but for just a minute, I’d love to talk about obviously the growth that people are seeing on sub stack.And then there’s this category of newsletters, especially over the last, probably three months in particular, every being one of them that have made the switch off of sub stack either to. MailChimp plus Pico or convert kit or a custom built platform. and I’m curious what you’re seeing and, and you know, what drove you to make the switch to a custom built platform?N Baschez: [00:50:39] Yeah, I think, I mean, subsets and amazing place to get started. I was their first employee there and like a huge fan. I’m biased. I’m a shareholder still like, you know, like that’s. You know, we should put that on the record. like, so I think that, I think that they’re very focused on, on a very specific thing, which is like the solo writer, you know, and I think to some extent they’re very interested in, groups of writers working together.And to some extent they have a thing, but it’s more like individual publications with multiple by-lines rather than like a bundle of publications really, you know? and so, It’s all, it’s all built around that very specific thing. And I think they’ve done the reason why, you know, we’ve heard so much about sub stack, but like, you know, other platforms that, I mean, like review was around, I think before sub stack remember full, like the reason why sub stack took off is because I think a, of the simplicity of what they created, there’s just.Zero setup costs. I think B because it’s a little bit more constrained and it’s a little bit more branded, substan just felt a little bit more visible than something like remember fall, which is like totally behind the scenes. review had a little bit of that same branded feeling. but I think, you know, maybe not quite as much as sub stack, but then see, and I think really the most important thing is they.Had a new vision for what writers, what solo writers could do. They were like going out to people who are talented writers that had big audiences and saying, Hey, I know you right now, you’re focused on. Getting a book deal or getting a job at wherever the next step is for you and your career path. But like, have you considered doing a paid subscription thing?There are some people that are doing it that started from a place that didn’t even have as big of audience as you. And it worked really well. And they got a lot of writers to like change their career plans, basically to try a new model. And that’s what I mean when I was at sub SAC, like we would call it jokingly like the religion, you know?And it’s like, we didn’t like. You know, it’s like faith that you can make your own business. You can be your own publisher. You can, you can, it’s better to have an ARR than a salary. You know, it’s better to have an audience whose email addresses, you know, they’re looking forward to hearing from you in their inbox and you own the list of their email addresses or whatever.It’s better to have that than to have that to be published. And it’s really appealing religion. You know what I mean? it’s, it’s something that I think, I think that they just aggressive. They are, I understand writers cause Hamish is one and you know, was a journalist for a lot of years. And but he also has that kind of like sales person, you know, of like, he, he, he knows that’s like their DNA is like, have you considered this?Basically? I know you probably haven’t, but you really may, will actually want to. and then I think also what really. Supercharged. It was just honestly, Andreessen Horowitz, like does a great job at like they’re very well networked and they use their network and we’re seeing it now with clubhouse too.And that really can there’s there’s sort of network effects that they understand around cultural stuff. That’s like, You know, it’s acceptable to like have a sub stack in a way that going on a platform that maybe people haven’t heard of as much as like, might feel more risky to people who like, you know, are, are more, like if you’re, you know, a journalist or whatever, that, that you, you want to do something that feels like it’s a little bit more well understood or whatever, subset gets kind of like blazed that trail. So I think there’s a lot of huge advantages to being on sub stack. I think that it’s awesome. That sub stack is sort of like realizing that vision in a way that, you know, we talked about when I was there, but like, There wasn’t a ton of people publishing on sub stack. When I was, you know, it was really amazing to see kind of like the growth over time.And, I think that there’s definitely at the kind of like, high-end some, some possibility that there’ll be more, people who kind of have a vision more to create their own publication. That’s like multiple authors, like maybe it’s structured as a writer, collective like us. Maybe not. but, I think that some of those, it will make sense for them to like own their own stack and, and, and leave the platform to have a little bit more control.But maybe some cycle also build to be like more supportive of that use case. Like I could imagine them if they had given us like, You know, a lot more customization. Like they could’ve kept us for a little longer probably, and it doesn’t seem like something that doesn’t fit with their business model.I mean, at the end of the day, if they’re providing, you know, the infrastructure and they’ve got their percent take, and if you want to go in and do other customization, you can, but like you don’t have to, you know, there’s, it could, it could have. Stuck around a little longer potentially. so I don’t know.It’ll be very interesting to see kind of like what happens at the high, I think at the high end, it kind of will bifurcate what, where, some will kind of form their own media companies that are like multi, multi author type deals, whether it’s a bundle thing or like a, just a normal publication type thing.But then I think there was also going to be a lot of people who want to just write, you know, and like they know what they’re right. They know their audience, they’ve got their thing figured out. And now they’re kind of cashing in on it rather than it’s a different situation from like, you know, like Matt Yglesias, for example, like when Matt Yglesias, like, you know, 15 years ago or whatever was coming up, it was probably very important that he had like colleagues and editors and all this stuff now, like he’s been doing it for awhile.He can, like, he knows what he’s doing and. You know, a little bit of different needs. So it’s an interesting, like thing to observe kind of the market evolve a little bit, and our understanding of like, how to make these models work evolves.Nathan: [00:56:09] Yeah, I think it will be a lot based on, like, you’re saying what the individual writer wants, you know, and some people are saying like that super clean, simple publishing experience and just like. Almost put up some of the guard rails. So I can just focus rather than getting caught up in the weeds of everything.And then other people are going to say like, okay, well, based on pricing, you know, I want, I want to be paying three, 4%, not 10%, you know, or, or you’ll get into automations or some of these things where people want to try a hybrid business model. I think it was interesting. Hunter Walk has his article on like the multi-SKU creator.And so having method where some of that’s available, you know, cause stack, you are limited to just like recurring payments and you’d have to use a teachable or convert kit or Gumroad or somebody else, if you wanted to do a one-off product.N Baschez: [00:57:04] Yeah, the multi SKU creator thing is really fascinating to me. I don’t, I don’t know how I feel about it on the one hand. I’m like, yeah, that makes sense. Cause you’ll probably, maybe you’ll have like something that’s cheap and then something that’s more expensive or whatever, and different people want to buy different stuff.On the other hand, like I’m not anxious for us to develop more skews. Like I want to pack more value behind the same skew. It’s like we have this bundle and we just want to keep making it better and better. And we think eventually the Tam could be pretty large. Like there’s a lot of people who, you know, whatever may eventually want this, but it just, it needs to be really, really good.And let’s just keep making it really good and making it a no-brainer where there’s like tons of value behind the paywall, but that’s just one simple price. There’s one simple product, you know, Nathan: [00:57:46] Simplicity is good. last thing that I wanted to touch on is, you know, in the last two weeks, I don’t know. It’s pretty recent since we’ve been recording, you know, Twitter acquired review, and also Facebook there’s like some, not an official announcement. There’s like some, apparently they’re getting into newsletters too.So I just love your take on it. I’ve at, you know, a couple of years ago, newsletters where this thing that people are like, you’re starting a newsletter.N Baschez: [00:58:13] Yeah, totally.Nathan: [00:58:14] And then now all the big companies are getting into it.N Baschez: [00:58:18] Well, it’s interesting because, You know, Twitter historically has fumbled, like new opportunities, basically like vine and like Periscope, like, you know, there’s a lot of sort of stuff that they were like right there. And then like someone else really ran with the opportunity. Like vine really could have been TechTalk, you know, like.And Twitter could have owned it. like, I don’t know, maybe not, but I think, I think it could have been. and, like, you know, the newsletter thing is interesting because, it seems like they’re acting a little bit more decisively about trying to convert people from being, you know, a writer with a Twitter account and then all their writing somewhere else to like, what if I just did it all here because my audience is here and the audience I’m trying to reach is also here.And so, yeah. We can really reduce the steps in the funnel and that could be really good thing. So, I think for Twitter, like if they want to be really bold, like they could, it could be a massive opportunity. It just historically, a company as big as Twitter is not going to be, I think very decisive in, leveraging the value that they can add as Twitter.Because it, it creates a lot of risk for them of like upsetting the other parts of their business model. And there are very real trade-offs like, do we want users to keep scrolling and seeing more ads? Or do we want them to like go into some subscription funnel where it doesn’t make as much sense to display ads?And like, you know, there’s very real trade-offs there and how do we even split the money with writers anyway? And like, what do we, you know, there’s how do we power discovery when. Like basically the reason why people are mad at Twitter and Facebook and YouTube and other platforms is because they did a great job with discovery.And some of the things that they were helping people discover were like terrible. And so at scale, you can’t like if you’re trying to get in the middle of content discovery, you’re also going to take all the risks that come with that. And it seems like we’re in a moment where generally speaking, the last thing they want to do is be more in the middle of that.So, it’s tricky. It’s it’s, it’s very tricky, but, they certainly have a lot of potential. It’s just unusual, I think, for a company with that kind of potential to actually, use it. Well, one other interesting comp for this is like YouTube has a Patriot and competitor. It’s just not as popular as Patrion because you know, they don’t push it because it conflicts with their main actual business.Nathan: [01:00:32] Oh, that’s interesting. Yeah, because I remember them making quite a bit of news when they announced it and it’s sort of like, okay, is this for Patrion? And, you know, patrons just likeN Baschez: [01:00:43] Yeah,Nathan: [01:00:45] Keeps climbing. SoN Baschez: [01:00:48] And then with Facebook, I mean, Culturally, as far as companies go, Facebook is much more prone to like actually copy a thing, you know, like boldly, you know, whereas I think Twitter’s a little bit more in line with other companies, at least what we’ve seen historically, where they’re a little bit more cautious about it.But I mean, Facebook, like the absolute worst audience for Facebook in terms of any sort of level of trust is just as writers, you know? So like I’m sure Facebook is so huge that there’s like, you know, definitely gonna, they can find some writers that like will publish on Facebook, but like, In terms of like, at least in the United States, you know, sort of like journalism and typewriters.Like, I don’t think anyone would want to publish on Facebook. Even if Facebook offered them a large sum of money. I think culturally, it would be like too, there would be like, you know, Fox news publishing your thing. If you’re like a Democrat or whatever, like you just can’t, it’s like, you know, and you know, whether that’s fair or whether they’re right or whatever, it’s like a totally separate question from just what the reality is.I think my read on it. Yeah.Nathan: [01:01:48] Yeah, that totally makes sense. Well, I mean, no matter what, well, what it’s lending a, an air of legitimacy and, you know, it’ll bring so many new writers into the, into the fold, right. Because if someone’s like, I’ve been growing my Twitter, following else. And then this button pops up of like newsletters new and you’re like, here’s the letter I thought about starting a newsletter.Sure. I’ll do that. And then, then really the buying decision happens. Someone might start on, on Twitter and with review, but then they might also just easily switch and say like, okay, you know what, sub stack or convert kit or ghost or one of these others, you know, basically it might serve as a funnel to bring someone into newsletters.Is more likely to end up on review than anywhere else because that’s the natural path. you know, there’s a decent chance that as they grow, they start to look at other platforms.N Baschez: [01:02:40] Yeah, that is an interesting, I wonder it would be very interesting to look at the effect of that thing on YouTube and like, see if it’s like driven more people towards the Patrion model almost then it has like captured the people that are trying to do that. Or it’s like how many people uploaded a video to YouTube, and then you saw that you could like do sponsorships on it and thought about it and maybe Googled it and then like, Found out about patron because of that or something like, you know, interesting, interesting to, to think about the downstream effects of that.Yeah. I mean, it’s so go ahead. I was just going to say, it’s so interesting. The effects of like, just something becoming a meme, you know, like this is kind of what I was saying about sub stack religion earlier. It’s like, I think a lot of times people do what they believe will be profitable to do, and that belief is based on what other people seem to be believing right now.And so, it does add a lot of momentum to that belief that Twitter and Facebook have added support for it or are considering it or whatever. I think that, It’s interesting. It’s interesting that it’s the word newsletter that has sort of captured all this magic. Cause it’s really, to me, it’s about writing and it’s about the direct relationship with readers and writers and it’s about, like I think email is a channel is a good component of it. but there’s also this other. Almost baggage with the word newsletter that it’s like almost the form of it. It’s like, Oh, this is a newsletter. So it means like welcome to edition number, whatever of my Roundup, where I like it’s a little, some links with my commentary or whatever. Like, you know, like that’s not necessarily like what a newsletter really is, but that’s kind of like what it was.So it’s interesting. It’s like a blog is where the writing is. And then the newsletter is likeNathan: [01:04:26] But blog doesn’t have the same, trendiness, like it, you know, like, Hey, you should quit your job at the New York times and start a blog. They’d be like at right now. They’d be like,N Baschez: [01:04:36] Yeah.Nathan: [01:04:38] Where are these? You know, like, I don’t know what the deal is with that.N Baschez: [01:04:42] Yeah. It’s so funny. Cause it’s like the word blog is like totally out, but like as recently as I dunno, whenever medium first launched, it was like a way to start a blog without having to like publish all the time. Cause you’re like publishing on medium rather than having to start a blog, you know?Nathan: [01:04:56] Oh, that’s fascinating. Well, I should let you go. I’m also realizing it’s I should have turned some lights on. It’s getting weirdly dark in here over time.N Baschez: [01:05:06] On our conversation.Nathan: [01:05:07] Yes. There’s the time has come to come to a close. but thanks for coming on. Where should people go to learn more about Every?N Baschez: [01:05:15] Yeah. Every.to. T O every night to we like to pretend that it’s like Toronto or something, it means something cool. Literally it’s just Every dot. And then that was like one of the, what are we going to do? every.limo or something like now, like that doesn’t, you know,Nathan: [01:05:31] Taken.N Baschez: [01:05:32] Is worth a couple of billion dollars and their notion dot. So, so like every dot TO will probably be fine.Nathan: [01:05:37] Yeah, so long as it’s not a negative, you, you can go with, but these things, awesome coming on and, hope everyone will check out every and, and we’ll talk soon.N Baschez: [01:05:48] Thank you so much for having me. It’s a lot of fun.

Khe Hy’s been called the “Oprah for Millennials” by CNN, and his writing is all about transforming your relationship with time, work, money, and, ultimately, yourself. Today we talk about how he runs RadReads, his newsletter for over 25,000 people. It’s an incredible newsletter where Khe gets super tactical about Notion, but also goes deep on living a better life, organization, productivity, etc.The biggest highlight from this interview? Khe tells us about going from $100/hr work to $10,000/hr work. He’s not joking! Khe’s building a whole course—Supercharge your Productivity—on this very topic.Khe also shares useful insights for every newsletter author and online businessperson, including:• Finding the best marketing platform for your business. • How to get your content in front of someone else’s audience. • How to launch a premium product.And so much more!Links & Resources Notion – The all-in-one workspace for your notes, tasks, wikis, and databases. Loom: Video Messaging for Work Friday Forward Inspiration & Motivational E-mail - Robert Glazer Patrick O’Shaughnessy Invest Like the Best podcast Khe Hy’s Links Newsletter: RadReads Twitter: @khemaridh Episode TranscriptKhe: [00:00:00] I often push people to ask, what’s this for? Right. So like, you want to switch from MailChimp to ConvertKit, like, what’s this for? Like, do you want to open it? Sorry, YouTube account. What’s this for? So don’t be satisfied with the first answer. Go one level deeper. Go to the second answer, go to the third answer.And actually ironically like copywriting, you’ll probably land on some deeper human need that you have.Nathan: [00:00:29] In this episode, I talked to Khe Hy about how he runs RadReads, his newsletter for over 25,000 people. It’s an incredible newsletter. I love everything that he features, where he’s talking about Notion, living a better life, organization, productivity, all this other stuff. And he takes it into some pretty deep conversations, which I love.Alright, few highlights that we dive into: One: $10,000 an hour work. Yep. He’s not joking. He actually means that; we dive into what exactly that looks like, what it means. We get into product launches. He shares the numbers from the launch that he’s in the middle of right as we record the episode. there’s a lot of great stuff.So I’m going to get out of the way and just let you dive in and listen to the episode with Khe.Khe, welcome to the show.Khe: [00:01:11] Nathan. Great to be here. Thank you for having me.Nathan: [00:01:14] So we were just joking before we, we talked, you and I have exchanged tons of emails, Twitter DMs, you know, Twitter mentions all of that. We have not actually ever talked until this moment.Khe: [00:01:26] You have just converted from a Twitter avatar to a real Zoom human and in the past five minutes. So it’s great to meet you. And that’s why we love the internet.Nathan: [00:01:37] Yes. Well, it’s fun to, I feel like I know, you know, your work really well and, and, um, now it’s nice to put a full, a full face to it. so I would love to dive in. Maybe if you could tell listeners really quickly about rad reads, give the high level, like why someone might subscribe and then from there, we’ll start to dive in your backstory.Khe: [00:02:00] Awesome. So read, read, I guess I would start by saying I’m the accidental entrepreneur and accidental creator. And I would just show my cards immediately that like I’ve rarely had a plan in this whole internet game thing, and it’s all kind of happened. And so. What is RadReads and what can you expect?If you sign up, when you sign up RadReads is, it’s a newsletter and the blog about that helps people live intentional and Epic lives. And so what does that mean? the informal tagline is come for the productivity. Stay for the existential. And so we will lure you in with a text expanders, financial independence, retire, early notion, and then it would be like, what’s the deep underlying need that that’s really trying to satisfy. And so that is kind of the, the ethos, the vibe it’s playful, it’s inspired by surf culture or hip hop culture. and I write, so I read a ton. And through the writing, quite, quite new, actually almost approaching two years. I’ve, started an, course business related to that, but I’ve dabbled in so many other monetization, harebrained schemes along the way, but mostly now newsletter blog leads to, online courses.Nathan: [00:03:31] Yeah, that makes sense. Well, we’ll dive into newsletter, monetization, and so much other stuff, but you did not set out to be a writer. You didn’t set out to, you know, run your own business or any of that. Let’s take us back. What was, what was your career before you drove it to this crazy internet world that we’re all in.Khe: [00:03:51] It was, as Charles Dickens said it was the best of times that it was the worst of times. So, I here’s a little detail important fact, in the stories, you know, I grew up as a child of first-generation immigrants and it was all about. School work, put your head down. Don’t take risk. And so I got on the first generation, escalator, I went to Yale, I majored in computer science.I worked on Wall Street. I was a really good kid. I like buying sat books and all that stuff. and so I just put my head down and did the work, and never really thought about anything else. Just get on the escalator and stay there. I did that, that brought me to wall street, 14 years on Wall Street.And, I had a really good career and I had, hopefully what’s a third of a life crisis. you know, it’s 30, 35 years old. I was probably a little bit, not exactly a third, but, I was just kind of, I was doing great. I was doing great. I was, yeah, in that, that world, uh, made a made man in the sense that if I just didn’t screw up, I would never have a financial worry for the rest of my life. But I was bored as heck.Nathan: [00:05:06] I was going to say, but then you hadn’t go and screw it up.Khe: [00:05:09] I know, and I did screw it up and boy, did I screw it up? I was bored as heck and I love the internet. You know, I had been making HTML pages on 28.8 modems. I had an anonymous blogs and cause you can’t do that stuff on walls. And so I was like, there’s this whole world out there.And I’m just going to be an expert in this thin, thin sliver. I, I basically studied robot trading. So like actually all this Robinhood stuff is like, Like the end of what’s happening right now is what I studied, like the rails of, of wall street. And so I was a little agitated. I was just like, what’s the point?What’s the point? I had some savings about 18 months of savings, where I could just burn through them and try something new. It took a couple years, but I just quit. I quit without a plan. the only little anchor in this crazy C of uncertainty was a tiny little g-mail based newsletter that I had started.Nathan: [00:06:13] Yeah. So that was RadReads.Khe: [00:06:16] How was RadReads? Yeah.Nathan: [00:06:17] Did you call it when you start calling it RadReads?Khe: [00:06:21] I, I think it was like the third issue, the first issue. And we’ll, we’ll share it on Twitter for posterity when this all comes out. But the first issue was just. A few reads from my recent vacation. So it was classic link blogging through Gmail, BCC 36 recipients. I remember some of the articles that were in it, there was like a Mark Manson, Louis CK interview, that tells you what time period we were in. uh, some Elon Musk’s stuff, but, it was a few interesting reads and I think four or five issues later, I just picked up rad reads. I was a sucker for an alliteration, but mostly I love surf culture, but it was all wall street, people that were reading it. And I just loved watching them cringe when they had to say the word ride, to me.And that was like, really why I wanted the word rad. I do try to live that Ethan, but I was like, I want it to stick it to them. Just a little. that’d be like, you gotta say rad, you know, you can’t say it is what it is. You just got to say rad when you talk to me.Nathan: [00:07:28] Those 36 people. Did they sign up for you for it? Did you sign them up? How did that workKhe: [00:07:35] So I probably did something that would have violated GDPR rules. but they were my friends, they were my friends. and so it was just a Hardy BC, and it was, it wasn’t meant to be a newsletter. It was just a one-off thing link. It was linked blogging. This was almost six years ago where it was still quite rare.It wasn’t not tons of people were doing it. Yeah. That was the phase where everyone had a podcast. Right? Like it wasn’t a phase where everybody had a newsletter. Yeah. You know, play before sub stock. so, so it was linked blogging and those 36 people were my friends and they were like, this is so cool.When’s the next one coming up? And I was like, I don’t know. This is a one-off thing.Nathan: [00:08:21] Yeah. And so, I mean, that’s, that’s interesting. It’s something that Jago and I talked about on when he was on the show, is this like hustle too? It’s not even a hustle. It’s just an ask of like, Hey, I do this thing you want in on it. And in this case, you’re like, You’re preempting that somewhat where you’re going, Oh, here are people that I know are going to enjoy this.And so you already have that relationship, you’re pulling them into it and otherwise when you’re starting posting to a group of like, if you’re posting to Facebook or something, or it’s hard to get the first 30, 50 100 people, but if you’re just texting people then it’s so much easier say, Hey, I do this thing.I think you might like it. You know.Khe: [00:09:02] And I think there were two very, very strong tailwinds that I encourage any creator listening to this, to, to latch onto one is I genuinely wanted to read those articles. So. It was effortless in that regard and two it was, there was a commitment to adding value, adding value through, through curation and through the, you know, micro-commentary And so I was doing the heavy, the heavy lifting for the reader, and it was very hard for them to, to be angry about it. Let alone, if anything, if anything, they wanted more because I was, I was creating value, small amounts. Yeah.Nathan: [00:09:40] Yeah, that makes sense. So where did it grow from there? Right. You’re at 36 people on that lift. Did it stay as a BCC list for anything?Khe: [00:09:49] So it, it stayed at BCC list. I was probably, I was working for about. Eight months. There were, like three more months before I quit. and so again, it was a BCC list. It probably stayed at BCC list until maybe four, four or five months later. and then I moved it to, we won’t say the word, but it arrives with snail simp and, And I bought, I bought the domain and I, you know, created a little, a little Loco and had a hosted blog on medium, but I think it was kind of growing at maybe, I dunno, maybe 30, 30 subscribers a week. Completely organically.Nathan: [00:10:43] You just the people who you had tended out to forwarding it on to.Khe: [00:10:47] Yep. Forwarding. And maybe I would like share the, the MailChimp thing on my Facebook feed, like things like that.But I mean, I, I think the thing that also people should remember is that I had zero followers in any, on any platform. When this started, I had zero Twitter followers I had, and I had LinkedIn connections. Yes.Nathan: [00:11:10] Was, did, did LinkedIn turn into a thing at all for promoting it or not really?Khe: [00:11:15] Probably on the edges, but I don’t think so.Nathan: [00:11:20] Yeah. I have a friend, Bob Glazer who writes a newsletter called Friday forward. And what’s wild is that it’s grown like crazy on LinkedIn and it’s going really well. I think he’s, over 80, 90,000 subscribers and probably a third to half of it is from LinkedIn, which,Khe: [00:11:37] That’s great.Nathan: [00:11:38] Much in that business niche.She’s writing about leadership and all that, but I think it’s just. Interesting. We come across newsletter creators who have grown an audience in so many different ways. And some would be like, no, this is the way you have to do it. And you get someone else who’s like, I didn’t even know that was a thing.You know, I, I did it on LinkedIn. I did it on this totally different thing. And so it shows there’s so many options.Khe: [00:12:00] Well, we can talk, I there’s so many angles to talk about growth strategy because, I don’t really have one, but it’s what I have. I have some insights there. So plant that flag for whenever you think is the right time to talk about it.Nathan: [00:12:15] Okay. So at this point, it’s, it’s on MailChimp. it’s growing a couple of hundred subscribers, new subscribers a month getting into that territory when you’re still like on sabbatical,Khe: [00:12:29] So I’ve so I quit and I’ve been going through those 18 months of cash. I’m actually doing the family version of eat, pray love. So we’re in Bali, we’re in Chiodo or traveling, traveling the world. And really the only thing I have to do is to write this newsletter and it kind of, I think it was also when I think about it, when you leave a high profile job, at least in that world, there’s a huge loss of identity.Cause people immediately want to know like, well, what are you doing? And that, that was the whole point was, I didn’t know what I was doing, but at least this little newsletter kind of gave me this toe hold, like something little that I could point to. And people thought it was nuts. I mean, crazy. that, that was the thing, that I was doing.But at least in my mind, it’s like, well, I got this little thing. And then the point was not. To make the newsletter into the business. It was kind of, a waystation in the process of figuring out what I was going to do. It just was something that I found I was so moved. I just loved it so much that it was it just kind of.Would come out of me that, that, that in hindsight, there was no keeping it bottled in, but at the time it’s important for people to know that I wasn’t trying to set a business off of a newsletter. If anything, it was more like, Hey guys, don’t forget about me as I leave this fancy job. Like I’m still here, I’m still smart.I have unique ideas and, you know, here’s how to, here’s how to hear them.Nathan: [00:13:59] Oh, that’s interesting. And. You know, I, I think a lot of people would, would think about leaving the fancy corporate job or whatever, and just quitting without a plan or something like that. And like, sure, you can do that when you’re young and single. but you did it with a family.Khe: [00:14:14] Yeah. Yeah. Well, so, and so I always like to point out here is that I did very well financially, out of BlackRock. So yes, my wife is an artist. So I think the biggest question for us people is like, we didn’t have access to insurance. Once Cobra ran out. Separate conversation. But, I had 18 months of savings that I was willing to, I call it an angel investment in myself, like, so I was like an angel investment, 99% chance of it going to zero 1% chance of spectacular return, I guess.In my, my eyes were in that 1% now, not financial return yet, but definitely life return. and so, so I did have a cushion and I had larger obligation, but I had larger obligations as well. I think it’s really important for me to point out this cushion because. I delayed trying to make money because of this cushion.So I said no to certain opportunities because I was like, yeah, I don’t really want to do that. Even though I could have gotten cash that, that moment. And so, I couldn’t so, so an example was consulting. And so I think, you know, people wanted me to come in and do like org design. Cause I write a lot about, you know, future of work and like org design or kind of like motivational team coaching or just like my old job, like.Solving hedge fund problems. and so I didn’t want to do that. I did do, and this was the kind of the first moment that where I was like, Oh, this could be a thing because of my newsletter, someone from wall street reached out and said, could you coach my executive team? And that was something I would have, I was interested in.And that was something that I did. I probably, at that point had a thousand subscribers on MailChimp. and, and I did that, and that was that first. I mean, you know, it as an entrepreneur, when you have that boost of confidence, that’s like, Oh, we just jumped into level two. Right. And, and I didn’t want to be a coach, but considering I had no plan, I was like, this is a pretty cool job.It pays, you know, well enough to extend the 18 months to 24 months or 36 months. And it’s, it’s aligned with the kind of work that I’m doing. And so that was a real small, but very important tipping point that gave me the business confidence and the financial confidence that, Hey, you might be on to something Khe.Nathan: [00:16:50] Yeah, that’s good. Well, let’s talk more growth strategies. Let’s dive in on those. I’m curious, what’s worked for you to grow the newsletter from those thousand subscribers. You can share where it’s at now, and then some of the things that worked and then maybe some things that you thought would work and totally did not.Khe: [00:17:05] Yes, absolutely. So, so where are the newsletter is at now? it’s it’s 25,000. it’s probably got 7,000 of calling in it. Like I think if you removed all the calling, it would be like 45,000, but I don’t. I don’t care about that stuff, anymore, but I am tremendously proud of, of my 55% open rate, which includes a lot that’s includes launch emails, and we can talk about launch emails, but I write my launch emails, like their blog posts with like a slightly different flavor to them and people.Get very scared when they unsubscribed to a launch email, not the regular email, because again, that ethos of delivering value is, is there in my marketing strategy. W w we’ll come back to that. so, so I think, so there were a few key moments and they were all, my growth was all driven, by press and partnerships and they were okay.None of it was targeted. The biggest, the, the, the big. Two were CNN wrote an article about me called calling me Oprah for millennials on new year’s Eve of 2016. And they kept it on the front page of CNN money for three days. So it was like a feel-good story I was wearing. I looked better. they like, God does a great angle of me with like my favorite sweatshirt that just, it made me look like a hundred times cooler than I am in real life. and it stayed on the front page. So that took me probably from like, Four to 2000 to 10,000. It’s like 8,003 days.Nathan: [00:18:44] How did that story come about?Khe: [00:18:46] So I’ve had three good press hits that Bloomberg and barons. and those all came from the reporters being subscribed to the newsletter and they were just like, they’re like, this is a cause they were all, let me backtrack.The guy who leaves wall street, the fancy job on wall street with no plan and is willing to talk that’s most people, wall should be, are not willing to talk because they want the option to go back. It’s a very kind of closed lipped industry. I was the one to talk. I’m like, yeah. And I didn’t bad mouth, but I was just like, yeah, not for me.Yeah. It’s a crazy thing. I’m doing this newsletter. So they kind of observed that through my newsletter, that I had this kind of weird story. They probably were quite smart in the sense that like, that’s, that’s a story that people read, like the guy that quits, you know, fancy job when they’ll plan. And then they just cold emailed me and they’re like, Hey, we want to write a profile on you.It was like, okay, cool. Cool. and so, so those three were, were big drivers and I’ve been on two podcasts that really kind of were like thousand plus boosts. The first was Patrick O’Shaughnessys invest like the best. I was one of the, I would never make the cut now, like say like I went to yeah.Nathan: [00:20:08] I feel like I have that with a bunch of people where. I was friends with them, you know, we’re still friends and, and all that. And now they’re like a level of fame. I mean, now you have like, you know, supermodels and athletes and CEOs of many billion dollar companies, butKhe: [00:20:25] Totally. It totally, totally. I would never, I mean, he, he like it every term off this week. Right. but he did that and then he tweeted out my, my subscriber. I think he had like 30,000, I think it’s 150,000. Now. That was a big one. There was a gentleman by the name of Ozon Varel who actually is very private.He’s actually a ConvertKit guy, but he’s very private on ‘em. So he’s not really on social. He just has this. Newsletter. I think at the time it was 18,000, but they love him. And so when he shared my newsletter through his, I was a podcast guest of his, I think it was like 900 subscriptions in one day. I think he had the highest conversion rate, like, cause I could see these the worst by the way, Arianna Huffington, once retweeted, one of my articles.And I think, I got five subscribers from her 5 million Twitter followers who are probably all bots. So, so press in those early days was quite incredible. and it really, it just kind of put me on the map, but outside that there really? Yeah,Nathan: [00:21:38] Impressed for a second, for someone listening, maybe they have 5,000 subscribers right now, or 10,000 subscribers. And they’re like, you know, press is not something that I’ve ever considered. It feels like a, you just have to get lucky, you know, any of those sort of things. And, I believe in luck. I also believe in manufacturing so I like, what would you say to them?Khe: [00:22:00] I, I would say, yeah, that, and intuition of who’s writing about your space, and, and literally be friending them. is so powerful. and so, so it’s super powerful. And so what I did was, what would, I would tell people I didn’t do this myself, but find all the people. Who are quality writers in your domain all the way from like the wall street journal and the Ft down to, you know, local fire blog or, or low, you know, productivity blog.And it’s, it’s like being at a cocktail party. You wouldn’t go up to them and say, Hey, would you want to feature me? Do you want to interview me? But you follow them on Twitter. You like their posts, do you drop into their mentions at always, always starting with Adam value, adding value you get on their radar.When the moment’s right, maybe you slide into the DMS. That’s a little aggressive, but maybe, maybe you do that always leading with adding value. You look for the people that are quoting offer up new sources. really just like, think about who are the journalists or bloggers, how do I make their lives easier?How do I make their product better?Nathan: [00:23:28] I think a lot of people who, whether they’re doing sales or they’re trying to be, be featured in publications, or have a, like an idea of what they want their network to look like down the road. So people have this vague idea I want to be written about in publications and have these people’s friends and like, great.Let me see your top 100 list. And they’re like my, what. Well, your, your spreadsheet that has the list of all the places you want to be written about. And the people you want to, you know, 12, 24, 36 months from now, you want to be able to say, or your friends, and when you drop into their city, like shoot them a text and meet up for coffee.And they’re like, I don’t have that lesson. I’m like, well, how do you expect it to come? True. If you don’t have a…Khe: [00:24:11] Absolutely. And, and I, and I, I didn’t realize this, right. I, I, I was very naive in my early days where I thought just the best content rises to the top. Not that I’m anywhere close to the best content, and it’s like the best content doesn’t rise to the top. It has a better chance than to rising to the top than the worst content, but the best content paired with incredible distribution is.Was gangbusters. And I think it took me too long to figure that out. I got lucky that it kind of fell into my lap a few ways, but now it’s like a conscious strategy to, to understand who the journalists are tweet at them. And again, I don’t say like, write about me, write about me, write about me. I say, Hey, I saw you quoted, Tiago.You know, you should quote these seven other people. They’re really good too. And they have different perspectives. And I’m not even one of them, but that’s like quietly say, you know, like maybe I could be one of them too, but you can, like, you gotta be really delicate or these are really important relationship.Nathan: [00:25:16] Yeah, that makes sense. And I think a lot of people would, would have a takeaway of like, okay, let me recommend these three sources. One of which is me. And it’s like, no, you don’t even need to do that. Like be really useful. And then they’ll go, okay, who is it? Who is Nathan? Who is this? You know, like, let me click in and actually.Do a little bit of research. If I’m going to quote someone, they recommend, I should figure out who they are and there’s the dig. And they’re like, he should have recommended this himself. His stuff is just as good as the person that ran the store. Maybe the next one will be about him the growth side?Khe: [00:25:54] So I’ll tell you a few things that didn’t work and then I’ll go back to what has worked a lot. recently, cause now I’ve kind of hit a little bit of strife, but those are the things that didn’t work were Instagram, YouTube, just new channels. someone gave me this advice a long time ago. They’re like be good at one channel.Before you even consider a second channel. I messed with podcasting. I messed with Snapchat I messed with Instagram. and I forgot to say newsletters blogging. You can kind of two sides of the same coin. but I wasted a lot of time on things that have a visual component. YouTube, I think YouTube is a phenomenal platform.It is just a skill set that I don’t have right now. I have, you know, 30% of it and maybe some of the storytelling side, but the lighting and the fricking thumbnails, YouTube thumbnails, Jesus Christ. I just don’t.Nathan: [00:26:56] Get a shocked face looking at your, title…Khe: [00:26:58] Yeah. Ah so, Find the one thing that you’re really good at, and for me that was email and, you know, I’ve bounced between four newsletters a week to two.And Now I’m at two, which is kind of steady state, but for me, just firing up a new newsletter. People like it, people open it it’s quite easy for me at this point. and so the, so the mistakes were flirting. Too heavily with other mediums, particularly ones that were very visual. And that’s just a skill set that I, that I don’t have.Now ‘what’s work, I would say is two things. With three things. The unsexy answer is just publishing all the time. Just you just get this natural snowball of people sharing, right. That this kind of quiet compounding effect. And so it’s not a secret. It’s just, I’ve written 200 blog posts in the past three years and sent 200, 450 newsletters.Like if you maintain just above average quality, like stuff’s going to find you. So that’s. That’s the unsexy real answer. the sexier answer would be, you know, I did see an opportunity in SEO through, some of my involvement with notion. And so if you search notion, I’m basically one of the, I think I, I, I, the top Ricky.A search result on many, many different notion searches. And that was me seeing an opportunity and like, okay, no, it’s like knowing enough about the concepts of SEO and knowing a lot about notion to be like, Oh, okay. Making a bet. People are going to search for this. I have enough page rank that I’m not I’ll pass the mom and pop blog, but like, I don’t, I can’t hang with like the big bloggers, yet.But it was kind of like this moment and I like writing about it. Like, again, it’s like, I like writing about it and it adds value. And so I kind of jumped in there. And it’s the traffic on notion on my website. I’ll give you an example. My blog, before I started writing about notion was like 10,000 uniques a month.And it was mostly people linking from my newsletter to my posts and like a little Twitter stuff. Yeah. It was not very organic traffic. it was inorganic traffic. and then now with notion it’s like 70,000. So it’s like 60,000 uniques a month are just, through notion. So, so, and that leads to it’s and notion converts.It’s really easy to convert notion searchers, because you can just offer up a template as a lead magnet. And it’s like, the conversion rates are really, really good. I mean, notion people love free templates, so it’s, it’sNathan: [00:29:59] You say really good, is that like 3%? 5%.Khe: [00:30:02] Oh, some of them like 10%.Nathan: [00:30:04] 10? Yeah. That is, I mean, for, for organic traffic coming in, they’ve never heard of you before.Khe: [00:30:11] So it’s, uh, so that I lucked into that, but that, that there’s this whole challenge. I don’t want to be a notion blog Right. And so I need to be very mindful of people coming in and being like, Oh, this guy’s going to like, tell me about feature X, Y, Z of notion. And then I’m like, Have you ever thought about the fact that you’re going to die soon?They’re Like, like they’re like, what the heck did I sign up for it? So I need to really kind of balance balance that. And, and, and, and and also just accept that, you know, there’s a wave that I’m riding that is aligned with what I’m doing, but not totally aligned with what I’m doing. That at some phase that alignment will change and, you know, I could quickly.Drop back or, I’ll have to adapt, I’ll have to reassess. but that has worked really, really well for me. And then the last thing I’ll add is that I love doing free events. so I’m really good at email, but I’m also good at just standing up a for 15-minute presentations with a good Q&A with a good followup email.And so those events, I recently switched to podia, just cause I just. It’s got just this clean feel. I just loved the design of it. It’s just so. Clean, and it’s just on brand for me, and it’s easy to fire up a quick thing. so so I try to do one or two free events a month that are very low prep for me.I spend an hour creating a slide deck, 15 minutes, doing the backend of, you know, getting people in and out and, and that, and that’s been a really, really good way. of Again, creating value in a way that is, you know, very natural to me. and that doesn’t take a lot of, a lot of work.Nathan: [00:31:59] I mean those events, obviously they’re going out to your email subscribers.Khe: [00:32:03] Yeah.Nathan: [00:32:04] But is that through a partnership? IsKhe: [00:32:06] Yeah.It’s it’s through, I suspect I don’t have enough of the analytics, but I suspect that it gets forwarded around a lot through email. it’s I I’m getting better at partnerships. I don’t like. I’m not naturally inclined to do partnerships. Cause it does it it’s like that, that newsletter the reporter example where it’s like, but it’s like, here’s me. but, but I’m getting better at it because I really do think that they are, you know, Alia doll and I have had four. Like great sessions together where it’s very little prep and we can get a lot of our audiences together. So I do, I do need to like, get better at positioning it as a win-win for both of us.Because I just feel like a taker when I’m like, Hey, here’s my free event show, you know, show it to your audience. but I’ve been getting, I’ve been trying to push myself more, to do those partnerships and by the way everyone says, yes, I I think I’ve established enough of a quality-threshold reputation that they’re like, if we’re going to bring Khe on he’s not messing around, like it’s going to be tight, it’s going to be a useful, it’s gonna be useful.And so I think I need to get more confident to lead into that. And there was some imposter syndrome there and, and just be like, yeah, like my free events are good. so I should not feel ashamed or timid to go to someone and say, Hey, do you want to show this out? Because there I’m actually helping them.Nathan: [00:33:37] Yeah, that makes sense. And there’s, there’s a version of events that people used to do, like partnership webinars. And now it’s sort of the thing of like, maybe this is most common five years ago. something like that. And it still happens a lot, but it’s basically like, Hey, I’ll come teach a webinar to your audience at the back end of the webinar, I’ll pitch a course.And, then you’ll get 50% of the revenue and, there’s that version of it, which a lot of people do well, but I think what you’re talking about is, Hey, you and I have a topic that we both care about. And we, it’s the sort of thing that we riff on quietly behind the scenes with our friends, but I don’t have it fully formed and you have a lot better ideas on it.So why don’t we do it? A joint thing We’ll come together. We’re not promoting anything. All we’re saying is subscribe to each other’s newsletters. And that’s the sort of thing where, I mean, it’s almost easier content to make. When you think about the amount of prep that you and I did for this podcast, like.We’re just jumping on and talking about a topic that we love rather than puttingKhe: [00:34:42] Exactly.Nathan: [00:34:44] You know, hours of writing blog posts.Khe: [00:34:46] Exactly, exactly. But, and, and I think that, you know, I always offer the affiliate link and all that, but I don’t, I don’t. You know, I sell expensive online courses, like 900,000 $1000 to 1500. No, one’s going to like see me for five minutes and run to smash that buy button. Right. It’s just, that’s not how my, you know, it’s, it’s not B2B sales. but you’re not, you’re not smashing the buy button for 1500 until you get to know me. so, you know, those partnerships, unlike those ones from five years ago where the conversion takes place at the end of the webinar, it’s like you’re nurturing that lead for six months. Right. And so you almost, can’t like, yeah, you could get partnerships to drum up a launch just to build buzz around it.And there will be some quicker conversions, but my whole art, my whole ecosystem personally, is not set up to quickly convert anyone. Like You’ve got to get to know me. I want to earn your trust. And then a tiny percent of you are going to pay for a premium product.Nathan: [00:35:52] Yeah, that makes sense. Well, let’s, that’s a good transition into monetization. so I’d love to hear maybe going back, what were some of the first ways, beyond coaching that you made money from the newsletter, and then we can dive into, you know, the courses and all that now.Khe: [00:36:09] So it was always a bit of a, of a mish-mosh. So, coaching was always an anchor. Tenant. And I kind of dialed that up and down in different flavors of it throughout the six year period until January we’re actually shut down my coaching practice, where I was like, I actually, you are blog posts, like the ladders of wealth.I was like, I am not going to accept money for time anymore because I have, I found, I finally found product market fit. And it was time for me to invest in my business, not in, selling my time. and so coaching was like the main anchor tenant throughout it. you know, I did, I was surprisingly Patrion was like 15 to 20 K a year.So you know, it was, it was a real amount of money, not enough to live on, but that was one, after the. After the CNN article came out a bunch of like book people. Approached me. I actually didn’t get a book deal. I was, I wasn’t ready. I wasn’t talented enough. I still may not be telling enough, but back then, I definitely wasn’t.And, but I got like, again, through like the wall street, they, I kind of became the guy that can talk about and like happiness and money, the money happiness guy. And so a little, a bit of speaking. And, that was really, the portfolio L and I had up. part-time, I was an entrepreneur in residence and then became a contributing editor at a media company.So I drew a salary, a small salary there. So I kind of cobbled it together between those things. One thing that never worked for me. Was sponsorships now, despite having, you know, a decent size audience and, you know, high conversion, high open rates, high click rates. Here’s what I re what it took me a long time to realize about selling ads.You have to solve, selling ads is a very, very time-consuming process. You know, there were a few opportunities from friends and readers that could kind of come in. So assuming you could sell the ad, there was another part of the ad that was difficult, designing the app, right. Like helping them with a copy.And again, remember at that point I was one person. So I’m like in. Sketch, you know, trying to turn their PNG file and make the transparency come in before Canva comes out. I don’t know how the heck to do that. trying to be a graphic designer and a copywriter and it conversion writer all at the same time for not that much money.And then the ops behind it, how many people click with me at all? Like how many people clicked my ad and all the UTM stuff? it was just, it seemed like so obvious of a thing to do, but it was so brutally painful. Every time I did it, that I was like, I’m not doing this. And my goal for the, like my newsletter, my style is not going to be one with like, I think of my newsletter style is like a craft beer versus bud light.Where it’s like a very specific group of people are gonna be interested in it. Like a lot of people are gonna be like, this is not for me. It, it assumes a certain level of financial stability. It serves assumed level of intelligence, obsession with productivity, blah, blah, blah. So, ads never worked for me.I’m so glad that, I mean, now I’ll again, I’m like, Nope, Nope, Nope, no interest. so that. Yeah, no, no ads. and then a little bit of, you know, here and there affiliate fees. So like, there was always like some way to cobble it together, but, but to tell you the truth, like, I didn’t really start making. I made enough money to like it keep extending that 18 month runway and not like incinerate my savings.So I kept extending the runway, but I didn’t really make, you know, significant money where we’re like, I don’t have to like move money out of my savings account until the course business thought started about 18 months ago.Nathan: [00:40:23] Yeah, that makes sense. So what are the courses that you’re selling now?Khe: [00:40:26] So it’s really just one course. and the course is called supercharger productivity and it is in its sixth installment. And as I was telling you earlier, it is probably this one installment going across, a six-figure launch. Potentially while we’re talking. and so it’s very close and it launches, it closes cart closes tomorrow.So it’s a six week and it’s heavily, heavily inspired. I mean, Tiago is a friend and a mentor and it’s very heavily inspired by the way. Tiago has approached cohort based courses. It has a second brain feel to it. And I’ll tell you the interesting little story. Do you want me to tell you like how I didn’t set out to.Okay. So about, yeah, 18 months ago, I really start using notion a lot. And I just think it’s so cool. And as is the case with convert kit, if there is a product that really lights me up, I’m just going to talk about it all the time. No affiliate, I mean, I might collect affiliate here and there, but it’s like, that’s not the point.The point is to show how passionate I am, because. Things like can break it. Nathan, didn’t tell me to say this. Like they’ve changed. They’ve changed my life. I couldn’t, I couldn’t do this, in the company with a monkey on it. Yeah. and so, so I, so 18 months ago, so I started using notion and it was just like, I was a long time air table user before that I w I used Microsoft access, like our rest in peace macro, but I was just like, I liked firing up a small database cause like that’s how my brain works and that’s.How it’s way more powerful than the spreadsheet. And so I’d been using air table for a long time and heritage was an incredible product. I mean, it is incredible product. and then notion came out and it was, you know, I was just consumer enough that like air table had just too much stuff that wasn’t right for me and notion was just beat up, you know?Business solution enough to like, tip me and I love good design. Like I’m a sucker for products that like really light you up and like Apple, they give you that Apple feel to it. And, and it did that. So I started using it. And at that point, you know, I probably had 15,000 people on my email list and, you know, I would just write posts about notion and include them in my, my, email us.And people are like, what is this notion thing that K’s writing about? let’s look at it. And, and, and basically what happened, two things happen actually, I’ll come back to how they happened, but there’s a, there’s a really little important piece of internet history that, that, that. That makes me really lucky because right around that time loom came out.And what happened with loom was loom was the godsend that I didn’t know I needed because the whole thing about notion is like showing people how to do something That’s tricky. And, and that’s hard to do on YouTube. Like it’s just too slow. And so loom came out and all of a sudden I could just fire up these like one-minute videos, share them on Twitter, you know, anchor them in a blog post or something.And I just became one of the more, more active power users of notion on Twitter using loom. And again, better to be lucky than to be smart, like loom really opened that it opened a whole new distribution channel, a little-known secret Loom has a call-to-action button on their videos. and that button was converting really well for me, because think about it.I just wrote you a tutorial and I’m like, grab the template by hitting this button. In this prominently featured in this video, and then it was just like this fly. Yeah, exactly. And so it just kind of like, it was just firing. So also loom happened there and then, on my newsletter, people were like, Oh cool.Okay. Like we, we saw, we saw notion, cool, let’s try it. And then they would open notion and they would try to do what I did. And they were like, how the heck do you do that? Like I just see a white screen. And I saw that enough. And at that point, my stack of like my website, my email list, my, my call to act my CTAs It was legit enough that I just fired up a quick page on Gumroad and I like, Hey, I’ll teach you how to use notion in four weeks. And it’s 500 bucks and 500 bucks. 500 bucks, four weeks. And the reality was, I, I know this in hindsight was it was just people that want to, I’d say 80% of people just wanted to support me.Cause for four and a half years, I had been writing them great emails and had never really asked for anything. Other than Patrion page here and there. And they were just like, we just want to support you. And this thing looks cool, but I think it was like 80% support, 20% thing looks cool. So I fired that. I kind of drafted a syllabus really quick again, notion lends itself really well to like online teaching. Cause you just kinda like move the blocks around and it’s like giant Legos. and I kinda did that. Of course. And, I think what was that one? It was like 15,000 in revenue, maybe. something like that, 15 to 20.And so I did that course and people really liked it and I liked it. and so I realized I’m like, okay, I’m going to do, I’ll do this again. In three months. And so I did it again. I made it a little better, but basically the same thing. So here’s an important thing. Those first two, like I wasn’t selling them.I was just kind of like, here’s a link in my newsletter. And, you know, I was getting this like really low hanging fruit, not, not low-hanging fruit, but like I wasn’t persuading people to buy it. It was more like acts of kindness that they were supporting me versus like truly wanting the product. Third cohort somewhere on the third or fourth chord comes around.My timing’s a little bit iffy, but I started to work, with actually Tiago, marketing coach, Billy bras. And, and I was very skeptical of business coaches. and I, and it was outside of what I normally pay in it. And, but I trust Jago a lot and he’s like, okay, you’re good at email, this guy gets email marketing and he’s like, I promise you, it will pay for itself.And I was just like, he I’d like Tiago, you have never strayed me wrong, in this whole journey. So I went for it and that was, I mean, I have chills now. Like it totally changed the trajectory of my business, learning how to write emails. That can beNathan: [00:47:38] Yeah. So you didn’t set out to be a writer you set out to. Computer science into finance. And then you’re like, okay, somehow I’m willing to like someone become a writer and write this newsletter. You know, it’s getting 50% to be 5% open rates and crazy engagement, but that is a different skill, right?Writing for engagement writing for it to be shared is not the same.Khe: [00:48:05] No. And most people don’t most blockers don’t know this PSA to all you blogger is listening. Other start learning copywriting yesterday, right? Was that sort of, when’s the best. When’s the best time to plant a tree 20 years ago. When’s the second best time to find a tree today. You heard it here with the men, Nathan Berry understand copywriting, which by the way, copywriting in its own.Way is, is kind of a nebulous thing, right? It’s like the psychology of decision-making it’s it’s the psychology of persuasion. It’s specific words, choice it’s storytelling. So I basically, so I, I went, I worked Billy and it just blew my mind because here’s another thing I don’t like selling. I don’t like asking people for things.I have imposter syndrome around that. And, and, and mostly like, I just, it’s much easier to be like, here’s my gift of value. Go enjoy it in nature and smile. And I’m glad you’re happy. Cause I’m happy. You’re happy. It’s a different thing to be like, there’s this thing that’s really expensive. And I would like for you to buy it. it takes, it just takes a mindset shift, you know, especially now is moving out of like the, the little group of doing a favor people to like strangers. Right. And they were nurtured like strangers through, you know, different onboarding sequences and things like that, but they were strangers. So, Oh man. I mean, we could talk for hours about.This, but I’ll say here’s like the really important thing that I learned. And this is where people really struggle is I’m a left brain person. Most of my audience’s left brain. And so we think, but we’re wrong, but we think that facts and logic make us make decisions. We are wrong. we are wrong as buyers and we are wrong as sellers emotions make us buy things. and so I think that was the first thing to just recognize that like, you know, I was the guy that was listing off all of the features, right? So the first shift is going from features oriented marketing to benefit oriented marketing,Nathan: [00:50:31] Instead of saying, if you buy this course, you’re going to get four hours of video in 12 templates and 11 calls and you know, that kind of thing. So what are the benefits that you’re talking about instead?Khe: [00:50:41] So, one, so what are the benefits that the, the, the people in my course want, they want, to decrease their anxiety, they want to live life on their own terms. They want more free time. they want the confidence to take risk. they want more power. They want more money. They want more sex. they don’t know it in those words. and so, so I think the first shift was just knowing that that’s what they’re buying. Not like you will learn how self-referential database templates work and why that’s so cool. and it sounds crazy. And you think about like, you they’re like, Hey, you teach a course on notion.Like how are they going to get more power? Through your course. Right? And so the answer is this, well, what’s your system. We were talking about this. What’s your system for, keeping track of the in influential and powerful people in your industry that could benefit your business. You don’t have one. I will show you how you can.Boost your sales. This is mountain being like internet corny. I would show you how you can boost your sales in half the effort, with this system for relationship building, I call it, you know, th the powerful persuasion, you know, CRM, and it happens to be a notion. And so that was the shift. And I want, I want people to hear and to know that there’s nothing nebulous here.If you look at any advertisement, right? Classic one, you never own a Philly protect watch. You only handed down from generation to generation. It’s a fricking watch and you are telling me that that is the key to being a good father and an enduring legacy. It’s every, you see it everywhere. Banks, watches, cars, cigarettes, meditation apps, right?Sleep better worry less. That could be calm. That could be a sex toy, or that could be a nutrition powder. Right. Everyone wants that. And so that was the first shift. Is is just accepting that a knowing that it exists, you know, there are a lot of smart left-brained people left brain people. They have a blind spot because they don’t think that that works because they’re like, it wouldn’t work for me and they’re wrong because it does work on them. and then even, so they just have this massive blind spot. so that, that was like the first shift. It’s just knowing that exists. Now I see it everywhere. Right? Like you can’t, it’s like the rule of thirds, you can’t see outcome driven marketing. Right. and so that was the first shift and it sounds so simple, but if you, if you’ve never seen it, it’s kind of revolutionary and then you need to, you need to practice, right?Like it’s just a different, it’s a different style of writing. And then you need to, you know, You need to have a real, the same way. It’s a lot of the skills that writers use, right. Writers observe, but we tend to observe stories to prove points and to evoke a series of emotions or know, not decisions.Right. so it’s the same thing. now that I see outcome-oriented marketing, I can’t look at the billboard the same way. I can’t look at an HSBC ad, be free. I’m like, you’re a fricking bank. Like, so, so it involves seeing that. And then. Identifying it with your audience, right? Like my audience does want more power, but if you said this course will get you more power, they’re going to be like, yo, stay away Robert Green. but if you do say, you know, you can walk into a room and everyone will know you. They want that. that’s its own art form. In like identifying the language. So, you know, so I like, I write in, in my course part of the things is like you nudge them, you know, like I know you fall for shiny new toy syndrome.I know you bought the Oura ring thinking you’d get more sleep. But the real problem is that you drink too much. Like, yeah, like you can, you can kind of like, you know, there’s not many spaces where you can use the, Oura ring. In your marketing material, but if you’re my audience, like 80% of them, 95% of them have heard of it.So you gotta start tweaking and that’s the real art form. and I’ll pause there. There’s a third part. but I said a lot, so I want you to, I want to see if you want to double downNathan: [00:55:42] Example that came to mind for me. And this is, you know, my own uses of notion is like, you could pitch it in one way of, Use notion to organize your stories and writing research. Okay, great. You know, I’m sure lots of people do that. Lots of people want to do that. That’s fine. The thing that would speak to me is when you’re writing and you have the point that you want to make, and you’re about to use a story from your own life for the 17th time, don’t you wish you had, you know, like 11.Stories of great creators that you’d be like, Oh, this one, let me pull. And I have that because, you know, ISA on our team who, you know, well, cause we’ve, we’ve written one of these stories on you. She is like this incredible database. Like I go to her and I’m like, he said, give me a creator who has struggled for years.And it took them a long time of showing up consistently, and then they were successful. You’re like, Oh, let me give you here’s four stories, you know? As a writer, I want stability to pull in stories and quotes and get myself unstuck and bring interesting and novel things to my readers. And so really like sure, the solution that we use is inefficient database, but like, that’s the thing.And so if you were selling notion to writers, you would be all about that. And you’d be like, Oh yeah, we’ll implement it with these little things over here. But let me talk about the pain that you’re feeling and. And then the benefit, right? If we go all the way down, it would be, I’m standing in a room of people, right.And someone goes, Nathan, I love your writing. Cause every time I come across something, I discover someone new that I wasn’t following before. And all these bloggers use the same tired examples, but you have all these obscure. references, you know, and like, this is one example, but that’s the kind of thing that we’re talking aboutKhe: [00:57:41] Absolutely.Nathan: [00:57:43] Home to the feeling that we’re trying to create rather than just the features.Khe: [00:57:47] Totally. And actually, it’s funny that you say that one of the bullets in my sales, it didn’t make it into this latest version. Is your watch in amazement as the presentation slides right. Themselves.That’s a thing like that, that blockers don’t know how to do that. That’s a different skill set. And, and so that, that was a total ed. Again, it lends itself really well to email because emails intimate, you can go longer form on it. You don’t need visuals. So that combination of like really being dialed in with like, My segmenting and, and my different onboarding, you know, automations plus layering that skill on top of it was like totally, totally gangbusters.Nathan: [00:58:37] Yes, you did. You did a little copywriting thing where you left an open loop, that we could circle back to. a third thing. So let’s,Khe: [00:58:45] Yes. And it’s the rule of thirds too, so that the rule of thirds. So, so the third thing was actually something that makes it all come full circle. because there is, you know, people who are hearing this are probably. There’s probably some group of them. That’s like, this is very psychologically manipulative.What you’re talking about. this is why I hate capitalism, like et cetera, et cetera. And, and they’re, they’re, they’re not wrong. They’re not right, but they’re also not wrong. And so I think that, so two, two things happen. One was that, a lot. Of copywriting is around identifying pains, right? There’s a common, there’s a common copywriting, aphorism.That’s, it’s much easier to say sell painkillers than to sell vitamins, right? People want to pay money to make a pain, go away more than they want to pay money, to buy a better version of themselves. and that’s kind of a well, well known or at least well known to me, thing. So that, that that’s one thing.And that was, that’s kind of fundamentally at odds with the Rotterdam ethos. Because the robbery ethos is not to be like, you suck, you suck, you suck by this, do this, do this. It’s like, you’re awesome. Just this change can make you more awesome or this approach could make you better. And. In fact, one of the common copywriting formulas.This is for the left brainers who are skeptical of copywriting. There’s so many formulas and they actually are quite effective. one of the formulas is problem agitate solve. So you identify a problem. And then the agitate part is you like, take your knife and stick it into their hearts and like make the problem feel 10 times worse.And then you’re like, Oh, by the way, I can sell you something to make that go away. and. I, I just fundamentally don’t like doing that. And, and so I made a promise to myself that I’m not going to sell painkillers anymore. And I tried that and it worked, selling vitamins is much harder than selling painkillers.But what makes me more proud of this recent launch is that it was all through the message of vitamins. With better versions of yourself. Don’t get me wrong. We still called out to pains and frustrations, but the anchor wasn’t that like, you’re not good enough. The anchor is your good enough. You can be better.And I’m really proud of that. It was extremely difficult. It is extremely difficult. I’m not convinced, I’m not convinced that it’s a new skill that I have. It could be just a one-off fluke. and so that was like my, my, my second shift in copywriting. And then the last point for the skeptics out there, like, no, that, like if you have a product that you believe in.Then there’s nothing wrong with this, right? It’s the same way of like the way you write a headline. Like if you don’t write a good headline, no, one’s going to open your email. You could be the best writer in the world. No, one’s going to see your art, right? So if you, you, you could stand on the back of you, you would buy your own product at that price. Then you pair it with the version of selling that works for you, by the way, that’s how commerce works. Right? You have to convince people to buy things, but you know, it doesn’t work with mediocre products or it works until it stops working quite violently.Nathan: [01:02:27] Yeah, that makes sense. I want to talk a little bit about the structure of your team and where kind of where you’re taking the business. Cause that’s something, you know, if we think about a lifestyle business or we think about, you know, not building a big empire and like trying to build the next lynda.com or, or something else, I think people have a hard time imagining.What lives between cages operating completely by himself and running a newsletter and all the way at the other end of like trying to build the next billion dollar startup. So I’d love to hear how you think about that and what you’re building.Khe: [01:03:07] Well, I have a little PTSD from working out of wall street, where at any point in any minute of my life, someone could ruin the next 48 hours of my life. So, with a phone call or an email or, you know, meeting or something. So, so I’m a little scarred by that and it’s made me very, very, closed off to anyone being able to tell me what to do. Right. So I’ve really been very closed off in that regards. And again, I think I’m dealing with a lot of just the, the pain of like for 15 years being like, is this weekend mine or not? so, but there’s a few things that, that I’ve realized along the way is that that’s what I just said is based on the premise that if you add partners, Your life immediately becomes more complicated, right?Sometimes you can add partners in your life can become less complicated. Right? That’s got to be a possibility at least. and so I’ve been very closed off to, to that idea, but, there’s a few ways that I think about it. One is that there are very important priorities for me, which is, how I want to show up as a dad.Like being around the kids, picking them up, seeing their events, helping with the homeschooling. Like that is my number one priority. I have to make money, but like, that is a non-negotiable like, if, if someone’s like, you can make 20 times as much money, but you have to be gone one time, one week a month.No. Thanks. so being around my kids and my wife, is super important. the second is, you see that surfboard behind me, or maybe it’s being cropped, but, you know, surfing, like I surf every day and that’s my definition of wealth. I’m not wealthy. I mean, Depending on the definition I am. I’m not, but I’m not independently wealthy to the point that I can’t work.So I need to balance my hobbies and my loves and my passion with the thing that brings me income. And so a non-negotiable is, so I live walking distance to Manhattan beach, and I don’t have meetings between my first meetings at 1230 Pacific. So that I can watch the tides and the winds and just run out and surf for a couple hours, every day. so that is a non-negotiable for me. And the third is a test is like any anyone that I deal with. And again, I I’ve, I’ve earned the right in the, in some regards to, to get here because my business’s at a certain point, but anyone I deal with like, I want like a test and this is, this is less for like individual course clients.Cause I, I can’t there’s. They’re not faceless, but there’s a separation with them. But counterparties contractors, VA is, consultants. Like the test that I have employed with them is if it’s like the day after new year’s and it’s a Saturday and they want to talk, am I excited to talk to them? And if I am, then they should be in my orbit.They should be the kind of people, even clients like, coaching clients. I don’t have them anymore. So. So the thing that I’m protecting is my family life, my hobbies, my mental, like my spiritual health, my physical health, my emotional health, and who I spend my time with. And so if those three and what I work on, obviously if those four things are protected, then I’m willing to explore growing.Right. And so easy. If I were to grow an easy test would be, I’ll only hire people that I would not feel bad talking to on the Saturday after new year’s Eve. Right. and that might slow your recruiting process down. Like you probably can’t scale to, you know, Facebook levels with that threshold. but again, I don’t want to be Facebook levels.So, so I’ve been thinking about that more now that we have achieved product market fit and there is a path like. I don’t need to create all the slides for every course, right. It like that. That’s not a good use of my time. you know, I could have, I have a head of education. I could have a head of social, right.Because the thing works. And so now it’s about just like amping it up in the right places. But again, subject to those four constraints that I have as the business owner. The second thing that I’m more excited about is that, I believe that like, I’m good financially. Like my life’s fine. I, I love working.That’s an easy one. So like, like you’d have to carry me out. You know, I always say if I would, I have the day I had today, if I won the lottery yesterday, If I want a lot of yesterday, like I have been excited to talk to you for years, right. Like if I, if my bank account was different, I’d still want to have this conversation.Right. So, so that’s, that’s my, my test is like, if I, if I, if I, and I feel fortunate to be able to do that for the most, for the most part, so I’m good financially, but. We are sitting on a business that has product market fit, where the, the engines for growth are quite obvious to me at this point. and so what if I could give, give, transfer some of that growth or excess profits to people who aren’t me.I take whatever the thing I need to live, but that’s actually not that much. and so, so if you take people you’d want to spend January 2nd with, people who are uniquely talented and creative and they would want to, you know, get involved with an engine that could have life-changing ramifications to their personal lives.And that would make me so happy. I’m very open to that. And I’m lucky to sit in a community where those people are all around me, right. With the contractors, interns, like all of that, most of our team. And I, and I think, I don’t think, I think you wanted to hear about the team more than the like 10,000 foot psychology philosophy when you asked the question, but, you know, like if you look at our team now I have a, virtual assistant part-time.I have an intern part-time they all have full-time jobs or are in school. I have two, teaching assistants who are cohort based. and then we have eight, alumni mentors who are kind of like pop up, you know, event staff, so to speak. and, and that’s. And then I have a bunch of consultants for writing for, I, for copywriting, for SEO.Probably need to dial up some of my email automation. So looking at one there as well, and a bunch of consultants, so we could. Bring that some version of that in house? not in the, not too distant future, but again, it’s going to be looking at it’s. I told you about the spikes in my newsletter subscribers.It was, you know, for over six years, right. That’s one per year. So you know, where, where are the other spikes? It’s just from like, Just showing up and just chipping away at it. And so that’s, that’s always going to be the philosophy is like I always to use a baseball analogy. It’s like, I’m like trying to get the walk.If I can’t get the walk, I’ll go for the hit by the pitch. and if I’m really, really lucky, I’ll hit a signal. Like that’s, that’s, that’s what we play for.Nathan: [01:10:54] That makes sense. And I love what you’re saying about bringing in other people. And I, I used to have this idea of wanting to run a totally solo business and then. obviously I’m not doing that now. I’ve got 60 people on the team. but there’s just, it’s so much fun to bring people along for the journey and to have those people where, when they like drop you a Slack message and say, Hey, can you chat for a bit?You’re not like, Oh man. You’re like, you’re thinking like, yeah, absolutely. We haven’t caught up for a couple of weeks. Like that would be so much fun. Let’s do it. so anyway, I love people building teams on their own terms. Cause like for me not having a team at times, especially in the early days of ConvertKit was really stressful, but now, and a small team was really stressful, but now let’s say that we have a denial of service attack or spammers, or are doing nefarious things.Someone asked me the other day, Oh, do you get many fraudulent accounts signing up? And I was like, yeah, like two to 400 a day, you know, it’s a lot, But now there’s so many people that are able to take care of that. And they’re so much better at it than I am that like, to your point earlier, my life has gotten much less stressful because I’ve brought these people on.The last thing that I want to talk about is you have this idea that you talked about with the rad reads community of $10,000 an hour, where you’re at. And they’re like, that is absurd. $10,000 an hour work doesn’t exist. Like. Or they probably get into some, you know, political or philosophical argument about it.But I feel like this is the point that I’m trying to make with so many people about leverage and everything else, and you make it better than I do. So I would love for you to break it down of what you mean by $10,000 an hour work.Khe: [01:12:44] I love it. Yeah. I mean, it’s, I stand on the back of giants and like your, your ladders, well, post is, you know, one in one of those. and so it’s a very simple, simple matrix because you know, people are visual and, and, and on one axis, there’s a skill. So high-skill low skill and on one axis, there’s leverage.Low leverage and high leverage. And as you go through every quadrant, you go from $10 work to a hundred dollar work to a thousand dollars an hour work to $10,000 hour work. And so we can, we could go through there. They’re actually quite easy to go through. So $10 work is the easy threshold is like, can you do it hungover?Inbox zero Slack messages, formatting documents, you know, all that stuff. 10 hour work, high dopamine, low impact, low leverage, low skill, but we do a lot of it. A hundred dollar work is a little bit of a more, is a little trickier category, right? It’s a. It’s when you leverage the wrong thing or you’re leveraging like a low level, a lower level skill.And so a hundred dollar work could be things like learning GTD or, having good SOP, texts, expanders. It’s like things that definitely are efficient. but they might not be so effective. And, and in that quadrant, I always joke. I’m like, do you think Jeff Bezos uses a GTD. Right. Like Jeff Bezos has like eight things he needs to do.It’s like call a Janet Yellen, call Joe Biden, call, you know, president. She like, like he doesn’t need GTD for that. and so I think that, you know, we can get seduced into it, myself included in Zapier’s and convert kit automations, and all of that. It’s like, okay, they’re useful parts of your business, but by themselves, they don’t.They’re w they’re worthless. Right. So that gets you to the thousand dollar category, which is high skill, low leverage. And, the joke about the thousand dollars category is like, it’s the, it’s the high powered bankruptcy lawyer that charges a thousand dollars an hour. It’s the 10 X engineer that works for, you know, some flashy startup. That’s making a ridiculous salary.Nathan: [01:15:10] I just paid $600 an hour lawyers today for an and you’re like, there’s a lot of not quite thousand dollars an hour work going on, but you knowKhe: [01:15:21] Totally totally. And here’s where the thing here’s, here’s the brass tax it’s like thousand dollar an hour work, whether it’s $600. The point is you have a year unique skill that you can extract a market rent from. and it’s probably pretty defensible, like that, that bankruptcy lawyer is not that 600.He’s not worried about being unemployed. so let’s be clear. It’s an incredible life. Right. You are capturing, you’re capturing the profits of your hard earned work and expertise. Right. And especially if you’re salaried, right. You, you know, you get vacation, you get benefits. Like that is a very good life.It’s, it’s not that risky. It takes a while to get there. It’s quite low risk. and, and most people that’s all they want. Right. they want that comfort. Then there’s $10,000 work. Right? The thing is like, you can’t take a year off if you’re that lawyer, unless you’re independently wealthy at that point.And so then there’s this next part where the thing keeps working when you’re not working. Right. And so, you know, I had this great moment when I was out surfing and, and I came back and I noticed at my course that like an office hours had happened, the video was uploaded. The Slack channel was updated and all the customer service requests were responded to.And I’ve been surfing the entire time. I used to do all of those things. You used to do all of those things. And so $10,000 work is leveraging a unique skill. Right. So I, I, people often think that that’s like recruiting. I mean, recruiting is a big one. Recruiting into team building is a big way to build leverage, but let’s go back to the thing we were talking about, press, I would make the argument.And for those of you who, who, who don’t know how this podcast came about, I cold emailed, Nathan’s team. That’s a $10,000 email. Right because of your platform who this who’s going to see this, you know, it’s not, it might actually physically generate me $10,000, but it’s going to have a very amplifying effect on my business.So a one-minute a 15, second email is a $10,000 task. Those, all that stuff we were saying about journalists, right. For that type of person. It’s a $10,000 task. and so $10,000 work has this built in leverage it’s you it’s usually one to many, right? So, you know, you can write on Katie’s blog or you can write for the Washington, Washington post, write an op-ed for the Washington post.So it’s always got that, that element of one to many. There’s a big element of recruiting. There’s an element of brand, there’s an element of customer obsession. And then there’s this kind of like squishy, the squishy kind of hard to measure magic to it where it’s just like, you know, someone looks at you, Dave, and then they’re like, it’s like, he just teaches doing what he should be doing.Right. And you just like, you just get that feeling and, and when you see people like that, you just, they is there a gravitational pull towards some people want to be around them. People want to support their products. People want to talk about them. People want to link to their blog posts. So, so there is this kind of like, I think there’s a very formulaic way.It’s like, okay, I’m going to like email 10 journalists and do this and do this and do this. But it’s like, Can you also, you know, I always say you never want to, you never want to compete with someone who’s having fun and who genuinely cares. Right. That’s 10, if that’s my competitor, I’m, I’m screwed because that’s a competitor that’s on January 2nd with a hanger.So like, I can’t stop thinking about this essay because it’s just coming out of me. I might just have to sit down and write it right now. Yeah.Nathan: [01:19:31] Yeah. Oh, there’s so much in that, that I love, like, I mean that intersection between skill and leverage, where you can get someone who is, Taking this unique skill, whether it’s writing or design or email automation, you know, any of these things and making it reach a lot of people. I mean, so much of our $10,000 an hour work is going to be around audiences, you know, just because of the, the world that you and I both live in.But it takes the same amount of effort that laundry, you know, that you wrote, you know, one of, one of seven emails over the course of a launch or something, they’re the same amount of effort if they go out to a thousand people or 25 people, you know, and, and that’s, so any $10,000 an hour work is the kind of thing that takes the regular work.Copywriting normally is a, we’ll say it’s a thousand dollars an hour type of task. Yeah. You know, it is a, a very important skill if you’re doing it for other people, it’s worth being paid a lot for, but then what moves it to that last quadrant is when you’re like, I actually control the audience and have this leverage.And it goes up from there. I think one challenge. This is what I run into is,Well, no, not a challenge with that. I think it’s the challenge of living it out is that the tendency. Is when you find $10,000 an hour work, there’s not an unlimited amount available to you. You can’t just keep putting in more time and have it all be $10,000 an hour work. You have to build more leverage.The more leverage you’ve built. The more opportunity there is for this high value work. So the tendency is you have these big wins and this $10,000 an hour, and then you fill it in with a hundred dollars an hour work. Or often like $10 an hour work, if we’re honest, you know? And so it’s like a good point that you’ve made of, a lot of those times that you’ve said like, great, I did my $10,000 an hour work.I’m going to go surfing now. Whereas the chap that I fall into is great. Let me grind it out with a whole more work that later I’ll realize like, okay, that was $10 an hourKhe: [01:21:52] Totally. Then your constraint is to just move closer to the beach, right? I think too, that, that one of the, like the. Everyone has a portfolio of these things, right? If you only do $10,000 work, you’re kind of a dreamer that doesn’t know how to execute. And if you only do $10 at work, you’re the world’s best execution, a machine with no ideas.And so I think everyone, right? I mean, people always say they’re like, I’m 24, five years old. Like what can I do? That’s $10,000 work. I don’t have the, I don’t even have the thousand dollar work mean. It’s like, yeah, you’re in a phase of life where you are more focused on 10 and a hundred, but it doesn’t mean that you shouldn’t think about or do, right.Maybe try to commit to one meaningful relationship a month. Right. professional relationship a month, like that’s your $10,000 work, right? Just like Jeff Bezos is, is never going to be, you know, edit line, editing an email unless it’s to Joe Biden. Right. You know, cause that’s just, there’s no point in that.So everyone has their, their kind of portfolio, of the activities. Cause you kinda need all of them like in life, right? You need, you do need boring execution, right? Like you need to pay your bills, right. Or if you, you know, if someone else pays your bills, you need to make sure that that other person paid the bills or that, you know, you got to hire that person to pay your bill.So, so I think that th that portfolio approach is much more. um, sanguine than just being like, I need to be in the upperNathan: [01:23:32] Right. Well, there’s something that I like to do. One of my favorite questions at work is what would have to be true in order to, and then fill in the blank. Right? Cause it’s not, can you do this? And you’re like, well, let me tell you all the ways that I, all the reasons that I can’t do it can, you know, can we achieve this as a company?Oh, maybe, I don’t know. In the, you go, what would have to be true for us to hit this growth goal for us to land this level of candidate or whatever else. And it gets you into that mindset of like, Okay. I have all these reasons that showed up that we can’t do it, but you asked what would have to be true.So let me set those aside and then I’d say like, okay, well, our conversion rates would have to be this. Our brand would have to be at this level that when we send the cold email, someone actually reads it and says, Oh, can you make it interesting rather than be like, ah, no, the recruiting email, you know, whatever.Right. So it gets you into that mindset. So if someone is in the position, they’re thinking like, okay, there’s no $10,000 an hour work in. My world, you know, maybe there’s just $10 an hour work. I don’t have the skills. Then you can ask what would have to be true for this to move from $10 an hour, work to a thousand dollars an hour.And you’re like, okay, well, I would have to be an expert in this field. You rather than an expert designer, rather than a minor. and you can start to map that out and you, okay. What would have to be true for this activity that I’m doing to be $10,000 an hour work? Well, maybe my newsletter would need to be go out to 10,000 people instead of a hundred people.Maybe, you know, any of these other things. Maybe when I designed my launch, it has to be in a system that I can use again and again, instead of a one-timeasking that question of what would have to be true. we’ll start to get you thinking longterm.Khe: [01:25:18] Yeah. I made a note of that. You might,Nathan: [01:25:23] That sounds good. Well, we’ve, we’ve talked for a long time. We could keep talking forever. I think we’ll just have to do another round.Khe: [01:25:30] Oh, his dad to do at other…Nathan: [01:25:33] That’d be good. Well, where should people go to sign up for RadReads and follow your stuff? And then we’ll get into closing thoughts and all that.Khe: [01:25:39] Awesome. Yeah. Well, thank you again, like I said, you’ve been a big, a big, big inspiration, and you know how to build how to, how to show up, how to manage and how to lead. So I’m just grateful to be here and for building a kick-ass product that has really been transformational for my business. So, they, people can go to rad reads.co, no calm, just co sign up for the newsletter.You’ll see, you know, copywriting and a Notion, but also just a very, very passionate, personal, commitment to, to you. kind of learning more about yourself, learning how to live an intentional and epic life. And, the rest will take care of itself from there. I’m most active on Twitter. No YouTube, no Instagram.Nathan: [01:26:26] As you’re just thinking about bringing some of this RadReads ethos to the team, you know, to everyone listening, I’d love to hear. If you have something that you want to leave listeners with.Khe: [01:26:35] I would leave. Yeah, let’s so many good ones. I would, I would lead leave with, a quote actually from Tony Robbins is the, the quality of your life is measured by the quality of your questions. And so as your reframing, what would have to be true? I think, another one that I often push people to ask is like, what’s this for.Right. So like you want to switch from MailChimp to ConvertKit, like, what’s this for? Or like, do you want to open it, start a YouTube account. What’s this for? And then really pull on, like, don’t be satisfied with the first answer. Go buy a one level deeper, go to the second answer, go to a third answer.And actually ironically, like copywriting, you’ll probably land on some deeper human need that you have. And once you get into that need, then you can really kind of go back up and be like, Oh, this is, you know, the war or I’m going to actually solve this deeper need. It might be a tool to help you get there.But to really understand that, like what’s the what’s driving, it is a real gift that, that you can give to yourself.Nathan: [01:27:53] I love it. All right. Well, everyone goes sign for RadReads. Okay. Thanks for hanging out. And we’ll chat again soon,Khe: [01:27:59] My pleasure, Nathan. Thank you.

