David Tisch is the Managing Partner of BoxGroup, one of the leading seed-stage investment firms of the last decade having invested in over 500 seed-stage startups, including Plaid, Ro, Ramp, PillPack, Amplitude, Stripe, Warby Parker, Harry’s, Flexport, Classpass, Airtable and more. Terrence Rohan is the Managing Director @ Otherwise Fund, a fund that discretely empowers a network of today's top founders to make multi-stage venture investments. Terrence has invested in the likes of Figma, Hugging Face, Vanta, Notion and Robinhood to name a few. In Today's Seed Investing Special We Discuss: 1. Is Seed Investing Now a Commoditised Asset Class: Why does Dave Tisch believe seed investing will remain the most inefficient market? What does that mean for the future of returns at seed? Why should you always pay up and be price-insensitive at seed rounds? Why does David believe that no one is great at seed investing? Why does David believe that you cannot index the seed market? 2. The Biggest BS Elements of Venture Capital: Signaling: Why does David believe that the theory of signaling is total BS? Why does Terrence disagree and think it is valid and common? Group Decision-Making: Why does Terrence believe that investing decisions should be made solo and groups merely encourage consensus decision-making? Reserves: Why does Terrence believe reserves hurt DPI and are not good? How does David respond given his growth fund? Venture Value Add: Why do David and Terrence think venture value add services platforms are BS and not worth it? 3. The World of LPs: What is the single biggest misalignment between VCs and LPs? What are David and Terrence's biggest pieces of advice for emerging managers today? Should LPs expect depressed returns from venture as the asset class commoditises?

Will Wu is the CTO @ Match Group, the owner and operator of the largest global portfolio of popular online dating services including Tinder, Match.com, OkCupid, and Hinge to name a few. Prior to Match, Will was VP of Product at Snap Inc. As the 35th employee, Will spearheaded the creation of Snapchat’s “Discover” content platform. He also led the creation and growth of the “Chat” messaging feature, which today is a primary Snapchat engagement driver that connects hundreds of millions of people each day. In Today's Episode with Will Wu We Discuss: 1. The Journey to Snap CPO: How did Evan make his way into the world of product and come to meet Evan Spiegel? What are 1-2 of his biggest takeaways from his time at Snap? What does Will know now that he wishes he had known when he started in product? 2. How to Hire Product Teams: How does Will structure the interview process for new product hires? What are the most telling questions of a candidate's product skills in hiring? What case studies and tests does Will do to assess a candidate? What are 1-2 of Will's biggest hiring mistakes in product? 3. How to Do Product Reviews Effectively: What are Will's biggest lessons on what it takes to do product reviews well? What are the biggest mistakes product leaders make in product reviews? How can teams drive focus in product reviews? What works? What does not? 4. Product: Art or Science? How does Will balance between gut/intuition and data in product decisions? Is simple always better in product design? What is human-centered design? How does it impact how Will approaches product?

Dave Kellogg is one of the OGs of Saas. Among his many accomplishments, Dave was the CMO of Business Objects where he helped scale the business from $30M to $1BN in revenue. Dave has also been a CEO twice, once scaling the business from $0 to $80M and the other business from $8M to $50M before selling it. Dave is also an advisor to some of the best including GainSight, Logickull, MongoDB, Pigment, Recorded Future, and Tableau. In Today's Episode with Dave Kellogg We Discuss: 1. What are the Metrics That Matter: Why is CAC payback period such a flawed metric? What is CAC ratio? Why is it more effective than understanding payback? Why is gross revenue retention more important than net revenue retention? What are the single biggest mistakes that founders make when using metrics today? 2. How to Build and Scale the Best Sales Teams: Why should founders hire three sales reps at one time? What is the benefit? What are the three different types of sales calls all teams must have? What should all CEOs and Heads of Sales ask of their sales team in forecasting? What is the single biggest mistake most companies make in forecasting? How should a CEO/board member respond to a sales team that lets a deal slip to next quarter? 3. Are CFOs Buying New Tech and How to Win Renewals: Are CFOs open for business? How has the top down sales process changed in the last year? Why is the way that startups think about renewals completely broken? What are the three different types of customer success teams we have today? What is the core role of customer success? How can we incentivise them to sell more? 4. Mastering Product Marketing, Customer Profiles and Crossing the Chasm: How can we use product marketing to increase sales velocity? What is the single biggest risk in product marketing today? What does Dave mean when he says "an ICP starts as an aspiration and becomes a regression?"

Ryan Akkina is a member of the Global Investment Team at the MIT Investment Management Company (MITIMCo), which is responsible for managing MIT's endowment and pension plans. Ryan has invested in the likes of Sequoia, Kleiner Perkins, a16z, Greenoaks and Initialized to name a few. Ryan also leads many of MITIMCo's direct co-investments including most notably into Coupang and Rippling. Prior to joining MITIMCo, Ryan was a consultant at McKinsey & Company. In Today's Episode with Ryan Akkina We Discuss: 1. From Engineer to LP with MIT: How did Ryan make his way into the world of fund investing as an LP with MIT? Why did he turn down the chance to be a VC early in his career? What does Ryan know now that he wishes he had known when he started at MIT? 2. The Manager Evaluation Process for MIT: What does Ryan look for most when investing in new managers? How important is track record when evaluating a new manager? What is the biggest mistake Ryan has made in picking a manager? What did he not see that he wish he had seen? How did that change his process? 3. How MIT Builds Their Portfolio: How does MIT construct their portfolio from private to public to everything in between? What are the three different types of check sizes that MIT writes when investing in new managers? What are the most common reasons why MIT will not re-up with a manager? What are the single biggest reasons why great managers turn bad? 4. MIT: The Direct Investor: Why does MIT see so much opportunity in direct investing? How does MIT approach the direct investing process? How do they approach underwriting themselves vs working with their managers in the process? How do MIT think about the right number of direct deals to make up their portfolio? How do they approach check sizing on a per-company direct investment? What has been Ryan's biggest direct investing mistake? How did that change his approach and mindset? 5. LP Markets Today and Where We Go From Here: Are LPs open for business today? What type of firms will not struggle? Which will? How does Ryan view liquidity windows today? When will M&A and IPO markets open? What would Ryan most like to change about the world of LPs? Why does Ryan believe the LP incentive structure in terms of compensation is broken?

Dave Ripley is the CEO @ Kraken, one of the world's largest cryptocurrency exchanges, valued in 2022 at a whopping $10.8BN. Prior to Kraken, Dave was the Co-Founder of Glidera, a market-leading Blockchain technology company that Kraken acquired in 2016. In Today's Episode with Dave Ripley: 1. From Boston Consulting Group to CEO of Kraken: How did Dave first make his way into the world of crypto? What are the single hardest elements of a CEO transition? What does Dave know now that he wishes he had known about CEOship? 2. What is the Usage for Crypto: Other than as a store of value, what application usage does crypto serve? Global payments are fine as is and are improving, why do they need crypto? Global remittance is served by Remote and Deel, why do they need crypto? No applications have been provided well, what really is the use case that makes sense? 3. Should Gensler Be Let Go and The SEC is Wrong: Why is the approach of the SEC completely flawed? Should Gensler be fired for his ineffectiveness? What is the right policy stance and approach to take from here?

Sean Murray is the CRO @ Greenhouse which is the fourth company Sean has scaled successfully into the enterprise. Sean's prior roles include revenue leadership positions at Saleloft (CRO), Xactly (VP Sales), and CEB, now Gartner (Head of MID Global Sales). In Today's Episode with Sean Murray 1. The Origin Story: Is a Love of Sales Born: How did Sean first fall in love with Sales? What does Sean know now that he wishes he had known when he started his career in sales? What is Sean's biggest advice to a young person entering the sales world today? 2. Sales has Changed; You Need to Change with It: Why do CMOs need to be good sellers and CROs need to be good marketers today? Have we seen the total blending of sales and marketing today? Should we get rid of all sales teams and just have content marketing teams? 3. How to Move into the Enterprise Successfully: What are the three biggest mistakes startups make when scaling into the enterprise? What easy wins can they do early in the sales process to enterprises to get a good start? How important are logos? Does social validity really work in enterprise? How should sales teams use discounting in enterprise sales most effectively? What is the right way for sales leaders and CROs to budget for enterprise? Is there a way to test enterprise without committing the company and a lot of resources? 4. How to Build the Best Sales Team Today: What is the right hiring process for all new sales hires? What are the questions you have to ask in the interviews? What do the case studies entail? What are signals of the best reps? What are the biggest mistakes teams make when hiring new sales reps? What have been Sean's biggest lessons on comp and negotiation with new reps?

Adam Fisher is a Partner @ Bessemer Venture Partners and one of the most successful investors in Israel over the last two decades with seed investments in Fiverr, Wix, Melio, HiBob and more. Adam has now made over 60 investments and has had an incredible 23 successful exits. Adam has now been in venture for over 27 years having started his career at Jerusalem Venture Partners in 1996. In Today's Episode with Adam Fisher We Discuss: 1. Lessons from 27 Years in Venture Capital: How did Adam first make his way into the world of venture straight out of college? Does Adam agree with Doug Leone that VC has changed from a "boutique, high margin business to a commoditized, low margin industry"? What does Adam know now that he wishes he had known when he started in venture? 2. How to Pick Winners: 23 Exits in 60 Investments: To what extent does Adam think pattern recognition is a good thing? When is it bad? Does Adam prefer to invest in outsider founders approaching a problem with fresh eyes or insider founders who know the problem back to front? Why does Adam believe that "category creation is BS"? Why does Adam not like to invest in big, hugely ambitious markets? Why are smaller markets best? 3. The Deal: Mastering the Art of Negotiation and the Deal: How does Adam reflect on his own relationship to price? When doing an investment, does Adam think about who would do the next round? How important is ownership to Adam? Does he want it all on first check? Why does Adam not like to invest in hot AI rounds? What have been Adam's single biggest investing mistakes? How did it change his approach? 4. Mastering the Art of Portfolio Management: Why does Adam believe that it is impossible to know which of your portfolio will be the breakout winners early on? How does Adam approach reserve allocations with this in mind? How does Adam know when is the right time to sell a position? What does Adam believe was the biggest sin of the zero interest rate environment period?

Zaria Parvez is Duolingo’s Senior Global Social Media Manager where she is famed for scaling Duolingo's TikTok from 50K followers in September 2021 to 8M followers today. The Duolingo TikTok has 143 viral videos (view counts of 1M or higher) due to Zaria’s creativity. What started as a test-and-learn initiative has become Duolingo's most successful social buzz and word-of-mouth initiative to date – all because of Zaria's insights, instincts, and expertise. In Today's Episode with Zaria Parvez: 1. From College Student to TikTok Star: How did Zaria make her way into the world of social media and Duolingo? When did Zaria realize the power of TikTok? What did she do as a first step? What does Zaria know now about growing on TikTok that she wishes she'd known when she started? 2. How to Create a Viral Video: What have been Zaria's biggest lessons in what it takes to create a viral video? What does Zaria mean when she says the best content is "medicine to candy"? What does the ideation process look like for new content ideas? How much budget should be set aside for new content? What does Zaria mean when she says Duolingo's TikTok needs to view like a "sitcom"? 3. How to Tie Success in Content Back to Hard Dollars: How is "success" in content measured at Duolingo? How fast does Zaria know if a video is a hit or not? What is the right cadence to post? How should companies determine whether content is ultimately successful or not? What is the single metric that Zaria is focused on today? 4. How to Build the Best Content Team: Why should companies not work with content agencies if they want the best results? Why does Zaria believe you have to hire troublemakers if you want success in content? What are the single biggest mistakes companies make w

Shyam Sankar is Chief Technology Officer and Executive Vice President of Palantir Technologies in addition to the Chairman of Ginkgo Bioworks. Shyam holds a B.S. in Electrical and Computer Engineering from Cornell University and a M.S. in Management Science and Engineering from Stanford University. In Today's Episode with Shyam Sankar: 1. Journey to the Top of Defence: How did Shyam make his way into the world of startups and get a role with Kevin Hartz at Xoom? How did seeing Shyam's parents lose everything impact his mindset and drive? What does Shyam know now that he wishes he had known when he started his career? 2. How the World's Governments Buy Defence: What is the playbook for selling defence to different governments? Why is the way that governments purchase and procure so broken? If Shyam were head of the DOD, what would he change? Why does the DOD "need to pick winners"? Which governments are the best to work with? Which are the worst? 3. A World In Conflict: What Changes: How does conflict change the buying process and urgency for governments? How do elections change the buying cadence and process for different governments? Looking forward to 2024, how does Shyam predict the state of different global conflicts? 4. Hiring 101: You Have To Hire Artists: What have been Shyam's single biggest lessons on what it takes to hire the best of the best? Why does Shyam believe that hiring great people is like talent management in Hollywood? Why does Shyam believe talent should be "shielded from budgets"? What have been some of Shyam's biggest hiring mistakes? How did he learn from them?

Brian Halligan is the Co-Founder and Executive Chairperson of HubSpot. Brian led the business as CEO for 15 years from Day 1 to a $30BN public company with 7,000 employees. Among Brian numerous achievements, Brian is famed for coining the term "inbound marketing", he is a globally recognised author, he is also an incredible teacher having developed MIT’s popular Scaling Entrepreneurial Ventures class. In addition to all of this, he is also the Co-Founder of Propeller Ventures, a $100 million climate tech venture fund, specializing in ocean innovation investments. In Today's Episode with Brian Halligan We Discuss: 1. The Makings of a Generational Defining Entrepreneur: How did the first job as a paperboy lead to the founding of a $30BN company? How does Brian analyse the importance of luck vs skill in success? What is Brian running from? What is he running towards? 2. How to Be the Best Leader from 15 Years as CEO: What are Brian's biggest lessons in leadership from Elon Musk and Jensen Huang? How has Brian's leadership style changed over time? Why is the way leaders prioritise what they do today completely broken? How can leaders use quarterly goals to prioritise most effectively? Does Brian believe people are born CEOs? Are MBAs worth it for CEOs? 3. How to Build the Best Team: What is the #1 failure condition of teams today? Why does Brian believe most of your employees are mercenaries and not missionaries? Is that ok? Why do recovery plans never work? Once lost, can trust in teams be regained? Are people destined for certain stages of company growth? Why does culture always break when teams hit 100 people? 4. The Best Deal in VC History: Why did Hubspot sell 47% of the company to General Catalyst in their Series A? How did Sequoia come to lead their Series D? How much of a needle mover is it for companies and founders to have Sequoia invest? Why did Brian sell secondary to Sequoia in the Series D? Is it the most costly mistake he has made?

Keith Rabois is a Managing Director @ Khosla Ventures and one of the most respected venture investors of the last decade. Keith has led investments in Stripe, Faire, Ramp, Affirm and many more. Just last week, Keith announced he would be rejoining Khosla from Founders Fund, where he spent an immensely successful 5 years as a General Partner. Prior to Founders Fund, Keith started his career at Khosla where he spent 6 years and led investments in DoorDash, Opendoor, Webflow and more. In Today's Episode with Keith Rabois We Discuss: 1. The Decision to Rejoin Khosla Ventures: Why did Keith decide to rejoin Khosla Ventures from Founders Fund? What did Keith miss most that Khosla did, that Founders Fund did not? How did Delian take the news? 2. Comparing Two Great Firms: Founders Fund vs Khosla Ventures: Investing Style: How does Keith compare the investing styles when analyzing FF and KV? Price Discipline: Which firm is more price-disciplined? Does price discipline even matter? What are the single biggest mistakes Keith has made on price? How did it change how he invests? Founder Type: What sort of founder would choose KV? What founder would choose FF? How did the depth & quality of investment decision-making compare between KV and FF? 3. What It Takes To Win in Venture in 2024: Liquidity: What have been Keith's biggest lessons on when is the right time to sell positions? Capital Planning: What have been Keith's biggest lessons on the most effective use of reserves? Why does Keith believe if you do not lose some deals as an investor, you are not competing for the right companies? Khosla Ventures recently raised $3BN. How important is the ability to support companies across their lifetime in 2024 vs stage specific? 4. Where is The Best Place to Invest: Why does Keith think seed is the best place to be investing today? Why despite the better risk/reward profile, does Keith think Series A is not the best place to invest? Does Keith believe we will see the return of growth investing in 2024? What does Keith predict for the M&A market in 2024? Did Figma kill all activity? When will the IPO windows open again? Why would Stripe go out this year? 5. Keith Rabois: AMA: Why did Keith not want to start his own fund? Will he ever? What have been Keith's biggest lessons from working with Vinod Khosla and Peter Thiel? What were Keith's biggest lessons from Roelof Botha on what it takes to be an effective board member? How does Keith think about bitcoin in 2024?

Jamin Ball is a Partner @ Altimeter Capital where he sits on the board of Airbyte, Clickhouse, dbt Labs, Prisma, Tabular. Jamin has also led investments in Deel, MotherDuck, Personio and Starburst. Prior to Altimeter, Jamin spent 5 years at Redpoint where he led investments in Workato, Monte Carlo, Cityblock Health, Root Insurance. Ed Sim is one of the best seed round investors in venture as the Founder and Managing Partner @ Boldstart, Ed focuses specifically on developer, infra and SaaS at pre-seed and seed round. Over the last decade, Ed has backed some of the best including Snyk, BigID, Kustomer, Front and Superhuman. In Today's Episode We Discuss: 1. How to Invest Successfully in 2024: What are the three biggest mistakes growth investors can make in 2024? Why should founders not start a platform company? What were Jamin and Ed's biggest mistakes from the ZIRP era? How does Jamin justify paying an $8BN price for Hopin? What were his lessons? 2. The M&A Markets in 2024: Did Figma kill the M&A markets for 2024? What should we expect in M&A? Why will private companies buying private companies be a massive segment in 2024? What are Ed and Jamin's biggest tips to founders considering selling their company in 2024? 3. When Will IPOs Come Back: What will be the catalyst to the opening of the IPO markets? Will Stripe and Databricks go public in 2024? What others should we expect? What are the three requirements for a company to go public in 2024? 4. Firesales: Investors Need Cashback: Why does Ed believe now is the time in the cycle where late-stage investors want cash back to distribute back to their LPs or to recycle? What should we expect to see in terms of acqui-hires and firesales? What are the different incentives when comparing founders vs early stage VCs vs late stage VCs when it comes to acquisitions?

Nick Tomaino is the Founder and General Partner @ 1confirmation, one of the leading seed firms fueling the decentralization of the web and society. The fund started with $26M and the firm now has over $1B in assets under management. Nick is famed for being one of the first investors in OpenSea. Kyle Samani is the Co-Founder and Managing Partner @ Multicoin Capital, one of the leading crypto native funds of the last decade with positions in Solana, FTX, Fractal, and Helium to name a few. In Today's Episode We Discuss: 1. Moving Away from a Shitcoin Casino: What will it take for crypto to move away from being shitcoin casino? Why does Nick believe that "crypto has been a free for all and greed got the better of people"? Why does Nick believe that crypto shilling will reduce the amount of violence in the world? 2. FTX: The Biggest Ponzi Scheme in Plain sight: How does Kyle reflect on SBF and FTX today? Should he have known it was a fraud? How did Nick see so far ahead of time that SBF was not genuine? What are the most striking lessons when comparing Coinbase's Superbowl advert to FTX's? 3. Where Politics and Crypto Collide: SBF was one of the largest donors to Biden, what does this say about the rise of "crony capitalism"? What candidates running in the election will be best for crypto? Why will Trump win the election and be the first President to rule from a prison cell? Why is the strategy pursued by Gensler and the SEC so flawed? 4. The Great NFT Comeback, The Crypto IPO Season: What will be the next crypto company to IPO? When? When will NFTs come back? What will cause this? Will Opensea ever be worth $13BN again? What is their future?

Joining Harry in the hot seat today is Jason Lemkin, Founder @ SaaStr and one of the OG SaaS investors of the last decade. The discussion today is broken into two segments: 2023: A Year in Review: Breakout company Best early-stage fund Best late-stage fund Most surprising event Founder of the Year 2024: Predictions: What is to Come: Does the IPO window open? Do Stripe, Databricks, and more go public? What happens to early-stage venture markets? Does the growth stage come roaring back? What happens to the M&A market? How does Trump change the startup ecosystem? Will a generation of young VCs be washed out the system? Will a ton of venture firms shut down?

Dave Powers serves as President and CEO of Deckers Brands, a global footwear and apparel company where he focuses on the company’s five high-performing brands: UGG®, Teva®, Sanuk®, HOKA One One® and Koolaburra®. Prior to Deckers, he held executive leadership roles at Converse and Timberland, where he led worldwide retail merchandising, marketing, visual and store design as well as the creation of a sustainable line of footwear and apparel. In Today's Episode with Dave Powers: 1. The Unlikely CEO of a Global Footwear Company: How did Dave make his way into the world of consumer and fashion from the ground up? Why did Dave never think he was the type of person to be a CEO? What does Dave know now that he wishes he had known when he started his career? 2. From $1.1M Acquisition to $1.4BN Revenues: The Hoka Story: Why did Deckers acquire Hoka for $1.1M? What did they see in this, at the time, futuristic running shoe that no one else saw? Was the growth of Hoka linear or were there needle-moving moments that propelled the brand? What did they do so right that led to their success? What would Dave have done differently in the Hoka journey if he had his time again? 3. From $14.7BN Acquisition to Oprah's Favourite: The UGG Journey: How much of a needle mover was it for UGG when Oprah added it to her list of favourite items? Why did UGG go through a tough period? What did they do wrong? What does it take to resurrect a brand? How can they bring UGG back to life and make it cool? 4. From Abercrombie to LVMH: An Analysis of the Industry: How does Dave analyse the rise and fall of Abercrombie and Hollister? Where did it go wrong? What does Dave believe LVMH are the best in the world at? What does he learn from them? How important is it for consumer companies to have a hero product? How can consumer companies scale to mass markets without losing their core audience?

Gustav Söderström is the Co-President, CPO & CTO at Spotify. Gustav has been instrumental in taking Spotify from a 30-person operation in Sweden when he joined to being the global leader of the space. Scott Belsky is Adobe’s Chief Product Officer and Executive Vice President, Creative Cloud. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe.  Tomer Cohen is the Chief Product Officer @ Linkedin where he is responsible for setting and executing the global product strategy at LinkedIn. In Today's Episode on How AI Changes The Future of Product and Design We Discuss: 1. Why AI Is Now the Product that UI Serves: Why does Gustav believe that AI is now the product? How has the importance of UI changed with the rise of AI? How did TikTok change the product paradigm over the last few years? 2. What Matters More Models or Data: What is more important the size of the model or the amount of data a company has? Will companies use many models at the same time? Why will companies using many models at once create a huge opportunity for startups? Will every company have their own model? What will be the decision-making framework of whether to have your own model or leverage another? How does the rise of AI change how companies approach data acquisition, collection and cleaning? 3. The Workforce Needs to Change with AI: How do product leaders and teams need to change in an AI-first world? What do designers need to do to stay up to date in an AI-first world? What does it mean to be good at prompting? How can people get good at prompting? Why will AI kill companies that charge by the hour? Why will seat pricing die in a world of AI? What will be the business model for AI? 4. Incumbents vs Startups: Who Wins: Do incumbents win in a world of AI or do startups? Why is AI primed for incumbents to win and move fast in a way they could not in prior technology cycles? What are the biggest hurdles and challenges incumbents have to face that startups do not? What are the biggest barriers that startups have to win in a world of AI that incumbents do not have?

Peter Lacaillade is a Managing Director @ SCS Financial Services where he leads its private investment program where he oversees the firm’s activities in private equity, opportunistic credit and private real assets. Peter has been an early backer of Thrive, Founders Fund, a16z, Greenoaks and 20VC. Before SCS, Peter was an Associate at HarbourVest Partners in its Secondary Group where he analyzed venture capital, growth equity and buyout investments. In Today's Episode with Peter Lacaillade We Discuss: 1. Becoming One of the Great LPs in Venture: How did Peter make his way into the world of fund investing as an LP? What does Peter know now that he wishes he had known when he started as an LP? Why does Peter believe now is the best time to be investing in newer, emerging managers? 2. How to Pick the Best Venture Managers: What are the commonalities in the best VCs Peter has invested in? How important is track record for Peter when evaluating managers? What mistakes has Peter made when it comes to manager selection? What did he learn? How do the best managers build relationships with their LPs? 3. Building a Portfolio That Can 5x: In a venture fund portfolio, what is the distribution between those that outperform, perform as planned and then underperform? How does Peter invest in both large franchises and emerging managers with a barbell approach? How much in established franchises and how much in emerging managers? Are managers actively marking down their portfolios in the last 18 months? Who has been the best at this and who has been the worst? How much should portfolios be marked down? How does Peter evaluate the compression of deployment timelines we saw in the last 18 months? 4. A Breakdown of the LP Landscape: Family Offices: What are the biggest dangers of having family offices as LPs? Why do multi-family offices tend to be better? Endowments: Are they really as stable as people think they are? What separates a good vs great endowment? Who stands out? Fund of Funds: Why does Peter think fund of funds deserve more credit? How should managers think about working with FoFs most effectively? What is the right level of concentration managers should have between these different LP profiles? What are the biggest mistakes emerging managers make when approaching LPs?

Davis Smith is the Founder and Chairman of Cotopaxi, an outdoor brand with a humanitarian mission. The company has assisted over 4 million people living in poverty. The company has been profitable for the last 4 years and is expected to do $160M in revenue in 2023, up from $55M just two years before. In April 2023, Davis resigned after 10 years as CEO to lead a mission for his church in Brazil for three years. Davis is an EY Entrepreneur of the Year and was recognized as Utah’s Businessperson of the Year in 2022. He is an adventurer who has floated the Amazon on a self-made raft, kayaked from Cuba to Florida, and explored North Korea. In Today's Episode with Davis Smith We Discuss: 1. From Selling $6M Worth of Pool Tables to the Amazon of Brazil to Founding Cotopaxi: How did Davis scale a pool table business to $6M in revenue? What were Davis' biggest takeaways from building the Amazon of Brazil, raising millions in VC funding and the business failing? How did depression and 36 hours on a sofa lead to the a-ha moment for Cotopaxi? 2. The Billion Dollar Company, Rejected by 100 Investors: How was the early fundraising journey for Davis with Cotopaxi? Why did so many investors say no? What was the best VC meeting he has ever had? Why do women understand Cotopaxi better? What does Davis believe are the biggest misalignments between VCs and Founders? Why does Davis believe we need a new type of financial product to fund long term projects? What are the biggest elements of fundraising that Davis believes founders do not understand? 3. Scaling Cotopaxi to $150M in Revenue: What are Davis' biggest lessons on what works and what does not from scaling Cotopaxi to $150M in revenue? Why did Davis not lay anyone off but decide everyone should take a pay cut instead? How did that go down? Why does letting people leave work earlier lead to better talent wanting to join your company? Why does Davis believe that you absolutely can build a huge business with balance in your life? 4. Life, Parenting, Marriage: Why does Davis believe that so many entrepreneurs chase the wrong thing? What do they chase? What should they be chasing instead? How does Davis analyze his relationship to money today? Does it make you happy? What does great parenting mean to Davis? How has that changed over time? How does marriage change when comparing pre-kids and post-kids? Was Davis nervous about becoming a father for the first time at the age of 24?

Steve Goldberg is the Chief Revenue Officer at Salesloft, the sales engagement platform that was acquired by Vista in 2022 for $2.3BN. Prior to Salesloft, Steve was Group Vice President of Enterprise at Yext and before that was a Senior VP @ InsideSales.com. In Today's Episode with Steve Goldberg: 1. Becoming a Sales Leader: When did Steve first fall in love with sales? Why does Steve believe sales is more psychology than anything else? What can sales reps do to master the psychology of their prospects? What does Steve know now about sales that he wishes he had known in the beginning? 2. How to Close Prospects Faster Than Ever: How does Steve build relationships with prospects very fast? What questions does he ask? How does Steve know if he is really speaking to a buyer? What are the signals? How does Steve advise sales reps on getting multiple relationships within an account to prevent the potential of losing your champion? How does Steve feel about discounting? When is the right time to do it? 3. How To Do The Best Deal Reviews: What makes good vs great deal reviews? Who is invited? Who is not? Who sets the agenda? Who is responsible for what? How do deal reviews change throughout the quarter and throughout the year? Is a deal slipping into the next quarter an acceptable excuse for a sales rep to give? 4. How to Ensure Renewals in a World When They are Not Guaranteed: Have all budgets centralized back to the control of the CFO? Are people right to say that no CFOs are buying new technology today? What is the best way to show to customers the value you provide? Why does Steve believe revenue operations is the most valuable role within an org?

Sam Corcos is the Co-Founder & CEO @ Levels, the company helping you see how food affects your health with data from biosensors like continuous glucose monitors (CGMs). To date, Sam has raised over $89M for Levels from the likes of a16z (Jeff Jordan sits on his board), Founder Collective, Breyer Capital and Shrug Capital to name a few. Prior to Levels, Sam founded two prior companies, CarDash; a Y Combinator company that makes automotive repair and maintenance convenient. Before Cardash, Sam founded, Sightline Maps, an intuitive platform for 3D printing and visualizing topographical maps, marketed primarily towards the U.S. military. In Today's Episode with Sam Corcos: 1. The Founding Moment: What was the a-ha moment for Sam with the founding Levels? What were the big mistakes Sam made with prior companies that he did not take with him to Levels? What does Sam know now that he wishes he had known when he started Levels? 2. How to Fundraise Like a Pro: Why does Sam believe that founders should take as many meetings with VCs as possible? What are the biggest mistakes founders make when meeting investors? Should founders meet with associates in the fundraising process? What does Sam mean when he says, "you have to create theater" when pitching? 3. How to Extract the Most Value from Your Investors: What have been Sam's biggest lessons on how to put your investors to work? What is the right and most strategic way to ask investors for specific help? How can founders create a competitive environment where VCs are competing to help? Which investors have been the most helpful? Why are post-IPO operators the best angels to have as investors? How has the a16z platform team been such a needle mover? 4. How to Find Your Partner and Master Parenting: What does Sam mean when he says he had a "one pager" in what he wanted in a partner? What was in the one-pager? How did dates respond? What are the biggest mistakes people make when dating? What is Sam most nervous about on becoming a parent? How does Sam think having a child will impact his marriage?

Sanjit Biswas is the Founder and CEO @ Samsara, allowing businesses that depend on physical operations to harness Internet of Things (IoT) data. Over the last 8 years, Sanjit has scaled Samsara to $1BN in ARR and a public company with tens of thousands of customers. Before Samsara, Sanjit was the CEO and co-founder of Meraki, one of the most successful networking companies of the past decade. Sanjit grew Meraki from his Ph.D. research into a complete enterprise networking portfolio. Meraki's sales doubled every year from inception and in 2012, Cisco acquired Meraki for $1.2 billion. Huge thanks to Doug Leone for some fantastic question suggestions pre this episode. In Today's Episode With Sanjit Biswas We Discuss: 1. From Founding to $1BN in ARR in 8 Years: What was the founding a-ha moment for Sanjit with Samsara? Sanjit sold his prior company Meraki for $1.2BN, what worked with Meraki that Sanjit took with him to Samsara? What did not work that he left behind? What does Sanjit know now that he wishes he had known when he started Samsara? 2. The Man Who Found Product Market Fit Time and Time Again: What is the one single moment that Sanjit believes you know you have product market fit? What are the biggest mistakes founders make when chasing product market fit? How does being a bootstrapped company change how a company approaches chasing PMF? 3. Mastering a Multi-Product Company: How do you know when it is the right time to launch a second product? Does the second product have to make the first product better? What are the biggest mistakes companies make when going multi-product? 4. The Art of Great CEOship: Does Sanjit believe that the best CEOs are the best capital allocators? What has been the single best and single worst capital allocation decision in Samsara's journey? What are the biggest mistakes Sanjit has made in leadership? How did he learn and grow from them?

Geoff Charles is the VP of Product at Ramp, leading the product management, operations, and support teams. Prior to Ramp, Geoff helped spin off Mission Lane and scale credit products to millions of consumers. He started his career advising Fortune 100 financial services companies. In Today's Episode with Geoff Charles We Discuss: 1. How to Become a Product Leader: How did Geoff make his way into the world of product? What are the single most important skills for product people to learn early? What are the biggest mistakes that product people make early in their career? 2. When and Who to Hire for the First Product Team: When is the right time to hire your first product people outside of founding team? Why are the best product teams in the early days professional services teams? What is more important; the person has stage or sector experience, when joining? Should you hire senior product people or junior product people as the first hires? 3. How to Increase Velocity Using Sprints: How does Geoff and Ramp use two-week sprints to have insane product velocity? How are they structured? How are goals set? Who is included? What makes a good vs a bad sprint? How is accountability tied to sprints? When do two-week sprints no longer become possible? What happens then? 4. Going Multi-Product, Will Incumbents Kill You and Product Re-Usability: When is the right time to add a second product? What are the biggest mistakes companies make when going multi-product? Why is it unlikely that an incumbent is the one to kill you? What competitor should worry you? What does Geoff mean when he speaks of "product re-usability"? Why is it crucial to velocity?

Tooey Courtemanche, Jr. is the Founder, CEO, President, and Chairman of the Board of Procore. He founded Procore in 2002 with a mission to connect everyone in construction on a global platform. After 13 years of business, the company had just $9.6M in revenue, 8 years after that they have over $890M in revenue. Under his leadership, Procore has grown to become a leading global provider of construction management software, connecting over 2 million users across 150+ countries. Today Procore trades on the New York Stock Exchange under the ticker PCOR. Huge thanks to Brian @ Bessemer and Will @ Iconiq for some amazing question suggestions today. In Today's Episode with Tooey Courtemanche: 1. The Founding of a $8.5BN Company: How did Tooey's wife, Hilary and their house-building lead to the idea for Procore? What does Tooey know now that he wishes he had known when he started? Did Tooey always know he would be a success? What was the moment of most doubt? 2. The 13-Year Journey to $9.6M in Revenue: Why did it take so long to hit the $10M revenue mark? What changed in 2015? What is Tooey's biggest advice to founders and investors who face market timing risk? Why was Tooey laughed out of VC offices in 2008? What are his biggest pieces of advice to founders raising from VCs today? How does Tooey advise founders on the balance between vision and sticking to a mission vs realising when it is not working and giving up? 3. The Art of Great CEOship: What advice did Tobi @ Shopify give Tooey on being a great CEO? How did it impact his approach? What are the biggest differences between the reality of being a CEO and the Instagram version? What have been Tooey's biggest lessons on hiring? Why does hiring smart, ambitious but not humble people never work? Why does Tooey believe the idea of "becoming an entrepreneur" to be BS? 4. Parenting, Money and Marriage: Why does Tooey believe great parenting is like great CEOship? How does one bring up children to be ambitious and humble in a very privileged upbringing? What are the secrets to being there as a husband while also being a rockstar CEO? How does Tooey reflect on his own relationship to money and wealth today?

Dominik Richter is the Founder & CEO @ HelloFresh, one of the largest direct-to-consumer businesses of the last decade and the #1 recipe box delivery service. Fun fact, two of the three biggest cooking facilities in North America are HelloFresh facilities with the third being Disney World Orlando. Dominik has made over 40 angel investments in the EU and the US. In Today's Episode with Dominik Richter We Discuss: 1. The Founding of One of the Largest D2C Companies: How did Diminik's dreams of being a footballer translate to founding HelloFresh? What does he know now that he wishes he had known when he started? Why does Dominik respect the brands that large banks have built? 2. To Raise or Not to Raise: Why does Dominik believe when you raise VC, you either have to sell or go public? What are the single biggest differences between raising in the US vs Europe? What are Dominik's biggest pieces of advice to founders raising today? Why does Dominik believe so many of the D2C companies should not have raised venture funding? 3. The IPO: When, How and Why: Why did Dominik decide to IPO the business so early? Why does Dominik believe that the first-day trading price is irrelevant? Why does Dominik believe that timing is so important when going public? What are the biggest pros and cons of being public? 4. The Rise and Fall of D2C: D2C has been crushed lately, why? Is this the end of D2C as a category? Is D2C an investable category for VC? HelloFresh is one of the biggest and $2.5BN market cap? What have been the best and worst resource allocations Dominik has made? Do recessions help or hurt recipe box businesses?

Guillaume Cabane is a growth advisor to high-growth SaaS Startups, including Ramp, Spot, Airbyte, G2, Gorgias, Metadata, Madkudu, and others. Guillaume held VP of Growth roles at Drift, Segment, and other successful startups, where he helped them grow from ~50 to 300. Prior, Guillaume spent 6 years at Apple. In Today's Episode with Guillaume Cabane We Discuss: 1. Entry into Growth: How did Guillaume make his way into the world of growth? What are 1-2 of his biggest lessons from him time at Segment where he 4x revenue? What does Guillaume know now that he wishes he had known when he entered growth? 2. Enterprise vs SMB & CAC/LTV: Why does Guillaume think it is harder to go enterprise down than SMB up? What are the biggest mistakes companies make when scaling into enterprise? What are the biggest mistakes startups make with product-led-growth motions? Why does Guillaume believe it is impossible to analyse CAC/LTV in early companies? 3. Activation, Engagement and KPI Setting: What are the biggest mistakes companies and teams make in activation? What can growth and marketing teams do to guarantee engagement in prospects? Why are all KPIs not tied to revenue BS? 4. Hiring the Growth Team: What are the core characteristics of great growth hires? How quickly does it become apparent when you have made a bad growth hire? Why do founders make the best profiles when hiring your first growth hire? What are the biggest mistakes Guillaume has made when hiring for growth? 5. Why Growth is Like Venture: What is the secret to building a great growth portfolio? Why is it impossible to scale to $50M ARR with only one good channel? What is the right way to spread resources across channels? When is the right time to add new channels and diversify?