Louis Nicholls is the co-founder of SparkLoop, an email newsletter referral program where you can have each of your subscribers refer their friends to unlock cool rewards.SparkLoop is amazing. They’re growing really quickly in the audience-building space and ConvertKit actually gives away free SparkLoop accounts to all of our creative pro customers.In today’s show, Louis talks about how to increase your email list growth rate by more than 30% with a referral program. He also gives his (hot!) take on paid newsletters, discusses how best to monetize your audience, and so much more.Links & Resources James Clear Tim Ferriss Brennan Dunn Anne-Laure’s Ness Labs Art of Newsletters 018: Anne-Laure Le Cunff – Building a Loyal Audience & Growing Your Newsletter Louis Nicholls’ Links SparkLoop’s Referral University Personal site: LouisNicholls.com Twitter: @louisnicholls_ Episode TranscriptLouis: [00:00:00] I think you should be creating content probably in other places. Most often people who get to a hundred subscribers and carry on, they get there relatively quickly because they’ve been being useful in other places. For example, on Twitter, in forums, you should focus less on getting more subscribers through the door and more on being useful and creating content. Nathan: [00:00:25] In today’s episode, I talked to Louis Nicholls from SparkLoop and SparkLoop is an email newsletter referral program where you can have each of your subscribers refer their friends to unlock cool rewards. So, for example, if you refer three friends to a newsletter, you could get access to the special content, 10 friends, you get a t-shirt 50 friends, you get something extra incredible.SparkLoop is amazing. They’re growing really quickly in the audience, in the audience building space and, ConvertKit’s actually an investor in SparkLoop and we give away SparkLoop accounts for free to all of our creative pro customers. So the article is so good. Talk about how to grow your email list by more than, or increase your email list growth rate by more than 30% with a referral program, as well as Louis’ take on paid newsletters, how best to monetize your audience and so much more.So let’s dive in.Louis, welcome to the show.Louis: [00:01:17] Nathan. Thanks for having me, excited to be here.Nathan: [00:01:19] All right, so let’s talk SparkLoop right at first. you’ve been in the newsletter industry for awhile. You’ve been watching this whole space, building lists of your own. What was the impetus for wanting to start SparkLoop?Louis: [00:01:32] Yeah, I’m kind of half from me, but also half from my co-founder Manuel. So Manuel had been running a, like a generic referral tool called referral hero for a couple of years. It was, or it still is pretty successful at a lot of clients, you know, larger fortune five hundreds as well as smaller ones. And that was in like the generic referral space.So mainly e-commerce SaaS and so on. And I was at that point where I just sold my last company was kind of looking around for things to do and keeping myself kind of engaged. So I was running a small newsletter, doing a small course teaching founders, how to do sales and doing kind of like that classic.I call it marketing consulting, but really just kind of helping other founders who reached out with some kind of like consulting gigs. And one of them ended up being a paid newsletter in like the flight steals space. And they, I think they probably, at that point seeing what morning brew was doing with their referral program and they were really eager to add one in.So they asked if I knew of anyone who could help do that. And I said, well, I’ve done referral programs before. And the software I’ve used is from my friend, Manuel, who runs her federal hero. So I thought, well, if anyone knows what tool to do or what, what tool to use, it’s going to be Manuel. So I’ll ask him, reach out to Manuel.And he says, well, you can kind of make referral hero, do this with a lot of work. there isn’t really a better option out there. But it’s funny you say this cause you’re like the fourth person this week has asked me if we can get referral here at working with newsletters. So maybe we should look a bit into this together.And, that’s kind of, I think where it starts, if we didn’t originally planned the Spock week to be a new tool necessarily, we thought it could be kind of inside of referral Europe. But as we. Kind of understood more about exactly how it was supposed to work and kind of the integrations that newsletters need to be successful. We’ve realized it really needs its own dashboard and its own integrations. And at that point it may as well be a separate product.Nathan: [00:03:46] Yeah. And so we’re recording this in January, 2021. when was that? That, you two started working on.Louis: [00:03:55] I think the first time we probably started talking about it was in summer 2019. Yeah. So about a year and a half ago. Nathan: [00:04:03] Yeah. And so now, I mean, SparkLoop powering referral programs for a whole bunch of people. I know James Clear, a lot of ConvertKit customers, who are some other examples that you could share?Louis: [00:04:15] Yeah. James Clear, Tim Ferriss would be two big ones from kind of that personality author space, I guess. then we have a lot of info-product creators using us people like Vernon Dunn. and Anne-Laure from Ness Labs, who I know you had on the, on the podcast recently. And then we’re seeing a lot of interest from kind of the, the media companies as well.So, Punchbowl news, we just recently launched a using us front office sports, people like that.Nathan: [00:04:46] Nice. Okay. So when someone’s thinking about a referral program, What are some of those misconceptions, right. Someone comes in and they’re, they’re like, I’m going to copy. What morning brew does exactly. Like, and then it’s going to explode. We’re going to have viral growth. Like it’s going to solve all of my, user acquisition problems.What are some of the things that people come in with and where do you either say, no, this is actually the best practice or like sort of reset their expectations.Louis: [00:05:16] Yeah. I mean, how long do you have we could, we could go at this all day, I think. so I’ll start with some common ones. The, I think the most common one we see straight off the bat is that some people that newsletters are just too small for it to be worth one. so if you have, if you’re a hundred or 200 subscribers, yes, you can grow.I don’t know, 20%, 50% faster with a referral program, but 20 or 50% of five new subscribers a week, just isn’t worth the time you’d put into it. Right. And you could be cross posting or doing something way more useful at the time instead. so that’s the main one when we seeNathan: [00:05:55] What sort of minimum threshold that it, that it does make sense.Louis: [00:05:59] Yeah. Good questions. So I think if you don’t monetize your newsletter yet, or you monetize it via sponsorships, Then you’re probably looking at somewhere between the thousand to 2000 subscriber. Mark is when it starts to really be something you should think about. If you do monetize, especially if you have, you know, courses or something like that, where you’re like the value of a lifetime value of a subscriber is, is high, is 20, 30, 40, $50.Then it can make sense, you know, with hundreds subscribers. I mean, I use it for sales to founders, my newsletter and cost because. I only have about 1,500 or I did only have about 1,500 subscribers on that list, but each of them was worth about $56 on average. So even getting two or three new subscribers for me a month is a big deal.Nathan: [00:06:51] Yeah, that makes sense. when you’re looking at. I feel like I have so many different questions, but when you’re looking at the revenue per subscriber across lists, since you have this insight now across a whole bunch of different newsletters, what are some of those defining things? Is it always the highest when someone has a paid course?Louis: [00:07:13] These are, I think one of the things that we’ve seen so far that do tend to have the highest lifetime value per subscriber, it depends. So yeah, I think cost is probably like the highest consistent one that we’ve seen on average. And then you also have services, which are super hard to define because you’ll have maybe 5,000 people and list.And one of them is going to pay $200,000, but you don’t know which one it is. So like leaving them aside. Cause that’s like a whole different thing. Nathan: [00:07:46] I would say it’s to average that where you’re saying like, Oh, I made $200,000 off the list. So every subscriber is worth $200. It’s like, no. Yes and no. Like, technically that is the average and no, you shouldn’t make business decisions based off of that.Louis: [00:08:01] Totally. Yeah, totally. So I think info-product creates is probably at the top. And then you have paid newsletters, paid communities as well, which tends to be a tiny bit lower. then after that you have sponsorships affiliates, stuff like that. Yeah.Nathan: [00:08:15] Yeah. Okay. So going back to the, the difference in what people are expecting from a referral program, you know, versus what they should actually do, what are some of those things that come to mind?Louis: [00:08:26] Yeah. So we talked about already about the, the idea that you don’t want to start when you’re too small. The other thing you have to bear in mind is that you have to be sending regular emails for it to be worthwhile because. You need to be asking people often to share. And if you only send an email every month or every three weeks or so, that doesn’t give you very many opportunities to, to nudge people to, to refer.So they tend to see pretty poor results. And it, it does tend to be the daily newsletters. Like the morning brew Punchbowl will get the best results. And then, you know, twice a week weekly, they get great results as well. Anything where you’re not sending at least once every week tends to be more difficult.Nathan: [00:09:10] Yeah, that makes sense. And is that, is that a call to action that you’re putting in every email? is that something that you do dedicated emails for? How, how does it perform best?Louis: [00:09:23] What we tend to see is that you want to have a, a call to action, like a referral section inside of every email that you sent out. Unless that email has some other really important call to action in it. So if you’re launching a new course or you really want to drive people to a particular link particular website or video, then maybe skip that week because you don’t want people going off in different directions and doing different things.But in general, you’d have it in every single newsletter. Normally either towards the bottom or somewhere in the middle, where people are going to see it. And then we also recommend that you probably want to. Have a specific welcome email. So when someone joins your newsletter, you presumably have a welcome sequence or several welcome sequences, depending on whether people, you know, where people joined from or why they joined.And what you normally don’t want to do is to introduce the referral program in email one, because they haven’t had a chance to, to trust and get to know you yet, but normally a couple of days later. So between. Seven and 14 days after they sign up, you want to say, Hey, you know, I, I hope you’re really enjoying the content.It’s all free. It would mean the world to me. If you would share it with a couple of people that you think will get value as well. And I’ll have that email somewhere in that.Nathan: [00:10:42] That makes sense. Yeah. I mean, you’re, you’re effectively asking for a sale in some way, right? In this case, they’re not paying with dollars. They’re paying with, A bit of their time and their reputation, right. Where if I’m saying, Hey, you know, my friend Barrett, like Louie’s email is really good, you know, go pay attention to it.I’m like attaching a little bit of my reputation to that. And so if you’re doing that before, there’s trust built up where you’re saying, Hey, you should, you should go pitch your friends on this. And you know, we’re on email one or email two. It’s probably premature.Louis: [00:11:16] Sure. Oh, yeah, for sure. I think that’s an interesting point that you raise about the, I mean, the trust is absolutely spot on, but also that you’re, you’re asking people to pay, like to pay you in a way. we do see that you can almost separate. The approach that you take with the referral program out into two kind of distinct ones where what most people are used to is kind of like the really transactional approach of morning brew, where it’s quite obvious, they’re saying, Hey, please go and do this work for us.Please go and refer. These people actively work towards it to get this reward, this price that we’re giving you in return for the work. And that can work well. But it’s also like once you have that, once you state that relationship with your subscribers, then it’s very difficult to roll back from that from asking them to do work for you.So what we normally recommend is to start off with more of a nudge and to say, Hey, we’re not asking you to go and do work for us, but we know for example, Nathan, we know that you enjoy. Might newsletter about whatever it is. we know that that must be a lot of other people on the ConvertKit team who really should be reading this as well, that you should be sharing it with.So as a thank you for sharing it with them, he has a small little thing just to say, thank you, basically.Nathan: [00:12:34] And so what’s an example of one of those small things that you would do where it doesn’t feel as transactional, or like this big ask.Louis: [00:12:43] Yeah. So that’s, that’s a really interesting thing as well. So most people they come in and they naturally assume when it comes to rewards that they need to do either some kind of discount, so money off something, or that they need to do some form of physical swag or gift. So maybe mugs t-shirts ad pod cases, stickers, even something like that.And. Those are expensive. Firstly, you know, you don’t necessarily want to be paying for those and then shipping them and coordinating all of that. It can be a pain, but also secondly, they tend to underperform from what we’ve seen compared to what makes really good rewards, which is rewards in our experience that are based around either exclusivity or around urgency.Either getting access to something that there’s no other way for them to get access to often that’s content, maybe in your case, it could be. and so James clear, for example, has a secret newsletter that he sends every month, which you can only get, if you make three referrals or we’ve seen people do, kind of small coffee chats via zoom once a month of inside of clubs.We’ve seen all of this, for example, who will say, you can get a, a chapter from the book that I ended up removing from the book, and then no one else has read. For example, that kind of thing. It’s something that you can only get if you, you know, if you make the referral something exclusive or on the urgency side, which works really well for infoproduct creative schools creates us, is to say, I’m going to give you early access to something.So when I had my last launch at the sales of founders course, for example, the course was launching on a Monday, on a Wednesday. I emailed my list and said, Hey, on Monday on Monday, you’re going to get access to this thing for free. If you’d like to get it on Friday, just share this link with two people.And just that act of doing it grew my list by about 30%, even though it was only a two day difference, which you’d never think of it working like that.Nathan: [00:14:49] Well, and there’s no marginal cost to it, right. Where I would assume coming in that. I need to be on the other camp of, do this thing and I will send you a t-shirt and you’re like, well, that’s a, that’s a $15 all in cost, you know? And so what I hear you saying is sure, you can do that, but here’s a digital version that has no additional costs that performs just as well, or even sometimes better.Louis: [00:15:16] Yeah, totally. I mean, if you think about where the sweat comes from, it’s often because the really big newsletters that got popular with referral programs, the main two really are morning brew and the skin and that both very strongly branded newsletters focused mainly on college students and college students were really identify with it and they would really like to have a free t-shirt.If you’re selling to, or if you’re writing emails, if you’re creating content for people who are maybe professionals that all of a sudden a free t-shirt, if you’re making 150 K a year, it doesn’t really move the needle that much. Whereas, a coffee chat with other people who are in your industry would be super interesting for you.Nathan: [00:15:59] Yeah, that makes sense. Okay. So, let’s put on our free consulting hats for a second. And let’s say hypothetically, someone named Nathan Barry had a newsletter of. 26,000 subscribers and was considering starting a referral program. all hypothetical, of course. what would, what would you recommend, that program would look like?Louis: [00:16:22] I think the first, I mean, I’d have to ask some questions first. So I think the first question I would probably ask is why people are signing up for the newsletter. So what did they turn up there for?Nathan: [00:16:31] Yeah. that’s a good question. So it’s a lot of content on a design marketing and audience growth, combined with, You know how to run a startup or a money or that sort of thing. Honestly, it’s a very, very broad newsletter, right? Things like this podcast are going out to it. and another point, you know, just for, for references, it’s a list that, didn’t go cold, but definitely got a lot colder as I focused on convert kit.You know, so for example, the list peaked at 30,000 or 32,000 subscribers, and I’ve just slowly kind of trimmed it down and cleaned it. as it, you know, it’s not growing fast, it’s growing, I don’t know, 2010 to 20 subscribers a day, not the hundreds of subscribers a day that you would expect to get to those numbers.Louis: [00:17:21] Sure. Sure. Yeah. That’s interesting. So then the other question that I tend to ask as well is, how you, or what you want the people on your newsletter list to do. So once someone subscribes, what is kind of the, the end goal for them, are you monetizing in some ways that something like them, some action you’d like them to take.Nathan: [00:17:41] I want them all to sign up for ConvertKit. but I’m gonna say at this point, convert, it is. So much bigger, whereas four years ago, five years ago, my audience was driving ConvertKit and, and now, you know, ConvertKit’s email list is 10 to 20 times the size of, of my individual audience. So, Yes, they could buy the books and courses, but I don’t push those very much.So I think it’s, you know, I was talking to, on Malik who, started to gigging, years ago and now as a venture capitalist investor and he recently switched to convert kit and he had this, this thing that I hope he executes on this idea of. Saying, he’s only going to allow 10,000 people on his email list.He wants the 10,000 most engaged people, right? So he wants like a 70% open rate or higher. And if someone doesn’t open it consistently, he’s going to kick them out and then let in the next like 500 as he clears out that, that slot. And I don’t know that I’d ever go that extreme though. Like I liked the idea, but I would want people who.I would want the most engaged people who are there for a conversation or who are really fans of the work, rather than just getting to the largest possible list.Louis: [00:19:01] Got it. Okay. Okay. Yeah. So I love that idea, right? I’m not sure I’d have the audience to pull it off, but it’s a, it’s a fun one. so normally when people have a list they tend to have, they tend to be trying to monetize the list in some way, right. If you’re using a referral program, So you would maybe, for example, with one of your books, I want to go eBooks.What you might do is to say, okay, well, I would really love people who sign up to buy one of the books and then maybe they will see through that. They will learn that they should use convert kit. Or they will take a course of mine or they will, I don’t know, spread the word in some way internally. So the company buys convert kit or something like that.So what you normally do that is you would try and tailor the reward to be something that someone who’s kind of on the fence about buying the book would want. So it might be a free chapter from the book, for example, and you’d set that up as. W when it comes to rewards strategy, which isn’t something we really talked about, what you tend to want is to always have a reward that you can win.So making between one, three referrals. So that’s really easy to win because if you have a reward at that level, then everyone who sees it thinks, okay. Yeah, sure. If I share this on Twitter, if I share this with a couple of friends, I’m going to get at least one or at least two people to sign up the short.So I’m definitely going to get this thing. So I would have something in that space for between one and two referrals. It’s digital, it’s easy for you to do, you know, you can set up an automation and convert kit or your email tool to just send them the free chapter as a, as a download link on. So they make the number for ferals and you don’t really have to think about it again.And then what you might do on top of that is to have another reward somewhere between maybe five and 20 referrals. And that would probably be something that’s slightly more, more exclusive. The people are probably going to have to work a tiny bit towards, or they’re going to have to have quite a big list or quite a big kind of social sphere to be able to get straight off with one chat.And that in your case, again, it’s difficult because you’re not trying to monetize directly, but something you might do that, that we’ve seen work well is for example, to say, okay, a lot of the people on your list, for example, probably marketers and would probably like to get themselves featured or in front of other people who are also on the list.So you might say, well, I will give a shout out at the bottom to the three people each week who make the most referrals or, once you make 20 referrals, I will give you a big shout-out in the footnotes of the newsletter or something like that.Nathan: [00:21:34] Yeah, that makes all that sense. Something that comes to mind is, there’s a lot of content that I. Am intrigued on or want to write a write about around money. And particularly like, I have a lot of people on my list who say, have followed whatever in authority or something else over time, they execute on that.And now they’ve made a hundred thousand dollars a year online, whereas before they were making 40,000 in their old job, or now they’re making 250,000 a year. And they’re like, what? Even. What is happening, you know, you, if you go from 60,000 to 250,000, which you can do from a single, you know, course launch product launch, your world is completely different.But if you post about that sort of thing publicly, then there’s all like, you have to deal with everyone saying like, look at you. You’re now in the 1%, or I don’t know, like all the negative talk around it. And so one thing that came to mind is doing this like a secret course. That, you know, I’m on money that shares a bunch of these things that once you’re at this level, you should pay attention to, but that requires, you know, three or five or 10 referrals.And I think that would be really interesting, cause it both is only for the most engaged people, which will prevent some of the public backlash. and you know, it could be a compelling reward.Louis: [00:22:58] Totally took. And I think, you know, that’s a great title. And also with it being, I mean, it’s, it’s your like Nathan Barry newsletter write people up as to hear from you. And that has similarities with James clear with the Tim Ferriss newsletter, where really what they, what subscribers they want at the end of the day is they want more James.They want more Tim and they want more. Nathan. so having something like that, that’s exclusive, that’s an insider thing that you can give them is a great way of doing it. And maybe even layering on like, A monthly coffee chat or every quarter, maybe a coffee chat, something like that. Just some way that people can connect, that obviously in your case, you wouldn’t want it to take up too much time, but something where, you know, people can get more of what they signed up for, which is more Nathan barrier, basically.Nathan: [00:23:44] That makes sense. What are some of your favorite programs that you’ve seen people put together? We talked about James. what are some other examples that people Vic’s executed really well on the reward tiers or how they promote it?Louis: [00:23:57] Yeah. So something I’ve really liked is I’m a manual stacked marketer and he does a great job of mixing in. digital and physical rewards together. So he keeps the first couple of reward, referrals that people would make. So up to about five referrals, it’s all digital things that are completely free for him to give away, like, access early access to conference tickets and stuff like that.And then from there he layers in physical rewards. So a mug, a t-shirt and so on, and he actually takes it all the way up to, I think for a thousand referrals, he will fly you to Vienna to get lunch with him. which I don’t think has happened yet, but there are people out in that far away.Nathan: [00:24:44] I can see that I, in a post COVID world, I have an absurd number of airline points. I, you know, that could make them,Louis: [00:24:51] Yeah. Yeah. I mean, we we’ve had people make over a thousand referrals before. So I was saying this to, to Trevor mackendrick who uses us in his newsletter and he, his, his kind of big, shiny, reward tier at the top. And the motivational one that kind of grabs headlines and gets people talking about it is I think for a thousand referrals, he will buy you a billboard in San Francisco and put whatever you want on it.And so I was explaining that there’s a chance that he may actually have to do that. So yeah.Nathan: [00:25:24] Yeah. what, obviously you get these outliers of a thousand referrals. Are those always coming from someone who has a big audience? or do you see it from, you know, a subscriber who is really just hustling, like crazy.Louis: [00:25:41] yeah, you don’t tend to see too many people hustling, like. Crazy to be honest. And you, you don’t normally want that because if they’re working for it, then the engagement of the people that sending it away is probably going to be quite low. so that’s fine. If you have like a morning group or a hustle style audience, where really they’re happy to get a lot of people through the door and their audience is super broad and people will, you know, they do an amazing job in the first two weeks, making sure that people who aren’t a good fit, segmented out and cleaned away.And it’s all fine. if you were running a more niche newsletter, especially if you have like an info product or something like that, a paid newsletter, then you really are looking for engaged subscribers, people who are really gonna identify with it. So you, you almost don’t want their awards to be too good to the point where people will start to try and trick the system and get people to sign up who maybe wouldn’t have been too interested.Nathan: [00:26:33] That makes sense. I think a fear that people would have with a referral system or particularly. Referral system, is it that engagement would be lower over time, right? That those subscribers would be, less than one thing that I’m realizing is inside the reporting and convert, you could segment down to referred subscribers and then just see their open rates trending over time and compare that to, you know, the more general cohort or a cohort that came from paid advertising, or that came purely from organic search.What have you seen is that. Does that fear play play out or are they just as engaged as those that sign up organically?Louis: [00:27:13] Yeah. I mean, I don’t want to sound like I’m saying referral programs are the best for everything they’re not, but when it comes to engagement, I think anybody who uses spark group and probably anybody who uses any referral program would say that the engagement is better than pretty much any other source they get.I’ve heard that engagement from people who’ve come. Fire influences is pretty good. I think that was the head of growth at morning brew was talking about that a couple of weeks ago when we were chatting. But other than that, everything I’ve heard so far is basically that the people who come from referrals, because the difference between like people coming from a giveaway, like a traditional giveaway, right?If you go on Twitter and say, Hey, sign up to my newsletter this week, and you’ll be in with a chance to win a Mac book or something like that, which people do well, you get loads of people who sign up because they want to win that book. Whereas, if you tell your existing audience, Hey, I’m going to give away a signed copy of my book this week to one person who makes at least one referral, or the people who they’ve referred.They’ve only signed up probably through your existing landing page or through like a landing page, which is they’re there for the newsletter. Right. But they’re not only there for the newsletter that they have for their newsletter. They know that friend is subscribed to. And that they’ve had from like, recommended to them and that they can chat about with that friend.So that likely to be way back to quality than anything else. And what we actually see is that, especially if you’re going to go out and do paid advertising. So if you’re going to do Facebook ads, for example, to your newsletter, Then, what you really want to do is you want to add in a referral program first, you want to see which people are researching and which people are being referred.And then you want to build a custom audience around that because those people are likely to be much better, kind of acquisition sources through Facebook for a custom audience, then just, you know, trying to build an audience in general.Nathan: [00:29:02] Yeah, that makes a lot of sense. And then, then you’re going to get, you know, for every dollar spent on Facebook to get a subscriber, you’re going to get a little bit more of an incremental gains of, you know, another quarter of a subscriber on average or something like that.What are you seeing on, like, on some of the numbers, you know, if we were to spin up a, a referral program and execute it, maybe it’s not the most, perfectly executed referral program ever, but we’re following these best practices, making compelling content and that kind of thing, say to a 25,000 subscriber list, I don’t know, 30% open rates, something fairly average. where do you see in a left on, on subscriptions?Louis: [00:29:45] Yeah. So what we tend to to measure by is, is kind of the growth rate, right? So if you’re growing, let’s say. Take X percent a week or X percent a month. What difference do we make to that? It’s kind of how we measure ourselves. And what we tend to say is all we tend to see is that anybody with completely free digital rewards that cost them nothing, not putting a lot of thought into it, not running regular referral giveaways, which make a massive difference at really kind of trying to do the bare minimum, of, of, of time and, and money investment.They can get to somewhere between 15 and 20% faster growth with a referral program. the average that we have across all of our sparkly customers is about 35% at the moment, which is just slightly higher than I think the morning brew has from what I’ve read. and I mean, it goes the whole rain track.We’ve had people who have consistently grown 300% faster, 400% vested, but. That’s sending daily newsletters. They have a super like gamified sequence. They have this wide audience normally of, of teens or of college students who are really interested in signing up. So it’s, if you have that perfect storm, that really the sky’s the limit, but yeah,Nathan: [00:31:01] Anything could change on that, but that’s a great way to represent it, of whatever momentum you already have. We’re looking for a lift on that rather than, you know, again, it goes back to if you, if the subscribers aren’t there to begin with it, doesn’t, it doesn’t work. This is only a lift on what’s already happening.Louis: [00:31:22] Yeah, exactly. I mean, the truth is that people do even without a referral program, you will have some people sharing. You will have people writing about the newsletter. You will have people sharing it in Facebook groups. And if you’re like without doing anything else, if you’re seeing basically no growth.That’s normally something that’s gone wrong, that, that a referral program isn’t going to fix in the same way, the probably paid ads. Also, aren’t going to fix that. There’s something more fundamental that needs to be, to be sorted out.Nathan: [00:31:51] can you break from referral programs for a little bit like newsletters in general, newsletters are having this, this resurgence, right. There’s been various waves of it. One was in the blogging. I feel like when maybe it’s just when I came into blogging, but when there’s a big wave in 2008 to 2010 something, 2012, something like that, I feel like tiny letter push newsletters a lot.And. 2013, 14, somewhere in there and then died often. Then now it’s sub stack and your view and convert kit and all of us, right? There’s this big wave. And in newsletters, do you think that’s something that is here to stay? What do you, what do you think is different this time from, other particular waves we’ve seen in the past?Louis: [00:32:33] Wow. Big question. I think it’s, I think it’s interesting. I think people, so what I’ve seen is over the last couple of years that, I mean, info-product creators have always known that they need to own their own email list. I think. And people have always been blogging and there’s no, and yet it would be a good idea to be able to email people the same things that they don’t have to come and discover me every time and check if something’s going on.And then I think over the last couple of years, what I’ve seen is that people who are maybe more into like the, the nerdier kind of technical industries have kind of copied onto the same idea, right? So we’ve seen people moving from a tech journalism, into newsletters. We’ve seen. Podcasters realizing, Oh, wow.I should probably own this audience as well. people on certain platforms who’ve been kind of, especially, I think, you know, people with Facebook audiences, for example, who’ve seen, okay. Yes. I have this group with 70,000 people and, but tomorrow I may not be able to email or to reach even five of them.So they’ve kind of woke up to that threat and realized yeah. Any to, to own that audience in a way that really own the email. Makes it easy with the kind of content that you want to send them. And what I’m seeing at the moment, especially from like conversations with people who are, you know, talking to us at sparkly is that we’re getting a lot of interest from kind of younger and maybe slightly more or less, less, less closely related to the tech industry industries.So people coming from YouTube, people coming even from Tech-Talk from Instagram, all those people that you wouldn’t even necessarily think that they would have. A big email list, like, personal trainers who don’t, who do most of that on, on Instagram, for example, they are suddenly really aware that they need to start growing their email list.And, I think that’s kind of it. I definitely think it’s here to stay at least, you know, for the foreseeable future. I think it’s a really interesting time to be, to be an email for sure.Nathan: [00:34:37] Yeah, it’s really fun. But like no one in the last two years is or said like isn’t email dying, whereas before they did. And you’re like trying to explain, no, it’s not at all. You know, like we see, these. Trends and the numbers and it’s just, it’s crazy. But now it feels like the mainstream sort of, press in general sentiment is catching up where people are realizing that they should have this hub and spoke model where the email list is their hub and then the Tik TOK and YouTube and Twitter and et cetera, are all these spokes that drive backLouis: [00:35:10] Yeah, totally.Nathan: [00:35:13] Something else that. I’ve been wondering about your take on this? You and I are both fairly vocal on, on Twitter about, email lists, monetization methods. what’s been your take on paid newsletters and how have you seen those play out?Louis: [00:35:27] Oh, I so difficult. I think a lot of people are going to get done by paid newsletters. And I think I see a lot of people right now who have been really struggling to get a hundred subscribers and who, if they had tried to monetize in some other way, wouldn’t be making $500 a month, but we would be making closer to, you know, 5,000 or $10,000 a month.I mean, I was thinking about it with my own list of sales with founders. If that was a weekly list, an email where I would be just giving some sales tips each week or giving the same advice in a weekly format. I don’t think I would be at even $2,000 in monthly recurring revenue with that as a paid newsletter.But I mean, in the first year of doing it, I was in the six figures with it, with courses and with, with coaching. so I think, especially at the, I think. People, a lot of people have gotten into that too enthusiastically without maybe realizing that you are on a treadmill at a certain point and you have to then decide, okay, do I, you know, hire, do I make this more professional?Do I want to keep creating content or outsource the content creation to someone else for a long time? you know, like long-term to be able to grow it to something sustainable or do I want to add in different monetization streams? I think labs who. Maybe originally kind of started off with the idea of it being a paid newsletter, but realized actually it’s more of a paid community with other things going on there.And the newsletter again is really kind of just a way to get in that. I’ve seen other people like, like Dan from capital, he tried the, the paid newsletter and it didn’t quite go so well. And you realized consulting and services were for a much better shout. So. That’s one of the things I think also if I look at like substance, for example, that the challenge that they’re going to have is that it’s super difficult to layer other products and other services on top of that.And that’s going to become, I think, a real, a real blockade when people realize, Hey, for the same amount of work I could be making, you know, two, three, five times as much money quite easily.Nathan: [00:37:37] Basically the same point that I made on Twitter a while ago is, let’s say we’re trying to optimize for. Earning a hundred thousand dollars as a creator, as an independent creator online, I want to go from zero to a hundred thousand dollars in annual revenue. What’s the best path to do that. And if that’s our goal, I don’t think it’s paid newsletter.Now, if the goal is I want to have the simplest business model and I want to make sure that money just shows up really consistently, and I have a straight, a difficult, but straightforward life. Of showing up writing one to three articles a week, promoting them in this way and making sure that I get the same $2,005,000 a month, that just shows up like clockwork.And then a paid newsletter is fantastic for that because it’s going to be very predictable. You and I both know from product launches that you can have a bunch of like $500 weeks, and then you can have a $50,000 a week and then a bunch of. You know, and then it’ll taper off again and, well, that’s far more money, usually over the course of a period of time.It can be stressful, right. Especially if we wanted to hire employees and there was something like dealing with payroll when you have these spikes, but I’m totally with you when I see. I guess I’m of two minds on paid newsletters, one it’s incredible. And I love that the willingness to pay is there in the market.And it just, it added a whole new monetization method for creators where you can choose whatever you prefer. and then the other side I’m like that is a whole lot of work for not as much revenue as you could through a course or through coaching or through, you know, so many other other methods.Louis: [00:39:24] Yeah, totally. And, you know, I don’t think it’s necessarily either, or, and I think there are just kinds of newsletters that need to be like that. Right. So, Isaac, over at tangle, for example, He’s writing news. Like it needs to be up to date having an info product or a course or something to him. It wouldn’t really make sense.Whereas, you know, a paid newsletter in that case, because it’s a regular content that needs to be updated all the time. Then that’s an absolutely amazing way of, you know, of supporting him. Whereas there are other people who, you know, the founders want to come to me for example, and learn sales. Well, they don’t want to learn sales for three years.If they’re learning sales from me for three years, that means I’ve done a terrible job at teaching them not to do sales. Right. So I want them to sign up for my newsletter. I want them to stick around for a couple of months and then I want them to not need my newsletter anymore. And, you know, I think that, you know, you just have to kind of, there will be a good mix of business models depending on what your audience wants.And I think understanding what your audience wants is the most important thing.Nathan: [00:40:24] You see, in platforms of people choosing, you know, sub stack, review is just acquired yesterday by Twitter. so that’s exciting. New news. I guess in full disclosure, ConvertKit is a shareholder in SparkLoop, through an investment earlier this year. No, last year I keep forgetting it’s 20, 21. but what are you saying?Because SparkLoop integrates with a lot of different platforms, and takes over this platform, agnostic approach, which I think is fantastic. where are you seeing in why people are choosing each platform?Louis: [00:40:58] Yeah. It’s it’s so I think we honestly don’t see. I hope I don’t get told office. We don’t see that many people choosing review. I think, it’s just not, I think that will change now with Twitter. But up until now, it was kind of pricey. And they had like, you know, more limited features and maybe we’re focused more on, kind of the slightly larger media companies, when it comes to sub stack, I think the advantage, the reason people go for what are the advantages sub stack has that people go for them a lot is also kind of the downside for the creator that makes them move somewhere else, which is that it’s very strongly subset, grounded.You know, you’re on sub stack and sub stack considers. You as a subscriber to be a substance subscriber, what just a, a subscriber to a particular newsletter that happens to be using sub stack in the backgrounds. So again, it’s that they make it very, very easy to get in and to get started. And I think that’s a great thing.And I think, you know, having as many people as possible blogging and creating newsletters and sharing what they, what they know with people is, is absolutely amazing. But I also think that there comes a point quite quickly when you start to realize with a tool like that. I mean, there are new ones popping up every day.You do get to the point where you realize, well, if I could just send a welcome sequence, if I could just do this one thing, if I could just tack people here or give them this link or just. If I could just sell for this one specific thing, or even just change this one tiny thing, then without doing any extra work, I could be making twice as much money.And I know that kind of, you know, I can take this audience with me wherever I want to go. And I think that is the big reason that I’m seeing that you have a lot of people coming into sub stack and finding newsletters and being inspired by substance and things like that, but then quickly turning to other tools that give them that kind of, You know, give them the flexibility to actually own their audience and actually, you know, make money and give their audience what they want.Nathan: [00:43:04] Yeah, that makes sense. I mean, I think that’s why you’re seeing a lot of publications start really easily on sub stack and then graduate from sub stack over time. I mean, just, just last week, Mario moved the generalist often sub stack and over to convert kit and then. ConvertKit and Pico and, and, you know, collection of tools.And then, Dan and Nathan moved every off to their own custom built platform. And so I think you’re just going to see more of that as people come in and then grow and, and, and graduate out.Louis: [00:43:40] Yeah, I think it is, it is, it is graduating, right? That’s how people, it’s almost, it’s, it’s a consistent word that people use. They graduate from subsect to something else, which I think is a, it’s a really accurate way of putting it, but also maybe not the best thing for sub stack as a company that. That people graduate from them when people call it graduating.Nathan: [00:44:01] It’s not a dig on sub stack in particular because. Like when you graduate from high school, you’re not like, Oh, that was a terrible waste. Well, maybe it depends on your high school experience. Right. But, but you’re like, I learned all of this and now it has set me up for university. Right. And, and so it’s sort of that thing of when you get started, I think in writing a newsletter, there’s so much to do, and we see this with convert kit where you’ll get someone say who has 200 subscribers.And they’re like, let me launch a referral program. Let me, look at this crazy automation. I segment this so many different ways and they’re learning all of that. And you’re like, hi, quick point, you have one person that made it down. This like obscure branch of your automation. Like by the time you took 200 and, and branch all the way down, what you actually need, the habit you need to work on is writing consistently and publishing and promoting that content.And that’s what sub stack has done so well. And so it’s. It’s this initial training rounds. And then once you’re at the thousand 5,000, 10,000 subscribers, and you have the writing habit, then it’s like, okay, I’m here. Now I can graduate and use, you know, a tool like ConvertKit or something else that is going to have the sequences and segmentation.The challenge that we have is ConvertKit is building a tool that, that beginner can start on as well. cause I think sub stack has demonstrated that they can make the market so much bigger.Louis: [00:45:27] Yeah, totally. I love that. It’s like that analogy I just reminded me of, I didn’t know when you were a kid and playing sports, whether you you’d see those, like you’d always want like the best, you know, running shoes or like the best. And in my case, like the best like goggles or the best swimming, like, They’re like the best, like swimming trucks and stuff like that.And it’s always like, well, you don’t necessarily need to have like the perfect best equipment to get started. You just need to actually go and practice. You need to go and run. You need to go to play and you don’t need to spend $5,000 on a pair of shoes or something like that.Nathan: [00:46:02] I agree. as we start to wrap up, I’d love to hear. You know, we talked a newsletter referral programs quite a bit. but I’d love to hear some of your more general advice for someone who’s starting a newsletter and maybe growing from, I should start with getting any, any advice for someone looking to get those first hundred subscribers for their newsletter.Louis: [00:46:24] I don’t know. I think the first 100, I, I’m almost more of a fan of, I think you should be creating content probably in other places. And when you, before you start your newsletter, I think if you’re gonna start writing a newsletter about something in particular, Most often people who get to a hundred subscribers and carry on, they get there relatively quickly because they’ve been being useful in other places, for example, on Twitter, in forums.Maybe even, you know, physically in, in, in, in, in places like in a, in a company or somewhere like that, that may be less than them with COVID. So I think for those first 100. I, I almost think you should focus less on getting more subscribers through the door and more on things useful and creating content in other places by people can find it on getting the subscribers from there.I think people are very, they’re very afraid to go and share this amazing blog post or this amazing email that they’ve written. In different places to stick it, maybe on medium to tweet, thread it out, to put it on indie hackers, or how can you use, or some Reddit sub forum, something like that. I think people should be sharing it much more often than if people like it.Then they’re going to go and sign up to get more of that. They’re not going to say, well, I’ve read this now, so I don’t need to go and sign up. I think that’s something that I see a lot of people making a mistake with.Nathan: [00:47:43] Yeah, that makes sense. Yeah. And just building that habit of promoting and publishing consistently can start on something as easy as, as Twitter, you know, or whatever channel. So I think that’s great. Something else that I often encourage people to do is to do direct outreach and to say. Like go find, start with 10 people.You’ll reach out directly find, find 10 20, who might want to sign up. Even if that first group is just doing it, because they’re like, not that interested in your topic, but I like you as a person. And so I’ll support your thing. And that sort of gets that initial quick momentum.Louis: [00:48:20] Yeah. And you know, you can also piggyback off other people, right? Like, I mean, I only have only 3000 probably subscribers on Twitter, but if someone writes something about me or mention something that I’ve said in that newsletter alongside three or four other people that I would like to be mentioned alongside, and then they tell me that’s on Twitter.Well, I’m. Almost certainly going to retweet it and share it with people that I know. Right. And I think most other people are not too close to being as vain as I am. So I think you can, you can pretty easily piggyback of other people’s audiences to get those best hundred or 200 asNathan: [00:48:52] Yeah, that makes sense. It reminded me, I’ve been seeing more like newsletter collaborations, you know, that’s something that’s very common in the YouTube world. YouTube is direct advice to creators as you should. You should collaborate. Get, bring these two channels together. You’ll both get a bunch of subscribers release one video on each channel. Have you been seeing more newsletter collaborations and how well have they been working?Louis: [00:49:15] Yeah, we have, we actually, it’s something that people keep emailing me about when they sign up a spot group as well and saying, Hey, do you know anyone else who has a similar newsletter? and I think that that is a really interesting problem space that also hasn’t quite been solved yet. For some reason.I think partly because it’s very difficult for computers to work that out. But a recent one that I saw was it was again Trevor McKendrick and, and Josh Spector did it, a recent takeover that went really well, where they basically, they introduced each other in that weekly edition of that newsletter.And then set, this is going to be a takeover in effect. Josh is going to share some knowledge here. I think you’re really going to enjoy it. So, you know, putting your personal, what behind it, your personal trust to say, this is what I’m reading and listening to. And at the end, you can go and sign up here.So I think we are going to see a lot more of that. And I think we’re also going to see a lot more people is slightly different. I think we’re going to see a lot more people building the framework, the structure of that newsletter around the idea of share-ability. So something that James clear does a really good really well is.Each of his bits of his three, two, one newsletter. There is a very handy link to, to share it, tweet out that thought or to share that thought somewhat. But I think we’re going to see more people building that format in to make it super easy for their readers to, to share something that they found interesting.Nathan: [00:50:36] It’s interesting. I was a person who always underestimated the value of a, like a tweet button or something being there. We recently added it where after you create a landing page and convert it, it has, you know, a share on Twitter or Facebook button right there. That’s prominent. And there’s now like 50 shares a day.That show up just from that button, like just on Twitter, like, on Facebook, I think it’s actually double. And you’re looking at this and you’re like just coming from the explicit ask to share and promote makes a huge difference. So I can totally see that with James. And when he gets down to the quote or some thought, it’s like tweet this, I knew the person who originally would say like, no, if they want to tweet it, they’ll just highlight the text jumps at Twitter and do it. And the fact of the data is that that’s actually having the button and making it, having the call to action makes a huge difference.Louis: [00:51:35] Yeah, I think, I mean, I I’d be the first to admit I’m a super lazy person. if you give me a button and just say, Hey, you could go and do this, then I’m much more likely to do it, even though maybe I don’t think of myself as the kind of person who would be affected by that.Nathan: [00:51:48] that makes sense. Okay. So in the newsletter takeovers or the collaborations, I think the natural thing that I would have thought about is like, Hey, let’s do cross promotions, you know? If you’re enjoying my newsletter, you should also go check out the reason I really like these people you shared with Trevor of them.Basically they wrote the same content, right? Cause they’ve wrote their weekly newsletter and then they just, they just purely swapped. and so it was that same great value and it wasn’t an additional lift for them. They have visits. Someone had to do the newsletter matchmaking, right. knowing each other and that sort of thing.But I guess I also thought yesterday, Lenny rigidity, who’s been on the show before, did it with April Dunford or at least ran a guest post from April Dunford on, on pricing and strategy and positioning. And that’s such a big thing. I don’t think James talks about this a lot, but he did a ton of guest posts early in his career.That’s how he built his very first audience was. Going out and guest posting like crazy. So I think we’ll see a lot more of it.Louis: [00:53:01] Yeah, totally. No, I agree.Nathan: [00:53:03] Are there other things with SparkLoop that you’ve seen that people are doing, that it was working really well for newsletters or, or any, any final thoughts on. Like, as you put together your referral program, make sure to do these things.Louis: [00:53:18] I’m trying to think. So I think there are really two things we didn’t necessarily touch on too much. That might be interesting. so the one is just that the, obviously the ease of use of the referral section is a big thing. So having the actual referral link itself inside of the newsletter and having shareable, like one click to tweet on click to, to share on Facebook, for example, having those links in there as well, so that you don’t have people, you don’t make your subscribers go and click on a button and then.In to the referral programs that generate that referral link and then share from that, that tends to,Nathan: [00:53:53] is a refer. Is there has a referral for account by default, basically.Louis: [00:54:00] exactly. Yeah. I think that’s a big thing that some people that realize makes a massive difference and it’s often you see people who try out to referral program where there are so many steps involved to getting like for people even to begin sharing that they don’t get good results. And then they assume, you know, a referral program in general, it doesn’t work for me not, Oh, the specific way that I set this up was just super complicated for my subscribers. and then the other thing I would say that we’ve been sleeping on a bed at sparkly. We didn’t realize because no one else was doing this. Just, just how, how much potential is that is the idea of running referral giveaways.So of having like a time limited window where you basically say, okay, instead of. Let’s say getting this reward for three referrals, this rewards for five referrals and so on saying, okay, on a Monday, email goes out, make one referral this week and you’ll be entered into a giveaway, to win whatever it is.One of three of these, these things by Friday. So it adds in some urgency. And what we’re seeing as well is that a people respond super well to it because they think, okay, everyone can make one referral and I’m in with a chance to win this big thing. And B we’re seeing people using that either as a sponsorship opportunity.So saying, you know, reaching out to a sponsor and saying, Hey, can you give me. So the price for this and return to the exposure and also maybe pay for that as a, as an additional advertising slots, if you do advertising or even using it to reach out to, to potential sponsors, especially if you’re a bit smaller and to say, okay, look marketing team at this company. You know, we know it’s difficult for you to get the budgets, especially to work with us. Cause we’re smaller. Why don’t you just sponsor us? You know, why don’t you give us two or three of your products to run as a referral giveaway. We’ll mention you we’ll include a link and we can use that as a way to build up a relationship.And then let’s talk about you actually sponsoring us for money in a couple of months and that’s, that’s worked super well so far.Nathan: [00:55:58] Yeah, a lot of sense. I mean, thinking back to the early days of convert kit, when you know, you’re doing, we would do content marketing, right. To try to get customers, but there’s, there was no incentive to sign up. Right. Then it’s like, Oh yeah, I can work it. Now I’ll switch to that sometime this year, this decade, you know, and there, there’s no reason to do it right then.And that’s when we started webinars where you would have some time limited thing, and you’re like, look, if you sign up for ConvertKit on this webinar, then we’re going to give you this discount or these additional bonuses or something else. And it takes this thing that someone is intending to do at some point.And they go to like, great, I’m going to do actually do it right now. And that makes a huge difference. And then, you know, for those that don’t sign up in the webinar, you add another timeline of like, if you do it by the end of the week or, Know tomorrow or something like that. And you’re basically looking for any opportunity to take something of like, I want to do this and we’ll do it someday.And you’re just saying great, anytime you want so long as it is before Friday, and that’s going to make a big difference. It turns out urgency matters. So I love that.Well, good stuff. we should start to wrap up. I’d love to hear you may, if you just want to let people know one where to go sign up for SparkLoop, if they’re considering starting a newsletter, actually, if you have a getting started guide or sort of that it needs any content, around, knowing if a newsletter for our program is right for them, that would be good.And then where people should follow you on other platforms.Louis: [00:57:32] Yes. So I am @louisnicholls_ on Twitter. louis@sparkloop.app is a great place to reach me. If you have any questions, sparkloop.app is the website that SparkLoop. But the best place to go. And maybe this can be included in the, in the show. Notes is actually sparkloop.app/referral-university.And that’s a free, five email course that we’ve put together. That includes a free month of SparkLoop where you can get, sorry. My video seems to have gone for some reason. Don’t worry. It’s not an important part. yeah, basically if you, if you go over that, you can get. A, a Fremont and sparkly and also a series of five lessons where we will walk you through what a referral program might do.See you, whether it’s the right time, how to set one up, what rewards to use and that kind of thing.Nathan: [00:58:24] Sounds good. That’s perfect. Well, I’m a big fan of SparkLoop, obviously, because. I invested in SparkLoop and we’ve been promoting it. And as part of creative pros, if you’re using ConvertKit and you’re on the creator pro account, you get it for free. so definitely take your newsletter, start a referral program, and you’re going to see pretty significant growth if you’ve set it up correctly with a bunch of tips that, that living food itself, Louis.Thanks so much for joining me today.Louis: [00:58:49] Yeah, Nathan. Thanks for having me. It’s been great.