Keith Rabois is a General Partner @ Founders Fund, one of the world's best venture funds with a portfolio including the likes of Facebook, SpaceX, Anduril, Tesla and many more. For the last 23 years straight, Keith has either invested in or founded a $BN company. Keith is also the Co-Founder and CEO @ Openstore, the company that will buy or run your Shopify business. Mike Shebat is the Founder and CEO @ Traba, the company providing industrial staffing when and where you need it. To date, Mike has raised $49M with Traba from some of the best including Founders Fund, General Catalyst and Khosla Ventures. In Today's Episode We Discuss: 1. What it Takes to Build a Great: Why does Mike expect everyone to work in office 12 hours per day, 4 days per week? At what point does an extra hour of work not lead to more output? What are the expectations in terms of emails, out of office, the weekends? Keith, from the 23 BN companies you have worked with, is this insane work ethic aligned to all of them? Which had it? What did not? What core components of PayPal's work ethic made it so strong? What does Keith mean when he says Linkedin could and should have been 5x bigger? 2. The Hiring Process for the Swat Team: What does the hiring process look like for this type of work environment? What are the signs that someone is really aligned to it vs faking it for the interview process? What have been Keith's biggest lessons on both compensation and title in the hiring process? Why does Keith believe that culture is like concrete? What are the biggest mistakes he has made on culture and what would he have done differently? 3. First-Time Founders, Innate Entrepreneurs & Europe's Failing: Does Keith agree the best founders always show signs of early entrepreneurship in their teens? Why does Keith prefer first-time founders to serial entrepreneurs? Why are they better? Why does Keith believe that Europe has not created a $100BN company since 1990? 4. Remote Work, Network Effects and Baseball: Why does Keith believe being great in venture is like baseball? Why does Keith and Founders Fund not invest in remote teams? How does he explain Gitlab? Why does Keith believe Airbnb has the best network effect he has ever seen?

Des Traynor is a Co-Founder of Intercom, and has built and led many teams within the company, including Product, Marketing, and Customer Support. Yann LeCun is VP & Chief AI Scientist at Meta and Silver Professor at NYU affiliated with the Courant Institute of Mathematical Sciences & the Center for Data Science. He was the founding Director of FAIR and of the NYU Center for Data Science.  Emad Mostaque is the Co-Founder and CEO @ StabilityAI, the parent company of Stable Diffusion. Stability are building the foundation to activate humanity’s potential. Jeff Seibert is the Founder & CEO @ Digits, building the future of AI-powered accounting. Digits have raised funding from the likes of Peter Fenton @ Benchmark and 20VC. Tomasz Tunguz is the Founder and General Partner @ Theory Ventures, just announced last week, Theory is a $230M fund that invests $1-25m in early-stage companies that leverage technology discontinuities into go-to-market advantages. Douwe Kiela is the CEO of Contextual AI, building the contextual language model to power the future of businesses. Cris Valenzuela is the CEO and co-founder of Runway, the company that trains and builds generative AI models for content creation.  Richard Socher is the founder and CEO of You.com. Richard previously served as the Chief Scientist and EVP at Salesforce. Before that, Richard was the CEO/CTO of AI startup MetaMind, acquired by Salesforce in 2016. In Today's Episode We Discuss: Foundational Models: Analysis Will foundational models become commoditized? Who are the major players? What are their different strengths? Who will win? Who will lose? How important is the size of the model vs the quality of the data? 2. Open vs Closed: What are the biggest pros and cons of an open ecosystem for LLMs? Why is it naive to think that open-source LLMs will prevail? What will determine which method wins? 3. An Analysis of the Incumbents: Why is Google the most vulnerable? What can they do to regain ground? Why is Apple the sleeping giant? How could they win the next wave of AI? What should Amazon do today to compete with Microsoft? 4. The Future: Doom and Gloom? Why is it ridiculous to assume AI systems want to dominate? Why will AI create a renaissance of creativity and human freedom? What role should regulation play in the advancement and progression of AI?

Jeff Seibert is the Founder & CEO @ Digits, building the future of AI-powered accounting. Digits have raised funding from the likes of Peter Fenton @ Benchmark and 20VC. Jeff previously served as Twitter's Head of Consumer Product, a position he came to following the acquisition of his prior company, Crashlytics. Today, Crashlytics is the de-facto mobile crash reporting solution for iOS and Android and runs on over 6 Billion monthly active smartphones worldwide. In Today's Episode with Jeff Seibert We Discuss: 1. The Art of the Pivot: What are Jeff's biggest pieces of advice to founders pivoting? How do you know when you have enough data to make the decision to pivot? What are the single biggest mistakes founders make when pivoting? 2. AI: Who Wins and Who Loses: Why does Jeff believe that OpenAI will transition into an infrastructure play? What are the most significant challenges OpenAI will face moving forward? Why does Jeff believe that Apple are best positioned to win in an AI world? Why does Jeff believe that Google are the most vulnerable incumbent? What would Jeff do if he was CEO of Google? 3. LLMs: What Happens Now: Will we see the commoditization of LLMs? What are the biggest misconceptions people have on training and fine-tuning LLMs? Will we see LLMs increasingly specialise to vertical-specific models or will they remain horizontal? What is the difference between a thick and a thin wrapper when building on top of LLMs? 4. Angel Portfolio in Review: How many angel checks has Jeff written? How many failed? How many home runs? Does Jeff believe that company valuations are being kept artificially high? How did Jeff make 200x selling through the secondary market for a now failing company? What are Jeff's three biggest pieces of advice for angels today?

Matteo Franceschetti is the Co-Founder and CEO @ Eight Sleep, a company dedicated to fueling human potential through optimal sleep. To date, Matteo has raised over $160M for the business from the likes of Founders Fund, Ryan Petersen, Naval Ravikant, Kevin Hart, AROD and many more. In Todays Episode with Matteo Franceschetti We Discuss: 1. Why Did Sleep Need "Solving": Why did Matteo decide he wanted to spend decades of his life-solving sleep? If Matteo has known how hard it was going to be, would he do it again? What does Matteo know now that he wishes he had known at the start of the journey? 2. Hiring the Best Team: What is Matteo's playbook for hiring? What are the five questions that Matteo asks in every interview? What are big red flags? What are strong signals of great talent? If people have been let go in a RIFF, is that a concern? How does Matteo construct hiring panels? What vote count is enough for an approved hire? What are Matteo's biggest lessons on title and pay a new hire receives? What are some of Matteo's biggest lessons when it comes to firing people? 3. Funding the Business: What was the hardest round to raise? Why? Are investors justified in their skepticism of hardware? What are the single biggest pieces of advice Matteo would give to founders on raising? How impactful has it been having Keith Rabois and Founders Fund as an investor? Do VCs really add value? 4. Mastering Health, Sleep and Nutrition: How does your diet impact the quality of sleep you have? How does exercise and the time of exercise impact your sleep? What are some common rules on sleep that are BS and myths? What are some of the most non-obvious truths about getting great sleep?

Rebecca Kaden is a Managing Partner @ Union Square Ventures, one of the leading early-stage firms of the last decade with investments in Twitter, Twilio, Coinbase and many more. Nicole Quinn is a General Partner @ Lightspeed where she has led investments or sits on the board of Calm, Cameo and LunchClub to name a few. Eurie Kim is a Managing Partner @ Forerunner Ventures, the leading early-stage consumer fund. Eurie has led investments and sits on the board of Oura, The Farmers Dog, Curology and more. In Today's Roundtable We Discuss: 1. Seed Rounds: Is it even possible for traditional seed funds to play in a world of multi-stage funds investing so aggressively at the seed stage? Is seed immune to the macro environment? Will seed pricing remain as high as ever? What advice does the team have for seed founders approaching a Series A? What do they need? 2. Series A: How is the Series A market looking today? Is there a crunch at the Series A? To what extent are valuations compressed at the Series A? What 3 core elements do companies at the A stage, looking for a Series B next, need to focus on? 3. Series B and Beyond: Is the real crunch at the Series B? Why are down rounds so much better than structured rounds for companies raising? Will we see a wave of M&A in the next 12 months? 4. Crypto, AI and Hot Takes: Why is now the best time to be investing in crypto? Why is investing in AI a lottery right now? What is the most controversial thing that each believes today?

Des Traynor is a Co-Founder of Intercom, and has built and led many teams within the company, including Product, Marketing, and Customer Support. Today Des leads all Intercom’s R&D efforts, and parts of Intercom’s marketing. In Today's Episode with Des We Discuss: 1. From Consultancy to Founding a Unicorn: What was the founding a-ha moment for Des and the team with Intercom? Why does Des believe that most startup advice is BS and outdated in 5 years? What does Des know now that he wishes he had known when he started? 2. LLMs: The World is Not Equal: What does Des mean when he says the world of LLMs is not equal? How do the different LLMs very in quality, price and speciality? Does Des agree with Alex @ Nabla, "the best companies in the future will work with many LLMs at the same time and switch between them for different things"? To what extent does Des believe LLMs will be commoditised and it will be a race to the bottom? Would Des be a buyer of OpenAI at a $90BN price? Why not? 3. How to Survive in a World of OpenAI: What two simple questions will determine if Open AI will kill your existing business? What 3 criteria will determine if there is a new business to be built on top of OpenAI? What is the different between a thin layer on top of an LLM and a thick wrapper with real value? Which traditional incumbents are most vulnerable? What should they do in this new world? How long does it take for incumbents to really be impacted? 4. The Titans of Tech: Who Wins: Why does Des believe that Apple could be a massive winner in the next wave of AI? Why does Des believe that Google have not been impressive and failed to keep pace? Why does Des think OpenAI should be wary of Amazon? What could they do to threaten them? What opportunity does Facebook have here? How could Instagram and Whatsapp win? 5. Startup and Investing 101: Why does Des believe that every founder should write a blog post per week? Why does Des believe that most B2B marketing sucks? What makes great B2B marketing? What are Des' biggest lessons from the Hopin journey? How has Des' angel investing changed in the last year with the rise of AI?

Ryan Petersen is Founder & CEO @ Flexport, a leader in global supply chain technology. In 2022, Flexport moved more than $26 billion of merchandise. Over the last 10 years, Ryan has raised close to $2.5BN for the business with the latest valuation pegging the business at $8BN. Prior to starting Flexport, Ryan was the founder and CEO of ImportGenius, a premier provider of transaction data for the global trade industry. In Today's Episode with Ryan Petersen We Discuss: 1. The Origins of a Generational Defining Leader: What did Ryan want to be when he was growing up? How did scooters and motorbikes in China lead to the idea for Flexport? What does Ryan know now that he wishes he had known when he started Flexport? 2. Speed and Money: The Secrets To Execution: Does Ryan believe speed is key to execution? What is the difference between speed and velocity? What advice does Ryan have to founders who raise a lot of money? How should it impact hiring? What are the most common ways founders become inefficient post-fundraising? Why does Ryan look to invest in founders with jaded pasts and a chip on their shoulder? 3. The Art of Resource Allocation: Are the best CEOs the best resource allocators? What is the single best resource allocation Ryan has made? What did he learn? What is the worst? What did he learn? What have been Ryan's biggest hiring mistakes? How did that change his approach? 4. The Wider World: Is Ryan long or short on China? Why? Will we see global trade become nationalized? Why? Will we see interest rates raised further? What impact does that have on trade? What has been the impact of war on trade and the shipping industry? 5. Ryan Petersen: The Father and Husband: How has having kids changed how Ryan approaches leadership and management? How does Ryan juggle 2 young kids and leading a 2,500 person company? How does Ryan retain romance with his wife while also being a full-on CEO of a large co? Does money make you happy? What does it help with? What does it not help with?

Chris Degnan serves as Snowflake’s Chief Revenue Officer and has been with the company since 2013. Starting as employee #13 and Sales employee #1, Chris built a go-to-market strategy from the ground up, driving sustained high growth and global reach. Under his sales leadership, Snowflake has grown its annual product revenue from $0 to over $1 billion. Prior to Snowflake, Chris served in Sales leadership roles at EMC and Aveksa, and worked in enterprise sales at Informatica and Covalent Technologies (acquired by VMware). In Today's Episode with Chris Degnen We Discuss: 1. From SDR To World Leading CRO: How did Chris first make his way into the world of sales? What does he know now that he wishes he had known when he started in sales? What are the single biggest mistakes young sales people make today scaling their careers? 2. The Secret to Hitting Quota in Sales: Why does Chris believe all reps need to do 8 customer calls per week? How do the best sales reps approach sales prospecting today? Is cold outbound dead? How does Chris advise his teams on cold calls and emails? What are the best reasons reps should say no to customers? Should reps be discounting today? What is an acceptable level? 3. Sales and Product: The Most Important Relationship: Why does Chris believe sales and product is the most important relationship? What can leaders do to ensure sales and product communicate effectively? How does Chris use sales calls today both with his sales team and with product? What are the single biggest reasons comms between sales and product breaks? 4. Mastering Sales Leadership: How does Chris approach sales forecasting? What works? What does not work? Does Chris celebrate when quota is hit? How do you find the balance between pushing further and harder but also celebrating the wins? How do the best sales leaders train and develop their talent? What do the worst do? 5. Customer Success is BS: Professional Services for the Win: Why does Chris believe that customer succeed is BS and you should get rid of it? Why are professional services so much better? How should the org be structured then when removing CS and adding professional services? Who is then responsible for upsell?

Danny Cohen is the President of Access Entertainment, a division of Len Blavatnik's Access Industries. Access Entertainment’s corporate investments include film and television studio A24; Europe’s fastest-growing company Tripledot Studios; creator economy leader Spotter; and a new immersive arts’ experience launched in collaboration with David Hockney and Lightroom. Before joining Access, Danny was the Director of BBC Television where he had responsibility for all of the BBC's network channels and the greenlighting and production of the BBC's drama, entertainment, comedy, arts, history, science, educational content and documentary.  In Today's Episode with Danny Cohen We Discuss: 1. From Leading the BBC to Investing for Len Blavatnik: How did Danny make his way from leading the BBC to investing for Len @ Access? What was he most nervous about when making the transition to investing? What has been the hardest investing skill to learn? 2. Great Founders are Like Great Actors: What are the biggest similarities in what makes the best founders and the best actors? How are the best founders different from the best actors? Why does Danny believe the risk that an actor takes is so different to the risk founders take? How does Danny feel both founders and actors can and should be managed? 3. The Future of Media: What does Danny mean when he says he looks for "eyeballs and attention" when investing? How does legacy media respond to the threat created by social media today? How does AI change the future of content creation and distribution today? How do the strikes in Hollywood impact the future of content supply? 4. Marriage, Children and Loneliness: Why does Danny believe that loneliness will continue to be the biggest problem we face? What are Danny's biggest pieces of advice from 17 years of happy marriage? Why did Danny decide to not have children? What did that decision-making process look like?

Joey Zwillinger is the Co-Founder & CEO @ Allbirds, the company behind the world's most comfortable shoe. In Nov 2021, Joey took the company public and the stock soared to an all-time high of $4BN, today the company has a market cap of $137M. Prior to Allbirds, Joey spent six years at biotechnology firm, Terravia, leading its renewable chemical business, developing and selling high-performance algae-based chemicals into various industries such as CPG, personal care, and industrials. In Today's Episode with Joey Zwillinger We Discuss: The Founding Moment: How did Joey's wife's friendship lead to the co-founding of Allbirds? What does Joey know now that he wishes he had known at the founding moment? What does Joey believe he is running away from? What is he running towards? 2. Public Market Performance Review: Why has Allbirds lost 97% of it's value since going public? What mistakes were made? Why has revenue declined for the first time this year? What strategic investments have Allbirds pulled back on or paused entirely? When will Allbirds be profitable? 3. The Competition: How do Allbirds compete and catch up with On and Hoka? What strategic mistakes did Allbirds make in COVID that allowed others to take the crown? Was the movement into running and athletics a mistake for Allbirds? 4. Joey Zwillinger: The Leader and Person: Did Joey take secondaries out during the Allbirds journey? How does Joey reflect on his own relationship to money? How has Joey dealt with the last 12 months personally? How does he manage the stress effectively?

Jack Altman is the Founder and CEO @ Lattice, the #1 people management platform, last valued at $3BN. Jack is an investor through his founding of Jack Altman Capital where he has invested in WorkOS, NexHealth, Owner.com, Mercury and more. Auren Hoffman is the Founder and CEO @ Safegraph, the most accurate database of global points of interest, last valued at $550M. Auren is an investor through his founding of Flex Capital where he has invested in Chime, Checkr, Coinbase, Flexport, Vercel and more. Jason Lemkin is the Founder and CEO @ SaaStr, the world's largest SaaS community. Jason is an investor through his founding of The SaaStr Fund. In the past, Jason has invested in Pipedrive, Algolia, Salesloft, Front, GreenHouse, Owner.com, Gorgias and more. In Today's Episode on Founder-Led Funds We Discuss: Why have we seen the rise of "Founder-led Funds"? Are founder-led funds more empathetic to the founders they invest in? How do founder-led funds source and pick investments in a way that traditional VC does not? Will we see founder-led Funds truly compete against the Sequoias of the world? How does being an operator make you a better investor? How does investing help you be a better founder and operator? How do you communicate your investing practice and firm to your company and team? What are the biggest excitements and concerns LPs have for Founder-led Funds? Will we see the face of venture changing much more broadly and structurally? How do founder-led funds manage both time and company conflicts?

David Meyer is the SVP Products at Databricks where he drives product strategy and execution. He previously ran Engineering and Product Management at OneLogin, where he grew the company to thousands of customers and market leadership. Before OneLogin, he cofounded UniversityNow, an accredited open university system, running Product and Engineering. Prior to that, David managed a $1 billion portfolio of business intelligence products at SAP and co-led cloud strategy. His first software journey was at Plumtree which went public before being acquired by BEA in 2005. In Today's Episode with David Meyer We Discuss: Entry into Product: How did David make his way into the world of product? Why did he not want to go into it? Why does David advise everyone "do not go into product management"? What does David know now that he wishes he had known when he entered product? 2. How to be a Great Product Leader: Why does David think most leaders suck at leading? Why is the most important thing to make your team feel seen? What can leaders do to ensure this? Why does David help his team members to find other roles outside of the company? 3. Building the Best Product Team: How does David hire for product today? What questions does he ask? What signals does he look for? What are David's biggest hiring mistakes? How did they change his approach? What are the biggest mistakes founders make when hiring for product? Why should you hire people who are not in product today? 4. David Meyer: The Art or Science of Product: Is product more art or science? If David were to put a number on it, what would it be? Is simple always better when it comes to product? Will AI remove the importance and focus on UI? Why are the most impressive companies business model innovations not product innovations?

Nick Tomaino is the Founder and General Partner @ 1confirmation, one of the leading seed firms fueling the decentralization of the web and society. The fund started with $26M in backing from individuals including Peter Thiel and Mark Cuban and it has been reported that the firm now has over $1B in assets under management. Nick has led seed investments in OpenSea, dYdX, SuperRare, Polkadot and Cosmos among others. Prior to 1confirmation, Nick was a Principal @ Runa Capital and before that led business development and marketing at Coinbase in the early days of the company. In Today's Episode with Nick Tomaino We Discuss: From Cryptokitties to founding the Leading Seed Crypto Firm: How did Nick first come into contact with crypto and bitcoin specifically? How did getting fired from Coinbase catalyse his move into venture? What does Nick know today that he wishes he had known when he started investing? 2. The Landscape Today: Funds and SBF Are the current generation of crypto funds too large? Should they give money back to their LPs? Will the next generation of crypto funds be smaller? Are any crypto funds able to raise right now? Why does crypto Twitter hate crypto VCs? Who are the worst VCs for pump and dump? 3. SBF & FTX: What Actually Happened, Who is to Blame, What Happens from here? What is the biggest misconception on SBF and FTX today? Who should be held accountable? What else would Nick like to see? How should FTX change the way that LPs invest into venture managers? 4. How to Build the Best Crypto Portfolio in Venture: How large are the funds? How does Nick determine the right size for a fund? How many investments does Nick make per fund? How do loss rates look in crypto? What have been Nick's biggest investment hits and losses? How did that impact his mindset? 5. The Future for NFTs and Opensea: Why does Nick remain bullish on the future of NFTs? How is Nick able to remain optimistic about the future of Opensea given their volumes? Where does Nick believe the fair price for Opensea should be today? Did Nick sell their Opensea at the $13Bn round?

Ed Sim is one of the best seed round investors in venture as the Founder and Managing Partner @ Boldstart, Ed focuses specifically on developer, infra and SaaS at pre-seed and seed round. Over the last decade, Ed has backed some of the best including Snyk, BigID, Kustomer, Front and Superhuman. In Today's Episode on Seed Rounds We Discuss: The Three Types of Seed Round: What are the three different types of seed round today? Has seed ever been this competitive? Will seed be unimpacted by the macro decline we are seeing? Why are growth and multi-stage funds being more active than ever in seed? 2. Too Much Cash Will Kill You! Why does Ed believe that too much capital can kill companies at the seed round? Why does Ed believe that the best founders are not always optimising for the highest price? What are the single biggest negatives of taking a high price at the seed round? What advice does Ed have for founders who have large offers from multi-stage funds at seed? 3. Is Growth Dead? Why does Ed disagree and suggest that growth is not dead? What do multi-stage and growth funds now what to see that they did not before? How will the growth market evolve over the next 12-18 months? 4. IPOs, AI and M&A: What will cause the IPO windows to crack open again? Why does Ed believe that many investing in AI are simply giving money to Nvidia? Does Ed agree that 95% of the cash going into AI from venture today will go to zero? Will we see more or less M&A in the next 12 months? How did Ed evaluate the Loom acquisition by Atlassian?

Ely Lerner is an EIR at Reforge and an advisor for startups transitioning from traction to hypergrowth. Previously he was Head of Consumer Product at Chime, and before that spent an incredible 8 years at Yelp in a number of different roles including Head of Product at Eat24, and Product Leader/GM at Yelp. In Today's Episode with Ely Lerner We Discuss: 1. Entry into Growth: How did Ely make his way from engineering manager to growth leader? What are a couple of his single biggest takeaways from his time with Yelp and Chime? Why do employees in large companies have to have P&L ownership when innovating within the larger company they are in? 2. Advisors: What, When and How: What are the three different types of advisors founders can work with today? When is the right time to engage with each of them? Should the advisor have had direct experience with the problem you need help with? How should these advisors be compensated; what is normal? What are 1-2 of the biggest reasons startup advisory roles do not work out? 3. Offense vs Defence: The Tricky Balance: What is the difference between offense and defense in product strategy? What should the resource allocation be between the two? What is the right amount of offensive strategies to have on at the same time? How can leaders prevent their defensive teams from feeling like second-class citizens? 4. Ely Lerner: AMA: Why does Ely disagree with many and suggest that horizontal products do have a core ICP? Should growth teams sit on their own or within functions in the org? What are the core reasons teams fail to ship fast? What state should your data be in when you bring in your first growth hire?

Matthieu Rouif is the Co-Founder and CEO @ PhotoRoom, one of the fastest-growing YC companies having scaled to an astonishing $50M in ARR in just 3 years. Their capital efficiency is immense having scaled to $20M in ARR on just $2M of invested capital. Prior to founding PhotoRoom, Matthieu founded several start-ups, including an app for ski resorts, HeyCrowd, and Replay, a video editor which was ultimately acquired by GoPro. Whilst at GoPro, Mattheiu led all image editing products. In Today's Episode with Matthieu Rouif We Discuss: From GoPro to One of YC's Fastest Growing Companies: How did Matthieu make the move from GoPro to founding PhotoRoom? What are the big mistakes Matthieu made on prior companies that he did differently with PhotoRoom? What does Matthieu know now that he wishes he had known when he started PhotoRoom? 2. Scaling to $20M in ARR with $2M of Cash: What allowed Matthieu and PhotoRoom to be so capital-efficient in their scaling? What are the biggest mistakes founders make when it comes to resource allocation and capital efficiency? On reflection, what did Matthieu not spend money on that he wishes they had spent money on? 3. Consumer Subscription + Photo Editing: Is it a Good Business: What are the customer acquisition costs by channel for PhotoRoom? What are their payback periods on a per-customer basis? How can it be a good business when the churn rate annually is 30-40%? How does this space play out with Canva, Adobe, Veed, Kapwing? Who wins? 4. The Future of AI: Who wins; incumbents or startups? What matters more; data size or model size? Will UI be more or less important in an AI-first world? Why does Matthieu believe that everyone hates command line prompts? Will we see $BN revenue companies created with just 10 people?

Harry Stebbings is the Founder of 20VC, building the next great financial institution at the intersection of media and venture capital. 20VC has reached over 125M downloads in 100+ countries and has featured the likes of Doug Leone, Bill Gurley, Marc Benioff, Daniel Ek and more. On the investing side, Harry has raised over $400M and made investments in the likes of Pachama, Linear, TripleDot, Superhuman, AgentSync, Linktree, Sorare and more. In Today's Episode We Cover: Are LPs Open for Business: How has what LPs look for in new manager investments changed? What type of funds will be able to raise? Which will not be able to raise? What can managers do to significantly increase their chances of raising a new fund? 2. The Seed Investing Landscape: Harder Than Ever Why is seed pricing as high as ever? Why are multi-stage funds more active in seed than ever? How does this impact seed? How will seed change and evolve over the next 6-12 months? 3. Series A + B: The Best Place to be Investing Why is Series A the best risk/reward insertion point when investing today? How has the competition level at Series A and B changed? What do many people not see or know about this stage of the market today? 4. Is Growth Dead: Are Growth Deals Getting Done: What two core elements are needed if you want to raise a growth round today? How have growth round valuations been impacted over the last 12 months? To what extent do founders need to change their expectations on the price of rounds they will be able to get done today? 5. M&A and IPOs: Tough Times Ahead Why will we see continued low levels of activity in M&A markets? What acquisitions are we seeing take place? When will the IPO window crack open? Why were Klaviyo, Instacart and Arm not enough to open the windows?

Beezer Clarkson leads Sapphire Partners‘ investments in venture funds domestically and internationally. Beezer has invested in some of the best firms of a generation including USV and Point Nine to name a few. Beezer began her career in financial services over 20 years ago at Morgan Stanley in its global infrastructure group. Prior to joining Sapphire in 2012, Beezer managed the day-to-day operations of the Draper Fisher Jurvetson Global Network, which then had $7 billion under management across 16 venture funds worldwide. In Today's Episode with Beezer Clarkson We Discuss: LP Landscape: WTF is Going On: Are LPs really all closed for business? What has changed in what LPs want to see from managers they are looking to invest in? What has changed about the size and pace of new commitments for LPs? Are all LPs moving away from growth? 2. 2020-2022: Years in Review: Are LPs frustrated by managers who reduced deployment timelines to 12-18 months? Are LPs frustrated with managers who did not take liquidity when they could have done? How does Beezer advise managers on when and how to take liquidity in their best positions? Are managers accurately marking their portfolios to their LPs today? Why does Beezer believe the incentive mechanism for LPs is broken today in many ways? 3. How To Build a Top Decile Firm: Why does Beezer believe if you want to have the best returns, you have to have one company that returns the fund? Can you not do it with multiple half-fund returners? Is ownership core to all the best firm's top performance? Is it the size of outcome or the size of ownership that drives the best performance across the board? What does data show on how the best funds take significant risk? What are their loss ratios? What are the core tradeoffs to Beezer between scaling AUM and providing top decile returns? 4. LP Markets: The Times They are a Changing: Does Beezer believe LPs will remain cold on large $1BN+ growth firms? Which segments of the market are hot? Which are cold? What are the most significant changes we will see in the LP markets moving forward? Is today the new normal or are we in a downturn that we will come out of?  

Matthew Prince is the co-founder and CEO of Cloudflare, on a mission is to help build a better Internet. Matthew has scaled Cloudflare to over $1BN in revenue, $20BN in market cap, and over 3,200 employees. Today the company runs one of the world's largest networks, which spans more than 200 cities in over 100 countries. Matthew is a World Economic Forum Technology Pioneer, a member of the Council on Foreign Relations, winner of the 2011 Tech Fellow Award, and serves on the Board of Advisors for the Center for Information Technology and Privacy Law. In Today's Episode with Matthew Prince We Discuss: 1. From Selling Fireworks to Public Company CEO: How did Matthew first make money selling fireworks as a kid? Does Mathew believe in the trope "you have to love what you do"? What does Matthew know now that he wishes he had known when he started Cloudflare? 2. Money, Identity and Happiness: Why does Matthew feel many of the most successful founders lose their way when they leave their companies? How does he assess Gates, Bezos and others? Does Matthew tie his own identity to Cloudflare and the success of the company? How does Matthew evaluate his own relationship to money today? How has it changed over time? How does Matthew keep score today on how he is doing? What is success to Matthew? 3. The Three Outcomes for Companies Today: What are the three outcomes available to companies today? What is the worst and why? What are the two biggest mistakes Matthew sees founders make today? Why does Matthew know that diverse teams are more successful? What is the proof? What is Matthew's single biggest advice to founders when it comes to selecting a co-founder? 4. Focus is BS: You Have to Have Mega Ambition: Why does Matthew believe it is BS to have a very specific target customer from the offset? What does Matthew believe are the benefits of not having an ICP in the early days? What are the biggest pieces of VC advice to founders that Matthew knows to be wrong?

Michael Eisenberg spent 15 years as a General Partner @ Benchmark working alongside Bill and the Benchmark partnership. Following Benchmark, Michael co-founded Aleph, one of the leading Israeli venture funds of the last decade with a portfolio including Lemonade, Melio and HoneyBook, just to name a couple of Aleph’s unicorns. Adi Levanon is the Founder & Managing Partner @ Selah Ventures, a solo-GP-founded venture fund investing $500k checks into AI-based solutions that enhance financial services, healthcare organizations, fintechs, and SMBs, with a focus on founders in the US and Israelis globally. In Today's Episode on Israeli Resilience We Discuss: Where are we at today? What is it like on the ground, today? Have the international community reacted as expected? What more can be done? What does it mean to be called up for "reserve"? How are companies dealing with 25% of their teams being called into the armed forces? Are VCs investing still? Does work carry on? Whose reactions are exemplary and we should look to follow? Whose have been woeful and should be called out? What are the single biggest misconceptions of the situation? What can people do to help? What can be done?

Deven Parekh is a Managing Director at Insight Partners, one of the leading investing franchises of the last 25 years. Deven has made more than 90 investments since joining in 2000 including in the likes of Twitter, Alibaba, JD.com, Chargebee and Automattic (WordPress) to name a few.   Woody Marshall is a General Partner @ TCV, one of the most successful growth funds of the last decade with a portfolio including the likes of Facebook, AirBnB, Spotify, LinkedIn and many more incredible companies. Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few.  In Today's Episode We Discuss: 1. The Growth Landscape Overview: Is growth dead? Are any growth deals getting done? How has the price changed for growth deals that are getting done? Which type of growth companies will vs will not be able to raise? What happens to all of the growth companies with $300-$500M in cash but little revenue? 2. The Great Reset: Valuations Need to Change: Why should companies be actively resetting their valuations? What are the benefits? What will happen between VCs and LPs when there is no incentive for VCs to reset their portfolio valuations when they need to go out and raise from those same LPs? Structure is often part of these valuation resets, is structure to rounds always bad? When is it good? What type of structure is acceptable vs unacceptable? 3. Are the Public Markets Creeping Open: Should we take comfort from ARM, Instacart and Klaviyo and assume the public markets are going to open again? If not, what will cause them to open? How should we analyze the performance of the IPOs above? Many have been negative, are they right to suggest this is not the response we wanted? Why does Woody believe, like Instacart taking a 75% discount to their last round, we should have more and more companies go public at discounts to their last private round? 4. Late Stage Growth is Dead and Revenue Multiples: Why is late-stage growth dead? How long do we think this will last? How should we assess revenue multiples today? New normal? Same as always? How will revenue multiples look in 12 months from now? How should we analyse the large late stage growth rounds for hyped AI companies? What happens there?

Scott Farquhar is the Co-Founder & Co-CEO @ Atlassian. Scott co-founded the company with his university friend, Mike Cannon-Brookes, in 2002 from Australia. Over an incredible 20-year journey they have grown to a market cap of $50BN today, over 11,000 staff globally and serving over 260,000 customers. Scott is also a co-founder of Skip Capital, a private investment fund with a portfolio including Figma, Snyk, Canva and more. In Today's Episode with Scott Farquhar We Discuss: 1. The 20-Year Journey to $50BN Market Cap: How did Scott first make his way into the world of tech and come to co-found Atlassian? What does Scott know now that he wishes he had known at the beginning? From 20 years with Mike, what is Scott's biggest advice on choosing your co-founder? 2. The Fundraising Masterclass with Atlassian: An emergency phone call, a honeymoon cut short; how did the first funding round for Atlassian come to be? Where was the business revenue-wise at the time? Why did Scott not like the traditional fundraising process? What did he do to add game theory and ensure that they got the best deal as a company? Why did Scott choose Accel with their offer? How did Peter Fenton lose a $3BN deal with Atlassian? 3. Lessons Scaling Atlassian to $4BN in Revenue: What does Scott believe are the 4 core roles of the CEO? Is resource allocation the most important? What are the single biggest acts of commission and omission that Scott regrets? What are the biggest lessons Scott has from shutting down Stride, their Slack competitor? 4. Scott: The Father, Husband and Philanthropist: What does great fatherhood mean to Scott today? What is the secret to a truly successful marriage? How does Scott assess his relationship to money today? How has it changed with time? How does Scott think about bringing children up in a world of affluence and abundance? Fun Fact: Every single 20VC episode is recorded with Riverside.FM. It is the one product that I could not live without. Try it today here (https://creators.riverside.fm/20VC) and use the code 20VC for 15% off.

Guillermo Rauch is the Founder and CEO @ Vercel, giving developers the frameworks, workflows, and infrastructure to build a faster, more personalized Web. To date, Guillermo has raised $312M from Accel, Bedrock, Greenoaks, GV and more. Prior to founding Vercel, Guillermo co-founded LearnBoost and Cloudup where he served the company as CTO through its acquisition by Automattic in 2013. In Today's Episode with Guillermo Rauch We Discuss: 1. From Argentina to SF: The Boy Making Money Online: How did Guillermo first get into computers and start making money online? Does Guillermo still believe the US and SF offers the same opportunities it did when he came? Did Guillermo feel the weight of responsibility of providing for his family at a young age? 2. Timing, Markets and Narrative Violations: Why does Guillermo believe it does not matter being first but being right? Why does Guillermo believe the most important thing for a company is market selection? Why does Guillermo believe it is crucial that founders and companies have "narrative violations"? 3. The Future of AI: What model will win in the future; open or closed? Where does the value accrue; startups or incumbents? How will the SaaS business model change in a world of AI? 4. Silicon Valley's Most Successful Angel You Did Not Know: What are some of Guillermo's biggest lessons from angel investing? What is his single biggest miss? How has it changed how he thinks? What have been his biggest hits? How did they impact how he thinks about what it takes to win?

Matt Rosenberg is Grammarly’s Chief Revenue Officer and Head of Grammarly Business. He leads all B2B revenue, operations, and growth for Grammarly Business, Grammarly for Education, and Grammarly for Developers. Previously, as CRO of Compass, he took the company into the Fortune 500 and contributed to a more than eightfold increase in business growth. Prior to Compass, Matt served as Eventbrite’s CRO leading them to become the largest event platform in the world by event count. In Today's Episode with Matt Rosenberg We Discuss: 1. From Miserable Lawyer to World Beating Sales Leader: How did Matt make the transition from lawyer to sales leader? What does Matt know now that he wishes he had known when he started in sales? What are Matt's biggest pieces of advice for anyone who wants to make a career change and is lacking confidence? 2. The Playbook and Hiring The Team: How does Matt define the "sales playbook"? Should the founder be the one to create and execute V1 of the playbook? Should the first sales hire be a rep or a sales leader? When is the right time to make that all-important first sales hire? 3. Discounting, Champions and Urgency: What can sales team do to create urgency in deal cycles? What works? What does not? How does Matt approach discounting? When to do it vs when not to? What level is acceptable? What are the biggest secrets to creating champions within prospects? Why does Matt believe that deals are won and lost in prospecting? 4. Developing Great Sales Talent: How does Matt use sales call recordings to train teams? What is his 3x3 matrix for coaching calls? What is a good reason to lose a deal vs a bad reason? How does Matt do deal reviews? What are the single biggest elements sales leaders can do to nurture sales talent? What are the biggest mistakes sales leaders make when developing talent internally?

Phin Barnes is the Co-founder and Managing Partner of The General Partnership (TheGP), a venture capital firm that’s redefining what partnership means for founders. Previously, Phin spent over a decade at First Round Capital, where he was responsible for over 60 investments including Blue Apron, Notion, Clover Health, Gauntlet and Persona. Before First Round, he created an independent video game company and before that was an early employee at AND 1 Basketball where he helped scale the brand from $15 to $225 million in revenue and served as the Creative Director for Footwear. In Today's Episode with Phin Barnes We Discuss: From Creative Director to Venture Capitalist: How did Phin make his way into the world of venture having been a Creative Director at a basketball brand? What does Phin know now that he wishes he could tell himself on his first day in venture? What are 1-2 of Phin's biggest lessons from his 10 years at First Round which shapes how he invests? 2. The Venture Capital Model is Broken: Why does Phin believe the current services model of venture is broken? Do the best founders need your help? What have been some of the biggest lessons in what the best founders want from their VCs? What happens to this generation of firms with massive support teams? Do VCs use these support teams merely to justify massive fund size scaling to LPs? 3. The Venture Landscape Today: How can we compete in a seed landscape of $5M on $25M against large multi-stage firms? What founders types are attracted to big brands? What founder profiles are taken in by large rounds and high prices? Is Phin more or less excited about seed-stage investing now than he has been before? 4. Investing Lessons 101: What is Phin's biggest hit? How did seeing their success impact his mindset? What is Phin's biggest loss? How did the loss impact how he views investing? Traction, team, market; how does Phin rank the three in prioritisation? What should all young people know when entering the venture landscape?  

Kevin Niparko is the VP of Product @ Twilio. Kevin joined Twilio through the acquisition of Segment where he spent an incredible 8 years in numerous different roles including as Head of Product. Before entering the world of product, Kevin was a Management Associate at the world-renowned, Bridgewater Associates. In Today's Episode with Kevin Niparko We Discuss: 1. From Bridgewater to Head of Product: How Kevin made his way from the world of asset management and analytics to leading product teams? What are 1-2 of Kevin's biggest takeaways from his time at Bridgewater with Ray Dalio? How did the 8 year journey with Segment leading to their $3BN acquisition impact his approach to product? 2. What Makes a Great Product Person: Does Kevin believe that product is more art or science? If he were to put a number on it? What would it be out of 100? Why does Kevin believe that all product people should learn to write? Why does Kevin believe that the best product people are generalists and not specialists? Why does Kevin think that analytics is an insanely good start for product people? 3. How to Hire the Best Product People: How does Kevin approach the hiring process for product hires today? What are the non-obvious traits of hires he looks for? How does he test for them? Does Kevin use case studies? Where do many fall down? What do the best do? 4. Product Reviews: Good vs Great: How often does Kevin do product reviews? Who is invited? How have product reviews changed in a world where the company is now fully remote? What is the difference between good and great product reviews? What is the single best product decision Kevin has made? What did he learn? What is the worst product decision Kevin made? How did that change his approach?

Christian Lanng is the Founder and Former CEO @ Tradeshift, a company he took from garage to unicorn raising over $900M for with a latest price of $2.7BN in 2021. Just last month, Christian stepped away from the company and is now Chairman @ Beyond Work, building a better work experience through AI native software. In Today's Episode with Christian Lanng We Discuss: 1. Burnout: When it Hits: How did Christian know when something was really seriously wrong? What were the signs? How did being a founder literally almost kill Christian? How was that not a wakeup moment? How does being a founder make you so out of touch with reality? 2. The Things We Are Never Told: Why does Christian think one of the biggest crimes is the myth that everyone can be a founder? What are the single biggest things about VCs that founders are not told? Why does Christian believe fundraising is absolutely a game? What are the rules to win it? What makes the best VCs? What makes the worst VCs? Why does Christian not like to take a discount for a brand name VC? 3. The Chaos That Happens Inside a Company: Why does Christian believe politics should not be discussed within companies? What are Christian's biggest lessons on working with friends? Why after 14 years does Christian only have 3 friends that still talk to him? How did Christian fire 50% of his leadership team and productivity not change at all? Why does Christian believe US startups are inherently better than European ones? 4. Parenting and Relationship to Money: Does Christian regret not being a present father for his child when building Tradeshift? What are the two options as a founder you have when bringing up kids? Was Christian scared to leave Tradeshift? How does he reflect on his relationship to money? 5. AI: Co-Pilot is BS, The Future Business Model and more... Why does Christian believe co-pilot is the last dying breathe attempt from incumbents? Why does Christian believe that per-seat pricing will die? What will replace it? Why does Christian believe that AI will negate the importance of consumer-facing brands? In what way does Christian believe that UI is total BS? How does it change over time?

Marc Benioff is Chair, Chief Executive Officer and Co-Founder of Salesforce and a pioneer of cloud computing. Under Benioff's leadership, Salesforce is the #1 provider of CRM software globally and one of the world's fastest-growing enterprise software companies. Benioff founded Salesforce in 1999, and it is now a Fortune 150 company with 70,000+ employees. Benioff is the owner and co-chair of TIME, and the founder of TIME Ventures. Benioff is the author of the New York Times bestseller Trailblazer: The Power of Business as the Greatest Platform for Change. Benioff was named “Innovator of the Decade” by Forbes and is recognized as one of the World’s 25 Greatest Leaders by Fortune. In Today's Episode with Marc Benioff We Discuss: 1. The Future of San Francisco: What would Marc do if he were in charge of San Francisco today? What would he change with regards to housing, policing and crime? Why does Marc believe there are doomsday proclaimers on SF? What do they have to gain? Will Dreamforce always be held in San Francisco? 2. Money and Ambition: The Mind Behind a $200BN Machine Does Marc believe that money makes you happy? How has Marc's relationship to money changed over time? How does Marc think about bringing children up in a more affluent home? What does Marc advise anyone who is seeking "happiness" today? 3. Mastering Decisions and Prioritisation: How does Marc assess his own decision-making framework today? Has it changed with time? What is Marc's 5 step process to understand your own priorities today? What does Marc believe are the three biggest priorities for Salesforce today? What are the single biggest blockers that would prevent Salesforce from achieving their goals? 4. Marc Benioff: AMA: What does great fatherhood mean to Marc? Who would win the cage fight, Zuck or Elon? What does a day in the life of Marc Benioff look like? What does Marc think about work from home?

Christian Kleinerman is the SVP of Product @ Snowflake. Before Snowflake, Christian spent close to 5 years at Google as a Senior Director of Product Management @ YouTube working on their infrastructure and data systems. Before YouTube, Christian spent over 13 years at Microsoft serving as General Manager of the Data Warehousing product unit where he was responsible for a broad portfolio of products. In Today's Episode with Christian Kleinerman We Discuss: 1. Lessons from the Greats: How did Christian first make his way into the world of product? What are 1-2 of his biggest lessons from working with Satya Nadella and Frank Slootman? What are 1-2 of hs biggest product lessons from Google and Microsoft? 2. Generative AI: Real vs Fake: How does Christian analyze the current generative AI landscape? Which segments will be the fastest to adopt? Which will be the slowest? What aspects of the ecosystems are overblown? Which are under-appreciated? How does Christian respond to many VCs who suggest that many startups are simply wrappers on GPT? 3. Models 101: Why Size is Not Everything! What matters more, the size of the data or the size of the model? Will any of the models used today be used in a year? Does Christian believe Alex @ Nabla is right in saying that "the most successful companies will be those that are able to transition between models the easiest"? How are we seeing the evolution of model size impact the accuracy of result snad size of data required? 4. Incumbent vs startup & Open vs Closed: Who is best positioned to win; startups or incumbents? What are the nuances; which spaces are best served for startups to win vs incumbents? Will open or closed source be the dominant mode? What are the single biggest challenges preventing open from being successful?

Eric Paley is the Managing Partner at Founder Collective, one of the world’s most successful seed funds with investments in the likes of Uber, The Trade Desk, Coupang and Airtable. Mike Maples is one of the OGs of seed investing. As the Co-Founder of Floodgate, he has backed the likes of Twitch, Okta, Lyft, Twitter and more. Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds with a portfolio including Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few. In Today's Episode on Is the Venture Model Broken? : Is the classic seed model dead? Can seed funds play in a world of $25M valuations? Why is having a firm grasp of the present the best thing an early-stage investor can have? Why does Mike Maples believe no company with true product-market-fit has ever failed? Why does Eric Paley believe "go faster" is the worst startup advice? Why does Mike Maples believe there is a direct relationship between price and risk? Why does Mike Maples believe that outliers by their very nature are lower priced? Why does Eric Paley not focus on ownership? Why can it be dangerous? What are the biggest risks for founders raising at valuations that are too high? Why does Eric Paley believe we will have the biggest chasm between TVPI and DPI in the prior vintage of venture capital returns? Why does Eric believe the majority of SPACs were BS and great companies can always go public? Why does Jason believe that if multiples do not reflate, the venture model is broken? Why does Jason believe we will see the biggest hiring spree in tech next year? How has illiquidity allowed Eric Paley to make some of the best investment decisions? What is Mike Maples biggest lesson from selling Twitter stock early at $1BN?

Miles Grimshaw is a General Partner @ Benchmark, widely considered one of the best venture capital firms in history. Prior to joining the Benchmark Partnership, Miles was a General Partner @ Thrive Capital where he led investments in Airtable, Monzo, Lattice, Github, Segment, Slack and Benchling to name a few. In Today's Episode with Miles Grimshaw We Discuss: 1. Straight into VC From University: From Yale to Thrive How did Miles come to land a role with Josh Kushner and Thrive right out of Yale? What are 1-2 of his biggest lessons from working with Josh @ Thrive for 8 years? What does Miles know now that he wishes he had known when he started in venture? 2. The Pillars of Venture Capital: Sourcing, Selecting, Servicing: What does Miles believe are the 5 core pillars of successful venture capital? 1-5, what is his strongest and what is his weakest? Does Miles really believe that VCs add value today? What are the most clear ways that Miles have seen VCs destroy value in portfolio companies? 3. Investment Decision Making: From Github to Segment: What is the single most important question that Miles has to answer to say yes to an investment? How does Miles think about both market sizing risk and market timing risk? What have been Miles' biggest hits? What did he learn from making those investments? What have been Miles' biggest misses? What did he learn from missing Figma and Plaid? What have been 1-2 of Miles's biggest lessons so far from working with Bill Gurley and Peter Fenton? 4. AI: What Happens Next: Does Miles believe we are in an AI bubble today? How does he assess the landscape? Why does Miles believe that the "Co-Pilot" strategy is an incumbent strategy? Where does Miles believe the value will accrue; the application layer or the infrastructure layer? What does Miles mean when he says the future is in "selling the work and not the software"? What business model disruption and adoption disruption does Miles believe AI will enable? Why does Miles believe that the analogy of AI to the rise of mobile is wrong?

Richard Socher is the founder and CEO of You.com. Richard previously served as the Chief Scientist and EVP at Salesforce. Douwe Kiela is the CEO of Contextual AI, building the contextual language model to power the future of businesses. Previously, he was the Head of Research at Hugging Face, and before that a Research Scientist at Facebook AI Research. Alex Lebrun is the Co-Founder and CEO of Nabla, an AI assistant for doctors. Prior to Nabla, he led engineering at Facebook AI Research. Alex founded Wit.ai, acquired by Facebook in 2015.  Tomasz Tunguz is the Founder and General Partner @ Theory Ventures, just announced last week, Theory is a $230M fund that invests $1-25m in early-stage companies that leverage technology discontinuities into go-to-market advantages. Sarah Guo is the Founding Partner @ Conviction Capital, a $100M first fund purpose-built to serve “Software 3.0” companies. Prior to founding Conviction, Sarah was a General Partner at Greylock where she made investments in the likes of Figma, Coda and Neeva. Emad Mostaque is the Co-Founder and CEO @ StabilityAI, the parent company of Stable Diffusion. Stability are building the foundation to activate humanity’s potential. To date, Emad has raised over $110M with Stability with the latest round reportedly pricing the company at $4BN.  Clem Delangue is the Co-Founder and CEO @ Hugging Face, the AI community building the future. To date, Clem has raised over $160M from the likes of Sequoia, Coatue, Addition and Lux Capital to name a few. Cris Valenzuela is the CEO and co-founder of Runway, the company that trains and builds generative AI models for content creation. To date, Cris has raised over $285M for the company from the likes of Lux Capital, Felicis, Coatue, Amplify, and Nvidia to name a few. Noam Shazeer is the co-founder and CEO of Character.AI. A renowned computer scientist and researcher, Shazeer is one of the foremost experts in artificial intelligence (AI) and natural language processing (NLP).  The Two Most Pressing Questions in AI: What matters more the size of the model or the size of the data? Where does the value accrue in the next 5-10 years; to startups or to incumbents?

Suchit Dash is the VP of Core Product Experience at Reddit, responsible for the surfaces that millions of users interact with daily. Prior to Reddit, Suchit was a cofounder at Dubsmash, a short video platform that was used by millions globally and acquired by Reddit in December 2020. In just 10 days, Suchit scaled the product to an immense 43M users, and gained fans such as Neymar and Jimmy Fallon. Suchit previously held roles at Soundcloud and PayPal. In Today's Episode with Suchit Dash We Discuss: 1. The Founding of Dubsmash & V1: How did the founding of Dubsmash come to be? Suchit scaled V1 of the product to 43M users in 10 days, what was the secret? What worked? What were the first signs that all was not right? How did the team respond to the realization that their retention numbers were terrible? What are Suchit's biggest lessons and pieces of advice from this massive V1 and launch? 2. Data: Retention, Cohorts and The Smiley Face: What specific data did Suchit and the team really use to understand their level of product market fit? What level of retention were they looking for? What is average, good, and great in terms of retention in consumer social? What is really important for founders to try and observe and analyze in net new user cohorts? When and why did the team start to see the hailed smiley face of consumer returning to the app? 3. Battling TikTok: Despite the resurgence, TikTok was roaring, what did TikTok do so well to take the market? How did TikTok leverage both FB and Snap's ad platform to acquire so many users so fast? What did TikTok not do well? What could they have done better? How did TikTok pay and incentivize the creator community? What are some of Suchit's biggest lessons and advice for founders battling a better-funded incumbent? 4. The Decision to Sell: Being Acquired by Reddit: Ultimately, why did Suchit decide to sell the company to Reddit? Why did the first two acquisition attempts fail? What are 1-2 of the biggest pieces of advice Suchit has for founders debating whether it is right to sell their company? What do all founders being acquired need to remember? With the benefit of hindsight, if Suchit could do the acquisition process again, what would he do differently?  

David Velez is the Founder and CEO of Nubank, one of the largest and fastest-growing financial institutions in the world. 1 in 2 people in Brazil alone have a Nubank account. Nubank's purple credit card in Mexico is the highest-rated NPS product of any consumer product in the world. Before founding Nubank in 2013, David was a partner at Sequoia Capital between 2011 and 2013, in charge of the firm’s Latin American investments group. Before Sequoia, David worked in investment banking and growth equity at Goldman Sachs, Morgan Stanley and General Atlantic. In Today's Episode with David Velez We Discuss: 1. From Sequoia Partner to Creating One of the Largest Financial Institutions: What was the Sequoia interview process like? What questions did Doug Leone really dive into when hiring David? What impressed David most about how Sequoia interview and win talent? What are 1-2 of David's biggest lessons from working with Doug Leone? 2. From a Small House to a $BN Public Company: What does David believe are the 1-2 core but non-obvious reasons why Nubank scaled so fast? What does David believe are the most non-obvious but massive opportunities Nubank has to 10x from here? Why does David believe emerging market fintech providers will be more valuable than Western fintechs? What does David believe Western fintechs and regulators can learn from BRIC economy fintechs? 3. How AI Changes The Future of Financial Services: How does David believe AI will change financial services? What products are the lowest-hanging fruit? Which products will be harder for AI to serve? How will AI handle the ambiguity of which master to serve; the consumer and their experience or the bank and their fees and profit motive? Will banks need to own and operate their own models? If using other models, what will differentiate them when they are layers on top of someone else's technology? 4. David Velez: The Leader and Father: What does it mean to be a great listener? How does David approach it? What has been David's biggest lessons from Sequoia on culture? What works? What does not? What are David's biggest pieces of advice to raise kids that are not spoiled and are hard-working and humble? How does David think about "efficient giving" with the philanthropy he does today? What is the big paradox and challenge in philanthropy today?

Doug Adamic is the CRO @ Brex and leads the company's revenue and growth strategy. Prior to Brex, Doug was most recently the Chief Revenue Officer at SAP Concur, a provider of travel spend management solutions and services. During his 16-year tenure oversaw an organization of 600+ employees. He was responsible for all aspects of revenue, generating go-to-market strategies and departments. Prior to SAP Concur, he had a five-year tenure as an Enterprise Sales Manager for Kronos, Inc. In Today's Episode with Doug Adamic We Discuss: 1. Entry into Sales: Does Doug believe that love of sales is innate or can be learned? When did he discover his love? What does Doug know now about sales he wish he had known when he started? What are 1-2 of his biggest takeaways from leading 600+ people at SAP? 2. Discovery, Pipeline and Qualification: What are the three core reasons why companies buy software today? How do the best sales teams use those needs to get deals done fast? What does great sales discovery mean today? Why do you have to make customers feel uncomfortable to understand their true needs? What are the biggest mistakes sales teams make when asking questions, determining customer pain, willingness to pay etc etc? Why does Doug believe that everyone in the company is responsible for demand creation? What are the core pillars to success in qualification? Where do so many go wrong? 3. Getting Deals Done: Why does Doug disagree that now is the hardest time to be selling? Are companies buying new software today? What is the secret to opening up organizations that say they are not open for buying new software? How can sales teams create multiple champions in a prospect? How can they determine who is really a buyer vs who is an influencer in a prospect? What are the biggest tactics that can be used to reduce sales cycles and create urgency in a sales process? 4. Discounting, Trust and Deal Reviews: What is a good reason to lose a deal? What is a bad reason to lose a deal? How does Doug and Brex conduct deal reviews? What makes a good vs a bad deal review? What is the fastest way to lose trust either with prospects or with customers? Why does Doug believe discounting is BS and should not be used?

Nikhil Basu Trivedi is Co-Founder & General Partner at Footwork, an early-stage focused venture firm investing its first fund. In his venture career, he has invested in the early rounds of several companies that have exited or are currently valued at over $1B, including Athelas, Canva, ClassDojo, Color Health, Frame.io, Imperfect Foods, Lattice, and The Farmer's Dog. Prior to Footwork, Nikhil was a Managing Director at Shasta Ventures, on the investment team at Insight Partners, and on the founding team at Artsy. In Today's Episode with Nikhil Basu Trivedi We Discuss: 1. From Summer Intern to Founding a Firm: The 13 Year Journey: How did Nikhil first make his way into venture as an intern at Insight Partners in NYC? What does Nikhil know now that he wishes he had known on his first day in venture? Why does Nikhil advise all young VCs to "not look at their business card"? Why does title not matter in venture? Should founders meet with Juniors as well as GPs and more senior people? 2. Small Funds Outperform Large Funds: Why does Nikhil believe that small funds outperform large funds? Why is AUM the biggest bullshit metric in VC? How does Nikhil advise seed stage founders who have offers from seed firms for smaller rounds at lower valuations and are weighing them against larger rounds with higher valuations from multi-stage funds? Does Nikhil believe that platform value-added services really provide any value? 3. The Art of Investing: What has been Nikhil's biggest investing win? How has it changed his approach to investing? How does Nikhil prioritize between people, traction, and market? What is most important? What has been Nikhil's biggest investing miss? How has that changed his approach? Does Nikhil believe the great founders are immediately obvious? Why is market size the single question that keeps Nikhil up the most? 4. The Dysfunctions of Venture Capital: What are the single biggest areas of misalignment between GP and LP? What do many GPs see and know well that LPs should know and see more of? What are the biggest ways that decision-making breaks down in a venture fund? Why does Nikhil believe that so much of the investment in AI is going to go up in flames?

Mudassir Sheikha is the CEO and Co-Founder of Careem. Over the last 11 years, Mudassir has scaled the service to more than 80 cities in 10 countries, with 1,400+ colleagues and more than 2.5 million Captains. With such success, in 2020 Uber announced they would be acquiring Careem for a reported $3.1BN. Prior to Careem, Mudassir co-founded “DeviceAnywhere”, a company that was acquired by “Keynote” in 2008 before joining the management consulting firm “McKinsey & Company” in Dubai. In Today's Episode with Mudassir Sheikha We Discuss: 1. From McKinsey to $3.1BN Exit to Uber: What was the founding a-ha moment for Mudassir with Careem? What does Mudassir know now that he wishes he had known at the beginning? What does Mudassir believe he is running away from? 2. Finding Product-Market Fit: What is the single biggest mistake founders make when trying to find product-market fit? Does Mudassir believe you have to do things that do not scale, to scale? What did Careem do? What are some of Mudassir's biggest pieces of advice to founders on finding a core target audience and doing customer discovery the right way? 3. Competing with Giants: How To Win When You Cannot Outspend: How did Careem beat Uber when they had 1/100th of their budget? What advice does Mudassir have for founders who have competition that is much better funded? What is the story of spending the night in bunk beds and barely sleeping before raising $300M the next day? How did that happen? 4. The Acquisition: How it Went Down: How did Mudassir and Dara @ Uber first come to meet? How did Dara's approach contrast with the prior approach of Travis Kalanick? Why did Mudassir decide to sell and join Uber? What were the main reasons or arguments against the acquisition? 5. Talk to me About: Careem's Pakistan MD having to flee Pakistan for his safety post a marketing campaign? Elon Musk likes one of Careem's promotional videos and why? An investor who wired $1M with absolutely no paperwork? The catch up meeting that turned into a $3BN offer?

Noam Shazeer is the co-founder and CEO of Character.AI, a full-stack AI computing platform that gives people access to their own flexible superintelligence. A renowned computer scientist and researcher, Shazeer is one of the foremost experts in artificial intelligence (AI) and natural language processing (NLP). He is a key author for the Transformer, a revolutionary deep learning model enabling language understanding, machine translation, and text generation that has become the foundation of many NLP models. A former member of the Google Brain team, Shazeer led the development of spelling corrector capabilities within Gmail, the algorithm at the heart of AdSense.   In Today's Episode with Noam Shazeer We Discuss: 1. Entry into the World of AI and NLP: How did Noam first make his way into the world of AI and come to work on spell corrector with Google? What are 1-2 of his biggest takeaways from spending 20 years at Google? What does Noam know now that he wishes he had known when he started Character? 2. Model Size or Data Size: What is more important, the size of the data or the size of the model? Does Noam agree that "we will not use models in a year that we have today?" What is the lifespan of a model? Does Noam agree that the companies that win are those that are able to switch between models with the most ease? With the majority of data being able to be downloaded from the internet, is there real value in data anymore? 3. The Biggest Barriers: What is the single biggest barrier to Character today? What are the most challenging elements of model training? Why did they need to spend $2M to train an early model? What are the most difficult elements of releasing a horizontal product with so many different use cases? Where does the value accrue in the race for AI dominance; startups or incumbents? 4. AI's Role on Society: Why does Noam believe that AI can create greater not worse human connections? Why is Noam not concerned by the speed of adoption of AI tools? What does Noam know about AI's impact on society that the world does not see?

Cris Valenzuela is the CEO and co-founder of Runway, the company that trains and builds generative AI models for content creation. To date, Cris has raised over $285M for the company from the likes of Lux Capital, Felicis, Coatue, Amplify, and Nvidia to name a few. Runway’s customers include academy-nominated movies, TV shows, media companies, and creatives across industries. In Today's Episode with Cris Valenzuela We Discuss: 1. From Childhood in Chile to Founding one of the Hottest AI Startups: What was the founding moment for Cris with Runway? His investors described Cris as an "outsider". Does Cris believe he is an outsider? What are the biggest pros and cons of being an outsider? What does Cris believe he is running from? What is he running towards? 2. Models are not a Moat: Models 101: What does Cris believe is more important; model size or data size? Why does Cris believe that models are not a moat? How does Cris think about the lifespan of models? Will any used today be used in a year? Are hallucinations a feature or a bug? What are the nuances? 3. The World Has Got AI Wrong: We Need Different Stories: Why does Cris believe the world has got AI wrong? Why do we need different stories for what AI can do and will be? Who should tell them? Why do groups like screenwriters riot and protest if the tool is empowering and not replacing? 4. Company Building 101: Hiring and Fundraising: What are the biggest pieces of startup advice that are total BS? What has been the single biggest lesson Cris has learned when it comes to fundraising? Does Cris believe that VCs really add value? What have been the single biggest hiring mistakes that Cris has made? How has Cris structured their interview process to make it the best interview process in the world?

Howie Liu is the Founder and CEO @ Airtable, the fastest way to build apps for your business. To date, Howie has raised over $1BN with Airtable with the last round valuing the company at $11BN and an investor base including Benchmark, Thrive, Caffeinated, Greenoaks and Coatue to name a few. In Todays Episode with Howie Liu We Discuss: 1. Scaling into Enterprise: What are the single biggest challenges when moving from PLG to enterprise? Why does Howie believe you have only truly hit enterprise when you sign $1M contracts? How long did it take for Airtable to sign their first $1M ARR contract? How can founders know when is the right time to scale into enterprise? How does the product need to change with the scaling? 2. Enterprises: Do They Really Love AI: Why does Howie believe that enterprises are not jumping on AI yet? When does enterprise interest turn into enterprise buying and purchasing? What are the single biggest barriers to enterprises buying AI solutions today? Post-purchase, what are the biggest implementation challenges for enterprises with AI? 3. The Changing Sales Process: Are we seeing the bundling of tools within large enterprises today? Which categories and vendors are most vulnerable? Which will survive the cuts? What do vendors need to do to prove to CFOs that they need to remain in their budget? How has the customer success process changed over the last year with tightening budgets? 4. Howie Liu: AMA: Airtable famously got Benchmark to lead their Series C, how did this come to be when they famously always only do Series A? Why does Howie believe that it is total BS to suggest post-PMF, everything is good? What does Howie know now that he wishes he had known when he started Airtable?

Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few. Prior to SaaStr, Jason was an entrepreneur, selling EchoSign to Adobe for $100M where it is now a $250M ARR product. Rick Zullo is the Co-Founder and General Partner at Equal Ventures. Prior to co-founding Equal Ventures, Rick was an investor at Lightbank, Prior to Lightbank, Rick worked with investment firms Foundation Capital, Bowery Capital, and Lightview Capital. In Today's Episode We Discuss: 1. Why Venture Capital Needs It's Jerry Maguire Moment: Why does Rick believe that VC needs it's "Jerry Maguire" moment? What needs to change? What needs to stay the same? Why does Jason believe we will see even more mega funds in 2024 and 2025? 2. Unicorns are So 2019: Why does Jason believe that "unicorn investing is mostly dead for bigger funds and none of them are looking for a $1BN outcome anymore?" Why does Rick believe that multi-stage fund investing at seed simply does not make sense? What does Rick believe many founders need to know when they take multi-stage money at seed? Of the over 1,000 unicorns created over the last few years, how many of them do Rick and Jason feel are actually unicorns today? 3. Efficiency and Growth: We Need it All: Why does Jason believe, as a founder you should be embarrassed if you ever had a RIF (reduction in force)? Last year many founders got a pass on growth as they were more efficient. Is that pass over? Do they need to get back to growth? What is the single biggest reason that companies do not scale from seed to Series A? What happens to the many companies with years of runway but no product-market-fit? Are we entering a new age of efficient company building or will we go back to high burn environments and excessive spending? 4. Entering the World of LPs: If Jason and Rick were to advise LPs today on how much to discount the value of their venture books, what advice would they give? How have markups completely corrupted the venture ecosystem? How does LPs being incentivized by paper-marks make the industry even more screwed? What are the single biggest misalignments between GP and LP?

Nick Huber is a serial entrepreneur, investor, and content creator focused on real estate and small business. In the last 9 months, Nick has co-founded 6 companies including RE Cost Set, RecruitJet, Titan Risk, Blue Key Capital, Tax Credit Hunter, and WebRun Labs. His primary business, Bolt Storage, owns 1.8M sqft of self-storage facilities across 62 locations in 11 states.  In Todays Episode with Nick Huber We Discuss: Wealth: What the richest families in the world all understand and what the majority of people forget? What are the two best ways to make money as an employee? What do most forget/not do? Why money does make you happy and why society drastically undervalues wealth today? Why we should not be concerned by the levels of income inequality? Marriage and Parenting: 5. Why it is BS to not pass your wealth down to your children? 6. Why you have to let your kids suffer in order for them to grow? 7. How do you stop kids from becoming assholes if they are brought up with money? 8. Why the majority of the time, people choose the wrong partner? What should we look for? 9. What is the number one thing you can do to set your child up for success? Silicon Valley and Entrepreneurship: 10. Why entrepreneurship is not for everyone? Who is it for? 11. Why VCs are out of touch and naive? 12. What is the single biggest lie of Silicon Valley? 13. Why will so many would-be great entrepreneurs burn themselves out when they should not have to? Management and Brand Building: 14. How to build a brand today? Why you have to be controversial to be interesting? 15. How to deal with hate and criticism? Why you cannot please everybody? 16. Why woke culture can give you an advantage if you do not have it? 17. How to build a strategic network the right way? How to become a card in someone's rolodex? 18. What is the single worst thing you can do when hiring? 19. What do you do when you lose trust in an employee?  

Richard Socher is the founder and CEO of You.com. Richard previously served as the Chief Scientist and EVP at Salesforce. Before that, Richard was the CEO/CTO of AI startup MetaMind, acquired by Salesforce in 2016. He is widely recognized as having brought neural networks into the field of natural language processing, inventing the most widely used word vectors, contextual vectors and prompt engineering. He has over 150,000 citations and served as an adjunct professor in the computer science department at Stanford. In Today's Episode with Richard Socher We Discuss: 1. The Decade-Long Journey to Becoming an AI OG: How did Richard first make his way into the world of AI over a decade ago? What are 1-2 of his biggest lessons from working with Marc Benioff? How did 5 years at Salesforce impact how he both thinks and operates? 2. Models: Does Size Matter: How important is model size? Is data size more important? What are the biggest misconceptions people have around models today? How does Richard respond to the suggestion that "many startups are wrappers around LLMs"? Are hallucinations a feature or a bug? 3. Where Does Value Accrue: Where does Richard believe most of the value will accrue; startup or incumbent? Which incumbents are best positioned to win? Which are the laggards and behind? What do many not see about the startup vs incumbent race in the AI war? 4. Open vs Closed: Which Wins: Does Richard favour Yann LeCun's open approach? Or is the world of AI more closed? What are the biggest challenges of an open ecosystem? What are the nuances that make both challenging? 5. Richard Socher: AMA: Why will carpenters be paid more than software engineers in 10 years? Why is AGI still way off? Are people too unrealistic? How much money does Google make off search every day? Why does that leave them vulnerable?

Brian Balfour is the Founder and CEO of Reforge. Previously, he was the VP of Growth @ HubSpot. Prior to HubSpot, he was an EIR @ Trinity Ventures and founder of Boundless Learning and Viximo. He advises companies including Blue Bottle Coffee, Gametime, Lumoid, GrabCAD, and Help Scout on growth and customer acquisition. In Today's Episode with Brian Balfour We Discuss: 1. Entry into Growth and Lessons from Hubspot: How did Brian make his entry into the world of growth? What does Brian know now about growth that he wishes he had known when he started in growth? What are 1-2 of his single biggest takeaways from his time at Hubspot that impacted his mindset? 2. The Foundations: What is growth? What is it not? What does Brian mean when he says "all growth can be boiled down to 4 things"? When is the right time to bring in your first growth person? Should the first growth person be senior or junior? Should the growth team be standalone or sit within an existing function? 3. The Importance of Product Channel Fit: What is product channel fit? How should founders approach it? How do you know when you have it? What are the single biggest mistakes founders make with regards to PCF? 4. Next Comes Channel Model Fit: What is channel model fit? How should founders approach it? What are clear indicators that you have or do not have channel model fit? What are the biggest mistakes founders make with CMF? 5. Finally, Model Market Fit: What is model market fit? How should founders approach it? What are clear indicators that you have or do not have model market fit? What are the biggest mistakes founders make with MMF? 6. Brian Balfour: AMA: Why is product market fit not enough? What does Brian mean when he says "revenue does not create usage"? What are the biggest dangers of mixing customers and users? What do Hubspot do better than anyone else to know when an existing product/strategy is dying? Is it always better to diversify marketing channels?

Tim Urban is the writer/illustrator and co-founder of Wait But Why, a long-form, stick-figure-illustrated website with over 600,000 subscribers and a monthly average of half a million visitors. He has produced dozens of viral articles on a wide range of topics, from artificial intelligence to social anxiety to humans becoming a multi-planetary species. Tim’s 2016 TED main stage talk is the third most-watched TED talk in history with 66 million views. In 2023, Tim published his bestselling book What’s Our Problem? A Self Help Book for Societies. In Today's Episode with Tim Urban We Discuss: 1. The Founding of Wait by Why: What was the a-ha moment for Tim that Wait but Why should be his life's work and sole focus? What does Tim know now that he wishes he had known when he started? What does Tim believe he is running away from? Why is he so fearful of constraints? 2. Wait But Why: The Scaling Journey to 600,000 Subs: What was the first piece to really go viral? How did that change the trajectory? What single piece is Tim most proud of? What piece is he least proud of? What has been the hardest element of scaling Wait But Why? What was the most surprising and unexpected elements of Wait But Why's scaling? 3. Topic Selection: Choosing What To Write: What does the process look like for Tim when deciding what topic to write about? How does Tim know what his audience will want to hear about vs what they will not? What topics has Tim thought would be interesting but post initial research, are not? 4. The Writing Process: How does Tim approach the writing process? How has his changed over time? What mechanisms does Tim put in place to avoid writers block? What are some of Tim's biggest tips to aspiring writers and authors? 5. The Distribution Process: How does Tim approach distributing the content once produced? What works? What does not? Why did Tim choose newsletter, Twitter and Instagram as his channels of choice? How important has the newsletter been to the growth of the business? 6. AI: Super-Intelligence and The Future: On reviewing his pieces on AI back in 2015, what does he believe he got right? What would he change with the benefit of hindsight? Is Tim more or less positive looking forward at AI proliferating through all of society? What is Tim most concerned about in the world right now?

Sam Lessin is a Co-Founder and Partner @ Slow Ventures with a portfolio including the likes of Airtable, Robinhood, Slack, Solana, PillPack and many more unicorn companies. Prior to Slow, Sam was a VP Product at Facebook having sold his company to Meta. Frank Rotman is a founding partner of QED Investors, one of the leading fintech-focused venture firms investing today with a portfolio including the likes of Klarna, Kavak, Quinto Andar, Credit Karma and more. As for Frank, prior to QED, Frank was one of the earliest analysts hired into Capital One and spent almost 13 years there helping build many of the company’s business units and operational areas.  Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few. Prior to SaaStr, Jason was an entrepreneur, selling EchoSign to Adobe for $100M where it is now a $250M ARR product. In Today's Discussion on Why Seed is Broken We Discuss: 1. The Seed Model Was Broken and What Comes Now: Why does Sam Lessin believe the model for seed of a "factory line" was broken? What does he believe will replace it? Why does Jason Lemkin argue that this might not be the case for SaaS and enterprise? 2. Round Construction: YC, Multi-Stage Funds and Party Rounds: Why does Sam Lessin believe we have seen the end of party rounds? Why does Jason Lemkin disagree and we will see more than ever? Why does Sam Lessin believe the factory model of YC churning out companies is over? Where does Jason Lemkin believe the value lies in the YC model? Will the multi-stage funds remain in seed? How has their entrance and deployment changed the seed market? 3. VC Value Add at Seed: Is it BS? Why does Jason believe all talent arms in venture firms have failed? Why does Sam believe that no VCs provide value? Do the best founders really need help? Why do Jason and Sam disagree? 4. What Happens Now: Why does Jason believe that every manager can write off their fund from 2021? Who will be the winners in seed in the next 10 years? Why does Sam believe if you want to bet on AI, just bet on Meta or Microsoft? What will happen to the many companies with no PMF but 10 years of runway?