Dan Frommer runs a popular newsletter called The New Consumer, which discusses topics on technology and consumer brands. Beginning his career at Forbes, Dan has a long history in the technology field. His extensive experience includes Editor in Chief at Recode, Vox Media’s tech and business news publication, and technology editor at Quartz. He also spent years building up Business Insider as its second employee. In this episode, Dan discusses how email is the most effective way to reach influential people, explaining how he leverages his newsletter, The New Consumer, in a way that will capture the attention of CEOs, board members, and investors.Dan shares newsletter insights, including: Important questions to ask yourself about newsletter tools. Avoiding the optimization trap. How he creates a quality experience for his readers. Links and Resources Forbes Recode Vox Quartz Business Insider Stratechery Hodinkee Benedict Evans Dan Frommer Links Dan’s Newsletter: The New Consumer Dan’s Website: FromeDome Dan’s Other Website: Points Party Twitter: @fromedome Episode Transcript:Nathan: [00:00:00] In this episode I talk to Dan Frommer. He runs a popular newsletter called The New Consumer. He’s had a long career in tech, tech journalism, he started at Forbes and then he was at Quartz and Recode and was basically employee number two at Business Insider, and worked to build that whole business for a long time.And he’s always had this one-man-band sort of style, which really resonates with me. That’s basically where you learn to, design code, you know, put together plugins, build out your site, as well as writing and publishing and being a journalist and all this other stuff. So he’s done something really impressive and going from the editor in chief of Recode, which is a publication owned by Vox, which is quite large and popular, to running The New Consumer, which he’s had for two years now.It’s more than paying his bills. He’s earning a full-time living from it and he gets to control his own destiny. I love it. We dive into all kinds of interesting topics. We talked about why he has only an annual subscription, rather than going for just monthly, like most people do with paid newsletter, his tech stack, what he thinks about free versus paid subscribers and so much more. Let’s dive in.Dan, Welcome to the show.Dan: [00:05:00] Thanks for having me.Nathan: [00:05:02] So I want to go back a little bit, as we talked about in the intro, you’ve got all kinds of history and journalism and everything else. Now you’re running your own newsletter, so when you got into journalism, where did you think that that career would end?What was the pinnacle? You know, like, as we go through the, the years, like. Was it ending with editor and chief of, of Recode? Like how far ahead did you, did you think? And,sand what did success look like when you were just starting out?Dan: [00:05:31] Yeah. I’m from Chicago originally. I, you know, my background is both in, creating websites, web design. I started doing web design and, and building websites when I was in middle school, in the nineties, and then I went to journalism school at Medill at Northwestern. So my background and my interests have always kind of been at the intersection of.Journalism like real ethical. proper journalism, but also creating new things on the internet. So new media brands and building websites, building audiences, and I’ve always kind of, I guess, optimize my career for both of those things. so that’s, that’s one way to say, like, I never really sat back and was like, Oh man, I really need to work at the New York times or the wall street journal or something like that. snothing against those places. It’d be cool to perhaps, you know, contribute there one day or something like that. But there wasn’t some bucket list where I was like, I must work for. A big network or a big newspaper or something like that. I, you know, I actually started my career interning at,sthe public radio station in Chicago WBZ.And I really did a lot of,syou know, I trained to be a broadcaster. I was really interested in broadcasting, but,swhen I moved to New York to start my professional career, it was clear that. All the jobs were in what was called digital or interactive journalism. And also that’s where my skills were really helpful. sit, it actually was useful that I knew how to edit pictures and build webpages and. you know, and do video work because most, most of my peers were not trained to and, and thought that that wasn’t really part of their job. So,snot only was able to do that, but I really enjoyed it and I still do now.So, you know, thinking, thinking back now, 15 years ago, there was never a point where I was like, Oh man, I really need to get a big title at a big magazine or at the New York times or something like that. I didn’t probably know. Right then, you know, my first job was, was at Forbes, which was kind of, but the, the forbes.com.So it was like the interactive,ssubsidiary of Forbes magazine. So I got to see that kind of big brand. Big media world, but,salso be kind of on a scrappier side of things. And, and from there it just kind of became like, you know what, what’s something interesting that I could work on. that, that took advantage of both my interest in storytelling and journalism, but also,sadvantage of the, of the tools of technology.Nathan: [00:08:07] Yeah, that makes a lot of sense. And I have a similar background of, you know, starting in high school of figuring out HTML and grabbing books in the library and trying to, trying to piece it all together. And that served me a lot. Do you think that,slike journalists today or anyone getting into. Writing or building an audience.Do you think that pursuing those skills of video and code and, and maybe some simple design is worthwhile and worth the effort, you know, in addition to figuring out and learning how to be a good writer.Dan: [00:08:36] It’s certainly helped me a lot. You know, I hate to prescribe something to someone because you can do great stuff without any of it. but it really helped me a lot. I, you know, I, I really love being a one man band, which is, it is a term that was used a lot in like broadcast media, where you would have to, you know, hold the big camera over your shoulder and shoot and edit and do that kind of stuff.[00:09:00]sI never had one of those jobs. Those were some of my peers starting off in, you know, small town, local,sbroadcast,steams where you had to do that because there were no resources. I, I love being kind of a one man band on the internet though. Creating my own website, doing my own writing and reporting,syou know, editing my own work, producing it, publishing it, promoting it, all those things.Those are skills that I developed in newsrooms. So, you know, I was lucky to be able to work in some really great newsrooms where I learned a lot of those skills. What I would say is kind of, if you’re interested in visuals, if you’re interested in multimedia, Do learn those skills, whether it’s, you know, in a job or at nighttime,syou know, in your spare time, on, on nights and weekends or in a course or something like that,sthose are, those can be hugely valuable skills.If those are, if that’s the kind of work that you want to produce and publish.Nathan: [00:09:56] Yeah that makes sense So as you’re going through, [00:10:00]syour career, when did, when did newsletters come onto your radar as something that you wanted to pursue?Dan: [00:10:07] It’s interesting, you know, newsletters of course have been around for the duration of the internet or at least the duration of email. One of my absolute favorite newsletters started off probably in the early 2000s It was the DWR design notes newsletter from, from the founder of design within reach. sit was kind of the first editorial newsletter that I remember really loving. And then, you know, when we were starting Silicon alley insider in 2007, we were writing about DailyCandy and Thrillist as kind of an exciting model. that, that, you know, money was, was flocking to, and then of course,syou know, there’s the new newsletter, boom.And, you know, I don’t think there was ever a point even now where I was like, Oh man, I really, I really want to be doing newsletters, but it really is a useful and elegant format for two reasons. One is that. everybody checks their email. You know, this is, this is,sprobably a known cliche to say, but it’s true.Like the most important people in the world, unless they have four levels of assistant,sare still reading their email. And so is everybody else So it’s a really great way to, to reach the most influential people who, you know, are truthfully like not really on Twitter and if they were in the past, they’re probably on it less than they were before.They’re not really on LinkedIn. They’re not really on Facebook, but they’re really on their email. So it’s a great way to reach important people. And that is kind of the foundation of my publication in the new consumer. I’m writing for the people who are running these companies, the CEOs, the board members, the investors, those people still read email.The other reason I love email and kind of picked it and settled into it is that it’s a, it’s a place to be really conversational and personal in your writing. You know, you’re. If you think about the context of email. You’re kind of bunched in between perhaps other email newsletters and,syou know, invoices and receipts and that kind of stuff.But you’re also sandwiched between personal notes and professional notes from people. So if you’re trying to be an individual with a voice. Email is actually a place where that works. you can, you know, it’s, it’s not all about the first person writing about me, me, me, me, me, but it does let you be more conversational, have a little more of a tone to your writing.That doesn’t really work. If you’re, you know, writing a news article for a Newswire like Bloomberg or Reuters, or even someplace like the New York times where. They’ve certainly allowed people to have more of a voice recently than they had in the past, but it still is kind of an institutional voice and not really yours.Nathan: [00:12:48] Yeah, that makes sense. So what did it look like when you’re, you’re at Recode and you’re looking to, what was the conversation that you’re having as you’re looking to start the new consumer?swhat, what things were you looking for as to like, is this a good idea?sand actually making the switch, what was on your mind?Dan: [00:13:06] Yeah, I’ve been thinking about it for many years, even before I started it at Fox in, at Recode. I so my, my first job was@forbes.com. My second job was starting business insider. I was the second employee there. It was called Silicon alley insider. When we started in 2007, the idea was. We were going to be kind of an East coast tech crunch covering the New York startup scene. sI lived in New York for the last 15 years until moving to California this year. We are. And,sand that’s where I really firsthand caught the, the startup bug actually worked for a startup college. So I knew that they were fun,seven before that, but, you know, being able to start. Alley insider with three of us at a, at a desk, essentially in the, in the back loading dock of another startup.And then four years later have over a hundred people working at the company. It showed me that there’s a lot of room for entrepreneurship and innovation in digital media. So. I left there after four years and started my own publication back then. I’d also been really heavily influenced by a guy named John Gruber who doesn’t really do an email newsletter, but he is a solo indie publisher,swho has, you know, made a great career from his site, daring fireball, which mostly writes about the world through the lens of Apple. sand then Jason cocky and some other of the Indy. Publishers, you know, back then, bloggers, I guess you would call them. So I started a site in 2011 called splat F, which was going to be my kind of. Indie news tech analysis blog also kind of through the lens of Apple and similar companies. I wrote a lot about Netflix and the early streaming business Quickster was one of my first stories there. sand it did really well. I got like a quarter million readers my first month or something like that, which is a lot for a new site. and I was, but I was monetizing through ads, which just doesn’t work super well for niche media. there were some really great ad networks back then that were designed for niche publications, but wasn’t really a successful business doing that. sat least by that time, 2011. Things were kind of starting to dry up in the ad world where programmatic was starting. You really needed scale. That video ads were a big thing. Worked really well for big, big mass sites like the verge or, you know, New York times or, or Yahoo or something like that. It didn’t really work super well for a niche site.So I did that site for, for a few years. you know, I had a really. Nice deal with an ad network where they were paying me a good guaranteed rate, but probably weren’t selling that many ads. So it wasn’t really a sustainable thing. I didn’t want to sell my own sponsorships. That’s a whole other job. so, you know, while I had a great time publishing that side, I ended up and then I ended up doing another startup,swhich was entirely different. sbut then ended up going back to work for, you know, established media companies. Quartz was, was my next job,swhich was kind of a startup at the time within the Atlantic group. And then I went over to Vox media, which by that time was a pretty big startup. I think I was probably over employee 1000 at that point.So,seven though it was still felt like a startup,sit wasn’t always, so anyway, so had been thinking this whole time, like, all right, well, what’s my next thing. There were a lot of, a lot of startups and kind of indie publications that I really admired. And they weren’t really monetizing through ads.One of them was Hodinkee, which is a, a site about,smechanical watches and kind of viewing the world of, of luxury through, through really fine watch craftsmanship. They were making money through product sales and through e-commerce, which was super interesting. my wife works for a publication called the business of fashion, which was started in London and they were one of the pioneers in paid subscriptions for professionals, you know, costing several hundred dollars a year.That was something that I was aware of and thought was interesting. And then of course, you know, the, the real big influence was Ben Thompson and Stratec Curry, which really smartly used the newsletter as a function of a paywall. you know, there’s always been a, a website component to Stratec Curry, but.He was able to use the email, the access to the email newsletter and the fact that it was pushed. And the fact that it was really gated by the fact that people don’t share email accounts to set up individual subscriptions charge what at the time seemed like a lot of money, a hundred dollars. Although we know that as actually.And then an incredibly great value. If you read Stratec Curry and work in the tech industry, you’re getting thousands and thousands of dollars a year worth of educational value from a hundred dollars subscription, which he has since increased, modestly the price. but that’s when I started seeing email as, as a tool that could help me a run that indie publication that I always wanted to run and be okay. suse the subscription and membership functions as kind of a gating mechanism. And that’s where email, in addition to being able to access everybody that I wanted to access and have that kind of personal voice too. It was a really great paywall function. And that’s kind of how I landed in the world of email.Nathan: [00:18:28] Yeah. I mean, you’re absolutely right. That like newsletters are great for the personalized it feeling like you can. I mean, I’m just thinking about the different editorial voices that each publication will have and, and writing your own newsletter. You can define exactly like this is the voice that I want to have.This is the way that I want to interact with my readers. And even,sat least for me, I like, I love the replies to the email. Is that something that, that you’ve pushed with your audience of asking people to reply and share feedback or,sis it more, you know, just the one to many side.Dan: [00:19:03] you know, not as much as I should. I do get a lot of replies. They’re very thoughtful. occasionally I’ll ask someone like, Hey, should I post, you know, do you want me to publish this? And sometimes they’re like, nah, not really. You know, I didn’t really, I didn’t really edit it or write it in a super eloquent way.So I’m still working on that. It’s interesting. Like one of the things that definitely is different than I thought it would be is the format of my newsletter. You know, I, I,syou know, I, I grew up reading a lot of magazines. I love the idea of the way that magazines are formatted. I also read a lot of like newspaper columns when I was a kid.I always thought that I would have a newsletter that had a lot of modules to it, like an introduction. And like maybe some, some short pithy takes somewhere either at the beginning or at the end, and then maybe a longer piece. And then maybe some other things that were like, Not even texts, like they were either a graphic or a chart or something like that.Anyway, that this is all to say. I did not imagine that my newsletter format would be a 1500 word essay most of the time, but that’s kind of what it’s turned into. And I mean, it’s working,speople like them they’re I think, valuable and useful. They let me get the depth that I want, which is super important to me. sI’m not, I cannot ever write shallow stuff that everybody else publishes. I just would go out of business. there’s so much commodity facts and data out there. I could never compete with Bloomberg on the level of like just aggregating facts quickly. So I don’t want to, I want to have depth and analysis and a point of view. sand it’s turned out that like, The, the format that really works for me for that is like a 1300 to 1800 word essay. but I still do want to get back to this idea of like other, other formats, other modules replies are certainly a version of that. [00:21:00]syou know, I’ve been very fortunate to build a sizeable community of readers and.They’re really smart people who work in the field that I write about. So I’m very flattered and lucky in that sense, and then figuring out how to get their thoughts into the newsletter. you know, beyond just like interviewing them and writing stories about what they do, which I do do,sfiguring out how to get more of that kind of conversational element into it is something that I’m working on for this year.Nathan: [00:21:27] Yeah that’s, that’s super interesting of just what you thought your expectations would be going in. then what it turned out to be like. I see a lot of people writing newsletters. Yeah. And maybe someone like Tim Ferriss, right. With the five bullet Friday where it’s these quick little hits and, and you see that.But honestly, the newsletters that I see doing the best are the ones that are taking the approach that you have of like longer form, original thinking from a unique perspective. and so I’m trying to think if, if there’s very many people that have built an audience through the short form quick,sLike the, the board and newsletters, the highlights.Does anyone come to mind?Dan: [00:22:08] I mean one that I love is Benedict Devin’s, who has had an interesting career. He started off as a, as a, I believe a, an equity analyst covering telco stocks,sthen became a venture capitalist at Andreessen Horowitz and has now gone independent with a subscription newsletter. He has a really fantastic kind of bulleted newsletter with, I believe, well, over a hundred thousand subscribers, Nathan: [00:22:35] Yeah Dan: [00:22:35] like 300,000 Nathan: [00:22:36] side of Dan: [00:22:37] Something like that. Yeah. and the reason he does so well, I think is not just because he does a good job curating the bullet points, but he has a very, very good way of having a succinct take on things that is both educational and also kind of makes you think a little bit and doing that in a way that is not patronizing.Or cynical. there were a lot of like angry takes on tech and. While entertaining. I don’t find those tremendously useful for anything. perhaps they’re useful at, at, you know, getting people mad on Twitter or something like that. But I think Benedict Evans knows the right stories to pick. And then also seems to have just a really smart take on a lot of things.He has also since,syou know, and, and he was blogging in the background. So he w he was writing those longer pieces as well. That has kind of become the hybrid model of his newsletter. Which I, you know, and love and, and happily pay for. there’s others, you know, there’s a really great one in the e-commerce industry called 2PMswritten by a guy named Webb Smith who has built a, you know, he’s built it.More,ssophisticated business than just newsletters. He has a forum and that kind of stuff. He’s a great curator. There’s another one called lean Luxe which is a really great curated list of links. they’re out there, but certainly the, you know, when I think of what I’m trying to do, it’s kind of a hybrid between journalism and analysis and.Format-wise I actually take some inspiration from wall street research or, you know, corporate research. I read a lot of stock analysts notes and research reports from places like McKinsey and BCG and those types of places. And. You know, I would never call what I’m writing a white paper. I don’t understand why people are attached to that format or concept. sI download a lot of those. I never really finish reading them. but I, you know, I, I try not to, I try to intersperse my text with,scharts and other visuals and try to create kind of a, you know, an, an experience that’s both educational, but also. Maybe not entertaining, but kind of entertaining, like fun to read and to experienceNathan: [00:24:59] Yeah, that makes sense. you know, one thing on the, on the numbers and everything from your newsletter, you should, we were talking before that, you know, you’re earning a, full-time living from. from the newsletter, a question that I had going in is you have exclusively a paid newsletter. A lot of people have this hybrid model, right.I have a free version and you know, and then the paid version you’ve gone all in on paid. Can you talk about,swhy you went on unpaid and, and then, you know, why isn’t there a free or a freemium model to that, to your newsletter?Dan: [00:25:32] sthe answer is that time,sis, is one thing. So the truth is actually there are some free articles,sand I, I started off kind of envisioning one free article for every two paid articles. It’s just that I, I, you know, for various reasons, like the thinking from I started writing the new consumer, my wife and I moved to Paris for four months.So there was just, you know, Paris was kind of the reason why I wasn’t writing that third post every week. there are other, other, other reasons since then,sI do try to, you know, I aspire to have more free content. I think that is certainly a way that people find out about you. There’s no doubt that articles that are free reach, you know, at an exponentially larger audience than ones that are paid.I publish probably a free article every month or two. My goal is to get that to about. Once a month or twice a month. one thing I just did that was free. However, is this is this massive project that I launched in December called consumer trends, which was a collaboration with a venture capital firm in New York called coefficient.And what we did is basically 102 slide deck of the biggest trends that we thought were going to matter. Looking forward that, you know, the Corona virus had had this. Phenomenal impact on, you know, basically all of life, but especially the industries that we focus on, consumer packaged goods, food and beverage,syou know, things that people consume.And so instead of writing a, although there is a 4,000 word version of it, which was basically my script for the video version,swhich I’ll also publish for free. Pretty soon, there there’s a hundred, there’s 102 slides and. And what I did was published that document for free. the video is free that the script will be published for free for folks who don’t want to flip through the slides.And then what I’m doing for subscribers is kind of deeper dives on some of the topics. So that’s where I’ll do the, you know, 1500 word essay about what was four slides in the deck becomes a whole topic for, for deeper discussion and analysis. With the membership. So that’s,syou know, in terms of how much time it took to produce that, it definitely kind of equals the equivalent of if, if I had been publishing free articles every week or two on the site,sit just happened to be published in one huge.Peace at the end of the year. you know, my plan kind of going forward is to do more big, huge projects like that, which I think really make, make up for the time and the value that they create. And then also do some more free stuff over time. And maybe even open up one thing I’ve done is open up some stories from the archives that I felt.Maybe didn’t get the attention that they deserved. I did an interview with a co-founder of a beloved chain, chain of Indian restaurants in London called and I published it. I think March 17th or something like that, like right. As everyone went into panic about lockdown. So that piece kind of didn’t get the attention.I thought it deserved at the time. So I opened it up for free and I’ve been promoting it since then. and it’s reached a lot more people than it would have had it been paid. you know, another very obvious thing I need to do is kind of tweaked my homepage of my website a little so that when people are landing on it, And learning about the value proposition of my paid services.They’re also seeing, Oh, here are some free articles,sthat kind of give a sense of, of the, the point of view, the voice, the topics, the analysis, and hopefully those add up to, you know, a better, a better paid service. And also,syou know, being able to reach folks who are perhaps students or something like that.And can’t, or shouldn’t be paying $200 a year for my paid subscription.Nathan: [00:29:34] incase Right And I think you correctly pointed out that you don’t want it to be the reason that I thought that you didn’t have free like Oh I favorited or retweeted your announcement tweet your earliest, not prominently on your website And so it really everything guides you from the friends and supporters it’s like pay $200 and like actually support I have lots of questions about thatsone is,sfirst, what effect do you think that has had on conversion rates? Because I imagine it only having a paid option you then you’re free you know, your traffic to immediate,spaid conversion, paid subscriber is going to be higher because that’s The primary offering volume is that a factor in why you have it set Yeah we’ll go with Dan: [00:30:15] email Nathan: [00:30:16] volume by theDan: [00:30:17] when I launched, which was almost two years ago, it was a conscious decision. You know, I knew I would get a lot of attention by launching. It was still. you know, relatively early in the era of paid newsletters,syou know, I was fortunate to,sbuilt up a following on Twitter and kind of throughout the tech industry during my career.So I knew that my launch would get attention. I knew that I also needed to generate paid memberships in order to do this as a full-time job. And so, so I kinda didn’t, I don’t know, I didn’t, I don’t want to overthink all these things, but. I didn’t want to give people an easy out like, Oh, I’ll just sign up for the free plan.And, you know, we’ll see if it’s worth paying for, I really wanted to kind of give people a strong incentive to become, you know, early, you know, effectively angel investors by,swithout getting any equity, of course, by signing up by putting down their 200 bucks,sit was only annual subscriptions at that point.And I’ve since experimented with a couple other options I did later at a, a free. Tier of,sof newsletter that I’ve. Underutilized,sone of the things that’s kind of a challenge is that member full doesn’t make it easy to just plop your email in and sign up. Member full is the tool I use for managing my membership. syou know, I’ve kind of talked to them about it. They’re there. Drawbacks to that as well. they, they use a JavaScript pop-up I don’t promote the free newsletter anywhere though. Really accept kind of as the option of last resort on the Nathan: [00:31:54] producing Dan: [00:31:55] page where I describe all the, all the newsletter subscription offerings, however, that big trends report I launched new consumer.com/trends.You will see that one of the in fact, the first option that is being displayed is if you want to access this for free. Just sign up for a free account. You don’t have to pay anything to read all of this. And that’s where, you know, over the last month, thousands of people have signed up to read to read this free product.Now I all of a sudden have a list that’s big enough that I should actually be doing something with it. So one of my big projects for this year is figuring out, okay, what is something that I can offer to those free members on a reliable cadence that is. Worth receiving,swhether it’s,san entire free article or summaries of some of the paid are paid work, I did,sor something else, something completely different.Maybe that also goes to the paid members. Maybe that’s my Friday five thoughts or whatever it is. I have to think of. something that is useful and that I actually want to produce, and then I can send it to perhaps both of those lists and eventually drive more of those free members into paid memberships. sbut that’s kind of, one of the big plans for this year is figuring that out.Nathan: [00:33:12] Yeah, I like it. Well, there’s a lot of things,sthat I want to highlight in that first. There’s something that happens. Like if you, as you build this reputation and friends in the industry and everything like that, and you venture out on your own, you do this new thing, which so many people are either have done or thinking about doing then what happens is you got all these people who are like, Oh yeah, I want to support Dan.And so what does supporting. Dan look like in this case. Right. And I think you correctly pointed out that you don’t want it to be subscribe to the free newsletter or Oh, I favorited or retweeted your announcement tweet. Like, no, I want, you know, from, from the friends and supporters, to pay $200 and like actually support this new venture.And so by giving that as the only option. I think that works really well. I think just from a psychology perspective,swe’ve seen that, well, a couple of things, one, you see that on Kickstarters where, when people come out with Kickstarter, if there’s whatever that cheapest option is,sum, often people would just go for that.And so you see average order volume, or I don’t even know what you’d say. Yeah, we’ll go with order volume, go up just by the fact that they make their cheapest option, like $30 instead of $5, you know, or, or that kind of thing. And then another thing from that is, like I mentioned, you’re going to have a higher conversion rate to the site because that is the, the primary call to action. sand so I think that’s great. And as you also pointed out the, the annual subscription, right, it’s going to have lower churn. There’s more of an investment. People are saying like, okay, I’m going to try out your publication for a long period of time. so I think all of that is good. Now looking through your site.I’m I totally agree. I like, I think now that you’re established, you should have more of that free option. And actually one thing that I would do is take those like greatest hits articles that you have of, you know, maybe the five that you’ve made free over time that you really want people to read and bundle that we could tweak and optimize the site it out, like try it out for free.Get these five articlessand those automatically go out once per And that is a good way to perfectionism as a creator is a good way to not get anything done and so now that you not make any progresssbut yeah and on the on the testing side of things coming from like the software world where the big free report.Right That’s accessible. That’s a PR worthy that’s worth spreading around like there’s clearly a lot Yeah The effort that goes into it that’s such a good to my site It’s still not enough like traffic and new signups to really like do many statistically I think that approach of you know always having great content behind the paywall, over this as an the last two years doesn’t apply to you because the We’ve seen You know you’re like I would have to run this test crazy What are your thoughts for it to be statistically significant where I shouldDan: [00:36:08] Yeah, I guess one of the, that to me, one of the most interesting things about this kind of line of work or career or whatever you want to call it is the fact that small decisions like that matter. one of the parts of it that. Kind of, I don’t want to say aggravates me, but it’s challenging. It’s like, it’s hard to do too many tests.Like you can’t really, yes. You can do AB tests on like subject lines and that kind of stuff, but it’s hard to really test things like that. Like I can’t go back in and launch a second time, this time with a free option and see, Oh, did I get, you know, 50,000 free sign-ups because I launched and therefore my conversion rate.You know, even if it’s like one or two or 5% from that leads to a stronger outcome at the end of the first year, like it’s so easy just to overthink those things. And to me, like those are yeah. Interesting academic questions and,syou know, I hope that the answer is never like, Oh man, you missed out on a 10 times bigger business. sbecause of anything like that, like, you know, as, as, as I’ve heard on previous versions of this show, like. You really just have to create great stuff on a reliable basis. And, you know, as I always say, like my, my, the secret to success in media is be interesting every day forever. And, and that has nothing to do with, you know, how you position the signup buttons, or whether you charge one 99 or $200 or anything like that.It’s just like, can you maintain a level of, of quality and,sYou know, and, and be essential to people over a long period of time, then you’re going to be fine, no matter what, at least I hope so. And, and so far it’s, it’s worked out. So,syou know, I, I think about things like, Oh, what if I, what if I did this gimmick that’s free?Or what are I, what if I try this other thing over here, or do I need a drip campaign or all these things? It’s like, yeah. And you do, you know, for, for many months, actually, probably over a year, I didn’t even have a free. sorry if I didn’t even have a, an automatic welcome email going out to people, which is idiotic.I know that’s the first thing I should have set up. And now I do, and people like it and it’s giving them, you know, access to some of my best work, either the free folks or the paid folks. And, and now you’re right. Like what, what other campaigns can I set up that maybe re-introduce people to viable work from the library and the archive that. syou know, they, they would not have seen otherwise. And that’s, again, another kind of another project for this year is figuring out how do I surface my archives better? And how do I take advantage of the fact that I now have, you know, probably over 200 articles that members can read and probably a dozen or, or more articles that,sthat visitors can read for free when they’re coming to my site.So that’s kind of a project for the first half of the year.Nathan: [00:39:11] nice. Well, another good point of that is. One just start. Right? Cause we could, we could tweak and optimize the site forever and you’d be like, Oh, I only get to launch one time. And so I need to make sure that it’s perfect. And that is a good way to perfectionism as a creator is a good way to not get anything done and you know, not make any progress. sbut yeah, and on the, on the testing side of things coming from like the software world where I spend all my time now, Like we have all this traffic and we can run all these AB tests, but like, even on my blog, I’ve got about 25,000 email subscribers to my site. It’s still not enough, like traffic and new signups to really like do many statistically significant tests.So a lot of times when you read about AB testing or these other things, it’s like look as an individual creator It doesn’t apply to you because the math doesn’t You know, you’re like I would have to run this test for nine months for it to be statistically significant where I should actually trust the results And so I think you’re spot on that. A lot of that stuff is great to read but it doesn’t really applyDan: [00:40:19] Yeah. I mean, even, even when I was,syou know, at, at Fox media, we were, you know, we were fortunate to have. Tens or hundreds of thousands of subscribers to our our Recode newsletter. And we would do these AB test subjects. And the open rate would, would maybe vary by, you know, less than a percentage point. And at that point it’s like, all right, just go with your gut.Like, what’s the, what’s the best subject line. and don’t overthink too many things.Nathan: [00:40:47] yep. That makes sense. one other thing that I want to talk about is pricing. And so you have,syou know, the, the price of $200 a year. Is that the price that you started with.Dan: [00:40:58] surprise. I started with pricing is a huge question. you know, I had folks giving me advice to charge more than that, like a thousand bucks a year. at that point, Ben Thompson was at a hundred. There were a few other paid newsletters run by kind of friends or acquaintances that were in the hundred dollars to $300 range. sI had, you know, I knew that business fashion was charging two, 300, $400 a year for their professional membership. I also knew that investor newsletters were charging many thousand dollars a year for their membership. So,sto me, I, I thought about kind of what, what feels right. you know what, what’s an amount that I feel appropriately values my work, but isn’t kind of.Like a jerky amount to charge. And I Nathan: [00:41:48] math Dan: [00:41:49] to 200, it just felt like the right number, the way I kind of backed into it was, you know, w what would,swhat would it cost to have a nice business? Lunch was just the two of us in New York city. If we went out for sushi or something like that. Not 200 bucks. So, you know, if this is the equivalent of my member,smy subscriber taking us out to lunch once a year in exchange for my brain, 50, 50 weeks out of the year,sI think that’s a pretty fair value exchange.I anticipate most people are expensing it or otherwise justifying it as a business expense or as a professional membership or as educational media. So. I feel comfortable with that. I did some experiments with monthly and,sand now I have quarterly memberships, monthly, monthly. It was fine. I didn’t love it. sI want people to feel like they’re investing in me for more than a month. you know, there weren’t a lot of people who would sign up for a month and then quickly turn off auto renew and. You know, gobble up everything and then disappear. That wasn’t really a huge problem. I haven’t really studied churn in depth, you know, there’s just so many variables. sit’s at a level I’m fine with, so I’m not, not paying too much attention to it. obviously I want to be, I want it to go down and I want it to provide more value to, to readers, but it’s not like a huge problem. but, but I switched to quarterly as kind of an introductory point. Cause I figure, you know, three months in right.If people aren’t loving it, like they shouldn’t have to pay for it and read it. and if they are, that gives them kind of an entry point where they’ve seen enough of my work, you know, I, I kind of think as every issue, as an experiment in like topic tone, length format, structure, point of view, all of these things.And over three months you get enough. You know, enough iterations Nathan: [00:43:44] traffic and we Dan: [00:43:44] that to, to get a sense of like, this is either something you want in your life or you don’t, and then you can either kind of upgrade to an annual membership and pay less on a monthly basis, or just keep cranking with quarterly. And I think that’s a pretty good amount of time for people to get it.Good sense.Nathan: [00:44:01] Yeah, that makes sense. So over this time, like the last two years, since you launched a new consumer, We’ve seen like sub stack rise, like crazy. What are your thoughts on building, you know, on an independent platform? You know, you’ve got member full MailChimp plus Stripe, Yeah So since you’ve been writing about tech for a long timesI’d love your take on sub stack versus mediaDan: [00:44:22] yeah, not truly independent. CausesI didn’t write my own payment processor language. Right. you know, you’re, you’re in any line, you’re always kind of relying on suppliers. I, you know, for meThis whole thing, the only reason I do this and the entire reason I do this is because I want control. I want to control over my time, primarily. I want control over what I think about and what I do. And I want control over the experience for the member and the reader. And, you know, I want them to have a clutter-free reading experience without any intrusive ads. I don’t want them to ever have to click off of a pop-up. all these things are really, really important to me, to the degree where I’m willing to risk my career and my life to operate my business this way.So,stools are extremely important to me. hopefully they also play a role in that user experience and therefore, you know, I thought substantial. W was fine. if it was the only option I had, I would’ve probably been happy using it. I might use it for another project. I have that,sI’m currently paying MailChimp way too much money for,sfor a free newsletter that I, that I am not even sending out.So. Yeah, that’s point’s party, which was kind of my first experiment when I was still working at Vox media, I was like, what’s it like to make a newsletter? Huh? Why don’t I spin up a friend’s newsletter about credit card points and see how I like writing newsletters. and I learned very quickly, wow.Newsletters are a lot of work. and also it’s very expensive to host a list on MailChimp with something like 3000 signups,sthat I’m not sending out. So,sI’m still working on that one, but. and I’ll probably, it was hard to write about airline points during, during COVID, like who,Nathan: [00:46:15] Right. Yeah. I w I have more airline points now that I know what to do with that. I’m just dreamingDan: [00:46:21] yeah,Nathan: [00:46:21] what I could possibly redeem them for. So,Dan: [00:46:24] totally. Yeah. Yes. Exactly. So that’ll be a good, a good thing for me to restart with pretty soon. but anyway, so yeah, tool sets like I think sub stacks fine. It’s all in one. I like controlling the way my homepage looks. I like being able to pick out. Fonts from an independent font Foundry in New Zealand and use those for my website.I like being able to tweak the WordPress template when I want to tweak it. And I was able to put together kind of a stack of, of tools that,syou know, and I happened to see them in use for. Stratec Curry and for Kottke and some other sites and, and, you know, member full, thankfully worked straight out of the box.There were no challenges implementing it. it’s actually a very, very well made tool. And so I was very happy with that, that stack that I was using MailChimp,sWordPress member, full and Stripe. I have no. Secret desires to, to move off or anything like that. Like it’s all, it’s all great. I think interesting because it has massively lowered the technical and kind of infrastructure,sbarrier to entry.And I think it is allowing folks who are, you know, either less technical or just have no interest in running tools to start newsletters and. you know, and, and build subscription and membership based businesses. So I’m all for it. I think it’s great. It’s hopefully putting some pressure on member fold to improve their product.I love competition,sespecially in the, in the marketplace for tools. And will it grow into, you know, the valuation, it needs to make Andreessen Horowitz a bunch of money?sI would say there’s not a clear yes or no answer to that yet. We’ll see. But,syou know, I’m, I’m glad they’re doing what they’re doing.Nathan: [00:48:20] Yeah. So since you’ve been writing about tech for a long time,sI’d love your take on sub stack versus media. Right. Cause I feel like four years ago, five years ago, medium started this, this big rise. and actually when you look at the numbers from the medium puts out and they’re still growing like crazy, we just are all I’ll speak for myself.I have this perception, you know, that some of the people who were Yes they a lot of Dan: [00:48:42] people Nathan: [00:48:42] two years ago are now writing on sub stack. So I’m curious as to your take as to why, you know, what, what medium potentially missed and what sub stack is capitalizing on.Dan: [00:48:53] Yeah, well, first let’s caveat that like medium probably only still exists and only was able to raise the amount of money it was able to raise because of Williams is the founder and CEO. And, you know, the fact that he built blogger and Twitter,sgives him the ability to raise capital and operate at a loss and just kind of figure things out because he’s at Williams and he wants to, and,sthat’s fine with me.I, you know, I, I probably had a. You know, at first I was really intrigued by medium because they put so much effort into a really great offering tool. Which is something that most publications and content management systems don’t really,sit just, you know, you’re, you’re stuck using a commodity Wiziwig editor or, you know, WordPress now has, has many years later now tried to do their thing with Gutenberg, which I don’t love, but I tolerate. but yeah, medium was really special because it put effort into the offering tool and the reading tool. And the idea was let’s democratize publishing tools and let anyone write whatever they want. they they’ve gone back and forth now several times with owned and operated content or licensed content, you know, they were powering the ringer when it launched. sand they have since hired some really, really talented teams of journalists who work for medium writing publications, like one zero and marker, and a bunch of things like that. So it’s been interesting to see how, you know, you even say that they compete with their own. Publications now in some ways by,sby hoping to command more and more of,suh, of the attention by their owned and operated properties, or at least using that as kind of the, the thing that, that brings people in.And then perhaps either, you know, sort of like a, you know, any recommendation and algorithm then recommends cheaper content to people over time. Et cetera. Some of that won’t happen with medium because media, sorry with sub stack, because sub stack isn’t run by ed Williams. although I think the sub stack folks have, have done a pretty good job so far kind of building, building,sprominence and getting attention. sI think. To me, one of the more interesting questions is at what point does Substack kind of start becoming competition for some of its writers? you know, is there a big bundle at some point that Substack says, okay, for a hundred bucks a year, everyone gets access to all of our publications and they can’t opt out of that.Or, you know, if they do opt out of it, we’re not going to include them in our recommendation algorithm. So many things, I mean, should, should sub stacks include, should you be forced to include links to other Substacks at the end of your newsletters? Should you, you know, should you build awareness for other publishers on the network because you’re part of sub stack.Are you, do you own your brand or is Substack the brand that you’re contributing to? There are a lot of there’s nuances to all of those things, but it’s a question of. You know, are you really running an independent publishing business by using Substack Or are you just kind of, and they’re never going to say this like building up their machine that then they will use to build something way bigger than the sum of all of its parts. sthat’s an execution thing. That’s a, that’s a product vision thing. I won’t pretend that anyone’s figured all that out yet. You know, a lot of that stuff could happen. None of it could happen. We’ll see, but so far, I would say, like, if you’d asked me a year ago, what I thought of sub SAC, I would have said, they’re not doing a good job, getting prominent people using sub stack in the media industry.And I would say that a year later, like they did a really good job last year, getting people Nathan: [00:52:46] two years Dan: [00:52:47] Casey Newton and Maddie Blasius,sand other folks to, you know, set up shop on sub stack. And there were, you know, there were. Sub stack originals, like,syou know,sI think he did as the name of it. Like there were, there were folks like that,slong before, of course,syou know, the biggest one or one of the biggest ones was cynicism, which was,syou know,suh, China newsletter that,sthe guy who, who founded it, whose name I’m blanking out right now was an angel investor in sub stack.And they kind of built it for him. those things have, have existed, but what sub stack has done, I would say. Pretty much about as well as I would say they could have done last year was get people to leave their cushy, highly paid jobs at the Vox media is of the world to start sub stacked newsletters.And we’ll see what that looks like in a year or two. We’ll see what the churn looks like. You know, I’ve heard secondhand that they’re kind of giving,shealthy advances to those folks and kind of guaranteeing them some revenue. I don’t know what that looks like in a couple of years, how much those people like that job in two years, I still love mine two years in.It’s the best job I’ve ever had. I want to be doing this, you know, for many, many more years. but we’ll see. I don’t know. It’s certainly not for everyone.Nathan: [00:54:06] Yeah, that makes sense. So, I imagine running the new consumer for awhile, you have,sa good number of friends who come to you. And at various times ask like, should I start a paid newsletter? What advice do you have for me? And what do you tell them? Is it a path they should take? And if so, what, what are a few of the things that you’re like, okay, you got to get this part right.Dan: [00:54:26] I mean, if you like controlling everything about your life and your time, it’s great. If you love the idea of having. Influence over the way that your content, you know, not only the, what’s, what you write, but how it’s presented and how people engage with it. you have that ability in a way that you would never have working at a traditional journalism outlet. swhat I would say is you better be ready to do customer service all the time. You are, you know, asking people to update their credit card number in the backend politely you are. You know, dealing with people who want a deal or, you know, some custom version of the subscription all the time, you were trying to upsell people to team memberships and that kind of stuff.If you, if you enjoy that. And I actually really do, you know, I worked in retail in college. I love kind of that customer service and sales elements of it. I wouldn’t want that to be the whole job. And that’s why I never kind of worked in the business side of media, but I love having to me like the, the.The fact that my job has a little bit of sales and a little bit of customer service and a little bit of product and a little bit of design and a little bit of tech and a lot of editorial and some marketing and all that kind of stuff. Like to me, that’s super fascinating. And you have to do all of those things and you have to do them pretty well to succeed. sso far I’ve done them well enough,sand hope to get better at all of those things. If you don’t want that though, then don’t touch it. Like it’s not for you. And yeah. Sub stack is kind of trying to. Automate or at least take over some of those functions, but it is your responsibility over time. So if you don’t want to do that, then, then stay away from it.You can, I advise everybody to start a free newsletter and keep your friends and followers up, you know, up to date on what you’re working on. I think everybody should have that, whether they work in media or any field,sthere’s no reason not to. And it can only be helpful for your career. And especially if you work in publishing or media or journalism, but you know, that that is an entirely different thing than sending twice or three times a week, or even for,syou know, a high quality professional thing,sto people who are paying you.Nathan: [00:56:48] Yeah that makes a lot of sensesas we start to wrap up, we got a bunch of questions on Twitter and I’d love to run through some of those and a little rapid Dan: [00:56:55] Yeah Nathan: [00:56:56] They’re not necessarily all about newsletters, but,sJohn’s asking as a fellow Angeleno, who also lived in New York before, we’d love to hear your thoughts on West coast versus East coast media.What’s different, you know, what, what have you noticed.Dan: [00:57:11] I mean, it’s kind of,sit’s kind of a hard time to answer that question because I feel like I don’t live anywhere right now. Cause I basically just live in my house. sthere’s there’s no media scene happening anywhere at the moment.Nathan: [00:57:27] That makes sense.Dan: [00:57:29] what I, what I, you know, my wife and I moved here this last summer for mostly personal reasons.Like we just like it here. We had spent a lot of time out here. I think the startup and entrepreneurship scene in Los Angeles. Has a ton of potential. I think it’s very interesting. you know, the fact that Hollywood is here with, with such great creative talent and intellectual property and, you know, knowledge about distribution and marketing and sales, and most importantly, like making content that people love emotionally and,syou know, invest so much of their time and spirit in.I think it’s something that. You know, we can learn from, I, you know, and then the New York media world is so dominated by decades of legacy, print and broadcast, and now online media. but I think COVID is, you know, it’s, it’s not fair to compare anything right now. Everything is kind of, I think we’re figuring out a new reality over the next few years.I think there’s great potential in LA. I love that the ringer was started here. I love it. There are some really interesting publications being started here. I think, you know, some of the world’s next great media companies could be built in LA, but, you know, they could also be built anywhere.Nathan: [00:58:48] Right. Yeah, that makes sense. Okay. Matt’s asking what weird thing about consumers. Did you learn spending a lot of time in Paris and TokyoDan: [00:58:55] Hi, Matt. thanks for the question. yeah, I, I travel a ton before this,sbefore COVID, I hope to travel a ton afterwards. we did live in Paris for a few months, two years ago. I try to get to Japan once or twice a year. You know, I think for me, it’s just kind of being able to have the privilege of just observing how people in, in different places and cultures do things. syou know, my, my background is writing about technology and I try to think of technology less as an industry and more as. What I call a layer on life. So seeing how people in Japan adopted, you know, card-based,sSuica payments way before we had Apple pay or even contactless payments here in the U. or,syou know, I love going to London and seeing all the, the design and packaging design that on consumer products there that is, feels just much more vibrant than a lot of the.Big consumer packaged good brands had been doing in the US for a long time. I loved living in Paris and kind of getting to experience the old school way of, you know, buying essentially groceries, you know, every single day for that night’s dinner. but also, you know, seeing, seeing some sort of models that did not really exist in the US yet.So Travel just helps broaden perspective. I would say. I think travel is, is great for that for. Not just my line of work, but, but really everyone just getting to kind of see how things are done in different places. sometimes in ways that are super unique to that place. And then sometimes in ways that they could grow and scale around the world,Nathan: [01:00:42] Nice. Okay. Last question. Donna veers asking, what would you do differently if you had to start over? I assume that means start over with like the paid newsletter.Dan: [01:00:53] life or the publication.Nathan: [01:00:54] you’re like, well in middle school, I would have no, I, I, I think he means with the publication. [01:01:00]Dan: [01:01:00] zero things where I’m like, man, you really screwed that up. you know, I was lucky on day one to have enough people sign up that I knew it would be my job for the next several months. And then I was lucky in year one, that enough people signed up that it became my job, you know? Indefinitely. I don’t want to say permanently because what’s what is permanence? sso there’s nothing where I’m like, man, you really screwed that up. I think there, you know, one thing I, I wonder about is for example, and maybe you have the data to help me figure this out is like, should I be sending out newsletters on a predictable schedule every single week right now? I. Follow a kind of follow my productivity.I send out a newsletter when it’s done. And then,sor I usually schedule it for the next morning because people don’t need to know what time I finish it, but,sat nighttime, but, [01:02:00]syou know, would I be, would it matter materially if, if I were sending out newsletters, every, let’s say Tuesday, Thursday and Saturday morning, or is it okay with the fact that I send it out?Kind of on a, on a, I don’t want to say haphazard basis, but it’s, it’s not as,sas predictable, you know, Are newsletters the kind of things where people want to compartmentalize a certain time of the day or of the week to enjoy them and read them or are they happy to get it? When news breaks, which is kind of the model that I had had been following with most of my career, which is if there’s news, you better get it out there immediately because someone else is going to, if you don’t.So that’s one of the things that I think, I think about a lot. you know, I, I think my kind of happy medium is like, try to be predictable, but don’t like, let it rule your life. but I don’t know. I’m curious what you see.Nathan: [01:02:53] I think all things being equal, the predictability is better than not. And so not only day of the week, but also when we’ve talked about this on some other episodes, getting to a precise time of like 10:00 AM Eastern, every Tuesday, someone can look for that,sthat article to show up. and you’ll be right there in the, in your inbox.That said it’s important to ask. What’s the point of this newsletter right? Are you, are you as the author there to serve the newsletter or is the newsletter there to serve you? And so I think the point that you made of like, look, this is my creative schedule. This is when I’m inspired to write. And yes, I’m always going to meet the promise, I’ve made to the audience of two posts a week, or, you know, whatever that is.I’m going to hold up my end of the bargain, but it might not be worth it for me. to ha feel the additional pressure to hit an exact time for the somewhat marginal gains of,sthe predictability from the audience side. So all things being equal,san exact time every week, I think would help engagement, but I don’t know that the trade-offs are worth it.Dan: [01:04:02] So that’s something I’m going to figure out, but yeah, I mean, other than that, like the only other big thing would be, not, you know, you only launch once. This is the advice I give to people. You only launch once. So really make as big a deal out of the launches you can. And even when I launched, like one-off things like the consumer trends report, a launch date is, is launch day and you better put all the effort into that, that you can,sSo that, you know, like I was very pleased with my launch, but the question is like, could it have been 10 times bigger if I did this other thing or that other thing who knows?I don’t know. There’s no way to go back and figure that out, but it kind of is something I think about as I’m launching new components or new new things. And then the other big question is like, should I have launched with a free tier and what I have captured a hundred thousand emails in the first week.I have no idea. I don’t know. I know that a hundred. I think it was over a hundred thousand people visited the site. So I wasn’t going to get all of those people, but probably more of them than. So you know, then simply the people who signed up for paid, but you know, in this, in this world, you can only think going forward.I try not to dwell on the past of, of kind of how I did things and just try to get better all the time. Do interesting things, keep it fresh, be interesting every day forever. And so you know, and the biggest, the biggest takeaway is I love this model. I think it’s great. It’s not great for everyone. It’s great for me.I’m gonna stick with it. And I hope people come along with me for it.Nathan: [01:05:37] Sounds good. Well, where should people go to follow along and hear your story and support your work.Dan: [01:05:45] So The New Consumer is newconsumer.com and also, @newconsumer on Twitter and Instagram. My personal accounts are all @fromedome since III world in 1995. So you can find me on all this on social media as @fromedome. And @pointsparty, if you want to, someday in the future, read for free about credit card and travel points.Nathan: [01:06:13] Sounds good. Well, thanks for joining me. 