Jason Lemkin is the Founder @ SaaStr one of the best-performing early-stage venture funds focused on SaaS. In the past, Jason has led investments in Algolia, Pipedrive, Salesloft, TalkDesk, and RevenueCat to name a few. Prior to SaaStr, Jason was an entrepreneur, selling EchoSign to Adobe for $100M where it is now a $250M ARR product. In Today's Episode with Jason Lemkin We Discuss: 1. WTF is Happening At Seed Right Now: Why does Jason believe seed is more active than ever? Is the pricing of seed rounds impacted since the downturn? Why does Jason believe it is not only not the end of party rounds but just the beginning of them? Why does Jason believe you cannot fail if you have $1M in ARR and an amazing founder? Why does Jason believe that seed investors cannot participate in "hot seed rounds" anymore? 2. Is Series A a Dead Zone: How does Jason analyze the Series A and B environment today? What has changed in what investors expect and want to see in potential Series A and B investments? What happens to the many companies who raised pre-emptive Series As and have 10 years of runway but no product-market fit? Why does Jason believe founders should offer to give the money back when it is not working? What happens to the Series A and B market in the next 18 months? When does it come back? 3. Growth: People are Too Negative! Why does Jason believe that growth is more active than many are giving credit for? What are the ARR benchmarks required to get a good growth round term sheet today? Why does Jason believe that VC DD is a load of BS? Why does Jason believe that every VC has fraud in their portfolio? Will they come out? 4. Ring That Bell: IPOs and M&A: Why does Jason believe 2024 will be an amazing year for IPOs? Why does much of the IPO market rely on Stripe and Databricks? What is needed for an amazing 2024 IPO market? How does Jason evaluate the M&A market in 2024? Will regulation get in the way? 5. Jason Lemkin: AMA: Why does Jason Lemkin believe this generation of workers will never work hard again? What is the only way for seed funds to make money investing in serial entrepreneurs? What does Jason know now that he wishes he had known when he started investing?

Vinod Khosla is the Founder of Khosla Ventures, one of the leading venture firms of the last decade with investments in OpenAI, Stripe, DoorDash, Commonwealth Fusion Systems and many more. Prior to founding Khosla, Vinod was a co-founder of Daisy Systems and founding CEO of Sun Microsystems. In Today's Episode with Vinod Khosla We Discuss: 1. The State of AI Today: Does Vinod believe we are in a bubble or is the excitement justified based on technological development? What are the single biggest lessons that Vinod has from prior bubbles? What is different about this time? What is Vinod concerned about with this AI bubble? 2. The Future of Healthcare and Music: How does Vinod evaluate the impact AI will have on the future of healthcare? How does Vinod analyse the impact AI will have on the future of music and content creation? Does Vinod believe that humans will resist these advancements? Who will be the laggards, slow to embrace it and who will be the early adopters? 3. Solving Income Inequality: Does Vinod believe AI does more to harm or to hurt income inequality? What mechanisms can be put in place to ensure that AI does not further concentrate wealth into the hands of the few? Does Vinod believe in universal basic income? What does everyone get wrong with UBI? 4. The Future of Energy, Climate and Politics: Why is forcing non-economic solutions the wrong approach to climate? What is the right approach? Why is Vinod so bullish on fusion and geothermal? How does fusion bankrupt entire industries? How does the advancements in energy and resource creation change global politics? Does Vinod believe Larry Summers was right; "China is a prison, Japan is a nursing home and Europe is a museum"? 5. Vinod Khosla: AMA: What is Vinod's single biggest investing miss? What does Vinod know now that he wishes he had known when he started investing? Why did the Taylor Swift concert have such a profound impact on him? What was Marc Andreesen like when he backed him with Netscape in 1996?

Ilir Sela is the Founder and CEO of Slice, the all-in-one ordering and marketing tech platform for local pizzerias. Through its partnerships, Slice has driven over $1B in earnings for over 18,000 independent pizzerias nationwide. Fun fact, Slice is also one of the largest employers in Macedonia and at one point, employed so many people there, they had to start their own school to train more people. Before Slice, Ilir started Nerd Force and sold it in 2008. Huge thanks to Jeff Richards (GGV) and Ben Sun (Primary) for some amazing questions today. In Today's Discussion with Ilir Sela We Discuss: 1. From Macedonia to the Bright Lights of NYC and Bentley Buying: How Ilir made his way into the world of startups having grown up in Macedonia? How did his less affluent upbringing impact his approach to company building? How does Ilir think about the importance of money? How did he come to buy a Bentley? What does Ilir know now that he wishes he had known when he started? 2. Why Bootstrapped Was Best & The Decision to Fundraise: Why did Ilir scale the business to $4M in revenue without ever fundraising? What does Ilir believe are the benefits of scaling businesses with less money? What would Ilir have done differently had he raised money earlier? What advice does Ilir have for founders who see competitors raising more money than them? 3. Why Delegation is BS and Your Upbringing F***** You Up: Why does Ilir believe that much of our upbringing can instill principles which make us a worse leader? Why does Ilir believe it is BS to hire great people and get out of the way? What are the single biggest mistakes Ilir sees founders make in company scaling? What have been some of Ilir's biggest lessons in talent acquisition? 4. Decision-Making 101: How does Ilir analyze his decision-making framework today? Where does he need to improve as a leader today? What does he need to do to get there? What has been the single best decision he made with Slice? What did he learn from it? What has been the worst decision he has made in the scaling process? How did that change his mindset?

Lori Jimenez is the Chief Revenue Officer at WorkRamp where she is responsible for sales, customer success, solutions engineering, sales development, and revenue operations. Over her 25-year career, Lori has a track record of scaling high-growth GTM teams at companies including Google, TripActions/Navan, Facebook, and Box. In Today's Episode with Lori Jimenez We Discuss: 1. From a First Sales Job at 15 Years Old to Leading Sales Teams at Google and Facebook: How Lori made her foray into the world of sales at the age of 15? What are 1-2 of Lori's biggest takeaways from her time at Google, Facebook and Box? What does Lori know now that she wishes she had known at the start of her career in sales? 2. The Sales Playbook: What, When and How: How does Lori define the "sales playbook"? What is it not? Should the founder be the one to create the sales playbook? When is the right time for founders to make their first sales hires? What is the right profile for the first sales hires? Should founders hire 2 sales reps at a time? What are the pros and cons? 3. The Hiring Process: Building the Sales Team: How does Lori structure the hiring process for all new sales hires? What are the must-ask questions to ask in every sales hiring meeting? What are the biggest red flags founders should look for when hiring for sales? What are Lori's biggest lessons on how to navigate compensation discussions with potential sales hires? What are Lori's biggest lessons on what title negotiation says about a candidate? What are the single biggest mistakes founders make when hiring for sales teams? 4. Scaling the Machine: Bringing the Dollars In: How does Lori approach discounting? When is the right time to do it? Is old-school enterprise sales and entertaining dead? How has it changed? How does Lori structure deal reviews? What is a good vs a bad reason to lose a deal? How does Lori approach multi-year deals? What is good? What is bad?

Marcelo Claure is the Founder & CEO of Claure Group, a multi-billion-dollar global investment firm. He is the Executive Chairman and Managing Partner of Bicycle Capital, a $500M Latin America-focused growth equity fund, and was appointed Chairman in Latin America of SHEIN, the global #1 on-demand fashion company in the world. Claure was also the CEO of SoftBank Group International where he launched SoftBank’s $8B Latin America Funds, and had direct oversight for SoftBank's operating companies. As an entrepreneur, Marcelo built Brightstar from a small local distributor to the world’s largest global wireless distribution and services company. In addition, Claure led the turnaround of US wireless telecommunications company Sprint and helped orchestrate its US$195 billion merger with T-Mobile. Shu Nyatta is the founder of Bicycle Capital. Before Bicycle, Shu was most recently a Managing Partner at SoftBank Group International, where he launched and managed two separate funds - the SoftBank Latin America Fund and the Opportunity Fund for early-stage investments in US-based founders-of-color. In the first part of his SoftBank career, Shu was a founding Partner of SoftBank's Vision Fund. Several companies have retained him on their boards as an independent board member following his departure from SoftBank, including Lemonade (NYSE: LMND), Kavak and Tribal Credit. Shu also serves on the board of Endeavor Global - the leading global community of, by and for high-impact entrepreneurs. In Today's Episode Featuring Bicycle Capital We Discuss: 1. From Deploying $10BN at Softbank to Founding Bicycle Capital: What was the founding moment for Marcelo and Shu in the founding of Bicycle? What does Shu believe is Marcelo's superpower? How has working with Marcelo changed the way he thinks? Why does Marcelo believe that he is not a good investor? How does Shu make him better, specifically? 2. Lessons from Investing $10BN at Softbank: What are 1-2 of the biggest lessons from investing $10BN over the last few years at Softbank? How did missing OpenAI and Nubank impact how Shu and Marcelo think and invest today? Why was losing $150M on Softbank's FTX investment, the biggest lesson of Marcelo's career? What are Marcelo and Shu doing differently at Bicycle, having seen how it went at Softbank? 3. The Venture World is Changing: Why do Marcelo and Shu believe the world of venture is changing? How is it changing most? Why are founders going directly to LPs to raise rounds today, over going to VCs? Do Marcelo and Shu believe that many VCs provide value? Who will win in the next 10 years of venture? Who will lose? Why do Marcelo and Shu believe you should not invest in founders that do not take your advice? Do Marcelo and Shu agree with the statement that "the best founders do not need your help"? 4. LATAM is Under Construction: It is Time to Build: What are the two reasons that the next decade will be the best ever for LATAM? What are the biggest misconceptions about the LATAM tech market? How do Marcelo and Shu answer the question of the lack of liquidity available with few M&A deals taking place and very few LATAM companies listing on the NASDAQ? How do Marcelo and Shu evaluate the withdrawal of foreign capital from LATAM tech markets? Is it good or bad? Have a load of US funds lost money on early-stage LATAM deals?

Stephane Kurgan is widely considered one of the best operators in Europe. During his tenure as COO @ King, King went from $65m to $2.4B in bookings, from 100 to 2,400 employees, and did a $7B IPO before being acquired by Activision Blizzard. Prior to joining King, Stephane served as CFO of Tideway Ltd. (acquired by BMC Software) and was the co-founder and CEO of Digital Reserve. Today, Stephane serves as a Venture Partner at Index Ventures, one of the leading venture firms of the last decade and more recently as an executive advisor at Technology Crossover Ventures. In Today's Episode with Stephane Kurgan We Discuss: 1. From Belgium Boy to Europe's Leading Operator: How a CD Rom company was the starting place for one of Europe's best executives? What does Steph believe he is running away from? What does Steph know now that he wishes he had known when he started? 2. Four Criteria of Truly Great Leaders: What four traits do all truly special leaders have? What are the 1-2 that are the hardest to find in great leaders today? Why does Steph believe that even the best leaders are wrong 40% of the time? How does Steph approach decision-making? How has it changed over time? What is the most toxic element of decisions within companies today? When does Steph change plan because a decision is wrong vs stick to it? 3. Speed of Execution and Mission Statements: How important does Steph believe speed of execution is today? What are the elements that one can go fast on vs go slow and be very deliberate on? What elements has Steph gone fast on in the past that led to a mistake? How would he have changed his approach with the benefit of hindsight? Why does Steph believe that mission statements have different value at different company stages? What is Steph's biggest advice to founders on creating mission statements? 4. Delivering Feedback and Maintaining Trust: What are 1-2 of Steph's biggest lessons when it comes to delivering feedback well? What are the biggest mistakes founders make when delivering feedback today? Can trust be regained once lost? How? Does Steph start from a position of full trust or is it gained gradually over time?

Sri Batchu currently leads Growth at Ramp. He previously led Growth Strategy and Operations at Instacart where he also helped grow their Ads business. Prior to that, he was one of the first 50 employees at Opendoor where he built, scaled, and managed a variety of business teams including Analytics, Sales, and Pricing.  During his time, the company grew from $100M to $5B+ revenue and to 1500+ people.  He started his career in management consulting at McKinsey and also held various investing roles including in private equity at Bain Capital.  In Today's Episode with Sri Batchu We Discuss: 1. From Harvard to Private Equity to Leading the Best Growth Teams: How did Sri make his way into the world of growth with Instacart and Opendoor? What are 1-2 of his biggest takeaways from his time at Instacart? How did it change his approach and mindset towards growth? How did Zilllow burn themselves by buying homes? What did that teach Sri about hitting metrics and goal setting in growth teams? 2. Growth Teams Should Fail and Fail Fast: What is the right ratio of success to failure within growth teams? What are specific ways that growth teams can increase the speed with which they fail? How are the best post-mortems run? Who joins them? Who leads the agenda? What are Sri's biggest lessons on how to set the right goals? Where do so many growth teams go wrong with the North Star that they set for themselves? 3. Building the Bench: Hiring a Growth Team: When is the right time to make your first growth hires? What profile should your first growth hires be? How should one structure the interview process when hiring growth teams? What is the first question Sri asks all new hires? Why does Sri believe you have to hire slowly? Should candidates do case studies as part of the process, if so, on a new company or on the company they are interviewing for? 4. When Operators Become Investors: Why does Sri believe the best investors of the next 10 years will be operators? Why does Sri believe that operators can do due diligence to a higher level than traditional VCs? Why does Sri believe that investors should not take cold emails? Why does Sri believe that it is not wrong for an investor to hire from their portfolio companies? What does Sri believe the future of venture holds over the next 10 years?

Adam Mosseri is the Head of Instagram, where he is responsible for overseeing the engineering, product, and business teams and leading Meta’s efforts on creators and Reels. Adam has been at Meta for more than fifteen years. He started at Meta as a designer for Facebook's mobile app before moving to product management, where he led the Facebook News Feed product and engineering teams, and served as the Head of Facebook News Feed. Adam began his career founding a design consultancy focused on graphic, interaction, and exhibition design before joining TokBox as the company’s first designer. In Today's Discussion with Adam Mosseri We Discuss: 1. From Designer to Product Leader to Instagram CEO: What did Adam learn from his first job bartending? How did it impact his approach to customer support and research? What are the top 1-2 pieces of advice Adam would give to someone wanting to make the move from individual contributor to leader? If Adam was "not amazing at anything", what did he do that enabled him to rise above the rest and become CEO of Instagram? What have been 1-2 of the biggest lessons from working with Mark Zuckerberg for 15 years? 2. A Deep Dive on the Wild Times as Instagram CEO: What has been Adam's single biggest mistake as CEO of Instagram? What does Adam believe is the least known feature within Instagram that has made them successful? What does Adam believe has been the biggest product decision he has made as CEO? Why does Adam believe that Instagram is too complicated as a product? Who does Adam believe is the most formidable competitor to Instagram? Was Instagram Reels a simple copy of TikTok? What have Instagram learned from TikTok? How does Adam respond to the statement that Instagram is a "copy-cat machine" and lacks innovaton? 3. Threads: The Journey from 0-100M Users in Three Days: Did Adam and the team expect the response they got to Threads? Why did they decide to break Threads out into a separate app? What went into bootstrapping the Threads friendship and interest graph? What was the Threads influencer activation strategy? What worked? What did not? Did they pay influencers? How did they choose which verticals to focus on? What is Adam's core focus with Threads today? How is the team analysing and measuring retention? What are their goals? What are the 1-2 core reasons why Threads would not work? How do they aim to prevent them? In 12 months, where will Threads be? 4. The Future of Consumer Social: What Happens Now? Does Adam believe we have seen the transition from the social graph to the interest graph? Is it that binary? Is it possible to have both the interest and the friendship graph all in one app? How does the monetization potential differ when comparing Threads (text) to Instagram (visual)? How important is it for the next consumer social platforms to have stars that are native to their platform (Mr Beast on Youtube, D'Amelio on TikTok etc.)

Jean-Denis Greze is Chief Technology Officer at Plaid where oversees global product business units across North America and Europe. Prior to joining Plaid, Jean-Denis was Director of Engineering at Dropbox. Jean-Denis is also a prolific angel investor with a portfolio including the likes of Nex Health, Merge.dev and Rupa Health to name a few. In Today's Episode with Jean-Denis Greze We Discuss: 1. The Journey to One of the Most Powerful CTOs: How JD made his way into the world of tech with his first role at Dropbox? How does JD analyse a Linkedin CV today? What are the signals of outperformers? What does JD know now that he wishes he had known when he started in tech? 2. Hiring the Best: 101: What are JD's single biggest lessons on hiring the best talent? What have been some of JD's biggest hiring mistakes? Why does JD believe founders need to be as good at firing as they are hiring? Does JD believe people can scale with the scaling of a company? If they do not scale, do you layer them or do you let them go? How does JD determine whether to bring in an external candidate vs promote someone from within? 3. Product Differentiation is not Sustainable: Why does JD believe that product differentiation is not sustainable? Why is UX as a moat BS? How does this lead JD to suggest Salesforce is a short in the public markets? Why does JD believe that Snowflake is also a short? What does Snowflake teach us about the different stages of product market fit? What are the biggest mistakes founders make when analyzing product market fit? 4. Remote Work, Titles and Entitlement: Why does JD believe most tech employees treat their employer in the same way French citizens treat the French government? How does JD analyse the impact of remote work on both productivity and culture? Why does JD believe titles are BS in the beginning but matter with scale? Why does JD believe that you should not hire for the long term?

Lauryn Isford is the Head of Product Growth at Notion, managing Notion's product-led growth engine and self-serve business. Before Notion, she led growth at Airtable, and previously worked on growth teams including Meta, Dropbox, and Blue Bottle Coffee. Lauryn is an active angel investor and advisor supporting companies building product-led go-to-market motions.  In Today's Episode with Lauryn Isford: 1. From Blue Bottle to Airtable and Notion: How did Lauryn first make her way into the world of product and growth? What are 1-2 of her biggest takeaways from Dropbox, Facebook and Blue Bottle? What does Lauryn know now that she wishes she had known when she started? 2. What is Growth: 101: How does Lauryn define growth? What is it not? When is the right time to make your first growth hire? What profile should your first hire in growth be? What are the single biggest mistakes founders make when hiring growth teams? 3. Mastering the Onboarding Experience: What are the core elements of a successful onboarding experience? How important is time to value in onboarding today? What are the biggest mistakes product teams make in company onboarding? What is the most effective onboarding technique and workflow in PLG today? Why are 90% of current onboarding's done badly? 4. Making Growth work with the Rest of the Org: What are the single biggest barriers to growth and product working together well? What can leaders do to make their growth teams work well with product teams? How can growth teams experiment and test with product without messing up codebases?

Dave Clark is the CEO of Flexport, the global freight forwarder and logistics platform that has now raised over $2.5BN to build the category leader. Prior to Flexport, Dave began his career at Amazon in 1999 as an Operations Manager, working his way up to become the CEO of Amazon’s worldwide consumer business in 2021. By the time Dave left, he was responsible for over 1 million employees. Dave spearheaded the launch of Amazon Robotics and grew the company’s logistics divisions to include Amazon’s own planes, trailers, and last-mile delivery vehicles through Amazon’s own delivery network (which today ships more packages than FedEx and UPS). Huge thanks to Ryan Peterson for some amazing question suggestions today. In Today's Episode with Dave Clark We Discuss: 1. From Operations Manager to CEO @ Amazon: How did Dave Clark make his way into the world of startups with Amazon in 1999? What are 1-2 of his biggest lessons from spending 23 years at Amazon? What are 1-2 of his biggest takeaways from working alongside Jeff Bezos for 23 years? 2. How Big Leaders Make Big Decisions: What is Dave's decision-making framework when it comes to big decisions? What is the biggest decision Dave made that went wrong? How did it impact his mindset? How does Dave think through prioritisation as a leader today? What are the biggest mistakes founders make when it comes to focus? 3. How Big Leaders Hire Big Talent: What are 1-2 of Dave's biggest lessons on what it takes to acquire the best talent? Does Dave believe that people can scale with the scaling of the company? How does Dave think through the challenge of promoting internally vs bringing in external talent? Why does Dave like to hire people straight out of college? What are the benefits? 4. How Big People Deal with Big Problems: Kids, Money and Ego What are 1-2 of Dave's biggest lessons when it comes to parenting? How does Dave think about giving his kids the same hunger and ambition, when they are brought up in such affluent environments? How does Dave assess his own relationship to money? How has it changed over time? What does a truly great marriage mean to Dave? Where do so many go wrong in trying to find work-life balance?

Sheel Mohnot is a Co-Founder and General Partner @ Better Tomorrow Ventures, a $225M fund that leads rounds in pre-seed and seed-stage fintech companies globally. Sheel and Jake (his co-founder) invested for many years together before founding BTV and wrote checks into Mercury, Flexport, Ramp, and Hippo Insurance to name a few. As for Sheel, before BTV he ran 500 Fintech for close to 7 years, and before that was a founder, founding two companies, both of which were acquired. In Today's Episode with Sheel Mohnot We Discuss: 1. VC Needs to Change: Why does Sheel believe that VCs should have smaller funds? What are the biggest misalignments between founders and VCs today? What are the biggest points of friction between VCs and their LPs today? 2. VC in 10 Years Time: Who are going to be the winners in venture in 10 years time? Who are going to be the losers? Will micro-funds be bigger or smaller as a segment of the ecosystem? Will solo-GPs be bigger or smaller? Were they a zero-interest rate phenomenon? 3. The Errors of a Bull Market: What does Sheel believe are the single biggest mistakes made by VCs between 2020-2022? Did Sheel take liquidity off the table in the last few years? What have been some of his biggest lessons on when to sell? How does Sheel evaluate the flood of capital into emerging markets in the bull market? What happens now? Fintech is also experiencing the same challenging time, how does Sheel assess what is happening in the fintech financing market today? 4. Building a Fund: Lessons, Mistakes and Advice Scaling to $225M: What are the single biggest mistakes Sheel and Jake have made in the fun scaling? How has it impacted their mindset? What does Sheel know now about fund management that he wishes he had known at the beginning? What advice does Sheel give to emerging managers today, raising their first and second funds?

Kevin Egan is the Global Head of Enterprise Sales at Atlassian and brings more than 25 years of enterprise sales experience and leadership to the company. Prior to his current role, Kevin served as the Vice President of North America Sales at both Slack and Dropbox and has held various senior sales leadership positions at Salesforce. In Todays Episode With Kevin Egan We Discuss: 1. The Makings of a Truly Great Enterprise Sales Leader: How did Kevin first make his way into the world of enterprise sales? What does Kevin know now that he wishes he had known when he entered sales? What advice would Kevin give to a new sales leader today starting a new role? 2. The Sales Playbook: How does Kevin define "the sales playbook"? Does the founder have to be the one to create the sales playbook When is the right time to hire your first salespeople? Should they be senior or junior first? What are the different types of reps to hire in the early days? Should you hire two at a time? 3. PLG vs Enterprise: Does Kevin believe it is possible to run both PLG and enterprise playbook at the same time? How does one know when they are ready to scale from PLG into enterprise? What are the signs? What do companies need to change in the way their sales team, is structured to make the transition from PMG to enterprise sales? What are the single biggest mistakes Kevin sees founders make in the scaling from PLG to enterprise? 4. Hiring the Sales Team: What non-obvious characteristics and attitudes should we look for in sales reps? How does Kevin structure the hiring process for all new additions to sales and revenue teams? What makes good PLG sales leaders? How are they different from enterprise sales leaders? What questions and case studies are most revealing for you in identifying them? What have been some of Kevin's biggest lessons on comp structure for these early rep hires? 5. Making the Machine Work: How does Kevin build trust with his early sales rep hires? What works? What does not? How does Kevin balance hitting the quarterly revenue target with longer-term pipeline strategy? How does Kevin manage when a quarter is missed? What is the right approach? How does Kevin approach post-mortems and deal reviews? How often? What do the best entail?  

Simon Sinek is an optimist and author, as we discuss in the show today. Simon is best known for his TED Talk on the concept of WHY (62M views), and his video on millennials in the workplace (80M views in 7 days). Simon is also a bestselling author including global bestseller Start with WHY, Leaders Eat Last and The Infinite Game. In addition, Simon is the founder of The Optimism Company, a leadership learning and development company, and he publishes other inspiring thinkers and doers through his publishing partnership with Penguin Random House called Optimism Press. In Today's Discussion with Simon Sinek We Discuss: 1. The Makings of Simon Sinek: In what ways does Simon believe that his parents and upbringing shaped who he is today? What does Simon want to be when he grows up? What was the catalytic moment to the "Simon Sinek brand"? When was that big break moment? 2. Identity: Simon has said before, "I define myself by who I am and not what I do". Is it wrong to define yourself by what you do? What do you do if you do not know who you are? What do you do if you do not like the answers to who you are? Is it possible to change who you are? What does that process look like? What is Simon's biggest advice to those looking to find a greater sense of self and identity? 3. Trust: Does Simon start relationships with inherent trust and it is there to be lost or no trust and it is there to be gained over time? When has someone broken Simon's trust? How did it impact how he approaches trust today? In the case of cheating in a relationship, does Simon believe it is possible to regain trust over time? Simon has said before, "trust is built on telling the truth". Does it ever make sense or is even right to tell a little white lie in a relationship? 4. Creating Safe Spaces: How can we create safe spaces for our partners to be their full selves? Does this differ professionally and personally? What are the biggest mistakes people make in building safe spaces? 5. Listening: What does great listening in a relationship mean? How can we do it better? Often people jump from listening to solution mode, is that wrong? Why does Simon have a rule of “no crying alone”. What does it do and how is it productive? When was the last time Simon cried? 6. Simon Sinek: AMA: What is success to you? Can one be “successful” and unhappy? What is the difference between happiness and joy?

Douwe Kiela is the CEO of Contextual AI, building the contextual language model to power the future of businesses. Last month Contextual closed a $20M funding round including Bain Capital, Sarah Guo, Elad Gil and 20VC. He is also an Adjunct Professor in Symbolic Systems at Stanford University. Previously, he was the Head of Research at Hugging Face, and before that a Research Scientist at Facebook AI Research. In Today's Episode with Douwe Kiela We Discuss: 1. Founding a Foundational Model Company in 2023: How did Douwe make his way into the world of AI and ML over a decade ago? What are some of his biggest lessons from his time working with Yann LeCun and Meta? How does Douwe's background in philosophy help him in AI today? 2. Foundational Model Providers: Challenges and Alternatives: What are the biggest problems with the existing foundational data models? Will there be one to rule them all? How does the landscape play out? Why does Douwe believe OpenAI's data acquisition strategy has been the best? 3. Data Models: Size and Structure: Why does Douwe believe it is naive to think the open approach will beat the closed approach? What are the biggest downsides to the open approach? Does the size of data model matter today? What matters more? How important is access to proprietary data? Are VCs naive to turn down founders due to a lack of access to proprietary data? 4. Regulation and the World Around Us: How does Douwe expect the regulatory landscape to play out around AI? Why is Europe the worst when it comes to regulation? Will this be different this time? How does Douwe analyse Elon's petition to pause the development of AI for 6 months? Do founders building AI companies have to be in the valley?

Jennifer Hyman is the Co-Founder and CEO of Rent the Runway, the world’s first and largest shared designer closet. Under Jennifer’s leadership, RTR has made history by being the first company to go public with a female founder/CEO, COO, and CFO. Jennifer serves on the Board of The Estée Lauder Companies and Zalando, and also is a Founding Member of the NYSE Board Advisory Council, a Member of the Women.nyc Advisory Board and a Member of the Launch with GS Advisory Council for Goldman Sachs. In Today's Episode with Jennifer Hyman We Discuss: 1. The 14-Year Overnight Success: Scaling Rent The Runway To IPO: What was the a-ha founding moment for Jennifer with RTR? What does Jenn know now that she wishes she had known at the beginning? Does Jenn believe that naivete is good or not when starting a business? 2. Building the Best Team: What have been Jenn's single biggest lessons when it comes to acquiring the best talent? What have been Jenn's biggest hiring mistakes over the years? How does Jenn approach the interview process? Why does Jenn not focus on their professional career and achievements? What questions does she ask? What does Jenn believe are the single biggest mistakes founders make when building their teams? 3. Building the Business for IPO and Beyond: Why does Jenn wish she had run RTR as a private company in the same way she does now as a public company? How does the way you run the company differ? What about the unit economics of RTR suggesting it is a fundamentally better business than apparel competitors? How have their margin profiles changed over time? Why does Wall St not love RTR? What is required for that to change? Why does Jenn believe the street is wrong on how they analyse RTR? 4. Boards 101: Leading and Learning from Estee Lauder: What are Jenn's biggest lessons to founders on how to manage boards successfully? What have been 1-2 of Jenn's biggest lessons from being on the Estee Lauder board? What do the best board members do? What do the worst board members do?

Akin Babayigit is a serial entrepreneur and an active angel investor. He is currently the Founder and COO of Tripledot Studios, one of the fastest-growing mobile gaming companies in the world, which was recently valued at over $1.4BN. In just 4 years, Tripledot grew to generate several hundred million dollars per year in revenue and currently entertains over 50 million people every month. Tripledot was recently named as the #1 fastest-growing European company by FT, as well as being named as the fastest-growing Tech business in the UK, in the annual “UK Tech Awards”. In Today's Episode with Akin Babayigit We Discuss: Entry into the World of Startups and Gaming: How Akin made his way from Turkey to HBS and founding a unicorn in Tripledot? How did the lack of a father figure impact Akin's approach to parenting? What are 1-2 of Akin's biggest takeaways from his time at Facebook, Skype and King.com? What advice would Akin give to all new joiners at a company today? 90% of Startup Advice is Total BS: BS Myth #1: "You have to be passionate about your domain". Why does Akin disagree with this? If you do not have passion for the domain, what do you have to have? BS Myth #2: "You have to be solving a real problem". Why does Akin disagree with this mantra? If you are not solving a real problem, what should you be solving? BS Myth #3: "When you do a startup, your life will suck for a long period of time". Why does Akin strongly disagree with this? Does it get easier over time? What does Akin advise founders to make the earlier days easier? BS Myth #4: "Focus is everything. You should focus on a single thing and only do that." Why does Akin believe that focus can be dangerous? How should founders know when to pivot vs when to keep going? BS Myth #5: "Mission and vision statements are so important." Why does Akin believe that the majority of mission statements are BS? Is it worth having them at all? BS Myth #6: "You should hire people with domain experience." Why does Akin believe you should hire people who do not have domain experience? What does Akin look for in these candidates? What have been his biggest hiring mistakes? How has his hiring changed over time? BS Myth #7: "Speed is the most important thing." Why does Akin believe that speed can be dangerous? When is it right to go fast vs go slow? BS Myth #8: "Valuations matter and you should optimize." Why does Akin believe that valuations do not matter in the long run? How should founders approach the valuation discussion with this in mind?

Rob Go is a co-founder and Partner at NextView, one of the leading seed firms of the last decade with a portfolio including Attentive, Devoted Health, Whoop, and Grove Collaborative. Prior to co-founding NextView, Rob was an investor at Spark Capital and held product and product marketing roles at Ebay. He began his career as a consultant at The Parthenon Group. In Today's Episode with Rob Go We Discuss: 1. Entry into the World of Venture: How a cold call from a VC firm led to Rob entering the world of venture? Why does Rob believe venture is a young person's game? What does Rob know now that he wishes he had known when started in venture? 2. Preparing Docs for a Fundraise: What docs should fund managers have ready before they start the raise? How should they structure their data room? Where do the majority of LPs spend their time, document-wise? What are the single biggest mistakes emerging managers make preparing docs for a raise? 3. Meeting Your First LPs: What is the best way for emerging managers to meet LPs for the first time? Should they send the deck before or after the meeting? What questions should emerging managers ask to qualify LPs in or out of a meeting? What are some clear early signs that a first meeting went well? 4. Closing LPs: The Tips and Tricks: How important is it for a fund to have an anchor? How much of a fund should the anchor be? Are there different qualities of anchor LPs? Should managers ever sell part of their GP or give an LP part of the carry? What can managers do to enforce a sense of urgency to get LPs over the line? What are signs that an LP will not invest in the fund without rejecting you yet? Should emerging managers impose a minimum check size on new LPs?

Gina Gotthilf is a Co-Founder and COO at Latitud, an a16z-backed platform supporting the next generation of iconic tech startups in Latin America through digital products, a community and fund. Previously, Gina led growth and marketing at Duolingo from 3 to 200 million users via organic strategies and was part of the executive team. She also worked on the Mike Bloomberg presidential campaign, helping oversee the creation of digital ad campaigns at a historical budget, and led growth and community for Tumblr in Latin America. In Today's Discussion with Gina Gotthilf We Discuss: Entry into the World of Growth: How Gina went from working on a farm to leading growth for Tumblr in LATAM? What are 1-2 of Gina's biggest takeaways from her time leading growth for Duolingo? What does Gina know now that she wishes she had known when she entered the world of growth? 15 Top Tips and Secrets to Being Featured in the Best Publications: What is the best way to get in touch with journalists? What mistakes do founders have when they reach out to journalists? Should founders get in touch with more than one journalist at a publication? Should founders be explicit about the embargos they have on a story? Should they stick to them? Should founders be more wary of being published in a publication with a paywall? What materials should they send to journalists to get their attention? Should founders send press releases in early messages to journalists? How can founders control in some way what the journalist will ultimately publish? How long before the company wants the piece to come out, should they reach out to journalists? How can founders create FOMO when trying to get journalists to write their story? How can founders create social validity with journalists, when they are a small company? Once published, what should the distribution strategy look like? How can you get people you know to like and share content you are featured in? What are the top tips and tricks to get people to share content with you in? Should PR and Comms be an ongoing effort or static projects with news stories? What are the single biggest mistakes founders make in getting their company in the press?

Alex Lebrun is the Co-Founder and CEO of Nabla, an AI assistant for doctors. Prior to Nabla, he led engineering at Facebook AI Research. Alex founded Wit.ai, an AI platform that makes it easy to build apps that understand natural human language. Wit.ai was acquired by Facebook in 2015. Prior to Wit, Alex was the Founder and CEO of VirtuOz, the world pioneer in customer service chatbots, acquired by Nuance Communications in 2013. In Today's Episode with Alex Lebrun We Discuss: 1. Third Time Lucky and Lessons from Zuckerberg: How did Alex make his way into the world of startups with the founding of his first company? What worked with Alex's prior companies that he has taken with him to Nabla? What did not work that he has left behind? What were the single biggest takeaways for Alex from working with Mark Zuckerberg? How does Mark prepare for meetings? How does Mark negotiate so well? 2. Open vs Closed: Why does Alex believe the winning AI models will always be open? Why are open models not as transparent as people think they are? What are the biggest downsides to both open and closed models? Does Alex agree with Emad @ Stability that we will have "national data sets"? 3. Incumbent vs Startup: Who wins in the AI race; startups or incumbents? How important is access to proprietary data in winning in AI today? How does Alex respond to many VCs who suggest so many AI startups are merely "a thin layer on top of a foundational model"? Is that a fair critique? Which startups are best placed to challenge incumbents? Which incumbents have been most impressive in adopting AI into existing product suites? 4. Models 101: Size, Quality, Switching Costs: Why will the best companies switch the models that they use often? Will any models in action today be used in a year? How important is the size of the model? How will this change with time? In what way is new EU regulation around models going to harm European AI companies? 5. Location Matters: Who Wins: When looking at China, US and Europe, who is best placed to win the AI war? What are the biggest challenges Europe and China face? Why is the US best placed to win the AI race? What does it have to overcome first? If Alex were a politician, what would he do to ensure his country were best positioned?

Noah Weiss is the Chief Product Officer of Slack, overseeing the product team’s strategy and development. Over his seven years at Slack, Noah has led various parts of the product organization, including the self-service SMB business and product-led growth; the Virtual HQ team that launched huddles and clips; and the search and machine learning teams. Prior to Slack, Noah served as SVP of Product and Analytics at Foursquare. He started his career at Google leading the structured data search team and working on display ads. In Today's Episode with Noah Weiss We Discuss: 1.) Entry into Product and Road to Slack CPO: How did Noah make his first foray into the world of product with Google? What are 1-2 of his single biggest takeaways from his time with Google and Foursquare? What model did Noah learn at Google that he applies to product today? 2.) Product 101: The Foundations: Is product more art or science? If Noah were to put a number on it what would it be? What are product principles? What makes good vs bad product principles? What are the biggest mistakes that founders make when instilling product principles? Does Noah believe with Gustav Soderstrom, "talk is cheap and so we should do more of it"? 3.) How to Master Product-Led-Growth: What are some of Noah's biggest lessons on how to master PLG? What are the biggest mistakes Noah sees early stage founders make today when going for the PLG approach? How does he advise them? When is the right time to move into enterprise? What needs to change? How do you change who you build product for? The buyer or the user? Why does Noah believe product speed will always be the most important thing in product? 4.) The Internals of Slack: How does Slack do post-mortems today? Who comes? Who sets the agenda? How has this changed in a world of remote? What does it take to do them well? How do Slack do product testing pre-launch of new products? Do they know when something is going to be a hit? What did they think would be a massive hit that turned into a flop? What does Noah believe is the biggest near death product experience for Slack? What happened? How did they get through it? Why do Slack buy other companies? How do they think through the decision of buy vs build? When do acquisitions work? When do they not work?