Tiago Forte is one of the world’s foremost experts on productivity. He runs Forte Labs, an education company that helps knowledge workers use technology to become more productive. He earns over $1,000,000 per year by using his 40,000-subscriber newsletter to sell his online masterclass, Build a Second Brain.In this interview, Tiago shares newsletter essentials, including:  How to get your first 10 newsletter subscribers. The best time to send your newsletter. How many subscribers you need to launch a course. Tiago addresses fears about sharing too much in your newsletters, explaining how we live in an age where people want to follow real humans with real problems that aren’t afraid to be vulnerable.Listen in to find out why Tiago, despite having a successful newsletter and online course, is still traditionally publishing a book about building a second brain.Stick around to the end of the show to hear Tiago talk about how he’s using the revenue he earns online to help his family build businesses offline. Links & Resources David Perell Building a Second Brain James Clear Teachable: Create and sell online courses and coaching Gumroad Tiago Forte’s Links Newsletter: Forte Labs Blog: Blog - Forte Labs Twitter: @fortelabs Episode TranscriptTiago: [00:00:00] In the short term, picking one theme and just hammering on that theme week after week after week after week, I’m sure is good for the early days.People know what you’re writing about. They know what to expect, they know what problem you’re going to solve. But I really think that’s short-sighted because in the long term they’re going to not have that problem anymore, or they’re going to develop more sophisticated problems or they’re just going to move their attention to some other part of their lives.And if you are this one-dimensional caricature of a person, you pretend you’re this person who thinks about SEO 24/7—which none of us are—they’re going to move on from you.Nathan: [00:00:41] In this episode, I talked to Tiago Forte about building an online course, growing his newsletter and so much more. There is a lot of great stuff in there. One: he’s earning over a million dollars a year off of his newsletter. He’s got 40,000 subscribers. We get into monetization, book launches, course launches, cohort based courses, so much stuff.And then actually, if you stick around to the end, we dive into, actually tiny houses and container homes and taking online revenue and bringing it offline, which I think is one of my favorite things. I’ve always seen me talk about that some on Twitter, but I haven’t talked about it a lot on the podcast or anything like that.So I love the idea of doing that, of getting family involved and really using it to teach business lessons to kids. So it’s a longer episode, but I think you’re going to love it.Let’s dive in.Tiago. Welcome to the show.Tiago: [00:01:32] Thanks, Nathan, really, really excited to be here.Nathan: [00:01:34] So you’ve done a crazy amount of stuff for the email,sover the last few years. And I think a lot of people look to you for successful strategies and all of that.sone thing that you did before we started recording this is you asked on Twitter,syou know, what should we talk about? You know,swhat your audience would like to hear.And one thing that that would be a fun place to start, w we’ll get into how to grow the audience and, and monetization and so much other stuff. I just love to hear it starting from zero. What are the first three things that you would do to grow your audience? So, you know, you’re giving advice to someone who’s has nothing going.All they know is I was told I should have an email newsletter and growing at I growing audiences. The thing I want to do this year,Tiago: [00:02:19] Yeah. Okay. Let’s see. Three top things. I think first one is manually add people.sin the early days, I don’t know if you want stories behind these, but if I had coffee with someone, last thing I asked, can I add you to my email list?If I met them on the subway, can I tell you it was one name and email address at a time? Because I knew there wasn’t much traffic to my website. People weren’t going to sign up just because I was really religious about getting people on there.Nathan: [00:02:50] but I’m just diving into that one for a second.sit’s so many people don’t ask right where they just say,sI’m doing all of these things. And over here, I’m trying to grow a newsletter and you can really grow an audience just by saying, Hey, will you join the list? And especially when you’re looking at a point where you’re say at the first.One two or three subscribers a day coming in you’re at that point, you’re going to wait. This is going to turn into 50 subscribers this month. Something, additional send an additional two to three texts, a day, emails, coffee meetings, any of that, like you could increase your growth rate by 50% by adding an extra couple of people.And so you could cut the time to a hundred subscribers in half just by asking. So I love that point.Tiago: [00:03:38] Exactly. I would add something else too, which is, it’s not just, it’s especially not about quantity in the early days, but quality too. Like when you have coffee with someone, you have such a deeper and closer connection to them.Which means, you know, maybe from a, like a numbers point of view at the time it takes for you to write down their email address, go home, open up the website, put it in, isn’t worth it. But that person is so much more likely to be someone who reads it, opens it and reads it. Who recommends others who engages with you? sin the early days, I really think quality matters more than quantity because you just don’t have the quantity.Nathan: [00:04:12] Right. Well, and actually we’ve talked to a few people like burn Hobart comes to mind who writes the which diff,swhich is a popular publication on subs deck. He doesn’t have the biggest audience out there, but he’s read by, by brothers Collison brothers Collison so many influential people in tech where they’re like, he’s, he’s just of right at the intersection of the things that they care so deeply about.And so. He has an incredibly high quality list. I also think about,sJim’s Clara and Ryan holiday, where they are getting replies to their email newsletter. It’s like, Hey man, we come out and talk to my team. What’s your team. You look, and it’s a professional NFL team, you know, and that’s the head coach, you know?And so you’re like, Oh right. Of course so-and-so is on my newsletter.sand so that point that you’re making about quality over quantity, I think is really good. And when you’re getting those first few subscribers from Twitter from wherever else, yes. You have some control of the quality based on the content you’re putting out there.But a lot of it, you know, it’s just, the average is going to be so much lower unless you actively recruit for your email list. Working in tech, you know, I’m actively recruiting employees. And the inbound that I get into workable is one level of quality. And the ones that I directly reach out to and say, Hey, we have a conversation about joining my company.The quality is higher. And so I’m driving the average up. So I love that point.That’s Tiago: [00:05:35] that’s really, it that’s really it. In fact, there’s things you can do with a small, you know, I think people that there’s so much focus on growth and I get that growth is awesome, but instead of thinking small list bad, big list, good. It’s, it’s really much more subtle than that, which is every single level, right?Like every single, point on that graph going up has pros and cons. But like maybe equal number of pros and cons. I’m starting to get into things now with a five-digit number list that are such a pain in the butt. Are such a headache that I didn’t have to worry about when it was small. Right. And one of the benefits of the small list is you can know most of the people by name on your list.If it’s, a few hundred people, that’s, that’s a unique, a unique window of time that is going to go away. I promise. So like, I feel like my message is Savor the small days, savor those first few hundred people. Cause they’re, you know, they’re, they’re true. Believers they’re following you because they like you, or they know you or they’re really into your ideas for their own merits.Whereas later on you get a lot of people that are following you, just because a lot of other people are following you.Nathan: [00:06:43] Right. Okay. So on this quality idea, I had a conversation with, Oh, Malik, the other day who,suh, is famous for creating giga home. And he’s been an investor for a long time, all of that. And he recently moved his newsletter over to convert kit. And so we were talking and he said that he’s going to. Trim his list down and make a rule where it’s only the 10,000 most engaged people.And if you don’t engage, he’s going to boot you out and make room for, you another hundred more highly engaged people who have replied and all of that.swhat’s your take on making somewhat an exclusive list or saying I’m actually going to go for quality over quantity so much that I’m gonna make a rule about it.Tiago: [00:07:25] I think it’s smart. It’s smart.sit depends as always right on your goals. Like for me, my email is more top of funnel. It’s like the big megaphone,swhich I can do that for free and be very kind of all-inclusive and talk to everyone because I have my online course, which is most of our revenue. It’s it’s our business.So I know that I have another way to make money and make a living. Whereas I think if you, if I had to have just a paid newsletter, I think it would be better to make it premium. I’d make it expensive, make it really in-depth and detailed and nerdy and niche and, and possibly li it’s. It’s an interesting idea that the psychology of limitation we’re trying this actually with, with David’s course, Rite of passage is going to be 350 spots.That’s it? And it changes all sorts of things about the marketing, about the people we’re hiring for the team. It’s like limited enrollment things have a different essential nature than things that are just open for everyone. And that I, myself am just beginning to kind of explore thatNathan: [00:08:31] Which I want to dive into there, but the first thing that we’re talking about is adding people to your list directly.swhat are the next two that, that you do if you’re just getting started?Tiago: [00:08:40] Yeah, I think the second one,swhich is it’s totally,scommon, almost universal advice, but it took me them the number of years, it took me to really put my trust in this, which is an exact send time every single week. I resisted this. Like I heard it on podcasts on things that I would read for years, probably from 2013, when I first started collecting email subscribers to 2000, I only started doing it actually, when I moved to convert kid about a year and a half ago.And it’s, it’s funny because in my situation I’m a productivity guy, right? So there’s this fundamental paradox where my whole life mission is to have you spend less time on email. And I think that’s why I resisted this idea I’m going to be sending, tens of thousands of emails, hundreds of thousands of emails a month it felt totally paradoxical.Like I was being a spammer or something.sbut I think it really comes down on the value you’re providing the density of insight. You know, the value provided per minute of reading time, which I think is higher for what I send out than almost anything else.sbecause if you are crowding out lower sources of information, lower-value sources of information and making the average amount of value they get per email rise, then you’re, you’re benefiting them.Nathan: [00:10:00] Yeah, that makes sense. you’re talking about like, not just saying I send my newsletter every Tuesday, but saying every Tuesday at 10:00 AM, it will be in your inbox.Tiago: [00:10:10] That that is only about a month old. So I went through through,sthere’s a whole arc. I went through from sending once every quarter. And, and only when I had a really important announcement, something really huge had happened then about a year after that, it was maybe once a month, but approximately once a month, I would only send an email out when I had something to announce.Right. Something big or small, then eventually it became, a little more regular, like every two weeks and then eventually every week. And just about a month ago,sI started seeing some interesting observations online a time I can’t tell you how much I resisted this. Nathan like the idea of being almost like a.Like a TV show it’s coming on, 5:00 PM central. I I got into this business so I could have freedom and flexibility and work whenever I wanted. And the idea of of tying myself to this time, I just hated, but the results speak for themselves. It’s just predictability. It’s like this catalyst that you just add a little vial into your potion and it massively increases the effectiveness of everything else you’re doing.Nathan: [00:11:18] Nice. I love it. What’s the third thing that you’d recommend.Tiago: [00:11:21] I think the third thing would be, which is kind of counter to a lot of advice out there is to talk about all parts of your life.sthis is something I think, I think is a, it’s definitely a strategy. Like you have to choose it for yourself, but in the short term picking one theme and just hammering on that theme week after week after week after week, I’m sure is good for the early days.people know what you’re writing about. They know what to expect, they know what problem you’re going to solve. But I really think that that’s, that’s short-sightedsbecause in the long term they’re going to not have that problem anymore, or they’re going to develop,smore sophisticated problems or they’re just going to move their attention to some other part of, their lives.And if you are this one-dimensional caricature of a person, you know, like you, you, you pretend you’re this, this person who thinks about SEO 24/7 which none of us are, they’re going to move on from you. And so I talk about, and I have marketer, friends read my newsletters, and they’re just like, you’re crazy, man.Like I tell, I’m talking about my family, I’m talking about my container home business I’m starting with my, with my brother, which I’m sure we’ll talk about. I know you’re into tiny homes. sthis, this Tuesday, tomorrow morning, I’ll talk about my first angel investment I just made,sthings that are very far from the topic of my newsletter, which is productivity.But what that means is people grow along with me. You know, people that started following me in their late twenties when I was in my late twenties can still follow me in my mid thirties because we’ve evolved and we’ve grown together and they’re interested in me as a person, not just as a thought.leader Nathan: [00:12:59] I’ve done specifically in, in billionaires that are under my own name rather than on a very specific topic. And we get into a ton of details. I don’t know if that’s the conversation we want to have today, but on the pros and cons of it.But I started my audience around,show to design web applications and iOS.I don’t talk about that at all anymore. And so if it was a, you know, if, if iOS design, well, actually my first newsletter was the iOS design weekly. And so that was what everything was themed around rather than Nathan Barry, it would be really hard. Like I would have shut down an audience and moved on and then I would have done another one around book marketing and I would have done another one around SAS grit, you know, and what you’re talking about of just living your life,swith whatever you’re interested in, then people self, self, select, self filter for that.And then as my interest change, people come and go or their interests changed with me.So that makes sense.Is there a time you’ve shared things or, you know, or brought your personal life,sopened that up to the newsletter that you think you thought later, Maybe that was a bit more than I wanted to do, or maybe that was a big stretch.Tiago: [00:14:12] never. I haven’t even approached the boundary of what would be inappropriate.Yeah. I’m not sure there is one. I had a blog post. I sent out about my own personal, healing process through trauma. I had one, I’ve had things talking about things I’ve worked through with my family,sabout my health problems.sI think we’re in this age where. People want to follow real humans that have real problems and that aren’t ashamed or afraid to talk about those problems.And then trying to pretend otherwise, maybe in the short term makes you look impressive or something, but in the long termsI even think has, it has other weird side effects. Like people don’t treat you as fully human. Like they’ll, there’ll be harsher or more demanding or less fair or less,skind if you present this unrealistic image, whereas if you’re a little more vulnerable and open, they, they treat you like a human—who would have guessedNathan: [00:15:15] That’s interesting. I’m realizing a lot of people have talked about when once their newsletters reached a certain size, the audience. Maybe turning it against thema little bit, or are you getting people who are not sure that you’re like a human and I have not had that experience. And I’m wondering if that’s, because I’ve always had this approach that you described.Thing of this is my whole life, you know, I write a year in review, post it’s as much about how ConvertKit has drone, how my book sales, whenever this has grown as it is about my personal travel and an angel investment in buying a farm and building a tiny house house and any of that stuff. And so I bet.You know, it sort of self-selects for like kinder people who are more interested in, in me rather than just being like, you know, where’s my productivity advice. Where’s my design advice orwhatever else Tiago: [00:16:02] Exactly. Yeah. I think part of it too, is the subject matter. my business partner, David Perell who you’ve had on the show,swe compare notes and we have similar audiences writing, about similar things in a similar style. He gets way more hate mail. And I think it’s because. He’s making his essays that he writes are these grand theories about how the world works, how culture works, how society works, how friendship works. swhereas mine, I, I’m more nerdy and almost technical about productivity. I, so I sort of, I, I,sit’s just harder to attack really niche, subject matter, whereas any grand theory, half the people love it and half, absolutely hate it because you violate their beliefs. Nathan: [00:16:46] Yeah,that makes sense. The more surface area that, you know, you have to step on and someone’s going to be reading along. They’re like, Oh, I love this. This makes sense. No, that part I totally disagree with. And then the hate mail starts.swell, take us back. What did it look like when you were getting into building the newsletter and,smaybe what was the path of the first thousand subscribers and then,suh, to 5,000 beyondthat Tiago: [00:17:13] Yeah, good.slet me see how I can summarize this. I started around 2013, which is the year I became self-employed. I had a MailChimp account, like so many others, and I just said, who well, what do people use as MailChimp? And,sthat was the year I’d had my first project, which was an online course on productivity.And I just kept an email list initially of my customers. It was just people who’d taken my course. I thought, Hey, let me just keep in touch with these people. And I didn’t really didn’t emphasis size it.sfor several years after that, I slowly grew slowly, maybe into the few hundreds over the first two or three years.Nathan: [00:17:51] How are you selling the course without the emaillist Tiago: [00:17:54] through Skillshare. It was discovered. Sure. Of course, but then like so many of my kind of generation,swe were burned. Right. If you don’t control your customer list, it’s not a question of if you’re going to get burned, it’s just when there’s, there’s no avoiding it.Right? Cause I think something happens Skillshare needed to be profitable. And the easiest way to do that was to,sI think they switched their model from a,sfrom a. It was a Allah cart model where you just purchased a course. I think I would make like $30 per sale to a, like an all you can eat model kind of like Spotify, where suddenly I was making 30 cents, like overnight from one day to the next.And that was also the night that I realized I couldn’t actually message my customersNathan: [00:18:41]sno. Yeah. That that’s painful.Tiago: [00:18:46] really painful. And actually, now that I’m thinking about it, I had to learn it again. Because I first started my blog on medium. Right. It was just easier. I didn’t want to deal with hosting and WordPress and all that stuff. And they would have these things called letters, which seem like just a very easy to use convenient newsletter.You could go in and message all your, you know, your, your followers on medium, but then have some time after that, I think I had something like 5,000 followers on medium. They changed the settings. And now if someone opted out of notifications from any medium publication, They also didn’t get your letters.Ouch. Nathan: [00:19:22] Okay. So that’s the painful lesson learned twice. I really sinks in at that point. And so then, then at that point, you’re going okay. I have to control my audience.sso I imagine is that when you move selling courses over to teachable,Tiago: [00:19:39] it is yeah, maybe around 2015.sthis was when I got serious about controlling my infrastructure. Right. I moved to,sa stolen MailChimp,sbut started taking it more seriously. Like I said, adding people manually really paying attention to that.smoved to teachable, which is sort of a build your own school,splatform because of the key feature that you control.You had the email addresses Nathan: [00:20:04] Which I just want to point out,slike now that might seem, well, of course you’re selling the course, you should control it, but with Skillshare and you, to me and these other platforms and Amazon for eBooks and, and all of that, that was a big debate at the time of, you know, this sort of bring your own an audience, get all the benefits from it.Instead of everyone was looking at the marketplace model. Okay. Of,syou know, they, I will create the content. They willbring the demand.And I guess they’ll get all the long-term benefits, but I’m getting money. So maybe that’s okay. And teachable,steachable Gumroad,syou know, a few of those platforms were really at the front of saying like, no, you should, you got to do way more work, but you should get all the longterm benefit from.Tiago: [00:20:48] exactly it was. I think that that first early, maybe not first, but those early ways of creators, we were just willing to take whatever terms. I mean, the idea of making a living online was still so novel, you know, six, seven years ago. It was like, yeah, we’ll just we’ll sign anything.We’ll agree to anything. And then after a few years you go, wait a minute, I’m working like a dog and I better be building some sort of asset to hearNathan: [00:21:14] Right. That makes sense. So what works,sto scale the audience, you know, as you, you got into the 5,000 subscribersand beyond Tiago: [00:21:23] yeah. So from, from 2015 to about 2000, Nathan: [00:21:27]sTiago: [00:21:29] eight, let me think. Now, in 2018, 2000. I actually switched to convert kit August, 2019. So I guess about three, four years, I was still in MailChimp, but just,sblogging blogging was really how I continue to get the vast majority of my subscribers. I love writing.Writing is easy for me. That’s like the thing that I know how to do that is. Is relatively easy for me and not for others is, is not just writing, but super in depth, sometimes called long form essays where you do the ultimate guide to something, or really dive deep into an idea. Often I’ll spend months and months researching and writing and editing a post there.They’re kind of more like small books than blog posts.sand then I was still for, for all that time and still to this day in many ways. So timid. You know, still to this day, there’s no pop-up of any kind. There’s a form at the very bottom. You make it down, this thousands of words, and maybe you’ll find my form in most of my posts, Nathan: [00:22:24] But really quick, that lens to quality over quantity again, because do you want, you know, people who click to your site to be on your newsletter, many people, the answer to that would be yes. In your case. You’re saying I want everyone who reads a post who clicks inand reads a full post. You’re my people.I want you to be on my newsletter. And that’s adifferent bar that you’re setting Tiago: [00:22:48] Exactly. Yeah. Yeah. So by around mid 2019, I had about 5,500 subscribers.sand that was when I started working closely with David Parell,swho we mentioned before.And he was just so fanatical about email. So convinced it was the future. That he kind of convinced me or influenced me, especially since we were becoming business partners to just go all in on email. And as soon as I decided to do that, it was became so clear that MailChimp couldn’t do it. Just wasn’t, you know, made MailChimp has made for like a, you know, a cupcake shop on the corner in one city in Ohio or some, some specific place it’s not made for creators.And that’s what I loved about that. You were, you were, you took the risk and it was a risk back then to say that we’re for, for creators, it wasn’t clear that was going to be such a, a great, a great audience.Nathan: [00:23:42] Yeah. And that’s actually kind of crazy to think about, because I remember probably 20, 15, 2016,sactually being in San Francisco and trying to raise venture capital, which I’m very thankful that I failed at.sbut having those conversations and everyone brought up that the blogger market, the creative market is not big enough.You can’t build a business there. And, you know, we said like, okay, but that’s fine. We’re going to anyway. And now, as everyone talks about the creator economy and all this stuff, like no one is saying that it’s not a big enough market, which is just kind of wild, how that changes over time.Tiago: [00:24:21] Exactly it’s changed so much.sso yeah, just to kind of complete the history from August, 2019, with 5,500 subscribers that I imported into convert kit.sit’s now about a year and a half later and we just passed this week. 40 F 40,000 subscribers.Nathan: [00:24:40] That’s pretty fantastic growth. What are,sso I noticed on your site, you know, you have a. You’re promoting your newsletter. Of course, as you talked about,sand then you’ve got your top 10 productivity tips,sthat you’re, you’re promoting, have you done other like content upgrades or, you know, opt-in incentives that havedriven growth Tiago: [00:25:01] have definitely not as much as I probably should have there. There’s so much value low-hanging fruit with lead magnets and content upgrades.sbut I’ve tried, I think I have about. 30 or 40 different forms that I’ve tried.sthe one that, that converts the best and it converts around 3%, which is that’s okay.But it’s kind of average,sis my top 10, most popular articles. It’s like, there’s, you know, 500 posts on this blog, which you can only see six at a time. If you want to just know the 10 most popular things I’ve written, put your email address and I’ll just send them to youNathan: [00:25:36] You know, what’s interesting about that is. It’s really simple. I think a lot of people are like, I’m going to create this elaborate ebook. I’m going to film this whole free course or I’m, you know, any of this stuff. And you’re just saying like, no, I’ve been at this for seven years now. And here are the 10 most popular things that I’ve written. And, and so anyone who’s probably been doing it for at least six months to a year, has those 10 pieces of content that they’re most proud of. And then you, when you write something later that you’re even more proud of, you just slide it in and replace something else. And. And that’s pretty straight forward.So that’s awesome to hear that that’s converting reallywell Tiago: [00:26:11] Yeah. Yeah, it is.sthat’s really the main mechanism and it, we, we created an in our website template so that every blog post has the form at the bottom. And then for certain posts, usually ones that are more popular that are designed for an external audience. I’ll add a form in the middle of the post. sbut no, pop-ups no heavy incentives. No, no paid. We don’t, we don’t do paid acquisition for subscribers or even our products at all. Everything is a hundred percent organic.sand that, that list is our biggest asset. I mean, we sell multiple products over multiple timescales with this list of now 40,000 people.Nathan: [00:26:50] Yeah, that makes sense.slet’s talk about courses for a second then I want to get into, you know, a business partner,sin that relationship with David.sbut talk through a couple, a couple of the courses, and then if you have for sharing some of the revenue or ballpark figures that you’ve made.Tiago: [00:27:05] Yeah, of course, I’m, I’m a huge evangelist of online courses. I think they’re just, just beginning we’re in the earliest days of this, especially the kind of course that I, that I teach and my me and my business partner, which has cohort based courses. I don’t know if you’ve seen this, but they’re called CBCs.And the whole idea is people don’t want to sit, spend even more hours sitting in front of a computer, watching a video of you talking and taking notes by themselves. They want to learn together. They want to learn in community. They want interaction and feedback and coaching and zoom. Which, you know, has only been around the past few years and uniquely enables that.And now we’re in this kind of incredible moment that, you know, a year ago I would have to promote zoom almost as much as I marketed my course, because that was the barrierentry You know Nathan: [00:27:55] Well, it had to be downloaded. People were like, wait, what do I do? What is this? And so much stuff. And now everyone knows what zoomis Tiago: [00:28:02] It’s honestly a huge change. Like we’d have to train, people, teach them how to use zoom. Now that’s a given.sand what that, I think what that allows is of course, like bigger impact on, on,son students,shigher retention, much higher completion, all these things, but since this is a podcast for creators,sthe interesting implication there is you can charge way more money, way more.You can charge way more, charge, a lot more money,swhich means you don’t need nearly the audience size. No, this was, this was the big shift for earlier creators. They had to build enormous audiences because they were monetizing a few bucks at a time, you know, an ebook, a hundred dollar course, these kind of low dollar amounts.But now it’s, it’s very reasonable and kind of become, becoming expected to charge 500, 1,015 hundred, 2000. If, and this is the thing they have direct contact and exposure and they get to work with you as the expert instead of just watching a prerecorded video.sso I think so I think that’s the big opportunity is to it’s it’s kind of like structured consulting.Nathan: [00:29:13] Yeah, that makes sense. And a lot of people, you know, the productized consulting movement had a big,swave maybe two or three years ago, and this is the course equivalent of it. I’d probably make the equivalent or the very acquainted, a lot more to a university class, like a really good university class rather than,syou know, the video version of the textbook, which I think is what a lot of people were making is here’s here’s the content good luck.And then they’d be like, yeah, I make sales, but only about 10% of people who buy, actually go through the material or 20% or something like that. And. And then exactly what you’re talking about. People want that interaction, they want the engagement, they want to meet other students. Like that’s a big thing of showing up and saying, Oh wow, I could buy this and end up with a community as well.If people trying to accomplish the same thing. And then I think most of all, I’m curious for your take. I think people want the accountability. They want someone that’s saying like,syou said you were going to do this by Friday. Wait, why isn’t it done yet?You know, in that peer pressure.Tiago: [00:30:14] Exactly. That is a, that is a beautiful metaphor. Self-paced courses are like the textbook, which like it’s a hundred bucks and you’re like, Oh, this is our rip off. Where can I photocopy this? Or Dell hit it online. Right. And cohort-based courses or anything that involves interaction is like the class where, you know, I don’t know how much, I wonder how, what, what is the individual.Average college class costs probably at least a few thousand, right. With, with the way that college, up Nathan: [00:30:45] Yeah, let’s say, I mean, $500 a credit has to be the minimum. I mean, college, when I was going to college,s13 years ago at a state university, it was $300 a credit. So it’s gotta be way more expensive than that now.sso yeah, you’re looking at 1500 to 2,500 per college class.sand I’m just going to guess that, you know, a professor at Boise state university is not, they’re going to be great.That’s the school that I went to, but they’re not going to be world-class. They’re not going to be, you know, at the top of their game where as a lot of these,syou know, creators that you can buy courses from now, sreally are.Tiago: [00:31:27] Absolutely. They’re not going to be the best necessarily.seven if they are the best they might not. I think it’s, it’s different skills to be very, to have expertise and to know how to teach it. I think we’re starting to learn are very different things. There’s some edgy know entertainers out there that are better.Teachers listen to Dave Chappelle, you know, he’s a better teacher and storyteller than most people who are like, it’s a, it’s a completely separate skill. So there’s that, I mean, in college you don’t get access to every student who’s ever taken that class and every student who will ever take that class, which is trivial to do with an online course.Right. You just put them into the same community or the same discussion forum. It’s a complete, I love that metaphor. And it’s a complete kind of,srevolution in how people think about paying for education.Nathan: [00:32:16] That makes sense. What are, so you talked about the difference between having the skillset and the knowledge versus teaching it. those gaps of those gaps when you come across someone where you’re like, wow, you’re an incredibly, I don’t know how you’d say this.syou’re incredibly knowledgeable and the why you keep yourself and not a very good teacher.What are those gaps that usually see and what, you know, what are, what are some of the advice or resources that you would refer to them tobecome a better teacher? Tiago: [00:32:43] Yeah, so this, this is,sthis it’s, it’s funny. If you just think about your experiences, it’s obvious, this is true. Like we all know the person who’s, you know, PhD in theoretical physics and they’re clearly brilliant. You don’t get to that point, you know, without having brilliance, but in a way, the more expertise you have and the deeper zoomed in you are to that topic, the less you can relate to anyone else, the less you can see outside your little box. umbrellasand so I think in, in a way, a lot of expertise can actually reduce your communication abilities. Cause you just forget, you forget what it was like to not know all the stuff that you know,swhereas the skill of teaching it’s, it’s more like, you know, it’s, it’s charisma, it’s being able to use metaphors.It’s having a lot of energy on camera. And, you know, communicating enthusiasm and, and, and insight and all these things. It’s empathy, it’s coaching. It’s a whole nother skill. We haven’t even touched on it’s this whole package of other skills that, that are becoming more important online, where the quality and the way and the style and the personality of how it’s presented are just as important as, as the content.sand, and what I would refer people to is. It’s really funny actually, because that, that mental of teaching people are really reluctant to take on. I’ve noticed, you know, I’ve had people, a guy who has a million followers on YouTube, tell me, Oh, but I’m not a good teacher. I’m like, what. What are you talking about?We put teachers on this pedestal, like there’s some magical power that they have when it’s really just, it’s, it’s a bundle of facilitation, communication, speaking,scoaching kind of all mixed in together.sand so my advice would just be, find venues for it. You know, back in the day used to be local meetups.I kind of cut my teeth on public speaking at free, you know, local meetups these days, I guess that would be like, You know, zoom events, Crowdcast calls,swherever you can find, even just a few people willing to, to hear what you have to say. You can practice those.Nathan: [00:34:48] Yeah, that makes sense. I, I think just articulating that they’re different skills like being great at design and being great at teaching design are two different things. And when you label it as such, then you can go, Oh, I spent a lot of time honing my design skills. I should probably spend some time learning my teaching skills.If I want to do this course, someone that I always look up to,sI’m really enjoying reading his material is Richard Fineman of taking these complex concepts in physics and one making them really entertaining because he knows that if he can hold your attention, you know, then he like, that’s the first gateway to teaching you all kinds of stuff, because if you close the book and walk away, then you know, he had no hope. sso just in telling these incredible stories, but then also just the, the continued focus that he always had of. Bringing things down to the most, the simplest concepts and saying like, yes, this is wildly complicated, but here’s how you can understand it really well. And so I think he’s a great example.Tiago: [00:35:48] Yeah. That’s that’s the secret, the, the rare thing about him, there were many things, but that he happened to have deep. Theoretical, you know, knowledge of the subject matter better than almost anyone. He won a Nobel prize. He was on the two ends of the extreme spectrum. He was so good at the subject matter and he was so good at teaching.And that is what’s really great.Nathan: [00:36:10] Yeah, that makes sense. You touched on storytelling and David Paul, your business partner mentioned this on Twitter as well, that he wants you to talk about more.show do you think about telling stories and then from there, how do you think about telling stories as it was into a course launch orsomething that you’re trying to promote?Tiago: [00:36:30] Yeah, let’s storytelling. The way you think of storytelling is just letting people in behind the, like, behind the curtain, into the, in, onto the backstage. So much of what we do as creators is a stage. You know, the, the, the, you know, how it is behind the scenes, it’s just a total mess. Things are flying.There’s, you know, it’s just a disaster. Also. You can get that performance, whether it’s a piece of writing or a webinar, or a course looking all polished and perfect. And this kind of goes back to what we were saying before, where, where I think people want to see behind the scenes, they need to see behind the scenes behind the scenes is actually where the most interesting stuff is happening.It’s what makes people actually actually understand what you’re doing. Instead of being kind of faked out by this, this, you know, polished image. So I think,sI mean, from a, from a practical point of view, what really enabled this, what was actually a very specific,sconvert kit feature, which is link triggers, link triggers.I don’t think people understand link triggers along with tags. When I, when I was going through your guys’s,shelp documentation and I got linked triggers, I just had to like stand up and go for a walk. I seriously did. I just like walked around the block because I realized how constrained I had been in my thinking and my strategy and my business by this idea that my audience is one giant group, like in a stadium.And there’s only one way to talk to them, which is a giant megaphone. Which has so many limitations, right? With, with link triggers, which, for anyone who doesn’t know is, is couldn’t be simpler as the link that says, click here to learn more or click here to find out more or click here to get updates. Okay.And instead of the person having to enter their email address or fill out a form or anything, or even go to a preference, you know, contact preferences page, and try to decipher all the different preferences. They just do one click. That is it’s a world changing thing because suddenly my business went from a stadium to like a conference where there were dozens and dozens, hundreds of little breakout rooms, each group having their own conversation and their own interests and their own activities.If you look at my ConvertKit there’s, you know, maybe 30 to 50 tags. And what’s, what’s so remarkable about that too, is it’s bottom up. Right? I didn’t start my strategy and say, okay, these are the 50 things I’m going to talk about. Let me create all these tags and then just force people into those groups.It was in the moment, right? Sometimes I’m actually writing the email and I go, Hey, this thing I’m talking about, maybe people want to hear about this into the future. Let me just right there. You know, link, trigger a tag subscriber, create the tag right there in the dialogue. And suddenly I have a whole new interest group. sand so, so what that allowed me to do is everyone’s in the stadium. And I mentioned sometimes in a PS, I’m going to be selling this product and that’s from a $10 ebook to a $75,000 home. Like, this is the same strategy I used to sell actual homes, which is if you want to hear about this click here, and sometimes I’ll do that over time.So that, that, that tag, that, that smaller group of people gets bigger. I kind of add people to it over time. Once it reaches a critical mass, which could be 50 people, a hundred people, 500 people, then I can write a whole sequence. Right, which is another feature. It’s just a series of emails, but this is the thing.Sequences are so hard to write, take so much effort, but I’m willing to do it because the group is already there. I’m not writing the sequence like speculatively. I know the people and their names and their whole click history of the people who will be receiving this. It’s a, it’s a different thing.Nathan: [00:40:20] Yeah. Yeah, that makes sense. And so you’re talking about with stories, taking people behind the scenes. So I think people look at it and, and say like, Oh, this there’s this elaborate lead-up that you have, or that kind of thing. And you’re just, maybe I’m projecting a little bit because this is what I did.I’ve just like saying, Hey, this is what I’m working on.Let me tell you more about why built it. Let me tell you more about why I think you’ll better benefit from it. Hey, here’s how the launch is coming together. You know, I’ve got about half the book written, working on editing, you know, like a lot of details like that.And people were like, wow, it’s masterful. And I’m like, or it’s a real update of what’s going on in the progress on the product that I’m hoping you buy in,sfour weeks.Tiago: [00:41:03] No, that’s, that’s exactly it. It’s, it’s, it’s the same. I write about what I’m obsessed with. If people respond to what I’m obsessed with, I write about it more. If they still respond to it, then I create a tag and start adding people to the tag.And if they’re still really into it, I’ll think about creating something and selling it. But it’s all bottom-up It’s all reacting to people’s behavior.sand the, the monetization is mostly just a way to fund my hobby. It’s just a way to fund my learning and it makes use of the learning I’ve already done.It’s not that I’m going off into this whole new thing. I’m just packaging up what I’ve already created and letting the people who are most engaged, which is not everyone,spurchase a shortcut, right. A shortcut to the same outcome.Nathan: [00:41:48] Right. Just say that you phrased it as funding. Your hobby is to be clear. This is a course businesses earning over a million dollars a year.suh, So I don’t want to downplay things by just saying like, Oh, it’s a hobby, but at the same time, I think that phrasing gets into some of your, your thinking around it, of like, you’re not approaching this as the most perfectly refined business where everything has to be figured out in advance.You’re saying these are my interests. This is what I care about. And if I pursue that and do it with excellence, then the money will follow with it. I don’t get the feeling that you were setting out with the. The money or the income being the primary goal. Is that right?Tiago: [00:42:34] it, it really isn’t. I’d say that the core stuff is the stuff that I try to be most businesslike. And try to be most professional and strategic, but then there’s this long tail of, of increasingly random things that I’ve been to, that that are more like the hobbies. But,syeah, you know, I don’t really know another way of operating.I’m obsessed with things almost in voluntarily. I don’t really have another choice. And once I get into them, I want to make things because that’s just the fastest way to learn. There’s just nothing like getting your hands dirty. And once I’ve made things, it’s so easy with digital, the digital world to just duplicate it endlessly and sell it. sit’s, it’s kind of a, a natural outlet kind of flow based on my kind of obsessive personnelNathan: [00:43:21] Yeah. Yep. That makes sense. I wanted to ask about,sjoining forces with David Perell and, and what made you to come together and say, Hey, we should do a course together.sand what would you say to other creators who are thinking about partnering up on a business venture?Tiago: [00:43:38] You know, we just recorded a podcast where we talked about this. I think partnerships are really under utilized a format for creators. Which kind of makes sense, like, right. Like we get into this for radical, totally unfettered independence from time and space. And now suddenly we’re going to link up with this person. sbut you know, you know where that came from. I mean, first it was just the fact that,sI had a course on note-taking and one of the most natural audiences for that was writers, but I didn’t really have time or bandwidth to make a whole separate course on writing, even though I was a writer. So David took my course.He was kind of like my star student, you know, straight a student. And he said, let me build that course. Let me do the follow on the part too. And you’ll benefit because people will want note taking skills in order to become better writers and I’ll benefit because the people finishing, building a second brain, which is my course will have kind of a step two to go onto.Okay.sand initially we were just gonna kind of do a little collaboration. I think that’s how the best partnership start is. Just let’s try this thing, but over time we just had highly compatible ways of thinking highly related, but kind of different strengths and weaknesses.sand then the key thing that really took it to a real partnership was which I think a lot of people who have launches will relate to.Launches are incredible. Whether it’s for a course or anything that whole buildup of energy and enthusiasm, and then the thing drops, but it results in a business that is so insanely cyclical. That it’s really stressful, right? Like, like our company, we make 90% of our revenue in one week in April and one week.Nathan: [00:45:21] Wow, Wow because you’re building up to this massive launch and, andeverything that comes down to a single week.Tiago: [00:45:30] Exactly. It’s a lot of pressure and it’s, it feels risky because there’s just variables you can control, you know?sand so, so, Oh, so what happened is I wanted to hire an employee and so did David.sbut this is another challenge. Creators face is, you know, you’re making, you know, a hundred, 200, even $300,000 a year.You’re doing awesome as an individual. You’re so happy, but to go from that, to hiring an employee, especially one that’s really talented and skilled and that you want to pay well is a giant chasm.Nathan: [00:46:03] When the paycheck should show up every two weeks and the launch revenueshows up twice ayear Tiago: [00:46:11] Exactly right, exactly. It was too risky.snot to mention the fact that not only is the revenue cyclical, but the work is, you know, we, we do pretty much all the work for the cohort in the four or five weeks before launches, then there’s five weeks of cohort, but then once the cohort ends there’s it goes almost to zero there’s very little work in between.So, you know, if I’m going to be paying that, that, that,ssalary all year, I don’t want to be paying for these big gaps when there’s not much going on. And so we combined forces and it’s kind of a Tik TOK model. I do my cohort and it’s this big ramp up. And the employee that we work with, his name is Willman and he’s amazing.He works almost exclusively with me. And then as my course ramps down David’s course ramps up and will goes and works for David. Right. So we share the costs. We each pay 50% of his salary. We share the risk and a really unexpected benefit. We share the learnings, right? Like each cohort, we come out with a whole new set of features and innovations, but then we’ll, who’s across both gets all those learnings and transfers them directly over to the next court and back.So instead of learn, having that learning cycle twice a year, we have it four times.Nathan: [00:47:26] So you’re launching each course twice a year and you have them spaced out so that.He stays busy full-time all year round.Tiago: [00:47:37] Exactly. He stays busy and we just Nathan: [00:47:43] Yeah. Sounds well. Let’s dive into a little bit, as we start to wrap up,stalking about the different methods of monetization, we talked about courses,syou, you and I actually have the same book agent and you just signed a book deal. And so,sLisa Dimona for anyone, who’s curious, just a, represents a second and James clear and for meet safety and so many other people. sI’d love to hear, well, let’s talk about the book for a second. What, what’s the reasoning behind doing a traditionally-published book?sit’s clearly not revenue because you’ve got the revenue side covered pretty well. It’s clearly not. Knowing your customer or getting their email address because that’s not an option. stake me through it. Why go traditionally published? Tiago: [00:48:32] Yeah, this is, this is something I thought about for a really long time.sit has to do with, with my goals, which is, you know, after building a sustainable business and having an audience and a customer base. These days, the thing that’s most important to me is to get this idea, which is this idea of a second brain. sthe possibility you could have a system of knowledge management, you can actually have a software program not just, write my grocery lists and some, ideas from a book, but it’s like a, it’s a, it’s a brain you put into it, all your learnings, your assets, your, your knowledge, your expertise, your meeting notes, your book notes, your quotes, all the stuff we’re surrounded with surrounded by goes into this system.And then from that point on you just reap the rewards. It’s like this constant, you know,suh, source of,svalue for whatever work you’re doing.sI just really think that this idea, which I didn’t come up with, by the way, it goes back to like, you know, whenever Bush and even further back, Paul Otlet goes back at least a century or more it’s it’s time has come.It’s time has come. It’s been these really nerdy Silicon Valley circles for decades.sthe early internet pioneers were super into this stuff. You know, this, this is what they thought the internet was going to look like a system of knowledge management.sI just think we’re at this point, this tipping point of information overload,snot to mention, you know, confirmation bias and everything going on with filter bubbles that people want to and need to cultivate their knowledge in a really concrete way.Rather than just thinking of knowledge as like this free floating, mystical thing out there.sand that’s, that’s my work, but what a book does is it can just reach so much further. So-so-so much further to an extent I think internet creators don’t appreciate, you know, we think, Oh, everyone is online.Everyone, has a computer or at least a smartphone. Most of the humans on on the planet have access to the internet in some way. But. If you really look at who were the, nerds and the people in this niche, it’s so tiny, you have to have such a specific background.sI’m, excited about translating the book and getting it into, I just have these images in mind of a student in Brazil, which is where my family is from in a small-town bookstore, picking up a book in Portuguese.You know, where the, even the terminology and the metaphors and different things are written in a way they can relate to. And them thinking, Oh, maybe I could build a second brain. I could have a system of knowledge management.syou know, these sorts of little images and stories is what really inspires me.as powerful and widespread as the internet has become books are still the most universally-accessible medium of information there is Nathan: [00:51:29] Yeah, I think that,sI’ve come to a very similar place and that’s, you know, that’s why we both have,sbook agents and are working on, on books in that way, because. Even if you look at an audience of 40,000 people, or like I have 25,000 people on my email newsletter,sthat’s such a tiny group and I’ve been friends with James clear for a long time.Since before he started James clear.com and even just watching the breakout success of like before publishing atomic habits and after publishing atomic habits. And the email newsletter was huge. It was hundreds of thousands of people when he published atomic habits. And it’s just the breakout. Well, beyond that,ssince publishing the book, because it’s a format that people understand, let’s say I read and absolutely love your newsletter, and I’ve gotten so much out of it.I’ve got so much out of your course and Christmas time comes up. There’s not an approachable way for me to get that information to friends and family that I care about. You know, you come out with the book though, and guess what? Three or four friends are getting it for Christmas. You know, any of those things, it’s such a well-known pattern.The other thing is, let’s say that,syou as a newsletter author, you’re like, you know what? I want to be on TV. Good morning, America, whatever else, like today’s show, I should do a series of things and be on TV. It’s not going to happen. You just let our creators it’s, you know, no one’s looking for them, but new author going on book tour that falls into a preset pattern wherethey’re saying like, Oh, okay,syeah, let’s get him on.Let’s have, you know, let’s have Jagger on CBS. And that is something that falls into an existing pattern because you switched media types from a newsletter to a book and they feed each other in such an incredible way.Tiago: [00:53:18] Exactly. Yeah, I I’m totally of the same mind, you know, it, it depends on your goals. Like you can build a great business, just talking to, you know, the people you can reach through your newsletter and there’s absolutely nothing wrong with that. That’s why I think it’s a personal choice.sI also know James has kind of been advising me on this whole book strategy and, you know, and he just asked me, what was the question?He said something like, you can be the coolest. The coolest kid on the block in your little internet niche, nothing wrong with that. In fact, there’s some wonderful things about that, but you just have to decide for yourself, do you want to go and, and, and influence people beyond that bubble? If you do, Nathan: [00:54:02] Yeah, that makes sense.sone of the things I want to touch on a little bit is metrics. And someone asked this,sI think Austin asked it on Twitter.sknowing what you know now, what numbers,seither for your newsletter or Twitter following or whatever. Would you be comfortable launching your first course at which you went the other way, you’ve launched courses before, you know, you necessarily had an audience. sbut how would you answer that? And then maybe follow up would be what metrics do.Tiago: [00:54:30] Yeah. And you know, I’ve, I’ve tweeted a number of times that, so that earlier ways of online courses, there were these courses on how to create courses. It was kind of like a whole genre, you know, like Pat Flynn, I think maybe as something like this, like Amy Porterfield, there was a whole generation of, of people that had the comprehensive guide to creating your own course.I really don’t think that as, as much of a fan as I am, of those people that doesn’t work anymore because the market has matured and it’d be kind of like, like, would you take a course or read a book called let’s just say courses, would you take a course on like how to run every aspect of the business?You know, in 10 hours you will learn sales and marketing and HR and operations. And like all this, it wouldn’t be credible. It wouldn’t make any sense. Yeah. Nathan: [00:55:17] That’s awesome Tiago: [00:55:19] Right. It just doesn’t work.sso I think we’re entering, we’re entering a more mature market where horses are starting to specialize like on an online course marketing online course, you know, logistics and operations, online courseNathan: [00:55:34] Unity.Tiago: [00:55:35] exactly.Nathan: [00:55:36] just how to do cohort based courses specifically, you know, so manyof those things Tiago: [00:55:44] What was, what was the question again?Nathan: [00:55:46] Yeah. Well, so the first question was,sat what stage,Tiago: [00:55:50] Oh yeah, yeah, yeah, Nathan: [00:55:51] would you become for watching a course? Tiago: [00:55:52] yeah. So here’s what I realized, you know, I’m constantly promoting the general concept of online courses and then people say, well, what do you recommend?Where’s the book or the course on how, on how to do this. And then just realized you just focus on building an audience. Building an audience is the way to launch a course or X, whatever it might be in the future, because an audience, it gives you more at-bats It’s kind of like you can, I think of it.Like you can stockpile early adopters. you have a big warehouse and you just put them in cold storage. So that the day you come out with a product, you just hit the red button and they all come to life and they’re ready to go, for whatever it is that you’re doing. And so I think I I’ve used the number 5,000.Have 5,000 people on an email list. So 5,000 people you can directly contact before I feel it’s worth the risk of putting out something that takes as much work as an online course Nathan: [00:56:47] Yep. That makes sense. And I think. I think I would quote the same number though. Something that you said about like the number of times at bat stood out to me that if you know, this online course path is something that you want to pursue or say that even just online business path, I’m realizing that I would start an online course earlier than that. seven though I think if I were asked the question, like I said, I would answer 5,000, but based on what you said, I’m like, actually, cause I don’t know, but you have to lose, let’s say I have. 50 people. If these may be a little too early, but let’s say it’s 100 people I don’t know. And I’m sitting down, am I okay?I’m going to launch a course. One, I found that it’s much easier to grow an audience for something like, for a specific product, rather than saying Oh, I’m, I’m I’m writing about productivity. You should subscribe. If you say I have what is going to be the best course on productivity. My unique take on it coming out in 45 days, sign up here to find out about it, like that tends to build momentum.And all you did was going from, you know, I’m writing about this topic to, I am producing a paid product on this topic. Oh, he must be serious.So that’s already part of it. And then, especially with this cohort-based model, you could take five people through your cohort and they would walk away. Being even happier.They’re like, dude, it was the best. There were only five people in it and I got to help him or find his material. Like we got tons of personal attention in the office hours. Like there is so much great stuff from that. And so it goes from why I did this. I put in all this work, all this stuff, different video.And I spent tens of thousands on video production, all this stuff. And no one bought it too. No, I. Put together a lot of good material and then had this initial beta or this MVP group go through it. And even if you only got three or five or 10 people,sthat would just be the first couple of times at bat.And then you’d go around, around incorporate all your learnings and go at it again.swhat do you it’s Tiago: [00:58:56] sure. Yeah. So, so a couple of things,syou’re right. The cohort-based model dramatically lowers that, that bar you have to meet to make it worth it, You don’t need to hire the film crew at being a studio, all this expensive post-production it’s just zoom calls.sthe first cohort of building a second brain was in January, 2008, 17. And it was 50 people. Just like you said, now here’s the thing I would say, though, you want to charge, you want to be premium right back then that was 500 bucks. These days it’s moralized. You can still get away with 500, but it’s more like a thousand, right? Like a thousand Nathan: [00:59:36] And what are you charging for a second brand now?Tiago: [00:59:39] Yeah. So now it’s, there’s three tiers,s1500, 3000.And. I’m sorry, wait, 1,520 505,000.sso you want to, you want to charge premium. And the reason for that is to make it a real business, to make it sustainable, and to be able to give people the attention you want. Like, that’s the thing you could charge less than say it’s just for the learning.But to raise that price later is going to be really hard, right? People are going to anchor you at whatever you say. And then every little dollar is like painful.sso let’s just say like, as a general goal, you’d want to charge 500 or a thousand,sto sell at that price point. There’s a certain conversion rate.Like I think I had a list of around 2,500 at the time to sell 50 spots. Right. So it’s 2,500 is less than I said, but, and I would agree you want a small group, maybe it would only be 20 or something, butthere’s But Nathan: [01:00:38] then you’re still pushing. You need a thousand on the list in order to,you know, if we’re, if we’re keeping similar conversionrates Tiago: [01:00:45] Exactly. There’s this weird interdependence, right? Between size price, size of list, price, and value that you, you need to kind of make sure they all support each other. I’ve seen this happen. People go, I’m going to charge, you know, 150 bucks for my cohort course. Even if you keep production value, super low, keep things very casual.Don’t have a course manager, don’t have an assistant. Th the just emotional energy it takes to, to like do the emotional labor for a group of people over a few weeks. There there’s a, there’s a level that it doesn’t go below. Like it just takes something out of you. Right?Nathan: [01:01:24] Yeah. And so if you basically say my audience is so small that I need to charge a low enough amount of money to get enough people in the cohort. We’re, we’re basically doing math, the wrong direction, a bunch of times, you know, to get that down and you’re going down the wrong train of logic, then what you end up doing is you, you charge such a low price that then it’s not.Really worth it, you know, and then you’re not as inspired and so on. So instead of a virtuous cycle, we ended up in a vicious cycle. And so that’s what I hear you saying as to why it’s like, all of that is true, but if you get at least a few thousand people that you can pitch to, then, you know, then you can charge enough that you can invest in it, that they can have a great experience at the people who buy it are really invested and are going to put in that level of effort to get a greatreturn from it.And so on. Yeah. Tiago: [01:02:17] Then you get the word of mouth, you have the profit margin to hire an assistant and later other people, you feel proud of it you You have a certain pride of ownership that you, you, you teach, not just a course, but a premium course.sthere’s, there’s definitely a flywheel where the price supports the value, the impact, which supports the word of mouth, which supports the price.So my thinking is just in that flywheel, where do you want to start? Where’s the, where’s the place to enter the fry. The flywheel that’s the best is, It’s an email list because it’s the only part that you, you can’t, you don’t need out the gate. You can just slowly accumulate over a long period of time. And given that’s the case you should make that period of time as long as possible, and get as many people on that list before starting to, to start up that flywheel.That’s that’s how I think of it.Nathan: [01:03:06] okay. So we talked a ton about newsletters and all of that. You and I have,sshowed up session and everything we just talked about.We also have a shared obsession inthe world of tiny houses, container homes, alternative living,sall of that loves to hear what you’re doing,sin the container home world and what you got, you excited about it.Tiago: [01:03:26] Yeah, this is my, my new obsession.smy brother Lucas and I earlier, I guess now last year, 2020,sdecided to start a container home building business. And it was really the culmination of 10 years of his. He had just run the gamut of the construction industry. He had started off as a. As a laborer actually,sbecome a,sproject manager, a superintendent worked for,scommercial builders,ssuper high end custom homes like in Newport beach.His biggest project was a $10 million house that he was the superintendent for the person coordinating a team of 50 people to build it.she got really tired of custom homes because. A lot of reasons, customers are very finicky, right?sany wanted to go, not modular home building. He worked for two of the top modular home builders in Southern California had various experiences with them that led him to believe that containers were the way,sand he’s, he’s gone.So, and now I’ve gone so deep into this where containers aren’t the solution to everything. I think you even responded to my tweet one timeNathan: [01:04:36] when we can get into that. Cause I.sand this is going to go very nerdy in construction.sbut forever I read cause I, I went the other way in, in built a tiny house on wheels. And then did stick frame.s whenever you say stick frame, people think that it’s like sounds,sflimsy or something it’s like, no, no, no.I just mean how houses are built, but,syou know, just did a traditionally framed construction on top of it for better installation and stuff like that. SoI’d love to hear kind of your take on it. Cause yeah, that is a Twitter exchange that we had, you know, about six months or more ago.Tiago: [01:05:14] yeah. Yeah. The idea is for a very particular type of building. So the, the homework currently building, which is our first client is a good example. It’s a, it’s this nonprofit called creator cabins.sand the idea is to have a creative retreat center.sJonathan, who’s our partner on it has a property outside of Austin and he wants to do two things, conserve the land, which is beautiful and has some amazing nature and create a place that creative people can go out and just have a, either a retreat or do a place to focus.Right? So if you look at his requirements, you know, one of them is you have to just deliver it. It’s it’s conserved land. He doesn’t want all these contractors coming in and out, like creating all this footprint.sso it’s, it’s just a, it’s a one day installation. We’re gonna install from beginning to end a 1200 plus square foot house in a single day easily.And that’sjust from a, from a conservation point of view. It’s prettycool Nathan: [01:06:15] So how many, howmany containersis that? Is that four or fivecontainers?Okay. Nice. And so those are going to be built in somewhere nearby in Austin or shipped in from a away Tiago: [01:06:29] They’re being built. It we’re almost finished. We’re going to finish in the next couple of weeks,sin Southern California. So, so this is the crazy thing, Nathan. And actually this might be the connection to the, to the theme of, of the other podcasts.sthere’s kind of a crazy hypothesis here, which is that home building is becoming a remote work industry.If we use these modular techniques, right. That there there’s a yard and it’s just, it’s an empty lot. There’s maybe a source of power and that’s it. There’s not even a bathroom in Redlands, California, that my brother is building the, and we just posted a video. If you go to the Fort shelter, YouTube channel, and you can see a 62nd clip of this,she’s almost done building these, these four containers and then he’s just going to ship them across country in a convoy of,sNot even semis you, you Nathan: [01:07:24] Okay. Huh? And so, yeah, I’d love one thing that I’m fascinated with. And actually, I think maybe you and I both got tagged in it in a thread a while ago of people taking internet businesses and doing something else with it. Like there’s someone I’m spacing on his name, who I think of it, Allen,she started a business called less counting.He lives out in Panama city, Florida, and he. Built SAS company sold it, all of that. And he basically took all of his money from it and has been investing really heavily into his own community in downtown. He’s been buying buildings and renovating them and all this stuff. So I’ve been fascinated by people who are like taking internet money and turning it into like real, tangible things.And that’s something that I do have,swe, we operate a bunch of Airbnbs and the next few days I’ll get a signed deal on another, another building and all that. But.sI’d love to hear, like, is this something that you’re funding out of, you know, your revenue from courses and all of that.Yeah. Tiago: [01:08:31] Yeah.sfunding. I think that trend, you mentioned, we’re going to see more and more. I mean, it’s already happening in a big way. Just not maybe publicize as a trend. But,sthere’s this, I think this desire to, to, to diversify, to have more concrete assets, like it’s, it’s kind of funny, like on the internet, we feel so secure because, Oh, we’re not vulnerable to COVID and all these things, but when you look at the stack that we depend on how many layers of abstraction, it’s kind of insane that we have any sense of security.Nathan: [01:09:02] Yeah, well, along well along those lines, I mean, I don’t think I’m actually going to. Get to this point, but my wife and I were talking well, no, I guess, I guess it will come pretty soon. Well, we make a lot of money from convert and all that. We live fairly conservative lives as far as spending and, and,sthat kind of thing.And pretty soon we’ll be at the point where revenue from this Airbnb business will cover all of our expenses as a family. And it’s kind of what you’re talking about. Like I don’t reasonably expect that I will ever need like, get into a situation where it’s like, Oh, I don’t make money on the internet anymore.I have to make money from Airbnb’s on our farm, you know, and from other properties beyond, but it’s also kind of fun to get to the point where you’re like, but I could, like, those numbers have balanced out where I’m now diversified in this thing. And. Tiago: [01:09:56] exactly. I think with the events of just this week,smore people are thinking about that than ever.sand so the idea was,swas he out to fund the business? And also just from a, like a family point of view, I just looked at my nephew, my brother’s son, his name is Luke, and he’s just incredible kids, just so cute, so innocent.And I just thought, I can’t think of any bigger impact, bigger, positive impact on his life than having his dad have his independence. You know, I’d watched my brother over the course of 10 years work so hard for this series of builders. Never be treated that well, never have his, his knowledge fully appreciated work, long hours.Like, you know, most of us do. And he likes working. You know, we, we both share that we love our work, but there’s something with the flexibility taking a day off when you really need to, you know, sleeping in when you’re just that tired,sbeing there for the, just the, the events of the family that is priceless.And so when I looked at the, the funds we were making from our business, I thought I could invest in it in all sorts of things, but I want to invest in my family because what else matters like this, this is the kind of stuff that really matters. And so,sreally was the opportunity to make a lifelong dream of his, and actually an interest that I share, like modularity is actually a fascinating concept that relates to knowledge that relates to productivity that relates to online business.I kind of, it’s kind of like my, my,sMy S my other motive for doing this is to understand how something like physical space can be turned into units. And those units can be combined like Lego blocks to build whatever kind of space, whether it’s a full-size family home, like we’re building now or a home office.Like with COVID starting there’s this whole other opportunity. Like, I can’t imagine what the demand for a backyard container sized home office is now, or will soon be like this isn’t going away. This work from home situation. So that might be the second product line is,is a line of home office.Nathan: [01:12:03] Yeah, I believe it. When I’m in, I’m sitting in a tiny house home office right now, you know that,sit’s great. You walk across the backyard, you know, you could go. The thing that you said about family, there’s twoaspects of it that really resonated with me. One is there’s sort of this unique set of skills that I think we understand in order to do online business.One of them is leverage, you know, with the leverage of an audience at the leverage of good marketing, branding, storytelling, all of these things that we’ve brought into play. It’s not necessarily a harder or a better skill or anything else than construction or something else. It’s just, the market just happens to reward it really well.And so that’s one side of it. And so being able to partner with someone like your brother, in my case, I’m partnering with my good friend, Patrick, who has worked construction for a long time and, and hasn’t ever had leverage in.sin his work. And so to be able to combine his incredible building experience with my knowledge of how to get leverage and capital and marketing and everything else is like, Oh, this is, this is perfect.And then theother sideis just from the perspective of, of kids like you and I both have kids now.smine are a little bit older. My kids are nine, six, and then one and. They’re not, it’s going to be a long time before they’re going to understand what, what convert kit is, what I do, any of that.sbut the Airbnb, our little guest house that we went out on Airbnb, they get that and they understand the mechanics behind it and I pay them to help clean it.And, you know, that’s something that we do together.sor like when we bought a fourplex and got that put on an Airbnb.Even though it would be far more efficient to just, I don’t know. I don’t think so. Task rabbit here in Boise, but you know, to pay someone on task rabbit to go and assemble all the furniture and set the up, we got together, you know,smy wife,sand our kids, and then our friend Patrick and his kids.And we all went over there and spent like a Saturday just doing this thing because it’s a, it’s a business and something that they can understand. And, you know, we’re assembling furniture and like getting the TV to work and like building up this whole part.sbecause I want to show them, this is like, this is a bit business.This is how it works. And they get that in a way. Okay. So we pay for this once and then people pay us to stay every single night and the kids are like, wait, they pay how much. You know, and it like, even if it’s a hundred bucks a night, they’re blown away a hundred dollars. It’s an incredible thing, you know?And so they’re getting this firsthand example in business that if you’re like, no, you don’t understand. So you sell this course for 3,500 cohort, basically, you know, like maybe by the time 15 or 16, they’ll understand like the true details of that. But,sso I just love. Taking,sthe resources that we have and the marketing knowledge and everything else and applying it to businesses that, sfamily can be really.Tiago: [01:15:14] that’s. That’s beautiful. That’s wow. I had never thought of that. Maybe just cause my, my kid is fresh out the oven, but that is true. That is very true. Yeah. How are they going to learn those bread and butter principles and lessons if they, you know, which they need to learn when they’re, they’re pretty young to sink in. sif, if we’re doing work that is quite complex,Nathan: [01:15:43] Yeah, I think so.s I’m I’m curious what.just to kind of wrap up that conversation. What does the next year or two look like for Fort shelter?Tiago: [01:15:52] So we’re finishing up the single family home. We’re going to ship it out to Austin.sthen in a few weeks, we’re actually going to go to the tag in convert kit, which is interest colon for shelter,swhich is being added to every day. This is, this is the insane thing. You know, I have a couple of blog posts.With forms when people’s put in their email address, they get added to the,sto the list. I think I also have a form on, on my brother’s main website. So every time I look at it, it has a few dozen more people. I think it’s up to above 500. Nathan: [01:16:24] I’ll just say that I first joined your list for the Fort Tiago: [01:16:27] There you Nathan: [01:16:28] Like I wasn’t onyour list before. And I was like, Oh, I’ll try to learn more about this. And then I was like, Oh, now I’m also on the rest of Jagger’s list That’s great Tiago: [01:16:37] It’s like, it’s like, there’s a stadium, there’s many doors to the stadium. So some people come for the hot dogs. Some people have come for the, you know, the performance. Some people come to their friends or are, are there. And then seeing you have this big, this big audience. sso we’re just going to, this is kind of the way I do everything is like build up the interest list, start learning from them. So we’ll send them a survey, capture their interests, have a series of interviews, do a Q and a call.sand then once we, once we figured out we know exactly what they want or can perfectly meet the needs of a small group, we’ll Nathan: [01:17:17] Which is,suh, you’re just now shipping a container at somebody, which is a different, different world than delivering on the course, but, but you’re right. The sales process and all of that is, is pretty similar.Tiago: [01:17:28] yeah, I think this is kind of related to the idea of people buying real estate. I think the margins and the profitability of online stuff is so great and the overhead is so low that it, then it then makes other kinds of businesses that you normally wouldn’t enter attractive.Like another project we’re doing is we live in long beach, California. We’re going to be,sopening a dance studio. I hear locally. There’s so much amazing commercial space. Now that’s just completely empty. And when you look at the economics of a dance studio, there are daunting. Like people don’t start dance studios to make money.You know, it’s really tough.sbut with the online business, as long as we break, even, that’s what I’ve told Lauren, my wife, who’s going to be spearheading it. Cause she grew up with this dance studio as the foundation of her community. She, she grew up in it. You know, and so as long as she can break, even within a year or two and pay the bills, it doesn’t need to make money because we can offset the differentsources of revenue.Nathan: [01:18:26] Hmm. I love that something else I’m realizing that I probably haven’t shared with,sany listeners before, is that part of the impetus for starting ConvertKit? Is that, and so this is, let’s say you go back to 2012. I had just had a few successful initial. Like book launches. We’rejust starting attractionwith the online audience.When I said, I want to do ConvertKit as well was I wanted recurring revenue and specifically 5,000 a month, because that would cover all of our expenses because my wife and I wanted to start a coffee shop. And I knew that a coffee shop is a terrible business and that I didn’t want to have to make a coffee shop profitable enough that we could then pay all our bills off of it.And that sounded really, really stressful. And so then I said, okay, If we had a software company or some recurring product that was making $5,000 a month as a starting point, then up from there that would pay our bills. And then,syou know, we can have this, this in-person business and this scholarship business that,sit could be so much less stressful because it’s not trying to be profitable and pay the mortgage and everything else.And we ultimately decided that we want to do a farm instead of a coffee shop, but, you know, it’s the same principle Tiago: [01:19:40] there you go. We’re we’re fusing the online and offline worlds into just one,one integrated whole.Nathan: [01:19:47] Yep. That’s right. Well, this was fun. Thanks for taking so much time to, to chat through newsletters and everything else. swhere should people go to subscribe to your newsletter and, and follow what you’re doing online?Tiago: [01:19:59] Yeah. Been a pleasure, Nathan. Thank you. All my stuff is on my website, which is Forte Labs, fortelabs.co, not .com, just .co. And if you just add a /blog, you’ll find all of my writing going back six, seven years. And that is really everything I know. So happy to answer questions on Twitter (@fortelabs), is my most common platform, but if you do a search on my blog, you’ll probably get a much more eloquent answer.Nathan: [01:20:26] That sounds good. Well, thanks for hanging out 

Lenny Rachitsky sold his company to Airbnb years ago and he spent a bunch of time there as a product manager, working on growth.Now Lenny’s full-time job is his simply-titled “Lenny’s Newsletter”, where he shares everything he’s learned about building products and teams. With over 3,200 paying subscribers, Lenny’s Newsletter brings him a larger income than he had at his tech job!In this fun interview, Lenny shares his journey—how he went from wanting to found another startup to being a one-man newsletter business, and the lessons he’s learned along the way.You’ll learn the “value-add” for a paid newsletter that’s been a great success for Lenny, and how he’s avoiding the trap of workaholism as he builds his business.Lenny also shares how he never runs out of topics, and how he stays interested and curious so he can enjoy running his newsletter for years to come.Plus, as popular as paid newsletters are, they come with some important downsides! Lenny reports from the trenches on what they are and how to deal with them.Links & Resources Airbnb Coda - A new doc for teams. Why a Paid Newsletter Won’t Be Enough Money for Most Writers (And That’s Fine): The Multi-SKU Creator - Hunter Walk Lenny Rachitsky’s Links Sign up for Lenny’s Newsletter Twitter: @LennySan LinkedIn: Lenny Rachitsky Episode TranscriptLenny: [00:00:00] I find there’s any time not spent creating high quality content is not time well spent over the long run. It’s all about just valuable content. You know, if you provide value to people, they’re going to want it and they’re going to subscribe and follow and pay.Nathan: [00:00:18] Today’s interview is with Lenny Rachitsky. Lenny’s company was acquired by Airbnb more than seven years ago. He spent a bunch of time at Airbnb as a product manager, working on growth, where he became fascinated with things like, how do you manage a team? How do you grow a company? What are the product management best practices?All of these things after leaving Airbnb, he started a newsletter just called Lenny’s Newsletter, and it now has over 3,200 paying subscribers. he’s now earning more from his newsletter than he was at his tech job. Quite a bit more actually. And we get into so many things, but how to keep writing newsletter really fun, how to grow and scale your audience using guest posts to get those first subscribers so much good stuff.Let’s dive in. Lenny. Thanks for joining me today. Thanks for having me. So you actually kicked off our call and kind of a fun spot. So I want to start the interview there. And that was, you just said, so did you read the New Yorker article, you know, and, the New Yorker just did another article about newsletters.Why don’t you give us a high level? Cause it kind of takes us into the state of newsletters, you know, on the web right now. Lenny: [00:01:28] Oh, so I find, I generally try to avoid pontificating on the state of media and newsletters, because I feel like that’s not my depth. There’s a lot of newsletter writers that like come from media, I’ve thought about, you know, this whole space of newsletters for a long time.And it’s fun to think about it and talk about, and, and tweet about sometimes. But yeah, I don’t have the most thorough opinions of the whole industry, but. What I find is when people do this kind of like overview of what’s happening, it’s always this interesting combination of like, Oh, here’s all the good elements.People can write whatever they want. And they have freedom. They’re running their own business and creating their own kind of life. And then there’s like, Oh, but all these dangers, what are they, what’s going to happen? They need health insurance. And how do we moderate all these folks? And who’s going to win.And how do you, how do you not create this? Just like 1% that does well. And so, so the post is kind of essentially going through a bunch of stories of all those things happening. And I think the conclusion as always, as it’s complicated and there’s good and bad end, we’ll see where it all goes. Nathan: [00:02:32] Yeah.It’s been fascinating to watch how the landscape has changed over the last, you know, seven or eight years since I’ve been working in this space. But you know, particularly the last say 18 months as Substack has gained a ton of traction. I think a lot of people, this is kinda what I want to talk about next.Who maybe in the past would look at newsletters and go, that’s an interesting business. Like that’s a thing. Maybe that’s your lifestyle business. I don’t know I’m going to go do a startup, you know? that was all the mindset. And now Lenny: [00:03:05] that’s exactly what I did. That was my whole plan is start a company.And then I started this newsletter on the side just to like play around with something and magically, it turned around and the newsletter became the main thing that I do. Nathan: [00:03:16] Yeah. So let’s talk about that more. Cause you spent what? Seven, eight years at Airbnb working on, on growth and product management. and so I’d love to hear, well, let’s see, let’s talk about just the transition out of Airbnb and then what was next?Lenny: [00:03:34] Yeah, so I left Airbnb about a year and a half ago. Last March. I was there for seven years, sold my company to them and. My plan a, when I left, first of all, I had no real plan. I was just like, I need to, I need to do something different. I need to move on to some new, and so plan a was, likely start a company again.Plan B was maybe do some advising consulting plan C was maybe join a startup plan. D was maybe join a big company. And now are on those lists of plans that I have make a living off writing a newsletter. But what started happening is I first started collecting my thoughts of what I learned at Airbnb and things I’ve done in the past, just so that I don’t have to relearn them.When I start a company is I put out medi posts and that did shockingly well, and then I put out a few more medi posts and those did well. And then somebody suggested I switched to sub stack to, you know, to the classic reasons to have your newsletter it’s own your audience, to not give all the benefits and medi and those kinds of things, which we can talk about.And that just kept going well. And it was always a side project that everyone around me was like, okay, stop this writing thing you’re doing. And you really want to do a startup. You should really focus on that. And just spending so much time writing, what are you doing? But I just kept doing it cause it was interesting and fun and people seem to value it.And I had a good conversation with a friend, maybe six months into it. And his advice was okay, this seems to be working well. People seem to value it. You seem to enjoy it. Maybe just try that for a little while longer. And don’t put all this pressure on yourself to start a company now. And so I did that and it just kept growing.And eventually, this year actually around COVID beginnings of COVID, it was like a year since I left my job. I had no income. I didn’t know what I was going to do. All my stock is down. I didn’t know how I was going to make money again. And so I decided, let me try this pate version of the newsletter and.And that kind of took things to the next level. And now we’re here where I’m making a lot more than I made it Airbnb. And I don’t have any future plans beyond this. Nathan: [00:05:38] Yeah. So did you, figure out what the start-up was going to be, or was it still, you were playing around with ideas and the newsletter was a playground to try out or to like think through some of the things you were considering.Lenny: [00:05:51] Newsletter is more of a playground of collecting things that I’ve learned that I wanted to crystallize, you know, as they say, I don’t know what I think until I’ve written it down. And I was, it was an excuse to crystallize things that I’ve learned over the past. but in terms of the startup, I had, I had a spreadsheet of 50 ideas that I was working through one by one prototyping, asking friends, trying to research them.So as, as, as I went through like 10 of them, by the time I stopped. And, none of them, none of them really stuck. That was part of it is I didn’t find anything that was, “Oh shit! I really need to stop everything and do this thing.” if I, maybe if I had it, it would have been some different, but startups are hard.It’s like a hard life to pursue. And so I’m happy not to do that right now. Nathan: [00:06:33] They are. They’re very hard. And especially that, I don’t know those first two years or three years, you know, before it gets a team in moment it. It just it’s really hard. So, so at that initial traction, that point where you’re like, Hey, this is working.What were those signs that you look for? How was it a nber of subscribers or was it just moment a rate of growth? What was it? Lenny: [00:06:58] I’d say early on, it was very qualitative. I just kept getting these really nice messages from people about how valuable some of the stuff I’d written had been. So is that plus continued growth.People just continue to subscribe and come back and not unsubscribe. That was a good sign. and then, yeah, I guess it was those two things, qualitative feedback and just growth continue to happen, even when I wasn’t doing anything. And also the feedback was coming from really smart, successful people that I really respected, so that added to it.Nathan: [00:07:33] So those things, I think what’s interesting about that is that. It has you focusing on the quality of the content rather than the results.Lenny: [00:07:41] Absolutely. That’s what I find over and over again. Anything that I do, that’s not just create high quality content does very little for the success of the newsletter.I find there’s any time not spent creating high quality content is not time well spent. I just keep finding it over and over. I tried like Twitter ads. I tried a referral program. I tried, cross-promotion across newsletters and none of that really did anything. Although initially there were some things that, that I did that were really impactful to help jpstart it, which we could talk about.But, but over the long run, it’s all about just valuable content. And, you know, it’s like if you provide value to people, they’re going to want it and they’re gonna subscribe and follow and pay. So the more you could just provide value, the more successful you’ll be. And that’s what I keep finding. Nathan: [00:08:28] When I think another thing in that is.The type of people that you’re writing to. So you’re looking at a lot of that qualitative feedback was from people that you really respected, you know, whether it’s industry peers or others. And I find that when I’m writing to someone, who’s one of my peers, the quality of my writing is so much better. If I even have this in mind of like, okay, this didn’t happen, but let’s say this person asked me for advice on how to get your startup to your first 5 million ARR.You know, then if I write to them, it’s just better. Right. And then I think like reading a lot of your early stuff and even the way that you write today, I get that feeling from it of like, Oh, this feels like it’s written to Lenny’s peers and his friends rather than from the place on high, where Lenny that, you know, Yeah, the startup expert is writing to the masses because it just, it comes through in your writing in a different way.Yeah. Lenny: [00:09:26] Yeah. And I think a lot of that comes from, I don’t know if insecurity is the right word, but I just, I don’t feel like I have the answers and I’m not the smartest, most successful person. And so my lens is how do I just give you on arguably correct advice that either comes from successful, smart people or a bunch of analysis over what’s worked or.Or something like that. So, so the lens I use isn’t I know a lot of people and I like your framework of just like pick a person and a specific person in my end, right. To them. I use it more like a broad lens of if I’m like a founder reading, this is this like actually useful to me or is this just like a bunch of fluffy stuff?That sounds nice that I can, I’m going to just forget immediately. And so I always come back to you as, as concretely. Actionably valuable immediately to somebody. And if it’s not, then I refine it further and cut out stuff. That’s not actually useful. Nathan: [00:10:17] Yep. That makes sense. What were some of those things that worked for the early on that you were talking about to get the initial growth?Lenny: [00:10:24] So, so I started, I started at zero is everyone starts with, and what I, the way I first launched the newsletter was actually on Twitter and kind of like, it kind of created this interesting back and forth between medi and Twitter and sub stack. So I wrote that first piece on medi and it got like featured by medi.The, it was about Airbnb. What I learned at Airbnb, the CEO of Airbnb sent it out to the entire company and it got into this collection. So it just got a ton of use. And that led to some Twitter following. Somehow, they kind of found me on Twitter. And then as I was reading, you have much of a Twitter following.Not really. I had, I had like a few thousand followers, something like that, which is not from Nathan: [00:11:06] being on Twitter for Lenny: [00:11:07] years and yeah, exactly. Yeah. Yep. Which is, you know, some people have less than a thousand, so that’s a different place to start. And I’ll also add, I’ve never like focused on Twitter followers.I was just like, how do I share valuable things with people? Cause I just want to get it out of my head. And so that was, as I was writing these medi posts, I was also tweeting little nuggets of things that either were in that post or just couldn’t make it into a whole post. So I started just kind of doing both things, tweeting and medi posting and that built up the Twitter audience just because some of the stuff was proved to be really valuable.And then when I launched the sub stack, I basically just tweeted out, Hey, I’m launching a sub stack newsletter. You should subscribe. I don’t know what it’s going to be at, but it don’t miss it. And so that got me to my first few hundred subscribers, just like tweeting about it. And I had maybe like 10,000 followers at that point, something like that.And then, and then I did a couple of guest posts, one on Andrew Chen’s blog and one on the first round review. And that it’s a tweet Twitter. Plus those two got me to the first thousand, essentially. Plus in that time, maybe like 20 actual posts that were valuable enough for people, right? Nathan: [00:12:22] Yeah. Is guest posting something that you would recommend for someone I’d Lenny: [00:12:26] say?Yeah, I’d say initially when it’s early, for sure. Because if you think about just marketing anything, you just want to go to where your audience is. And if you can write something that in a place somebody already has that whole audience and. Show how awesome you are. They’re going to come follow you wherever you are.So I find it, I found it to be super valuable, but you have to just pick the right blogs and newsletters and do a great job. Nathan: [00:12:54] Yeah. That’s I mean, in the early days of my newsletter, maybe after I had it with 2000 subscribers, a thousand, 2000, somewhere in there, I started doing guest posting pretty heavily.And it’s exactly what you said. Like some people think about guest posting as like, Oh yeah. Here’s this thing that. I wouldn’t put it on my blog, but sure. I’ll try to see if you want to run it. It’s not an effective strategy instead of you’re like, here’s the best content that I wrote, like, et cetera, writing one, an article versus specialty magazine, which is a web design Lenny: [00:13:24] and development.My wife’s been in that. Oh, Nathan: [00:13:26] nice. Yeah, she’s a designer. Yup. and I read them a lot and so I wrote a post on product launches. That was 4,000 words, long, all kinds of detail, everything, you know, I tried to put as many real nbers in there as possible. And just try and be like, this is everything I’ve got, you know, and that post, I think got me, well, had a great call to action for like sign up for a free email course at the end that I had, like, here’s a ton of great value.And then if you want even more like in the weeds, nerdy stuff, he, you know, he here’s even more. And that picked up like 2000 email subscribers from a single post, which at the time, you know, we’re like, 50% ground, you know, it’s, it’s pretty amazing to thousands of them a lot. Yeah. But even if at that stage, if you’re getting a hundred or, or 300, like that’s totally worth it.Lenny: [00:14:15] Yeah. Similarly to the one I did with Andrew, I worked on it for like months. It was a 28 ways to grow supply in the marketplace. And I had like all these examples and, and quotes and all these things and I showed it to him cause we got to know each other a little bit on Twitter and he’s just like, and I republish this on my blog.I’m like, Well, can I also publish it of mine? It’s like, let’s do a 24 hour exclusive. And it was a really tough call cause I was really proud of it as the best thing I’d written up to that point. But again, it, I think that’s why it worked because it was high quality. Nathan: [00:14:47] Th the exclusive is interesting because it still gets out to your audience, but it leads over there.Lenny: [00:14:53] yeah, they’re not, they’re not as into that. They don’t want you to republish it at any point. Nathan: [00:14:59] Yeah. And the, I mean, they’ve got quite a content strategy and Lenny: [00:15:02] yeah, they’re amazing. I’ll give you an editor. It’s amazing. Nathan: [00:15:05] Yeah. So it’s guest posting something that you’ve continued to do, or is that more for initial traction and then just focus on your own property?I’ve done Lenny: [00:15:14] that a couple of times. I did a couple more first round pieces actually, now that I think about it, but it was more just, it felt good. It wasn’t. It didn’t really do much honestly directly, but you know, all these things add up. But what I find now is that now that I have a meaningful audience, I can promote other people through guest posts, which one people come to me to try to do that, which is really funny.And then on the other hand, it saves me work because I get this amazing content from someone. Great. for a week because with a paid newsletter after right every week forever, and the more amazing pieces of content I can create that I don’t have to write myself the better. So, Oh, it was a balance obviously, but what I try to do is collect just like the best people in each field and have them write and definitive answer on a topic that people are asking me about.And so it’s kind of flipped now, which is kind of interesting Nathan: [00:16:06] when I think having the. Well, you, you basically set the bar for the content and then you’ve said, If anyone in the industry who’s really experienced can meet that bar or exceed that bar. Then I would love to have you. And then it’s, it’s not a like, Oh man, this article is not from lending this week.It’s from some random person it’s instead like, Whoa, I can’t believe Lenny got this person to come on and share this level of detail. Lenny: [00:16:31] Yeah. And here’s a rule of thb I’ll share is if someone reaches out to me to try to do a guest post. That automatically means they’re not going to do a guest post. I have to go reach out to them because I find that the people that I want to do the guest poster, often the ones that aren’t interested in doing one.Nathan: [00:16:49] Right. Have you ever had, I had someone who reached out to you do a guest post that like met the bar for quality and was really good? Lenny: [00:16:56] Not yet. Okay. I’m sure it’ll happen, but I wonder. Nathan: [00:17:01] So I’m just spit balling here. I wonder, like I’m saying, if I were to pitch you on a guest post, like if I was listening to this and heard like Lenny doesn’t take outside pitches, if I were to be like, yes, but he hasn’t seen my content.What I would do is I would pitch you with the entire article pre-written and I would say, okay, but. You know, what about this? Do you think that Lenny: [00:17:23] would work? Oh, that would definitely work better because I find that once I get started with someone, it’s hard to just, if I find that it’s not great, it’s hard to be like, no, nevermind.So yeah, the more I can see where you’re going to land, the more likely it is to work out. And what I find is often with even the most amazing people, there’s a bunch of back and forth, right. Push them to make it more concrete and more actionable. And more tactical. So, so I, I love seeing the draft cause then I can see how far it is from something that’s going to be amazing.Nathan: [00:17:53] Right. And you can see immediately if, if this is an idea that’s been played out and done plenty of times before, or if you’re like, it’s not good yet, but I bet if you change it. Exactly. Lenny: [00:18:03] Yeah. It could be. Yeah. There you go. There’s a, there’s a good Nathan: [00:18:06] trick. And so, I mean, we can carry that forward, right. If even someone who, doesn’t often take guest, I mean, it’s, it’s basically.It’s similar to what you did with, Andrew of you didn’t pitch him, but you said, Hey, I’m working on this. I don’t know. I don’t know exactly what you said, but I’m working on this. Can you give me feedback? Can you give me ideas? and then he’s like, not only that, but can I run it on my, on my site?Lenny: [00:18:32] That’s exactly right. And actually the first round, it was the same way I had kind of the outline in a lot of the posts and I showed it to them and that got them excited. Nathan: [00:18:40] Somebody who did this really well, And I feel bad that I’m spacing on his name right now, but who runs groove, groove, hq.com. they built a really, really popular blog on their journey going to 500 K.now I’m trying to think of 500. I’m trying to think what the nber is anyway. It’s a lot of subscribers. no, sorry. It was on the, for their software product. Maybe they’re trying to get to 5 million, 5 million ARR or something like that. They had some. It’s was probably 500 K of MRR is what, the nber they’re turning.Cause I remember looking up to it being like convert your wasn’t at that level. And I was like, Oh, that would be cool to get there. You know? and something that he did really well is have a content like a sort of an advisor group. Where he basically reached out to a bunch of smart people and said, Hey, I’m going to write stuff on these topics.Would you mind if I sent you a draft of it from time to time for you to look over it? If I think it’s particularly relevant to you? and I think that can work well because, so he looked me in on that and I was like, yeah, you’re writing great stuff. I’d love to see it before it’s published. And maybe you share some tips or insights.yet he’d been shot plenty of other people. And then what happens is when he would then publish the piece, he would email the same group and it was probably 20 people or something and say, Hey, thanks for your help on this adhere to his life. And then I’d see all those people tweeting about it and sharing about it because they had like a, an emotional, or they had an investment in him and his success.Lenny: [00:20:13] That’s actually something I forgot to mention that I found really effective when I launched, when I launched the paid plan is I did exactly that with my launch announcement and ran it by folks like Andrew Chan and, and a bunch of other people with a large Twitter following, like generally to get their feedback on how to frame the announcement.Cause there were supporters along the way and then also led to them, tweeting about it. And that helped a lot. Yeah, that Nathan: [00:20:39] makes sense. Well, let’s turn to page. What made you choose a paid newsletter as the business model compared to, you know, many of the other ways that you could earn a living in, in startups or from a newsletter Lenny: [00:20:51] first?I’ll say that it there’s a lot of downsides to going pay that I didn’t think about until I went paid one being you’re, like I said, you’re stuck writing every week. Some people do it daily. I don’t know how they do that. It’s blows my mind. but you’re basically stuck doing it for I in theory, forever because people are paying you these annual plans and I don’t, I stop unless you just shut it all down and just refund everybody their money, which is hard to do psychologically.So that’s one is you just kind of have to be ready to do this for a long time. You know, maybe if it’s like a few years and you can just move on, that’s probably fine, but you can’t stop. You know, in a few months. So for me, it took nine months to get from starting the free newsletter to switching, to paid.And a lot of that was building confidence that I could keep this up. And I had a topic every week that I could write about that I was excited about. So that’s the reason that it’s, it’s something to think about the other is before I wrote every week and it was totally free to everyone. And then once I flipped the switch, I’m doing the same amount of work, but almost all of it is not hidden behind a paywall.And it just feels really bad. Like just like man doing all this work and no one’s going to see it. Cause initially you have very few paying subscribers and it’s just like, feels like it goes into a black hole. And if, kind of get used to that of just like, well, I’m getting paid, people are paying for it.That’s the benefit. And that’s the, that’s the cost of writing this and doing all that work. So, but that like, I dunno, like, like it feels like an obvious thing, but feel the feeling of it. It doesn’t feel good, but it all, it all works out. Nathan: [00:22:24] Yeah. Digging in on that. How have you found, like your writing process and like that showing up really consistently and the pressure of needing to publish could feel like a hamster wheel.It could also be turned into a system. And so one of I’d love to hear anything that you’ve done to establish your process, to bring it from like hamster wheel to a reliable, you know, productive system or if that’s even happened. Yeah, Lenny: [00:22:53] totally. And if we want, we can come back to the paid, the launching of paid.so, so in terms of my process very much the way I describe it, as it feels like a, Boulder’s always chasing me in, as soon as I’m done with one week, there’s just like the next one’s coming. And I have to always plan ahead and it’s a real thing and it’s used to be stressful, but now that I’ve done it long enough, I, I, it’s, again, kind of the confidence where I’m like, okay, I’ve done this for like a year and a half now.I’m not worried. I’m not going to find something great this week. But what I’ve done now is, I basically have three months of ideas mapped out. So I have a Coda doc where I have every topic kind of on its own page, kind of mapped out for the next three months, roughly just like the topic is the headline.And then for the more eminent posts, I’ve I basically go in there and just flush out with bullet points initially, just like the things I want to say and thoughts that I have as I think about it. And then as it, and then for the next like month, I go deeper. So it’s kind of this like spectr of depth the next few months, the what’s cool about the format that I happened upon is, is it’s an advice coln.And so that means people send me questions that they’re tackling in real life. And so I have this large backlog of. Really great questions from founders and product managers and growth people. So I’m finding, I’m never going to run out of things to write about at this point. And if I do, I could just go back and do better on things that have already written up.So the topics don’t seem to be a problem, but then actually delivering high quality stuff every week for sure is a challenge. What helps one is just thinking a little bit ahead. So. So I’m trying to, I always try to be like a few weeks ahead of like done content, but I never actually get there. So it’s usually like the next post is like 80% done a week ahead of time.And then the rest are like 20 to 10% done. And then the rest are just headlines. and otherwise it’s just making time to write. I block out my morning site. I have no meetings until 3:00 PM. That’s my new rule that helps a lot. And it’s hard to do if you have a day job and. That just always comes back to, no, you can’t do this.If you have a day job, I don’t know how people have a newsletter. That’s good with a job. And that’s the secret is I have time to do this stuff. And most people don’t like, I don’t know how you do it. Newsletter having running a company. Nathan: [00:25:13] Well, I mean, I do a lot of what you’re talking about of like, yeah, this will totally be done for this week.And then you were like, wait, I said my newsletter every Tuesday and, yeah, I don’t know with Tuesdays, but it sounded good. Someone Lenny: [00:25:25] said it, it was the best data send for open rates and Nathan: [00:25:28] now it’s stuck. I think it’s that I don’t want to be in the Monday morning inbox. and so that, but I don’t also want to be at Friday end of the week.And so I’m like Tuesday, you Lenny: [00:25:39] guys, you guys must have data on which day of the week is the highest open rates. It’s Nathan: [00:25:42] Tuesday.not so much definitive, like it, it’s not like wildly, you know? but, but Tuesdays are good and Lenny: [00:25:55] shout every, every percentage Nathan: [00:25:56] we can get. Yes, exactly. And that’s, you know, we send a little over a billion emails a month, so we have a good amount of it can amount of data that Lenny: [00:26:04] we, you heard it here first Tuesdays.Yeah, Nathan: [00:26:06] exactly. So on, let’s see, Oh, with the content coming out, that’s something that I always run into. Like I was actually going to send a year in review posts tomorrow Lenny: [00:26:17] and that’s what I’m doing. Nathan: [00:26:19] Yeah. But it’s not done, you know? And I was like, Oh, it’s end of the day, Monday. And that’s not going to happen between now and then.And so I have basically the same process that you do of like, this is what’s coming. And then here’s the ideas. And, and dripped out from there. something else that you mentioned that I thought is a really good point is the asking. It’s not well asking your audience questions and then asking them to submit your questions.So one is the generic, like, Hey, if you have any questions about these three topics, like ask why, or even if you said something like, Hey, I’m going to write about freemi a freemi business models in a couple of weeks, like submit your stories, or like you can solicit that kind of thing. Especially once you get past.Maybe two or 3000 engaged subscribers, then you start to get a good nber of things there. But then the other thing that I love is to ask, Hey, what’s your biggest frustration related to life as a product manager, you know, running a freelance business, like whatever the topic is for your newsletter.and that can get a lot of good things where, you know, people will come in and say like, You know, here’s my frustration. And you’re like, Oh, let me tell you how to solve that. And that’s the writing prompt that you were looking for to take an idea actually all the way through? Lenny: [00:27:36] Yeah. I think that I kind of made my newsletter, like I leaned into that even more and it’s just like, this is purely an advice coln.Same your questions, anything you’re dealing with that, that stresses you out at the office or around product or growth or managing hans. And so at least a lot of really good questions because they’re very, they always end up being very real, like stuff they’re actually dealing with. And I wish I could answer them all, but it just piles up.And so I have to pick one. And the other thing I have to think about, cause my newsletter has this broad spectr of product management and growth and startup stuff. And people management people join me with different, hopes and dreams for what the newsletter’s going to be. So I have to balance out all these different types of content every week.So it’s a weekly newsletter, so I kind of have to do. A nice balance. I can’t have like three product posts in a row. Cause then all the growth people are going to leave. And so that’s something I have to think about. Yeah. Do Nathan: [00:28:28] you see, is that a fear that you have, or is that, does that actually manifest in the nbers as well?Lenny: [00:28:33] It’s hard to see the nbers. I definitely find people on subscribe, but they’re just like, nah, not what I thought it was going to be I’m out, but I don’t know what the root causes and it’s all anecdotal, but I do. It just feels like that’s probably what’s happening is they’re just like, I don’t care about growth, stop talking about growth, Nathan: [00:28:52] right?Yeah. And you get both sides of it where someone comes in from the greatest article they’ve ever read on growth. They’re like, Oh man, this is all he ever talks about. It’s incredible. And then other person comes in from the same side on a product management. Or people management or whatever. And they each think that you talk about something.Lenny: [00:29:09] Yeah. And that reminds me of something I’ve realized about this whole, newsletter game is that it’s really important that you stick to what you enjoy and are curious about yourself and are interested in writing about versus what people want you to focus on and write about, because coming back to your question about how to keep it up, I find that you’re just not going to keep it up.Well, if you’re writing for. What people want you to write versus like stuff you really actually are curious about and want, wanna write about. So I try to do like a 80%, what do I actually care about this week? And I’m excited to write about with a 20% of like, well, people care about it this week. And is this a topic that’s top of mind for anyone?Because otherwise you just, you just like created a job for yourself. You don’t like, and why did you even do that? Right? Nathan: [00:29:55] Yep. That’s good. And especially because it gives you permission as your interests change over time, right? For me, I started writing about designing iOS apps. Like that’s all I cared about.And then it was like, what’s the marketing and more general design. And I haven’t designed an iOS app in seven, eight years. I don’t know if those subscribers Lenny: [00:30:14] are still around Nathan: [00:30:16] there. There are some of them, you know, and, but if it’s around what you’re interested in, then it’s much easier to let go of those subscribers.Whereas if you’re like, no, I have to keep everybody on the list. Then you’re going to. You’re trying to force yourself to be interested in things that you’re just Lenny: [00:30:32] not. Yeah. And it’s just, you’re not going to enjoy it. It’s not going to be good if aren’t going to be like, Oh, this is, this is what I’m here for.Yeah. And so, so the key is just like just right. Yeah. So I mean, back to your question of process, I have this like list of what I’m going to write about over the next three months, but then I rearrange it constantly based on what I’m drawn to as much as I can. And that, that really helps. Otherwise you just, you just burn out.Yep. That makes sense. Nathan: [00:30:56] Okay. Now let’s talk, writing, switching to a paid newsletter. what are some nbers now? As far as how many subscribers you have on the free version and the paid version? Lenny: [00:31:06] So, so I’m going to share this publicly, in parallel. And so you can see the charts. If you’re curious, by the time this probably comes out, I have to have about 45,000 free subscribers around now.I have just over 3000 paid subscribers, and then I give a bunch of like comps to various groups. So it’s larger than that in reality, and make it about over 600 years, more and more than I made in my. Nancy tech job, which blows my mind. Like my entire goal in the beginning of this whole endeavor was once I make more than I made it, Airbnb I’m done.I don’t need anything more. I’m just going to stop thinking about growth. I’m just going to write, but it just keeps going on its own. I’m not doing anything and it’s pretty bonkers. Nathan: [00:31:56] Yeah. So what was, first that’s incredible. Like once you build that flywheel, it just. It Lenny: [00:32:03] keeps working. It’s all, it’s all word of mouth.Nathan: [00:32:07] I L I love seeing that. What, when you make the switch to pay, did you have a nber in mind of like, this is what I’m, I’m launching this paid version. We’ll say, you know, I don’t know how confident you were going into it. I’m always the one, like, this will probably never work, but here it goes anyway. but I always have a nber of like, okay, if I get a hundred people to pay for this, then it’s working.Like, what was that first nber for you? Lenny: [00:32:32] I had like getting, getting a thousand subscribers, I’d say paid subscribers. Cause that roughly equated to about a hundred K after all the fees and. And discounts and things like that. So initially it was a thousand, which is, I think it was Kevin Kelly. You talked about and true fans.And it was very real. It was like exactly. When I get to a thousand subscribers, I was making a hundred K a year, which is very livable wage in San Francisco, you know, borderline San Francisco. Right. And so that was, that was the goal. Initially it was like, you know, 500 and then wow. It’s thousand. That’d be amazing.Cause if you do the math, that’s up pretty quickly with, The subscription newsletter, right? Nathan: [00:33:13] Yeah. So what have you seen on free to paid conversion rates? you know, any in particular driving, more paid subscribers? Lenny: [00:33:22] So, so if you do the math of about 45,000 free and about 3000 pays, so it’s less than 10% convert, which is an interesting stat.Initially it was like 2% when I first launched. So I had like 10,000. Three subscribers when I went to pay it. And, and I had about 200 to 300 initially paid subscribers. So it was a very low percentage initially. And then over time it grows, was what was the other question? Nathan: [00:33:52] So, well, I guess, digging in on that, did you put more content behind the paywall?or did it just take take time, but what actually drove that conversion rate up? Cause you’re, you know, you’re pushing the eight, 9% now. Lenny: [00:34:04] So the way, the way I do it is I, I send an email once a week. If you pay you, get it every week, if you don’t pay it, you get it once a month. And so that monthly email basically has to be really, really good because that’s your yoursel.And sometimes I do these, like here’s a peak at this week’s paid post and give them a glimpse of what they’re missing. And then in the fridge post I share, here’s the three things you missed. So essentially it’s that free posts convert it to people, less Twitter. Just kind of sharing what’s going on in the pave land, but otherwise it’s all hidden behind a paywall.Nathan: [00:34:37] Yeah. So about having more of those more time for those, here’s what you missed. Here’s the free post to kick it. Lenny: [00:34:45] It just comes back to just providing value to people and they either find out about it or they want to access it and then they end up subscribing and stick around or leaving. How do you think Nathan: [00:34:55] about pricing of what price point you set and then how do you think about that changing over time or not?Lenny: [00:35:01] I definitely spend a lot of time thinking about it. I don’t know if my price is the right price at all. I experimented with various price points, but where I landed is advice I got is priced higher than you think you should. Everybody always wants to start at five bucks a month because that’s the lowest you can go.And no one ever thinks their stuff is worth it. So they’re just like, Oh, five bucks a month. That’s that’s so much money already. So, so I looked at the leaderboard. And if you think there’s like these various categories of newsletters, there’s news, there’s entertainment. And then there’s broadly just like analysis and make me smarter and better at what I do category and those charged like 20 bucks a month.So I just picked the middle and went with it. And initially when I launched, I did it, you had a display, there was a big discount. It was 10 bucks a month for a year. And then I increased or lowered the discount. It’s 12 bucks a month or 120 a year. And then I went to the. 15 bucks a month for 150 a year.And I still don’t know if it’s the right price. There’s probably some curve someone could do for me. That’s like the ideal place. Although I will say when I ran a deal, it’s like interesting learning. I ran a holiday deal and that drove the most subscribers I’ve ever had. And on one day when I discounted it by 25%, so that’s probably the right answers price, a little higher, and then discounted on occasion.Yeah, run Nathan: [00:36:20] a run a black Friday or, Lenny: [00:36:21] yeah, that’s what it was. It was, it was a cyber Monday holiday newsletter. Nathan: [00:36:26] Yeah. And I think that’s interesting. What are you thinking about bping up to the $20 a month or going off from there? You think it’s at the Lenny: [00:36:32] right? It feels so expensive. And I have this interesting.Too much pressure. Yeah. And, and I find that I have this interesting combination of people working at a tech company that it can, can expense it and the price doesn’t really matter. And then there’s like a lot of product managers in like India that email me and students in India. That’s like the most common source of emails that I get of just like, this is a crazy price for someone in my shoes.Is there any like alternative price for folks in India, for example, and I don’t know how to deal with that because. I want to devalue it, but it’s also a crazy expensive price. So that’s a struggle I have. I don’t know. It’d be interesting. Nathan: [00:37:12] I’m trying to think who said this or a bunch of people probably have, but of being like full price or free.And they always have that sort of methodology of like, yeah. I, I think it was someone doing agency work, honestly, of like, no, there’s no friends and family discount. There’s no, there’s nothing like that. I like these are my rates. Except for the times where I think it would really benefit you or like I’m going to do this for free.And it’s very clear that this is what I’m giving you. And there’s none of that. Like you’re paying for it. So you feel like you deserve things, but you’re paying half of the list price or a quarter of it. And so I feel like you can’t be demanding, you know, and there’s sort of that weird demographic. And so you could say like, look, I do full price and then I do full scholarships under.These criteria and I give out a hundred scholarships a month or 10 scholarships a month or whatever. Lenny: [00:38:02] I don’t, I don’t know we’ll do that, but that’s an interesting strategy. I do discounts of various amounts and I don’t know if that’s a good idea or not, but yeah, I do. I ended up doing like a 50% discount for students.and, and then I just give occasional steep discounts for folks that just feel like they, they, they would value it highly and they just can’t afford Nathan: [00:38:22] it. I do like the, the students angle. Cause then it’s just like, Hey, this is what it is. And people are paying for it. Right? The nber of people that are saying like, Oh, this will totally change everything.Can you give it to me for free? And then, you know, they’re not invested who knows if they’re going to read it or whatever else. Yeah, Lenny: [00:38:39] exactly. The other thing I’ve been trying to do really hard is to offer the content to folks that are just like, and afforded, or don’t even know it exists. I’ve been giving out a bunch of free subscriptions to like, women in product and like the black product managers group and, Latin X VC and things like that.And that’s been really helpful. Right? Nathan: [00:38:58] Yeah. That’s great. And it, it spreads the, you know, grows the community and everything else as well. Yeah, exactly. when you’re looking to, what are you looking to now for growth as far as is it just continually writing or, do you have specific goals in mind and, specific things as you look to, you know, to pass the 50,000 subscriber Mark or go from there?Lenny: [00:39:20] I, I try really hard not to. I think I mentioned this anytime we do anything, that’s not just create high quality content that creates value for people. It doesn’t do much. So 90% of my thought is always, how do I write great stuff, ongoing and sustainably. And it’s really easy to do more work and find more work for myself like in a podcast and write a book and create a course and all the things.And so I’m trying really hard to avoid as much of this as I can so I can stay and create just a really good newsletter. That’s hard enough. But the thing. So a couple of things have happened since I started it. One is, as I was launching the paid plan, I was like, man, 15 bucks a month is so much money to ask.What else can I offer people? And I suggested I was going to have a private community that you have access to as a paid member. And eventually I had to do it because I promised it. And that’s proven to be the most amazing thing that I’ve done maybe this year beyond the newsletter, because it’s turned into this amazing place of.peer support and help where people are just helping each other all day. And there’s about 2,500 people in there and just asking questions, answering questions. And I turned that into its own newsletter with the best conversations from the community each week. And so that ended up providing a lot of people.That’s the reason they subscribe. They don’t even hear about the newsletter. They just want to access to the community. And so that’s proving to be really interesting and valuable. And I will say I’m working on a product management course next year. That’s something I’ve decided to do to see where that goes.Nathan: [00:40:55] But I could see that there being a lot of demand for that. And one thing that’s interesting, there is a lot of people talk about a newsletter or like a paid newsletter as the business model, right. Or you can choose to do courses or books or sponsorships or a paid newsletter. And there. separate things and really, I mean, exactly what you’re pointing is like, they can, they can, co-exist just fine.You can do a paid newsletter and then do a course for this Lenny: [00:41:23] direction. Yeah. Yeah. Hunter Walker had this great post about how a lot of creators are. They have this one skew, which initially is the newsletter. And then over time you can add more skews, like of course, and I don’t know a book or something like that.And so. That makes sense, but it’s, yeah, again, it’s really easy to do more work and I’m trying really hard, not to just add more work to my plate, but this course felt like just, it felt like the right thing to do next. And so I’m going to experiment with that. Yeah, that makes sense. Nathan: [00:41:52] and I’m, I’ll just say I’m a huge fan of it because who I’ve seen, I’ve been doing that kind of thing for a long time of selling multiple products, multiple courses, and just seeing how one section of the audience really gravitates towards.Buying one thing. And another section is like, Oh, but we’ll happily pay you in aggregate $50,000 or a hundred thousand dollars for content on this, this specific area. And so being the, the multiple skew creator, really lets your audience choose how they want to support you and what they want to learn from you.Lenny: [00:42:23] I’m happy to hear this. Nathan: [00:42:24] Yeah, I think it’s a great direction. so let’s talk platforms for a little bit. Obviously sub stack is, are you started on medi moved to sub stack, sub stack is growing like crazy. They’re getting all kinds of press in the new Yorker, New York times, et cetera. I’d love your thoughts on just where the market is going, you know, and we’re, we’re kind of back on this topic, but, so I guess where the market’s going and then, what are the decisions for you on, you know, When to start on sub stack versus could consider something like a MailChimp or I’d ghost or convert kit.Lenny: [00:43:01] So what’s interesting about setup stack is I never would have been doing this with my life, if not for something like a sub stack existing, because I had no intention of ever one charging for a newsletter to even doing like a regular newsletter. I just started with a few posts and. The kind of the, the, the chemistry, that stuff stuck kind of discovered, I think, and went all in on was, let’s just make it, it’s really easy to create a newsletter and a blog, and then eventually it could charge for it if you want.And so I just followed the, I feel like I was exactly there, like in-store user journey that they mapped out in their initial pitch of like, I just play around, sign up, create a sub stack. Do if you posts it’s going well. Okay. Maybe I shouldn’t bet on this. Yeah. Maybe I should charge. And so, so we never would have been doing this if not for a platform like that, but in the end, it’s not a complicated set of features.And so there’s going to be more and more competition. and as, as you will know, and so I don’t know what’s going to happen there longterm. I will say the fees at scale are very painful and, and so the bet is that they provide. Enough services and benefits and maybe customers that make it worth it.But, and for now I’m just super loyal to them and just really enjoy that the platform is just because it allowed for me to live this life. so, so I’m happy. Nathan: [00:44:24] Yeah. I think from a, you know, both you and I working in product management and growth, and all of that, it’s fascinating to look at it from a case study of this is something that plenty of people have tried many times before.Lenny: [00:44:38] Great. Nathan: [00:44:40] Yeah. And I’m configured. We’ve been working on it for, in, in various farms and for a different market and for a long time and I study it and I’m like, okay, what, what did they get? Right. And it really is that they just made it effortless to go from, I have this one post, this thing that I want to write about to like, Oh, there’s a place for it.Oh yeah, of course you can subscribe. Whereas the industry for so long was, Oh, you want to start a newsletter? Like. Let’s glue together. 12 different things. Oh, you paid, Oh God paid. Oh man. Okay. You gotta, you gotta set to have so much stuff, you know, Lenny: [00:45:16] even like that first step of like, you want to start a newsletter.Like I wasn’t even in that mindset, I was just like, Oh, this is a better place to do a blog because I can capture email addresses. So yeah. So they just made it like a trick, almost that like, Oh, okay. I see where this could go. Nathan: [00:45:29] And it guided you into a six figure business. So I think that’s. I mean, that’s something that’s so important to have like finding a place to start because none of this matters, like people get so obsessed over platform or, you know, any of this, like what’s the fees.Exactly. And like, if you never get past a thousand subscribers, which a thousand subscribers is hard, like that is a meaningful bar, you get to that point, you have moment. but if you never get past that, like the platform that you choose. Does not matter. And so we’re exactly, you know, as newsletter creators, we often obsess over the wrong decision to start.Whereas the correct decision is, am I going to do this every day for a year to see if I’m, if I like it? Lenny: [00:46:16] Yeah, yeah, exactly. How do I, how do I figure that out as soon as possible and as easily as possible before I overthink all the different variables that come into play. And I totally agree, like in the end, it just, again, comes to, can I create value for people consistently?And then do I enjoy it? That’s, that’s a really important piece because. Cause like, you’re not gonna, you’re not gonna last if you’re not enjoying it enough, at least, you know, writing is hard. also, so there’s not going to be fully enjoying it. Nathan: [00:46:42] Yes. Yep. That makes sense. Okay. So something that I want to talk about a little bit more, is this idea of keeping the newsletters simple.So being in the online marketing space for a long time, I’ve seen people scale a newsletter or a content business, and they get to the point where it’s a little, you know, maybe they’re making 200,000 a year and they’re like, I should hire an assistant. I should hire an editor. You know, you get some of that help.and then it starts to go from there, right? Maybe they’re 500,000 a year, maybe a million a year, and they’re starting to be a team. I’d love your thoughts on that because. That’s a path that you could take. You could turn this into the definitive, like the definitive forget newsletter, the definitive news source for product management.You know, this could be something, in that way. What, what are your thinking about your approach and keeping it, keeping it simple? Lenny: [00:47:36] Well, I’ve worked really hard for many years and I know what that’s like. And. I feel like I have this opportunity to create a pretty balanced lifestyle where I don’t need to work 80 hours a week.And, and you quickly get there by just doing more and trying to add to it and accelerated and build more. And so I’m trying really hard not to do that. And I feel like there’s like, I could just do exactly this for a long time. And when it feels like it will keep growing, even if I do nothing. And I feel like I could make more just keeping it on my own thing.Not hiring anyone. Full-time not trying to, you know, add more business units to it. Maybe it’s wrong. But yeah, most of it comes from just like a, I could easily become a workaholic again and do a lot more work. And I’m trying hard to avoid that as much as I can while delivering consistent value. Nathan: [00:48:31] Yeah. I think that’s really important that you touched on of.But just a little bit of the actual take home of, you can keep driving that top line revenue nber, but this isn’t a, in this right now, a traditional startup. You’re not trying to make it that. And so actually the profit is what really matters. And so if we fast forward and we’re like, okay, this business is going to be.At $3 million a year, X nber of years from now. And it’s going to have in order to hit that revenue nber and provide that value for that many people, it’s going to need a team of 10 people. It’s going to, you know, it has all of these needs and before you know it, you’re managing payroll again and yeah.All this stuff. and that’s like, I think a lot of people get to that position, chasing the growth and then look back and say like, Oh man, I liked it when it was simple, when it was recurring revenue, serving a single audience in just showing up in a consistent way. Lenny: [00:49:34] Yeah, that’s, that’s my current philosophy, but I will say I’m, I have like a designer I’m contracting with, to like kind of level up that feel.I have a, a PM. I work with that, like hourly, where she helps curate this weekly newsletter. So there’s a few folks that are helping out and there’s a community events friend that’s helping out run events and things like that. So I think what I’m trying to do is yeah, just keep it really simple. Maybe that’s the philosophy.Just keep it simple. And you ended up making more and being happier. And so far it’s working out, we’ll see where it all goes. Nathan: [00:50:08] Yeah. I have a good friend, Josh Kaufman, who wrote the book, the personal MBA, and he’s done this really well of sticking to a really simple business. He’s gotten to the point.He’s always looked for channels where someone else is handling customer support. So like he likes to sell on Amazon audible and stuff like that. So he’s as the author, he’s one step removed. And that’s just one example. If he’s said, no, I want a simple business. and he, you know, that doesn’t mean you can’t work with a lot of freelancers, and have a team he loves to employ editors because they make his writing so much better.And that’s actually something that I’d recommend for anyone writing a newsletter where you want the content really good. Having someone that you pay to go. Yeah, I see where you’re going with this. What is going on in this section, like, you know, rework that yeah. Lenny: [00:50:59] If you have anyone you can recommend, that would be awesome.but I will say there’s like, I, maybe I’m just like, I don’t, I’m not in the, like the ambitious phase of my life. I feel like it’s totally cool to be super ambitious and try to make something huge also. And maybe there’s a venture scale return somewhere in this space, as a creator. And I think it’s totally fine to try.I just, I think for me personally, I’m just, I’m happy just making a meaningful income and not trying to turn this into like a billion dollar enterprise. Nathan: [00:51:31] One other thing on that is wherever, let’s say at some point down the road two years from now, three years from now that in that list of the 50 startup ideas, right.Maybe one of them does start to stand out and then you’re like, I think I want to pursue this. then you have this list of. 30 40, a hundred thousand, maybe it’s 200,000 people by then who you’re like you have your own audience and your own platform to launch to as well as all of these connections.Lenny: [00:52:01] Super true. Yeah. I could always turn in some new and I could just, okay. Newsletter is done moving off. Nathan: [00:52:07] Well, you don’t even have to necessarily give up the newsletter. Yeah, Lenny: [00:52:10] that’s true. If I can find a more efficient way of doing it every week while running a company, maybe. Right. Nathan: [00:52:15] what are some. Yeah.What are some interesting doors that have opened from writing the newsletter or opportunities that have come up where people that you’ve met that came about purely because you’re Twitter famous now, certain circle, Lenny: [00:52:31] speaking of Twitter, like there’s this amazing, super power that gets unlocked. Once you have enough followers, where any question you have, you could just ask it and you get all these amazing answers from people that are just.You know, very curious to see what everyone else says and they share their insight. So I find that whenever I focus on a topic and I want to get a more complete picture of how people are thinking about it, I just ask the question on Twitter and it turns into this really amazing resource. So I try to leverage that more and more because I find it it’s like helpful to everybody else.Also. It’s not just, Oh, here’s a bunch of answers I’m going to, I’m going to take it all from you. It’s like now this public thread of all these interesting. answers to a really interesting question. That’s one amazing thing that I didn’t see coming. And then two, I also angel invest and I find like 80% of founders are subscribed to the newsletter or have heard of it.And. As, as we know in investing, it’s it, it’s on the investor to get into great deals now because there’s so many VCs and angels out there. And so the more you people can see the value you can provide the easier it is for you to get into the deal. And now they can see, Oh, he’s smart about these things.We should let them invest. And so it’s been really helpful letting me get into it early. Interesting startup deals. Nathan: [00:53:45] Yeah. That makes sense. On the note of Twitter, what are some of the things that have worked as specifically grow your Twitter Lenny: [00:53:51] following. It’s exactly the same thing. Just providing value for people.Anytime I think of something either from a post that I’ve done or just that isn’t enough for posts. I just find a way to share it very succinctly on Twitter. Like, you know, how to do performance reviews or, or even just like smarizing a post that’s long into a Twitter thread. it’s just always that just provide value to people and the vole will retweet it.They’ll like it and all those things, and it just kinda builds on itself. Nathan: [00:54:20] That makes sense. And I mean, it just goes back to an everything that you’re doing of there aren’t, even though we work in growth and startups, There aren’t really growth hacks in the same way. It’s like, it’s show up consistently.That’s the hack show consistently and high quality. Lenny: [00:54:36] Yeah. Consistent quality. Exactly. Just provide consistent value to people. I know for like morning brew, a referrals program worked really well and there’s like, you know, cases where something like that’s not pure content helped significantly, but I find in the end, if your newsletter just isn’t growing significantly, I would just think about how do I provide more value to the readers.Again, and again and again, and it’s not going to happen overnight. And that seems to work. Nathan: [00:55:01] Yeah. Okay. Last question I realized, I was thinking about on the pricing side, you have this, this split that you talked about between individuals paying for it and companies paying for it. And I think that’s relatively new in the newsletter space of a company like a B2B newsletter.Yeah, exactly. And so if someone was starting out and they’re trying to hone in on their topic and maybe there’s an option for them to write. Something that could be expensed. how would you think about that? Do you think that’s happening a lot? Is that important or does it matter? Lenny: [00:55:33] I don’t actually know what percentage of my newsletter is expensed.If I had to guess it’s like 20% expensive, something like that. And so that’s not like a game changer and it’s hard to like, if, if you listened to my advice of stick to things you’re interested in, it’s hard to like Frankenstein on. Oh, I’m also going to have this thing that just happens to be interesting for companies.But, but it’s, it’s a helpful thing. And I’ve tried to do a little bit of proactive B2B kind of sales, and it doesn’t really do much. I find that it just, I have to wait for people to come to me and ask for like both discounts for their company. And that works well. I also find VCs are offering it as a perk to their portfolio companies occasionally, but all that just comes to me anytime I pitched them on it, doesn’t give anywhere.So, but it’s an interesting new trend and, I don’t know where it’s going to go. I don’t know if it’ll ever be like 50% of, of my readers. but yeah, if obviously, if you can create value for a company, they have more money. Right. And so you’ll have some sales there. Yeah. Nathan: [00:56:34] On that note, it just made me think of advice I’ve given in the past.when people are trying to hone in on a topic and it’s like, well, if you’re trying to make money yourself through, through teaching, right. Which the newsletter, of course, any of that. W we’re teaching in one form or another. If you’re trying to make money yourself, then teach a skill that makes money to people who have money.And so we’re not talking about, you know, knitting to teenagers, right? We’re talking about product management, growth strategies to startup founders, PMs companies who have money. And so it’s probably not like canvas be expensed or not that you’re thinking about. It’s. Okay. Am I delivering value, a level of value that people can, are now living with, you know, and it, and it will level up their career.Lenny: [00:57:22] Yeah. Those are definitely the easiest newsletters to monetize. There’s also just like helping make money directly. Like there’s like Bitcoin newsletters and, there’s one around like a distressed asset investing that does it really well. But then there’s also just like, if you look at the subset leader board, like the first two are all just news, like politics analysis, like a really unique perspective on politics.So you can definitely make money just through news and analysis. And also just like entertainment, like the browser is this awesome newsletter. It’s just beautiful pieces of writing everyday and people pay for that. So there’s a lot of different approaches. Nathan: [00:57:57] Do you have any newsletters beyond what you’ve just mentioned that you particularly love?Lenny: [00:58:02] I always worried about answering this question cause I have so many newsletter friends in that one. I always worry. They’re going to get upset at me. You single somebody out. Exactly. So how about, I’m going to tweet my favorites and then go follow, go. Find me on Twitter. Nathan: [00:58:17] That sounds good. Well, that’s a good place to wrap up.So on that note, where should people follow you on Twitter and then subscribe to the newsletter? Lenny: [00:58:23] LennysNewsletter.com, which just redirects to my Substack and then just Lenny-san, S-A-N, @lennysan on Twitter. Nathan: [00:58:32] Perfect. Well, thanks so much for joining me. This is a really funny conversation and, we’ll, we’ll talk soon.Lenny: [00:58:37] Thanks for having me.

Byrne Hobart is a chartered financial analyst who loves writing about the intersection between finance and technology. He writes The Diff, one of Silicon Valley’s most popular newsletters. In this episode, we dive into how Byrne launched his newsletter, how much he’s earning, and how he publishes five times a week!You’ll learn why Byrne isn’t worried about pirates getting their hands on paid newsletters, and why you should worry about selling hard enough, instead.Byrne talks about how to build recurring revenue, and writing for different types of readers. He also points out an important factor that affects the churn rate of your newsletter!Byrne shares further insights on using free social media to lead people to the channels you monetize, and why he competes for readers’ highest-value time, instead of appealing to the lowest common denominator.Links & Resources Jonathan Haidt - Social psychologist - Author - Professor Manhattan Project - Wikipedia Apollo program - Wikipedia Stratechery by Ben Thompson – On the business, strategy, and impact of technology. BitTorrent - Wikipedia Snopes.com - The definitive fact-checking site and reference source for urban legends, folklore, myths, rumors, and misinformation. Byrne Hobart’s Links Sign up for The Diff Medium: Byrne Hobart on Medium Twitter: @ByrneHobart LinkedIn: Byrne Hobart Episode TranscriptByrne: [00:00:00] I wasn’t really thinking of the paid newsletter as this is going to be the main thing I do. you look at tech companies, they often have multiple lines of revenue, one thing they do is 95% of revenue. And the next thing they do is 2% of revenue, and when companies get more mature, it’s sometimes spreads out a little bit, but early on you find one thing that works really well. And that’s what you focus on.Nathan: [00:00:25] Today’s interview is with Byrne Hobart who writes The Diff. Now Byrne is a chartered financial analyst who loves writing about the intersection between finance and technology. What’s really interesting about his writing is that he’s read by basically the who’s who of Silicon Valley. So it’s not just, you know, a larger email list that we’re talking about today, but really we’re talking about writing the kind of quality content that, You know, billionaires are reading that.Like I first heard about him from Patrick Collison at Stripe. So this is the kind of thing that a lot of really important, really interesting people are paying attention to.So in this episode, we’re going to dive into how he launched his paid newsletter, how much he earns. He publishes five days a week.These are long form detailed con detailed articles that Bern is posting basically five days a week, which is, is a crazy consistency. So his writing process, what inspires them and so much more what’s that then.Byrne Welcome to the show.Byrne: [00:01:23] Great to be here.Nathan: [00:01:25] So I’ve been following your newsletter for awhile and I’d love if you just gave a quick intro from your side what you write about and why you find it interesting.Byrne: [00:01:35] Yeah, sure. So the idea is that I like reading history and I found that if you read We contemporary coverage of things that are happening at any given time you do get a lot of the details and then you get a lot of stuff that ends up being totally irrelevant And a lot of really interesting developments just are below the surface or they they matter in retrospect but no one really understood them at the time And so what I’m always trying to do which is a really high bar to reach is to write Right things today from a perspective that will still make sense it’d be relevant in the distant future So it’s basically trying to spot the important technology trends trying to spot what mattered what people thought mattered didn’t matter how those perceptions changed how how perception and reality have interacted and the way to do that is one to talk about financial markets because financial markets are Aggregating knowledge preferences expectations et cetera from everyone around the world And then the other thing to do is talk about technology particularly technology companies And the nice one of the nice things about those companies is that they have to be somewhat open because they’re all constrained by their ability to hire people And one way to hire people if if you’re trying to compete with Facebook and Google and Amazon and Microsoft and they can all offer a really generous comp package The way to hire people is to to give them some expectation that this company is going to be totally transformative and amazing So even if the base pay is not quite what you get at Facebook it’s still worth doing either to make an impact on the world or to cash in some stock options So a lot of companies have this incentive to actually tell their story in a way that that doesn’t happen as much in in other fields But at the same time companies have an incentive to hide their story Because if the story is we’re doing X but we’re actually going to kill Google And here’s how you don’t want Google to know that So there’s there’s always this corporate stress He doesn’t where you have to be really appealing and inspiring but you can’t tell the whole truth because it’s too dangerous So I try to parse thatNathan: [00:03:42] yeah, I think that’s fascinating. And I’m spacing on who talks about this a lot is a book that I read fairly recently, but about how, Now, this is going to bother me of who I never, what book it’s from, if you’ll know it, but how the closer like a startup is going to talk about how they can create a monopoly and they can have all the success.And then the closer they are to actually creating a monopoly, in and succeeding the less they’re like, Oh no, no, no. It’s not a monopoly at all. No. W like, look at all this competition. We have, everybody has a competitor.Byrne: [00:04:14] One has that, they have this, this like nber line of. Here’s like everyone, if you’re, if you’re an airline, you’re like, here’s why we’re really special. Here’s why everyone loves Delta. And the United is like, no, here’s why everyone wants United. And then, if you’re Google, you’re like, well, we’re one advertising company among many.And our customers could go to all sorts of different media, but really Google has a, basically a monopoly on search and search is an incredibly lucrative business, but yeah, they, they can’t quite talk about that. And there are, there are other companies that have these little monopolies, like sometimes, If you, if you look at the, some of the large us companies that had large research labs in the thirties, forties, fifties, in some cases it seems like part of the point of those labs was to give them somewhere.Somewhere, they could dp their excess profits so that they just didn’t look that profitable. So if you’re at and T you have this incredibly lucrative business with network effects, you have a technology advantage. And one thing you could do with that is, just run it for maxim profit margins right now.But the other thing you can do with it, if you’re worried about. FDR are complaining that you’re terrible people is you hire a bunch of scientists. You tell them, please just work on something. It should help us. But, you know, we just, we w it’s basically a way for them to defer their profits to some future that’s more politically optimal.And, and then you get lots of wonderful side effects. The transistor.Nathan: [00:05:36] Yeah. Oh, there’s so much to that. And so, anyway, I think those are just fun. Examples of ideas on what you tend to write about, kind of staying on the topic before we dive into newsletters specifically, saying on the inflection points in business, I’d love to hear like what, or maybe I’ll start with what’s one or two that you’ve seen in particular this year, since this year has been a very transformative year.Byrne: [00:06:00] Yeah. So, you can, you can look at the obvious inflection point of, you know, before we were all going to social gatherings and going out to eat and traveling. And now most of us are not doing very much of that at all, but I think one of the inflections there was, this. It results. Some policy argents about the extent to which you can actually solve a recession just by spending a lot of money.So there’s always this concern of if we spend a lot of money it’s hyperinflationary, but in an economy that’s already pretty levered. There’s actually, there’s a pretty good argent for having somebody stabilize that. Then you can, you could imagine one steady state where we just don’t have as much leverage.And so you don’t have as many people who, if they lose their job now, they can’t pay their rent. So their landlord. Can’t pay their mortgage. So the bank has trouble with its finances and it just, just bounces through the rest of the economy. in a less levered economy, that’s just less likely, but in an economy where you have this pretty robust financial system, where a lot of people have, fixed obligations, a lot of companies have fixed obligations.As it turns out when there’s a huge demand shock to the system, you can actually just spend a ton of money and, and things start to get better. So it’s, One of the worst recessions on record, but one of the short-term sessions on record and, it so far has worked well. there is a question of how technocratic we want things to be.There’s also a question of, did we. Did we stop a depression in 2020 and get something worse than 2021. So there’s still some open questions, but I think it does. It does tell you that some policymakers have, have more power than, than we thought, or it can have, have more powers they can use for good than we thought.But at the same time, you have a lot of people questioning a lot of powerful institutions because they’re, if you go back to the, the discourse on COVID in January and February, it was, it was kind of seen as, as sort of extreme and paranoid to worry about it. There’s the famous of box piece. Yeah.These people aren’t even shaking people aren’t even what’s wrong with them. It’s, it’s no worse than the flu, get a grip America, et cetera. So, we’ve had some institutions where we’ve had to seriously question their legitimacy and, a lot of these institutions are fighting back by kind of dodging it like, there’s, there’s been a bit of soul searching and actually, some of the, one of the Vox writers who had covered COVID early, actually talked about how they’re, She could have done more.Her name is escaping me right now, but she actually did a fair amount of soul searching and actually wrote a thoughtful piece on, part of it was on just the factual question of when was it clear that this was a crisis and what, what should be done about it? And then part of it was this meditation on the institutional incentives.So. It’s it’s tough to be early, especially. if you are a journalist at a large publication, you have this surface area problem where, the bigger the publication is the, the more risk they take from any one person saying something crazy. And, the bigger they are, the more newsworthy it is. If any one person says something crazy.So New York times has a lot of writers and it’s also a well-known institution, which means that they actually face a ton of risk from their employees going off the reservation. And. What, what I think you see is that a lot of these institutions they’re converging on some range of acceptable discourse, and they’re just, they’re writing off the set of people who.Don’t really think that way, but they’re very much speaking to the they’re preaching to the choir for the people who do agree with them. So you actually end up with a much stronger filter bubbles, as a result of this questioning of legitimacy. So that’s, that’s an important inflection point. And, I think the other, the other side of that is that we did learn that.Tech companies broadly defined, did a great job. They sent employees home very early. the internet kept running. So the telcos did, an excellent job at, not allowing that whole system to fall apart. a lot of, retailers, for example, and manufacturers were able to adapt quite quickly. So there were toilet paper shortages briefly, but then, We got more toilet paper.there are still shortages in a couple areas, but, stuff like exercise equipment, it’s still hard to find. last time I looked podcasting Mike’s were still hard to find, but in a lot of cases, the, some parts of the system were exceptionally adaptable. So in many ways, you know, if you, if you didn’t like going out that much, if you were already the kind of person who used a lot of, a lot of grub hub and Postmates, Some things haven’t changed that much.In some ways, things are actually easier because now, now if you tell someone I don’t want to hang out, we should just chat on zoom. It’s actually kind of normal. So, you know, for, for introverts and a lot of these companies are, their workforce tends to be more introverted if they’re tech companies, it’s, it just hasn’t been that big, an impact relative to the worldwide impact.Nathan: [00:10:53] Yeah, that makes sense. Is there something that, you know, we’ve seen these changes happen right now? The, all the things that work from home and everything else that’s right in front of us, but what’s something that an inflection point that you think has happened, but we haven’t noticed the effects of it and we won’t.You know, three years from now, we’ll look back and be like, Oh, of course, that changed in 2020. But you know, you think people right now would be surprised or, not actually expect to see that change.Byrne: [00:11:22] Interesting. I think, one of the interesting changes is this, this, in the. Hardware business. And specifically in chips, there’s been this narrowing of which companies can effectively manufacturer the most cutting edge chips. if you look at the, the nber of semiconductors, your fabs at, at every node of design, as the nodes get more advanced than nber of fabs, that can actually do the nber of companies that own fabs that can do this.Just diminishes and diminishes and diminishes. And now we’re at the point where, the most advanced trips can get made in Taiwan or they can get made in, South Korea. And there’s really, no one else has caught up to them. And this is something that, that people are aware of, but I don’t know how much we’ve thought through the implications of, One country that has had, had disputes with China here and there.And, it was at war with them at one point, in the fifties. And then you have another country that China says as part of its territory and so very, very serious, very deep-seated disputes there. so. These, these countries are, are both pretty, more geopolitically tenuous than, than other places in the world.And they are the only place where this really essential set of components gets manufactured. So that’s, that is a case where the, the world of geopolitics and macroeconomics starts to intersect with the world of technology. Right. And you started asking what it looks like if, the U S no longer has access to tips, or if China no longer has access to tips, because both of these countries are, very close to the U S diplomatically and, they’re, they’re close to try to geographically, so it’s, it makes the world much more interesting and much more high risk.And it’s, it’s part of a general force and technology that you end up with. These increases only elaborate supply chains, where there are these really narrow slices that are super profitable. And, as, as they get more profitable, they get harder to duplicate. You end up with more monopolies and those monopolies just, as, as an shrinks from, you know, there are, there are dozens of companies that can do this too.There are two that can do this. Then you have to stop thinking of this as a statistical process and start thinking of it as, That’s something closer to a narrative where there, there are these very specific entities. There are specific people in charge. They have particular incentives and they think about things in a particular way, and it really matters for the future, how they think and what they decide.Yeah, that’s fascinating. I. You know, from the, the nineties and earlier you think of oil as being that, that resource that is worth fighting Wars over. And so that’s fascinating that it could turn into chips and it might not go to Wars, but certainly very heavily, you know, a lot, a lot of, geopolitical issues around that.Yeah, there’s this The good Lord, didn’t see fit to put oil only in places where we’d like to do business, but we go where the oil is. And you can think about that with chips too, where you, if you were designing a, a supply chain for the U S technology sector from scratch, you probably wouldn’t put the most strategic components.All right. Next to a country that is trying to build its own supply chain. And that increasingly sees the U as a major rival. You’d probably arrange it a little bit differently maybe, but these, these plants in, I don’t know. England, or maybe you put them in America. And the U S is sort of trying to do that.And the semiconductor industry is lobbying very hard for the U S to do that. Taiwan semiconductor has, has plans to open a facility in the U S and, Samsung is expanding some of their manufacturing in the U S so it’s, it’s slowly edging over that way, but China has. subsidized that business massively, a friend of mine, Jordan Schneider, who writes a China talk, he estimates that it’s something like $1.4 trillion that China has, has spent, or is planning to spend on this industry.So that’s clearly, clearly they’re taking it very seriously.Nathan: [00:15:23] Yeah. Oh, that’s fascinating. So I want to transition right now because, and talk more on the newsletter side. Cause this is a taste of the kind of thing you, you write about and the level of detail that you go into. And so this is why, you know, executives and founders at so many top companies are following your stuff.Cause you’re watching. These kinds of trends and seeing, okay, what are the implications of this? And so I’d love to go back a little bit in your story and just, focus on three years ago, five years ago, what, what were you doing? And what’s the path that led you to this point of kind of being on the cutting edge of, and the narrative of what’s going on in the world.Byrne: [00:16:00] Yeah. Sure. So, mostly doing equity research. So I worked for a while at a hedge fund SAC capital, and then, worked for some research providers who work with ones like that. And, that, that work was actually really fun because the equity research it’s, It promotes some really healthy mental habits, because if you were trying to decide if a stock is a buy or a sell, you do want to have your thesis, but you actually want to pay very close attention to who you’re arguing with and what their thesis is.Because the most valuable things you learn are from the people who disagree with you. And if you tune out the other side of the argent, then you are necessarily the db bunny. So you can get lucky. You can still make money and that’s happened to me, but, You it’s, it’s a lot smarter to know exactly what these guys are betting against and why you think it’s wrong.So that’s, and that’s. Normally in argents, that’s the healthiest way to approach things is you figure out how to reproduce the other person’s argent and then you figure out what they’re missing or, or you just figure out what fundamental disagreements you have. So a lot of political argents, you think that it’s an argent over, over policy outcomes, but it’s actually an argent over, what is what’s practical to implement?And, there’s a Jonathan Haidt has a lot of research on that. Or hight has a lot of research on. And this idea of moral foundations where different people just have different things that they care about or different things that are willing to treat as morally significant. And you can, you can have an argent with someone where it seems like the other person is just, Just promoting something totally inhan and evil, because they have a different set of priorities that they’re willing to give credence to.And if they, if they only, if you only cared about the, the care versus harm moral foundation, so it, it, does it hurt people or does it help them? You get one set of conclusions, but if you care about that, but you also care about things like. Respect for, respect for authority and respect for these symbolic things that, that don’t have real world value, but do matter, in the abstract, then you get to a different set of policies.And, it’s what hight claims is that when people with different moral foundations try to model one another’s beliefs, they just tend to asse that if someone waits care versus harm differently, it just means they want to hurt people. Whereas what it actually means is they’re balancing a different set of priorities.with finance, you don’t really have to worry about moral foundations that much because everyone wants to make money. you can sort of have moral foundations with things like, investing in tobacco stocks, but that’s a very quick argent. One person says. This company is a very profitable, and we don’t think that they’re going to shrink as fast as the market thinks.And then someone else says, yeah, but they cost cancer. So I’m not going to invest in that. So that’s a very quick argent. It’s not like they have any disputes about fundamentals. They just quickly get to what the substance of the dispute is. And then. When people debate companies like, like Netflix and there, you know, you have one side saying original content is this bottomless money pit.And they have to keep spending more and more and more just to, just to keep up with the other streaming companies. And then someone else says that that’s theoretically true, but they actually get economies of scale and they get economies of scale on acquiring users. And so you’re, as long as you’re amortizing content over a larger and larger user base over time.And as long as you have a lot of pricing power, It doesn’t really matter that it’s expensive to have this original content. And maybe it’s actually good because it means that eventually other companies get scared out of competing in the first place. So you at least figure out what the questions are, what the uncertainties are, and then you start modeling.You start trying to figure out what does it look like if you scale the, the Netflix movie production function up to X or up five X. And then what does it look like when Netflix raises prices in a country like the U S versus what a, what pricing power do they have in. a much poorer country, for example, so that that’s a really healthy habit where you’re, you’re trying to figure out what you actually disagree with people on, and then you want to resolve that disagreement and, and get it right.And. Because prices are set by people who are trading. There’s actually an incentive for people to share what they figured out out. If they’ve figured out something novel and insightful, and they’ve already made the trade. So a lot of people, well exchange ideas, they debate very vigorously and they’re in some sense in some totally cynical utility maximizing, since they’re still trying to get at the truth in, in just that narrow domain, but you take the habits from that domain and then you apply them to other areas and it’s generally useful.Nathan: [00:20:38] Yeah, that makes sense. Before we get to newsletters, I’m realizing I have one more question. what’s something surprising that shaped your view of the world. You have a very unique take. And so I’d love to hear what, you know, what’s something that people wouldn’t expect that plays into that.Byrne: [00:20:52] Yeah. So I, Very rationalist view of the world. And I’m sure I still, I still try to, I still tend to take a more, more linear left-brained view of things, but, I do think that there’s, there are important coordinator functions that are served by these irrational, irrational behaviors.So there. So things like financial bubbles, you can look at a financial bubble as just people being bad at math and paying too much for stuff, investing too much and stuff working too hard on, on, on endeavors that are just not going to have any kind of meaningful payoff, but you can also view a bubble as this coordinating function, where for a lot of complicated technologies, you need a lot of things to go right at once.So you can look at the internet bubble as being this combination of a bubble in, And ISP and telecommunications, but also a bubble in creating content online and also a bubble in selling goods online. If those didn’t happen all at the same time, none of them would have been possible. So if you build amazon.com and nobody has internet access, then it’s worthless.If you, if you build PayPal and nobody’s buying anything online, worthless, but if all of these things are happening at once, then collectively, they are actually worth a lot. It it’s still very uncertain. And, a lot of people got burned, including anyone who bought Amazon at the peak. It was a very long time before they got back to breakeven, but it did coordinate all of these developments and build something that was hard to replace.And, I, I think there’s a parallel between that and. What happens with successful mega-projects from governments. So, if you look at something like the Manhattan project or the Apollo program, there are all these discrete components that have to be built for the project to work. And if you build one of them and the other one doesn’t get built, it’s worthless.So you have one group of people designing a bomb, and you have another group of people purifying, vast amounts of the correct urani isotopes to build a bomb. If you purify a bunch of the right isotope, but there’s no design for a bomb, then you’ve wasted a ton of money. And I believe by the end of the war, the investment in that urani project was actually larger than the total investment in the automobile industry at that time.So you would huge project could have been worthless. they did a lot of these things in parallel, so they didn’t actually know if the final design would work, but. it’s very much like a bubble. You’re doing this thing that is irrational at one level, but if everyone’s irrational in exactly the same way and you all give up what tasks have to get done, then you end up building something that you could not build on your own.You couldn’t build it any scale lower than that.Nathan: [00:23:29] Right. Yeah, that makes sense. Okay. So you’re going from the world of finance and, then, just this year, right. You made the switch or was it last year? You made the switch to the newsletter.Byrne: [00:23:40] Yeah. So I, messed around for a while, did a little bit of just freelance writing in a couple of different places and did some consulting. And then I, I started the newsletter, mostly promote other writing. So I’ve been doing that for about 10 years, just very intermittently.And, I started writing the newsletter more regularly and then charging for it in February of this year.Nathan: [00:24:08] I’m realizing we’re gonna publish this in 2021. So I should do it throw a year in there. so let’s see. Yeah. I mean, going back through your stuff, you’ve been writing for a very long time, but publish on medi. Well, before you got started on Substack. Yeah. But to what I’d love to hear what some of the things that you were looking at when it was like, okay, let’s change it from, you know, we’ve been newsletter as a way to.Send my writing to people, right. At that point, it’s just a push mechanism. And then that transition to the newsletter as a business. Now, maybe two things, one, what were some of the people you’re looking to for inspiration there, who sort of charted that path for you? And then, what were the, the markers that you were looking for for like, Oh, I should actually do this.Byrne: [00:24:55] Yeah, I think so there’s There’s what you work on and then there’s how you monetize it and these can be very different. So Nike, for example, in one sense, they are an ad company. They just found a way to monetize by selling shoes. And they’re really good at it. And you can look at a lot of other companies that way that they.They do one thing and then they monetize it through something else. So I, I wasn’t really thinking of the paid newsletter as this is going to be the main thing I do. I was thinking of it as I have these different channels andI’m in one channel, someone else owns the platform and I, I I really like working with them and I still write for them.but it’s, it’s, it’s not recurring revenue. And so I wanted to have something that’s recurring revenue, what I thought. And I actually, I built this little financial model. Which immediately became obsolete. And I was, I was looking at different income sources, different things I’m working on. And, I thought the newsletter, you know, they could end up being a third of my income.And so I’d have this diversified set of, of different activities I do. And there’s one that’s recurring, so that’s really safe, but it won’t be that big, cetera, et cetera, et cetera. But, what I should have been thinking was when you look at any. If if you look at tech companies, they often have multiple lines of revenue.And it’s like, one thing they do is 95% of revenue. And the next thing they do is 2% of revenue, but they break even doing that. And then the next thing they do is Piney Teddy’s revenue. So, I think, and when they, when companies get more mature, it sometimes spreads out a little bit, but early on you find one thing that works really well.And that that’s what you focus on. that’s, that’s roughly how it happened with the newsletter. I got a couple of people to sign up. It started growing and it just, it grew pretty steadily. Like when I look at the chart, there are these bps, mostly from people recommending it publicly. it’s and those, those have happened just periodically pretty much since I started.But a lot of it is just this gradual process of. You send an email and a bunch of people read it and some of them send it to someone else and that person reads it, likes it wants to read more. And I have another subscriber. the, the social proof of you got this paid email from some, you got this email, that’s a paid subscription product.And, so the person who’s sending it to, you knows you and they know you’re interested and they’re implicitly endorsing paying for it. That’s, that’s really powerful. So a lot of it is compounding from that. What that means though, is that posting frequently, as long as you have something to say is really powerful.So if you have. Five opportunities a week to do that instead of two, then the compounding process should happen lot faster and there is a balance to strike, but in general, there’s a huge amount of information out there. you can, you can always think of just how much competition there is for people’s attention, but a lot of it is for attention that people are implicitly putting zero value on.So a lot of, a lot of us, myself included have this just muscle memory for. I’m bored or I’m waiting for something to happen. I’m going to open a new tab and I’m going to go to hacker news or Reddit or Twitter or something. And that time is not the time I’m competing for. I try to compete for time.That’s very, fairly valuable. That’s why, the newsletter is an appropriate form factor because it’s going into the same inbox as a lot of pretty important stuff. I know some people will filter and sort, but. A lot of people have this default approach of I’m going to get a ton of inbound email and I’m going to manually filter through it and decide what’s important.So I’m generally competing for people’s attention, against pressing business matters. And that’s, that sets a really high bar, but it also, again, adds some social proof where if this is worth the time of a busy person, then it’s worth it. to read Nathan: [00:28:42] I think that’s something with paid newsletters that people worry about, right. Is that I’ve put this out there and obviously it’s only available to paid subscribers, but are they, everyone has it in their inbox. There’s no lock on the version in the inbox. So I can just forward that on people say like, But, you know, what’s to prevent someone from just giving it away.And what I hear you saying is nothing. And that’s the beauty of it, because worst case I’m not going to forward it to dozens or hundreds of people, I’m going to be like, know, I’m going to send it to my friend, Ryan, Hey, Ryan, you’ve got to read this. And then that’s exactly what you’re saying of like, Oh, well, if this is $20 a month, I’m reading it.This was good. Nathan pays for it. So he must think that it’s worth paying for every month. So like, you know, the other four articles a week are really good, so sure. I’ll subscribe and check it out. And you’re right. That’s really high. It’s social.Byrne: [00:29:32] I would say piracy at some point I’m sure it will be a risk I’m sure it will be a risk and I’m it probably exists in private chat groups that there’s some roster of. Here’s the pirated Stratechery feed here’s the pirated sinuses and feed, etc like that stuff happens, but it’s just. Part of what you can take advantage of is it’s incredibly embarrassing to ask and it’s excruciating to ask multiple times, like, I, I signed up for the information because I was midway through sending someone a text message being like, Hey, I saw another headline from the information.I really want to read this article. And I was just imagining him getting this periodic reminder that I’m cheap and just dismissing it. I know people will pirate it some people will pirate stuff at scale, but they’re not really, they’re not a huge audience. A lot of people just don’t behave that way.And in a lot of cases, what we saw in music and movies was that piracy was about usability. That if, if Netflix and Spotify are more convenient than BitTorrent than BitTorrent, it’s still a factor, but it’s not a huge factor. And a lot of people graduate, they, they torrent the first alb but they eventually get on Spotify and then it’s just too easy.They never stop. And, the, since the economics are a lot better for paid newsletters than for piracy, like, look at the ads that, the torrent sites have to run. Clearly, they are not actually hitting a super high-monetization ultra-desirable audience. So I would expect that as piracy becomes a bigger deal, a the, the newsletter technology companies, the platforms are going to notice it before the individual users do.Users, some users might notice and complain. You know, if they see this reader opened the newsletter 500 times and clicked 2000 times on different links, like, okay, that’s something something’s going on there. But the people who will notice it at scale and actually start detecting it and perhaps come up with countermeasures perhaps just say going to happen, but it’s not economically a huge deal for you.that’s, that’s probably going to be platform-side Nathan: [00:31:31] Well, I think what’s most interesting about it is, is not just that it’s a small, like piracy being a small issue, as far as the overall monetary side, like, you know, whatever those people were going to pay you, but also that it may be a benefit of, of exposing new people to it. You know, like your friend who sends you, the information says, Hey, you got to read this article.And then later you’re texting him, like, can I read that article as well? You know, he introduced you or she introduced you to that quality of reporting and then kind of got you hooked. And so, you know, it’s interesting to think about it being potentially a goodByrne: [00:32:04] Yeah, I, I think Piracy is not just, you get an email that you paid for and you send it to someone like piracy is you, you do that systematically, or like you have a special Gmail that a lot of people log into and maybe, maybe they’re paying you like $10 in Bitcoin every year to get access to the giant email list.that’s that is, there are definitely, there’s like a pretty discreet gap and yeah. It’s it’s kind of, like you can, there’s always the continu of how monetizeable a given media, given the physical instantiation of media can be. if you look at the music industry, you could, you could monetize by selling physical albs.You can monetize through radio, you can monetize through touring. You can monetize through merch there’s, there’s a whole spectrum of price discrimination and you, you generally want to have some aspects of it that monetize very poorly because they have low frictional cost of sharing. In fact, that’s a, there’s an interesting dynamic across different media sites where sometimes there is a low-monetization low-friction site.And then there’s a high-monetization high-friction site that has the same kind of content. But the, there are people who use both of them and they use one to get followers for the other one. And so you can, there are people who will use TikTok to promote their YouTube channel. They know that YouTube subscribers are stickier, they can get advertising on YouTube.A lot of people including me, will use Twitter to monetize Substack So Twitter by design is supposed to be this ultra-seamless process for sharing stuff and having it go extremely viral. Substack is just not going to be extremely viral. There, there are examples of viral emails, but they’re all in the distant past.And it’s It’s viral. But if you look at the, the forward line, it’s like 150 people read about it. And then someone posted it, to Snopes.com or something.Nathan: [00:33:58] Right. So let’s dive into that on the growth side. I think Twitter is a very common path for growing a newsletter. They, it just has distribution in a way that. You know, email doesn’t have built in, or I should say discovery, as discovery built in, in such a good way, what’s worked for you on, on Twitter and maybe a couple of examples of either threads or individual tweets or articles that have been right.Byrne: [00:34:22] No, I have, I don’t have a good one sense of what actually works in terms of getting a payoff in subscribers, because it seems to happen. So asynchronously that it’s more like. If you, if you tweet and people like it, they will follow you on Twitter. Eventually, if you occasionally tweet links or as I do shamelessly tweet links to your newsletter, eventually some of them will subscribe on the free list if they get enough free issues, some of the most apart from the paid list.So the conversion funnel is really gradual and, because. You don’t have, you don’t have a good way to track the, the user, path from, they saw someone retweet you, but didn’t interact too. They saw a tweet. They followed you all the way down to, they paid you money. it’s, it’s tough to see them through that entire funnel, unless, well, sub-sect dismissed the rors that Twitter was going to buy them.So that will happen. Probably probably for the better anyway. so it’s, it’s really tough to say other than just, if you can be the, the Twitter ISE 280 character version of what you are in long form on, on a newsletter, then you will, you’ll give people a pretty, pretty close approximation. So I’d say that my Twitter.My Twitter feed. I will sometimes tweet general observations. Sometimes I’ll tweet something about a story that I end up writing in more detail for the newsletter. Sometimes I’ll ask people questions on Twitter. Like if there’s just something where I have an open question, I haven’t found a good answer from Googling, and I know there’s a good answer out there.I’ll ask people. I, I do occasional Twitter things that are just things that have to be that day and it, It feels not, not like a good deal at all for someone to put the email newsletter on their expense account and then get a story about a toddler. So, that does not make it into sub stack, but that’s just because a lot of my friends follow me on Twitter.So it’s a way of keeping in touch with people. I, one of the things I do on Twitter pretty regularly is when I write a post that is paywall, I will generally tweet out a link to it. And I will often tweet out a screen cap of something I said in that post, the only annoying thing there is that I want the screencap to be interesting, but I don’t like to post spoilers.Is one of my rules. So I will, I will often screencap a tangent or a footnote or something else in the piece that just gives you a sense of what I’m writing about, but doesn’t give away the whole thing for free. And I don’t know, I don’t know what percentage of the content ends up being given away for free versus, charged for in theory, I, I tell people I’m going to post three times a week.I generally post five times a week. one of those posts is free and the other one’s okay. Walled usually, but I will occasionally take something out behind the paywall. So, I had a piece on Palentier that I wrote after the S one was filed and I was just really proud of it. And, I was also kind of disappointed in the overall media coverage of Palentier, which is some combination of this is the evil empire and this company is fantastically overpriced.But when I looked through the S one, it was clear to me that. There’s, it’s not logically impossible that they’re evil, but if you actually look at what they’re saying, and you look at what they’re doing, they, they make a pretty coherent case that they are fighting for. Good. And. Later on. There was more commentary on them, some interviews with, with the founders.And it did actually seem like they thought through all of these objections. Like if you’re, if you’re smart people, if you’re, the founders are people who majored in philosophy, like they’re, they’re these used to thinking about moral issues. obviously majoring, yeah. Philosophy doesn’t make you a good person.It makes you a person with a better vocabulary for explaining why you’re going to do what you want to do. But at least it means that they, they do have this whole, This whole toolkit for, for wrestling, with these issues. And, almost a lack of plausible deniability. Like you, if you know what, what the great thinkers in history have said about things like, is it moral to help, Bad government do something that is going to cause less harm than if you didn’t help them, but they’re still doing something bad and maybe you’re enabling them to do more.And maybe the more that they do will be worse. Like that’s, that’s stuff people have been thinking about for a couple thousand years now. So, they had been thinking about that and, I was actually really happy with the feedback on the volunteer piece because a lot of people said this. this explains what this at least gives like this counter view to the view that they’re evil.But I also had people ping me privately say, yeah, I worked there and this is, this is actually right. Like we, we do believe we’re fighting the good fight. that there’s a lot that they can’t say publicly, in part, because they’re working with the government and like a lot of that stuff should not be publicly disclosed, but, that, that was a piece that I made public.More because I thought that it actually contributed to the overall discourse, but a lot of the, a lot of the stuff stays paywalls and, that’s, that’s something that if people want to pay for it, they should. And in a lot of cases, like the vast majority of people do not, they sign up for the free version.They don’t sign up for the paid version. That’s fine. And, I’m happy to write for a large audience and get interesting feedback and be an interesting people. even if there’s no monetary component whatsoever to that,Nathan: [00:39:39] On the ratio of free to paid and then also the price. So you went with $20 a month or $220 a year. I’d love to hear. You know, is everyone’s so many people are like $5 a month and I’m like, no, no, no. Or more like, raise the price for newsletter. It’s not, it’s not cite there. but what went into choosing the price that youByrne: [00:40:00] So I originally kind of newsy high quality publications that were at 10. And I saw sinus ism was at 15 and Sinocism struck me as very close to what I’m trying to do, which is provide a lot of depth. and be something that you, you could read on your own, but you could also expense at work.either one would make sense. So I basically just said, I’m going to let these people do their, do my research for me. And since cynicism was near the top of the, the meter board, I just went with that. And then, I decided just to see what would happen if I raised the price of it. So raise the price from 15 to 20, I made a big production about it.So I told people two weeks in advance and then when we can advance them the day of, I was like, you need to subscribe by 11:59 PM Eastern time, or it will permanently be. And then, you know, told them. How much they’re saving, if they subscribe now, sub-sect does grandfather people in, which is a huge relief to me because I remembered hearing that somewhere and I wrote it in the newsletter.I was like, if you’re a subscriber, don’t worry, your grandfather did. And you have nothing, nothing you’d have to do. And then I tried to find where on the substantive website, it actually said that, and I couldn’t find it. And I was like, I’m going to be Venmo showing hundreds of people $5 a month every month until everyone turns out.And then I found it in that help page somewhere. So that was a huge relief. Anyway, I did that. I sent the, my one actual sales letter to just the free subscribers and it was fun to write. I used to be a copywriter a long, long time ago, and I always liked these bombastic sales letters. And, I occasionally like reading them, like, I like reading Ramit and his sales letters on money and personal finance and career and stuff.And I know I’m being sold to, but it’s actually enjoyable and he’s really good at it. So I learned a lot from that. I did the sales letter, many thousands of people opened it and plenty of them converted exactly. One person unsubscribed and said, I didn’t like this. It was really salesy, but he wasn’t even mean about it.He was just like, this isn’t really what I wanted. And I was like, that’s fine. So, that works out there’s there are these, Metta maltheisms. So. Malthus talked about how, when the population grows, you end up with too many people for your food supply. So it always stabilizes at near starvation. And there are a lot of other phenomenon life like that, where if you’re not experiencing problems, you could be going further.So, the, the Peter teal quote is if you’ve never missed a flight that took your life in airports. And I think with newsletters, it’s, if you’ve never gotten a nasty email or even a slightly peeved email from someone saying you’re really selling this too hard, You’ve never gotten that you are not selling nearly hard enough.And I also think there’s, there’s this, near-moral obligation to sell your stuff. Well, if you think it’s good. And I think that part of why people are reluctant to sell is imposter syndrome or maybe some form of cowardice. It certainly is a reason that I’m sometimes reluctant to sell or has happened in the past.And, I it’s, it’s a way to signal that you actually believe in what you’re doing. If you’re willing to slightly embarrass yourself with a sales letter and with a sales pitch, and you were willing to pull all the little copywriter tricks, you know, the bullet points and the endorsements from, from celebrities or e-celebrities all of that stuff.Here’s what you’re getting. Bam, bam, bam, bam, bam, all that stuff. I think there, there are people who can’t get away with it and there are people who can get away with it, but don’t try it.Nathan: [00:43:31] I think that’s a really good point that, that, that you need to be pushing it to the point where at least some nber of people are complaining. If no one is complaining at all, then you’re, you’re not charging enough. You’re not, you know, something like, you’re not confident enough in your own value. Because, yeah, there’s always someone to complain on the internet.It’s if you’ve managed to find this perfect community, then, then yet you’re selling yourself short. now I want to get into your writing process because five newsletters a week, and you’re officially promising three, which is good. Right. We’re under promising and over-delivering, I think there’s something.You know, you could, take from that, but like Tyler, Cowen has this thing that talks about like, what’s the Tyler Cowen production function. Like how does he, he’s one of just an incredibly prolific, creator, like what makes him tick? What, like, how does all the work that he does happen? That’s the question that I have, you know, just watching all of your stuff.Like what, what is your process? And then, you know, starting from. What sparks the inspiration to all the way through to being able to publish, you know, a detailed well-researched article, every Workday.Byrne: [00:44:43] I’ve always read a lot and I’ve gotten more systematic about it now that I have the defacto daily deadline. So I have lots of RSS feeds, probably a hundred. I don’t really keep track as a lot of them. It’s someone who publishes once a month, but it’s always good. And then for some of them, it’s, this site publishes 50 or a hundred articles a day.Most of them, you read halfway through the headline and it’s garbage, but occasionally you’ll see something interesting. In terms of what I read of, I try to read one major business publications business section from each of the 10 largest GDPs, the countries with the 10 largest GDPs. I think there’s one or two that I’m missing, but I just try to get this cross section of business stories that are going to be local to one place today, and then they’ll get big tomorrow or next week.a lot of blogs, I read, the major tech blogs, and then there’s this long tail of things like, Industry specific sites. So someone like a semiconductor digest or ad exchanger, finance sites like pension investment online, a lot of these more niche ones where I’m done, probably not reading every single thing that they post, but, I’m looking at the headlines and I’ll often find something worth diving into, when I come up with article topics, the structure of the newsletter by the way is, It’s one long form piece, only around a thousand words, but it varies a bit.And then, maybe half a dozen short links with commentary. So. A lot of the things that I read, they end up going into that is short links with commentary thing. And that’s what I definitely not trying to do is be one of the morning news dp emails, like the deal email. Cause those are, those are really valuable for knowing everything that’s going on.And I try to write for someone who either a. Already gets deal books. So they don’t need one more of those emails and there are dozens and dozens of them, or be someone who actually doesn’t care what’s going on. They care about what’s. What’s interesting. So it’s either, and this is why it’s called the diff it’s from the, the, the Unix function.So I’m, I’m dipping against, like I’m trying to diff out the, the, the interesting stuff and the inflections from just the general flow of news. So I try to, I try to extract that stuff and, be your value added for people who are already immersed in this stuff all the time, which is like a lot of the finance people who read it or to be what interesting thing happened today to someone who’s not reading the daily news, for the longer form pieces, there, there are a lot of ideas that sort of vaguely linger in my head for a while.And then. I eventually write something about them or there’ll be a pattern where I noticed that I’ve, I’ve seen five different instances of this same kind of thing happening. And so I should write a full story about it. So, one example of that from fairly recently was I noticed that retailers and brick and mortar retailers keep launching some kind of ad business that is adjacent to their e-commerce business.And I was wondering why that was, and I realized that. Amazon did it and did it really well because they have all this first party purchase data. So if you are selling anything, Amazon probably knows everyone, almost everyone in the country who has purchased something like that, or who’s statistically likely to purchase that.So they should be really good at targeting ads. If you look at someone like, target or CVS or Walgreens or someone like that, they actually have a lot of this offline purchase data that’s tied to individuals and their e-commerce position is relatively weaker, which means that their ratio of. First party purchase data to e-commerce data or to e-commerce revenue is really high.So it actually makes sense for them to monetize some of that through ads rather than through selling products directly. so that’s, that was one, one case where there was just this ongoing pattern. Another pretty frequent source of things to write about is companies that are just going public. That’s often the first time that you get this look into the unit economics of a company that people have known about for a long time.And, there’s this tradition where. Company files their to go public and it gets posted to hacker news. And someone pulls out a line from the risk factors saying this company has never reported an accounting profit, and doesn’t expect to necessarily the future and is like, this is a disaster it’s worth zero.And someone has to chime in and be like, well, if you look at their free cash flow, they’ve actually been making more money than they spent for a long time. They just have to appreciation or whatever. But basically having, having a cogent answer to the question of why is this not worthless when the company’s not reporting an accounting profit, or if it’s really profitable, why is this interesting?So, that’s, that’s another source. And then sometimes there are just general trends that I might not have written about or general patterns I might not have written about where I think it’s worth a long treatment. And, that can be, that can be anything from just an economic phenomenon that I know of that, That isn’t talked about that often.So one of my early pieces that I was really happy with was about, this economic law for determining the optimal amount of a resource of a finite resource to extract where the paper was. They went through a bunch of complicated math and the basic argent was your, all you’re doing is saying. Do I want money now or money in a year.And, like, do I want to drill for oil now and have money now or drill oil in a year and a half the money then? And that, that depletion rate is determined by how much you expect the price to go up. So it ultimately comes back to interest rates, but. If you, if you actually try to operationalize that the interest rate that you should think about is not just what does a treasury bond yield it’s actually like, what, how much do you value money right now versus in the future?And what that means is that in a lot of really unstable countries, it actually makes sense to drill way more or drill for way more oil than you otherwise would because. If you are, I don’t know the dictator of Venezuela, you don’t actually expect to be in power in 20 years. So even if you think oil is gonna go way up 20 years from now, you actually want to drill for it now and spend the money on tanks.Venezuela is a special case because they also are not currently able to drill for oil at all. And, so there’s, there’s another way the model breaks down, but I thought it was an interesting model to explore because it’s. It’s useful directionally. And it’s actually a really elegant approach for thinking about the question of depleting a finite resource, and it’s always wrong.It never actually describes reality, but the, the gap between the model and reality is actually instructive. And I think that’s, that’s one of my meta themes is that there are all these interesting theoretical models or interesting analogies that are imperfect, but the ways that they’re imperfect actually tell interesting about the world.Nathan: [00:51:30] Yeah, that makes sense. So then, so you’re doing all of this research and finding those, those trends. what does it look like when you’re actually sitting down to write? Is that, are you dedicating, you know, an hour, three hours, five hours a day to writing what’s what’sByrne: [00:51:45] I don’t keep great I, I will spend a lot of my day reading, reading books, reading news articles, reading sec filings and academic papers and things. And then at some point I realized that I should actually start writing. And so I started writing, but I kinda zone out and I’m always surprised when I look at the clock, when I’m done writing the newsletter with how late it’s gotten.So, it, it is a couple hours of writing, but. I think some of it is like trying to get in the zone and that’s just, struggle with distraction and then eventually to start writing. And that just happens pretty smoothly until I’m too tired to go on.Nathan: [00:52:24] Yeah, it sounds like you’re, I mean, you’re doing the research and reading until the article becomes really clear what you want to write becomes clear. And then, then it’s the transition to getting into a focused mode to write that.Byrne: [00:52:38] I used to, before I was writing all the time, I did have a backlog of ideas and I slowly worked through the backlog. And for a while, I was at the point where I never knew what I was going to write next. at this point I do sort of have a backlog, but it’s more like, So I would have this list of just here are things I want to write about.And then periodically I’d write about one of them off the list. And what naturally happens is you write about the stuff that you can actually get done. And then you don’t read about the stuff that’s going to take you. So, the list just keeps getting more ambitious on average because it’s always like more and more research is required or you’ve got to somehow find this dataset and do the statistical model, or like, I had a conversation with a commenter who was asking, he was talking about how, There was this big trend towards business articles about, what American can learn from Japan in the seventies and especially eighties.so it looks like Japan is nber one. Like what, what are they doing differently? Why are these companies just, just annihilating the U S auto industry? What can we learn from them? But there haven’t been a lot of books like that about China, even though a lot of the, a lot of Chinese companies are competing really effectively.And, in, in cases like conser internet, they, they seem to be well ahead of the U S companies. And, so we were, what, what ended up coming up was the question of in the 1930s and forties, were people writing these like management secrets of Joseph Stalin pieces on like, how can we compete with Russia there?They had, they were this agrarian nation, and now they’re making all this steel and mining all this coal. So, I, I Googled around, I actually couldn’t find anything good on that, but I realized that you could actually write something interesting about just. What was Soviet economic policy like, because the country did industrialize at that absolutely enormous han cost, but they did industrialize, it didn’t hit first world status, but, well, I guess they were second world by that, that taxonomy.But anyway, they, they were a lot richer, afterwards, and then they went through this long stagnation and decline. So I think learning about what. What the Soviets did. And then what was wrong with it is, is something pretty fun. But the sources that I looked into are pretty extensive. So there’s going to be a lot of reading.That’s gonna be one of the, the very low ROI posts where it’s like, I’m going to read three books and write a thousand words in smary, but I’ll probably learn a lot in Bali. Find some useful lessons that can apply somewhere else.Nathan: [00:54:59] It’ll turn into more than one post over the next period of time. It may not be a series back to back, but over the course of a year or two, you’ll pull in trends from that kind of thing. so there’s a huge amount of work that goes into all of this, obviously in the end, the, the effort you think there’s, do you think it matters for say the economics of your business, right.To be publishing five times a week versus say two.Byrne: [00:55:25] I’m sure it matters. I think there’s, there’s definitely room to, to adjust the publishing frequency and there’s actually room to adjust the schedule. Like when one of the things I pay really close attention to is why people unsubscribe and there’s a field that there’s a form they can fill out so they can tell me.And they often do. one of the common things people say is there’s too much for them to read. And especially that it’s too hard to work through the back catalog. If they haven’t been reading it for awhile. And I think that is, that is not really about too much content total. It’s about email being a really good form factor for sending high value content that someone’s gonna read that day.But it’s, it’s really tough to work through an archive of email newsletters. That’s in your inbox, you might have to do some kind of special search, or you might just be scrolling through your inbox. So you’re getting this random assortment of here’s you know, an invite to a zoom meetup that I didn’t go to.Here’s an Amazon receipt. here is an essay and then here’s another Amazon receipt and another essay. It’s just a weird change in context. So. one of the things I’ve been thinking very hard about is switching some of the things I write to a longer delivery cadence, I’m basically working on a book and then having the giving the subscribers access to that book and probably doing four posts a week instead of five and spending one day a week.Working just on the book. probably a good trade. It’s going to be the same level of output, but, I think the final product is going to be something you can actually binge-conse easily. And I think writing, writing for, habitual snackers and writing for bingers is useful because different people have very different approaches to consing information.I do too. Like I, I will have, have times where I’m going back and forth between a lot of different things and reading. Reading little bits of information here and there when I have time and then periods where I’m just going to sit somewhere forfour hourswith a book Nathan: [00:57:18] Right. I think that’s really interesting. Kind of what you’re getting at is what’s the highest leverage, application of your writing. And so if you’re, if you’re looking to reach new people and this is probably why people like Tyler Cowen have done really well, right? There’s a lot of that is going into another book, you know, or Seth Godin, right.We’re into the 22nd book or something, right. That he’s put out because he’s realized it’s the same writing that goes into the newsletter or the blog, or, you know, this idea is just flushed out in longer form, but it’s higher leverage and that it’s going to reach more people. And so, you know, if you keep a hundred percent of your writing for the newsletter, that’s going to have one amount of leverage, which is actually pretty significant leverage, which is why we’re all here talking about newsletters because they have great leverage and they’re amazing.but if you peel some of that off and say, okay, but this is going into. A book that, you know, then you can reach so many more like CNBC is not going to necessarily have you on to talk about the newsletter. But if the book comes out, then they’re like happy to have you on, because that is a format of, you know, authors going on TV tours to promote their book is a well-known thing.And so that would get you a level of exposure that the newsletter wouldn’t.Byrne: [00:58:28] Yep. Yeah, that’s exactly right. That you, you can, you can package content in different sizes, but it’s, in some ways there is just a mental difference between what you’re doing when you write. An essay versus a tweet versus a book that with an essay, you can have this more unstructured approach where you’re, you’re watching stories go by and you’re just grabbing something that looks good and turning it into, a quick story or a not so quick story.But then with the book you actually want to come up with, you have to find that idea that’s actually worth a books or the material. And then there’s a lot of research. So, I am working on a book with a friend and, there’s. It’s like, I’m working on one chapter and stack of books is about this high that we’re going to convert into a chapter in a book and it’s going to be great.Cause there’s going to be a lot that I’m gonna learn. And it’s a, it’s a fun topic. The chapter has a fun time. So I’m, I’m excited about it, but that, that is a really different process because. And part of what you’re doing is, it’s like the newsletter process of there are these themes to talk about and you find different iterations on the theme.So they’re always reading a story through a bunch of different lenses and trying to see if there’s, if there’s some broader trend that this story speaks to or contradicts, but with, with a book, you actually have to select a theme. In advance. And so you have to be, you have to display some definite optimism that there is actually enough material there.And then once, once you’re committed, once you’re actually doing it, I think there are a lot of people who’ve written like 5% of a book. I think that’s like a Rite of passage. If you, if you write for a living or even write for fun, but I don’t know how many people have gotten through two thirds of a book and just given up, I think it’s more likely that you’d like write two-thirds of a book and then.You know, something, some catastrophe happens and that’s why you don’t finish it, or whether it’s your, her drivers yourself. at some point it just has moment that you’re going to get it done.Nathan: [01:00:22] Yeah. Yep. That totally makes sense. Well, as we start to wrap up, I’d love to hear some of the metrics that you track in your newsletter. Like what, what do you pay attention to? And maybe in the early days, what was the thing where you’re like the nber that you got to and you said, Oh, this is going to work.This is a real thing, you know, I don’t know, a couple months. And what did success look like? And then now what do you track.Byrne: [01:00:43] Yeah. What I started at $15 a month. I raised the price to $20 a month and there was this whole roll dr roll. So a lot of people signed up, so this huge increase in subscribers and then midnight came around and I just hung out next to my computer for awhile.And then I got a confirmation that someone had paid $20 a month. And I was like, okay, people will do it. They won’t feel ripped off if they missed it, they think it’s worth it at 20. And I’m very happy with that. So. That was one that’s, that’s a data point, not, you know, not, not an actual metric, but, the main thing I look at is just the nber of paid opens for the newsletter, because that to me is the most forward looking metric because for someone to stop reading it or for someone to unsubscribe, they probably have to stop reading it first.And so what I should care about is are people who are paying for this in the habit of reading it basically every day. And that’s, that’s a high bar. That’s a, that’s a nber that has gone up over time. Open rates. In my experience so far, they have tended to trend down very slowly over time, just because, among other things, the first couple of dozen people you will get are probably people who know you.And in some cases like there are some newsletters where if I’ve read it on someone’s blog and then I get the newsletter and I realize it’s the same thing. I will still click on it because I don’t want their open rate to go down just because I’m too big a fan. It’s just, it feels like some combination of like this, the minim.The minim effective dose of friendship and some level of professional courtesy. So, when, when you have. Thousands and thousands of people in the free list. obviously most of them are not your friends. a lot of them become friends, but, a lot of them, it’s just one more, one more newsletter they get.so over time, those open rates do tend to trend down, but I do pay close attention to that. And especially, I just want to make sure that I don’t get in this trap of writing for a subset of the audience and having people who don’t open it for a while. So. I will periodically spot check subscribers, see if anyone has just stopped clicking for awhile.And if I know that they, someone who works in FinTech, they signed up because I read about a firm, they stopped clicking for a while. I’ll look back and see, did I, did I just stopped writing about FinTech because it’s something I write about, but maybe not something that I write about in a given month. So I, in that case might go back and try to figure out what, what I should bp up in the priority queue.All their stuff. I pay attention to. I, I pay pretty close attention to the churn rate as well. And, Stripe has really a really nice interface for looking at that. So I, I tried to calculate it manually and then realize Stripe has done it for me. Great.Nathan: [01:03:29] What’s the, if you don’t mind sharing, what’s the churn rate, like a monthly turn on your newsletter.Byrne: [01:03:33] Monthly churn right now Okay annual cohort is very different, but a lot of them find out almost a year ago. So we’ll see if they’re still happy with me.But, yeah, and it’s like it’s higher in the first month. It’s lower.After that, the older cohorts are totally misleading for the same friendship reason. Like my mom’s probably not going to unsubscribe from my newsletter. So I don’t, I don’t pay attention to my very oldest cohort, but the newer ones, it’s, it’s pretty consistent that like, the retention rate is like 92% after the first month.And then, retention look better month about after that.Nathan: [01:04:09] Yeah, I think that’s really good. So many content businesses from more of the internet marketing world, you know, when they do a paid membership or something like that, they’re going after recurring revenue because they see SAS companies do it. And then. You know, then they run into monthly turn rates of 10, 15% or more.and so it’s, it’s really exciting to see as paid newsletters have taken off that obviously you have to deliver a lot of value consistently, but we are seeing those churn nbers, you know, tend to be like in the lower single digits rather than, you know, what the really salesy, you know, internet marketing community had before of the really high trend nbers.Byrne: [01:04:46] Yeah, and it it’s, it’s definitely going to vary from newsletter to newsletter. Like I could imagine someone, if someone is writing a newsletter, that’s really topic Specific and they are, they’re just, they have a narrow beat and they’re going to relentlessly cover that. Then I would expect their churn rates to look really, good over time Cause a lot of the readers are reading this as part of their job. Whereas if you touch on a lot of different topics, you might actually expect to have a higher churn rate just because you might write something about one narrow thing that is good enough that someone is like, I have to read everything this person writes and then they find out that’s actually not what you write about most of the time.And I try, I guess, T There is always this instinct. every time I get an unsubscribe, I’m like I could have saved this person from unsubscribing. Like I, if only they had called first, I could have explained what I’m doing and why it’s good for Nathan: [01:05:33] I have another post in the queue. That’s just about to come for them.Byrne: [01:05:36] But then a lot of people subscribe for somewhat random reasons. sometimes people subscribe for a somewhat-random reason and then they just turn out to really like the content like there. Since I try to write about things that have these weird parallels. Like I use a lot of finance metaphors to talk about tech companies and use a lot of tech-company metaphors to talk about finance.because of that in a lot of cases, it’s, it’s close enough to between the two fields that someone from tech might say that this is the only finance newsletter they read. And then someone in finance might say, this is the only tech newsletter. They read Substack categorizes it as a technology newsletter, but it’s.It’s more of a generalist newsletter, although there is also a very good newsletter called The generalist.Nathan: [01:06:19] Yep. So I’m going to have to have a Mario in the show cause he’s, he’s, fantastic. And he’s seen a lot of really good growth. I was just thinking about it cause I come at it from the technology space, you know, running a software company, but I enjoy reading it cause my, my brother’s a chartered financial analyst and you know, and so I’m always like, Oh, he would love this, you know, it’s that sort of thing of like, now I understand what he was talking about at, you know, don’t know, Thanksgiving last year or something like that.well, I think, that is plenty for us to cover today. Thanks for, thanks for joining me. Where should people go to subscribe to the newsletter? I follow you on Twitter, all of that stuff.Byrne: [01:06:56] Wonderful You can find me on Twitter, just search my name, @ByrneHobart, B-Y-R-N-E.Nathan: [01:07:08] Well, thanks for joining me and I hope everyone subscribes and, yeah, we’ll talk soon.Byrne: [01:07:14] Fantastic. Thanks. 