Rishi Sunak is the Prime Minister of the United Kingdom. He was previously appointed Chancellor of the Exchequer from 13 February 2020 to 5 July 2022. He was Chief Secretary to the Treasury from 24 July 2019 to 13 February 2020, and Parliamentary Under Secretary of State at the Ministry of Housing, Communities and Local Government from 9 January 2018 to 24 July 2019. Before entering the world of politics, Rishi co-founded an investment firm. In Today's Episode with Rishi Sunak We Discuss: 1. The United Kingdom: Open for AI: Open for Business Why does Rishi believe the UK is best placed to lead the way for innovation in AI? What can the government do to ensure the public and private sectors work together most efficiently? Why has Rishi created an entirely new division just for this? How does this change how decisions for AI and technology are made? 2. $100M Funding: The Largest Government Funding in the World: Why did Rishi decide to allocate the largest pool of capital of any nation toward AI safety? What is the strategy for the $100M? How will it be invested? Who will manage it? What are the challenges and opportunities in setting up this $100M funding program? 3. Education: Attracting the Best in the World: What has Rishi done to ensure the best talent in the world, wants to and can work in the UK? What new initiative has Rishi put in place to ensure the world's brightest students can freely move to and work in the UK? What can be done to ensure the UK continues to foster the same level of homegrown talent that we always have done? What can we do to improve our current education system for AI even further? Why does Rishi believe one of the greatest opportunities for AI lies in education and teaching? 4. Making Regulation Work Effectively: How does Rishi think about creating regulation which is both effective and not prohibitive? What can we do to create a government that moves at the speed of business? What does Rishi believe are the biggest mistakes made in regulatory provisions? What are we doing to avoid them with AI in the UK?

Larry Summers is the Former Treasury Secretary and one of America's leading economists. In addition to serving as 71st Secretary of  the Treasury in the Clinton Administration, Dr. Summers served as Director of the White House National Economic Council in the Obama Administration, as President of Harvard University, and as the Chief Economist of the World Bank. Huge thanks to Sarah Cannon for the intro to Larry today. In Today's Episode with Larry Summers We Discuss: 1. The Journey to Being One of the World's Leading Economists: How Larry's mother and father both being economists shaped his early thinking as an economist? How did Larry's parenting teach his children economics at an early age? What does Larry know now that he wishes he had known when he entered the workforce? 2. How to Get the US Out of Debt: What would Larry do to save the US economy today? What can be done to increase revenues for the US economy? Why does Larry believe carried interest should be taxed as income tax? Why does Larry believe we need more billionaires? How would he tax them more efficiently? Why does Larry believe cutting taxes is indefensible? What can be done to reduce inflation without massively hurting the poorest in society? 3. The World Around Us: What does Larry mean when he says, "Europe is a museum, China is a jail and Bitcoin is an experiement"? Why does Larry believe the next 5 years will be difficult for China? Why does Larry believe the next 5 years will be challenging for Europe? Which nation is Larry most confident about when projecting forward for the next 5-10 years? 4. Politics and a Trump Administration: How does Larry reflect on the role of Biden on the US economy and state of inflation? Would a Trump administration be better or worse for the US economy? What are the chances of Trump beating Biden in the next election? What would Larry most like to change about the US political system?

Orlando Bravo is a Founder and Managing Partner of Thoma Bravo. He led Thoma Bravo’s early entry into software buyouts and built the firm into one of the top private equity firms in the world.  Tobi Lütke is the CEO and Co-Founder of Shopify, the powerhouse company allowing anyone to start and grow their e-commerce business. Dara Khosrowshahi is the CEO of Uber, where he has managed the company’s business in more than 70 countries around the world since 2017. Parker Conrad is the Founder & CEO @ Rippling, the company that lets you easily manage your employees’ payroll, benefits, expenses, devices, apps & more—in one place. Jamie Siminoff is the Founder and Chief Inventor @ Ring, with Ring Jamie, created the world’s first Wi-Fi video doorbell while working in his garage in 2011. The company sold to Amazon for $1BN. Martín Escobari is Co-President, Managing Director and Head of General Atlantic’s business in Latin America. Martín is Chairman of the firm’s Investment Committee and also serves on the Management and Portfolio Committees. Ariel Cohen is the Co-Founder and CEO @ Navan (formerly TripActions), the #1 travel management super-app used by over 8,000 companies. Tarek Mansour is the Founder and CEO @ Kalshi, the first regulated exchange where you can trade directly on the outcome of events. Brian Armstrong is the Co-Founder and CEO @ Coinbase, the easiest place to buy and sell cryptocurrency. Over the last 10 years, Brian has led Coinbase to today, a public company with over 3,500 employees and revenues of over $7.5BN in 2021. Question of the Day: What are the world's tech leaders running from?

Rich Liu is the CRO @ Everlaw and a unicorn GTM exec having scaled five multi-billion dollar tech unicorns across two IPOs, a successful acquisition, and numerous funding rounds. Prior to Everlaw, Rich architected the GTM motions for companies like Navan (TripActions), MuleSoft, and Meta (Facebook). As a result of his incredible success, Rich has been recognized as a 2021 Top 100 Global Sales Leader. In Today's Episode with Rich Liu We Discuss: 1. Entry into the World of Sales: How Rich made his way from biochemistry into the world of sales? What is 1 takeaway from his time at Navan, Meta and Mulesoft that has shaped how he thinks about sales today? What does Rich know now that he wishes he had known when he entered the world of sales? 2. Sales Today: What is Happening? What are the biggest sales leaders saying today about price sensitivity and deal cycles? What has changed in the way companies buy software with the macro downturn? What do companies need to do to get deals over the line today? How do startups need to change the way they message to enterprises in order to sell today? How has the renewals process changed? What does this mean for customer success teams today? 3. PLG vs Enterprise: When and How? Is it possible to do both PLG and enterprise at the same time? Is it easier to start with enterprise and move to PLG or visa versa? How does the type of sales leader you need change dependent on the motion? When is the right time to move from founder-led sales to sales team? How does one know whether to hire a junior jack of all trades or a senior sales leader? 4. How To Hire The Best in Sales: How does Rich structure the hiring process for all new reps today? Does he use case studies to determine their depth and ability? Is the case study of the company they are interviewing at or a fresh company? What questions does Rich ask every candidate for a new role? What are some of the biggest red and green flags in how candidates talk in interviews?

TJ Parker is the co-founder and former CEO of PillPack. TJ Raised over $100M in financing, grew the company to more than 1k employees, and successfully sold the business to Amazon for $1B in 2018. As of last week, TJ was announced as the newest Partner @ Matrix Partners where he will initially focus on health opportunities from concept to series A. In Today's Episode with TJ Parker We Discuss: 1.) From Growing Up in Pharmacies to Selling to Amazon for $1BN: How did TJ seeing the pharmacy industry from his parents lead him to believe there was a $BN company to be built in the space? What does TJ know now that he wishes he had known when he started the company? What does TJ believe he is running from? How does that impact his own style of parenting? 2.) The Truth About Entrepreneurship: Why do the best founders have to get comfortable in an environment of uncertainty? What have been some of TJ's biggest lessons in how to do this? Why does TJ believe the role of the CEO is to set the vision and get out of the way? What roles can only the CEO do? How does TJ approach delegation? What have been some of his core lessons? Does TJ believe being naive is a superpower when starting a company? What do founders need to know vs what do they not need to know when starting a business? 3.) Speed of Execution and Decision-Making: How important does TJ believe speed of execution is for startups today? What can founders do to create a culture of rapid decision-making? What works? What does not? What does TJ believe are 1-2 of the single best and worst decisions he made with PillPack? What are some of the biggest mistakes TJ sees founders make both in speed of execution and then also in decision-making processes? 4.) The Crucible Moments: Lawsuits & Acquisitions: How did an incumbent come days away from shutting down PillPack? How did they save the company? How does TJ deal with those moments of intense stress? How did the Amazon acquisition come to be? Why and how did the prior acquisition fall through? Does TJ regret the sale to Amazon? How was life at Amazon post-acquisition?

One of the core questions in AI and investing today; who wins, startups or incumbents? Startups have speed and innovation but incumbents have scale, resources, and distribution? Today we hear from 6 leading investors and founders discussing where they place their bets who has the advantage; startups or incumbents? Emad Mostaque is CEO @ StabilityAI, the parent company of Stable Diffusion. To date, Emad has raised over $110M with Stability with the latest round reportedly pricing the company at $4BN.  Yann LeCun is VP & Chief AI Scientist at Meta and Professor at NYU. He was the founding Director of FAIR and of the NYU Center for Data Science. Clem Delangue is the Co-Founder and CEO @ Hugging Face, the AI community building the future. Clem has raised over $160M from the likes of Sequoia, Coatue, Addition and Lux Capital to name a few. Sarah Guo is the Founding Partner @ Conviction Capital, a $100M first fund purpose-built to serve “Software 3.0” companies. Prior to founding Conviction, Sarah was a General Partner at Greylock. Vince Hankes is a Partner @ Thrive Capital where he has led the firm’s investments in OpenAI, Melio, and Airplane.dev. Prior to Thrive, Vince learned the craft of venture from Lee Fixel @ Tiger. Tomasz Tunguz is the Founder and General Partner @ Theory Ventures, a $230M fund that invests $1-25m in companies that leverage technology discontinuities into go-to-market advantages. The Question of the Day: Who wins? Startups or Incumbents?

David Alleman is the Co-Founder and Co-Chairman @ On Running one of the fastest-growing global sports brands with over 17 million products sold in 60+ countries. In 2021, On went public on the NASDAQ and today has a market cap of $8.7BN. However, it all started with three friends in the mountains experimenting with making shoes with pieces of garden hose to create a running shoe with a totally different feel. In Today's Episode with David Alleman We Discuss: 1. From the Swiss Mountains to NASDAQ IPO: What was the initial a-ha moment for David and his co-founders with On Running? How did they make the first shoes? What are some of the biggest lessons for David in V1 product build? What does David know now that he wishes he had known at the start? Is naivete always good? 2. The Launch: First Customers: How did On get their first customers? What can products and companies do to instill true customer love in those first customers? What was the hardest element of launching On to their first customers? How does David analyze and use customer feedback? What does he listen to vs not? 3. Retail: Expanding into Own Store vs Partnerships: What are some of David's biggest lessons in how to make retail partnerships successful? How can brands create amazing experiences for customers in retailers that are not their own? Why did On decide to also have their own stores? How did this change the business? What have been David's biggest learnings on what it takes to do retail well with own stores? 4. Roger Federer: Working with a Legend: How did the relationship with Roger begin? Where was the first meeting? What was it like? How did Roger come to invest in On Running? Why did On not want to do the traditional athlete endorsement deal? What role does Roger play in the company today? How does he impact product development? What have been some of the biggest lessons for David from working with Roger? How much of an impact has Roger had on On Running as a business? 5. Financing, IPOs, and Brand: Does David wish they had raised venture capital sooner? If they had more money sooner in their journey, what would David have invested in earlier? Why did they decide to go public when they did? How has the journey been post being a public company? What changes? What is the same? What brand does Davist most respect and admire? Why? What brand decisions does David most regret? What would he have done differently?

Adam Besvinick is the Founder of Looking Glass Capital, a pre-seed-focused firm started in 2020. Before starting Looking Glass, Adam spent about 5 years at Deep Fork Capital and Anchorage Capital Group investing in pre-seed through Series C. Adam's portfolio across funds includes the likes of BigID, Transfix, NomNom, and Hone Health, to name a few.  In Today's Episode with Adam Besvinick We Discuss: 1. How Twitter Led to Founding a Venture Firm: How did Adam make his way into the world of venture through Twitter? What are 1-2 of his biggest lessons from working with the legend, Chris Sacca? What does Adam know now that he wishes he had known at the beginning of his time in VC? What do most young VCs misunderstand when it comes to reputation? 2. Raising Fund I: The Process: How many LP meetings did Adam have to close Fund I? What docs and materials did he have for the fundraise? How does he advise other managers on doing docs for fundraises? How do different LP profiles want different things in the managers they work with? How did Adam approach first vs final close? How does he advise others managers on closing? How did Adam instil a sense of urgency in LPs to move and commit to the fund? What are 1-2 of Adam's biggest pieces of advice to managers raising a first-time fund? 3. Looking Glass: The Very Disciplined Pre-Seed Strategy: How did Adam decide on the fund size? Why is it the optimal fund size? What is the desired ownership for Adam? What level of dilution does he expect across the lifecycle of the company? What is the average check size? What is the average entry price? How does Adam approach reserves and follow-on checks? How does Adam reflect on his own relationship to price? Why does Adam not like the majority of pre-seed micro-fund strategies? 4. The Market: Multi-Stage Firms Destroying Seed Does Adam agree that "multi-stage firms have destroyed seed rounds"? How does Adam advise founders when they have multi-stage offers and seed firm offers? Who will be the winners and losers in the next 10 years of venture? Why is it harder than ever to advise founders on fundraising rounds today?

Tomer Cohen is the CPO @ Linkedin. Since joining in 2012, Tomer has served in key leadership roles, helping launch and scale new innovative member and customer experiences. He previously led the growth and development of LinkedIn’s Marketing Solutions portfolio and LinkedIn's consumer and mobile products. Prior to LinkedIn, Tomer worked as an entrepreneur with Greylock Partners and founded a company in the personal CRM space. In Today's Episode with Tomer Cohen We Discuss: 1.) From Israeli Military and Chip Design to CPO @ Linkedin: How did Tomer make his way from the Israeli military to being CPO @ Linkedin? What does Tomer know now that he wishes he had known when he became CPO? What have been some of his biggest lessons from working with Reid Hoffman? 2.) Product: Art or Science: How does Tomer determine whether product is art or science? If he were to put a number on it, what would it be? How does Tomer determine whether to go with his gut vs go with the data on product decisions? How is AI changing the role of product managers and product leaders? What do product leaders and PMs need to do to stay up to date with the latest changes in AI? 3.) Linkedin: Review of Current Products: Feed, Stories, Messenger How does Tomer analyse the success of "the feed" in Linkedin? What worked? What did not work? Why did "Stories" not work in Linkedin? What went wrong? What did they learn? What is Tomer doing to tackle the spam issue in Linkedin? What are the biggest challenges associated? Why does Linkedin still have such poor messaging service? Why is it a difficult problem to solve for? 4.) AI Changes Everything: Why does Tomer believe this wave of AI is the most significant technological shift in our lifetime? Who will win the race in AI; startups or incumbents? Which model will work most efficiently; open or closed? Will we see large enterprises prefer bundled AI options or unbundled with specialised providers?

Guy Podjarny is the Founder of Snyk, the leading Developer Security platform, helping developers secure as they build. Guy was previously CTO at Akamai, co-founded Blaze.io (acquired by Akamai), and was the product manager of AppScan, the first AppSec scanner, through Sanctum, Watchfire and IBM. Guy is a public speaker, O’Reilly author, and an active early stage angel investor. In Today's Episode with Guy Podjarny We Discuss: 1.) From Israeli Military to Founding a $10BN Company: How Guy made his way into the world of startups from the Israeli military? What is Guy running away from? Why does he hate tribalism so much? Does Guy believe serial entrepreneurship is valuable or naivety of young founders is good? 2.) The Secret to Finding Product Market Fit: Why does Guy believe PMF is a poorly defined term? How does Guy define PMF? What are the single biggest mistakes founders make while searching for PMF? What are the most important elements on messaging when it comes to PMF? If you have a horizontal tool, how do you message and resonate with specific audiences? 3.) Defensibility and Being First to Market: Does Guy believe that being the first to market is really that valuable? Does Guy agree that investors expecting defensibility on day 1 is wrong? Why does Guy think market leadership is way more important than first to market? What are the true defensible moats that can be built early today? 4.) Lessons from 100 Angel Investments: What have been the single biggest lessons for Guy from his 100 angel investments? What are the biggest mistakes angels make when investing today? How should founders present their market size to investors? Where do they go wrong? Does Guy invest in both painkiller and vitamin businesses? How does he compare them? Why is Boldstart Guy's favorite venture capital firm?

Nico Wittenborn is the Founder of Adjacent, one of the best early-stage firms created over the last 5 years. Before starting Adjacent, Nico spent over 3 years at Insight Partners in New York and before that learned the craft of venture from some of the best in early-stage, Point Nine, where he spent over 4 years. Nico's portfolio across funds includes the likes of Revolut, Chainalysis, Oura, RevenueCat and PhotoRoom to name a few. In Today's Show with Nico Wittenborn We Discuss: 1.) From Selling Mobile Phones to Leading Early-Stage Investor: How did Nico first make his way into the world of venture with Point Nine? What did Nico learn from his time with Point Nine and Insight? How did his time at each impact how he invests and runs Adjacent today? What does Nico know now that he wishes he had known when he started investing? 2.) Is Consumer Subscription Even a Good Place to Invest? With Calm ($2BN) and Duolingo ($6BN) as the market leaders and there only being two of them, is consumer subscription even a good place to invest? How does Nico pushback that retention for consumer subscription apps is so bad? What do many not see about consumer subscription retention numbers? How does Nico respond to the challenge of high customer acquisition cost and navigating challenging platform shifts in advertising, when investing in consumer subscription? What will the consumer subscription landscape look like in 5 years time? 3.) Adjacent: The Fund, The Strategy: Why does Nico believe if your fund model relies on $10BN outcomes, you are in trouble? How large is the latest Adjacent fund? What does the portfolio construction look like for the fund? How much diversification is the right level of diversification? How many companies per fund? How does Nico think about capital concentration on a per company basis? What are Nico's ownership requirements? How have they changed with funds? What is it about Nico's structure which enables him to be more collaborative than others? 4.) Nico: The Investor: Lessons: How does Nico reflect on his own relationship to price? When does he pay up? When does he not? What has been one of Nico's biggest misses? How has that changed his approach? Why does Nico not really compete with the large multi-stage funds? Why is Nico deliberately trying to reduce the amount of companies that he sees? 5.) The Future of Venture: How does Nico analyze the rise of solo GPs? What are the biggest pros and cons of the model? Why does Nico believe the large generalist funds are in trouble? Who is set to win and who is set to lose in the next 10 years of venture? Which seed firm would Nico invest in? Which Series A firm? Which growth firm?

Ryan Wiggins is the VP of Growth and Analytics at Mercury where he oversees a Growth team and founded the Analytics function. Prior to this, Ryan built Growth teams at WhatsApp, where he helped grow WhatsApp Business from 0->100M users, Workplace, and Facebook Ads. If that was not enough, Ryan is also an active angel investor. In Today's Episode with Ryan Wiggins We Discuss: 1.) From US Department of Commerce to Leading Growth Teams: How Ryan made his initial foray into the world of growth with Facebook and Whatsapp? What does Ryan know now that he wishes he had known when he made the entry into growth? What advice does Ryan have for people who want to change their career but are not sure what they want to do? 2. ) Who and When: Building the Team: Should we hire a Head of Growth or a more junior growth hire first? What are the different profiles of growth hires? How do they change with business model? When is the right time to hire your first growth hire? What are the single biggest mistakes founders make on the timing of growth hires? 3.) How to Hire: The Process: Structurally, what is the right way to hire for a growth team? What does the interview process look like? What do you want to get out of each meeting? Should case studies be used, if so, should they be used for the company hiring or of the company where the candidate is from? What does the comp package look like for different growth hires? Who should be brought into the growth hiring process? What stage should they be involved? 4.) Onboarding: Setting Growth Up for Success: What is the ideal first 30,60 and 90 days for new growth hires? What can leaders do to ensure they are set up for the maximum chance of success? What are three of the biggest red flags bad growth hires show in the first 30 days? What are the biggest mistakes founders make in the onboarding process of growth hires?

Emad Mostaque is the Co-Founder and CEO @ StabilityAI, the parent company of Stable Diffusion. Stability are building the foundation to activate humanity's potential. To date, Emad has raised over $110M with Stability with the latest round reportedly pricing the company at $4BN. Investors include Coatue, Lightspeed, Sound Ventures, OSS Capital and Airstreet Capital, to name a few. Prior to Stability, Emad was in the world of hedge funds, that was until his son was diagnosed with autism and he left to make a difference in the space and help find treatments and solutions. In Today's Episode with Emad Mostaque We Discuss: 1.) From Hedge Funds to Finding Treatments for Autism to Leading the World of AI: How Emad made his way from the world of hedge funds to founding one of the leading AI companies of our time? How did Emad find a solution to parts of his son's autism with a $6 drug? How does Emad believe we can use AI to solve the majority of medical problems today? What does the future of healthcare look like with AI at the centre? 2.) Models: What is Real? What is False? Why no models today will be used in a year? Why all models are biased and how do we solve for it? Why hallucinations are a feature and not a bug? Why the size of your model does not matter anymore? Why will there be national models specified to cultures and nations? How is this implemented? 3.) Who Wins: Startups or Incumbents: Why does Emad believe there will only be 5 really important AI companies? Which will they be? How does Emad review Google's AI strategy following their news last week? Was their integration of Google and Deepmind recently a success? How does Emad assess Meta's AI strategy? Why does Zuckerberg now acknowledge the metaverse play was a mistake? How does Emad evaluate the approach taken by Amazon? Why are they the dark horse in the race? What can startups do to get a meaningful edge on the large incumbents? How do they compete with their distribution? 4.) The Next 12 Months: What Happens: Why does Emad believe the .ai bubble will be bigger than the dot com bubble? Why does Emad believe that the biggest companies built-in AI in the next 12 months will be services-based companies? How does the ecosystem look if this is the case? Why will India and emerging markets embrace AI faster than anyone else? What happens to economies that have large segments reliant on freelance work that AI replaces? Why will we see the death of many large content publishers and media companies? What does Emad mean when he says we will see the rise of "AI first publishers"? 5.) Open or Closed: What Wins: Why does Emad believe we must be open by default? Why does open win? Why does Emad side with Elon and believe we must pause the development of AI for 6 months? How does Emad evaluate the leaked memo from Google stating that neither Google nor OpenAI are ahead? What does this mean for the AI ecosystem? Where will the best AI talent concentrate? What do companies need to do to win the best talent?

Yann LeCun is VP & Chief AI Scientist at Meta and Silver Professor at NYU affiliated with the Courant Institute of Mathematical Sciences & the Center for Data Science. He was the founding Director of FAIR and of the NYU Center for Data Science. After a postdoc in Toronto he joined AT&T Bell Labs in 1988, and AT&T Labs in 1996 as Head of Image Processing Research. He joined NYU as a professor in 2003 and Meta/Facebook in 2013. He is the recipient of the 2018 ACM Turing Award for "conceptual and engineering breakthroughs that have made deep neural networks a critical component of computing". Huge thanks to David Marcus for helping to make this happen. In Today's Episode with Yann LeCun: 1.) The Road to AI OG: How did Yann first hear about machine learning and make his foray into the world of AI? For 10 years plus, machine learning was in the shadows, how did Yan not get discouraged when the world did not appreciate the power of AI and ML? What does Yann know now that he wishes he had known when he started his career in machine learning? 2.) The Next Five Years of AI: Hope or Horror: Why does Yann believe it is nonsense that AI is dangerous? Why does Yann think it is crazy to assume that AI will even want to dominate humans? Why does Yann believe digital assistants will rule the world? If digital assistants do rule the world, what interface wins? Search? Chat? What happens to Google when digital assistants rule the world? 3.) Will Anyone Have Jobs in a World of AI: From speaking to many economists, why does Yann state "no economist thinks AI will replace jobs"? What jobs does Yann expect to be created in the next generation of the AI economy? What jobs does Yann believe are under more immediate threat/impact? Why does Yann expect the speed of transition to be much slower than people anticipate? Why does Yann believe Elon Musk is wrong to ask for the pausing of AI developments? 4.) Open or Closed: Who Wins: Why does Yann know that the open model will beat the closed model? Why is it superior for knowledge gathering and idea generation? What are some core historical precedents that have proved this to be true? What did Yann make of the leaked Google Memo last week? 5.) Startup vs Incumbent: Who Wins: Who does Yann believe will win the next 5 years of AI; startups or incumbents? How important are large models to winning in the next 12 months? In what ways does regulation and legal stop incumbents? How has he seen this at Meta? Has his role at Meta ever stopped him from being impartial? How does Yan deal with that?

Clem Delangue is the Co-Founder and CEO @ Hugging Face, the AI community building the future. To date, Clem has raised over $160M from the likes of Sequoia, Coatue, Addition and Lux Capital to name a few. Prior to Hugging Face, Clem was in product and marketing at two different startups both of which were acquired. In Today's Episode with Clem Delangue: 1. From Tamagotchi to Leading the World of AI: How did a Tamagotchi startup turn into one of the hottest AI startups in the world? What does Clem know now that he wishes he had known when he started? What are Clem's biggest pieces of advice to founders on pivoting? 2. AI: Trend or Transformation: To what extent does Clem believe the current hype in AI is justified? What is overblown? What have been some true and groundbreaking developments? How far away does Clem believe AGI is? What is a massive misconception the public has that Clem wishes he could change? 3. Open vs Closed: Which Model Wins: Why does Clem believe the future of AI will be won by open-source? What is his reasoning to suggest closed is fundamentally a weaker model? Does Clem acknowledge that in the short term, enterprises will buy from a closed model with greater ease? How does he plan to tackle this? 4. Regulation: What Happens Now: What regulatory changes need to be made in the world of AI most urgently? Is Elon Musk right to suggest the immediate pausing of developments in AI? What does Clem believe to be the most likely scenario to AI regulation in the next 12 months? 5. Fundraising: Lessons and Reflection on Raising $160M: Do AI startups fundamentally cost more money than normal startups to build? Why does Clem not meet investors in between rounds? What does Clem believe is the most helpful thing an investor can do? What are Clem's spiciest takes on venture as a financing model?

Today's 20Sales is a special Mother's Day edition where we are joined by 6 of the best sales leaders who also happen to be rockstar mothers. The Profiles Maggie Hott is on the GTM Team (Go-To-Market) at OpenAI. Before OpenAI, Maggie was Director of Sales @ Webflow and before Webflow spent an incredible 6 years at Slack. Stevie Case is the CRO @ Vanta. Prior to Vanta, Stevie spent an immensely successful 6 years at Twilio as VP of Mid-Market Sales. Renu Gupta is an advisor and sales consultant to some of the fastest-growing SaaS companies today. Previously she has held sales leadership roles at Slack, Thrive and Dropbox. Lauren Schwartz is the VP Enterprise Sales @ Fivetran. Before Fivetran, Lauren spent 4 years at Segment as Senior Director of Enterprise Sales leading to their acquisition by Twilio. Julie Maresca is the Head of Global Accounts at Atlassian. Prior to Atlassian, Julie spent an immensely successful 6 years at Slack in numerous roles including Head of Enterprise Sales for North America. Jessica Arnold is the VP of Global Sales Development @ Amplitude. Before Amplitude, Jessica was the Senior Director for Inside Sales North America at Dropbox for close to 6 years. In Today's 20Sales Mothers Day Episode We Discuss: 1.) How have you navigated growing in your career at the same time, growing your family? 2.) How do you balance your career and being a mother - when do you lean in and out? 3.) What are some specific strategies or tools that have helped you maintain a work-life balance?  4.) How do you prioritize your mental health and wellbeing while juggling your responsibilities at work and at home? 5.) How do you handle the guilt that many working mothers experience when they have to focus on their career? 6.) What are the unique challenges and advantages of being a mother in a sales leadership role? 7.) How has your experience as a mother influenced your leadership style and decision-making? 8.) How have you navigated going out on maternity leave without it having an impact on your career? 9.) America has one of the worst parental leaves of any country in the world. How can you advocate for parental leave if the existing policy isn’t up to par? 10.) What are some ways that companies can create a more inclusive and supportive environment for working mothers in sales leadership roles?

Chris Paik is a General Partner @ Pace Capital, an early-stage venture firm in NYC. Pace's first fund was $150M and their second was $250M. Before co-founding Pace, Chris was a General Partner at Thrive Capital where he spent an incredible 8 years having joined the firm when they were on their first $10M Fund. In Today's Episode with Chris Paik We Discuss: 1. From Hipster to One of NYC's Best VCs: How Chris made his way from not knowing about venture capital to being one of the most prominent in NYC? What are 1-2 of his biggest takeaways from his 8 years at Thrive? How did they impact how he thinks about building Pace today? What are Chris' biggest lessons from working with Josh Kushner? What did Josh do to spot young talent in a way like no one else did? 2. The Core Pillars of Successful Venture Investing: "Invest in companies that can be described in a single sentence". What does Chris mean by this? How does that impact the type of companies he looks to invest in? "Business Model Fit is as important as PMF". What does Chris mean by this? How does he determine where a company has business model fit? How does Chris analyze his relationship to market sizing? How does Chris think about how willing he is to take a bet on market timing? Why does Chris believe that the more "virtuous" a company is, the less enterprise value it will have? 3. What is Wrong with Venture Capital: The Misalignments: What does Chris believe are the single biggest misalignments between VCs and Founders? What does Chris see as the biggest misalignments between VCs and LPs? Why does Chris believe we should scrap capital gains tax and all be taxed as an income tax? Why do acquisitions allow investors to be screwed over by the acquiring company? 4. The Future of Social and User Generated Content Platforms: How does Chris analyze consumer businesses according to "The Seven Deadly Sins"? Why does he call them, "The Seven Deadly Motivators"? What does Chris believe is the future for Substack? Why does it not have Business Model Fit? What are 1-2 of his biggest lessons from being on the Twitch board? How did that experience impact his mindset and approach to what good is in UGC and social? What does Chris believe is the number one thing to look for in a potential consumer social investment? What do so many miss?

Alex Rodriguez is a businessman and the Chairman and Chief Executive Officer of A-Rod Corp, a broad-based investment firm that bets on world-class startups and partners with leading global companies across the real estate, health and wellness, technology, and sports & entertainment industries. While best known as one of the world’s greatest athletes (a 14x MLB All-Star and a 2009 World Series Champion with the New York Yankees), for more than 25 years, Alex leads a team of experts building high-growth businesses and is co-owner of the Minnesota Timberwolves. In Today's Episode with Alex Rodriguez 1.) From MLB to Business MVP: How Alex made his transition from one of the world's greatest athletes to the world of business? What does Alex know now that he wishes he had known at the start of his business career? What is Alex running away from? How do his insecurities drive him? 2.) Lessons from Magic Johnson and Warren Buffet: What are some of the single biggest lessons Alex has learned from his time with Warren Buffet? How did Magic Johnson impact Alex's approach to business? What is Magic Johnson's framework? How can others use it as a blueprint for their career? 3.) Alex Rodriguez: The Business Builder and Investor: What has been Alex's single biggest investing hit? What did he learn from it? What has been Alex's single worst investment decision? How did that change his approach? Why is Alex not buying real estate currently? How does he view the future of real estate buying? 4.) Alex Rodriguez: The Father and Son: How did having two daughters impact Alex's approach to business and life? What have been Alex's single biggest lessons from seeing his single mother operate? How does Alex reflect on his own relationship to money? How has it changed?

Vince Hankes is a Partner @ Thrive Capital where he has led the firm’s investments in OpenAI, Melio, and Airplane.dev. He currently sits on the board of Airtable, Benchling, Lattice, and Melio. Prior to joining Thrive, Vince was an investor at Tiger Global where he learned the craft of venture from the legend that is Lee Fixel. In Today's Episode with Vince Hankes We Discuss: 1. From Tiger Global to Partner @ Thrive Capital: How Vince made his way into the world of investing with Tiger Global? What are 1-2 of his biggest takeaways from working alongside the legendary Lee Fixel? Why did Vince make the move from Tiger to Thrive? How do the two firms differ? 2. The OpenAI Investment: The Memo: How did the OpenAI deal come to be? What were the round dynamics? Market Evaluation: How did Vince and the team analyze the market top down? Competition: Who did Vince identify as the core competitors to OpenAI? Defensibility: How did Vince think through the long-term defensibility of OpenAI's model? Does Vince believe these models will become commoditised? Price: How did Vince and the team get comfortable with the $29BN price? 3. AI: Hype or Generational Defining Transformation: Trend or Transformation: Why does Vince believe AI will be the defining technology of our generation? Startup vs Incumbent: Does Vince think the value will accrue to the incumbent or the startup? Open or Closed: Does Vince think we will operate in a closed (one model rules them all) environment or an open-source environment with many models? AI Talent: Where does Vince think the majority of the best AI talent will concentrate? Speed: Why would Vince be scared if he were a startup today looking at the incumbents? 4. The Changing Investor: Lessons from Good and Bad: How has Vince changed most significantly as an investor over time? What has been his single biggest investing mistake? How did he learn from it? What has been his biggest investing success? How did that change his mindset? What has Thrive done in their org structure to allow them to make bets very few other firms can do?

Mark Carney is the Vice Chair and Head of Transition Investing @ Brookfield Asset Management, one of the world's leading asset managers with over $800BN in AUM. Mark is also United Nations Special Envoy on Climate Action and Finance. He has also served as Finance Advisor to the British Prime Minister. In addition to this, Mark is on the board of Stripe, PIMCO and The World Economic Forum. In a previous life, Mark spent over a decade as a Central Banker, most recently as Governor of The Bank of England and before that as Governor of The Bank of Canada. In Today's Episode with Mark Carney We Discuss: 1. Is The Banking Crisis Over? What Happened? Why does Mark not believe we are in a banking crisis? Why does he not believe the banking turmoil is over? Was SVB the fault of regulatory mistakes or management mistakes? Is FRB a damaged asset in it's own right or the result of contagion within the banking ecosystem? 2. The Impact of the Banking Turmoil: What Happens Now? What does Mark believe is the future of regional banks? Why does Mark believe we will see massive consolidation in banks coming soon? Should the Fed be guaranteeing all deposits automatically? 3. What Happens To The Macro Now? How does the banking turmoil impact growth rates? Will we definitely go into a recession now? What is the impact on monetary policy? Can the Fed raise rates even higher? What does this mean for the future of money? Why is it a silver bullet for stablecoins? If Mark could bet on China or the US for the next 10 years, who would it be? Does Mark believe the UK is in a weaker situation than ever? What about Europe? 4. The Future of Climate and Net Zero: Where are we at with Net Zero? Are we ever going to make progress? Is it possible to make progress without the cooperation of China? Why does Mark disagree and suggest China has done more than most to help the climate? Who is talking more than they are acting in the fight to save the climate? On the flip side, who is acting more than they are talking?

Sarah Guo is the Founding Partner @ Conviction Capital, a $100M first fund purpose-built to serve “Software 3.0” companies. Prior to founding Conviction, Sarah was a General Partner at Greylock where she made investments in the likes of Figma, Coda, Neeva and many more incredible companies. Sarah also hosts her own podcast, No Priors with the wonderful Elad Gil. In Today's Episode with Sarah Guo We Discuss: 1. From Large Multi-Stage Firm to Founding Conviction: Why did Sarah decide to leave Greylock? What are 1-2 of her biggest lessons from her time at Greylock? How did they impact her mindset when building Conviction today? What does Sarah believe are the most surprising or hardest elements of firm building? 2. The Future for AI: The Opportunities and the Challenges: Why does Sarah believe AI is the most foundational technology of our lifetime? Why did Sarah decide to centre the entire fund around AI? Is AI not an enabling technology that will power all sectors in technology? Is Sarah concerned by the further wealth inequality that AI and billion dollar companies created by 10 people, will inevitably bring? How does Sarah think about the potential for malicious AI use? What can be done to prevent this? 3. Startup and VC Principles That Are BS: Why does Sarah believe that defensibility is BS? Why do Sarah and Harry both believe that reserves in venture funds are a suboptimal use of funds? "Great founder, bad market, market wins". Does Sarah agree? How does Sarah prioritize the centrality of founder vs market? 4. Sarah Guo: The Investor How has Sarah changed most significantly as an investor over the last 5 years? What is Sarah's biggest miss? How did it impact her mindset today? What is Sarah's biggest win? How did that alter her risk appetite? How does Sarah see the future of venture? If Sarah could invest in one multi-stage firm and one seed-stage firm, which would it be?  

Jack Brody is the VP Product @ Snap. Jack joined Snap in 2014 as a Product Designer, and ultimately helped build out the design organization as the Head of Design before taking on his current role overseeing all of Product for the Snapchat application and Hardware. In his 9 years at Snap, he helped create Memories, the Snap Map, and AR Lenses like Face Swap. In Today's Episode with Jack Brody We Discuss: The Shortest Internship in Tech: How did Jack get an internship with Evan Spiegel and Snap while he was still at college? How did it turn into the shortest internship in tech history? What are the single biggest product lessons Jack has from working with Evan Spiegel? 2. Product 101: Art vs Science: Does Jack believe product is more art or science? If he were to assign numbers to them, what would they be? How does Jack define creativity? What can founders and product leaders do to ensure their teams are as creative as possible? What is the 3 step framework through which product leaders should prioritize product ideas? Does Jack believe that when the CEO is no longer the Head of Product, the company is dead? Does Jack agree with Gustav Soderstrom, "talk is cheap, so we should do more of it"? 3. The SNAP Hiring Process: What Works and What Does Not: What is the hiring process for the product team at SNAP? What questions are most revealing of 10x product people in the interview process? What case studies and tests does Jack use in the interview process? What other roles and functions does Jack bring into the interview process as part of the decision? What are the single biggest mistakes founders make in the hiring process for product? 4. SNAP, The Future, and The World Around Us: What do Jack and SNAP believe will be the future for augmented reality? What country is SNAP not big in today but will be in the next 5 years? Why that one? Why did SNAP tear down its android app and start again? What has been the impact? Were the SNAP glasses a success? What is their future?  