Dan Runcie is the founder of Trapital, the newsletter that breaks down the business of hip hop. We learn all about his favorite hip hop artists, of course, but he also shares what indie creators can learn from the world of hip hop and so much more.Having switched from a lucrative paid newsletter to a consulting business, Dan explains the thinking that went into his new business model, and what it means for anyone trying to monetize their newsletter.Dan shares his opinion on Substack—the out-of-the-box newsletter service that seems to be everywhere these days. You’ll find out why Dan started Trapital on Substack, and why he later switched to ConvertKit.You’ll also learn unexpected insights from the world of hip hop, including lessons indie creators can take from Beyoncé’s sales funnel, and why Master P’s cutting-edge albums in the ‘90s show that consistency might just matter more to creators than quality!Links & Resources Substack ConvertKit - Email Marketing for Online Creators Ghost: Turn your audience into a business Blog Tool, Publishing Platform, and CMS — WordPress.org OnlyFans Dan Runcie’s Links Sign up for Trapital Twitter: @RuncieDan Instagram: @RuncieDan LinkedIn: Dan Runcie Episode TranscriptDan: [00:00:00] If they’re using Gmail or using any other service, they see my face in the icon come up, they see my name there. And it’s a familiar thing where it is coming from a person. I want to make sure this reads like an email you would get from someone, not just like a marketing email. So I try to make sure that even though I am sending the email, it’s not just the straight copy from the essay, they are getting something that reads like a note that they would get from a friend.Nathan: [00:00:33] In this episode, I talked to Dan Runcie who runs Trapital, which is the newsletter that breaks down the business of hip hop. He’s really fun to talk to. We learn all about his favorite hip hop artists, right. Specifically what indie creators can learn from the world of hip hop and so much more. So let’s dive in.Nathan: [00:00:50] Dan. Welcome to the show.Dan: [00:00:51] Nathan, thanks for having me.Nathan: [00:00:53] Yeah. Well, I want to dive right in. You have a love for specifically the business of hip hop and I would love to hear from you where, where that started.Why. You know why you care so much about the business side and, what brought you to this point?Dan: [00:01:09] yeah, for me, the love for the business of hip hop really started with loving hip hop. I was pretty early on with gravitating towards this culture and. It was deeper than music. I mean, I remember elementary school. I was really getting into different artists who were the people that are making moves, but it’s also the people that were making movies behind the scenes.Right. I was very interested in the persona of someone like a show ignite or someone like a Puff Daddy and the people that were both being very deeply involved with what was happening. But. Pulling the strings and making things happen and all of the criticism and successes that both of those people achieved.And I think as I continued to grow up, seeing what that was like at the time, I never truly saw that as a career path for myself, but I was intrigued with it. So it was almost like a hobby and something I pursued and kept up and would always talk about with friends pretty much all through life, but it wasn’t until.Let’s see, six, seven years ago. And this was when I was in business school. We were doing case studies on all different type of topics. And one of them that stuck out, we did this case study on Beyonce. He had just released this surprise albno one had done albums, surprise albums like that at that particular timeframe.And it was this huge marketing case study on how these things happened. And it was a case study that was done by Harvard business school. It spread across to other schools. And that stuck out to me almost like a reminder, like, Oh, Hey, you know, this is something that is huge. And. It stuck out for a few reasons.One, the topic, the subject matter, I’ve been a Beyonce fan since the Destiny’s child days, but second, it stuck out to me just how big of a deal that case study was, how it was from a business perspective. And there weren’t that many articles or breakdowns that were talking about hip hop artists or.Artists in entertainment that we’re doing and making the same type of strategic moves that other industries were making in the type of jobs that I was working in and was playing into working thereafter. So for me, it was really an opportunity to look at that. And that was how I had started doing some freelance writing on the side.Started a blog. It was a personal endeavor just to explore hobbies, my own interest topics that snowballed into publications, reaching out where I started writing for them. But then that snowballed again into writing for more and more reputable spots. And then eventually I saw where media was going. I saw hip-hop’s continued rise and said, you know, I have an interest for this.I clearly have some skills that ability to convey these thoughts. Well, let’s merge these two together and started diff publication focused on the business of hip hop and that CellTrak capital was born.Nathan: [00:04:05] Yeah, that’s awesome. So I’m just imagining, you know, you in elementary school with the love of music, but then you’re actually diving in like, You know, when, when something happens or when someone makes a move, you’re diving into the story behind that. Are there any early ones that really stand out to you that you know of an artist making some move where you’re like, wait, Whoa, what was the deal there?Or that you were fascinated to hear every little detail about.Dan: [00:04:31] fascinating. One to me when I was that age was Master P So I remember this was around the time where I was really starting to buy CDs and I bought a single. Of make Em Say Uhh so not even just the alblike the single, I just had like one side and then maybe like a B side album with it. And I played that single.I don’t even know how many times. And That stuck out because master P wasn’t just an artist that had this record label behind him, his whole business model. And how he went about just running and being so popular for that stretch in hip hop was so monumental for people across the entire country. He was putting out an album from him and his group every other week.And. They did not go on tour at all. During this stretch, they just monetized their ability to market extremely well, made sure people knew there was a style and a cover of what that No limit album looked like. There was a distinctive sound. And to be honest, even if the music itself wasn’t always the best they mastered the art of branding.So when I think about that fast forwarding that 20 years now, when you hear all people in content, talk about how. You know, it’s better to be consistent. And sometimes that consistency may be more important than the quality master P is always one of the first people I think of with that. that isn’t necessarily a knock to him.It’s just seeing how so many of those lessons from hip hop can translate to how media and content and so many things in the current world of the landscape operate Nathan: [00:06:09] Yeah, that’s fascinating. And I think we’ve seen that, you know, all across the creator ecosystem of people who show up consistently, or really do it in a novel way, you know, like that’s crazy to think of. I mean, that’s almost the level of an author releasing a book every couple of weeks or, you know, every month of, so people they go away for a long time and like, you know, two years later they come back, like, this is my album.And he’s like, no, like this is the creative process. Like let’s go and we’re as much marketers as, as anything else. what about on that side? Like, I think so many creators. Are stuck in this world of like, I am a creator. Like I make great art or over here, they’re like, no, I’m a marketer. You know, I, I do business and I feel like in hip hop, they just merge that so well, right.Of saying no, the business and the art, they go hand in hand. Do you have any favorite examples of, artists who have just done that really well?Dan: [00:07:12] Yeah, I think with the best example, I always go back to it’s an easy example, but Daisy is still one of the best I’ve seen that has done this so well, he’s not only. Many people consider the greatest rapper of all time, but also the most successful businessperson. He was the first true billionaire to come from hip hop.So much of just how he learned from how the game worked for him. Things didn’t always go his way, whether it was how his early partnerships with Rockefeller or the people that he was working with at the time, there are plenty of things that went well, but plenty of things that he learned from, and then.By how he was able to build future businesses like rock nation and the joint partnerships and the ventures he’s able to make since then truly show the evolution of someone that has learned the craft evolved, but has also incorporated so much of that into his lyrics. You hear different Jay Z albums.There are snapshots in time for where his mindset was at that particular timeframe. And that’s always been the most interesting, I think a lot of this. Rubs off or not necessarily rubs off because I think it probably rubbed off the other way, but a lot of this, you could see with Beyonce as well. I think in a lot of ways, she was a bit.Earlier, in some regard, in terms of how he was focusing on certain things, whether it was the visual content of her work and having that incorporated, having the messaging come in there. But yeah, I really think of the two of them as people who both incorporated how they were changing their business strategy.Over time, how that shifted, how they went about creating their music and the actual content of their music. So it’s a bit of this, flywheel type connection where people see what they want. Right? So when you see them having a performance somewhere in or filming a music video, somewhere like the loop that they did a couple of years ago, it all stems from that same type of place that how they generally perceive themselves and how they want to operate in business, which has always been intriguing to me.Nathan: [00:09:19] Yeah, that makes sense. So you have, like, I always think of you as having a foot in two worlds. Right. One of the business of hip hop and then the other in this like indie creator space of, you know, you building an audience, figuring out how to monetize it. everything else before we dive into more of your story, I’d love to hear just some, some of your thoughts or observations on what indie creators, you know, anyone growing their newsletter can learn from the world of hip hop.Dan: [00:09:49] This is one of the things I really enjoy about the work I do, because there’s so many things I’m reading or things. I see—whether it’s things that happened decades ago or things that are happening right now—that are so relevant to this indie creator space. So right now I’m in this space where I am running a newsletter, running a podcast, and it’s my job to help grow these things, but not just to grow them in any particular type of way.How do I attract the right. Audience. So who’s the persona, who’s the type of person that would be interested in triple a content. How is this going to help them? What problem is it solving? And I think that a lot of artists think of themselves in that same way. They understand that there’s a particular niche that they’re trying to hit.And there are so many tools that they could use. In some ways they’re using a lot of the same tools that. indie creators are using in order to help grow. Right? So many artists have their email lists. They have their community of super phone numbers that they’re texting people. They have their social media, so they have their own funnels in terms of how they are attracting customers, attracting fans.And they funnel down to that type of perspective, artists, or indie creators rather need to do the same. One of the more popular visuals I had drawn in a recent. Case study I’d written for Trapital was this funnel for Beyoncé I’ve just mentioned her a few times in this interview, but it’s, what’s relevant is funnel of Beyonce of just how her.Big media appearances, whether it is a Superbowl performance an interview her being in a big movie that makes a billion dollars, like the lion King, those are her top of funnel. Right. And then how that helps spread awareness to where she can then sell products that are a bit more on the expensive side, like Ivy park, and then at the furthest end down how she can sell VIP concert tickets and other expensive experiences.I think that most indie creators also have their funnel where they’re like, okay, how do I attract people to find out about me in the first place? And then after that, how do I have, or how can I get people to subscribe to my podcast, subscribe to my email list somewhere I have more of a direct connection.And then how can I go about selling them certain. Products or services that can help my bottom line, but then can also help serve them. So, So many of those parallels run true, and I think that’s how that’s been reinforcing. And I think so much of that is applicable, especially in hip hop because the artists themselves are multihyphenate, they are expanding in a bunch of different areas.And I think in hip hop specifically, there’s a bit more of that hustle mentality that you see that makes them a bit likely to expand into different areas.Nathan: [00:12:39] yeah. When I think that funnel makes a lot of sense. And just for an example, From what my funnel is. And I’d love to hear, you know, some of you like, even this podcast, the clips that we’re doing on social media, you know, the really short things to get out there that is our top of funnel. It may not be the same level of appearing in lion King, but that is the same.Like I’m just going for awareness at that point. It’s not even about trying to get the subscriber. It’s people seeing like, you know, the clip pop up and then have a little bit of detail about, art of newsletters or the things that I’m interested in. And then from there, after they see them a few times, then it’s like, okay, well, I guess I should listen to the full episode, you know, and diving in getting someone to a listener of the podcast.And then the next step would be the, the newsletter list. And then in a previous life, that would be, you know, books and courses that would follow up next for me, it, you know, in the current life, it’s for them to start their own newsletter and, and build and grow that on ConvertKit. so you’re absolutely right.You have to think about, okay, what’s the thing. Where I’m trying to get them from, you know, having heard of Beyonce or having not heard of, to having heard of Beyonce, having never heard of Nathan Berry to having heard of it, heard of him. And so I’d love to hear for you, you know, what’s the, what’s that top of the funnel and where does it break down from?I’ve no idea. Never heard of trap. It’ll never heard of Dan Runcie into like all the way through the business to, you know, you earning a living as a creator.Dan: [00:14:07] right. So the top of the funnel, that’s the awareness piece. How can I get the people that are not aware of Trapital right now to realize that so. Think about where are the type of places people who would be interested in Trapital are probably spending the most time. So if you are interested in hip hop, whether you are someone that works directly in this music industry, you work tangentially connected to it in some way, or you’re a general fan of it.You are probably going to be spending your time consuming. a Fair amount of media, whether that is through Twitter, through Instagram, through LinkedIn. And now there’s enough of the core audience in those particular fields that are truly interested in hip hop that are that target core customer for Trapital that are reading tweets on Twitter, seeing people that they follow.So I use social media as my primary top of funnel. if I am posting tweets on a regular basis, I know there’s certain things I want to Cover in terms of topics. So I want to at least have something to say or a topic about some timely events that are happening right now in hip hop, or I will also share some evergreen thoughts.I may have about a topic that may just keep coming up in the business of hip hop. So that is my top of the funnel. I probably focus most on Twitter, but I try to follow that 80/20 Rule where I have 80% of the focus in one particular social media app, just to put my primary focus there. So I’m not spread too thin, but also have a little bit of focus into other areas so that if something takes off, I’m not completely left out of it.The further.Nathan: [00:15:51] Well, let’s say a top of the funnel for a second, because you mentioned having things, you know, on social media that are really relevant. So I see you like w when there’s a breaking story developing, you know, I, for example, one that you’ve been talking about a decent amount lately, cause it is just happened in, you know, his little way in selling, young monies, masters, you know, and that being such a w what was the number on that?A hundred million dollars, So, yeah, like dive into that for a second of taking something that’s just happened, you know, and how you’re, you know, writing content, having your perspective on it to go out on Twitter.Dan: [00:16:31] So when something like that time, we happens in the news. There’s normally a few things that’ll happen. One, a bunch of people will start reaching out to me being like, Hey, what’s your thoughts on this? What’s your thoughts on this? And it’s almost like a thing where okay. If I have. A ton of people reaching out.Then this is something that many more people are probably going to be interested in what my opinion is on this. So I normally try to make sure that I’m not just reporting facts, I’m providing some other deep type of insight where it’s thinking about something else that happened historically, or thinking about how this impacts or broader trend.So that relates in two ways. One. young money was a imprint at a time of cash money, which was a record label that Birdman who was a close friend and has had an on-off relationship with little Wayne at the time had started back in the nineties almost 30 years ago. And they had done a pretty landmark deal where they had able, they were able to maintain ownership of their masters.They were able to get a very lucrative distribution deal. So I knew all of those things happening. And I said, there is a narrative here about how this story connects to what just happened, because it’s almost a reversal of what we’ve seen, where. A really good deal happened from the hip hop record label, partnering with the, one of the biggest music companies in the world.And then we just saw the opposite thing happened where Lil Wayne sold one of the valuable assets he had for a very cheap price relative to what we’ve seen in the marketplace. So there’s that. But there’s also this broader trend around ownership that we’ve seen and heard more about, especially in hip hop, more artists are being much more vocal about wanting to maintain their assets that they have, whether that’s their sound recordings, which in most cases, their masters or their publishing, so on and so forth and not necessarily making a partnership with a record label.So being able to bring these thoughts together in a clear and concise way and. Posting and sharing insightful tweets helps offer some of that context that isn’t necessarily there because this is where also one of the reasons why I started travel, there was so much focus on the, what that was happening, what happened, what is the biggest news that happened, but there was so much less talk about, okay, what does this mean?Is this a good deal? What are the other considerations? How does this fit into the broader landscape? What is the nuance? So being able to have clear and concise thoughts about that, whether that is a tweet, whether that is a Twitter thread or some other type of post that then can get awareness with the people that are already following that can be shared retweeted.And so on and so forth. So because of the way that Twitter’s algorithm works, it’s also likely to find other people that would be interested in that type of story. And because of that, that then helps grow that overall funnel. That doesn’t mean all the people that liked or retweeted are necessarily going to subscribe and become an Email subscriber to Trapital but similar to how you kind of shared with your newsletter. If they see that they then see, okay, who is this person? Dan Runcie sounds like he has some strong opinions on this. They scroll through my feed. Oh, okay. He had something interesting to say about, this deal that happened a couple of weeks ago.He had something interesting to say, about all of these livestream music festivals. Okay. Maybe a week later, you see another tweet of mine coming to your timeline. And it’s like, okay, now I’ve seen a couple of these. Let me go subscribe. And then maybe, you know, a week or so later, you see me say, Hey, I’m going to send out a newsletter.I’m going to cover these topics. Sign up here. If you want to get it, I’m going to send it out later today. There You sign up and then you start to see the email funnel. You could read a few of my past essays and that’s normally how it works for a lot of the people that end up subscribing. But I also know that there are people that are off of Twitter I also need to be able to reach as well.So it’s trying to use that similar type of mentality in other platforms. And I think that has served me pretty well.Nathan: [00:20:35] Yeah, that makes a lot of sense. There’s two things that I heard in there that I want to really highlight. One is the deep industry knowledge, because so many people are saying like, Oh, this happened. And then this other thing happened. And so as a creator, being able to tie that back and say, this happened, and it’s interesting because here’s the whole backstory, here’s the trend, you know, or here’s how it’s opposite of what happened in the past or here, the continuation of the trend.There’s a lot of news, you know, news headlines. We can have all of that. And what you’re offering is insights and that’s, you know, what other people don’t have the deep knowledge or the time or something like that. And so I think we’re seeing that with newsletters all across the board, where at first glance glance, we’re saying like, okay, newsletter, you know, there are people are highly in the news part of it and saying, Hey, that’s covered already.You know, the headlines are written, you just follow the right people on Twitter, you know, read CNN or whatever industry publication. And like, you know, you know, what’s going on and what all these newsletter creators are finding like you is that there’s a whole group of people who say like, no, no, no, I want, I want the narrative behind it.I want to know. The deep insights and there’s quite a market for that. The other thing that you said that you’re doing is. In addition to, you know, as we’re bridging that from top of the funnel into now subscribed to the newsletter, you’re not just saying, you know, every, every week or every month, a tweet of like, Hey, make sure to subscribe.You’re saying this story that you’d be interested in my take on this thing that just happened is going to be published, you know, three hours from now later today. Subscribe, if you want to get that now. In most cases, they could go to your site and it’ll be published there publicly by having that specific call to action, you know, where you’re like, Oh yeah, I want this thing that I know is coming soon, is way stronger than just subscribe to my newsletter or some generic giveaway, because then not only am I subscribing, which is goal number one, but two now I’m waiting for an email from you.I’m like yearly, like Dan said he was going to get it out today. Like, is, is that, is that coming? You know, and that’s such a great place to be.Dan: [00:22:45] Yeah, I agree. And I think that it’s so easy to just say, Hey. Subscribe, Hey, just subscribe or please subscribe to my newsletter. I really wanted to be able to make sure that I was offering some type of value. And even though that is value that they could get outside of subscribing to the email newsletter, it still provides that connection to be able to provide some type of lead, provide some type of incentive that they are like, Hey.This is just the tip of the spear. That in many ways is how I treat that top of the funnel or how I’m communicating information in social media. This is the tip of the spear. It’s enough for me to be able to use this format, but in order to really get the depth of it, that you can. Subscribed to the email list, you’re able to get a bit more insights and then it’s a bit more of a relationship, right?If they’re using Gmail or using any other service, they see my face in the icon come up, they see my name there. And it’s a familiar thingwhere it’s like, I’m intentionally using the name, Dan Runcie that they’re getting from and not coming from travel. Because even though I am a. No solo person, plus a few freelancers running this.It is coming from a person. I want to make sure this reads like an email you would get from someone, not just like a marketing email. So I try to make sure that even though I am sending the email, it’s not just the straight. Yeah. Copy from the essay, they are getting something that reads like a note that they would get from a friend.It’s a quite detailed note that has a lot of insights and comparisons, but it sounds very familiar and that’s intentional with the language and the texts that I use with trappable.Nathan: [00:24:30] Yeah, that makes sense. I have this friend, Levi Allen. Who’s a filmmaker in British Columbia. And in his videos, he often said like, he’ll just start his videos and be like, Hey friends, you know? And he has just has this like, charming way of, you know, where you’re immediately just feel it like, you know, Oh, we are friends, you know, like you’re immediately in there instead of having this feeling of like, let me broadcast to all of my subscribers on YouTube or, you know, like dear masses out there, this is my proclamation, you know, it’s just instead this like personal feeling.And so I love that about your work of like, yeah. Yeah. I just have this friend named Dan who happens to know all the insights about the music industry and he just drops them in my Dan: [00:25:11] Okay. Right. And I think with that too, one of the things I try to intentionally do is make sure that the tone of Trapital comes across relatable. There is a way where this can be written with much less. I don’t necessarily want to say flavor, but there’s a way this can be written where it doesn’t have as much relatability to how hip hop actually is running, where you’re just trying to come at it from this pure business perspective.So I want people to know this is coming from a place where. It understands the business, but it also understands the culture and the analogies and all those things, which make it a much more enjoyable and approachable read. Because I think a lot of us that are indie creators putting out content realize we’re just not in the business of trying to educate if we are trying to hold attention.And there is an opportunity for the content we’re creating to be able to. Entertain or offer that value it’s in our interest to be able to do that. I felt like there was enough about my tone and the comparisons and the way I’m writing it, that that can come across in an effective way. And that’s been one of the things I often get complimented on with the newsletter and the essays specifically.So that has also been an intentional part of Trapital’s tone.Nathan: [00:26:36] well, I think part of what I imagined it being is like that first HBR case study that you read, you know, when going to business school, being like, Oh, wait, people care about the music business. Like I could, you know, I could write about that. It’s almost like as if you were hanging out with the people who wrote that case study afterwards, and they’re like, they wrote the official thing and like, this is all of it.And then. It’s that plus, you know, they’re taken like this didn’t make it in to the, the full thing or we had to stay very, you know, I don’t know, proper official, that sort of thing. And so now when you’re hanging out afterwards, they’re like, Oh, but this was super interesting, you know? And so you’re getting more of their opinions rather than just the straight facts.Dan: [00:27:22] right. And I think a lot of that came from those conversations I had with people and like how we would naturally talk about things, thinking about how let’s say I’m talking with a friend and we’re talking about door dashes or air B and BS, IPO. We would, we wouldn’t necessarily be talking as if we are wall street journal, wall street, journal journalists that are breaking this down.We would probably be a bit more relatable than that. And that speaks a lot to how we communicate. And I think so much of that translates as well. Whether we’re talking about little Wayne, sell a young money’s masters or Beyonce, partnering with Adidas or Rianna doing a Fenty deal. So on and so forth.Nathan: [00:28:01] Yeah, that makes sense. Okay. Let’s go further down the funnel. so we we’ve covered awareness and we have people in the newsletter list. One thing that you’ve done is you start with the free newsletter and then you launched a paid newsletter back before pay newsletters were cool, you know, and, and then you’ve actually later you shut it down and, and change business models.And so I’d love to hear first, what, what, let’s just start with, what was attractive about a paid newsletter and, and why you started down that path.Dan: [00:28:31] so I started and focused on the paid newsletter path originally because I was pretty focused that that was the best model for travel because it was what I had seen From other people doing this, that was the most successful. So I was trying to, in many ways, replicate that I saw what Ben Thompson had done with Stratec Curry and had actually talked to Ben Thompson, getting his take on how he had built this.And I said, okay, some of that I think relates some of that. It doesn’t relate, but I said, There are enough people that are interested in this culture and rising that even if I’m able to skim off, let’s say 10% or however many of those people that end up subscribing to the email list to become paid subscribers, then that would serve me well.And then that would continue to help the business grow. So I think I was almost thinking about it from a wide net perspective where. That paid product. this was something I was charging at the time $10 a month, $100 a year. And it was essentially for freemium content. I had the one deep-dive essay that was going out to everyone weekly.It was a free essay I had written, but then if you wanted, the more timely updates on the most recent things that were happening in the business of hip hop from the past 24–36 hours. That was what I was sending in those, updates later on in the week. And this week product had attracted a fair amount of people in the music industry, outside of the music industry as well.It also attracted people that had just wanted to support B and CBB successful. And it’s the type of model that could have worked. I. Didn’t necessarily get that 10% of email subscribers. I thought I was going to get, I ended up getting around 6%, so I was a little disappointed from the yield, but then I thought more broadly, there were a few challenges that I had with it.One, I was still in the early days of travel and I really should have spent more time. Building the overall funnel. So really growing my overall top of funnel, as opposed to spending more time shot at events that people that were already in that interest stage to committing to the product that I had, that was at least the product that was at the bottom of my funnel, which was this paid membership to travel and.It was difficult because one, it required a tremendous amount of time to be able to offer what I had already committed to the people that were in the paid membership. And it wasn’t necessarily monetizing Trapital itself to the best of its abilities. I realized that beyond just having people who have an interest in hip hop, there was a super-specific group and niche that could be super served well, by what I was offering, there are the people that are working and making the decisions that are truly taking the business of hip hop to the next level. I’m writing about the types of deals Drake has done and whether or not he should have considered other options.I’m talking about the type of partnerships record labels have made with other, livestream companies or other organizations. Over time, if you write enough and you do well, you’re going to attract the people that are making those types of decisions to your newsletter. So there’s a better way to serve that audience than offering just this general product that was reaching the wide net.And that’s a product that can work. It clearly worked for a number of people. I think it could’ve worked even at a 6% yield with a much bigger net, but. There are better ways to offer products that aren’t necessarily annual commitments or subscriptions that can serve them, whether that is a consulting offering, whether that is a specific type of service or advisory or some other type of practice that you can.What I’ve done specifically with Trapital since pivoting is working more on a consulting and, Unique project basis where I’m helping different companies in different types of ways help bring hip hop to the work they’re doing, whether that is helping with podcast, helping a podcast network and thinking through some development for some projects or helping different, Companies outside of hip hop, but in the electronics or the entertainment space, think about how best they can integrate and partner with hip hop artists.You’re seeing so many people just seeing the type of deals that are happening. So by me using my newsletter as, or using my newsletter as a funnel to help reach those people, it then can attract the people that are working in these industries. And then It can easily start a conversation where we can explore other different types of business opportunities.So that’s been the main way that I’ve done it. And I think there’s plenty of ways to expand on this as well. I think there’s an opportunity for courses. I think there’s an opportunity for one offer digital products that I can offer to help serve the true executives and the Bogles and the people that are making those decisions at Trapital or that are reading travel.And for me, That is a better way, both to monetize trap metal from a time perspective, which in many ways is my most valuable asset, but also from a value add perspective as well. So it was a lot of learning and building the plane as you’re flying it. But I I’ve definitely been humbled and appreciative of how much I’ve continued to grow and learn through this part of that comes from.How much, I’ve just tried to better understand the landscape, but also just came from doing it, realizing what doesn’t work and quickly being able to iterate.Nathan: [00:34:17] Yeah, that makes sense. And the most important thing is that once you have someone’s attention, There’s a bunch of different ways that you can earn money from that I’ve with pay newsletters early on. I’ve been pretty vocal about, Hey, I don’t think that they’re necessarily the best. not that there’s anything wrong with them.I just think that for a new creator or someone gaining traction, they may not be the best way to monetize the audience. So for example, David Pearl, who was on the first episode of the show, he’s got an email list of 40,000 people. I think he could do a very successful paid newsletter. He’s quite prolific.And instead he said, Nope, I’m going to do what he calls the Rite of passage, which is his, you know, very expensive premium course. It’s, cohort-based, he’s heavily invested in these people. I think the course is 2,500 or $3,000, something like that. And it’s generating millions of dollars, per launch of the course, you know, and.And that’s not to say that he couldn’t also do a paid newsletter. He’s just found that this is his monetization method that he wants to do and what works best for him. so yeah, there’s a bunch of different options there. And so it’s interesting to me that I guess two things in, in what you said, one that you chose consulting as the, the way that you most want to monetize right now.So I’m going to dive into that. Yeah. But before we do, what was the reason that you chose to shut down the paid newsletter? And do consulting rather than keep the paid newsletter and add consulting. why have, why go to one instead of two monetization methods?Dan: [00:35:50] time. Tea time was the biggest thing for me, the way that I had structured the paid newsletter, the product that I was offering was something that required 20 plus hours a week in order to be able to create on a regular basis. And sure. The. Unit economics of it can work out. If you have a large number of people, it’s a zero marginal cost product, but it was still a large time for me to be able to do that where you just, I would have needed to have a very large number of people, not just to justify the cost, but also more to justify the opportunity cost of what else I could do.With that time. So it was a tough bullet to bite, right? There was some traction and there was some recurring revenue that would have been there. And, having paid subscribers consistently is a nice thing to have. Even the people that I know that are successful with paid products. It is nice to be able to have that.There is a reason that I, so many companies have been trying to figure out how best to create subscription models. But that said, one of the things that I think does make it a bit easier as a. Nimble and indie creators that you can pivot and see when these things make the most sense. So for me, offering the consulting was a way to be able to do a few things.One. If I look at that 20 hours of the week that I can now buy back, I can do better for myself. If I am very selective with the type of projects I’m taking on with the type of companies I’m taking that I’m working directly with and thinking about it, not just in a way where you are. Renting out your time for money, which I do think can be the reality for a lot of consulting projects, but what does that deeper layer?How can the insights or connections or work that I’m doing further help? Either my context, so trapped little, that it can be used in other, stories in other, Work that I’m doing or could somehow help what, what, what I’m doing in the future in some other type of way. So I always try to think about that when I’m partnering with a company or when I’m working directly with, with the client, whether it is on an advisory basis or it is on a specific project basis.So those are the things that. Have interested me and I think I will continue to do it. The thing that I’m most interested in in the future is what does that course, what does that digital product look like? Cause I think there’s a huge opportunity there with trappable and I think over time there’s a reality where I may pivot to doing more of that.Then I will have the than I will have the consulting. I think the thing that may make it a bit. Tricky though, is that because of the type of work I’m doing, there are a pretty selective group of clients that would truly benefit from being able to, partner with trappable or partner with me specifically to work on a consulting project.There’s so many of the insights from the weekly memos that I’m sending out. That’s like, Hey. Loved your thought on this. Can we talk sometime it would be great to get your thoughts and that’s how these relationships start, but there are only so many CEOs of these companies that can work in this particular type of way.So if you’re building a product and you have a very specific type of customer base, Consulting in a lot of ways does become quite attractive or having some other type of service where you know, that there are a very few number of stakeholders that are in this sweet spot, but these are deep corporations that have deep pockets in many ways, the best way to be able to partner and work with them.Would be to have some type of consulting agreement, whether that is purely for cash, whether involves equity or some other type of revenue share for whatever the deal may be. But that said, just given how many people in this space are thinking about their own personal growth, their own personal brands and how they can continue to grow.I think there’s a great opportunity for that digital product and the course in a company where travel is heading. And that excites me too.Nathan: [00:39:54] Yeah, that makes sense. Okay. I want to get into some specific numbers. and so feel free to answer or not answer any part of it. I’m going to ask three together so you can choose whether to answer all three of them or, you know, dive in on, on just one. I the first is I’d love to hear numbers of, you know, how big you were able to grow the capital audience too.So, you know, on just the free subscriber side, you mentioned the 6% free to paid conversion rate. And so just getting into the, what the MRR was when you shut it down. And then the third one is I’d love to just hear how your structure consulting deals are. These $10,000 consulting projects. Are these a hundred thousand dollars consulting projects?You know, how you go from there?Dan: [00:40:34] Yeah, so the newsletter itself right now, over 7,000 people subscribed to the email list. And when I had shut down the page, The newsletter itself, there were. To be honest, I forget the exact number, but I want to say maybe it was around like 220 230 people, or so that were paying either a $10 a month or a hundred dollars a year.So it was somewhere between like 22 to $25,000 in monthly recurring revenue. So, I mean, that was me doing the math of that to be like, okay, this is what I’m, you know, at least at this current stage, putting 20 hours a week into to be able to. You know, continue to, ultimately get that type of revenue. Of course it can grow, but it can’t grow until I have more time to be able to help grow that overall base.So that was a big, piece of the, decision there inNathan: [00:41:30] Yeah. So about, so 2200 to 2,500 a month in recurring revenue from the, from the newsletter. Yeah. So, I mean, that’s a solid baseline for, you know, like as an indie creator, having that coming in consistently. You know is really nice. That’s all of rent in some cities, you know, two thirds of renting in other cities, you know?Dan: [00:41:53] It doesn’t cut it in San Francisco, which is where I lived down. So, I mean, luckily I was able to, you know, I I’d saved up some money before I had started trap it’ll or not. Before I started charitable before I started working on it full time, because I said, you know, there’s probably going to be some, trial and error and I need to have a bit of comfort there.So it wasn’t all the money that I was living on. Thankfully. But I realized that, you know, there’s a timeline for everything I needed to make some changes and make some pivots there. So in terms of the type of projects that I have right now, it that I take on for consulting, it truly depends. I mean, I think for the most part, that main.Way that I’ve got about it. So the main standard is let’s do a three and a half month engagement where I am giving an overall assessment on what the best path of strategy should be. So this is me working much more on the strategy side, more than the implementation side of things. So if you think about how a trap metal article or how a trap capital newsletter is typically written, there is.My take my insights on what’s happening with a particular company. So if someone reads that, they’re like, Hey, we would love something like this, and even more in depth for what you think we should do. Moving forward that 3.5 months of work would include the. analysis, it would include the interviews, the research to understand what makes most sense for this company and then being able to provide overall recommendations, next steps, moving forward and so on.So it really depends on the company because in some cases, Is straight cash and other cases it’s, you know, revenue share or derivative rights, or if there is something, if there’s a partnership related to the future content that we’re creating in other aspects, I’ve become an advisor for companies and getting equity in exchange for that.So it’s definitely varied based on the deal. So I think for them, People that are listening to this. It’s probably best, helpful to think. Okay. Where are the places that you want to be able to serve? And for me, there was interest in being able to do. All of those things, whether it was working for the big fortune 500 companies or working for the startups and just knowing that the type of deal or the type of structure you have in place for a startup may not necessarily make sense for a big firms working for a big firm that three and a half months strategic.Advice works much for, you know, for some five figure amount of money makes much more sense than a startup where equity makes more sense for several reasons. One, they probably don’t have the cash to pay that. And secondly, Where they are from a company isn’t necessarily someone coming in with some big strategy deck or some analysis to be able to suggest things.They want someone that they can reach out to you. And hopefully if you become more of a trusted and supportive advisor, that’s always a running joke. Not every, you know, not every advisor is necessarily worthwhile. As they are, but if you become one of the worthwhile ones then great, great for you awfully that can work out well, if there’s an exit for the company in the future.So the flexibility has worked out well, and I think that’s what I’ll continue to do. Moving forward.Nathan: [00:45:09] yeah, that makes sense. And then you’re just able to tailor it to each, each business in each conversation. Let’s talk about the rise of newsletters, you know, we’ve seen, obviously you’ve been doing it for, for quite a while. you’ve run your newsletter on ConvertKit. There’s all kinds of things.Email’s been around for a long time, but over the last three years, but even the last, like 12 to 18 months, we’ve just seen newsletters take off like crazy. I was joking with Barrett, our COO at ConvertKit that like, it seems like half the people that follow us on Twitter, you don’t have a sub stack in their, in their Twitter bio and that sort of thing.And it’s just a level, whereas 12 months ago, 18 months ago, if you were like, Oh, you know, I’m a newsletter creator. People would be like, Where’s your startup, you know, whereas, you know, but now if you say that they’re like, yeah, me too, you know, and everybody is. And so I’d love to just hear your take both on, on platforms.And then maybe before that, get into the, you know, just the, the most recent wave of an excitement around newsletters.Dan: [00:46:09] right. I think I came in just before this wave truly kicked off because I had started, I at least I had the idea for travel and knowing that I wanted this to be delivered through email towards the end of 2017, because I started a trap battle, in spring of 2018. And then I started working on it full-time a year later, but yeah, so that, as you mentioned, yeah, 18 months, 12 months ago was when things really took off.So I think I kind of came in just before that, but I think that for me, the. The platforms tell a big story, because I do think that where people have chose to start their newsletters have said a lot about the brand and the identity of what the newsletter wave is, what it means and where things are necessarily going.I think what’s worked out well. I think Substack has been one of the main companies. Involved with the wave. I had trap it’ll on the sub stack for the first year that it, that that had existed. And funny enough, I found out about sub stack by typing into Google. Is there a platform out there where I can have my blog posts combined with my email list?Because. At the time I was looking for something that was very easy at the time, I knew that this was a pilot that I wanted to test out with Trapital. I wanted to see what this was like, and I wanted the tech to be as low and as easy as possible and ended up talking to the founders that work at sub stack, both great guys, Hamish and Chris, and was able to at least help me get ramped up and really think through how the delivery deliverability and audience for something like trappable.Could work. What I think later on happen though, is just given the ease of Substack and how it was built. It worked in a way that, because it was very easy and out-of-the-box to use it attracted a lot of the people that were like, Oh, well I have the content I have. You know, tens of thousands of Twitter followers.Let me find a way to monetize this content, because if I can follow the best case scenarios of a Ben Thompson or a, or some of the other people that are doing quite well, then I can. Monetize 10% of that audience by that I could hopefully come on and subscribe to my newsletter. So I think it performed and got caught on quite well with tech audiences that were seeing what was happening and just because of how popular tech, Twitter and VC Twitter is, it was able to help the spread of a lot of those things quite well.What I think differs though. And this is, these are conversations I’ve had with people conversations I’ve had with, Hammerson Chris at sub stack and also other creators is that what sub stack offers is great in that it’s a very quick out of the box tool that lets you as the creator focus primarily on the content you’re doing.What I think is a little different though, is that one, they are very much focused on having people start paid newsletters, and I think it can work out great. As I mentioned, it wasn’t the path I want it to go, but I think it can work out well from that perspective. So it’s very easy to turn on. And in many ways, it’s almost like how Amazon could work.If you’re a seller from a marketplace, it is very easy to sell your products. Right. However, if you want something, that’s a bit more bespoke, something that is a bit more customized for your audience, and you want to be able to be a bit more flexible almost in the way that Shopify or some of these other platforms are for sellers that want to have something you may want to move your newsletter off of that.And just have something where you can customize the website. You can offer products or services that aren’t directly tied to. Having a paid newsletter or freemium content. And more importantly, you can segment and see those audiences, see that audience in different areas. I knew that that valuable information and having that customization was going to be important for me.So it was worth the switching costs. I’ll call it in order to switch. And as you know, I’m now on convert kit, I’ve been on convert kit now for say a year and a half. And yeah, I mean, I think like anything, it took a bit of. Getting used to this would have been a mess, but it would have been a much tougher switch for me.If I had made the switch to cook, or if I had made the switch to ConvertKit earlier, if I’d started, I converted because I didn’t feel like I had it tested out. I was very new to this. I didn’t even know how to create a website already. The things that I would have needed to know how to do before this.But I do think that. You’re seeing a lot of people that will also kind of do what I did, where they’ll start on Substack get an initial following base there, and then they may move off of it. Or you see people that have stayed on sub stack and, you know, continue to do quite well for themselves. And I know there’s a bunch of other platforms like ghost is coming up and getting more popular MailChimp of course has been around for, decades plus now and doing.I’m still, you know, one of the top players in the space. So I think that the wave is probably going to continue for some time. I think, just to bring it all back. This is something we’ve seen outside of writing and this type of content as well with some of these paid podcast platforms that have come up or.Products like OnlyFans which is essentially like a paywall for Instagram. These types of things are coming up that are allowing creators to monetize their work in more individual ways in, I think that’s probably the overall way that interests me. So the optionality of this is great, but it’s important for creators to think, okay, where am I in the process?How do I think about this from that MVP perspective to be able to grow the product. And if I’m thinking about that, What makes the most sense And for me, my journey did work out pretty well with it so far.Nathan: [00:52:06] Yeah. I’d like to imagine that in your ConvertKit account, you have a segment for like, just music executives, you know, and it’s like just this group of people and you’re like, those, those are the people here’s the whole audience, you know, and you can break it down in so many different ways that you, right.You can’t do on, you know, a Ghost or a Substack or something that’s more built for broader publishing. But then at the same time from the difficulty or the setup side, right. You have to have WordPress, you know, and, and do your publishing, you know, and then the email through ConvertKit. So. There’s a lot of trade-offs, but I think it makes sense that, this trend that we’re seeing, if people starting on sub stack and then getting that level of traction and either seeing the payment cost or wanting an API or wanting flexibility or segmentation and reporting, and then say, okay, it’s time to graduate from sub stack to, kind of the next level.Dan: [00:52:59] right. Yeah. And I mean, I think that let’s say that if you are, if your goal is to, you have a large following and you want to monetize that following on the side from everything else that you’re doing. Something like sub stack could work out quite well. Obviously other platforms can do a lot of those same things too, but the quick plug and play aspects of it can work out quite well.But I knew for me, I wanted to do something a little different. I truly wanted to build a company that in many ways, stood for things beyond just monetizing the audience I had. I didn’t have an audience before I started trapping, so I didn’t come into it from that perspective. It’s something that I’m still okay.Building now. So being able to have that as a home base was a reminder of where I wanted to take things, but also a, a I guess, a stake in the road in terms of where I wanted to make sure that the company was heading and being willing to make certain trade offs when the time was right.Nathan: [00:53:54] Yep. That makes sense. Well, thanks for joining me today. It’s been really fun to dive into your newsletter in the world of hip hop. where should people go to subscribe?Dan: [00:54:03] so people want to learn more about this. Go to Trapital.co that’s the website. So that’s T R A P I T a l.co. Sign up and subscribe. I send a newsletter out every Monday, I call it the Weekly Memo and this is the weekly breakdown of the business of hip hop. So you want to get all of the latest insights, whether it is what’s happening with the latest artists, partnering with the company, a masters deal that’s happening, or just a wave of partnerships or deals that are happening that are even tangentially outside of hip hop, but are still related to the people that are operating in this space. It’s most likely going to get covered there so you can check it out.Nathan: [00:54:46] Sounds good. And also, I would just say everyone should follow you on Twitter. Just @RuncieDan on Twitter. yeah, you’re one of my favorite Twitter followers. SoDan: [00:54:53] Thank you. I appreciate that.