Avlok Kohli is the CEO @ AngelList. Under his leadership, Avlok has taken AngelList from an SPV provider to a company that is becoming the software platform for the entire industry. Today, AngelList supports over $15BN in assets and 40% of US unicorns have had a GP invest in them through AngelList. Prior to becoming CEO @ AngelList, Avlok founded 3 companies, all of which were acquired including by the likes of Square and eBay. In Today's Episode with Avlok Kohli We Discuss: 1. From 3x Founder to Scaling AngelList to $15BN in AUM: How did Naval convince Avlok to join AngelList and be CEO? Does Avlok believe in startups having defensibility in the early days? How important does Avlok believe it is for companies to be "first to market"? Why does Avlok believe all the last-mile grocery delivery companies will go bust in the downturn? 2. What is Going On in Venture: New Funds, LPs, Secondaries: Are we seeing the amount of net new funds reduce in the downturn? Are we seeing the size of new funds being raised, being smaller? Is the time to first close increasing in time? Does AVlok agree that the fund segment hit hardest by the downturn is micro fund managers? Which LP class has pulled back from fund investing most significantly? Why does Avlok believe institutions have returned to fund investing more than ever right now? Are we seeing an increase in fund secondary positions? 3. What is Going on in Startups: Rounds, Valuations, Party Rounds Are we seeing the number of startups able to close their round reduce? Are we seeing the size of startup funding rounds reduce? How does this depend on the stage? What are we seeing for startup valuations? Why is seed as high as ever? What is the most hit? How is the composition of funding rounds changing? More or fewer party rounds? When does Avlok believe we will see down rounds and pay-to-play, really come into effect? 4. The Business of AngelList and its Future: What are the margins on AngelList products today? What is the best margin AngelList product? What is the worst? What product did AngelList do that in hindsight, Avlok wishes they had not done? Why did AngelList back out of Europe? Was it a mistake? How does Avlok think about AngelList's fierce competition with Carta today?

Tomasz Tunguz is the Founder and General Partner @ Theory Ventures, just announced last week, Theory is a $230M fund that invests $1-25m in early-stage companies that leverage technology discontinuities into go-to-market advantages. Prior to founding Theory, Tom spent 14 years at Redpoint as a General Partner where he made investments in the likes of Looker, Expensify, Monte Carlo, Dune Analytics, and Kustomer to name a few. Tom also writes one of the best blogs and newsletters in the business which can be found here. In Today's Episode with Tomasz Tunguz We Discuss: Founding a Firm: The Start of Theory: Why did Tom decide to leave Redpoint after 14 years to found Theory? What are 1-2 of his biggest lessons from Redpoint that he has taken with him to his building of Theory? What does Tom know now that he wishes he had known when he started investing? 2. From 150 LP Meetings to Closing $230M: Raising a Fund I How would Tom describe the fundraising process? How many meetings with LPs did he have? How many did he know previously? What documents did he share with LPs? Did he have a dataroom? How did he use it? How did Tom create a sense of urgency to compel LPs to come into the fund? How does Tom feel about the debate between one close and multiple closes? What was the #1 reason LPs said no to investing? What worked and Tom would do again for the next raise? What did not work and he would change for the next raise? 3. Where Will Value Accrue in the Next Decade of AI: Startup vs Incumbent: Will incumbents embrace AI before startups are able to acquire distribution? Infrastructure vs Application Layer: Where will the majority of value accrue in the next decade; infrastructure or application layer? Bundled or Unbundled: Will bundled services be the dominant consumer and enterprise choice or will unbundled specialized solutions win? 4. AI and The World Around It: How does Tom believe AI could save the US economy? Why does Tom believe Google are the losers in the AI race? Which incumbents have responded best to AI? Why does Tom believe we will be in a worse macro place at the end of the year than we are now?

Mark Goldberger is Head of Enterprise Sales at Ramp, the fastest-growing corporate card and bill payment software in America, and recently named Most Innovative Company in North America by Fast Company. Prior to joining Ramp, Mark was the first enterprise rep at TripActions (now Navan), where he helped bring in more than $100m of ARR as an IC and sales leader. Before TripActions, Mark worked at Highfive, a video conferencing company since acquired by Dialpad. In Today's Episode with Mark Goldberger We Discuss: 1. From Wine Industry to Sales Leader: How Mark made his way into the world of enterprise sales having been in the wine industry? Mark sent out 100 CVs for his first sales role, why did they not respond? How should companies think differently about the people they hire? What could he have done better with the outreach? What does Mark know now that he wishes he had known when he entered the world of sales? 2. The Sales Playbook and Why You Should Never Hire a Sales VP First: Why does Mark believe that you should never hire a Sales VP as the first sales hire? What does Mark mean when he says product-customer-fit is more important than product-market-fit? Why does Mark believe that revenue does not matter with your first customers? If revenue does not matter, what should you be trying to get out of them? When should the founder handover sales to either a junior or more senior hire? 3. How to Hire 10x Sales Teams: The Process: How does Mark structure the process for hiring 10x sales reps? What questions are most revealing in identifying a 10x sales rep? How do they respond? Why does Mark want candidates to pitch his own product back to him? How does Mark make the hiring process more challenging to really test the quality of candidates? What is the core difference between losers and winners in sales? 4. Discounting, Champions, Creating Urgency: Why does Mark not like discounting? Where do many sales teams use it poorly? How does Mark like to create urgency in a sales process? What works? What does not? How can sales reps know whether they truly have a deal champion within a buyer? What is the right way for sales reps to ask to meet the exec buyer? When is the right time to ask to meet the exec buyer? What are some clear signs that you are not speaking to a decision-maker? 5. Building a High-Functioning Sales Org: What is the right way to do deal reviews? How often? Who should be invited? What is the right way to do sales onboarding for all new reps? Why is traditional outbound still the most important thing in a sales process? Why do so many people get pipeline qualification so wrong?

From college party promoter to managing global stars to CEO and investor. Scott “Scooter” Braun is one of the most powerful people in media and one of the most multi-faceted entrepreneurs we have ever met.  As the founder of media company SB Projects and the co-founder of TQ Ventures, he has backed prominent companies such as Pinterest, Spotify and Uber and managed some of the world’s biggest names in music including Justin Bieber, Ariana Grande, and Demi Lovato. Braun’s other accolades include founding Ithaca Ventures (acquired by HYBE for $1BN+) in 2021, and philanthropic efforts such as being a Make-A-Wish board member, raising $55M+ for Hurricane Harvey and Irma relief and continuing to instill the value of social good wherever possible.  In Today’s Episode with Scooter Braun We Discuss: 1. From College Party Promoter to Managing The World's Biggest Superstars: What was the single most catalytic moment of Scooter’s career? What was Scooter's most painful professional mistake, and what did he learn from it? What was the decision-making behind Scooter's HYBE deal? What is the biggest challenge in scaling the trajectories of the people Scooter works with? If Scooter could change one thing about the music industry, what would it be? 2. College Party Promoter Turned Venture Investor: How did Scooter originally get into investing? How did Scooter’s party promoting business almost lead to an early investment in Facebook? Do people approach Scooter differently as an investor because of his success in the music industry? Why is vulnerability helpful for investing? 3. Scooter's Lessons on Success (And How to Deal With It): Why does Scooter believe happiness and success are not aligned? How does Scooter approach deal-making? Is work-life balance bullshit? Does Scooter think you have to break your back to become as successful as Jeff Bezos? Is Scooter scared of mediocrity? Why does Scooter think all entrepreneurs are bad at having faith? 4. The Secrets to Being a Better Parent, Child, and Partner: How does Scooter approach trust? How did having kids impact Scooter's mindset? Why was divorce the biggest catalyst in Scooter's entire life? Does Scooter worry that money will negatively influence how his children are brought up? What is the most important thing a child can hear from a parent? 5. Finding the "Scott" Buried Inside "Scooter": It's easy to become the brand you create. How does Scooter prevent losing himself when that happens? What does Scooter need to unlearn in the future? What has Scooter changed his mind on in the past 12 months? How does Scooter approach his relationship to regret? What single lesson you most would Scooter most want a young person listening to this conversation to take away?

David Marcus is the co-founder and CEO of Lightspark, building infrastructure that extends the capabilities and utility of Bitcoin. Prior to Lightspark, David led all payment and crypto efforts at Facebook/Meta and scaled Messenger to 1.5BN users. David previously founded three other companies: Zong (acquired by eBay/PayPal for $240M), Echovox (acquired by MBO), and GTN (acquired by World Access). In Today's Episode with David Marcus We Discuss: 1. From Losing Everything to Becoming Changing the World of Fintech: How did seeing his family lose everything lead to David starting his first company, GTN? Does David believe that great companies can be built in Europe? What are the biggest mistakes David made with Zong? How did they impact his mindset? 2. The Secret to Building a Great Company from Mark Zuckerberg's ex-Right Hand Man: Where does David think Paypal lost its way? How did David "brutally" change PayPayl's company culture when he came in? What worked and what didn't in scaling Messenger to 1.5BN users? Why did Diem (formerly Libra) fail? How did David know when to give up that fight? What is David's biggest lesson from working with Mark Zuckerberg? 3. Crypto & AI's Ripple Effect on The Rest of The World: What will be the fallout from the de-banking of crypto?  How does David think the future of AI will impact income equality? If David was in charge of the SEC, what would he do first? What worries David most about the next 1-5 years in the crypto industry? What are the most significant signs that the tea leaves not looking great for the US dollar? 4. How The Best Leaders Hire The Best Talent: Why does David believe that naivety is good for entrepreneurs? Does David believe we'll be in a worse macro position by the end of the year? How has David changed most as a leader over time? What is David's biggest piece of advice in regard to hiring across many different companies?  

Joost De Valk is one of the OGs of SEO. As the Founder of Yoast, he scaled what was a side project plugin into a multi-million dollar business, used by 13 million sites and selling to Newfold Media in 2021. As one of the early SEO pioneers he is also an extremely coveted angel investor and invests through his company, Emilia Capital. In Today's Episode with Joost De Valk We Discuss: 1. From Side Project to Multi-Million Dollar Business: Why and how did Joost create the first version of Yoast? When did he realise that this was not a side project and could be a big business? What does he know now that he wishes he had known when he started Yoast? 2. When, How and Why To Invest in SEO: When is the right time to invest in SEO? How should one determine how much budget to allocate to SEO? Once decided on budget, what are the first steps to investing in SEO? Which part of the org should SEO team specialists sit in? What are the biggest mistakes founders make when investing in SEO/ 3. AI Changes The World of Context: How does AI change the way businesses create content? How can startups leverage AI to create and distribute more content for SEO? What are the biggest challenges/problems to leveraging AI for content creation? 4. Creating a Developer-Led Brand and Mastering PLG: What is the secret to creating the best developer-led brand? What are the biggest mistakes people make when marketing to developers? How does Joost navigate the balance between having enough value in a freemium product but also retaining enough value to be able to charge for the premium product? Is Joost concerned that budgets will revert back to CFOs and away from individual contributors with the financial downturn that is ensuing?

Rob Lacher founded Visionaries Club in 2019, in just 3 years he has scaled the firm to $600M AUM and backed some of Europe's best including Xentral, Personio, Miro, and Ledgy. Prior to Visionaries, Rob founded the fashion platform AMAZE in 2014 which he sold to Zalando, and founded the European seed and growth stage venture capital fund La Famiglia in 2016. In Today's Episode with Rob Lacher We Discuss: 1.) From Novice Tennis Player to Investing on a Global Stage: When Rob realized beating Federer wasn’t an option, how did he make his way into the world of venture capital? When did Rob know he wanted to be a VC? What did Rob learn about himself after leaving La Famiglia? What characteristics make business partners compatible? 2.) The Secret to Building a Fund? Hire People With No Experience: What does Rob think is the hardest element of building a firm? What advice would Rob give to emerging managers when starting their firms? What is the single biggest mistake that Rob sees hiring managers make? Why does Rob prefer to hire people with no VC experience? 3.) The Red Ocean of European Venture: Does Rob think the Series A product in Europe is any good? How would Rob advise founders debating a US multi-stage fund or a European offer? If Rob could choose one European board member, who would it be and why? In Rob's dream, what would the Europe venture ecosystem look like in 2028? How does Rob think Europe’s family institutions can become Europe's Google? 4.) Lessons on Investing From a Pro: Where does Rob think VCs, founders, and boards are misaligned?  When Rob invests, how central of a role does price actually pay?  What is Rob’s single biggest investing mistake? How did it impact his mindset and approach? What are the three ways reserve management strategy has changed? What does Rob absolutely hate about VC?  

Mike Salguero is the Founder and CEO @ ButcherBox, the meat delivery subscription service that he has scaled to $600M in revenue, 215 employees and the national leader in the space. All of this achieved while raising $0 of venture capital. Prior to ButcherBox, Mike was the Founder & CEO @ CustomMade, an online marketplace that, unlike ButcherBox, raised millions in venture funding from prominent VCs. In Today's Episode with Mike Salguero We Discuss: 1.) The Makings of a Great Entrepreneur: How did Mike's father not being present in his childhood impact the type of leader he is today? How does Mike's fear of abandonment show itself in his leadership style? What does Mike know now that he wishes he had known when he started? 2. Consumer Subscription is Not a VC Backabale Business Model: Why does Mike believe consumer subscription D2C businesses are not VC backable? What are the biggest challenges of running a consumer subscription business? Why did all the D2C food prep and delivery companies fail? What did they do wrong? What happens to all the heavily funded D2C subscription companies of the last 5 years? Why does Mike believe now is the hardest time ever to do D2C consumer subscription? 3. The Secret to Efficient Marketing: How did ButcherBox scale to $50M in revenue with just one marketing channel working? When should founders think about the second channel? How should they choose which one? Why does Mike not like "brand marketing"? How did ButcherBox burn $8.5M on brand marketing? What are Mike's biggest lessons from doing this? What emerging channel does Mike see as having the biggest potential over the coming years? Why does customer acquisition increase with time? Why do elections cause it to increase? 4. The Economics of a $600M Revenue ButcherBox: How much does it cost ButcherBox to acquire a customer? What is their payback period on that customer? How has this change with time? What is the single metric that drives the profitability of ButcherBox? What are the single biggest points of margin in the business? What is the lifetime value of a ButcherBox subscriber? What are the single biggest points of churn in the customer lifecycle? 5. Venture Capital: To Raise or Not to Raise: Why did Mike never raise venture capital for ButcherBox? Has Mike ever sold secondary? Why not? What would Mike most like to change about the world of venture capital? What are his biggest lessons from raising VC with CustomMade? How did that impact how he approached building ButcherBox? What does Mike believe all founders need to know about raising VC?

Tobi Lütke is the CEO and Co-Founder of Shopify, the powerhouse company allowing anyone to start and grow their e-commerce business. Over an incredible 18 years, Tobi has scaled Shopify to 10% of total US e-commerce, millions of merchants in over 170 countries, and a market cap today of over $60BN. Huge thanks to Harley Finkelstein for making this happen. In Today's Episode with Tobi Lütke We Discuss: 1. From a Small German Town to One of the World's Most Powerful CEOs: What did Tobi want to be when he was growing up? Who did Tobi learn most from in his younger years? How does Tobi think about the importance of mentorship in learning? What does Tobi know now that he wishes he had known when he started Shopify? 2. You Can Learn More from World of Warcraft Than You Can Companies: Why does Tobi believe you can learn more from World of Warcraft than you can from studying companies? Why does Tobi believe that humans are terrible at company building? What are the most obvious ways we can improve the quality of the companies we build? Why does Tobi believe that in-person is far superior to remote working? What are the nuances? 3. The Best Companies Operate with Many Constraints: Why does Tobi believe in all cases, constraints produce creativity? What is the difference between an enforced constraint and an artificial constraint? How can leaders create and enforce artificial constraints when they are not real? How do the best leaders use constraints to ensure their companies move faster and faster? 4. Inside the Mind of Tobi Lütke: Decision-Making & Prioritisation: How does Tobi reflect on his own decision-making process? How has it changed? Why does Tobi believe that sunk cost fallacy is BS and only leads to your outsourcing approval to someone else? Why does Tobi hate "black boxes"? How does he remove them from the org entirely? How does Tobi decide what to learn? What is his learning process once he has made this decision? How does Tobi decide what to prioritise in terms of strategic initiatives for Shopify?

Jackie Reses is the Chair and CEO of Lead Bank, a community bank in Kansas City.  Previously, she was the Executive Chairman of Square Financial Services and Capital Lead and Head of the People Team at Block Inc (Square). Prior, she had leadership positions at Yahoo! and was a Partner at Apax Partners Worldwide. Jackie also spent seven years at Goldman Sachs in mergers and acquisitions and the principal investment area. Jackie is on the board of directors of Endeavor, Affirm and Nubank. Previously, she served on the Board of Directors of Alibaba Group. She has been named one of Forbes' “Self Made Women”, Fast Company’s “Most Creative People in Business,”  and American Banker “Most Powerful Woman in Finance”.  In Today's Episode with Jackie Reses We Discuss: 1. From Humble Beginnings to "Most Powerful Woman in Finance": What is Jackie running from? How did Jackie's upbringing impact her approach to business and management today? What does jackie know now that she wishes she had known when she started her career? 2. Building the Best Teams: Lessons from Square and Yahoo Why does Jackie believe that past experience is BS in hiring candidates for a role? Why does Jackie deliberately not look for domain knowledge when hiring? Why does Jackie believe employers should tell candidates what they suck at in hiring? What does Jackie mean when she says, "you have to invest in people for 20 years"? 3. The Best Deal-Maker in the Business: Secret to Negotiating: What does Jackie believe is the secret to successful negotiations? How did Jackie do the Alibaba deal for Yahoo and make $50BN for them? Why does Jackie believe the Laffonts and Coatue are the best risk managers? What are the biggest mistakes people make in deal-making today? 4. The Next Wave of Fintech: Who wins and who loses in the next wave of fintech? What will happen to the crypto industry? How will crypto be regulated? Why does Jackie believe that financial super apps are BS? Why does Jackie believe that Goldman tried and failed to innovate? Will we see a wave of M&A in fintech over the coming years?

Jag Duggal is the CPO @ Nubank where he is responsible for product strategy and roadmap reporting to CEO David Velez. Jag leads over 200 professionals across different functions within his role. Before Nubank, he was the Director of Product Management at Facebook, leading monetization of video and third party content. Before Facebook, Jag spent close to 7 years at Quantcast as a Senior VP of Product Management & Strategy. Finally, pre-Facebook, Jag was at Google for 5 years as a Group Product Manager and Head of Strategy (Display). In Today's Episode with Jag Duggal We Discuss: 1. From Cushy Valley Job to CPO @ Brazilian Startup: Why did Jag leave the life of luxury in the valley at Facebook to join David as CPO @ Nubank? What does Jag know now that he wishes he had known when he took the position? What one piece of advice would Jag give to a product leader starting a new position today? 2. Product: The Playbook, Art vs Science: Why does Jag believe that product is 90% science? What is the final 10%? Why does Jag believe that you should not listen to your customers? What is the right way to ask customers questions to determine their pains? Why does Jag believe that you should not fall in love with your own ideas? 3. Building the Bench: Hiring the Best Team: How does Jag approach the hiring process for all new product hires? What are the single biggest mistakes Jag has made when hiring for the product team? What are the must ask questions when hiring for product? What hiring lesson did Jag learn from Kevin Systrom? How has he applied it today? What did Jag believe about hiring that he now no longer believes? 4. Go Time: Build, Manage and Execute: Why does Jag think execution is overrated and strategy deserves more credit than people give it? How does Nubank utilise small teams to operate fastest? What have been lessons here? What are the best ways to do product post-mortems? What works? What does not work? What has been Jag's best product decision? What has been his worst?

Dara Khosrowshahi is the CEO of Uber, where he has managed the company’s business in more than 70 countries around the world since 2017. Dara was previously CEO of Expedia, which he grew into one of the world’s largest online travel companies. Dara was promoted to Expedia CEO after serving as the Chief Financial Officer of IAC Travel. Before joining IAC, Dara served as Vice President of Allen & Company and spent a number of years as an analyst. He currently serves on the Board of Directors of Expedia and Catalyst.org and was previously on the board of the New York Times Company. In Today's Episode with Dara Khosrowshahi We Discuss: 1. From the Iranian Revolution to One of the Most Powerful CEOs: What is Dara running from? What is he running towards? How did seeing his family lose everything impact his mindset to life and business? What are 1-2 of Dara's biggest lessons from working with the legendary Barry Diller? How did Daniel Ek @ Spotify convince Dara to take the CEO role at Uber? 2. Dara Khosrowshahi: The Foundations of Great Leadership: What does high performance in business mean to Dara? Does Dara agree, "the best CEOs are the best resource allocators"? Does Dara believe he is a better peacetime or wartime CEO? Which is he at Uber? What decision-making framework does Dara use to make really hard decisions? How does Dara does what to focus on and what to prioritise? 3. Investments and Acquisitions: The Scorecard: Why did Dara decide to make the Kareem acquisition? Has it been successful? What was the thinking behind the Postmates acquisition? What does Dara believe is the single best acquisitions he has made at Uber? What has been the worst acquisition he has made at Uber? Why does Dara believe that Uber entering scooters was a mistake? 4. The Future: Food Delivery, Parenting, Marriage: What does Dara say to those who suggest Uber Eats has lost the war to Doordash? What does Dara believe is the secret to a happy marriage? How does Dara define great parenting? What does Dara do to be the best father he can be? What would Dara like to improve or change about himself? Why?

Mike Maples is one of the OGs of seed investing. As the Co-Founder of Floodgate, he has backed the likes of Twitch, Okta, Lyft, Twitter and more. Mike has been on the Forbes Midas List eight times in the last decade and was also named a “Rising Star” by FORTUNE and profiled by Harvard Business School for his lifetime contributions to entrepreneurship.  In Today's Episode with Mike Maples We Discuss 1.) Lesson from SVB #1: The Importance of Scenario Planning: What is the right way to do scenario planning in startups? What is the difference between good vs bad scenario planning? What do the best scenario plans include and involve? What is the right way to communicate these scenario plans to your stakeholders? 2.) Lesson from SVB #2: The Importance of Financial Agility: What does it mean for a startup to be "financially agile"? From a banking relationships perspective, what can startups do to be financially agile? How many accounts should a startup have? How much runway should be in each? Should startups bank with startup banks as well as traditional banks? Should startups have their money in sweep accounts and money market accounts? 3.) Lesson from SVB #3: How to Master Crisis Communications: Why is it so important for founder to over-communicate in tough times? How transparent should they be in these communications? What does Mike mean when he says "be radically human"? If Mike were to face a crisis, what would he do differently in the way he communicates to his LPs? 4.) Lessons from SVB: The Wider World: Why does Mike believe the level of quantitative easing that occurred in COVID was scandalous? Does Mike believe the USD will continue to be the reserve currency of the world? Will we be in a better or worse macro situation by the end of the year? Has Mike ever had a company that achieved true PMF and failed?

Frank Fillman is CRO/Country Leader Australia for Salesforce where he is responsible for responsible for the overall strategy, execution, success, and growth of the $1B+ Australian market across all industries. Prior to Salesforce, Frank was SVP/GM @ Tableau where he was responsible for the strategy, execution, and growth of Tableau's Top Accounts. Over the last 10 years at Salesforce, Frank's accomplishments include $500M+ new revenue closed in 5 years and $1B+ revenue managed. As a result, Frank has been awarded #1 Sales VP of the Year, North America, 3 times! Huge thanks to Zhenya Loginov @ Miro for the intro to Frank today. In Today's Episode with Frank Fillman We Discuss: 1.) From Selling Kitchen Utensils to Leading $1BN Revenue Line for Salesforce: How did Frank first make his way into the world of sales selling kitchen utensils? Why does Frank believe, "how you handle tragedy defines you"? How did it define him? What does Frank know now that he wishes he had known when he started in sales? 2.) Build and Execute the Sales Playbook: How does Frank define what a "sales playbook" is today? What is it not? Literally, what are the first steps to building a sales playbook? Is it the founder who does it? What does a good playbook have? What does a bad playbook have? What makes the best? What tools should founders and sales leaders use to create their playbook? 3.) Enterprise Deal Dynamics 101: Why does Frank believe that you should never start with the price or "send over numbers"? How can enterprise sellers create urgency in a deal cycle? What works? What does not work? How does Frank advise sales teams on the use of discounting? How open should reps be in communicating the win for them as well as the win for the customer of closing a deal? 4.) Building the Bench: How does Frank structure the hiring process for all new sales reps? Why does Frank believe that all sales leaders want to be super reps? How does Frank rank high potential vs high experience when hiring reps? What matters more; the exec have experience in the sector you are selling into or the deal size? What are the single biggest mistakes founders and leaders make when hiring sales? 5.) Setting Quota and Deal Reviews: How does Frank advise founders on setting quotas? Why does Q1 set the tone for the year? How does Frank conduct deal reviews? How often? With who? What is the agenda? What is the one question that Frank always asks when a rep says, "the client told us it was not a priority and so it slipped into next quarter"? How does Frank advise founders and sales leaders on multi-threading large enterprise accounts? Items Mentioned in Today's Episode: Frank's Most Recent Book: The Go-Giver: A Little Story About a Powerful Business Idea  

Bill Ackman is the CEO of Pershing Square Capital Management, L.P., an SEC-registered investment adviser founded in 2003. Pershing Square is a concentrated research-intensive fundamental value investor in long and occasionally short investments in the public markets. Bill is also a member of the board of Universal Music Group N.V. He serves as a member of the Investor Advisory Committee on Financial Markets for the Federal Reserve Bank of New York, and a member of the Board of Dean’s Advisors of the Harvard Business School. Prior to forming Pershing Square, Mr. Ackman co-founded Gotham Partners Management Co., LLC. In Today's Episode with Bill Ackman We Discuss: 1.) From HBS to Starting Your First Fund: How did Bill go from HBS to raising his first fund in Gotham Partners? How was that first fundraise? From 100 meetings, what worked? What did not work? What were the core fundraising lessons? What did Bill learn about great partnerships from his time with David building Gotham? 2.) Bill Ackman: A Winner's Mindset: How To Deal with the Highs and Lows: On reflection, what have been the most challenging times for Bill professionally? What does he say to himself when he is going through the hardest times? What is his mind talk? When the war is lost and it is time for learning, how does Bill reflect and learn from losses? Bill has previously described himself as "the most persistent man in America". How does Bill know when enough is enough, he was wrong and it is time to change his approach? 3.) Bill Ackman: SVB + Bank Runs and The Future of our Financial System: Why does Bill believe that the depositor guarantees for SVB and Signature Bank have created a "Three Tier Banking System"? What are those three tiers? Why does Bill believe that SVB is now the safest place to deposit your money? Why is First Republic Bank and SVB very different in terms of their exposure? What can be done to prevent further bank runs? What should the Fed be doing? Why are they not doing it? What would Bill do if he was in charge of the Fed? Why does Bill believe the current levels of FDIC insurance are insufficient and outdated? What should be used in their place? 4.) Bill Ackman: The World Around Us & Potential Politician Why does Bill want Jamie Dimon to run for President? If it is Trump vs Biden, who wins? Why does Bill believe Biden's tax policies destroy the US economy? What should we have instead? Why does Bill believe we should give every newborn baby $6,500 and invest it for them when born? What are Bill's 10-Year Long's and 10-Year Shorts? Why them? Would Bill ever run for politics? When is the right time?

Ophelia Brown is the Founder of Blossom Capital, one of Europe's newest but leading early-stage venture firms. Ophelia and the Blossom team have invested in stand-outs including Checkout, Duffel, Tines, and Moonpay. Prior to Blossom, Ophelia was a GP at LocalGlobe and a Principal at Index Ventures where her investments included Robinhood and Typeform. In Today's Episode with Ophelia Brown We Discuss: 1.) From Restaurant-Owning DJ to Leading European VC: How Ophelia made her way into the world of venture and came to found Blossom? What does Ophelia know now that she wishes she had known when she entered venture? What does Ophelia feel she is running away from? 2.) Venture Capital: The Market: Why does Ophelia believe the best venture firms focus either by stage/theme/geography? Why does Ophelia believe that marketing in venture has no substance? How can founders determine between what is real and what is false? Why does Ophelia believe that growth investors have ruined the venture market? When does Ophelia believe VCs will realise that FOMO investing is not a good strategy? 3.) Ophelia Brown: The Investor and Fund Manager: What has been Ophelia's biggest investing mistake? How did it change her mindset and approach? In a world where everyone does seed investing, why does Ophelia not? How was raising the first Blossom fund? What were some of her biggest lessons? Why does Ophelia believe that follow-on investing can damage returns? How does Ophelia reflect on her own relationship to price? When has she paid up and it worked? When has she paid up and it not worked? Does Ophelia think it is fair that many find her curt and abrasive to work with? 4.) Europe: Is Now Really The Right Time? What would Ophelia like to see change in the way European VCs act? If Ophelia could invest in one seed firm, one Series A firm and one growth firm in Europe, what would they be? Why? What are 1-2 of the biggest barriers Europe must overcome in the next 5 years?

Adam Grenier is an OG of the growth world. His first role in growth, was none other than Uber where he was Head of Growth Marketing and Innovation building the global marketing growth infrastructure and team from the ground up. He then enjoyed successful spells at Lambda School and Masterclass as VP Growth and VP of Marketing, respectively. If that was not enough, Adam is also a prolific angel having made investments in Superhuman, Table22, and FitXR to name a few. In Today's Episode with Adam Grenier We Discuss: 1.) Entry into the World of Growth with Uber: How did Adam make his way into the world of growth with Uber and Ed Baker? What are the single biggest takeaways from his time at Uber, Lambda and Masterclass? What does Adam know now that he wishes he had known when he started in growth? 2.) Growth: What it is? Why You Do Not Need a Team for it? How does Adam define the term "growth" today? What is the role of "Head of Growth"? Why does Adam believe that you do not need a growth team? How can leaders infuse growth principles, mindsets and metrics into existing teams? WHat are the single biggest mistakes founders make when thinking about growth? 3.) Hiring Growth Mindsets: How to Ask the Right Question: What are the clearest signs to Adam that someone has a growth mindset? What are the right questions to ask to see how they think? How does Adam use tests and case studies to determine the growth mindset of a person? What did Uber teach Adam about the best practices to hire for growth? 4.) Uber: Scaling a Monster and Spending $1BN on Ads: What are some of Adam's biggest lessons from spending $1BN on advertising at Uber? Why at anytime were there 200 people paying for ads with their personal credit cards? Why does Adam believe China was "the wild-west"? How did all of their competitors in China have Uber data? How do growth mechanics, channels and disciplines compare between US vs China?

Jackie Reses is the CEO of Lead Bank and previous Exec Chair of Square Financial Services and Head of Lending and Banking. One of only people to have started a bank as a de no; Only tech company to get approved for a de novo. Chair Economic Advisory Council of SF Federal Reserve.  Kris Dickson is the CFO of Lead Bank and previously the CAO / CFO of post-BK Lehman Brothers parent co-estate for 10 years. Lehman Holdco estate has liquidated and distributed $129 billion to unsecured creditors through the end of 2022. In Today's Episode on SVB We Discuss: What Happened? How and why did SVB fail so fast? Was it the result of systemic problems or a series of management mistakes? What role did VCs play in the downfall of SVB? What role did social media and online banking play in the failing of SVB? What Now? What happens now? Will depositors have their deposits guaranteed? Will there be a buyer for SVB? Who is the most likely? Should founders be worried about moving their money to neo-banks? Should founders in any circumstances transfer money to their personal accounts? What is the best and worst outcome?

Amjad Masad is the Founder and CEO @ Replit, whose mission is to bring the next billion software creators online. With Replit, Amjad has raised over $100M from the likes of Peter Thiel, a16z, Coatue and Addition, to name a few. Before founding Replit, Amjad was a tech lead on the JavaScript infrastructure team at Facebook. Before Facebook, Amjad was #1 employee at Codecademy. In Today's Episode with Amjad Masad We Discuss: 1.) From Troublemaker Child in Iran to Silicon Valley Founder: How did Amjad make his way into the world of tech and Silicon Valley having grown up as a misbehaving child in Iran? In what ways did Amjad show early signs of exceptionalism? Why does he always look for this in people he is hiring for Replit? What does Amjad know now that he wishes he had known when he started Replit? 2.) The Future: A New World with AI at the Centre: Why does Amjad believe we will see thousands of billionaires created from the innovation in AI? Why does Amjad believe AI will lead to 100 more Elon Musks? If Amjad were CEO of Facebook, what would he do? Why and how do they have to invest in AI? Will TikTok be banned in the US? How will this be resolved? Why does Amjad believe that 300 people control the future of AI? Is that not concerning? 3.) The Future of Society, Employment and Wages: Why does Amjad believe in 10 years, 1 engineer will be able to do what 100 do today? What will happen to the real wages of engineers? How does Amjad see the inclusion of universal basic income in the future? Is Amjad concerned about societal and civil unrest with wealth disparity widening further? 4.) Building the Replit Army: Why does Amjad believe that so many in tech have gotten too soft in the last few years? Why does Amjad release a "Why You Should Not Join Replit" page and share it with all candidates? How can a founder know if they have good company values or not? Why does Amjad feel we need a spiritual reform in company building? Why are startups and religion the same?

Glen Coates is the VP of Product @ Shopify, leading the development of Shopify’s core commerce platform. He also oversees the core developer platform and Shopify’s partner ecosystem, which includes over 10,000 publicly available apps in the Shopify App Store. Originally a CompSci grad, Glen moved from Sydney to San Diego in 2008 to run US distribution and e-commerce for an Australian eco-products company. In 2010, he attended Columbia Business School for one whole day before quitting to start Handshake, a SaaS B2B e-commerce platform. Glen joined Shopify in May 2019 when the company acquired Handshake. Glen has been in the Vice President role since October 2020. In Today's Episode with Glen Coates We Discuss: 1. From Game Developer in Sydney to Running E-Commerce Warehouse in NYC: How Glen made his way into the world of product and e-commerce having started life as a game developer? Why does Glen believe that the best founders and product people often have their roots in gaming? What does Glen know now that he wishes he had known when he joined Shopify? 2. The Art of Product and Product Management: Is product more an art or a science? If you had to put a number on it, what would it be? What is "product management"? Why can it not be reduced to frameworks? What are "product principles"? How do Shopify use them? How should product teams set them? What makes the very best PMs today? What are the commonalities in them? What is the sign of a poor PM? What would Glen most like to change about the world of PMs? 3. The Art of Product Marketing: What does Glen believe is the true art of product marketing? How did a CEO group teach Glen how to tell truly great stories? How can one tell great stories when you have to cater to multiple different customers/personas? How does Glen evaluate the current state of Shopify's product marketing? 4. Shopify and The Future of Shopify: Why does Glen think it is important for Shopify to have a tops down decision-making process for product strategy? What does Glen believe is the #1 reason why Shopify is such a large and successful company? What is the single hardest element of Glen's role today? How does Glen believe that Shopify will be larger than Amazon in 5-10 years time?

Alex Schultz is the Chief Marketing Officer and VP of Analytics for Meta (formerly Facebook), leading Marketing, Analytics, and Internationalization. Previously, Mark Zuckerberg stood up and said, "Facebook would not be a BN user company without Alex". At Meta, Alex has pioneered the integration of product and direct response marketing at Meta and helped launch many of the company’s most impactful products and initiatives. Alex is gay and is the executive sponsor of Facebook’s LGBTQ+ Employee Resource Group. In Today's Episode with Alex Schultz We Discuss: 1. From Paper Planes to CMO of Facebook: How Alex started his career in the world of paper planes and how that led to his getting a role at an early eBay? What are 1-2 of his biggest lessons from eBay? How did the role at Facebook come about in 2008? Why did he decide to join the early Facebook? What does Alex know now that he wishes he had known when he started his time at Facebook? 2. The Secret to Scaling to 1 Billion Users: Mark Zuckerberg has said that "Facebook would not be a billion-user company without Alex". So what does Alex believe are the 1-2 biggest needle movers in FB scaling to 1 billion users? Why does Alex believe that the best leaders are patiently right? How can management be direct and effective but also show they care and be kind? What have been some of Alex's biggest lessons on people management across different phases of the company? 3. Crucible Moments in Facebook History: Facebook Messenger Split: What was the decision-making process behind splitting Messenger from the core Facebook App? What did they do right and well in the split? What mistakes were made? Rebrand to Meta: Why did Facebook decide it was right to rebrand to Meta? Has the rebrand gone well? How does Alex define success with the rebrand? Reels vs TikTok vs SNAP: Does Alex believe we are moving away from the social graph and moving to content discovery only? How does Alex feel Reels is doing in the race against TikTok? What have they done well? Why does Alex believe SNAP hasn't innovated in the way people think and copied Kakao in cases? What is the key to turning Reels into a monetization machine for Facebook? 4. Alex Schultz: The Person and Leader: How was the coming out process for Alex in the tech community? How did his parents respond to the news? What does Alex mean when he says, "everyone has to mourn their own version of your future self"? Why when he moved to the states was Alex advised to go back in the closet? Does Alex feel we have a long way to go in equalizing the playing field both for homosexuality and trans-gender participation?

Hunter Somerville is a Partner @ Stepstone, one of the largest secondary buyers, fund investors and players in our ecosystem with over $600BN in capital responsibility and over $100BN AUM. Additionally, Hunter serves on the LP Advisory Boards for Felix Capital, Foundry Group, Imaginary Ventures, Scale Venture Partners, Boldstart Ventures, Ludlow Ventures, and more. Prior to StepStone, Hunter was a general partner with Greenspring Associates, a venture capital and growth equity investment firm that merged with StepStone in 2021. Before that, he worked as an associate for Camden Private Capital. In Todays Episode with Hunter Somerville We Discuss: 1. Three Types of Secondaries: What are the three different types of secondaries? What is the current situation with company secondary opportunities today? What is the current landscape for fund secondary opportunities today? What are GP-led restructuring or strip sales? How do they work? 2. LPs Today and Moving Forward Investing in Funds: Will we see a wave of LPs not commit to their existing managers? What is the denominator effect and how does that impact LP deployment into funds? What are the top 3 reasons why LPs will not re-commit to existing managers? Do LPs feel VCs have fairly marked down their venture books in the last 6 months? Does Hunter agree that if you have not returned cash to your LPs when you could have done ijn the last 5 years, then you are most in trouble? Why does Hunter believe we will see more international LPs entering venture than ever before? 3. Liquidity: When Does the Cash Hit: Why was liquidity so bad in 2022? How did that compare to 2021? How does Hunter forecast liquidity environments in 2023? What could drive them? How active were Stepstone in secondary buying over the last few years? Is now the time to be greedy when others are fearful in secondaries? What discount was Hunter seeing both on fund and company side secondaries in 20-22? What is the current level of discount being applied to both company and fund secondaries? 4. AMA with One of the Largest Secondary Buyers: Which LP class will be hurt the most from the last fund cycle? What would Hunter most like to change about the world of venture? What was Hunter's biggest mistake on a company investment? What are the biggest mistakes LPs make when they do direct investing? Why are big-name people entering firms as GPs not always a good sign?

Jamie Siminoff is the Founder and Chief Inventor @ Ring, with Ring Jamie, created the world’s first Wi-Fi video doorbell while working in his garage in 2011. Since Ring’s launch in 2013, Ring has helped make thousands of neighborhoods safer all around the world. As part of the journey, Jamie raised over $385M from the likes of True Ventures, Felicis, First Round, CRV, Upfront and more. In 2018, Amazon acquired Ring for a reported $1BN. Prior to Ring, Jamie founded several successful ventures including PhoneTag, the world’s first voicemail-to-text company, and Unsubscribe.com, a service that helped email users clean commercial email from their inboxes. He successfully sold both companies in 2009 and 2011 respectively. In Today's Episode with Jamie Siminoff We Discuss: 1.) From Creating the First Wi-Fi Doorbell to $BN Acquisition: When was the moment Jamie realized he had to create the world's first Wi-Fi-enabled doorbell? How di Richard Branson come to be an investor in Ring? What was the process? How does Jamie advise other founders when it comes to the question of whether it is valuable having business moguls as investors in their business? 2.) Crucible Moments: From Lawsuits and Near-Death to $22M in Sales in a Day: When Jamie hears the words "near-death experience" what is the moment in the Ring journey that comes to mind? How did Jamie get through a crippling lawsuit and come out selling $22M in 24 hours on QVC? How did Jamie feel when he placed a $500M order with manufacturers when he only had $100M? What does Jamie believe was the hardest phase of the business? 3.) Jamie Siminoff: The Leader: Why does Jamie want to hire marathon runners? Why does the analogy make for good hires? Does Jamie start from a position of trust with new hires and it is there to be built or start with no trust and it is there to be gained? Does Jamie believe he is a tolerant leader? What does he mean when he says, "I want to see the dirt under your fingernails"? Why does Jamie believe that building a brand is like making great wine? Why does Jamie really hate customer surveys? What should be done instead? 4.) Selling for $1BN to Amazon: How did the Amazon acquisition come to be? How did the discussion go? Why did Jamie decide then was the right time? When you sell for a $1BN, does the cash hit your account soon? When did Jamie actually receive the money? How did he feel when he saw it is in his account? What does Jamie believe Ring did so well to make the acquisition a success? What did Amazon do well to ensure Ring was integrated most effectively? What are 1-2 of the biggest lessons Jamie has learned from being within Amazon?

David Tisch is the Managing Partner of BoxGroup, one of the leading seed-stage investment firms of the last decade having invested in over 500 seed-stage startups, including Plaid, Ro, Ramp, PillPack, Amplitude, Flatiron Health, Stripe, Warby Parker, Harry’s, Oscar, Flexport, Classpass, Vine, GroupMe, Airtable and more. David is also the Chairman of GoodDog, a marketplace to find pets online. In Today's Episode with David Tisch We Discuss: 1.) From Techstars To Founding BoxGroup: How did David start his own firm in the form of Box having started at Techstars? What advice from Brad Feld does David always remember and hold close? What does David know now that he wishes he had known when started investing? 2.) The Debate: The Math Does Not Work: Portfolio Construction: Ownership Does not Matter: How does David justify writing $100K checks from a $127.5M early-stage fund? Even if it is a home run, it does not make a difference to the fund? Level of Diversification: If David is writing small checks like this, with his fund size he will have hundreds of companies, what does David believe is the right level of diversification? Reserves management: How does David think about the ratio of initial to reserves when deploying the funds today? How does reserves management change in a recession? How does David prevent other VCs from using this to try and push him down to always writing a $100K check? Why does David believe that the size of check he is able to invest is the VC's problem and not the founders? Price Sensitivity: How does David assess his own relationship to price today? Why does he believe that company valuation is not something that the investor controls? 3.) Advice to Founders Raising Rounds: What does David believe is the #1 role of the CEO? What are the three most important variables for founders to focus on when raising their round? How should founders analyze the tradeoff between the brand of the VC and the size of the round? Does signaling really make a difference when a large fund invests at seed? How did multi-stage funds change the seed landscape forever with a new product? Who does David believe are the tourists in early-stage venture? Will they leave in the recession? 4.) David Tisch: AMA: Why does David believe that consumer social is not fun anymore? Who when they send him a deal does David take it most seriously? How does David want to ensure that bad VC behaviour is exposed? What would David most like to change about the venture landscape today?

Joey Levin is the CEO of IAC where he has overseen the constant evolution of the company, including the initial IPO and subsequent spin-off of Match Group, the spin-off of Vimeo, and the acquisitions of Angie’s List and Care.com. If that was not enough, in October 2022, Joey was also appointed as CEO of Angi Inc. In addition to this, Joey also serves on the boards of IAC, Turo, and MGM Resorts International. In Today's Discussion with Joey Levin We Discuss: 1.) The Makings of a Great Leader: When Joey was younger, what did he want to be when he grew up? What is Joey's biggest advice to people coming out of college/university at this time? What 1-2 things does Joey credit his internal and fast rise in IAC to? 2) Value Investing is BS & The Markets Today: Why does Joey believe the idea of "value investing" is BS? What 1-2 behavior traits of investors in the last few years were most dangerous? Why does Joey believe that the current market is reasonable and now is the new normal? How does Joey keep internal morale high when people have become accustomed to high stock prices? Does Joey believe in the statement, "be greedy when others are fearful and fearful when others are greedy"? 3.) Simplification is the Secret to Margin & Messaging 101: Why does Joey believe simplification is the core of high margins? How can startups and scale-ups identify where to simplify first? What are the subsequent steps? Why does Joey believe that the best values should make you feel uncomfortable? What is a lesson from Joey's father on what makes truly great messaging? 4.) Parenting, Money and Marriage: How does Joey reflect on his own relationship to money today? What are 1-2 lessons taught by his mother on how to approach money and wealth? What does Joey believe is the secret to truly happy marriages? What are Joey's biggest lessons on what it takes to be an effective and good father?

Kevin Systrom and Mike Krieger are the co-founders of Instagram. Since its release in 2010, Instagram has become of the most significant products in modern society shaping the way millions of people engage with the world around them. In January this year, Kevin and Mike announced their return to the founding arena with the launch of Artifact, a personalized news feed driven by artificial intelligence. In Today's Show with Kevin Systrom and Mike Krieger We Discuss: 1.) The Perfect Partnership: Question from Josh Kushner @ Thrive: What makes Kevin and Mike such a great partnership? What was the last disagreement they had? How was it resolved? They built Instagram in person, in an office. They are building Artifact remotely, what has changed in the way they operate when comparing remote to in-person? 2.) Why Social Networks are Broken & The Next Frontier: Why does Kevin believe social networks today are broken and should be less social? What fundamental premise are social networks built on that Kevin believes is wrong? How will AI and machine learning be central in the next wave of social? How do Kevin and Mike evaluate TikTok and the next wave of content discovery? 3.) Welcome Artifact: The Comeback: Why does Kevin believe they chose the worst idea for their new company? Why is it? Were they nervous about founding Artifact and expectations being so high given Instagram? Why does Kevin argue that Artifact is not actually a "news app"? What does Kevin believe is the biggest lesson Apple taught us about messaging? 4.) Family, Money, San Francisco: Why does Kevin believe that SF will return as the centre of tech once again? Why does Kevin believe that many millennials in the workforce today are entitled and soft? How has becoming a father changed the way Kevin and Mike operate and execute? How do Kevin and Mike assess their relationship with money today? How has it changed? 5.) Hiring, Investing, Managing: What are some of Kevin and Mike's biggest lessons when it comes to hiring? What are the single biggest hiring mistakes they have made? Is it wrong to not hire someone because they are really really boring? What are the biggest lessons for Kevin and Mike from their angel investing?

Zach Lawryk is Head of Solutions Consulting @ Rippling, what is solutions consulting? They are the product expert in the solution that ties a business value to help support the sales rep in the execution of their quota. And there is no one better than Zach, prior to leading the solutions consulting team at Rippling, Zach was VP of Solutions Consulting at Slack where he scaled the SE team from 10 to 200. Before Slack, Zach was Head of Solutions Engineering @ Optimizely and before that was Director of Sales Engineering at Box. In Today's Episode with Zach Lawryk We Discuss: 1. ) WTF is Solutions Engineering: What is Solutions engineering and why is it important? How does a software developer turned lawyer become one of the OGs of Solutions Engineering? What is the single biggest piece of advice Zach gives to graduates entering the workforce today? 2.) When and Who: Building the Foundations: When is the right time to hire your first solutions engineer? Should this be a senior hire or a more junior hire? What experience is ideal? Would Zach rather have someone who has sold to the same customer segment or sold to the same deal size? What are the challenges with each? 3.) Making the First Hire: The Process: What is the right hiring process for solutions engineers? Which members of your existing team should be involved in the process? What are some of Zach's favourite questions on the candidates past to determine quality? What are the best case studies and tests to give potential hires to test their aptitude? What are the biggest red flags in the hiring process for solutions engineers? 4.) Integrating into the Team: Making it Work: What is the optimal onboarding process for solutions engineers? Why does Zach think it is important they spend time with customer success in their first month? What is the right way to measure the effectiveness of SE's? How should the entrance of SE's impact the close rate and comp structure for AE's? How can sales leaders prevent division and friction between AEs and SEs?

Aloe Blacc is a GRAMMY nominee and the voice behind such hits as Wake Me Up, The Man, SOS, I Need A Dollar, and many more. Aloe has toured the world, won countless awards but his latest album, All Love Everything, is the singer-songwriter’s first collection of material written as a father. “Becoming a father made me want to share those experiences in music,” he says, admitting it’s a challenge to translate such a powerful thing into lyrics and melody. If that was not enough, Aloe is also an entrepreneur with the founding of his new company, something we discuss in the show today. In Today's Discussion with Aloe Blacc: 1.) Entry into Music and Running From Fame: How Aloe first fell in love with music and made his foray into the world of music from Ernst & Young? Why does Aloe believe he is running from fame? What does it bring that he does not like? What does Aloe believe he is running towards? How has this changed? 2.) The Art of Storytelling: How does Aloe think about what it takes to be truly great at storytelling? What is the difference between a great vs an average story? How has his style of storytelling changed over time? What are the biggest mistakes that people make in storytelling? 3.) The Songwriting Process 101: What is Aloe's process for writing new songs? How does he take an idea and expand it, test it and execute against it? How did "Wake Me Up" with Avicci come about? What was the creation process there? What was it like working with Avicci? What did Aloe learn from him about being liked? 4.) Marriage, Fatherhood, and Global Stardom: What does Aloe believe is the key to truly successful marriages? How does Aloe retain a sense of romance with intense work pressures? How has becoming a father changed the way in which Aloe thinks and operates? What is Aloe's love language? How has doing this with his wife changed their relationship?

Mike Duboe is a Partner @ Greylock where he sits on the board of Builder, Inventa, Novi, Pepper, Postscript. Prior to entering the world of venture, Mike was the first in-house growth hire at Stitch Fix, where he built and led the Growth organization helping take the company through to their IPO. Before Stitchfix, Mike was the first growth hire at Tilt, where he built and oversaw multiple teams, including analytics, marketing, community, and growth product. He also served on YC’s growth advisory council and was a growth lecturer at Reforge. In Today's Episode with Mike Duboe We Discuss: 1.) Entry into the World of Growth: How Mike made his way from consulting at Bain to leading the growth team for Stitchfix? What did Mike believe about growth 5 years ago that he no longer believes? What does Mike know now that he wishes he had known when he entered the world of growth? 2.) When and Who To Hire: How does Mike define the term "growth team"? What is their core role and responsibility? Should the first growth hire be a senior growth lead or a more junior analytical lead? What data foundations should founders have in place prior to their growth hire joining? What are the most common ways founders fail to prepare for their first growth hires joining? When does Mike believe is the right and crucial time for growth hires to be made? Should these growth hires join existing teams or be put in standalone "growth teams"? 3.) The Hiring Process: How to Detect and Win the Best: How should founders structure the interview process for their first growth hires? What are the best questions to ask to reveal the quality of a potential growth hire? What are the right case studies and tests to do to assertain their quality? What are the different levels of comp package for different growth execs? What are the single biggest mistakes founders make in the hiring process? 4.) Mastering Paid Marketing: Lessons from Stitchfix: Why is CAC/LTV a BS metric? What should be used instead? When is the right time to start really engaging with paid marketing? How should marketing and growth teams determine budget on a per channel basis? How much is the right mix between paid vs organic? What are Mike's biggest lessons from making paid work so well at Stitchfix? What are the single biggest mistakes Mike sees founders make today with paid marketing?  

Tom Loverro is a Partner @ IVP where he has led or was actively involved in investments in Amplitude, Coinbase, Hashicorp and Datadog to name a few. As a result of his investing success, Tom was named to Forbes Midas List in 2021. Prior to joining IVP, Tom was a Principal at RRE Ventures. In Today's Episode with Tom Loverro We Discuss: 1.) The Entry into Venture: How did Tom make his way into venture first with RRE? How did the role with IVP come about? Does Tom believe we will see many venture investors move firms with much of their existing expected carry cut in half with the changing landscape? What is Tom's biggest advice to someone looking to make their way into the venture world? 2.) The Calm Before the Storm: Why does Tom believe now is the calm before the storm? Why does Tom urge founders to go out and raise now before the storm hits? Is Tom already seeing pricing coming down for both early and late-stage companies? 3.) When The Storm Hits: When does Tom believe the storm will hit? Why does Tom believe when it does hit, it will be worse than The Great Financial Crisis? How will VCs respond when the storm hits? How will it impact their investing cadence? How will LPs respond when the storm hits? Will they cut back their manager commitments? Does Tom have hope that their will be a new class of LPs in this new economic cycle? 4.) The Rounds That Happen When The Storm Hits: Does Tom believe we will see a wave of down rounds when the storm hits? Why are they less common than people think? In the eye of the storm, will we see further layoffs? Will we see firesales? Will we see a tidal wave of shutdowns? Will large multi-stage funds with huge amounts of dry powder change their deployment pace? The Survival Guide for the Storm: 1.) Raise Now: Why does Tom believe that startups should raise now, not later? What amount of runway should they raise for in this environment? 2.) Cut, Cut and Cut Some More: What amount of runway should startups be cutting to get to? How will this impact marketing spend? Why are your marketing dollars more powerful now than ever before? 3.) Focus on Survival Not Valuation: What does Tom mean by this? How can founders gain leverage with VCs when raising today? How can founders instil a sense of urgency in their raise with investors? 4.) Bring on Operators with Experience: Why would operators with experience join a struggling startup? Will operators with experience not have a flight to safety and stay at their well-paid FANNG role? Does this potential operator not shorten runway even further as they are often expensive? 5.) Unit Economics over Growth: How can founders show investors a superior profile of unit economics moving forward? Do investors not want both unit econ and growth today? 6.) Play Your Cards Right and Then Go on Offense: How does Tom advise founders on the right time to go on offense? 7.) Be Decisive, Half Measures Rarely Succeed: How does Tom define a half-measure? What is so wrong with half-measures?

Steve Pagliuca is a Senior Advisor at Bain Capital, the firm he joined in 1982 and as a Managing Director of Bain Capital, he has helped build the firm into one of the world’s leading investment companies with over $160 billion in assets under management. Steve is also a Managing Partner and Co-Owner of the World Championship Boston Celtics Basketball franchise. Steve is also co-owner and co-chairman of the Serie A professional football club, Atalanta Bergamasca Calcio. If that was not enough, Steve currently, serves on the Board of Directors of Burger King, Gartner Group, HCA, Warner Chilcott, and FCI. Huge thanks to Moshe @ Shrug Capital for making the intro. In Today's Episode with Steve Pagliuca We Discuss: 1.) From Duffel Bags at Duke to Buying Sports Teams: How Steve went from having a single duffel bag arriving at Duke University to entering the world of private equity with the founding of Bain's PE funds? Did Steve always know he would be successful? What does Steve think about the importance between luck and timing? How did Steve's mother impact how he approaches parenting and self-belief with his children? 2.) Buying Sports Teams: Not So Different to Companies: When buying and running a sports team, what is the same, and what is different from buying and running a company? What is Steve's biggest advice to new owners of sports teams? What are the single biggest mistakes sports team owners make when they buy a team? What happened with the Chelsea bid? Why did Steve lose? How did debt change the deal? 3.) The Future of Sports Ownership: Why does Steve believe we have seen a massive rise in American and private equity buyers of both global sports teams but also European sports teams? How has "new media" changed the inherent value that can be placed on a team? Why does it change the value? Which forms of "new media" are most important? How much further can the value of these sports teams increase? Does this massive increase in the price and assets of certain clubs not lead to a massive inequality in sports? What can be done to prevent this imbalance? 4.) Steve Pagliuca: The Person and Capital Allocator: What is the single best investment advice Steve has ever received? How does Steve think about his relationship to wealth today? How has it changed over time? What does it take to have an amazing marriage and be at the top of your profession? What were 1-2 elements that made Bain able to scale to the proportions of AUM that they have done? What would he have done differently?  

Ariel Cohen is the Co-Founder and CEO @ Navan (formerly TripActions), the #1 travel management super-app used by over 8,000 companies. Ariel has raised over $2BN for Navan from some of the best including a16z, Zeev Ventures, Lightspeed, Greenoaks, and Elad Gil. Prior to TripActions, Ariel co-founded streamOnce, a business multimedia integration platform that was successfully acquired by Jive Software, where Ariel had previously served in a senior position following his time at Hewlett-Packard. In Today's Episode with Ariel Cohen We Discuss: 1.) Why Education is Outdated and Wisdom to People Entering the Working World: Why did Ariel not really attend many classes when he was a student? What would be his biggest advice to young people leaving school today? Where would he focus? Why does Ariel believe that traditional education is more outdated now than ever before? 2.) Why SAP and Salesforce Will Die: Why does Ariel believe that SAP and Salesforce have not innovated for a decade? Why does Ariel believe that Slack is a disaster inside of Salesforce? What are the single biggest advantages that startups have over these large incumbents? What can startups do to retain innovation and speed as they scale into becoming an incumbent? Why are the best founders willing to kill their own projects? 3.) Growing a Business 3x and Raising at a $9.2BN Valuation in COVID: How did Ariel grow the business 3x with all travel being banned? What were the tactics to blitz scaling during COVID? How did Ariel approach his investors for a new round in the middle of COVID? How did he get such a high price in the midst of a global pandemic? What is the bull case for how Navan can be a $40BN company? 4.) Margins Matter: Gaining Leverage Through Additional Margin: With Navan's 80% margin, they have 30% higher margins than other competitors, how do they have such high margins? With the additional 30%, how does Ariel plan to scale Navan's reach and use the margin to do so? How does OpenAI play a role in helping Navan increase its margin even further?

Orlando Bravo is a Founder and Managing Partner of Thoma Bravo. He led Thoma Bravo’s early entry into software buyouts and built the firm into one of the top private equity firms in the world. Today, Orlando directs the firm’s strategy and investment decisions. Orlando has overseen over 420 software acquisitions conducted by the firm, representing more than $235 billion in transaction value. Forbes named him "Wall Street’s best dealmaker" in 2019, and he was dubbed "Private equity’s king of SaaS" by the Financial Times in 2021. In Today's Episode with Orlando Bravo We Discuss: 1.) From Puerto Rico Roots to Wall Street's Best Dealmaker: How did Orlando come to co-found Thoma Bravo? What was that a-ha moment for him? Orlando mentioned 2 mentors that shaped how he thinks, who were they? What are his single biggest lessons from those mentors? What does Orlando know now that he wishes he had known when he started his career? Why does Orlando disagree with setting timelines in life? Why does it not help? 2.) The Secret to Success in Value Investing: What is good value investing today? What is it not? What three things does Orlando look for when doing a deal and acquiring a company? Why is every company in the world worth its future cash flows? How important is price today? How does Orlando reflect on his own price sensitivity? Many suggest Coupa and Anaplan were extremely expensive. How does Orlando respond and defend the prices he paid for companies in 2020-2022? 3.) WTF is Happening In Markets Today: How does Orlando reflect on where the market is today? Is this the new normal? How does Orlando expect the market to change over the next 12 months? Why does Orlando believe that the best companies win in the worst times? Is this the result of quantitative easing on behalf of central banks? Who is to blame? How does Orlando balance the mindset of his team between risk on and taking advantage of lower prices in market but also not catching a falling knife? 4.) Orlando Bravo: The Leader, Father and Husband: What is Orlando's biggest fear in investing? How has this changed over time? How does Orlando reflect on his own relationship to money today? How has that changed? What are Orlando's biggest parenting lessons from his mother? Why does Orlando believe that for most people, their late twenties are their toughest? How does Orlando instill the same drive and ambition in his children that he had, despite very different financial profiles growing up? How does Orlando maintain being at the top of his game in his profession but also being a great husband? What is the secret to a happy marriage? Items Mentioned in Today's Episode: Orlando's Fave Book: The Power of Now: A Guide to Spiritual Enlightenment

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. Before Calendly, Annie led Glassdoor’s product vision and user experience, managing a 70-person product and design org.  Shreyas Doshi is an investor, advisor, and all-around product OG. Most recently Shreyas spent over 5 years at Stripe where he was Stripe’s first PM Manager and helped grow the PM function (from ~5 to more than 50 people). Before Stripe, Shreyas was a Director of Product Management @ Twitter. David Lieb is one of the product OGs of the last decade. As the founder of Bump David pioneered how over 150M users shared data, contacts and more before the company was acquired by Google. At Google, David took this one step further by creating Google Photos. Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for Hewlett-Packard, Netscape Communications, and eBay. Aparna Chennapragada is the former CPO @ Robinhood, revolutionizing consumer finance with commission-free investing. Prior to Robinhood, she spent an incredible 12 years at Google, most recently as VP and GM for Consumer Shopping and also as the lead AR and Visual Search products.  Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and one of the most popular newsletters on Substack.  For the last 7 years, Kayvon Beykpour has been at Twitter where he led all of the teams across Product, Engineering, Design, Research, and Customer Service & Operations. Kayvon came to Twitter through Periscope, the live broadcasting app he founded that was acquired by Twitter in 2015. Scott Belsky is an entrepreneur, author, investor, and currently serves as Adobe’s Chief Product Officer. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. In 2006, Scott founded Behance, and served as CEO until Adobe acquired Behance in 2012. In Today's Episode on How to Hire a Product Manager, We Discuss: 1.) When to Hire Your First PM: What are the core signs that the founder must delegate and hire their first PM? What are the first things that are breaking when you do not have one but need one? How does the timing of the first PM differ when comparing B2B vs B2C? 2.) What is the Right Profile: What should founders look for in this first PM hire? What traits make the best? What are the biggest red flags in the personalities and styles of potential candidates? Should they have experience in the product domain they are entering? What are the single biggest mistakes founders make when analyzing the resumes of potential PM candidates? What should they look for in their resume? 3.) The Hiring Process: How To Hire a Product Manager How do we structure and run the hiring process for this person? What tests can we do to understand if they have the skill set we need for the role? How do we structure a hiring panel to make this process more effective? What are the biggest mistakes founders make in the hiring process for PMs?

Alex Bouaziz is the Co-Founder and CEO @ Deel, the all-in-one platform made to simplify all things HR, built for global teams near and far. In the last year alone, Alex has scaled Deel from $57M in ARR to $295M, EBITDA positive since Sept 2022, 85%+ gross margins, and over $5BN paid out to 250,000 people. Alex has raised over $679M with Deel, pricing the company at the last round at $12.1BN. Investors in the company include a16z, Spark Capital, Coatue, and many more. In Today's Episode with Alex Bouaziz We Discuss: 1.) From Student in London to Decacorn Founder: How Alex made his way into the world of startups and how he came up with the idea for Deel? Did Alex always know he would be successful when he was growing up? What does Alex know now that he wishes he had known when he was starting? 2.) The Importance of Execution: How important does Alex think speed of execution is for startups? What can startups do to deliberately increase their speed of execution? How does Alex think about the dilemma of losing quality with speed? What does Alex think you do need to go slow on to ensure it is perfect? How does Alex think about focus and prioritisation today with Deel? 3.) Scaling to $295M in ARR in 3 Years: When did Alex know he had true product-market fit with Deel? How did Alex use a 50-person Whatsapp group to both determine product market fit and to navigate product direction for the company? What was the key to Deel's blitz scaling strategy? What worked? What did not work? How did Alex hire 2,000 people in such a short space of time? What broke first in the organisation? How could they have prevented it? 4.) Secondaries, Angel Investing and Wealth Management: How much did Alex take out in secondaries in the last round of funding? How did Alex determine how much cash to allocate to angel investing? Why does Alex believe most founders make poor angel investments when they have cash? What have been Alex's biggest lessons from investing? How has it changed how he operates? Why should all founders be super transparent in investor updates?

Hunter Walk and Satya Patel are Co-Founders and Partners @ Homebrew, one of the leading seed funds of the last decade. Following 10 years of stellar returns with investments in the likes of Chime, Plaid, Gusto and many others, they decided to not accept any further LP capital and to only invest their own money moving forward through Homebrew Forever. In Today's Discussion on Homebrew We Breakdown: 1. ) The Foundings of a Great Partnership: What was the moment when Hunter and Satya decided they were going to go out and raise their first fund with Homebrew I? What are the core principles that all founding partners need to align on before they start a firm together? What questions should they ask of each other? Why does being independently wealthy coming into a partnership make the partnership easier and more efficient to operate? What changes when the partners have money already? 2.) What Changes When Moving From LP Dollars to Personal Capital: Why did Hunter and Satya decide to not raise any further capital from external LPs? Asset allocation-wise, how did they determine how much is the right amount to set aside for the first 2 years of investing? How many investments do they want to make with that cash? How does investing their personal capital change their deployment pace and cadence? How does it change their approach to reserves management and follow-on financing? How does it change their approach to pricing? How price sensitive are they today? 3.) Analyzing the Seed Landscape Today: Why do Hunter and Satya not think that a $100M seed fund is enough to properly execute a world-class seed strategy today? Who is their competition with the new strategy? How does it change their relationship with large multi-stage funds? How does it change their relationship with seed funds? Do they agree that the last generation of sub $20M micro-funds will not raise another fund in this cycle? How did their entrance impact the seed landscape over the last few years? Why are LPs also to blame for many of the original seed managers raising larger and larger funds? 4.) Companies: Money and People are The Problem: Why has too much money been such a problem for many Homebrew portfolio companies over the last few years? How has too much money changed their execution plans? What happens to the "living dead" companies with many years of runway but no product market fit? Who does this market cater to well? Who will thrive in this market? What have people forgotten about both startups and venture in the last 2 years that we have to remember? Why is this generation so entitled and expectant? Why are startups not a get-rich-quick scheme?

Cliff Obrecht is the Co-Founder & COO @ Canva, the free-to-use online graphic design tool that makes it easy for anyone to design anything from presentations to videos and social media. Cliff and Mel have scaled Canva to over 60 million monthly users, 2,000 employees, and 500,000 teams from companies like Intel and Zoom using Canva. During this incredible growth journey, they have raised over $580M with their last round valuing the company at over $40BN. In Today's Episode with Cliff Obrecht 1.) From Teacher to Billionaire Tech Founder: How did Keith make his way into the world of tech with his founding of FusionBooks? What did the process with FusionBooks teach him about how to run Canva? How did the early fundraising days for Canva go? Why does Cliff think they got over 100 no's? What are Cliff's biggest pieces of advice for founders today, not in Silicon Valley, looking to raise from Silicon Valley VCs? 2.) Scaling to $40BN: The Biggest Lessons: What does Cliff mean when he says the secret to successful hiring is looking for "distance traveled"? How does he determine this in the interview process? What have been some of the single biggest lessons in what it takes to acquire the best talent? What are some of the biggest mistakes Cliff has made in talent acquisition? How has his process changed as a result? What do Canva do to get the best operators as advisors in the company? How do they compensate these advisors? What does Cliff advise founders on how to do the same? 3.) The Art of Deal-Making: How does Cliff think through what makes a "good deal"? How does he approach negotiation? What are the biggest mistakes founders make when negotiating and doing deals? What have been Cliff's biggest lessons on successful investor relations over the years? How does Cliff and Canva approach acquisitions? What do they look for? What is their process? Why do most tech companies approach acquisitions the wrong way? 4.) Cliff Obrecht: Money, Fatherhood and Marriage: How does Cliff analyze his relationship to money today? How much money is enough? How has his relationship to money changed over time? Why have Cliff and Mel given away over $10BN to their foundation? Why is philanthropy so hard to do effectively? Why would Cliff hate for his children to be brought up in excess wealth? What does "great fatherhood" mean to Cliff? What are the most challenging aspects of parenting? What are the secrets to a happy marriage? How does co-founding a company with your other half work well? How does it work poorly?

Stevie Case is the CRO @ Vanta where she oversees Vanta’s go-to-market team to support the company’s rapid growth. Prior to joining Vanta, Stevie was Vice President of Mid-Market Sales at Twilio, joining as one of their first account executives, Stevie helped to grow the sales team from a dozen to over 1,000 team members and played a pivotal role in establishing Twilio’s enterprise business with key Fortune 500 customers, generating more than $400 million in annual recurring revenue. If that was not enough, Stevie is also a Founding Operator @ Coalition Network and a prominent angel investor. In Today's Episode with Stevie Case We Discuss: 1. ) From World's First Pro Female Gamer to CRO: How did Stevie make her way from pro gamer to CRO? How did her career in gaming make her a better CRO and sales leader? In her early sales career, how did being a single mother with a child impact her approach to sales? What can founders do to make workplaces more inclusive for parents today? 2.) Enterprise or PLG: Which One To Choose: Why does Stevie believe it is not right to do both PLG and enterprise at the same time for startups? How can startups and sales teams move into enterprise selling gradually through testing and without committing a significant budget to an enterprise sales team? How do founders know when is the right time to move from PLG to enterprise? What are the signs? 3.) The Mythical Sales Playbook: How does Stevie define the term "sales playbook" today? What is it not? Should the founder be the person to create the sales playbook? If not them, then who? When is the right time to make your first sales hire? When is the wrong time? 4.) Mastering the Hiring Process in Sales Recruits: How should we structure the interview process for new sales reps? What is the right profile for these first sales hires? How do the best sales talent answer questions and perform in interview processes? How can we really test for grit and curiosity in the interview process? What are the single biggest mistakes founders make when hiring for sales? 5.) Discovery, Discounting, Deal Velocity: With sales cycles being so long, how do you know if enterprise sales reps are good? What is the difference between good discovery vs bad discovery? Should founders engage in discounting to get deals over the line? When does it work?

Albert Wenger is a managing partner at Union Square Ventures, one of the most successful venture firms of the last decade with a portfolio including Coinbase, Twitter, Twilio, Etsy, and many more. Before joining USV, Albert was the president of del.icio.us through the company’s sale to Yahoo and an angel investor (Etsy, Tumblr). He previously founded or co-founded several companies, including a management consulting firm and an early-hosted data analytics company. In Today's Episode with Albert Wenger We Discuss: 1.) From Failed Startup Founder to Leading VC: How Albert transitioned from being a failed entrepreneur to being one of the most respected venture investors with USV today? What were the clear signs for Albert that he was not a good entrepreneur? Why does Albert believe this downturn is different compared to the dot-com bubble? Why was there more hope and promise coming out of the dot-com bubble? 2.) Income Inequality, The Rise of Depression & The Role of Politics: Why is income and wealth inequality more concerning than ever? Why does Albert believe universal basic income is the right solution? Why is mental health worse than ever? What can be done to improve this? Why are our politicians failing us? What should our politicians be doing? How does the rise of Trump show us what society is looking for in politicians? 3.) Climate Change: Misnomers, Developing Countries, Civil Disobedience: What are the single biggest misnomers people have when it comes to climate change? How can we shift spending on climate change solutions from 5% of GDP to 50%? Is that possible? Why do developing nations have an advantage when implementing climate change solutions over more developed economies? Why is civil disobedience the right course of action to ensure society is on a path to change our approach to climate change? 4.) Crypto and Central Banks: The Future of Finance: Why does Albert believe that over the past few years, for many, crypto was a good hedge against inflation? How damaging does Albert believe SBF and FTX will be to crypto in the long term? How does Albert evaluate the potential for governments to create a "central bank digital currency"? What would Albert like to see in a potential currency like this? How could stable coins be the solution to this? What is Albert fearful of with central bank digital currencies? Why does Albert believe now is the best time to be investing in crypto? 5.) The Future of Social Media: Twitter & TikTok: What does Albert believe is wrong with Twitter today? Why was the blue check mark such a mess? What does Albert believe Elon should do with Twitter from this point on? How should Elon deal with the debt providers he has? What happens to Twitter moving forward? Why is it so hard to kill? What is the future of TikTok? Will it be banned in the US? How concerned should the consumer be concerning their data being shared with the Chinese Government?

Mike Cessario is the Founder and CEO @ Liquid Death, the man hacking the healthy beverage market with the first hilarious water brand. It is working, Liquid Death's latest valuation was over a staggering $700M and Mike has raised over $200M since founding the company from the likes of Science Inc. Away's Jen Rubio, Dollar Shave Club's Michael Dubin, Swedish House Mafia and Tony Hawk to name a few. Prior to founding Liquid Death, Mike was in the advertising industry at a number of dirrect firms including VaynerMedia. In Today's Episode with Mike Cessario We Discuss: 1.) From Canned Water to $700M Business: How did rockstars' hydration problems lead to the founding of Liquid Death? How did growing up with guns and heroine needles around him at school, impact how Mike sees the world today? What is he running from? What is he running towards? Everyone said, "canned water, that is a stupid idea". What does Mike tell to all entrepreneurs who are told their idea is stupid? How does Mike advise on picking your idea? 2.) How to Build a Truly Great Brand: What does the term "brand" mean to Mike? What does he mean when he says, "truly great brand transcends functional value"? What are the single biggest mistakes Mike sees founders make today on branding? Why does Mike believe people will always hate your brand, if it is good? What are the biggest brand mistakes Mike has made with Liquid Death? What brand does Mike most respect and admire? Why that brand? 3.) Marketing: The Secret to Reaching Millions of People with Little Budget: How does the Liquid Death team come up with the ideas they have for content? Why does Mike believe the label "storytelling" is kinda BS? Why does Mike believe people will always hate your marketing? What was Mike's biggest lesson from their Superbowl commercial with kids drinking Liquid Death, looking like beer? How does Mike decide which channel to prioritise? How has the rise of TikTok and short form video changed their approach to content? How does Mike approach resource allocation for new pieces of content? Do they spend big on few bits of content or spend little on many and see what works?  