Dan Oshinsky was the Director of Newsletters at both Buzzfeed and The New Yorker. Today he runs his own email consultancy called Inbox Collective. Dan has seen newsletters from the early days, and has been instrumental in developing the newsletter strategy for some of the largest publications around. In this fantastic interview, Dan shares takeaways for large newsletters and indie creators alike. He shares how his newsletter led to the Buzzfeed job, and how, once there, he discovered the building blocks that make newsletters resonate with their audience (spoiler: cats ARE involved).Dan also warns us of the danger of obsessing over open rates (or any “silver bullet” metric), and how Job #1 for your newsletter is to earn its place in people’s inboxes.After talking about the importance of carefully defining your newsletter’s audience, Dan answers these burning questions: Can I really build a business around an email newsletter? Is email going away? Tune in for the answers, and so much more!Links & Resources Buzzfeed Newsletters The New Yorker Newsletters The Wall Street Journal Newsletters Dan Oshinsky’s Links Dan’s Website: danoshinsky.com LinkedIn: Dan Oshinsky Twitter: @danoshinsky Inbox Collective - Together, let’s make better newsletters. Sign up for Not a Newsletter Episode TranscriptDan: [00:00:00] It sounds kind of corny, but you kind of have to have a mission. When you start with the newsletter you have to have, this is the thing that I’m doing for this audience.This is why I think I can be useful and how I can be helpful. And if I do a good job, I build that loyalty. I build the audience in the long run. there’s going to be a return on that investment. Nathan: [00:00:24] In this episode, I talked to Dan Oshinsky, who was the director of newsletters at Buzzfeed, and then the same job at The New Yorker. And now he runs his own email consultancy called Inbox Collective, and Dan has seen newsletters from the early days. He’s seen multiple waves of newsletters become popular.And then of course he’s run, some of the largest publications around. So it’s a fantastic interview. He has a lot of takeaways that are good for, you know, large newsletters and indie creators alike. So I’m excited to dive in. All right, Dan, thanks for joining me today.Dan: [00:01:00] Thanks for having me.Nathan: [00:01:01] So let’s, let’s dive right in. You’ve got an interesting background in that we have all of these newsletter creators who. Come into it from, you know, any number of things, but, but they’re often indie creators where they’re brand new to the space, you know, or they’re growing up through one path and you’ve taken a different path of building newsletters at Buzzfeed than The New Yorker.And now you’ve got a bit more of the indie path as you’re doing the consulting and everything else, but I’d love to just take us back to when you first started to get into running newsletters at Buzzfeed and what, what started that path?Dan: [00:01:36] So it actually started a little before Buzzfeed. The first newsletter that I really launched was a newsletter called Tools for Reporters. It launched in 2012 and it was.I’ve been doing it a little while. It was Tools for Reporters is exactly what you think it was. It was a newsletter where we share tools that reporters could use.It’s actually still going. I went to the university of Missouri journalism school and some Mizzou J school grads have picked up that mantle and run with it. And it’s all it just hit earlier this year. Something like 200 additions of this thing has been going for a long, long time. despite my efforts over the years to, to accidentally kill it with, you know, having a job and having other things to do, it turns out when you get hired at Buzzfeed and you have a thousand things to do the like side newsletter, you’re working on becomes a little less of a priority, but it’s my entire newsletter story really starts with this thing Tools for Reporters.I was playing with lots of different types of tools. And it had stuff that I wanted to share figured a newsletter would be a good place to share it. set up a fairly basic, you know, at the time this was MailChimp. I went to MailChimp, set up a newsletter, pretty straightforward to get something off the ground.And in a couple of, you know, first couple of weeks, I got to a place where there were a few hundred subscribers. And for me, the game changer with email was I had, I don’t know how many Twitter followers or Facebook, you know, Followers or friends I had at the time, but I had more of those than I did newsletter subscribers.But if I put something out into the world on Facebook, or I sent out a tweet, nothing would happen, literally nothing would happen. I’d say here’s this exciting new thing I’m working on and nothing would happen. And then I would email a few hundred people and say Hey, here’s this thing I’ve been working on.And I would get Requests from people that, you know we want you to come in and sit down with us and have coffee, job interviews, the Buzzfeed job partially came at a result of at, or out of me working on Tools for Reporters. They. You know, when I started talking with them, I shared with them my newsletter and they’re like, this is really good.We like this. We can do more stuff like this. It was amazing to me how much more impact email had. the conversations I had out of email was really the exciting part because it wasn’t just me broadcasting, whatever news right out into the world but Putting stuff out there and then people writing back and saying I actually have some more stuff I want to talk to you about this, or I want to go deeper on that subject.Or how do you feel about this? I really got to build relationships with my readers and that always struck me as something that was really, really powerful, that set email apart. when I got to Buzzfeed, our, our thinking was twofold. One is we were going to have a chance to build an audience and really have ownership of that audience.of the relationship with them it wasn’t something where. Social media giant could just say one day, you know, We know you have X number of people who follow you on this channel, but, we’ve made some changes to the algorithm and you no longer have access to that audience. You know, we really have the ability to build relationships through email, which was exciting, but the other thing was the potential for conversations, the potential to ask people questions, to get their feedback and to really get to know our readers.That was really, really exciting and something we knew there was huge potential for Nathan: [00:04:57] Yeah, that’s big. And then, I mean, that’s the exact same experience that I had earlier with. Now of like, I actually expected social channels to outperform email, but people were like, you should have an email list. And I was like, okay, sure. You know, if you say so, I’ll listen to smart people and then you actually do it.And you’re like, Whoa, this is different, you know, 800 people on an email list is, you know, I would take that over like 5,000 people on a Twitter following. You’re definitely on Facebook. And so that blew me away from the beginning. SoDan: [00:05:27] There’s also the other thing too, for you, and I’m sure it was, he was definitely for me. And I imagine for you too, like, because it wasn’t something that you were hearing from a lot of other sources you weren’t, you know, like in the news world, when I got started at Buzzfeed, I started going around trying to find, I was like, Oh, I’ll, I’ll talk to the people who have my job at.The New York times, the Washington post, all these other places. Like I’ll talk to them like these are smart people. I’m sure they’ve already figured out email. Like I’ll learn from them, I’ll steal all of their good ideas and then I’ll bring it back to Buzzfeed. And then I found out those people didn’t exist.Like those jobs didn’t exist in other places. And. Email. My theory is always out. I’m curious what you think. Like my theory has always been just because everyone uses email all the time. People think they know a lot about it. They just assume like, Oh, I, I send emails all the time. Like we don’t need to have teams thinking about email.Like, what does email for in a newsroom 10 years ago is what does email for? Here’s an, arguous a reverse Chron RSS feed of our stories. We’ll just send it out to people or many times a day and they’ll click on whatever. And. That’s the end of the story. And so I started getting into it at Buzzfeed was like, all right, let’s talk to the smart people who are already doing this.And it’s like, Oh, well, there aren’t really that many orgs that even do this. And nobody really had my job. it’s exciting to see how much it’s changed, but it does, whether it’s going to be a Buzzfeed, the work you’ve done through convert kit, you discover that it just takes a certain amount of momentum of seeing like, Really smart people over and over and over again, telling you like this works, this works really well for people like, huh?I wonder if that email thing works.Nathan: [00:07:11] Right. Yeah. So what was your title at, at Buzzfeed?Dan: [00:07:15] When I started, I was newsletter editor, which was a title that, we made up because everyone at Buzzfeed who wasn’t me was associate editor pretty much aside from a writer, chief, like everyone was associated. And I was like, well, I’m an associate editor, I’m the newsletter editor. I’m sure that’s my title.And then at some point the team grew and then I hired a newsletter editor and they’re like, well, you can’t be this anymore because that title is taken. And Busby, wasn’t the kind of place where you become like the vice president of newsletters. So it’s like director of newsletters was the next title up.Then I, when I got hired at The New Yorker, the title just carried over. It’s like, we don’t really know what the title is. Director seems nice. Like, sure. That’s fine. I don’t, I don’t at no point throughout the process was the title a. Important thing for him to work at places like those. I remember telling my boss that new Yorker is like, you can call me whatever you want.I don’t care. You’re telling me I get to work at The New Yorker, but these smart people and help make a difference. Call me whatever does not matter to me.Nathan: [00:08:13] Yeah, that makes sense. So you’re bringing up a point about, you know, that, that title or really that job not existing. And I think that’s, that’s fascinating cause even, you know, people just weren’t using email. I mean, they were, but I think about when I was getting started in all of this in 2011, 2012, kind of around the same time, that you were diving in on it.People were using email, but like 5,000 subscribers was a, was a big email list. Like I remember following, you know, bloggers I followed would be like, Chris Guillebeau or a, Liam about to, from Zen habits. And I remember thinking back to that and like, I think they were like 8,000 email subscribers, 10,000, like, and those are the people that I thought of as being really big in the indie space.And now of course, like there’s plenty of people with millions of subscribers and. and so much from there, but, but it’s fascinating how even seven, eight years ago, you know, like you said, these job titles didn’t exist. It wasn’t a, Oh, here are all these best practices. Let me go copy them and learn from them and everything else.So what were some of the things that you learned in, you know, maybe that first time at Buzzfeed running newsletters of like, okay, this is what works, this is what doesn’t.Dan: [00:09:29] Well, I’ll tell you this. My first day when I showed up and our chief technology officer showed me to my desk and sat me down and in a very like, He meant it in a very colloquial way. It’s like, do you know what you’re supposed to be doing? And he mentioned it just like, you know, you’re supposed to be doing, I need to go back to my job.I have other things to do, but I took it into like, do you know what you’re supposed to be doing? I kind of hope when I showed up, they would have like the magic playbook, you know, Jonah Peretti would have like labeled out, like you do this and you do this and you do this. Then you have a job. everyone loves you.And it’s like, that’s like, no, I don’t know what I’m supposed to be doing because I was scary. But that first year we learned. So much about email. So the big things that first year were just figuring out what an email was supposed to look or sound like from Buzzfeed. Where are we allowed to have personality, your voice?Where did curation fit in at the time in 2012? You know, even a publication like the New York times, their daily newsletter was not a personal lot. Like today. Even Leonhard personalized, curated, they’re asking questions. We’re starting a conversation 2012. It was just, here’s a list of the stories that are most recent on our website.As of 6:00 AM. When this email goes out with no thought as to what the right subject line or which stories need to lead, there was no curation aspect. So all of that for us was like, what does curation look like for a newsletter like ours supposed to be, which was trying to do a combination of. News and humor and culture and lifestyle, like what even goes into a Buzzfeedy kind of email.So a lot of that first year was figuring out what is the voice sound like? How far can we push different sorts of ideas or products? I mean, I remember my first day I pitched three newsletters. The newsletter is for a daily newsletter, a long form newsletter, because we were doing a lot of kind of magazine style, long form reporting, and then a newsletter that I called this week in cats, and everyone laughed about it.But this weekend cats ended up being a really successful newsletter because among the lessons we learned at Buzzfeed were well, there were really four building blocks for us that made a great newsletter. 1 Newsletters were either about identity, who you are and what you care about. And. being a cat person it turns out is a pretty significant identity. Our cat people love cats. And then the dog people later on got mad at us because they thought we were biased towards the cat people. So we had this week in cats and then we had dog dang, which was also a great newsletter. identity was a big thing. 2 Service was a really big thing.The stuff people wanted more of, I want healthy recipes to cook for my family. I want ideas because I’m a parent, I’m trying to figure out. How would I entertain my kids? I’m trying to figure out how to do more of the stuff I want to do Buzzfeed Can you help me do that? 3 There was stuff that was more utility based, and these are newsletters around, your job around your community, around the news.I need to know what’s happening today. So I can be informed that a lot of local news organizations do this now, you know, I need to know what the weather’s going to be. I need to know what’s happening in my community or. if you’re, you know, someone like me, I still do a lot of my work in the journalism space.Art. I need to subscribe to newsletters around journalism and news. So I’m informed as to what else is happening out there. those utility newsletters do really well. 4 And then personalization. That was a really big thing for us. How can we add and utilize our unique personalities, the voices you could only get from Buzzfeed and bring them into a newsletter that people were really going to connect with and get excited to hear from.those four building blocks that really shaped a lot of the products, but that came through through testing through really a lot of different launches. Some that worked. Some that didn’t some that people thought were jokes like this week in cats, or, you know, I think we have the w the Internet’s first Royal baby newsletter when George was born at that kid is now like 37 years old or whatever.It was a million years ago that happened. but you know, we launched these different products, some of which people are like Buzzfeed, but then it turned out like, Oh, people really want this, like, We’re in the business of giving people stuff they want, that they care about. They’re passionate about. Yeah.Let’s launch the Royal baby newsletter, nothing wrong with that. No reason why we can’t have a news newsletter that caters to a serious news clientele, a politics newsletter, and yeah. A newsletter where where we’ll tell you when you know, the Royal baby is born. These can all exist under one roof.Nathan: [00:13:53] Yeah. So let’s take a newsletter like this. We can Katz, what does, you know, this is crazy idea that you throw out there and everyone’s like, Oh, ha ha. We’ve got, you know, it’s sort of like two truths and a lie where you’ve got two pitches that we’re suppose to take seriously. And then this third one that like, we’re supposed to ignore and laugh at.Like, you know, and you’re like, no, no, no, they’re all.Dan: [00:14:11] They’re all serious. We’re going to do all of them one day.Nathan: [00:14:14] But if we have to only do one, it’s the cat newsletter. So you choose, So in that, right. How do you measure success? What does, or what does success look like? is it just that you’re getting X number of subscribers? Is that like the, the growth rate, the open, what are you looking for? Particularly on the cat newsletter?Dan: [00:14:34] I got really lucky my first year at Buzzfeed in that I reported directly to Dao Nguyen who’s Now the publisher of Buzzfeed. One of the smartest people in media Dao knows everything about everything. And Dao was somebody who really impressed upon me there wasn’t just a single bullet metric. It wasn’t just like the open rate is the end-all and be-all If the open rates are good, we have a good newsletter. Or if we have a lot of subscribers, this is a good newsletter. We thought about growth. We thought about engagement opens, click to open rate. We thought a lot about, you know, Metrics like clicks per thousand if if the newsletter is going to grow.How many, you know, how much traffic does this newsletter drive for every thousand readers? so we could project, if this newsletter goes from 1000 readers to 10,000 to 100,000 how much traffic do we think this might drive? We thought about metrics like time on site. You know, we really utilize Google analytics.If someone’s clicking through on one of those long form stories to a Buzzfeed article, for instance, well, Those articles are going to take you 10, 15, 20 minutes to read. How long do they actually spend with these? Are they just clicking or do they spend time? there? And we would put together a couple different types of metrics to measure success over time.That’s changed for me now, I think a lot more about loyalty and habit. So how often do people, especially for something like a daily newsletter, how often do people turn to this newsletter day in and day out to read and turn to us for. Know, for, for their news habits. we look a lot more now it’s stuff like onboarding and automation.How are we utilizing that to drive engagement that we want, but it’s a variety of different metrics across, you know, engagement, habit, loyalty, growth. certainly for a lot of organizations or individuals too, you’re looking at revenue numbers is this newsletter driving the end result that I want in terms of revenue for my business, all of these together, give you kind of a full picture of success.What I find is the people who just pick oneif the only thing you care about is open rate. You’re going to do anything to get the open rate up. I mean, if the best example I can tell you is sign up for any super PAC’s emails and see the emails they send you. I got one the other day, it was a call to action to support, a a political cause the subject line was, and the, the, the, the sent-from name and the subject line was a flight confirmation.It was like, Flight confirmation number 6247 And it was like your flight’s been booked. I was like, what is this? And then I clicked and it turned out it was an ad telling me how I need to donate to some political cause it’s like, yeah. When the only thing you care about is opens and just getting people to like getting your message in front, you will do some weird stuff to get people to open your emails.You’ve You’ve got to have a bunch of different metrics in play.Nathan: [00:17:25] Yeah, that makes sense. And, well, I mean, first the thing is with any political donation, your email address then suddenly gets like passed on to like 50 organizations. And you’re like, it’s so frustrating, butDan: [00:17:38] It’s it’s the worst part about all there’s many worst parts about politics in 2020, but one of them is you like a candidate. You give them $10. Cause you think it’s, you know, I really believe in this person. And then you find out that until the end of time, you will be getting emails from other candidates asking you for money because that $10 donation means that you are suddenly Scrooge McDuck with an unlimited amount of money to give to all political candidates who come asking.Nathan: [00:18:05] Yes, but in that you see so many of these subject lines, especially cause I think, well, you touched on loyalty, right? And that being a metric that, if you had open rate, balanced by loyalty as a counterbalancing metric, then you’re not going to push subject lines in a way that, are click baity or spammy or anything like that because you know, that’s going to hurt her loyalty.But in this case where the email address was just purchased or passed on, you know, like your political party was just like, Hey, by the way, they had made a donation. So now his email address is fair game for any of you. then there’s no thought to loyalty because you don’t have any loyalty to the super pack or whoever else.And so then of course, they’re just pushing that. So that’s,Dan: [00:18:50] And at the, at the end of the day, at the end of the night, too, where people re anyone who’s working on an email needs to think about. If there’s one thing I’ve learned over the years with email it’s that email is not just a broadcast tool. It is a relationship tool. if you think about email as a relationship tool, as a conversation and of the inbox as this really personal space, this is their space.I tell a lot of my clients, I think of it as like a living room, like the client. So our reader is letting you in and saying, I’m going to let in my family and my friends and some of my colleagues and maybe you, and you’ve got to prove your worth to earn your place in this space. Like, all right. So what are you going to do?You’re going to start a conversation. You’re going to ask questions. You’re going to seek to learn about them. You’re going to try to make sure your newsletters feel personal and are relevant to them. You’re going to do a lot because at the end of the day, when you think about email as a relationship tool, Well relationships, are a long-term kind of play.Nobody thinks about how do I develop a relationship for today and tomorrow. And that’s the end of it. You think about how do I, you know, I’m making a new friend, I want to make a friend and I want to keep this friend for a long, long time. I want them to be someone in my life for a long time. You make a set of decisions that’s best to based on what’s best for the Both of you and email is the same way. The more you think about the relationship, the more you think about the conversations you want to have. the more you think long term, you know, it’s not just about getting an email address today and how can I sell something as quickly as possible? How can I get this person to know me, understand me how can I learn from them?How can I listen to them, establish trust, and then in the long run, once I’ve done that, we can do some pretty cool stuff together. When you think about the habit of loyalty in the relationship, it totally changes the way. You think about email and the types of things you would send to them, the things you want to do with them, what you even build in terms of your email product, all that stuff is great stuff that happens when you shift the mindset from broadcast broadcast, push, push, push to no, this is a conversation. Let’s start talking.Nathan: [00:20:54] What’s an example that comes to mind from your career. you know, or maybe even from a client that you’re working with now where that relationship really paid off, or, you know, you’re talking about, okay, I’m going to do this in a way that builds long-term loyalty. And that moment where you thought like, Whoa, this is a really loyal audience that we’ve built.Dan: [00:21:13] So I’ll give you the personal example with me. I, when I started this Google doc and. January of 2019, Not a Newsletter. The goal was just when I got started at Buzzfeed, I had always wanted there to be a place that I could go to learn from other smart people. And in the seven years between me starting and when I started me starting at Buzzfeed, and then we started Not a Newsletter.That place never really came up and nobody builds the, the go-to source for, you know, for email conversation, especially for people in news or nonprofits or individuals. There’s lots of great. You guys have one of these, but like there’s lots of great places you can go. For email conversation of high level and a lot of stuff around marketing, but I found that, especially in the new space, it was just lacking.Like, who am I supposed to go to learn from? So I thought that I might try to step in and, and offer some advice, and be a person that I could share perspectives and learnings from over the years. And then I had this Google doc and just launch it as a Google doc, so I could get out into the world as quickly as possible.And then I had an email alert tied to that. So you could come back for the next one. So people through that, through my onboarding series, through the emails I sent would reach back out. They they’d ask questions. Sure. Feedback. And what started to happen? I mean, this is one I’m still at The New Yorker.What started happening was. People started to ask me like this, we’re learning so much about email. We’re really excited. We have this budget to work on our email strategy. These next couple of years, we really, really try to figure out who we should be working with, who can like help us figure this stuff out.Who’s the person we talk to. And then I would write back like an idiot, like, Oh man, I really wish that person existed. It would be so great. If there was that person who could help you all figure out how to do this stuff, you know, like I have a job I’m working at The New Yorker. I got my hands full. I wish I knew who to refer you to.And then I got so many of these at some point, my wife just told me, it’s like, people keep asking you who the person is, your, the person. Oh yeah. It’s like, I see. Okay. Now I had to figure out, you know, people who work at it, the people who work at The New Yorker. A great thing about a place like The New Yorker is they always say, there’s that old adage.Like you want to work with people who are smarter than you you’ll you never want to be the smartest person in the room. There was never any doubt at The New Yorker that I was not the smartest. Like I was always the stupidest person in the room. I was constantly constantly thinking like, I cannot believe how much part of these people are the me, why they let me into this?Why did they let me into the building in the first place? but that means that people from The New Yorker also go on to like big ambitious jobs. They don’t usually go to. You know, David Remnick can be like, I’m leaving because I started a Google doc and people now want me to show them how to send better emails.Like that’s not a thing that they’ve ever had to deal with before. but from you really, that was it. That was like, Oh, having, and we’d done this. We’d ask questions of our readers, The New Yorker and gotten great feedback at Buzzfeed. We do these crowdsource posts and get great feedback and have really good conversations.But with Not a Newsletter, the email attached to that, that was the one who was like just by starting a conversation just by being willing to apply to every email that came in. You know, I had a list when I left The New Yorker at the list was about 1500 subscribers. And I knew when I left that I was going to be able to drive enough business from just 1500 subscribers because I was having these conversations because they were telling me.It made it real. In retrospect, it made it fairly easy to figure out what I needed to do to make my business successful because readers were writing and telling me, this is the thing I need help with. This is where I want to spend my money. And then when I would hear five, 10, 12 different organizations tell me we all have the same problem.It’s like, well, Good news. I’m setting up a business to solve your problems, and I’m going to make this one of the problems that I can just solve right away. It was great. I made it super easy now, you know, when I work with teams trying to figure out like, who is our audience? How should we market this?Like, well, have you talked to them? Have you surveyed them? Have you listened to them? Because they probably have a good, pretty good idea already of what it is that you do really well. And sure. Especially these big organizations, big brands. We’re going to go out and we’re going to spend a ton of money on some fancy marketing agency.That’s going to come up with a perfect slogan to explain what our product is like. Have you thought first about just serving your audience and hearing from them what it is that you do well, because you might be able to come to that perfect tagline, that explanation without having to spend, you know, five, six, seven figures on a marketing budget that doesn’t actually explain what it is you do well in the first place.Nathan: [00:26:06] Yeah. Oh, that makes so much sense. And I mean, I love that you brought up earning a living from a small list because I think people that do think, okay, I have to have 10,000 subscribers active 50,000, and we have tons of examples from ConvertKit. If someone earning a living from. 500 subscribers or 2000 subscribers are all kinds of things in that range.Usually they end up doing consulting, you know, we’re selling a higher priced product, you know, because the smaller number of people that you’re selling to then the higher price point, if say we’re solving for a $80,000 a year salary as our, as our base. you brought up a few things I have on my list here.In my questions, I didn’t even write it into a full questions or a full question. It just is Google docs. Question Mark. and it’s really not even Google docs. It’s a single Google doc. cause as you talked about Not a Newsletter is in fact not a newsletter. It is a Google doc, that you can go in and as you want to read the different issues in it, you just use the outline.On the side to go through. And one of my favorite things about it is the, so it’s a, it’s a read only a Google doc, right? You’re the only one who has right. Access to it. But as you’re in there reading that you see like other people popping in and leaving to read it because, you know, I don’t know what it is like anonymous wombat shows up to read.And so you can see like, wow, there’s eight other people. Reading this at this exact moment, then a couple people drop off and five more people jump on. but so I understand that you’ve launched it as a Google doc to move quickly and you wanted to get it out there and, you know, speed is an asset, but why is it still a Google doc today?Dan: [00:27:48] So it started as a Google doc, partially because. It was simple to launch. And also I had done other projects. I had this talk that I’d given a few months earlier where I had produced this as a Google slides. And it was actually, it was a list of ways to grow your, your email audience. And I’ve gotten shared around and people would email me say like, Hey, do you know, we’re just getting started or so-and-so newsrooms.How do I grow my email list? And then I would go, and I find that Google slides and share it with them. And there were always like four anonymous wombats who are lurking. It’s like, that’s weird. This talk that I gave to a hundred people that I never really publicized. Like, why are there always people hanging out in this Google slides, it just stuck with me.And so I launched it that way and now it may just be permanently stuck as a Google doc because it got known as the thing. That’s a Google doc. There’s a novelty to it. I always tell my news clients. Who will remark on the same thing going there were 17 people reading the Google doc at the same time on a random Tuesday, but.You realize that if you go to your Google analytics, there are literally thousands of people reading your website right now. Why are you impressed by 17 anonymous wombats? But I think there’s something about knowing that other, the, the, being able to look and know that other people are looking at this same thing at the same time, there’s something to it about knowing there’s a collective action there.You’re not alone, especially. This year when everyone’s isolated, the idea of, especially right after I sent it, when people like there’s like 175 people reading this thing right now, I’m like, yeah, the email list is a few thousand people at this point. Like people actually read this thing. I don’t can’t fully explain why, but people keep listening to me for some reason.And so, yeah, it might just be stuck as a Google doc. I will say. And I’m disappointed to say this, but I’m happy to break the small bit of news here on this podcast. I do think next year there will be an actual website that people can go to, to find some of the resources and links because. It’s to me. I started it to be as useful to as many people as possible.And as much as I would love to have it permanently, be like a series of Google docs and slides and this weird little world you have to like keep clicking and navigating to find. I also want to be more useful to a wider audience and it would be nice if. You know, I, an ironic thing about Google docs is they’re not actually SEO friendly, despite it all being a Google product, Google doesn’t make Google docs, SEO friendly.You can’t find it. So if you search for Not a Newsletter, You ended up getting redirected to posts or things, other things that people have written about it to get to it. It’s I would like the stuff that I’m doing that I think is getting really useful to a larger audience to reach a larger audience. So I do think there’s a world in which at least some of the, Not a Newsletter kind of universe exists on a real website that you can, you know, search for and find, it might happen.I think it’s probably stuck as a Google doc for the long-term though, just because. I don’t know if I switched it over. I think I would get angry emails from people saying that I like sold out to a WordPress or something. I’m not quite,Nathan: [00:30:56] Well, I like to think of Not a Newsletter as being like, sort of the speakeasy of newsletter content, where you have to know where to find it, you know, it’s like, it’s it’s and then you get there and you’re like, what did I even, what is this? but it goes to show that the important thing in a newsletter or any publishing business is the content.And really what you did is you cut through all of the noise of, should it be a newsletter? Should it be a blog? Oh, no, sorry, this isn’t a blog. This is a magazine. Or like any of these debates of decisions that people get into. And you said like, look, it’s content like valuable content delivered on a consistent cadence and a Google doc works right for that. so I love the simplicity of it.Dan: [00:31:41] I always, always, always urge newsletter. Creator is. If you’re thinking about launching a newsletter, the two things you have to think about first are and not just a newsletter, any product, a blog, a website, an event series, anything, any piece of content or storytelling that’s going out into the world who is the audience for it.And is it as clearly defined as it can be? Do we know really who we’re trying to reach? You don’t have to come up with. My, my reader is Susie in Des Moines. She’s 36 years old and she likes shopping at Hy-Vee, but like, you should know who your audience is in this case. My audience is people who work in email care about email, send email, and make their money off of email.Alright that’s about as specific as I can get. And then what am I going to do to serve them? What is the job of this newsletter? And with mine it’s I want people to be able to dive really deep into a topic that affects their lives. Help give them the opportunities for analysis, for insight, to identify trends and because it’s packaged in that way.It resonates with folks, but if you know any newsletter and you, your newsletter going to have 50 subscribers, 500, 500,000, know your audience and know what you’re trying to do to serve them so often. And I’m sure you get these conversations too, on like a daily basis. People reach out. I have this amazing idea for an email.It’s going to be great. Well, what is it like? Well, It’s a newsletter where I share the most common one that I get. It’s like, it’s a newsletter where I share all the things that I’m reading every single week, people are going to love it. Like, all right, well, okay. Newsletter, reassurance stuff that you’re reading this week.Who’s the audience like the audience is anyone who’s like smart and curious and interested. I’m like, yeah, I have really bad news. That audience isn’t there. You have no audience, like you’re building it on an audience of everyone, which means you’re not building for anyone. Like who are you really building for?Who are your people that you’re trying to reach now? Long-term you might reach more people than your existing audience. You might be able to build an awesome product that starts with a pretty narrow audience, and grows into something really big. Cool. That’s great. a Great outcome. But start narrow.Start with something really specific. It can always grow from there. People start thinking I’m going to build the next Skimm I’m going to build the next morning brew. I’m going to be the next James clear. I’m going to be the next Malcolm Gladwell. everyone is going to read this. no, you have to start small and specific.Have an audience in mind, know how you’re going to serve them. Then you can figure it out from there and grow it from there.Nathan: [00:34:19] Yeah, for sure. So. You know, we talked about newsletter starting back in 2011, 2012. Things have changed a lot, even just in the last 18 months or so to the last two years. What’s your take on like this hockey stick of growth that we’ve seen in newsletters?Dan: [00:34:38] it was in some ways kind of inevitable because even just in the time I’ve been doing this. This is at least the second cycle of email is cool. There was one back in 2013, 2014, when products like the Skimm and Horts were doing really well. And TinyLetter was really on the rise and doing well, everyone had a TinyLetter and it’s like, email is cool.And then there was the inevitable backlash, email sucks. Everyone hates email. I hate getting emails, yada yada, and then, you know, all of us working in email just kept doing our thing. And then when. This came back already for whatever reason. And cyclical comes back around. This is at least the second cycle of email as cool.And it will be followed inevitably with a backlash towards like emails to add. I hate email. it’s just, it’s going to how it’s going to go forever. someone’s going to invent the brand new thing. That’s the, the email killer. Then people forget You kind of have to have an email address to exist on the internet.And most people like using email, it’s simple. It’s there on your phone. You don’t have to be taught how to use it. And if you build good newsletters, like great, you’re reaching people in a space they use every day. Plus thanks to the rise of mobile phones. It’s easier than ever just to read something on your phone in those couple minutes, while you’re getting coffee or you’re on the subway or whatever it is anyway.What I think has really happened the last few years. that’s exciting is people have shifted from thinking about email is cool because email drives traffic. Email is the place, especially in the news and non-profit world and brand world was like, email is what drives all this attention, attention, attention.And now it’s like, Oh, Email’s The thing that actually drives all my results. My revenue comes from email. If I do a good job building the right products and the right relationships. Email’s going to sell a subscription to my publication. It’s going to drive a sale of my product. It’s going to lead to a donation to my organization.It’s going to be thing that drives a new member. now we’re seeing also people creators, and this is so exciting thinking, like if I build my audience, if I want to sell courses, I want to sell a membership, a subscription product, get people to come out to an event. Awesome. Like my email list is the thing that’s going to do that.I think email is just. No matter how much people say that email is like, it’s going to die. It’s not going to last, yada, yada like email is here to stay because it works really well. And it does. At a place like The New Yorker, Conde Nast, our parent company used to talk a lot about this idea of cross-functional teams.We’d be like, all right, we have people from marketing and sales and editorial and all these different parts of the work we’re going to work together. Email is the cross-functional tool. It’s the thing that does a little bit of everything. It builds relationships. It drives loyalty. It drives traffic. It drives sales.It keeps, keeps people coming back and reduces churn. Emailed us a little bit of everything. So I know people want email to go away. I think it’s just kind of here. You can accept it and get with it and try to build awesome things for email, or you can keep fighting it and keep fighting it. and At some point, people are going to give in and just say like Alright I guess this thing that works really well and everyone’s everyone’s having success with, I guess I’ll give it a try.Nathan: [00:37:51] Yeah. Oh, that makes sense. so as you’re looking at platforms and the recommendations on where people should. like how they should set up their list. Obviously there’s the converts and sub stacks and ghosts and WordPress and medium and everything else out there. Like what are you recommending to clients?And what are the factors that, that go into that as you’re trying to figure out what’s the best bit for each person’s newsletter?Dan: [00:38:14] So, wow. One is what that is a giant question. It is, it is one very individualized. I’m always very cautious about making big public proclamations. Like I never want to be in a position where. I, you know, I’m on a podcast or I write something in my Google doc and I’m like, this is the thing that everyone should use, because I remember seeing this back in the day where there’d be like studies done around email marketing and some organization would come out with some big report.And they’d say, like we did all these tasks, did all these tests and we found out that purple buttons convert best. And then you would open any email for the next six months. And they would all have purple buttons because one test happened and everyone just kind of thought on critically. It was like, well, I read on so-and-so marketing blog, that purple buttons.So like purple buttons for all. and so I’m always very cautious about being like, Oh, this is the thing you should use because. Everyone’s case is unique. And so a lot of what I do is kind of individualize conversations with folks. I’m trying to figure out better ways to do this. I released a up like a basic version of this ESP guide a couple of months ago, and there’s going to be additions to that.I’m going to do one in 20, 21 to around monetization from newsletters. And I’m trying to figure out ways to introduce kind of. Different sorts of recommendations for different sorts of users and try to personalize it as best I can. But even with that, I’m still expecting, I’ll probably even do a fair amount of like one to ones and encouraging people to reach out, to ask questions.Cause like, I think email can be so powerful and so useful. And I’m so incredibly nervous about saying like, everyone should do this and then forever. Or everyone’s like, well, I read this one thing. And even though it doesn’t necessarily apply to my case, I’m just going to take it at face value and use it.And then people like Dan told us to do this and it didn’t work out. what I will say is what’s very exciting. Is just one of these options, but there’s more options now to use email and use email effectively than ever before, which is amazing. From a creator perspectives is proliferation of tools, tools that can exist and be integrated with other sorts of sales platforms.So, you know, I’m an individual and I’m trying to sell courses or books or consulting. Or a paid subscription to my newsletter. I’m a news organization or nonprofit trying to drive reader, revenue, an e-commerce business, trying to drive sales, the number of tools that exist out there today, and options is really, really exciting and options.I mean, as far as I’m concerned and I always, as much as the work that I do with various ESPs and tech partners, like at the end of the day, All the writing that I do and work that I do is in service of my readers, who are writers, creators, newsrooms non-profits brands who are just trying to get the most out of email.And what I always tell them, it’s like the fact of the matter is there are more things to do with the stuff you want to do now. And there were a year ago and there were five years ago. It means you have choice. Choice is a really good thing for you. You get to pick like what. Back it up. And actually to your question, what I usually tell them, it’s like start with the stuff that you absolutely need.What’s the stuff that you absolutely absolutely absolutely need to be successful, make that list of the three or four or five things that you care most about. Okay. So at the top of your list is automation’s great. It doesn’t mean that the number one thing is automations. Don’t pick a tool that you aren’t crazy about, the automation kind of feature, and then start to narrow it down and ask to have this sort of automation.And we need this level of personalization, or we need a tool that has certain integrations, you know, we’re working off of WordPress. So we need something that has a native integration with WordPress. we’re working off of ghost and we want to figure out something there. We use Zapier for a lot of things and we need it to work, whatever it is, think about, you know, what features you need integrations you’re going to need certainly cost is obviously a factor, the data that you want out of it.And. With whatever tools you’re using, think about whether or not the product is being built by people who get your use case. You know, something that I, I really respect about what you guys have done at ConvertKit is you all have always really been this creator first kind of ESP. And there are lots of great email options out there and different ESPs are being built for really specific use cases.Awesome. Like. Try to find ESPs or partners who get what it is that you’re trying to do. It’s not just a matter of, you know, I listened to a podcast and I heard this one, ESP advertise. So like, I’m going with them to think more critically, like, do they get what you’re trying to do? And, you know, I. Even at a place like Buzzfeed in the back of the day at Buzzfeed, we use campaign monitor, send our newsletters and they were really good partner for us.back in the day, what I found was a lot of other newsrooms just automatically without asking us just picked them as the partner there. No, we had a really specific reason for picking it up. There were things we liked about their team, their setup, their customer service, their automations. That were really specific to what mean needed.You guys are picking them because you saw a press release that had my name on it. That I said that I really liked using their tool. Like, that’s fine. I do like their tool, but I really wish you guys had asked. You know, Dan, like, what do you think of this? We’re trying to do X, Y, and Z. Cause like they might be the right tool for you.They might not. and you really, because of the choice out there, like I just always encourage teams, like think critically, really make the list of stuff that you need, need, need. And then the stuff that would be really nice to have maybe, you know, Maybe it’s really, really important to you that your email tool will have like a countdown timer built into the drag and drop builder.I don’t know. Maybe that’s not. It’s like at the top of your list, which case sure. Like that narrows down your options quite a bit. Maybe the most important thing is automations. Maybe the most important thing is integrations. Whatever it is, like start with the list of stuff that you really need. And then that should help you narrow down.Like, you know what automations is top of the list. This tool doesn’t really do that. This tool doesn’t do that. Integration is really important. Well, that narrows it down a little bit more. You’re going to be able to find something that does a lot of what you want to do. The other thing too. And I mean this with all due respect to the convert kit, which I think is a wonderful platform, no email tool does 100% of the things you want to do.And, until you build your own email platform that does all the things you want. Like no email tool does a hundred percent of the stuff you want. If you get someone that does. 75% of the stuff you want, you get down on your knees and you think the product team that built that tool that does 75% of the things you want, you signed a contract and you move forward.Nothing does everything. There’s always gonna be stuff you wish it did. And that’s just kind of, part of it.Nathan: [00:45:40] Yeah, that makes sense. Well, and I think the biggest takeaway is from what you’re saying is that. The tool is ultimately not the thing that matters. What matters is great content in front of the right readers. And if you focus on those things, then, you know, like you said, get the tool that’s largely a good fit, not going to get in your way and otherwise focus on the content of the vendors because ultimately your newsletter could be a Google doc if you want it, you know,Dan: [00:46:05] It doesn’t really matter what the product looks like. It’s about the content. And are you serving a really specific audience? You do that. You can deliver this thing via carrier pigeon and it’ll do well, needs to be, have the content, know what you’re trying to do, do for your audience and do it well every single time.And you’re going to do good things in the long run. Whether it’s a podcast, it’s a blog shoot. You can prove to a print magazine, you can do a newsletter. You can do an events series, whatever it’s audience content well over and over and over again. And you’re going to have good results in the long run.Nathan: [00:46:43] Cool. I want to touch just for a second on monetization.Dan: [00:46:47] I reccomend it.Nathan: [00:46:49] Yeah, money. it’s it’s helpful. Yes. I’m pro monetization. Just want to get that out there.Dan: [00:46:56] You could slap it right on the, on the, the subject line of this, of this podcast, of this episode. Oshinsky, colon recommend making money. I’m not necessarily going to tell you how to do it, but I recommend trying its very leastNathan: [00:47:11] Yeah, exactly. So in that you’ve probably seen all kinds of different ways that people are making money. You know, paid newsletters of charging directly for the content, is seeing a big rise. People are doing, you know, courses, books, any of those things I’d love kind of your general overall take. And then what specific area that I want, you know, like your take instead of just some random newsletter creators take is kind of at this price point because you’re seeing the wall street journal, and all of these other publications doing right.They’ve done paid subscriptions for a long time. And often you have an individual newsletter creator charging more than like a major publication is doing, right. So let’s say that, you know, I’m signing up for, for this sub stack for $20 a month and I’m getting content that I’m really enjoying. And then I come across, you know, the New York times wall street journal, and I’m like $15 a month.That seems really expensive, you know? And you’re like, well, wait, what, you know, it’s, I’d love your take on, you know, these price points that individuals are charging versus newsrooms and. And, kind of thoughts on the whole paid newsletter thing in general.Dan: [00:48:18] So one is. I think it’s amazing that this new format existed. I mean, Ben Thompson, Mr. Tucker was really the first one of these to do it. And it’s the pioneer here, self stack and the work that you’ve done to push this forward. He’s amazing. And now we’re seeing a lot of folks interested in, can I build a business around a newsletter?the answer is yes. I think there’s a couple of things to keep in mind. One is not everyone needs to have a paid newsletter. Like I am one of these folks, Not a Newsletter, I suppose, could be a paid newsletter product that people would pay for access for I’ve enough readers that if I went paid, it would probably do pretty well.I don’t really have a lot of interest in doing that because I one. I Want to try to get my stuff out to as many people as possible impact for me is way more important than, you know, the total revenue I drive. Also, I make more than enough money with Inbox Collective. I don’t need the, so I’m happy with what it does and how it helps and, and, and.You know, everything that is fucked up, doesn’t have not just a lot of works. Dan, Runcie at Trapital is another great example, had a paid-newsletter product realized Oh, my impact is actually in, in telling these stories and doing consulting cool. Like there’s lots of different ways to make money off a newsletter that aren’t a paid newsletter.Consulting selling courses, getting people out to an event series, building a membership program. these are all ways you can drive revenue and that’s really, really exciting. So anyone thinking about launching a newsletter, thinking about making money from it? You don’t have to immediately go to paid newsletter.Like there are other options. It is one of several. I also think what’s really crucial and we’ll see, I think a ton of in 2021 are different types of paid newsletter products. So the wall street journal is a fantastic organization. Subscriber love their work. I think they do awesome stuff. We’re going to see a lot more in newsrooms in 2021, say, you know what?There’s actually a group of us who live in this city. We want to cover the city really, really well. We’re going to launch a newsletter. We’re going to launch and have a subscription product. That’s going to cost X number of dollars per year. People are going to pay for access to local news or coverage, in Charlotte, the Charlotte ledger.The team that I’m starting to do some work with, and they’re doing amazing work it’s business news for Charlotte, a very small team of reporters working on that. There’s going to be a lot of interesting opportunities there. It doesn’t just have to be, I’m a single person. I tried to build an audience and tell you about what I’m thinking there.There’s other opportunities out there there’s only so many, you know, Andrew Sullivan’s of the world, and. For a lot of folks actually thinking about a local news angle or thinking about working together with a handful of different writers to put together a real publication, this kind of bundle model publication model is really, really interesting.I am really bullish on the future of kind of driving record. I knew from newsletters, once you build an audience, there’s lots of opportunities to sell stuff. I just hope that people. There is a little bit of fear on my end that people are going to start these and think like I saw that. No jet lag, launched a newsletter and it’s doing amazing.And he’s just one guy reporting on this so I can do it too. And they think In three months I’m gonna be making $100,000 a year off my newsletter. I’m like, well, you don’t have an audience yet. You haven’t defined an audience yet. They don’t know ya It’s going to be, if you’re building a, you know, newsletter product you want to be your full-time business.It’s probably going to be a two-year process minimum to build and grow and drive the revenue you want. this is not a game you get into with like, short-term returns in mind. I often find myself saying direction is more important than speed, where you are going is more important than how fast you get there.If your goal is to figure out how to make a quick buck getting into the newsletter game is probably not for you. You had a question in there somewhere that INathan: [00:52:22] No, I, I, I think you’ve covered it. I, I, that’s a, that’s a great place to kind of start to wrap up. This is a long-term game and going all the way back to relationships and building that with your audience, building that loyalty with your audiences, it’s going to take time. And when you see things, I think a lot of people online see these gold rushes that happen over time.Right? You see someone making money, whether it’s, you know, maybe courses and then it’s Bitcoin, and then it’s amp like fulfillment by Amazon drop shipping or whatever else. And. So I think you’re going to have a lot of people right now and go, Whoa, newsletters are the way to make money right now, whether you’re doing a paid newsletter or anything else.And it’s like stop chasing gold rushes. Like maybe some of the other things, there was a gold rush. The gold rush of newsletters is going to take a long time for you to achieve. And I think most of the people who come in with the intention, or if they’re there for the primary reason to make money, rather than for a love of writing or the craft or whatever else.They’re going to get burned out and give up while before the money shows up.Dan: [00:53:30] it’s the, it’s exactly what I mentioned earlier with, my old boss Dow and that silver bullet. Like if the silver bullet metric is. All I care about is revenue. And I just need to make as much money as quickly as possible. Like this is not something that’s going to work out for you. If your only metric is traffic, like, all I care about is driving clicks.Like this is not going to work out. You have to have a couple things in mind. You really have to have. Honestly, like, it sounds kind of corny, but kind of have to have a mission. When you start with the newsletter you have to have, this is the thing that I’m doing for this audience. This is why I think I can be useful and how I can be helpful.And if I do a good job, I build that loyalty. I build the audience in the long run. I think there’s going to be a return on that investment and that time that I put in, but it’s not a short-term play like the, I drop shipping and Bitcoin. These are all great examples. Like email is like spend is like, I have a thousand dollars in the bank, where can I put it to make quick money?You’re like, well, I guess you could like bet it all on Bitcoin. And maybe you’ll get lucky. I don’t know a thing about Bitcoin, but I all other, other, other than that, Every time somebody tries to tell me about Bitcoin. I get confused. And like, I still don’t understand that at all. But if your goal is like, how do I make a quick buck?Like, I guess, like spend it on Bitcoin, but you could also just, you know, drive to Reno and put a thousand dollars down on black or whatever. And see if you double your money. Email is like, I don’t know, taking a thousand dollars and going out and buying some shares of Coca-Cola like, could it make, could it be successful for you in the long run?Yeah, that’s probably a pretty good bet. Give it 10, 15, 20 years.Right. It’s a longterm play. You gotta be in it to win it.Nathan: [00:55:10] Yeah. Yeah, totally. Well, Dan, thanks so much for joining me. Thanks for coming on the podcast. I’d love to, for you to just to end by sharing where people should follow your work and, and, you know, follow Not a Newsletter and Inbox Collective, and allDan: [00:55:23] Oh, yeah, thanks. So people can find me, Not a Newsletter is available at notanewsletter.com. and if you want to sign up for it, signup.notanewsletter.com. There is an email alert tied to the newsletter. It’s not a newsletter. It’s an alert. I know it’s a technicality. Please don’t be the 9000th person who’s emailed me about it.I know, I know. I know when I launched it, I gave it the name. I didn’t realize that one day I was going to have to explain over to him. There is an email alert technically, and it’s not a newsletter, the whole setup. So I signed up at notanewsletter.com. I do writing every single week, not on newsletter topics, just about stuff that I’m learning danoshinsky.com.And Inbox Collective, which is my consulting work, where I work with nonprofits and news organizations and brands to help them figure out how to get the most out of email that’s inboxcollective.com. Naturally, that’ll actually take you to a set of Google slides. again, once you, once you kind of form a brand as the person who does all their stuff on Google docs, this is what happens.You got to stay true to the brand. Yes, exactly. All right.Nathan: [00:56:26] Thanks so much.Dan: [00:56:27] Thanks so much for having me.

Anne-Laure Le Cunff is the founder of Ness Labs, which applies neuroscience research to productivity and creativity. In addition to writing articles and running a growing community, Anne-Laure also writes a newsletter subscribed to by over 25,000 “mindful makers”. In this conversation, we talk about building up a newsletter audience from zero. Anne-Laure tells us why newsletters grow differently from other platforms, like YouTube channels, and why you shouldn’t get discouraged when your subscriber numbers hit a plateau—often, if you just keep writing and sending great emails, the next wave of growth is right around the corner.We discuss the difference between Twitter and SEO as channels for gaining new subscribers, and the importance of saying “no” to all the things your business shouldn’t focus on right now.Anne-Laure also explains why she’s not pursuing brand awareness for her newsletter, and why she’s focused on maintaining the contract with her readers first and foremost.Links & Resources Chris Guillebeau Tropical MBA Podcast Product Hunt Hacker News Quick Chat with Anne-Laure Le Cunff of Ness Labs - The Indie Hackers Podcast SparkLoop & ConvertKit The Nathan Barry Show e017: David Perell – Mastering Twitter to Grow Your Newsletter and Make Money - Nathan Barry Anne-Laure’s Links Website: Ness Labs - Make the most of your mind Twitter: @anthilemoon Subscribe to Anne-Laure’s Newsletter Episode TranscriptAnne: [00:00:00] Saying no. And always asking yourself, why am I doing this? And is it the right thing to do? That’s the most important thing I thinkNathan: [00:00:13] In this episode of Art of Newsletters, I’m joined by Anne-Laure, talks about her journey from a product marketer at Google to running a very popular fast-growing newsletter. We talk about how she’s earning a living her fresh products and so much more. So let’s dive in. Anne-Laure, thanks for joining me today.Anne: [00:00:30] Thanks for having me, Nathan. Nathan: [00:00:31] So I would love to start with just why you started a newsletter. You’ve got a newsletter that’s quite popular now, you know, you’re, well-respected in, uh, all of our friend groups and all of that got a course that came out a ton of things. But going back to the beginning when you’re like, all right, I’m going to create a MailChimp account.When I get going, like, what was the impetus behind that? Anne: [00:00:54] Initially that was more of a personal challenge. I went back to university a couple of years ago to study neuroscience and I wanted to have a forcing mechanism to write about it. And I’m someone who actually feels quite uncomfortable with disappointing people.So publicly committing to sending a weekly newsletter about the topics I was studying at school was a way to force myself. To keep on doing it. I didn’t want people to be like, where’s the newsletter. I should say she would have it. Right. So that’s like, that’s where I was just, I just told people, Hey, every Thursday you can expect an email about when you were a science for me.Nathan: [00:01:35] Yeah. So were you able to hit the every Thursday? Did you stay on that? Anne: [00:01:40] Actually pretty much. So I only missed three newsletters. In one year, two of them were planned. The other one is when was when I lost my grandmother and that was on the day I was supposed to send a newsletter. And what’s crazy is that I almost went like, okay, I don’t want to think about it.I’m going to keep on writing. And then I was like, that’s like, no, that’s not healthy. Are you doing stuff? Writing? This is okay. And, um, the two other times, I actually announced it in the, the edition before, because I read it out about mental health and balance and mindful mindfulness. And this is part of it too, knowing when it’s better to just skip one newsletter so you can stick to it over the long run.Rather than burning out because you’re trying to be overly sustainable to a point where you’re hurting your own mental health. So I did skip a few ones, but I’m okay with it. I think what’s more important is to be able to stick with it over the long run. Nathan: [00:02:37] Yeah, I think that makes perfect sense. And I like your point about being intentional about it and saying.I’m not missing a newsletter, I’m taking a break. And I think that’s something that, um, Paul Jarvis has done really well where, you know, he’s had his newsletter going for many, many years, and then he’ll say like, okay, I’m taking December off or I’m taking the summer off, you know, something like that. And it’s just, uh, a good way to give yourself that break so that you can, you know, have the consistency and then, you know, readers know what to expect.We are consistent with newsletters, so that. Readers can check in and know, uh, you know, really consistently what to pay attention to. I remember one of the, the first people that I followed is Chris Guillebeau. Uh, he wrote the a hundred dollars startup and a bunch of other great books. And he would post every Monday and every Thursday at like 10:00 AM or 9:00 AM on the dot.And I, for whatever reason, I wasn’t on his email list. I don’t know why. But I would actually just be like, Oh, it’s Monday at 10. Like, and I would go and like, look for the poster. And if it was there on nursery day, it would go read it. And it’s just interesting how like, well, you can get trained to, you know, go to the place where the good content is.If the creator sticks to the schedule. Anne: [00:03:51] Absolutely. And you see that in lots of areas of content creation, right? Some of the most successful YouTubers are also following a pretty strict schedule where they tell people they’re very similar to what you just mentioned. Two videos a week one on Monday at this time one on Thursday at this time, same for newsletters, uh, same for blogs in general, any kind of.And they’re very worried. The person is trying to build an audience. You need to have some sort of contract with your audience where you tell them, Hey, you’re giving me your email address. You’re giving me access to the most intimate part of the internet for you. You’re giving me that that’s precious in exchange what I’m giving youthe contract is going to be—is that you’re going to receive. One or two newsletters a week from me on these days and I’m not going to break that contract. So I think it’s quite important to be consistent if you want to build that loyalty with your audience. Nathan: [00:04:50] Yeah. It reminds me of, um, one other podcasts that I listened to a lot, uh, called the tropical MBA.And I’m even realizing that in there, like sign-off for the show, they say, we’ll see you next Thursday morning at 8:00 AM Eastern standard time. And. Like it doesn’t even matter. Like I’m not looking for the podcast at that. Like, I’ll play it the next time I’m in the car driving somewhere. I’m on a run, but it, it has that like, you know, at this exact time you will get it.And it’s just interesting how prominently they put it into their show. Anne: [00:05:22] Absolutely. And that I agree with you that it doesn’t mean that people are going to wait that 8:00 AM on the dots to see it. But if every week when they checked and it was the day after, or it was one hour later, or the fact that they can trust that when they’re on the next run or the next drive and that this content is going to get there means that they’re going to keep on trusting you.And they’re going to keep on checking, but if they check in three times in the row, It’s not there, then they’re just going to find someone else’s content to consume instead. Nathan: [00:05:55] Yeah. That makes sense. What was the first milestone, um, for your newsletter that you felt like was substantial where you’re like, okay, this is an actual thing.This is working. Let’s keep going Anne: [00:06:07] to me. It was probably when I reached about 2000 subscribers was when I had this moment where I was like, that’s. An audience. They are, I don’t know, 2000 people in real life. So I felt like 2000 people, there are people in there I’ve never met in person who are not my close friends who are not my mom.So this is in the audience basically. So yeah, 2000 subscribers was when I started looking at it as something that could grow and that could become a more serious part of my life. Nathan: [00:06:41] What was like most impactful for getting those 2000 subscribers. And how long did it take? Anne: [00:06:47] I got there in a couple of months and as much as I’m a big advocate for consistency, the truth is that if you look at my growth curve—and it’s the same with lots of my friends who run really big newsletters—there were spikes where something happens and sometimes it’s something you control.in my case, for example, I launched my newsletter on product Hunt And I got a thousand subscribers just from that, which felt insane at the time because, you know, you just kind of double your newsletter in one day. And then there are others that I didn’t control. Like one of my articles going viral on Hacker News and insane.You get quite a few subscribers. So, um, it’s, uh, It’s a mix of things that I control like launches and stuff like this, and a mix of stuff. I didn’t control. The one thing though, that was really important was just to keep on posting every week. Right. And to make sure that I didn’t wait for people to find my content, I would write the content publish the newsletter.And then I would promote the newsletter on Twitter and different places, etc And while I couldn’t control which editions of the newsletter would go viral, by making sure that I would keep on doing this consistently, I was just increasing the chances one of them would be picked up by someone and shared with a bigger audience.Nathan: [00:08:10] Yeah. That makes sense. When, if someone was considering launching on product hunt, what are the, some of the things that. You know, you think would make that go well, like one thing that I can think of right away is you have very specific focus for your newsletter. It’s, it’s unique and engaging rather than just being like, Oh, these are Nathan’s musings on whatever, if I’m a random percent approximate, I don’t care about that.Um, so I’d love to hear your take on like what you think would work. Well there. Anne: [00:08:37] Few things. The first one is that it’s called product con. So I think this is what you were saying by, it needs to have a focus. And this is, uh, you know, I mean, you, you nailed it. This is exactly that it needs to feel like a product.So I would really work on the landing page and try and think about it as a product. What’s your value proposition? Uh, what are you offering here? What is the service, the product, uh, who is it for? Who’s the audience? What are they going to get out of it, et cetera, et cetera. What are the features, which in the case of the newsletter, you can describe what the frequency is going to be the length.Is it something that’s going to take two, three minutes every time to read so quick bites or are you offering more long form contents that people can read on their commutes? For instance, So features audience value proposition, et cetera, I’m really presenting it. Like a product has really been France.The second thing is that because of the way production works, you need your product to be quite popular in the first couple of hours when you’re posting it. So I really recommend waiting until you have about a Keystone, a thousand or 2000 subscribers. With a good chunk of them who are fans of your work, because then when you launch on product hunt and you can’t ask it’s against the rules to ask for a votes.So you don’t do that. If your audience is big enough and your content has been valuable enough to them, you don’t need to do that. People are going to come and comment on your post on product condensate. I’ve been reading this newsletter for two months. It has been very useful for me. This is what I learned.I really recommend signing up, et cetera. This is the most powerful thing that can happen when you’re not the one selling your newsletter anymore. It’s members of your audience who are doing it for you. They become ambassadors. So for that to happen, if you only have a hundred subscribers and half of them only are opening it.So wait until you have an audience and make it look like an actual product. Nathan: [00:10:41] Yeah, that makes sense. Cause I think so many people, um, say like, Oh, it’s just a newsletter and they treat it too casually and exactly how you position. It really matters because if you think about it, um, I’m trying to think of an example right now, but, uh, there are a lot of almost like software companies or a lot of real products that under the hood are just a newsletter and it’s just in the, in the packaging and positioning.And how you talk about it. That you’re delivering that value. And so that really matters. And going back to the contract idea that you mentioned earlier, you know, if you’re spelling out, this is what you’re going to receive on average is going to take five minutes to read, or, you know, like these are Epic long form essays, research driven.And if you’re spelling that out on the product page, then, uh, you know, people will understand what they’re signing up for. There’s a lot clearer expectations. So that makes a lot of sense. Anne: [00:11:34] And I just want to add that the other advantage of making it very clear is that you’re also making it easier for your audience to share with people who may also appreciate the newsletter.If it’s not clear. Even if they enjoy your newsletter, but they’re really struggling to articulate to a friend why they like it, right. It’s very hard for them to share and making the effort as a reader to share the newsletter with someone else is already a lot of work. So you want to make it as easy as possible for them.And you should tell them, this is what it is. Here are three bullet points that explain what the newsletter is about and why it’s so good, then they can just. Either copy and paste this or reformulated a little bit if they want to, but at least it’s clear. So you’re not on me making it easier for yourself to grow your audience bank directly acquiring it.You’re also making it easy for yourself to grow your audience by increasing word of mouth by making it cure what it is about. Nathan: [00:12:31] Yeah. So I think that, that, you know, one or two sentence description is really important, um, for a newsletter or any product. What’s, what’s the description that you have now for your newsletter.Like if I, if I asked what what’s your newsletter about? And then maybe how has that evolved over time? Or has it always been the same? Anne: [00:12:48] The current one is a neuroscience-based content for knowledge workers. Um, and the very earliest one, which didn’t work well was make the most of your mind. I’m in really good and catchy, but I think lots of people were like, okay, cool.What is this thing? So now it doesn’t sound as catchy, I think, but it actually works better because people are like, Oh, this is the content I’m getting, and this is the audience. Am I part of this audience or not? Do I think this content could be valuable or not. So, yeah, it’s, uh, it, it took me a while to switch because I really liked like the sound of the first one, but sometimes you have to be able to fall out of love with your own ideas and to pivot.So that’s what I did for the technique. Yeah. Nathan: [00:13:41] Yeah. Well, it’s this balance between clear versus clever and you started with clever and then later went to like, okay, let’s just be clear and direct and descriptive. And I think that makes sense. Uh, so the SIFO where the newsletter is that now you’ve, you’ve scaled it up quite a lot.What are some of the current numbers? Anne: [00:14:00] Uh, I’m at 24,000 subscribers now and yeah, I’m still at, around in between 45 and 55% open rates on the, the subject line that I’m using a lot. The, uh, the one that had the highest open rates in. And forever with was productivity porn. And the second one was idea sex.And now I’m thinking, is it the pattern here? Should I just talk about sex more? Is that where they say that sex sells? Right. So it really depends. Sometimes I have more boring subject science and so it goes a little bit more, sometimes higher and, um, yeah, that’s, uh, I don’t have other numbers in mind right now.Those are the two main ones. I look at how many new subscribers and what the open rate is like. Nathan: [00:14:51] Yeah, I think that’s a good number to pay attention to because if you become too fixed to get too fixated on one or the other than, you know, like. It’s actually not that difficult to grow a really large newsletter that no one pays any attention to.You know, and then, um, if you’re only focused on open rate, then you’ll probably end up with this really small group. And so I like to talk about engaged subscribers as the metric to optimize for, and that’s just, you know, open rate times total this size. And then if you can grow that over time, then you’re doing really well.Anne: [00:15:24] Yeah. One number I used to look at negatively before was the number of unsubscribers at the beginning, every time someone would unsubscribe, I would feel so hurt because I was like, are you breaking up with me Why are you doing this to me? And now I realized. Two things. Um, from a human standpoint, this is good that they’re breaking up with me.It means I’m not bringing them the value they expected they were going to have, so it’s good. We’re not wasting our time anymore. Staying in a relationship. No one wants to be in on the business side of things two Most email service providers charge based on your number of subscribers, right?Actually Actually I Should thank them for unsubscribing. So I’m not paying for someone who’s not going to read my emails. I’ve become actually quite positive about people unsubscribing where I’m like, this is great. Uh, we can both move on and I’m not going to have to pick up the bill. So that’s great. Nathan: [00:16:28] That’s right.Yeah. You don’t want to be paying for dinner for someone that’s no longer invested in the relationship. So, um, what are some of the things that are driving growth now? Um, on the, on the subscriber side, like what’s working to you bring in the most subscribers, Anne: [00:16:45] my, the main one is still Twitter. Uh, and. It may stay like this for a while, even though my fastest-growing acquisition channel is search engines I’m very excited about that actually, because Twitter works great for me in terms of acquiring new subscribers, but it is definitely correlated to how active I am on the platform. And I’ve never actually run the numbers, but intuitively speaking, looking at my analytics in Twitter and my analytics in my newsletter, there’s definitely some sort of correlation going on here where the more I tweet, the more people sign up to the newsletter, which is great because you can just tweet more and you get more subscribers, but it’s not sustainable.And there are times where actually you want to take a break from Twitter. my newsletter definitely suffers from that in terms of growth. So that’s quite interesting. Whereas for, with SEO and search engines I’m literally acquiring subscribers in my sleep I can go to bed. And then, you know, if an article I posted is actually doing a great job at answering the question people are wondering about, then I get a bunch of new subscribers.And I really like that. I like SEO because I can reach people that are Way outside of my personal circle with Twitter, it’s one or two, maybe three degrees removed from me, but there’s still a connection somewhere. Whereas with SEO, I can have access to people who probably don’t even have a Twitter account have never heard about any of the people in my circle.And who just need help with a specific question and then I help them. And if they start browsing the website and the previous editions of the newsletter they’re like great. I’m going to sign up because I want to hear more from this person, Nathan: [00:18:39] right? Oh, that’s so interesting. I love that. You’re making the correlation between.The active work versus the passive work or like which one is the treadmill? Um, which, you know, we’re actually big fans of treadmills. Like you can use them to get really fit. Um, but, and then, which is the system or the flight. Oh, that’s working for you. And so, yeah, cause for me, it’s the same thing with Twitter.Um, my Twitter audience and my newsletter really grow when I invest the time into it. And so I guess in that way, it’s good. Right. If you pour the time into it, you, you do really get returns from it. But then when you want to take a break, it’s like a cool, well, we’ll be here when you need it, but also you don’t get anything in the meantime, whereas with search, you know?Yeah. There’s these subscribers and this traffic that just keeps coming. Um, what are some of the things that you’ve done? Um, to optimize for search. Is that something that you’ve learned a lot about yourself or that you’ve contracted out to someone or is it that you just focus on great content and let everything else take care of itself?Anne: [00:19:38] Um, so I want to preface this by saying I’m not an SEO expert, everything I’ve learned on my own. I have, um, I’ve never worked with a contractor on this because I’ve been focusing. I used to work at Google before, and I knew some people who worked on the team, looking at the search engine. And even though.They never gave me any secrets because that’s way too precious to be shared like this. So they never gave me any of the particulars, but definitely there’s been a trend in the past few years where Google is focusing on the quality of the content, rather than at structural bits of the article that you’re publishing.So in the past you could probably improve your SEO a lot by just saying, okay, I need to have a meta description and these tags and these things, et cetera. But now the they’re using machine learning much more. You really need to think to put yourself in the shoes of someone who needs help with a particular question in kind of thing.Okay. And there are tools of to that help you look at that, like a RAF, et cetera, but. It’s more about putting yourself in the shoes of the person looking up something and like, how would they ask that question? How would they phrase it? And if I was the one looking up this question, what would I find helpful?And what’s interesting is that for some questions, actually, I want to read a quick one paragraph answer. I just want something really quick. Right. And for others, I need something that’s more in that. So it’s also changed the way I’ve been looking at it, where in the past, I always thought I needed to write.Really long articles to give value to people. And I feel really comfort. I have articles that are 300 words and they’re doing really great because they’re the only one answering that particular question. So it’s like long tail content. The way I’ve been going about it is just experimenting, reading about it, looking at my own data rather than looking at it.Kind of like blanket statements, types of tutorials telling you what to do. I’m just looking at my data and looking at what are the articles are performing best and trying to figure out what works well. And I’m using a couple of plugins on WordPress as well. They’re just flagging when I’m making. A massive mistake in an article where I’m trying to rank for a keyword and I’m linking on those keywords to another website.So I’m giving them all of my juice basically. So a couple of plugging and helping with this, but it’s mostly trial and error. Nathan: [00:22:07] Yeah. That makes sense. So SEO is a big factor. Um, what are some of the things that you’ve tried? Have you done any partnerships with the people who are running newsletters or cross posts or anything like that?Anne: [00:22:18] I’ve done these. And so I have definitely tried exchanging links and newsletters with other people. It hasn’t worked pretty well for me. I know that some people swear by that say that’s amazing. I kind of suspect that it may work for maybe smaller newsletters where it’s like, Hey, like everyone is so committed to you that they’re just going to go and sign up to whatever you say.Um, for, for bigger newsletters, like me, it’s really hard to find another newsletter that is hitting exactly what I’m offering to my audience. Right. And so I think one of the reasons why I didn’t work really well was because. The newsletter I linked, you were only half relevant to my audience and it was the same for them.They linked to me and was kind of like half event. So yeah, for me, it hasn’t worked when you, well, exchanging links like this. Nathan: [00:23:15] Yeah, that makes sense. I think that probably someone who has a really broad topic, like if you’re talking to startup growth, then maybe there’s 10 others on startup growth or writing or some of these things.Um, but yeah, you might be a lot better off. Like promoting a single article or something like that. You know, I I’ve definitely done like, cause I haven’t done it recently, but years ago to grow my newsletter, I would do things like write a guest post, um, for another newsletter or a blog. And that would, I guess it would usually drive more awareness and an engagement than it would necessarily newsletter subscribers or like as directly.And so it worked, but it wasn’t like, Oh, I did this thing and here’s another thousand newsletter subscribers instantly. Anne: [00:23:59] I think what you’re saying is very interesting because I, in the PA in a past life, I used to work in marketing and I think most people have heard of the concept of the funnel, right.Awareness and then conversion and then loyalty. And I think for a newsletter, especially when you’re at the early stages, Uh, you know, even if someone has 20,000 or 30,000 subscribers—most people I know who are in this range there’s still one person running the newsletter. They don’t have a team. It’s not like morning brew or whatever.The hustle, massive newsletters with millions of subscribers. I would say that for most people up to 50,000 people, you’re still writing the content yourself, et cetera, in. Maybe to me working on pure brand awareness at the beginning of the journey, may be a bit of a waste of time because—it’s notorious in marketing.That brand awareness is what costs the most time and money to put together and is also the hardest to measure in terms of success. And at the beginning of your journey, when you run a newsletter, It’s probably more important to focus on stuff you can measure and improve, and that has a direct impact on your numbers.And once you become wildly successful and you have hundreds of thousands of subscribers and you have extra money where you can start experimenting with more brand awareness stuff. Yes. It’s not that brand awareness is bad. It’s more about figuring out when you’re kind of stretched at the beginning. What are the places where you should invest your time and your energy that.are having a direct impact. Nathan: [00:25:44] Yeah. And what’s returning money. So it’s trying to talk about, you know, monetization and actually earning money from the newsletter. There’s a ton of different ways to do it. Uh, whether it’s, you know, sponsorships selling digital products, memberships, um, you know, paid newsletters are really popular.Now I’d love to hear what, what you’re doing now. And, and Y you know, out of all of the options you chose, what, what you’re doing. Anne: [00:26:08] So I first experimented with paid. EBooks that I was selling on the website and the newsletter was just a way to drive people to that. And I made it a little bit of money, but really not enough to pay the rent.And I very quickly felt like either. And I know you’ve been, you’ve had some very successful eBooks for yourself, so. Either I would create a new book and make it the product I would be focusing on and give it all of the love and the, the, the energy time, et cetera, that it would need to be a successful launch, but just running a newsletter and saying in the newsletter here’s my ebook was probably not a great way to go about it.So there’s probably better ways to do it by, but that didn’t work for me. What’s worked really well for me. And what I’m still doing is running a membership community. Next to the news letter and the content of the newsletter is free. I know that some people do paid newsletters, but for me, the newsletter has been such an amazing way to attract people to the website and to start nurturing them that I don’t want to close down this acquisition channel by putting it behind a people.So I want to keep the music for free. And this way, people who just need to read my content, they’re still getting value and this is great. But for the subset of people who want more, they don’t want to just read the content. They want to talk about it. They want to make suggestions. They want to ask questions.They want to ask, how can I apply what I read into my life and how are other people doing it? And how can I improve my own systems for all of these people who are. You know, probably like th at the time, it’s about 5% of the people who are subscribed to my free newsletter for those 5%, I’m offering more.And again, I’m just one person running everything. So I’m giving them extra value. And I’m saying, do you want to pay for that extra value? And the ones who want you, they can vary the part of the community. So that’s my model right now with the free newsletter and the paid community. Nathan: [00:28:16] Yeah. So I love what you’re saying about not wanting to cut off the acquisition channel.Cause that’s like, that’s the biggest challenge that I’ve had with paid newsletters or what content you put behind a paywall, because if you write something incredible, you’re like, Oh, this should go to my page like this, this is worth paying for, but then you’re like, But I need that. I need that piece of content and to go attract new subscribers and it should be free because this could actually pick up another 500 or another thousand subscribers, maybe just from the single article.And so you’re always in this tension between the best work that I put out, where should it go? And the conclusion that I came to is, well, I should do, I need to create more of my best work. And then that started to turn into like, okay, I’m actually not that prolific writer. I’m not, I don’t have the ability to create incredible work for two different, uh, two different channels.So how do you think about, or like, what do you deliver to people in the paid community? Uh, that isn’t for the newsletter. Anne: [00:29:22] First and in the community in itself, that’s why for at first I launched with just the community features. So they have access to an online forum where they can talk about the articles.They have access to week fees, zoom, meetups, altogether. When you pick a topic that’s been covered in the newsletter and we actually talk about it, um, We also have we invite experts where we do with them and they can tell us how we had one with Paul Jarvis, actually recent vivre. He came and talked about how he runs his newsletter.So the 80% of it is the community in and off itself. Recently I’ve started adding more exclusive content. And the way I do it is that I make them PDF reports. About something that I know the community is interested about. So one that we did a few months ago was cognitive biases and entrepreneurship. And another one I did last month was tools for thought and personal knowledge management PDFs are useless for SEO in any case.So there would be no point in just putting it on my website. So I optimize the page itself where people can build it for SEO. I tweet about it. So people know that this is available, but then only members of the community can download the full thing. And that’s been really helpful because first it’s been really good as an acquisition channel.Some people are like, I don’t have time for another community, but I’m going to read this report. So I’m just going to go with this. And the current members of the community they’re super happy because I never told them that they would be getting this. It’s like just a surprise saying, Hey, you’re a member.Thank you for being here. Here’s some extra content for you and it makes them, I think, but like they want to stay for longer because getting extra content. Yeah. Nathan: [00:31:24] That makes sense. And then you also probably don’t have the same, um, Burden on yourself of like, Oh shoot, what’s the, what’s the Epic PDF that I’m going to come out with this month because you sold them on the community and the connection and these other things that don’t take nearly as much of your time.And then you’re just delivering value over the top with a PDF, you know, a great report when you, you know, are inspired or have the energy. Anne: [00:31:50] Exactly. And that’s probably one of the most important things in general. We talked about consistency earlier. But not creating artificial consistency where you can stick with it is also still plants.And that’s why, what I love about having the paid community is that what I tell them is that here’s a community. We’re going to do stuff together, the exact stuff I didn’t commit to anything. So I’m someone that we can get bored pretty easily. I’m never bored with the community because I can wake up one Monday and say, Ooh.What if we do a series of coworking sessions this week, let’s do that. Like, I feel lazy and I’m procrastinating this week. You want to come and all jump on the zoom call and let’s work together. Uh, Amy would like pull drivers that was planned a week before. And that was again, if you go on our landing page for the membership, I’m not saying you’re going to get that.It just happened. So I think finding the right balance between saying I’m offering you a community and we’re just going to do cool stuff together and I’m going to be here and you can engage with me the exact details, like just common. Find out. Obviously the landing page is a bit more detailed than this, but have her comment on stuff.And for the newsletter is the same. I’m not necessarily committing to an exact format or to what exactly people are going to get. What I committed to. And that’s the contract is it’s every Thursday and these are the general topics I’m going to be talking about. And that’s what I can promise you. And I’m not, I’m never going to break that promise, but then if I feel a bit, yeah, like playing with the format or trying something new one week, I feel comfortable doing this because I’m not breaking the contract.Nathan: [00:33:40] Yeah, that makes sense. Um, can you share some of the numbers from the pay community? And I know you shared them on Twitter and you’re very public with that, but I’d love to give people that context. Anne: [00:33:50] I’m, uh, I met for 200 members, paid members, I think now. And, uh, In terms of, uh, Jimmy can’t remember, uh, I think that the monkey recurring revenue is around 6,000.Nathan: [00:34:09] Okay. Yeah. Cause you’re at $50 a year for the community membership. 50 Anne: [00:34:13] to $50 a year. Yeah. But some of it, I have two pricing. I have a $5 a month and $50 a year. So that’s why the numbers have been all over the place. And I’ve made so far. I launched back in March, made about $65,000 with the community. Nathan: [00:34:31] Oh, that’s awesome.So one thing that I wanted to touch on, cause you have a course that you, you launched the firm created from collector to creator, and I thought it was really interesting that that is. Uh, that’s not a separate thing it looks at and correct me if I’m wrong. It looks to be, you know, a new acquisition channel for the, for the community, because it’s all one payment it’s still the $50 a year.Uh, yeah. Talk about that. Anne: [00:34:57] Yeah. So two parts for this first, as I mentioned earlier, I really liked the idea of saying through the community join, and then you’re just going to get a lot of good stuff and you. You have to do it. You can’t tell people they’re going to do that. I’m good stuff. And there’s no good stuff.So that’s the first part, surprising people like this becomes a way of them wanting to stay because they’re like what what’s coming next. There’s always good stuff going on. The second part is yes. And the acquisition channels, for sure, because some people and I’ve had so many people tell me I’ve been on the verge on the fence of joining.For the past few months, but I wasn’t sure exactly if it was for me. And now this is this time bound thing where it’s like, Hey, it starts on this date. It finishes on this one. So if you want to join, you have to do it. Now. You’re going to miss this thing versus something that’s always there. And people just keep on pushing back from the time they actually.Do it, so that’s another thing. The third one is just logistical. It’s so much easier for me to manage everything as a community and say, Hey people, that’s the community. Everything is happening there. And when you have so many different channels to manage between Twitter, between the newsletter, uh, you know, I’m part of several telegram groups.Obviously I have 24,000 people who have my email address. So I also get a lot of emails that I need to reply to. And having every, everything in the circle community is a great way for me to not have more channels than I can handle. And I can just log in there, replay to everyone, make sure that I’m present and that I’m here to answer their questions.So, yeah, there’s also a massive logistical aspect to it. Nathan: [00:36:48] I think there’s a lot of really good points in there, but the simplicity for you to manage as a creator is so important. I’ve watched a lot of friends and convert customers and other people over say like the last seven or eight years. One is like get to a good amount of success and get to the point where they’re earning, you know, tens of thousands or hundreds of thousands of dollars from what they’ve created.And then they, you know, release higher price products and they layer on more products and they’re cross selling to this other thing. And not only does their email marketing get really confusing and complicated, especially as you’re like looking back like three years ago. Why did I. Why did I create that tag?I don’t actually even know what that was for, but then also your, just your schedule and like mental space gets so crowded. Cause you’re saying, okay, what is for this community? And what’s for that. And hold on, did I promise updates for this product? Or was that just thing should this, you know, and so you end up with this really complicated, overwhelming, uh, you know, thing to maintain.And so what you’re doing is basically saying. When I’m inspired to create something new, I can go, whether it be a PDF, a, uh, a zoom call with a friend on a particular topic, um, or, you know, a full new course, I can create that I’m going to promote it like a full lunch. So it gets all this attention out in the market, like, okay.And Laura just came out with this great course, you should pay attention to it. But then I get to fulfill it just through the same thing that I was always doing and have that simplicity, um, and then just drive more sales there. So I think it’s brilliant because you’re finding this balance between, you know, driving more revenue and keeping your life simple.Anne: [00:38:35] I love that you’re saying this because I’ve seen so many of my friends quit their corporate job because the state, they wanted more freedom and they ended up creating this new monster of a bus for themselves. Where the committed to so much that I genuinely think that their life today as an independent creator is actually more stressful than it was when they were an employee.And I really don’t think it has to be this way, and I’m not worried for them because I know that this is part of the learning process and they’re probably going to figure it out and, and, you know, change their processes and simplify them. But. I think most independent creators have had to go through this space.And myself included, obviously, like I didn’t just wake up and figure it out in one go. I’ve had weeks where I felt like this was too much work and this is why I’m being very mindful of my time time now. But there’s always this tension between being able to, to do whatever you want to do, because you’re technically your own boss.But also learning that it’s not because you technically can do whatever you want to do, that you should try to do all the things you need to make choices. And you need to remember that there are only a certain number of hours in the day. And one of the big reasons you probably left your corporate job was to have some freedom and to feel less stressed.So it’s important to keep that in mind. I think. Nathan: [00:40:07] Yeah, that’s good. And it was listen to, uh, your India hackers podcast episode. And you talked about burnout on there, um, and how, like that’s such an important thing to be mindful of and be aware of. Um, because yeah, like I am my own boss and it turns out I can be a terrible boss, you know, especially if I’m also the only employee.Um, are there any other things that you’ve done in either systems and processes or things you’ve committed to, or, or deliberately said no to. To maintain that level of freedom. Um, yeah, as you’ve gotten the audience?Anne: [00:40:42] One of the things that have helped me so much, and I felt so uncomfortable doing it at the beginning is that I added to my website into my newsletter form too.Paid for my time. If people want to talk to me, they can book there for one hour and we have a zoom call together. But as my audience has grown, I’ve had more and more people reaching out to pick my brains, which just gets my opinion on their product or on their newsletter. And it’s not that I don’t enjoy doing it that you love doing it.This is great. I love connecting with people. As I said, we only to have a certain number of hours in the day. So the number of days in the week and. At some point, I found myself in all of those calls with people from all around the world, which very quickly went from exciting to overwhelming. So now I have this form where people reach out to me.I’m like, yeah, I’m very happy to talk. Uh, you can sign up here. And if you want you, if you’re willing to pay for an hour of my time, I’d be more than happy to review whatever you want to review together. So that’s been a great way to protect my time. And that’s also been a source of revenue, which is great.And yeah, that’s like the only thing I can think about right now, I think that the main, the main rule that I’m trying to have is to try to say no more often. I’ve been asked for example, by so many people, I generally get two, three people asking me every week. When are you launching your podcast? And I know it’s ironic because we’re currently recording for us together, but I have no plans of launching a podcast right now.I don’t have time. I don’t have the energy. I don’t think this is what I would be doing best. I’m great at writing. I don’t think I’m that good at interviewing people kind of like talking and stuff like that. So. No, I’m not going to do it and it’s not big. I could technically do it, but I’m not going to do it.And as an independent creator or a solo founder, this is the most important thing saying no more often than you’re saying yes and always asking yourself, am I saying yes, because this is what everyone seems to be doing, or am I saying yes, because it’s the right thing for my own content business, the paid newsletters you talked about earlier, for example, if, for me it’s a great example.I feel like everyone and their mother and their dog are launching paid newsletters right now. I’m not saying they’re good or bad. They’re just a tool. And a communication channel they’re completely neutral. But as such you need to ask yourself, is it the right thing for me and for my business, is it really what I should be doing?Or am I doing it because it’s the latest trend and it was the same for podcasts last year. And it’s probably going to be the same for something else next year. So saying no, and always asking yourself, why am I doing this? And is it the right thing to do. That’s the most important thing Nathan: [00:43:38] Yeah, I, that makes so much sense. And having that awareness, um, really matters because. I mean, I always think of the Richard Branson quote, uh, opportunities are like buses. There’s always another one coming. And as a founder, you know, as a creator, you can look at that and you’re like, Oh, this would be amazing.Oh, that’s working. You know, I heard on a podcast that, um, you know, paid newsletters are incredibly good or that sort of thing. So let me jump on it and always. Uh, you know, hop on all of these buses and instead you can sit back and go, okay, that is great. I’m really happy that that’s working so well for that creator.That’s not me, or that will be me after I do this thing that I’ve already committed to and I’m going to protect my time. I’m going to protect my energy and, um, you know, follow through on this one thing. That’s something that I’ve given, um, a lot of advice to people. Who are starting multiple newsletters, which to me is, is a little bit crazy, but one newsletter is enough work, but I think you see how, how fun it is.And, you know, the growth is like, Oh, let me start another newsletter on this topic. And I always try to encourage people to bring it back and like pour all of that energy into this one thing, right? Like if you have 5,000 subscribers today, then if you, if you stick with it and pour energy into it, then you’ll get to the 25,000 subscribers.And. I think the other thing that people miss with newsletters is the ceiling is incredibly high. Like Tim Ferriss, James clear Ryan holiday, Gretchen Rubin, they’re all in the like, say, well, I guess I threw a couple of people in there who are the 300, 400,000 subscriber range, but most of that group is in the million subscriber or more range as individual creators.And so that’s the crazy thing with the newsletters. If you keep with it for a long time, Then like, like, I wouldn’t be surprised if you and I are talking, you know, I don’t know, two, three, four years from now. And you’re like, yeah, I have 200,000 subscribers on the newsletter and this is what results from it.If you stay really, really consistent, Anne: [00:45:43] it’s a great point is there’s no ceiling or the ceiling is very high as you say, but. The growth can be very inconsistent and compared to platforms like YouTube, where there’s an algorithm that is going to keep on bringing people through your content. So lots of people on YouTube, for example, they see exponential growth.If they manage to stick with it for, let’s say one year, a year and a half, and they do one or two videos a week for that time. And the content is good, obviously like you can never. I mean, I don’t know about YouTube because there’s backpack I’m doing really, really well, but you have good content, then you’re consistent.The algorithm is going to help you and help here and use our growth, your sorry, your YouTube channel grow. Whereas with a newsletter you don’t have such a mechanism that you need to get to quite high numbers before this starts having some sort of a feedback loop. I know you’re working with for example.So I’m going to change in the future, but up until now, there was no viral element to build into the newsletter because of this. I think lots of people get discouraged whenever there’s two weeks or three weeks or one month where the growth seems to be kind of, flat and that’s when they fall prey to the shiny-toys syndrome and they’re like let’s launch a second newsletter or let’s start a podcast or let’s do something else.Whereas what I have found in my very short amount of time of experience in my one year, and some months with my newsletter, Is that if I managed to keep going during those couple of weeks where it felt quite slow, then it would pick back up again because of an edition that did particularly well. lots of my friends, they have this staircase type of growth also with their newsletter where you can see spikes when something happens.But these spiked spikes happen only because they stick with it. So, yeah, I think you do need. More persistence and patience with the newsletter than you would with other types of platforms. Nathan: [00:47:50] Well, I think you bring up a really important point that there’s no built in distribution or, um, discovery platform for newsletters.It just doesn’t exist. Whereas on Instagram, Tech-Talk YouTube, um, even search right for blogs. That it’s there and, and you can grow an audience from it. And so that is a huge negative for newsletters. If that is not built in, on the flip side, the big positive is that all the distribution channels are available to you.And this is like a double-edged sword where on one hand, they’re all available to you. And so you can grow in all of these ways in, in a way that like, say if I’m going all in on YouTube, It’s I’m pretty much doing YouTube’s algorithm. Like I’m not also going to use Twitter to grow my YouTube channel to the same extent, um, because the, the value of each subscriber isn’t nearly as high on YouTube as, as it is sound newsletter.Um, so you have this, like with the newsletter, you can use any channel, but also which one do you focus on? And that’s where I was. I’m really encouraging people to like, It’s sort of a hub and spoke model. And so you have the hub, which is your newsletter. And then instead of saying like, here’s the 10 spokes that we could be doing, you actually just choose two and start with that.And it sounds like for you, you’ve chosen a search and Twitter, and those are the two. And then when you’re focused just on two, like it’s a lot easier. It’s not as overwhelming as trying to be like, let me pull subscribers from YouTube, Instagram, Twitter, search and everything else. Does that sound accurate?Anne: [00:49:29] Yeah, absolutely. I think you can have more channels in the future once. It’s exactly what you saying earlier about. It’s not that I’m never going through these things that I’m going to do them once. I nailed the first few channels, most big newsletters that are also doing YouTube, who are also doing all sorts of different platforms and channels.There’s a team. Behind the, the newsletter, like the face of the newsletter, you could get Tim Ferriss. If you look at James clear, she looked at all of these very successful people with their newsletters who are doing podcasts and lots of different things. Did you start doing all of these things in their first year, they only started doing it once they had the payment energy and people to help them do it.So I a hundred percent agree with you, I think at the beginning. And at least once it’s just you and you haven’t figured out your channels, two is great. It already takes a lot of work to get to channels rights. So get this to right. Once that’s the case, you’ll also know a lot more about your audience.And where else it makes sense to reach them. Whereas at the beginning, you may not even know, you may be investing a lot of times in five different channels and three of them are actually useless for you. So, yeah, I agree with you start with two channels. And once you get your way later in your journey, why not explore it more channels, but you’ll be much better equipped to do it.Nathan: [00:50:57] Yeah. One, going back to the point you made about product hunt early on. As you pursue this new channel or new growth opportunity, having the momentum and subscribers already makes a big difference. So like in the same way that you’re saying, you know, get 500 or a thousand or more subscribers before you go on product hunt, because they’ll help you get momentum in that distribution and discovery algorithm.Uh, it’s the same thing. Let’s say, if we’re like, okay, we’re now ready to do YouTube. Then you show up there and you bring your 25,000 friends with you and they like watch your videos. And then the YouTube algorithm says like, Oh, Wow. People are coming from outside, YouTube watching this, sticking around, subscribing, you know, getting more, watch time on it.You too let’s this must be a really good video. Let’s promote it. And the same thing is true of let’s say later, you know, you decided to write a book and release it on Amazon. Well then instead of like, hoping for readers there and like begging every reader to give you a view, it said, you just come in and say, Hey, all of you, will you please buy this and write a five star review.Thank you very much. And then magically you’re like, Oh, how how’d I get 500, five star reviews, you know, within a week. And it’s just because you like leveraged their stairsteps, you know, one platform into the next. Anne: [00:52:17] Exactly. Yeah. The network effects of your audience can be incredibly powerful if you’re using it wisely.I would say because it’s the same with everything you mentioned. Like if among them launching YouTube and then I’m fighting, I’m asking them to write reviews on Amazon and you always need to keep a balance in terms of value you’re delivering and value. You’re asking from your audience. Right. So just, you know, focusing on one or two things at the same time is also a really good way to not confuse them and to get the most out of the help.They’re very willing to give you a, you need to be clear as to what you’re trying to achieve and not ask too much either. Nathan: [00:52:57] Yeah, that makes sense. Um, one of the last things that I want to dive in on back in the monetization topic is. You’ve gone with, um, a very low price point of the $5 a month, $50 a year.Um, what are your thoughts on that versus say that the very opposite end of things, you know, like David Perell was, uh, the, the guest before and he’s got his, um, Write of Passage, uh, course, and he’s charging thousands of dollars for that. Um, what’s your thinking on choosing one end of the spectrum versus the other.Anne: [00:53:31] I would need to ask David exactly how he got to 2000, but the first I think most creators I know around me, they didn’t start with 2000 straightaway. Right? Most of them, they start at a way lower price point and most of the ones that are, or today around the 2000 price point, they’ve been running their course for a little while.They’ve had a few cohorts and they raised the price every time because there’s more and more value in the course. And it makes sense to raise your price when there’s more value. So. First, I think it’s a full secret to meet you say cure here’s 2015. So 15 for me is my very, very first course. Um, and in terms of just your general question about price point, um, two things first, I think, can you think about, are you delivering something that’s useful for work or that’s more personal because then your audience is going to be a little bit different.And I know that lots of people, if it’s something they can use for work, they can expense it. So the friction is a bit lower. They can tell their boss, Hey, I’m going to take this writing course, because obviously you want me to be a better writer and. Manager is going to say, okay, I’ll cover half of the price or I’ll just pay for it.Whereas for people in my community were like, Hey, I want to take care of my mental health. I want to feel more creative. These are very valuable things on the personal level, but they’re harder to sell to your bus. So they’re paying with your personal card. So that’s one thing to take in mind. The second one is what are you going to Denver?And if you charge 2000, you need to have. Incredible levels of support for the community and, you know, David and Tiago, they have a team of several people working with them. They have extra sessions, they have all of this incredible content. And so it makes change. It makes sense to charge 2000 because you’re almost positioning yourself against.The cost of a course in elite university that wouldn’t have the teaching assistant access to the labs and all of this material and the library, et cetera. So, yeah. Okay. 2000. That’s nothing compared to what it would be paying for an Elliot university, whereas in my case and what I’m telling people, very honestly, as I curious this community, and I’m going to give you live workshops together and it’s just me and it’s very new.And there are going to be technical hiccups. And the reason why charging solo for this first version is because I’ve really want your feedback, help me build this become co-creators of the course. So that’s why I’m charging at this price point. And I’ve also made it very clear with people that the second cohort is going to be more expensive.The third one is going to be more expensive and then may get to a price point that is similar to what they visit sharing is charging at some point. But I’m not there yet. So that’s how I’m thinking about pricing. Nathan: [00:56:27] Yeah, I think that’s so good. And that’s exactly what I wanted to, to focus on because when you start at the level that you did, and I love the way that you like, you even position it as a founding member, right.If someone comes in, they’re getting in early, they’re getting rewarded for that. They’re helping shape this with you. And you’re being very direct and upfront about where you are on your journey as a, as a course creator, you know, and everything else. And so you’re not saying like you’re not coming in and charging a ton of money for something where, you know, you might not be a hundred percent confident that that level of value is there because to your point earlier on freedom, like that completely messes up, um, You know, the whole freedom equation for you.Cause then you’d be constantly stressed about it. I would be constantly stressed about am I providing this level of value, but if I charge a low enough amount, then I’m like, Oh, I’m providing 10 X that value easily. And then as I add to it, I, you know, you also have the, uh, the urgency in that side of things.So like, okay. You know, founder membership is, you know, doubling to a hundred dollars a year now and get in before that happens. Or, you know, when you get to step it up with the value and, you know, not only are the early fans even more invested in and think you’re great, but then, you know, you get to have launches all the way.Anne: [00:57:50] Yeah, exactly. And I just, I really liked the idea of co-creating a community with the members versus just me broadcasting stuff. So, you know, I’ve already got lots of feedback on the first session of the course that I did yesterday, and I don’t think people would be so comfortable sharing this feedback if I didn’t insist so much on the fact that I really wanted it at the end of the first session, I told people.Did you enjoy this? If you did, the best thing you can do is take the time, like right back to me telling me what you liked, what you didn’t like, what could be better, et cetera. And when they launched the second cohort, I’m also hoping that because they participated in the first one and they co-created the second one with me, they’ll probably also feel more comfortable sharing it with other people saying, Hey, I took part in the first one and I know the second one is going to be even better because I helped making it better, Nathan: [00:58:52] right? Yeah. That’s so good. Well, I think that’s all the time that we have. Thanks for, thanks for sharing everything. Where should people go to sign up for the newsletter and join the community? Anne: [00:59:02] So for the newsletter, they can go to nesslabs.com/newsletter. And, uh, there’s going to be a link in there for the course.So that’s probably the easiest way to go about it. Nathan: [00:59:13] That sounds good. Well, it’s been really fun to watch you, you know, take off on Twitter and with your newsletter over the last a year or so. And I’m just excited to see where you take it. Anne: [00:59:23] Thank you so much. Thanks for having me. That was a fun conversation.

David Perell is known as “The Writing Guy” on Twitter, but did you know his email newsletter has over 40,000 subscribers? Not only that, but he sends THREE newsletters a week… every week! In this in-depth conversation, David shares exactly how he uses Twitter to grow his audience, how he maintains consistency with such a high rate of output, and how he’s built an amazingly profitable business by monetizing his newsletters with his breakthrough writing course.We discuss the top 3 ways for a writer to make money from their work and reputation. Should you: • Become a consultant?• Sell courses?• Start a company?David breaks down when each model makes sense, and whether people like Ben Thompson of Stratechery would be better off starting companies instead of selling paid newsletters. David explains why new writers should focus on quantity over quality—and when to flip that around. He also covers the small tweaks that turn your articles from flash-in-the-pan to evergreen. You’ll learn what to focus on when you’re just starting your newsletter, and the language to use on subscription forms to get people to sign up (hint: it’s not, “Sign up for my newsletter!”) Plus, how David sends 3 newsletters every week with less than 2 hours of work!Links & Resources ConvertKit - Email Marketing for Online Creators The ladders of wealth creation: a step-by-step roadmap to building wealth - Nathan Barry The Billion Dollar Blog - Nathan Barry Pat Flynn James Clear Paul Graham - Essays Tim Urban - Wait But Why Ali Abdaal - Part-Time YouTuber Academy Stratechery by Ben Thompson – On the business, strategy, and impact of technology. David Perell’s Links Website: perell.com Twitter: @david_perell YouTube: David Perell Subscribe to David’s Newsletter Check out David’s course, Write of Passage Episode TranscriptDavid: [00:00:00] This is one of the things I think a lot of people get wrong about getting more email subscribers is they’ll say something like sign up for my newsletter. No one cares. I say something like you will learn how to take ideas and then turn them into structured writing. Then you will learn how to distribute that structured writing.And then you will learn how to build a system to do this. It’s very specific and it’s very useful to the reader in so far as you have those three things, your conversion rates will go way up.Nathan: [00:00:34] Today on Art of Newsletters, I’m joined by David Perell, who has an incredible newsletter that he’s grown to over 40,000 subscribers. We dive into how he uses Twitter to grow his audience. He blows my mind with what he does on Twitter. we had a new, his research processes, how he sends out three newsletters a week really consistently.And then the biggest thing is how he monetizes list. he just makes an incredible amount of money off of the courses that he puts out there really, really high quality. And I think it’s a great model for anyone looking to build their audience and earn a living from their audience in particular. So with that, let’s dive in.All right, David, welcome to the show. David: [00:01:14] Thank you, Nathan. I’m a huge fan of both you and the company that you’ve built. I ConvertKits one of the most important platforms in my life. And thank you very much for all that you do. Nathan: [00:01:26] Oh, that’s great to hear. Well, I’m excited to share a lot of your story. We’ve known each other.What? Only a year or two. Maybe not, not that long, but I dunno, we both admire each other on Twitter and you know, I see you post stuff and I’m like, Oh, That’s an idea that I had, but phrased way better. So I’m excited to tell your story and to share a lot of the tips and tricks for building a billion newsletter.Why don’t we start just tell people about the Write of Passage, your newsletter, you know, kind of like give the high level view of the newsletter and your business and how it all works. David: [00:02:03] Yeah. So the way that I think about newsletters is that I guess I would segment it into two buckets. The first is the weekly newsletters that I send, which are Monday, Wednesday, and Friday, Monday is Monday musing, sort of a update of my life.And just the coolest things I’m learning. Wednesday is a email that comes out with every podcast that I publish. And that is quotes from the podcast links to YouTube videos. And then Friday. Is four or five links that I find every single week and that those are really the weekly ones. And then there’s a whole other thing or element to how I think about newsletters.And I run a writing course called Write of Passage. And whenever we open for enrollment, which is twice a year, we have 10 days to basically take emails and. People who have signed up and said, Hey, I’m really interested in this. And then other people have just been following along. We might be able to tip over the edge and we have two enrollment periods to get them in the course.And so for that, we use more advanced tactics like lead scoring, which we hadn’t had as native integration, which you have now in ConvertKit. And then also just sending out a very. Detailed and rigorous series of emails, mostly through the sequences tab. And then just through daily emails that we send to people who are interested in taking the course.So that’s how I really think of it. It’s the weekly emails. And then when things get really crazy leaning on ConvertKit, to make sure that we get our emails sent out to prospective students. Nathan: [00:03:46] Nice. So if we go and actually, if you wouldn’t mind sharing some numbers, what’s the, like how many subscribers do you have on the newsletter now?And, and if there’s any revenue numbers, you’re okay with sharing. David: [00:03:58] Yes. So we have 43,000 subscribers on the newsletter. And then for students, what we do is about 600 to 700 students a year, then the course. Is $3,000 as of now for the premium or for the standard edition and then about $5,000 for lifetime access.But we also give about six figures in scholarships every single year. And so you can do the math there and it’s also growing so fast that any revenue number I gave now would basically not be valid in six months. Nathan: [00:04:34] Yeah. That’s a good problem to have. I like that. That’s set up. So let’s go back and. You know, when you’re looking at first starting an email list or first starting a newsletter, what made you go down this road?What was the spark that said, like, this is a good way to spend my time. David: [00:04:51] Yeah. Everybody, who I spoke to and trusted, basically said something along the lines of at the end of the day, when it comes to selling products online, everything is in consequential except for the number of email subscribers that you have.And I took that to heart. I started off on Twitter. Been trying to grow my YouTube channel, but email was the place where I would always be able to meet people. People check their emails very religiously. And also email is really good for retargeting people. We’ve never spent a cent actually in any kind of paid marketing affiliate or any kind of retargeting, but eventually down the line that might be an opportunity.And having email makes that a lot easier. And then also. One of the things that was really important. I started off using sub stack and what sub stack didn’t give me was the ability to segment my audience. What happened when I first started selling, read a passage was say, I had 12,000 people on the list, but not all 12,000 of those people were actually interested in taking the course and say that you take 30% of my list.They’re the people who are really interested in being students and write a passage, but the other 70 just don’t care. And I want to still be able to email them and I want to build relationships with them in whatever way, shape or form. But for those 30%. I want to be able to send them a lot of emails and actually they want to receive a lot of emails.It’s not just me spamming or anything like that. They’re actually really curious in learning about the course. I got an email today. Hey, can you send me more email about what’s happening? And what I then saw was that I could segment my audience and basically say, these people are interested in this.Those people are interested in that, which then allowed me to create different avenues depending on interest and what people wanted to do for my audience. Nathan: [00:06:39] Yeah, that makes sense. So I’m a little torn on which way to go. We can talk platforms, which I want to get into. and maybe we’ll do that in a second, but in those early days, like, let’s say zero to a thousand subscribers, like, what was that process?How did you pull that off? And then what, what did you learn from that on what you’d recommend for someone else? Just starting out? David: [00:07:04] Let’s see. So I think that the beginning is hard because. There’s there. There’s this idea from the Bible called the Matthew principle where the basically it’s the rich get richer and the poor get poorer.And I think it’s very similar with. With writing email. you see the same thing in society now where there’s a lot of people who struggle to make it. And then there’s people who are in what I call the dividend class, where they’ve invested so much, that they basically just live off the dividends of their investments.And then all those investments continue to compound. This is a lot of how endowments work at universities. Right. there’s There’s actually something very similar in terms of. The way that building an online audience works. Paul Graham has this famous essay called do things that don’t scale. And when you start off, you actually want to do things that don’t scale in the same way that you would do with a startup and you are actually talking to people and you’re out at dinner with them—you’re saying, Hey, can you sign up for my list? I’ll literally sign you up right now. Or you’re Just posting, posting, posting all the time. And you have that email subscribe form at the bottom of every single page. You’re just trying to get the next subscriber, trying to get the next subscriber. Actually I think a lot of people, they start sending emails too early, but then they start capturing emails too late.And what I mean by that is when you only have like 500 subscribers or something. Maybe even 300, I don’t know if it’s actually worth it to spend two, three hours every single week, trying to send out your weekly email, but what you should do from the second you start writing is you should start capturing emails and whatever you can do to do that, you should absolutely do.One of the most common regrets I see on the internet is people say I started collecting emails way too late, and it ended up costing me millions of dollars in terms of potential revenue down the road. Nathan: [00:08:55] Yeah. We’ve heard that from Pat Flynn and tons of people over the years. I mean, that’s actually a conversation that I had with Tim Ferriss.Maybe, I don’t know, four or five years ago. he was capturing them who isn’t doing anything with them. And so they, they had the list went cold and, you know, he had to almost start from scratch. so in that time period, when you are capturing emails, but you know, you’re spot on that, right. You know, writing this Epic newsletter to 11 people was probably not the best use of your time.What. What do you do to actually, you know, scale that, to go from, say the, maybe you get the first 25 subscribers from friends and family. what was that next step for you? Was it writing Epic posts and getting those shared or more direct outreach or what. David: [00:09:40] Yeah. So it’s always a little hard to track, but one of the things that I would say is because you do bring up a good point about subscribers going cold.You don’t want that. Right? And so the way that I think of emails is much more like a postcard. People think of emails. It’s like these big themes, it’s like a big project. And honestly, people should spend way more time writing books and essays that stand the test of time. Like your book, Authority, is just as popular now as it was, I think in 2012, 2013, when it came out and.Then what you should do with your emails, sort of like what you do, right? It’s like really simple. It’s four or five sort of blocks and sections, and it doesn’t take you that much time. It’s really just like, Hey, thinking of you, you know, you should think of me. This is what I’m up to this week. And I read it honestly.I don’t read most of the newsletters that I get, what they are for is basically, Oh, Nathan Barry ConvertKit, top of mine today. Oh, James Clear top of mine today. And you basically get these pains, which then, because you’re top of mind in all these people’s minds, you’re basically creating this digital serendipity for yourself, which is the point of writing online.And what you do when it, what I did when it came to growing my list, was there a couple things I started off with lead magnets, which are. Which ended up actually not working out as well as I wanted them to basically people trading an email address for some kind of artifact. What worked really well was courses.And that’s because Twitter is the main distribution channel for me. So what I try to do is I try to build my Twitter audience and then basically convert some percentage of people. Follow me on Twitter, into my email list and. What I found is that I’ve had seven day courses on writing. I’ve had a five, I have a five day one on how to use Twitter.And I find that those convert really well. And they also are just so much more helpful than a lead magnet. Part of the reason why I wasn’t that excited about a lead magnet in addition to it not converting as well as I just wasn’t excited. It didn’t feel as useful to the reader as some kind of email course that I poured my heart and soul into.And. Now, what I’ve found is it hasn’t plateaued, but the growth is sort of linear. And what I’m seeing is the people who are sort of in the next grade of email subscribers, they tend to be pretty direct about asking for emails. Like you go on the front page of James clear site and it says right there, you can download a free chapter of my book for an email address.And then you’re on the page for probably 30 seconds. And then there’s a full-screen pop-up and. I’ve had to think a lot about, okay, what do I want, how far do I want to go in terms of asking for emails? But look, my site will do more than 2 million visitors this year, and I don’t think I’m converting enough of those people.And so the courses they’ve done well, but I want to continue to do a better job of capturing subscribers. Nathan: [00:12:31] Yeah. It’s an interesting balance, you know, and like James is also on ConvertKit and I know him well, and he’s got a specific subscriber number in mind that he’s. You know, targeting and close to hitting.And so I think that’s part of the reason for the aggressiveness, but it also plays a big deal into the next book advance. And, and the next thing of when you’re like, I have a hundred thousand subscribers, I have 500,000 subscribers and then the publishers are like, hi we’d like to talk, you know, and, and the checkbooks come up.And so, David: [00:13:01] yeah, yeah, yeah. I call this the paradox of book publishing publishers want you. To have a audience of millions, of people who visit your site every year. They want you to have an idea that is proven to resonate, and they want you to have a big email list. But the problem is when you have all three of those, you don’t really need a publisher.And so, and so the same things that publishers want is the same thing that makes it. So having a publisher just isn’t as important. Nathan: [00:13:28] Well, I think you brought up a point, if we go back a little bit to the content of what you send your list. cause one thing that I do is I went to only sending when I had like a big article to write like my ladder is a wealth creation post.And so what that meant is that I would email my list five times a year, maybe, which is terrible. Don’t do that. Like, unless you, I guess you’ve set that expectation then maybe, but I still wouldn’t recommend it. And then it felt like all the way on the other end was send out like a bulleted newsletter of like I’m going to be consistent no matter what.And so what I’ve tried to do is find the hybrid of that, where I’m showing up every week at the same time. And then when, you know, with these are the four things I’m interested in, you know, the books, creators, you know, resources, new convert, kit feature, any of that. And then when I have one of those big, long form posts, that is the entire newsletter.Yes. And if I was more on top of it, it would be like Epic essay once a month, you know? And then the other three Tuesdays of the month would be bullets or, I mean, ideally every other week or something like that. And because writing is not my primary focus that enables me to stay in contact with subscribers, stay top of mind without having to be like.You know, have the content machine ready to put out an ethic essay every month or sorry, every week, which I’m, you know, I’m my, my day is just not set up to produce on that level. David: [00:15:01] Yeah. And I think that also once you get to your stature, the actual thing that you should be producing changes. So when you first start out.I recommend to everyone, just go for quantity, publish all the time and get to a place where you’re publishing every single week I have a friend named Nick Maggiulli He was working at a litigation consulting firm in Boston in 2017, new year’s day, 2018. He looks in the mirror and he says, I am going to publish. Every single week and I’m never going to miss a week since that time—it was actually since that day, he has never missed a single Tuesday. He’s now the chief operating officer at one of America’s top investment advisor firms. that newsletter has. Truly changed his life in terms of every single week being able to produce something. But I’ve been talking to Nick—and I’ve been seeing it in myself because I just published 50 articles in 50 days.And so I felt what that was like, but I think that something begins to shift later on. Once you have that reach, once you have that distribution and once, you know, That you can write well, and you’ve learned the mechanics of what you need to do from a systems process, from a consumption process, from a production process, what you need to do to write.Well, I think that. You want to shift more into quality, then when you do publish something, everything becomes exceptional. And that’s what I saw on your ladders of wealth creation posts, which will be read for the next decade. that’s then what you optimize for. And also that’s what I’m trying to do more with long-form essays.I want to begin to be more like have a Paul Graham or a Tim Urban at Wait But why consistency? And I think that. For that, especially with the kind of work that you do, which is at the frontier, you’re talking with really high level people, which is what you get. But what you lose is you don’t have the time that creators like myself do.And so what I would advise to you, and I think that it’s actually what you’ve been doing is publish fewer things of exceptional quality. And when you publish them, make them a big deal. Nathan: [00:17:18] Yeah. That makes sense. And I think that there’s a lot that goes into that, of. Like a couple of these articles, I guess I did it with ladders of wealth creation and the billion-dollar blog and a few others.When you come out with them, you treat it like a product launch. Like if you take this approach of I’m going to write six incredible essays this year. Yup. Then you don’t get to just be like, I hit publish. I posted it to Twitter and I moved on and said, you have to say like, okay, what if this is the most important feature that ConvertKit came out this year?Or this is the level of. I maybe it’s not me trying to hit the New York times bestseller list with my new book, but it’s like, you know, I just wrote a self published book that I really care about and I’m getting it out there. Like what’s the version of putting it out there and really promoting it, you know, actually emailing 10, 20, 30 friends or texting people and saying, Hey, I wrote this, I love your thoughts on it.And making it like this real promotion and launch, rather than trying to write something Epic and then put it out there and be like, eh, I guess it just didn’t resonate. It’s like, So that it didn’t resonate. It’s that nobody actually read it because you treated it like, you know, Oh, I’m not a full-time writer.I’ll just put it out there. So that’s what I’ve been trying to do of when I put in the time on the creation side to then also put in the time on the promotion side, David: [00:18:37] I think that one of the things that’s been very surprising to me in writing a newsletter is. How much churn there is. And I don’t have particularly much churn, but there’s actually a psychological block there in that when you first start writing, you’re like, say that someone follows you on Twitter or someone follows you on Instagram.You just have no idea who that person is. When someone unsubscribes to your email list, it’s like their email is right there and you can look at it and you can interpret that as. I don’t like you nor do I care anymore. Your work is trash and there is a certain just consistency. You just push through that.I know that every Monday I’m going to send out my Monday musings too. 40,000 people. And like a hundred of them will unsubscribe. And actually in terms of the grand scheme of things, that’s a very good lack of an unsubscribed rating. But at the same time, it’s still a hundred people who have basically said, we don’t want to hear from you anymore.And I got to deal with that every Monday. And. At the same time, there is the balance of how you continue to grow sort of in advance of that and get more subscribers than you lose every week. And there’s something to that that just sort of has to become second nature. You know, even this morning, I started off in a course by my friend, Allie, aldol on how to build a YouTube channel and.It’s amazing how there’s like these ladders of difficulty. And at first you might struggle with perfectionism or you just don’t feel like, you know how to write. And this is sort of like what I would call like a level two struggle of realizing that a lot of people won’t resonate with your work and that’s okay.But email makes that very visible. Nathan: [00:20:31] Yeah. It’s I guess it’s the pro and the con of email. Right. You on one hand, you have that personal connection. People can reply or whatever else. And then, you know, the opposite is true. That if they’re like, Nope, I’m out of here, then that’s, that’s just as visible. And I remember, you know, in the early days of growing my list of looking at who wants subscribed and who opened and, you know, luckily once you get past a certain level, you don’t pay as much attention to those as, as much, it’s still totally a thing.one thing that. you mentioned earlier that I want to dig in on his email frequency, right? You’re sending three times a week. You’ve got different different styles of content that are going out at each time, but I’d love a little more of your take on, you know, how often should you send to your list and then how do you find that balance between, you know, only sending great content versus showing up consistently.And then as you talked about in the unsubscribes. The more you send, the more people are, you know, tend to unsubscribe. David: [00:21:36] Yeah. So lots of ideas here. So first of all, I think that the increased. Relationships that you build with the people who you send more often to far outweigh the number of people who unsubscribe.Yeah. Look, the number of people who aren’t. It actually just doesn’t matter that much. Like if you, if I was emailing someone four times a day, like it’d be different, but those people have just basically said, you’re not for me. And that’s fine. Like, it actually doesn’t bother me at this point. But what I really optimize for is the number of people who love my stuff and they want to hear more from me.And I think that when it comes to email, let’s just, I’ll give you the premise that what you can do is you can have either B consistency. Or B content, and then you could have a content, a consistency. I think that out of those sort of pieces that you could pick from, I would go for B content with A+ consistency in my entire life of publishing a newsletter.I have never once missed a Monday musings or a Friday Finds in hundreds of weeks. Not once. I did it today. it’s ritualistic for me now, in terms of the different kinds of content I call this burnt-ends content. And in the 1970s, there was a barbecue joint in Kansas city. I think it was Joe’s Bar-B-Que And what they would do is they would make the brisket and then there’d be the burnt ends at the end, they would throw them away. one day. There was a big line at Joe’s and the owners of the barbecue joint went out to the customers in line and started giving them the burnt ends And the customers are like, these are delicious.What did you make with them? And they were just like, Oh, this was just the residue. Of the brisket and we would have thrown it away. Otherwise we would have done anything with it. Now we’ll give it to you. Last year, I went to Joe’s and the burnt ends are the first thing to sell out and the most expensive thing per pound on the menu.How does that relate to writing newsletters? Every single thing that I write in terms of newsletters is the burnt ends of my intellectual life. On Mondays. I share the coolest things I learned this week. Those I already learned—I spend no extra time actually learning them. All I’m doing is compiling them into some kind of place.And then I send it out on Wednesday. My assistant actually writes the entire email because what I have to do is I have to fill out a notion page for every podcast that I do. And from that notion page, we take. That. And the transcript we produce for the site, we have a way of compiling it and it goes right there.I do a quick review and we send it off on Friday. I share my favorite links of the week, but I do no extra work to go find those links. I’m already reading them. All I do is type up a summary. And so I think that this is really key that I send three newsletters and spend less than two hours a week on those three newsletters, because it is all burnt-ends ideas.Nathan: [00:24:46] Yeah, that makes a lot of sense. And I think that’s probably the biggest thing that differentiates these creators, who are able to stick with it for years. like what you’ve done, like so many, so many other people have done from someone who’s like, I’m going to start a newsletter. sub stack is trending to convert it as trending.Let, let me spend something up. It’s super easy. I get five weeks in. I’ve got, you know, a hundred subscribers turns out it’s not for me. Nevermind. Let me shut it down. Is that. Like everyone’s looking at the work and they’re totally missing the system behind the scenes that creates it because if you’re coming every Monday, so the newsletter goes out at, I dunno, 10:00 AM.And every Monday at eight you’re like, shoot, what am I going to send today? Like, that’s a problem. But if at the same time, there’s the system to bring up, you know, writing and research, or even just throughout the week. You’ve been saving things too. Instapaper or pocket or, you know, bookmarking then you’ve got all of these resources and you’re just scrolling back and be like, Oh, what’s the most interesting thing that I want to share.And it turns a, you know, a painful, stressful problem into, you know, just a casual way to interact with readers. David: [00:25:57] Exactly. It’s all these systems and you just get to a place where it sort of just files in with your life and you just. Read something or hear something said perfect. That’s for my music.Perfect. That’s for Friday funds. And then you then create more assets. So one thing I do every single year—it gets me every year, three, 3,000 4,000 email subscribers I take all the coolest things. I. Posted in Monday Musings for the week, then I have this intuitive track based off the email responses that I get, which ones were the most interesting then I compile all the most interesting ones from every single week into a giant document that gets more than 100,000 views every year.Then at the top, I say, subscribe If I have a 4% subscribe rate. That’s 4,000 people. Then I just did the same things with my Friday Finds I was looking today on ConvertKit I have a 5.68. Conversion rate from people seeing the form into subscribing. then I just add to that every single week I share it repeatedly.And it then just becomes a bunch of these systems. And I think that this is one of the things that is crucial is to get less ephemerality out of the work that you’re doing. And you can just have very small tweaks and things to then take something that is only valuable today—next week, the week after—small tweak here, small tweak there, all of a sudden you have something that’s going to be relevant for a long time.So for example, you could say. Say that you’re talking about politics, and you could say how to write a speech, a really good presidential inauguration speech that will only be relevant for a small time. Then maybe it’ll be relevant every couple of years. Or you could say how to write a really good political speech that will be relevant 50 years from now, every single day during that time.it’s just small tweaks and framing that then allow you to get a lot more leverage out of the time that you spend, in investing. We talk about return on investment for every dollar you put in. How much then do you get out in creator mode? We should be talking about return on attention for every unit of attention you give.How much do you get out? Nathan: [00:28:06] I like that. if so we’ve talked a lot about the newsletter side of things. What do I want to go deeper for like those long form essays? And you talk about like these essays that stand the test of time. that’s harder to do. That’s another level of research. And so like pulling up these examples of Joe’s barbecue and things like that.Right. You, you know, I imagine those came from research. So I’d love to hear more about your process for, as you are writing this essay, you know, to be able to pull from your research and pull in the perfect example or another story, like, how do you actually go about. Creating that system. David: [00:28:43] Yeah. So let me just start by saying this is incredibly difficult and writing these long form essays.I do them because they’re at the frontier of what I can do and. I’ve had to build years of expertise, writing all these short ones to then be able to write the long ones. And because they’re at the frontier of what I can do, I know that there’s not a lot of competition there in terms of being able to write something exceptional, but also every single one I’ve written has changed me as a person.The Peter Thiel essay that I wrote sort of overtly was this essay about who is this famous investor? Who’s very controversial and how. Does he see the world differently? And what that was for me was having a lot of people. Talking to me about Christianity and me trying to figure out what my own relationship with Christianity was through an individual like Peter.And in that essay saying, no, he’s not just a great investor. Then the people who kind of understood him said, okay, he’s not thought that, Oh, he was really into this idea called mimetic theory. And I said, no, actually it all comes up from Christianity and. Then I wrote What the Hell Is Going On?, which came from a difficult conversation.I mean, at the Thanksgiving table where my entire family didn’t have the language to understand the world. And right now I’m writing an essay on how to save the liberal arts, because the trajectory of education is leading to education. That’s very vocational and not one that’s more contemplative and.Each one comes from this burning desire. Some question that I have that I need to answer that crucially either no one has answered. Or a question that everyone is asking everyone thinks they’ve answered and have the wrong answer too. And so provided that I can find that I then write these essays, which are these sort of multi-year projects.Sometimes. Usually I’ve done a lot of the research in advance and I’m probably 70, 80% of the way done with the research in advance. And then I begin to compile that into a central repository. He gets so many notes that I can’t help, but write the thing. And then I sort of take those Lego blocks tournament to sort of puzzle pieces and then try to piece this thing together.And each one takes me hundred, 200 hours, but they are the most popular things I’ve ever published. Nathan: [00:31:15] Mm. Yeah, I think it’s, it’s one of those things that. I find, I have to have those systems for logging examples in the stories in order to even be able to set, like, to make that possible. And but I think what you’re talking about is it has to first live as a question in your mind, like this thing that doesn’t quite make sense about the world, or you tried to explain to a friend and you totally botched it because you realized you don’t fully understand it yourself.And any of those kinds of things. Then once you have that logged, it’s sort of like, it’s easier to find examples and fill it in. David: [00:32:00] Yeah. I just want to sort of build on that. I think that that’s both the beauty and the struggle of this craft, which is these. Intuitions that no one can confirm or deny.And you just trust yourself and you just sort of stubbornly March and say, there’s something there. I know it. And then you talk to people and you actually can’t articulate what it is that you say. You can only listen to what you feel. And like my next long form essay after liberal arts is. How time created a culture of anxiety.And so I’m going to go back sort of through the history of the invention of the clock and look at how the clock is the fundamental technology of the industrial revolution. It wasn’t the steam engine. It wasn’t the train. It was the clock. And talk about how by splitting the world into these discrete units of seconds and minutes, and then taking us away from these naturalistic patterns of life, rising with the sun, going to sleep with the stars in the sky.Working during the summer. This is why we don’t have school during the summer because we needed kids to be on the farm for the harvest. Right. But now we are much more aware of the clock like you and I today we start at four 30, we end at five 30 and that’s fine, but it creates this sort of fiasco and stress of always needing to be at the next place and the world isn’t sort of naturally like that.And so. I obviously haven’t articulated this as much as I would like to, but I know that there’s something there and having that intuition, it there’s this certain self-trust that you need as a creator to say, okay, now I’m going to walk and follow that. Nathan: [00:33:44] Yeah, that makes a lot of sense. And so I guess if I were to give specific advice to someone listening, it would be.To pay attention and like be attuned to the things that stand out to you of whether that’s a question or something that you’re trying to explain and you can’t quite do, or that someone else says, and it just doesn’t sit right with you where you’re like, I’m not going to dive into the debate with you because I don’t understand what I think yet. Right. But I think you’re wrong. And I’m going to make that note in my journal and research it more. And those are the kinds of things that when you write about that, that can have such a big impact, like on the billion-dollar blog post that I did, that came from a conversation with someone where they were basically talking about how influencers couldn’t build real companies.And, you know, they would always be selling just selling attention. And I like had one or two examples of where that wasn’t true, but I didn’t yet have a framework for like, okay, what is true about how you transition from right. You know, an influencer who’s just like renting attention to someone who channels that into.You know, a hundred million dollar you know, liquor, empire, or a beauty brand or something else. And so when those questions that there, those are the best things that when you dive in you can create an like, turn it into a real essay. David: [00:35:12] Yeah. And I think that there was also something there for you, right?This is a question that say ConvertKit does I think 20, $25 million. Last time I heard an ARR and. Now for you. I mean, that’s subscription money, so it’s like really sticky and that’s really great. But then for you trying to sort of ladder up this platform and your own story of writing for designers and then the founding this company, right?Like there’s a, there’s a reason that you would write this essay. Not any stranger on the street. And I think that that’s important to that. We sort of feel called to write these posts in whatever way it is. And as you were talking about those conversations, there’s a word from the world of art that I think describes this really well.And it’s the word resonate. And what resonate implies. It’s not just, I connected with something. Like if you see a really beautiful piece of art and you resonate with it, it actually hits your body before it hits your mind. It’ll give you the chills. It’ll make you shake. It’ll have your heart. Racing faster.And if an idea repeatedly does that to you go write about it, go figure out what it is that is calling you. W what is your body telling you? And so I’m always sort of listening to the world for what resonates and trusting that sort of intuitive instinct for what I vibe with what I connect with. And then.As long as it sort of relates in some way to what I was talking earlier about some kind of question that everyone’s asking and either people have the wrong answer to, or don’t quite understand if I can find those too, then it ends up being a really fruitful path for. Where I can direct my attention.Nathan: [00:37:01] Yeah. That makes a lot of sense. Well, let’s turn our attention a little bit to list growth. You mentioned earlier that Twitter is the biggest platform for you, for distribution and new subscribers. Take me through your process there. What works for growing your audience on Twitter and what would you recommend?David: [00:37:18] Yeah, so I think that list growth is honestly the biggest place where I have opened questions. And I think that that’s important because. Marketing in general is the things that work don’t always work forever. Like at some level, like building an email list will be a smart strategy for the next 10 years.I know that, but the best way to grow an email list will often change. And one of the things that I’ve found that works really well, and this is what I do in terms of the actual, very tactical implementations of what I do online. It said, look for things that are working now. Where I have an advantage and that are working sort of disproportionately well and work well with how I like to create things.And what I like doing is creating Twitter threads They’re fun. They take me like 45 minutes, they crush. And if I have a good one, it’ll get more than 1,000,000 impressions. And so I can know that if I get 1,000,000 impressions and I link to. One of my courses, the conversion rate on that is going to be 1 or 2% and that’ll lead to a solid 1,000 2000 subscribers.And the challenge is with Twitter threads. It’s sort of like what we were talking about earlier in terms of systematizing and trying to sort of get things beyond you. This is about as labor intensive as it gets in terms of you have to earn every email subscriber, which makes it pretty intense at the same time, though.It. With my reach on Twitter. I know that if I write something good, there’s enough seeding the distribution that it’ll spread and it’ll flow. What I do is I will reply to myself in tweets with the link to the course and crucially, what I do is I, this is one of the things I think a lot of people get wrong about.Getting more email subscribers they’ll say something like sign up for my newsletter. I send one to two emails every month and you will get them straight in your inbox. Right. Very generic. And no one cares about, about your one to two emails. They want to know what are they going to learn and how are they going to improve by virtue of signing up.rather than saying, you’re going to get one or two emails. I say something like. You will learn how to take ideas and turn them into structured writing. Then you will learn how to distribute that structured writing, and then you will learn how to build a system to do this. Okay. Now that’s very concrete.It’s very specific and it’s very useful to the reader. Insofar as you have those three things, your conversion rates will go way up. Nathan: [00:40:07] I think that’s great. And I mean, the call to action that you specifically mentioned of the free course. Is so compelling because it’s, it’s not this generic, like sign up for, to get more content and you can do the Haven, you enjoyed this threat.I write about similar things here and like that’s far better than nothing. but yeah, if you have the specific call to action, that rolls from one thing right into another, it works really well like years ago. And that was probably 2013. I wrote this article for smashing magazine, which is a popular. design blog, and it was titled how to launch anything.And it, it was long. It was a really long article for me at the time. Cause I usually wrote like one to 2000 word articles and this one was like 4,500 words. And I was like, Whoa, look how long this is. And now obviously like so many people write way longer individual articles. but I tried to put everything that I had into that article.And then at the end, I said, Hey, I don’t want your education on product launches to end here. And so I put together this free course, so we’re going totally free content into free with an email, right. That, so this free course that over the next 30 days is going to teach you through case studies and everything else.Exactly how to launch a product. We’re going to take theory and put it into practice. And because it was, you know, a really valuable article, follow it up with more free value. The team at smashing magazine was totally fine with me ending. The article with that, that picked up 4,000 email subscribers at a time.Wow. That I had maybe five to 8,000 total on my list. So on percentage growth, it was, you know, crazy high and really what it was is delivering a ton of value upfront and then tailoring that into a perfect pitch for a lot more value. And I think that’s what people do with the best Twitter threads, right.Where it hooks you in. You’re intrigued by this story. It’s, it’s pulling you in, you learn a lot from it. Like, Oh, I had no idea about this business or this tactic or whatever else. And then, you know, at the end, it’s a very relevant call to action rather than like a generic sign up for my newsletter. It’s the logical, logical continuation of whatever I just taught you.But now behind an email opt in form Is there anything that you’ve learned on Twitter threads and that kind of thing. Like if someone’s getting started, they’re like, okay, David says Twitter threads work. Let me go write some, what are the, like the, a couple of high level things that you would say of like, do this? Not that. David: [00:42:42] Yeah. So what I would do is I will, I’ll talk about my style and what works really well. So what you want is Twitter works really well for things that require not so much context. So you want to, if there needs to be context, do you want to. Get to the chase very fast. And there’s a, I always think of Casino Royale.The movie starts with James Bond doing basically parkour running through Italy on top of these roofs. And it’s crazy for seeing it’s like eight minutes long and it’s Epic. And that’s how you want to think about a Twitter thread. Like you don’t need all this background story. You don’t need any of this, you know, hateful eight.We’re going to go through the carriage forever. And Tarantino movies take like 90 minutes to get into the action. And. I’m much more of the James Bond style when it comes to Twitter threads, just get to it. And that’s what you want to do. First tweet. You want to say, this is exactly what you’re going to get.Maybe something surprising. So I wrote a thread a couple of weeks ago about a golfer named Bryce into Shambo. Got I think 1.4 million impressions and. Fun fact about that. I almost didn’t publish it because I thought no one was going to read it, which gives you a really good sense of my ability to predict what’s going to do well.I’m totally serious. I was like, and then I press send and I was like, this is going to just be a vanity. Post cause I really liked golf. And so I was like, you know, it’s just for me, but it crushed. And so I said, Bryson, which I believe Bryson is the world’s most innovative athlete. And then I said, now I’m going to show you exactly what he’s doing.And I think that you want to. Just save people a lot of time and give them a lot of this rush of insight in a short amount of time. I think that that is even what good communication is that you, you have a lot of these little rushes of excitement within a sort of larger narrative that is being constructed.And I think that the classic example here is comedy. That what comedy does is it goes from beginning of the show to the end of the show with some general themes. Whatever it is, but within it, there’s all these little mini stories that actually begin to weave the mosaic that is being strung together.And. Any sort of two to three minute section has its own loud laugh. And I think that that’s what you want to do with the thread. So the theme is Bryce into Shambo, but each tweet has its own individual moment of insight, its own interesting idea. And what’s so cool about Twitter is every single idea gets its own replies.And so there then becomes this conversation of all the individual ideas within what you’re sharing and. That’s why I like Twitter threads. It really forces me to compress what I’m saying and to focus on the essence of interesting-ness. Nathan: [00:45:41] Yeah, that’s good. I think one of the first things that people miss about Twitter threads is they think of, Oh, this is a way that I can take that I can say something a lot longer.And so let me just take this thing and say it in five tweets instead of one. And what you’re touching on is no, no, no. Each one, if at all possible. Like there’s rare exceptions, but if at all possible it’s possible is its own complete thought. And it has its own takeaways. It has its own image, you know, whatever else so that like every tweet stand up, stand on its own.And what that means is right, that just plays into the idea of a headline, like, or a sentence. I forget it. What copywriter said it of, you know, basically every sentence his job is just to get you to read the next sentence. Yes. You know, and. If one of these tweets is just context or it’s just the extension of the previous tweet.That’s not going to get you to keep reading because your signal to noise ratio of a sudden got skewed in a way that, you know, Twitter is not made for you have to be high signal on every single suite, even when it’s a long thread. David: [00:46:49] Yeah. You know, and read a passage, one of the things cause the questionnaires, Oh, what do I write?Went to Porter fret about? And the first assignment in Write of Passage is write an answer to your most frequently asked question. And I think that this is something that people should be thinking about all the time. What is a story that you tell a lot, but really here? What is a question that people ask you all the time?Like, Nathan, I want to know from you. Out of all the interviews that you’ve done here, what are the things for people who have 50,000 email subscribers, which is where I’m about to get to, how should I get to 300,000? Say that that’s a very commonly asked question. I know that there would be an opportunity for you to write something really good on that.And what’s interesting about that is you have this experiential knowledge, which is what I always try to go for when I write, because the thing with experiential knowledge is. By definition, it takes experience to gather whereas knowledge that you read or that you can listen to in a podcast. It’s not the same.So for example, I had a student who was a financial advisor for FedEx pilots. That was his personal monopoly. That’s what he did. And he had experiential knowledge because guess what? He was a FedEx pilot for many years, which allowed him to. Which allows him to build trust with all of these pilots and.There’s things that he just knows that you couldn’t read online. And I think that when it comes to Twitter threats, when it comes to writing essays that we were talking about earlier, when it comes to writing articles, I think it’s always just worth asking what are, what is the access, what are the keys that you have that others don’t have?You have the keys to conversations with really interesting creators. You have the keys to see what it’s like to build a software company in the 21st century. You have the keys to have. Use the internet to build like tiny homes in, in, in Idaho and to think really deeply about what it means to build a remote first company.These are things that you have the experiential keys to and in so far as you’re able to sort of take what sort of abstract in these hazy intuitions and turn them into these really concrete ideas. You can then end up with ideas and storylines that other people don’t have, because these are byproducts of who you are and how you’re already living. Right? Nathan: [00:49:15] Yeah. Because a lot of sense, the last topic that I want to spend some time on is like monetization. Once you have the attention of an audience, and let’s say you’ve built it to maybe at least 5,000 subscribers and then obviously you’re at 40,000 and then we can go well beyond that too. There’s a lot of different ways to monetize paid newsletters are incredibly popular. Now courses, you know like video courses or cohort-based courses are, are very popular. I did eBooks, you know, back in the day. what’s your take on it? Why are, I guess, sponsored sponsored newsletters, sponsored content is quite common as well, but what’s your take? Why did you choose what you did?And then, you know, what do you recommend? David: [00:50:01] Hmm. So I think that there, I’m just going to talk about the really lucrative ways to monetize, even though there’s a lot which you’ve discussed. I think that the three really lucrative ways are Really high-end consulting where you work for. Corporations. And every single gig is at least $50,000.That’s where I would ballpark it. And you have multiple six-figure consulting gigs. So you know all about growth and you go work for Uber and you help Uber gain 2,000,000 new users and you are the person who drives that strategy. Number one. Number two is you run a course and that is basically productized consulting.So what you do is you have a consulting package that you do, and then you say, I say the same things to every single person. Now what I’m going to do is I am going to. Turn that into a product and I’m going to lower the price, but get way more scale. And so in so far as you can do that, now, if you’re teaching fast-growing startups, how to grow even faster, your market just isn’t that big.So consulting might be. The better strategy. Whereas if you’re teaching people to write, there’s so many people that want to learn to write that actually trying to productize and then get more scale is actually a better strategy. the best strategy of all is what you do, which is building a company that transcends who you are and what you are this founding influencer somebody who has unique knowledge and a personal monopoly in this area of interest.And then. You write about that and you use that writing to hire people, to attract investors if you want, and then to ultimately build a company that transcends who you are, where you’ve built the systems and you’ve built the structure in place, but ConvertKit is so much bigger than Nathan Barry, Nathan: [00:52:05] right? Yeah. And then, I mean, that’s where you get into brand and everything else. which can be a big factor in, in newsletters. I don’t know how much we want to get into it now. Right. But like Sam Parr with the hustle or the guys behind, you know, morning brew or any of those love those, they, they built something that is bigger than they are because they named it.Right. whereas like, I don’t know, the Nathan Barry show, right. It’s kind of hard to swap out Nathan Barry in that, but if you, but at ConvertKit right being its own brand, it’s very easy for me to swap in, you know, Maybe not a new CEO, I guess I could. but even right, there’s a team of 60 people building that company. Now I’d like to, I think, diving into a few of these other, other channels, right? If we’re trying to earn a living from a newsletter, right. Paid newsletters have become very, very popular lately. I’d love to hear your take on that. Like why do you have you know, why do you have a, a course rather than say a paid newsletter?David: [00:53:11] Yeah. So I think that this is kind of a hot take, but I actually think that paid newsletters we’re way over-indexed on paid newsletters. So the, the thing is, I’m not saying that paid newsletters are a bad business, and I’m not saying that the world is bad for paid newsletters. I’m a huge fan of paid newsletters.What I do think is. is An issue is there’s not a lot of people who are really serious about the opportunity costs of the upside of building a product versus the median range of building a paid newsletter. And I mostly don’t believe in subscription fatigue. And I think that the number of people willing to sign up for a paid newsletter, we’ve only scratched the surface there and for a certain kind of person who loves to write it is a brilliant job.It is great. I’m not saying Ben Thompson should stop writing Stratechery and should go start a company that is not what I’m saying at all. I’m just saying if you are at some margin where you’re 50–50 on paid newsletters versus company, I would definitely not. Definitely. I would lean towards starting the company because I think the upside is so big.And so I think that now relative to each other, paid newsletters is getting more hype than it should be relative to starting a company. Nathan: [00:54:36] Yeah. I think that makes a lot of sense. And when you think about. Like the median returns, which, I mean, we’re seeing a lot of people getting to $10,000 a month, $20,000 a month off of a paid newsletter, which is incredible to just be able to focus on that, to just write that’s so good, especially for that type of person.That’s good at showing up producing consistently on a deadline like journalists, you know, that is what you’re so good at. But then on the other hand, like I’m always encouraging people to look at the upside of the potential. Oh, there’s that to get a paid newsletter to a million or 2 million a year. Like that’s really, really tough.It’s also really tough to get a course to that level, but there’s a ton of examples of people doing that on the course side and a lot fewer on the newsletter side. David: [00:55:21] Right. And what’s going to happen is that we’re going to have Balaji Srinivasan has this idea of a founding influencer and that’s where things are going to go, where you’re going to be able to have your cake and eat it too, where you’re going to be able to create and make money as a creator.But you’re going to have the. upside of a company. And that is what we’re trying to figure out as an industry in terms of how to monetize your creativity. Nathan: [00:55:45] I love it. That’s a great place to wrap up. David, thanks for hanging out with us, taking the time to share all your insights. where should people go to follow your work David: [00:55:53] twitter @david_perell, last name perell.com.And the last name is spelled P E R E L L and obviously sign up for the newsletters. Nathan: [00:56:06] That’s perfect. All right. Thanks for taking the time. We’ll catch you later. David: [00:56:09] Thanks Nathan.

In this episode I sit down with Tim Soulo, the CMO at Ahrefs. He shares behind-the-scenes on how they've built a company to over $1M in revenue per team member.

 Trying to avoid center stage? You can get all the benefits of building an audience without putting yourself in the spotlight. In fact, you don’t even have to be the center of attention to connect with your peers and build relationships with your clients. Allowing your brand to take center stage can bring your business the returns you’re looking for and the email list you want.Ruben Gamez is here to tell us how you can stand back and let your work and your products speak for your brand. He is the creator and lead marketer for his website BidSketch.com, but you’d never know it. He and his team put together professional business proposal templates for freelancers, entrepreneurs, and anyone looking to find work and build a business online, but you won’t see him speaking at conferences or selling on tv spots. That’s because he prefers for his business – his tool – to speak for itself. Find out how he built his audience through his own specially designed content marketing campaign, and how he designed a product that practically sells itself.Topics Discussed Creating and using drip campaigns to your advantage Using your email list to your advantage for pre-sales and promotions How to build an efficient contract team Developing your skills and uncovering your skillset How you can do content marketing for your blog Find out why we don’t always trust Google ResourcesCheck out ConvertKit.com/blog for conversion tips and tricksGet a proposal template from Ruben at bidsketch.comFollow along with all of the great things Ruben is putting together @bidsketch and follow him personally @earthlingworks on Twitter.

 If you’ve ever felt like your blog posts are a shot in the dark, this episode of the Nathan Barry Show is for you. Working to build an audience never has immediate results, but don’t be discouraged by your lack of response! My guest today will tell you how to produce valuable content over time in order to generate the right kind of response you need to see your business succeed. As a professional freelancer, Brennan Dunn knows the ins and outs of creating an audience and a viable client list. His style of content creation and content marketing has been a huge influence on my own business style. He first started by writing a business blog about the conversations he was having with his own customers as an ingenious way to get new customers and build his email list. This pro-active approach to business, including writing and publishing an e-book, creating his own content, and using paid acquisition through Facebook, is what he’s talking about with us today. You can apply his insight to your own marketing plans to develop something that works for you.Brennan has probably had a bigger on impact on the way I do online business more than anyone else.Brennan has built an audience by communicating with them regularly: regular emails promoting new/regular blogs, direct conversations, free advice, promotionals – Brennan pre-sold his e-book to his Planscope emailing list.  He also offers a range of products to better serve your clients that results in more income for you.Topics We Discuss What the very early days of audience building look like How consistency converts your early subscribers into customers Paid acquisition and why you should be using it already How to use Facebook’s Target to promote and communicate with clients What to do for a product or book launch Pros and cons of payment plans for customers (spoiler alert: it’s worth it!) ContactSubscribe to Brennan’s list at www.freepricingcourse.comLearn more about Brennan and his insights on freelancing doubleyourfreelancing.comIf you have a minute, I would really appreciate if you would write a review on iTunes about today’s episode. Whether it’s good or bad, let us know what you think by posting a review in iTunes.This season of The Nathan Barry show is sponsored by Kajabi.  Check out how you can create, market, and sell your own digital products through the power of the platform at Kajabi.  And let them know that The Nathan Barry show sent you.

Today we’re sharing what sorts of things you should give away to build your brand and how to create them. Content is a great way to up your value and really fine tune your audience. There are a few important things to consider when picking an audience, and it’s important that you choose wisely. Strive to maintain a personal brand, instead of a subject-based brand; that way, even if you deviate, you’ve created an audience that follows you. Paul Jarvis dives into his biggest mistakes when trying to begin a career in writing, why he ended up releasing a vegan cookbook, and the success story behind it. He shares a lot of great information with us today, including: What he’s pursuing and who his audience is The one thing that all content marketers are getting wrong His top tip for a person with a budding audience How he attracts clients by focusing on business and “what’s in it for them” The unexpected benefits of having an audience We wrap it up by talking about the importance of over delivering now to get great results later, how we batch our content and articles, and how Paul used Medium and Amazon to boost his articles to the number one spot. Paul has distributed over 100,000 copies of his book “Everything I Know”, and currently has about 25,000 e-mail subscribers. He’s been crazy successful, and was happy to share a wealth of tips and advice with us today from his journey. Links and resources: The Audience Building Challenge by Nathan Barry The Freelancer podcast Invisible Office Hours podcast Paul’s website The Creative Class by Paul Jarvis Paul on Medium Paul on Amazon Be sure to check out Paul’s stuff, and if you have a minute, I would really appreciate if you would write a review on iTunes about today’s episode. Whether it’s good or bad, let us know what you think by posting a review in iTunes.This season of The Nathan Barry show is sponsored by Kajabi.  Check out how you can create, market, and sell your own digital products through the power of the platform at Kajabi.  And let them know that The Nathan Barry show sent you.

Wracking your brain trying to develop the best marketing campaign? When you think about it, marketing is really just big companies competing for attention. But I’m here to tell you about one of the biggest cheats these companies are missing out on. While they’re too busy fighting each other over a few seconds of everyone’s time, you can be working toward building an audience. That’s right, an audience. When you have an audience, you already have a group of people who want to pay attention to you!I’ve created this podcast to help those of us running our own businesses online build our audiences and our success. I’m talking about personal experiences, I’m bringing on guests who have used social media in unique and interesting ways, and I’m going to teach you how to build yourself an audience that goes beyond creating a simple email list. On today’s episode, I’ve invited Jason Zook to talk about how his audience helped build his brand and helped him succeed as an entrepreneur.“Building a really great audience that you have a conversation with is only going benefit everything that you’re doing tenfold,” Jason says on today’s show. And he offers advice on email marketing and building an online community that you can start using today in order to start that conversation. Along with his insights, this podcast is chock full of tips for: Getting your customers excited about your brand Learning the difference between hard work and luck Building an online community that’s dedicated to your brand and your products Jason’s peculiar insight on what it’s like to auction off your own last name Listen in and let us know what you think! Share your audience building tips, let me know what topics you want to hear about, and leave us a review on iTunes.This season of The Nathan Barry show is sponsored by Kajabi.  Check out how you can create, market, and sell your own digital products through the power of the platform at Kajabi.  And let them know that The Nathan Barry show sent you.

Nothing I do is completely original. In fact, so many ideas that people credit to me are originally from someone else.In this episode I want to give credit to the people who’ve provided some truly impactful ideas to the world. This is not a complete list by any means; I’m sure I’ve missed someone, so I plan to add to this list over time. I hope you enjoy it, and feel free to leave a comment if you have something to add!Show Notes1. Slow, consistent progressLifehacker article on “Don’t break the chain”(Seinfeld said he didn’t come up with this, but I’m still going to believe he did :)2. Writing 1,000 words per dayChris Guillebeau first introduced me to the idea of making consistent progress in order to actually finish a book. Here’s his post on the topic: How to Write 300,000 Words In 1 Year.3. Writing to a painAmy Hoy and Alex Hillman gave me a solid introduction to copywriting. Through plenty of direct feedback on my sales pages I learned all about writing to a particular pain in my headlines and copy. Amy and Alex go on to talk about the pain, dream, fix model of writing sales pages.You can find Amy & Alex here.I haven’t taken their course 30×500, but I’ve heard wonderful things about it.4. Multiple packagesAn offhand comment by Chris Guillebeau has made me tens of thousands of dollars. 5. Selling digital productsTim Ferriss talks about drug dealers in 4HWW.6. Making a living from self-publishing to a small audienceSacha Greif and Jarrod Drysdale showed me how it’s done.7. Travel hackingChris Guillebeau is the master of this hard-to-believe travel methodology. 8. Focusing on a few core productsJeff Goins, Laura Roeder, & Sacha Greif are excellent examples of this.9. Syndicating content instead of guest postingJames Clear taught me that your best content should appear on your own site.10. Webinars to grow an audienceBrennan Dunn, Danny Iny, Jeff Goins, & Brad Fallon taught me everything I know about how to run profitable webinars and joint ventures. 11. Email marketingConvertKit Academy is something I built for authors who want to learn how to connect better with their audiences and apply email marketing best-practices so they can sell more books.  

In the previous part of this episode we met three talented people – Brandon, Samuel, & Jason. We chatted a bit about their successes with self-publishing and learned how they used my book Authority as a roadmap for creating and publishing their work. In this episode, we dig deeper into how each of these fine gentlemen came up with the topics for their books, dealt with technical challenges, and got the word out. They also share several ways in which their lifestyles improved as a result of their successes; you definitely don’t want to miss that section.Hope you enjoy!Show NotesBuild a Ruby Gem – the book Brandon Hilkert launched after reading Authority Professional Email Design – the latest project by Jason Rodriguez following the success of his first book The Elements of User Onboarding – author Samuel Hulick claims to have botched his book launch, but still managed to land some lucrative consulting gigs (and over $37,000 in revenue) ConvertKit – a tool I built to help creative people get a landing page up faster so they can build their email lists, launch products, and get more sales.Real people have used the information in Authority to earn hundreds of thousands of dollars selling educational products to their enthusiastic audiences. Get your copy of Authority to find out how you can too.Or you can check out what a few people have said about Authority on Amazon. 

Have you ever wondered if it would be possible to make an independent living selling your expertise? In my book Authority I lay down an end-to-end plan for how to research, write, and publish a book to an excited and profitable audience so you can do just that. As it turns out, the methods I outline in Authority work extremely well for many people. Luckily I was able to get a few people who’ve had amazing success on a hangout; we talked for a while about their experiences publishing their first books (and earning very impressive revenues from them). Keep in mind that none of these talented folks had big audiences when they started.This is part 1 of a two part episode showcasing some of our most successful Authority customers. Hope you enjoy!Show NotesBuild a Ruby Gem – the book Brandon Hilkert launched after reading Authority Professional Email Design – the latest project by Jason Rodriguez following the success of his first book The Elements of User Onboarding – this breakthrough book by Samuel Hulick landed him some sweet consulting gigs (and over $37,000 in revenue) How to make a full-time salary from one book – an article I wrote since this recording outlining what I’ve learned from multiple book launches.Real people have used the information in Authority to earn hundreds of thousands of dollars selling educational products to their enthusiastic audiences. Get your copy of Authority to find out how you can too.Or you can check out what a few people have said about Authority on Amazon. 

Why don’t people share financial numbers? In this twenty-minute audio essay I delve into some of the reasons why people are afraid to be financially transparent, and why I’ve chosen to ignore those reasons in favor of exposing my revenue numbers (and why you should too). Show NotesSacha Grief – one of the people who’s inspired me most to start publishing books and be transparent about the process. Jarrod Drysdale – a great designer and one of the inspirations behind my design books. The App Design Handbook launch – here’s the blog post I published where I revealed all my launch numbers – and got accused of bragging as a result :-D Want to try something fun? Leave a comment below with a financial number you’re comfortable sharing. It could be anything from your latte budget to how much your most recent product launch made!

One of the most effective ways to show potential customers how your product could be useful to them is to feature it in a promo video. Well-made promo videos can be inspiring, insightful, and fun. The problem is, video can take a bit of time to learn how to do right. Luckily I have a good friend who runs his own video production studio. His name is Caleb Wojcik; you might know him from Fizzle, which he recently moved on from to run his studio full time. If there’s one person I’d recommend to take video production advice from it’s definitely Caleb. I recently asked him to hang out with me and talk video for an hour; we dug into gear, production techniques, and some sweet hacks to make your editing workflow quicker. This episode will be especially insightful if you’re thinking about making a promo video for your product. Enjoy!Show NotesCaleb Wojcik’s DIY Video Guide – if you’re getting into making promo videos for your business, I can’t recommend this guide enough. Caleb Wojcik’s gear guide – we talked a bit about gear, but it’s way too easy to waste time figuring out what gear to buy instead of actually making videos. Luckily Caleb’s done all the work for you in this free guide. Pat Flynn’s website – we mentioned our friend Pat a few times; here’s his site if you haven’t had a chance to see his work yet. Wistia’s “down and dirty” lighting kit – for less than $100 you can make your own professional lighting kit, my friends at Wistia show you how.Caleb and me hanging out – the live hangout this podcast recording is taken from.

If you dream of selling your own products and creating a lifestyle of flexibility and independence, it’s going to be pretty tough to do that without an audience. Not only that, but that audience must be comprised of people who love what you do and have the financial means to pay you for solutions to their problems. There are many ways to build an audience, but very few of those methods lead to a profitable audience.In this short audio essay, I share with you three habits which helped me build an audience of amazing people – people who not only love what I do, but also get a ton of value from my products. They’ve been the key to my success, and if you build your audience the right way, it can be a game changer for you too. Enjoy this quick listen! Building a profitable audience takes time, and it can be a difficult process without guidance. Luckily I wrote an entire book about how to build a profitable audience from scratch – and how to create a valuable product you can sell to them. Real people have used the information in Authority to earn hundreds of thousands of dollars selling educational products to their enthusiastic audiences. Get your copy of Authority to find out how you can too.Or you can check out what a few people have said about Authority on Amazon. 

This is part two of the live event Sacha Greif and I put together in August of last year. As a reminder, you can watch a video of the event here, and you can listen to part one here if you missed it. Enjoy part two of The Self-Publishing Hangout!Sacha, Justin, and Paul are all super helpful, knowledgeable, and experienced in their respective fields. You should definitely follow them and subscribe to their email lists. Here’s where you can find them online: Sacha Greif  Justin Jackson  Paul Jarvis

In August last year Sacha Greif and I put together a live event called The Self-Publishing Hangout. We brought on Paul Jarvis and Justin Jackson to round out our panel. You can watch a video of the event here, or checkout my podcast episode below.   Since recording that episode each of the guests have gone on to do amazing things. You should definitely follow them and subscribe to their email lists. Here’s where you can find them online: Sacha Greif  Justin Jackson  Paul Jarvis See you in part 2!

Today I’ve got my absolute favorite product creation and launch story to share with you! Sean McCabe started as a web design consultant, then built up a following for his true passion: hand lettering.He then started teaching and grew a massive email list and then launched a training product. He shares the story and all the launch details (including exact revenue numbers) in this episode. Here’s where you can find Sean on the web: His main site, Seanwes.com The seanwes podcast His new book, The Overlap Technique His tshirt and print store And finally, the wildly successful Learn Lettering course Here you can see the very first tshirt Sean sold in his store.      Don’t forget to subscribe on iTunes.

Few things have paid off better in my business than a focus on email marketing. In building my list up to 18,000+ subscribers I’ve learned that email is the most profitable marketing channel around. Easily beating out Twitter, Facebook, and YouTube.To learn more about email marketing I brought on three of my good friends: Brennan Dunn, James Clear, and Corbett Barr. All three have built highly profitable email lists in the last few years.Enjoy the episode!You can find each of their businesses (and subscribe to their lists) here: Corbett Barr — Fizzle.co Brennan Dunn — Planscope.io, BrennanDunn.com James Clear — JamesClear.com Please go to iTunes and subscribe and write a review. It would really help me out!See you in the next episode! 

In January 2013 I wrote a series of goals for the year. One of them was “launch a podcast.”How does a goal like that take 18 months to be realized? Well, first I created all kinds of reasons that a podcast was much harder than it actually needed to be. Finally after recording episodes and working sporadically on it for over a year, I’m ready to launch!This first episode is a short book I wrote called The Productivity Manifesto. If you read my last post you know that productivity is something I’ve excelled at in the past, but am struggling with right now. So it seemed like a good topic to revisit for episode one.After listening please do me a huge favor and write a review on iTunes. Good reviews are critical to getting an audience for a brand new show.See you in the next episode!