Hila Qu is one of the leading growth execs of the last decade. Hila helped scale Acorns from 1 million to 5 million users as their VP of growth. Hila then joined GitLab, where she launched their PLG motion (on top of an established sales motion), and built their first-ever growth team. Today Hila is an advisor to amazing companies like Replit and funds like Mucker Capital, Openview and First Round Capital. In Today's Episode with Hila Qu We Discuss: 1.) From Biology and Explosions to Growth: How Hila made her way into the world of growth with growthhackers.com? What are 1-2 of the biggest takeaways from her time with Acorns and Gitlab? How do B2B growth orgs compare to B2C growth orgs? What is different? What is the same? 2.) WTF is Growth? When? How & Why: How does Hila define growth today? What is it not? When is the right time for early-stage founders to hire their first growth hire? Why does Hila always look for data analysts in this first growth hire? From a data standpoint, what should founders have ready and accessible for their first growth hire to have access to and learn from? Is Google Analytics enough? 3.) Hiring Your First Growth Hire: How should early-stage founders structure the hiring process for the first growth hire? What do the best growth job descriptions include? What do they not include? Once applications are in, how does Hila advise founders screen for the best candidates? How should founders structure the interview process post-screening? What are the must-ask questions? Who is involved in the interview process? What are some red flags? 4.) The Master of Onboarding: What should new growth hires want to achieve in the first week? What should they want to complete in the first month? In the first quarter, what do the best candidates have completed? What can founders do to set their growth hires up for success in the best way at this time? 5.) Growth Models, North Stars, Activation and Onboarding and Key KPIs: What really is a growth model? How do founders and growth teams create one? How does Hila advise founders on how to pick the right North Star Metric to focus on? Why are activation and conversion Hila's two favorite growth metrics? What are growth loops? What are growth funnels? How do they work together?

Jeff Jordan is a General Partner @ a16z where he serves on the boards of Airbnb, Incredible Health, Instacart, Lookout, and Pinterest, just to name a few. Before a16z, Jeff was CEO OpenTable, where he led the company during a period of hyper-growth and oversaw its IPO. Prior to OpenTable, Jeff was Senior VP and General Manager of eBay North America where he oversaw eBay's early growth into one of the Internet's leading commerce brands. In this role, he drove the successful acquisitions of PayPal and Half.com and went on to become President of PayPal, where he was responsible for establishing the company as the global standard for online payments.   In Today's Episode with Jeff Jordan We Discuss: 1.) From Taking Opentable Public to Being a GP @ a16z: What led to Jeff making the jump from CEO @ Opentable to becoming a GP at a16z? How does Jeff believe his operating career impacted how he thinks and acts as an investor today, both positively and negatively? What is his 1 biggest learning from eBay and then Opentable that has really shaped his mindset today as an investor? How did those experiences impact what he looks for in companies? 2.) The Two Core Features To Look For in Marketplaces: Fragmentation of supply side: Why does Jeff look for fragmented supply sides? Does this not take longer and is more expensive? How fragmented is fragmented enough? What are the most common reasons founders fail to acquire a fragmented supply side? Intelligent Lead Generation: What does Jeff really want to see in the way that new marketplaces acquire their customers? How does this change with the rise of TikTok and short-form video? What are some other really core features or traits that excite Jeff when he sees them in an early marketplace? What are some massive red flags for Jeff when he sees them early? 3.) How to Acquire and Retain the Demand Side of a Marketplace: Messaging and Brand: What are the biggest lessons Jeff has on how to craft the messaging of a marketplace to make it resonate with the target consumer? What are Jeff's biggest lessons from working with Brian Chesky on how they craft their messaging at Airbnb? What works? What does not work? Perfect Customer Cohorts: What does Jeff most want to see when examining prospective marketplace investment cohorts? What do the best have? What is the sign of a truly retained user in a marketplace? What is a good date duration to measure retention against? What are the biggest mistakes founders make presenting their cohorts? Lessons from Instacart: What are Jeff's biggest lessons from being on the Instacart board on cohorts? What makes good cohorts? How cohorts can seem bad but be good? 4.) Growth vs Profitability, CACs and LTV: Uber, OfferUp, Instacart, Deliveroo, respectfully, the level of profits these businesses are able to drive is questionable, why does Jeff believe marketplaces are good investments still? Many marketplaces start with poor unit economics, how does Jeff think about having the mental plasticity to project out to a time when unit economics could be better? Does Jeff pay attention to CACs at all? When are they important? When are they not? How can they be misleading? What is the best way for founders to present their CACs? 5.) It's Time to VC: Jeff Jordan: The Board Member What are the single biggest misalignments between VCs and their founders? How would Jeff describe his style of board membership today? How has it changed with time? What is the best way to deliver hard feedback as a board member? What are the biggest mistakes board members make? What does Jeff advise young board members today? What are the single best and worst changes that have happened at a16z in the last 24 months?

The question is: "are VCs still investing?". Today we are joined by Jason Lemkin; one of the OGs of SaaS of the last decade. As the Founder of SaaStr, he has inspired more SaaS founders than one can imagine building “The World’s Largest Community for Business Software.” Jason also invests out of the $100M SaaStr Fund and in the past Jason has led rounds into TalkDesk, Pipedrive, Algolia, Gorgias, Salesloft, and many more incredible companies. Prior to founding SaaStr, Jason was the Co-Founder of Echosign, an early e-signature business, funded by Emergence Capital and that was acquired by Adobe for $100M. In Today's Episode on "Are VCs' Still Investing" We Discuss: 1. What Does it Take To Get Funded Today: Early-Stage: How has what VCs want in early-stage investments changed in this new environment? Should startups prioritize growth? Profitability? Capital efficiency? How long a runway is sufficient enough for founders to feel comfortable? Why does Jason believe most founders are still deluded that they are fundable? Growth Stage Companies: Is the growth stage totally dead? What will we see happen to all the companies that raised $50M+ at large valuations that have very little revenue? Why does Jason believe that any operator who joined a $BN company in the past few years will not make any money on their equity? What should they do now? Will we start to see down rounds and structured rounds at the growth stage? If so, when? Public Markets: Why does Jason believe this is a time unlike any he has seen before? Are we in full recession now in Jason's mind? In Dec 2023, will this be better or worse? Which are the most under-priced assets in the public markets today? Why does Jason believe VCs investing in public markets are losers? 2. Micro Funds Will Be Decimated and LP Behaviour in 2023 Why does Jason believe that micro-funds in 2023 will be decimated and unable to raise new funds? How will the majority of LPs approach new fund investments? How will LPs approach re-investing in their existing managers? How has what they need to see changed? 3. Marketing and Sales: We Need To Change Budgets and Targets How should CEOS be changing their marketing budgets in 2023? What are the single biggest mistakes CEOs are making in this downturn with regard to their marketing budget? How do sales targets need to be amended in the face of changing buying patterns? How do the best sales and marketing leaders respond to these changing budgets and targets? How do the worst respond?        

How To Raise a Venture Capital Fund Over the last 4 years, I have raised around $400M across different vehicles from many different types of investors. Today I am going to break down the early stages of how to raise a venture capital fund and then stay tuned for a follow-up to this where we will break down a fundraising deck for a fund, what to do, what not to do etc. But to the first element.  Your Fund Size is Your Strategy: The most important decision you will make is the size of fund you raise. So much of your strategy and approach will change according to your fund size target (LP type, messaging, documentation, structure etc). Remember, your fund size is your strategy. If you are raising a $10M Fund, you are likely writing collaborative checks alongside a follower, if you are raising a $75M fund, you will likely be leading early-stage seed rounds. These are very different strategies and ways of investing.  MISTAKE: The single biggest mistake I see fund managers make is they go out to fundraise with too high a target fundraise. One of the most important elements in raising for a fund is creating the feeling of momentum in your raise. The more of the fund you have raised and the speed with which you have raised those funds dictate that momentum. So the smaller the fund, the easier it is to create that heat and momentum in your raise. LESSON: Figure out your minimum viable fund size (MVFS). Do this by examining your portfolio construction. In other words, how many investments you want to make in the fund (the level of diversification) and then alongside that, the average check size you would like to invest in each company. Many people forget to discount the fees when doing this math and so the traditional fund will charge 2% fees per year and so across the life of the fund (usually 10 years), that is 20% of the fund allocated to fees.  Example: We are raising a $10M Fund.  20% is allocated to fees for the manager and so we are left with $8M of investable capital.  A good level of diversification for an early-stage fund is 30 companies and so with this fund size, I would recommend 32 investments with an average of $250K per company. That is the $8M in invested capital. Big tip, I often see managers raising a seed fund and are only planning to make 15 investments, this is simply not enough. You have to have enough diversification in the portfolio if you are at the seed stage. No one is that good a picker. Likewise, I sometimes see 100 or even 200 investments per fund, this is the spray-and-pray approach, and although works for some, your upside is inherently capped when you run the maths on fund sizes with this many investments.  A big element to point out in this example is we have left no allocation for reserves. For those that do not know, reserves are the dollars you set aside to re-invest in existing portfolio companies. Different funds reserve different amounts, on the low end there is 0% reserves and on the high end some even have 70% of the fund reserved for follow-on rounds.  In this example, given the size of the fund being $10M with a seed focus, I would recommend we have a no-reserves policy. Any breakout companies you can take to LPs and create SPVs to concentrate further capital into the company. This is also better for you as the manager as you then have deal by deal carry on the SPVs that are not tied to the performance of the entire fund. So now we know we know $10M is our MVFS as we want to make at least 30 investments and we want to invest at least $250K per company. Great, next step.  Set a target that is on the lower end, you can always have a hard cap that is significantly higher but you do not want the target to be too far away that LPs question whether you will be able to raise the fund at all. This is one of the biggest reasons why many do not invest in a first time fund, they are unsure whether the fund will be raised at all.  The Team: Alongside the size of the fund, the team composition is everything, simply put, LPs like managers who have invested in the stage you are wanting to invest in moving forward. They like to see track record. IMPORTANT: I see so many angels write checks into breakout Series B companies and then go out and try and raise a seed fund with this as their track record. Do not do this, this does not prove you are a good seed investor but merely shows you have access at the Series B. These are very different things.  With regards to track record, in the past, TVPI or paper mark-ups were enough, now there is a much greater focus on DPI (returned capital to investors). LPs want to see that you have invested before at that stage and they also want to see that the team has worked together before. You want to remove the barriers to no. If you have not worked with the partners you are raising with before, LPs will have this as a red flag, and as team risk, it is that simple.  Navigating the World of LPs (Limited Partners) The size of the fund you are raising will massively dictate the type of LPs that will invest in your fund.  MISTAKE: You have to change your messaging and product marketing with each type of LP you are selling to. A large endowment fund will want a very different product to a Fund of Funds.  Example: If you are a large endowment, you will invest in early funds but you want the manager to show you a pathway to them, in the future, being able to take not a $10M check but a $50M check from the endowment. Whereas the Fund of Funds will likely want you to stay small with each fund. So when discussing fund plans, it is crucial to keep these different desires in mind.   If you are raising a $10M fund, you will be too small for institutional LPs and will raise from individuals and family offices. An LP will never want to be more than 20% of the LP dollars in a fund and so the size at which an institutional LP (really the smallest fund of funds) would be interested is when you raise $25M+ and they can invest $5M. Generalisation but a good rule of thumb to have.  LP Composition of Your Fund: Speaking of one LP being 20% of the fund dollars, it is helpful to consider the LP composition you would like to have for your fund. The most important element; you want to have a diversified LP base. A diversified LP base is important in two different forms: No LP should be more than 20% of the fund at a maximum. That said you do not want to have so many investors in your fund it is unmanageable. LPs need time and attention and so it is important to keep that in mind when considering how many you raise from. Some LPs will want preferred terms or economics for coming into the first close or being one of the first investors, if you can, do not do this. It sets a precedent for what you will and will not accept and then for all subsequent investors, they will want the same terms and rights.  You want to have a diversification of LP type (endowments, fund of funds, founders, GPs at funds etc). Why? In different market cycles, different LPs will be impacted and so if you only raise from one LP type, if a market turns against that LP class, then your next fund is in danger.  Example: We will see the death of many mico-funds ($10M and below). Why? The majority raised their funds from GPs at larger funds and from public company founders. With the changing market environment, most GPs are no longer writing LP checks and most public market founders have had their net worths cut in half by the value of their company in the public market and so likewise, are no longer writing LP checks. In this case, the next funds for these funds will be in trouble as their core LP base is no longer as active as they used to be. We are seeing this today.  Prediction: 50% of the micro-funds raised in the last 2 years will not raise subsequent funds.   Going back to the question of diversification, my preference and what we have at 20VC, the majority of dollars are concentrated from a small number of investors. Of a $140M fund, we have $100M invested from 5 large institutions. These are a combination of endowments, Family Offices, a High Net Worth Individual and a Fund of Funds. The remaining $40M originates from smaller institutions or individuals, for us we have over 50 making up that final $40M. For me, I really wanted to have a community around 20VC Fund and so we have over 40 unicorn founders invested personally in the fund as LPs.  Bonus Points: The best managers select their LPs to play a certain role or help with a potential weakness the manager has. For example, I was nervous I did not have good coverage of the Australian or LATAM startup market and so I was thrilled to add founders from Atlassian, Linktree, Mercado Libre, Rappi and Nubank as LPs to help in regions where I do not have such an active presence. If you can, structure your LP base to fill gaps you have in your ability. Status Check In: Now we know our minimum viable fund size, we know the team composition we are going out to raise with, we know the LP type that we are looking to raise money from and we know how we want our desired fund cap table to look.  Now we are ready to move to the LPs themselves.  Fill Your Restaurant with Friendlies: As I said, the appearance of your raise having heat and momentum is important.  Mistake: The biggest mistake I see early fund managers make is they go out to large institutional investors that they do not have an existing relationship and spend 3-4 months trying to raise from them. They lose heat, they lose morale and the raise goes nowhere. Whatever fund size you are raising, do not do this. Fill your restaurant with friendlies first. What does this mean? Go to anyone you know who would be interested in investing in your fund and lock them in to invest. Create the feeling that progress is being made and you have momentum.  BONUS POINTS: The best managers bring their LPs with them for the fundraise journey. With each large or notable investor that invests in your fund, send an email to the LPs that have already committed to let them know about this new notable investor. This will make them feel like you have momentum, they are in a winner and many will then suggest more LP names, wanting to bring in their friends.  MISTAKE: Do not set a minimum check size, some of the most helpful LPs in all of my funds have been the smallest checks. Setting a minimum check size will inhibit many of the friendlies from investing and prevent that early momentum.  The bigger the name the incoming investor has the better. You can use it for social validity when you go out to raise from people you know less well or not at all. Different names carry different weight, one mistake I see many make is they get a big name invested in their fund but it is common knowledge to everyone that this LP has done 200 or 300 fund investments, in which case, it does not carry much weight that they invested in your fund. Be mindful of this as it can show naivety if you place too much weight on a name that has invested in so many funds.  Discovery is Everything: The world of LPs is very different to the world of venture. 99% of LPs do not tweet, write blogs or go on podcasts. Discovery is everything. When I say discovery I literally mean finding the name of the individual and the name of the organization that is right for you to meet.   This can take the form of several different ways but the most prominent for me are: The Most Powerful: Create an LP acquisition flywheel. What do I mean by this? When an LP commits to invest in your fund. Say to them, “thank you so much for your faith and support in me, now we are on the same team, what 3 other LPs do you think would be perfect for the fund?” Given they have already invested, they already believe in you and so 90% of them will come back with 3 names and make the intro. Do this with each LP that commits and you will create an LP acquisition flywheel.  Bonus Point: The top 1% of managers raising will already know which LPs are in the network of the LP that has just committed and will ask for those 3 specific intros. They will then send personalized emails to the LP that has just committed. The LP is then able to forward that email to the potential LP you want to meet. You want to minimize the friction on behalf of the introducer and so writing the forwardable email is a great way to do this.  The Most Likely to Commit: LPs are like VCs. When one of their portfolio managers makes an intro and recommendation to a potential fund investment, they will place a lot more weight on it than they would have otherwise. So get your VC friends to introduce you to their LPs, it is that simple. Remember, you have to remove the friction from the introducer. So, make sure to send the email they can forward to the LP. Make this personalized and concise. Mistake: Many VCs do not like to introduce other managers to their LPs as they view it as competition. This is moronic. If the manager asking for the intro is really good, they will raise their fund with or without your intro. If they are not good, then you can politely say it would not be a fit for your LP and move on. Do not be too protective of your LPs from other managers. The Cold Outbound: I am not going to lie cold outbound for LPs is really hard. Here is what I would suggest: Pitchbook: It is expensive and many cannot afford it but if you can, it is worth it for LP discovery. They have thousands of LPs of different types on the platform all with their emails and contact details. Those are less useful as a cold email to an LP is unlikely to convert but just finding their names and the names of their organization is what is important. You can then take that to Linkedin to then find the mutual connections you have with that person and ask for a warm intro.  Linkedin: Many LPs have the funds that they have invested in on their Linkedin profiles with the title “Limited Partner”. If they are invested in a fund that is aligned with the strategy that you are raising for, there is a strong chance they might be a fit. For example, I invest in micro-funds and have invested in Chapter One, Scribble, Rahul from Superhuman and Todd’s Fund, and Cocoa Ventures, so you see this and see I like sub $25M funds with a specific angle.  Clearbit: Often you will know the name of the institution but not the name or position of the person within the institution that you are looking to raise from. Download a Google Chrome Plugin called Clearbit. With Clearbit you can simply insert the URL for the organization you would like to speak with and then all the people within it will appear and you can select from title and their email will be provided. Again, if you do not want to cold email, you now have their name which you can take to your community, to ask for the intro.  MISTAKE: LPs invest in lines, not dots. Especially for institutional LPs, it is rare that an institution will meet you and invest in you without an existing relationship and without having followed your work before. A mistake many make is they go to large institutions and expect them to write a check for this fund, it will likely be at best for the fund after this one or most likely the third fund. This does not mean you should not go to them with your first fund but you should not prioritize them and you should not expect them to commit. I would instead go in with the mindset of we are not going to get an investment here, so I want to leave the room understanding what they need to see me do with this first fund, to invest in the next fund. The more detailed you can get them to be the more you can hold them to account for when you come back to them for Fund II.  Example: If they say, we want to see you are able to price and lead seed rounds and we are not sure you can right now. Great. Now when you come back to them in 12 months' time, you can prioritize the fact that you have led 80% of the rounds you invested in, and their core concern there has been de-risked. In terms of how I think about LP relationship building, I always meet 2 new LPs every week. I ensure with every quarter, I have a check-in with them and ensure they have our quarterly update. This allows them to follow your progress, learn how you like to invest, and communicate with your LPs. It also really serves to build trust. Doing this not in a fundraising process also removes the power imbalance that is inherent within a fundraise and allows a much more natural relationship to be created. 

Henry Schuck is the Founder and CEO @ ZoomInfo. From ZoomInfo's founding moment, putting $25,000 on a credit card, Henry has led the company to today, with over $1BN in ARR, a market cap of over $10BN, and a team of over 3,600. This is one of the untold but truly great stories in software. In Today's Episode with Henry Schuck We Discuss: 1. From a $5,000 College Fund to Founding a $10BN Company: Why did Henry always believe early in life that he would be successful? Along the way doubt sets in, what did Henry do to combat that doubt when he questioned his own ability and potential? What does Henry believe he is running from? What is he running towards? How did seeing the work ethic of his single mother impact his work ethic with ZoomInfo? 2. Henry Schuck: The Leader: What does Henry believe is the difference between trust vs safety in team culture? Why does Henry believe safety is built through performance? How does Henry manage and communicate underperformance? How long do you give an under-performer? Why does Henry believe that happier teams outperform? What does Henry do deliberately and specifically to drive happiness in the business? ZoomInfo is magnitudes larger than some competitors who receive a lot more attention, how does Henry think about this? How does he manage his own ego as a leader today? 3. Henry Schuck: A Leader in a Changing Market: How does Henry maintain internal morale when employees see their stock options get smashed every day? Does it suck to be a public company CEO in the current market? What element is the worst? How are the buying patterns and behaviors of customers changing in 2023 vs 2021? How does this impact the sales cycle, retention rates, upsell plans, and the structure of the customer success teams? Dec 2023, will we be in a better or worse macroeconomic position? 4. Henry Schuck: Relationship to Money and Fatherhood: How does henry evaluate his relationship with money today? How has it changed over time? Why does Henry very rarely fly private planes? What does he believe this says about his values? How does Henry instill the same desire and worth ethic within his children despite being a billionaire? What does Henry know now that he wishes he could give to his 23-year-old self founding the company? Items Mentioned in Today's Episode: Henry's Favourite Book: The Happiness Advantage: The Seven Principles of Positive Psychology that Fuel Success and Performance at Work

Jason Fried the Co-Founder and CEO at 37signals, makers of Basecamp and HEY. Over an incredible 21-year journey, Jason and his co-founder David have scaled Basecamp to become the communication tool trusted by millions. Jason is also the co-author of the widely acclaimed, ReWork and has also made several angel investments in the likes of Intercom, Gumroad and Hodinkee to name a few. In Todays Episode with Jason Fried We Discuss 1. From Web Design Agency to Founding Basecamp: What was the a-ha moment for Jason when they had to make the pivot from a design agency to going full-time launching and running Basecamp as a SaaS company? What is Jason running towards? What is he running from? What is the single biggest fear that Jason is trying to avoid? 2. Jason Fried: The Leader: Why does Jason believe he is running from his position as leader and CEO @ Basecamp? Why does Jason not like or agree with goals or targets? Why are they not helpful? How does Jason make decisions today as a leader and CEO? What one question does he ask that determines his decision-making process? Why does Jason never compare himself to the competition? Why does he believe competition is for losers? 3. Jason Fried: The Politicisation of Leadership: Why did Jason and David decide to not allow politics in the workplace? How did they manage with 1/3 of their team leaving overnight? How was that experience for them personally? How did it impact the company? Is there anything they would do differently? Does Jason believe we will see the continued politicization of leadership in the coming months? How would Jason advise other CEOs when it comes to taking a stance on politics? 4. Jason Fried: Building the Best Team: What is the one question that determines whether you made a good hire? Why does Basecamp start with hiring all employees on a week-long project contract? Why does Jason believe the best CEOs approach management as the art of the individual? 5. Jason Fried: The Partner, Father, and Husband: Jason and David have been partners for 21 years, why does Jason believe it is helpful that they do not see each other much? Is it right for co-founders and partners to be friends? What have been Jason's single biggest lessons on what it takes to be the best husband? What does great fatherhood mean to Jason? How has it changed over time?

20VC: Fundraising 101 Today we are going to walk through the process of raising a funding round for a hypothetical company. We will break it down by different stages in the fundraising process and at those stages I will talk about how each element differs according to the round being raised.  First, for 99% of fundraises it is a game of shots on goal. You need to have enough investors in the pipeline, it is a sheer numbers game. Miki Kuusi @ Wolt said on 20VC recently for his Series B he got 68 rejections before Laurel Bowden @83North said yes. Wolt sold in 2021 for $7BN to Doordash making a monster return for the company's investors. But 68 meetings before that yes, for the Series B. Also goes to show, you sometimes just need one true believer.  How to Create a Target List of Investors Now we know we need enough shots on goal, we need to bring together a target list of investors, put these investors in three buckets: Priority (5 names of people you really want.) Tier 2 (15 names of people you would like) Tier 3 (15 names of people you would take money from but would not invite to your birthday!)  So how do we choose who goes in what bucket? First, founder references speak volumes and lead to warm intros, so speak to your friends who are founders, ask which of their VCs have been the best, place even more weight on their recommendation if the company has not been a success. It is easy to be a VC champion when the company is flying, you often see the true colours of the VC when a company is really struggling or fails. Get a couple of names there and then analyse the VC landscape, you can do this on Twitter or the VCs website or blog and find the VCs that resonate best with your company. Look at the types of deals they have done before, are they interested in pre-seed fintech in Europe, do they do enterprise SaaS Series A in the Silicon Valley. You can see their portfolio, make sure it is a fit for them. I get about 200 inbounds per day across channel, about 150 are clearly not a fit for me because of stage, sector or location and so making sure the obvious are aligned is crucial. Then double down on their Twitter or public profile to see as much as you can about their values and how they portray themselves. Rule No 1, never work with assholes. Value alignment is really important. Now we have the five priorities and then I would say do the same for the Tier 2 and Tier 3 bucket, make sure they invest both in your stage, sector and geography.  The Biggest Mistakes Founders Make Pitching: So now we have our pipe of investors. A couple of big mistakes I see founders make in this next step.  They go to their priority names first. Do not do this. Your pitch both in delivery, style and messaging will improve so much with each meeting. Start with a couple where you would not be sad if they said no. Analyse in real time in those meetings what messages are hitting and what are not, where are investors spending the majority of the time, are there common questions that keep coming up. If so, create an FAQ page that is in the deck and that will prevent you from having to answer the most obvious in other meetings. With each meeting, you will find ways to iterate the deck, the messaging and the way you present.  Another massive mistake founding teams make, if you are doing a Zoom call and it is a first meeting, do not have more than 2 people on the call from your team. It makes it tough to get to the core of the discussion and removes a lot of the relationship building with too many people too soon. If the investor likes the opportunity, they will ask to meet more team members but do not put too much in front of them to the point it dilutes the message and pitch.  Now we have done the first investor meetings and we have iterated our deck and messaging in accordance with the feedback we got. We now progress to taking meetings with investors we want as our partners.  How to Master the Subtleties of a First VC Call: Every investor call usually starts with each side telling a little about themselves and how they came to be the founder or the VC. As the founder, practice your intro, make it succinct, concise, break it into three chapters, a minute per one is a good guidance. In these you want to show a couple of things, founder <> problem fit or in other words, why you specifically have the right experience or skills to attack this problem. I also like to understand “insight development” as taught to me by the famous OG of seed investing, Mike Maples @ Floodgate. Insight development is the notion that the best companies are founded on a unique insight that the founder has about a product or market that is different to the way the world currently sees it. Include these two in your intro. Keep the intro to no more than 3-4 mins.  For the VCs intro, it is important to try and understand a little more about them. Many VCs give boring and bland intros; “we do Series A and B in Europe and like to lead rounds.” Very standard response and so you should ask them how they like to work with their founders, ask them about a company that struggled and how they worked with the founder to help. Ask them about their decision making process for reserves and pro rata. This creates more of a conversation which will instantly give you as a founder more gravitas in the eyes of the VC.  Use the deck as a vitamin and not a painkiller. I hate pitches where it is read off slide by slide. I would not have the slides showing at all, I will have asked for a deck pre the meeting and I should have gone through it before. The call is for me to ask about questions I want to understand more or double click on. That said, the deck can often be useful as a crutch and so it can work well to have it ready and refer to certain slides as and when necessary.    The 7 Sins of Fundraising Decks: So while we are on the deck, I want to go through a couple of elements that I so often see and they are killer mistakes: Length: Keep the deck less than 10 slides. If you need a couple more to show data or additional research, put it in the appendix at the end of the deck.  Introduction: First slide, company name and then answer the question; if I had a billboard in Times Sq, what would it say on it? 10 words max. From your first slide alone, there should be no doubt about what your company does.  The Team Slide: where do people go wrong here. They put 12 faces on it with their names. No information about the people, where they worked, why they are the best team to solve this problem. A totally useless slide if done like this. So do not do this. Instead, take 4 of those people, break the slide into quadrants and expand on those 4 people’s backgrounds to why they are perfectly suited to do what they are doing. Fewer people more context.  The Useless Advisor Slide: Aligned to the terrible pictures of many team members with no context, the advisor slide, honestly, advisor slides just carry such little weight these days, they are not worth having. Take it out, it is not needed.  Market Sizing Errors: This is a massive one. I see so many make the mistake on market size slide. Say we have a CRM for hairdressers, taking a very random example here, so often I will see a $100BN market, thats the TAM for the hairdressing market or the CRM market, but we are CRM for hairdressers so that is not the right representation and is entirely misleading. It is much better to start with that, then show the slither of wallet spend that hairdressers spend on software and then show the even smaller slither that they spend on CRMs. Use the market sizing slide as a way to show your insight and intellect both into how the market is carved up today but also how it is going to change in the future. There is always the debate of what matters more, large market or amazing founders, the truth is, a massively growing market can cover a lot of operational sins and so showing how the market is and will expand and what causes this, the why now, will always be important. But do not show the massive market for hairdressing or whatever it is, I have seen more $1TN TAM for pet grooming businesses that you can imagine. So do not do that.  Exit Slides are Terrible: I do not see this so often now but do not have an exit slide in the deck for your early stage company, the wrong type of investors will be attracted to you if they like this slide, it encourages short term thinking and is not the right way to present for a company that will reshape an industry so no exit slide.  Why You Should Not Invest: One thing I love in startups and always have when I present my funds is a slide, why you should not invest in me. I think the most important thing for all founders is to be aware of their biggest weaknesses and then have clear action plans on what they are doing to mitigate the chances of them impacting their success. So have a slide that says, hey, these are our 3 biggest weaknesses and then tied to each one, this is what we are doing to solve it. This inspires trust in the relationship with the investor and really shows your self-awareness and strategic thinking. How To Structure The Size and Composition of Your Funding Round: Now at some point in the discussion the size of the round and the price of the round will be asked. Use this as a chance to show your calibre as a founder.  You Cannot Sit With Us (You Get The Joke!!!): Massive mistake founders make is they structure a round that does not allow for a VC to invest. What do I mean by this? VCs that lead rounds need to own at least 8% very minimum and if you come in raising $2M on a $25M cap, that is not enough allocation for the VC and pro-rata amount and then angels as well. Do not prohibit the VC from investing because of the structure of your round. For that example, $5M on $25M would allow for the VC to have 12.5% ownership, a smaller fund to have 3-4% and then a 3-4% allocation for angels.  Is This Check Meaningful?: An important question to ask is: is the check size being invested by the lead a material check size for them and their fund? For example, if the check size they are investing is less than 1% of their fund, it is not that meaningful, if it is less than .5%, it really is not meaningful. Now this could be bad as it means they are unlikely to be able to provide you with the same time and attention they would larger checks. That said, Jason Lemkin has also commented before on the benefits of this as they will leave you alone to execute, they will not put much pressure on you as you are not a core position and it is really yours to execute from there.  Do Not Do a Range: In terms of the actual size of check being raised, I do not like ranges. There is a massive difference between 3 and 5 million, and that impact on your runway is huge and so state a clear and direct number you are raising and what runway that will provide.  Milestone Hitting and Showing Resource Allocation: Use the question of how much are you raising to show your insight into the milestones that you need to hit over the next 18-36 months. Never raise less than 18 months, you also do not need to raise more than 36 months. Plan for a 6 month fundraise and execution 99% of the time always takes longer than you anticipate. With that in mind, I always prefer 24 months as the right period to raise for, this will give you 18 months heads down execution and then 6 months to raise.  Fundraising Rounds are To Prove Hypotheses: If we assume that fundraising rounds are science experiments and you have to prove or disprove a set of hypothesis with this time and money, make sure you can clearly articulate what you need to prove and by when. For the love of god do not say, this is the last round we will ever need to raise before we are immensely profitable, I could have a fund the size of Softbank if I had a dollar for everytime someone said that to me.  How to Answer the Question of Valuation: When you say the size of the raise, say $2M, the basic assumption is that each round will dilute 15-20% and so the average VC will think of a $10M post money valuation straight away when you say a $2M raise. That said, you do not want to anchor yourself to a price, you are running a process as transactional as it sounds and I am not saying you want to optimise for price by any means but the majority of the time, it is best to say, “hey we are raising $2M and we will let the market decide on the price”. This is a great way to answer the question as this will not put anyone off, it will not anchor you to a price and it will also show you are savvy as to the raise process which any incoming investor should want to see as your ability to raise the next round is fundamental for them. Again, use this question to show your sophistication and knowledge as to the finer details of how to navigate a fundraise successfully.    How to Choose Your Lead Investor?   The biggest problem of the last 2 years was people chose their lead having met them once. They will be a partner to you for 10 years and you will not be able to get rid of them, it is literally harder to remove an investor than it is to get divorced. Brian Singerman @ Founders Fund said on the show recently about how he was unable to do his job in COVID as he could not meet founders in person. It is so important to meet your lead investor in person before signing the deal, so much can be gained and learned from those meetings in person. Then there is the question of how do I really get to know someone, especially if it is in a compressed timeline, there are ways that you can accelerate a relationship and getting to know someone, make sure to ask: What would success look like to them with this investment? What are the 1-2 core ways they believe that you will not achieve your outcome? What worries them? Can they give you a reference for founders they have worked with where it has not gone to plan? Also do off sheet references and try to find others where it did not go to plan. You can find their email with the Google Plugin by Clearbit and that is super easy. That should reveal alot.  I also find really being vulnerable, talking about ambitions, inspirations, fears, childhood, my mother has MS and it is a tough and horrible thing to see your mother suffer with, I will discuss that and how it has changed me and my mindset in many ways.  How to Set a Timeline in a Fundraise? In this deliberation phase where you are waiting for a term sheet, you do need to create some form of urgency. Investors often need a reason to move and so it is good to put a timeline on the raise. 14 days is perfect, this is enough time for any VC to do the work they need to do but also if they cannot do it in that time without a plausible excuse, it is unlikely that they would have done the deal and so it will force timewasters to a no sooner and save you time.  Your Term Sheet is Ticking: One thing to be wary of is exploding term sheets. If any VC says you have to sign this here and now, that is BS. Do not do it and that is no way to start a 10 year relationship. That said, it is fair for them to set some form of timeline, otherwise, you can shop the term sheet; share it with everyone and use the first people to commit as leverage to create FOMO to get other people to commit. This can be a disadvantage of being a first mover as a VC but that is why they will often have some form of expiry date and that is not unreasonable.    When You Have Multiple Term Sheets: KISS (KEEP IT SIMPLE STUPID)   Then you have leverage and you can optimise the round on price, size of round, size of lead check to angel allocation etc etc. My advice here would always be do not over optimise. If the chosen partner is slightly lower, take it. Do not lose the right partner because of a small 5% difference in price or size of round. Another big mistake founders make when they have multiple term sheets is communication. It is fine if you need another couple of days to consider the decision but keep everyone updated. Let each investor who is waiting know, you are still thinking it through and will be back to them shortly. Name when you will have an answer, a communicated delay is fine, no communication is not. Then another massive mistake founders make is for the VCs they choose not to go with, they do not turn them down graciously. These investors could likely fund your next round, a bridge round and you never know when you might need them and so always turn them down super well and keep them on side, they could be helpful in the future. If a VC Does These 3 Things: Forest Gump It:  Now the massive red flags with leads in this process that we need to call out: Pay to Pitch: If any VC ever makes you pay to pitch them. This is unacceptable and we have to remove this from the industry. Tweet me the details of these investors, it can be anonymous but these bad actors need to be called out. Investment Tranches Kill Companies: If it is an early round and they want to do the investment in tranches. No. This is such an inhibitor for the business it will not allow you to allocate resources effectively or with confidence. Do not allow for tranches. A bad deal can sometimes be worse than no deal. Tranches does not set you up to execute against a plan, build a world class team and achieve what you can. Say no.  Early Signs of Excess Control and Ego: If they haggle immensely on salary over small amounts, if they suggest you should be on $60K not $62K and they make a big deal out of it. This is a sign of what they will be like to come. Do not accept it.  So now we have our lead VC locked in and we have to allocate the rest of the round. I would work hand in hand with my VC to construct the rest of the round. They will have angels they work closely with and think highly of. Use them to help map out those people and then make those intros for you.  How to Allocate Your Angel Allocation: Assemble your angel cap table as you would a sports team. Each person has a specific position which they are specialised to and have a world class skill in. Someone for marketing, hiring, regulation, PR, partnerships etc. A massive mistake I see so often is founders try to cram down all their angels to their smallest allocation so they can fit as many as possible. Do not do this. Give fewer people more allocation. The only thing that matters is that the check size matters to them. For some it will be $10K for others it could be $50K but fewer with more skin in the game is important.  Next I see so many founders drag out the process meeting just one more investor and just one more, after a certain time, just get it done, get it closed and move on.  Just Closed: Time to Prep for the Next Round So now we have closed the round, congrats. Now time to start prepping for the next round, one thing to remember, as a founder, you are always raising. So here is what we should do next: Sit down with our new lead investor and align on what we believe we need to hit to unlock the next round of funding. Will that next round come from them or external financing?  If external financing, what 5 names should we focus on? Make sure to send those 5 names monthly updates with your progress. Investors invest in lines not dots.  Make sure to meet them on a quarterly basis.  By the time of your next fundraise, following 6 face to face meetings and 18 updates, the investor and you will know if this is a partnership you want to pursue.  I want your feedback. Did you enjoy this post? Let me know on Twitter here. 

Barry McCarthy is Peloton’s CEO and President. McCarthy is a seasoned executive who served as CFO of Spotify from 2015 to January 2020, and CFO of Netflix from 1999 to 2010. Prior to Netflix, McCarthy held various leadership positions in management consulting, investment banking, and media and entertainment. McCarthy has served on the boards of directors of Spotify and Instacart since January 2020 and January 2021, respectively. In addition, McCarthy has served as a member of the boards of Chegg, Eventbrite, MSD Acquisition Corp, Pandora, and Rent the Runway.  In Today's Episode with Barry McCarthy We Discuss: 1. From Netflix to Spotify to Leading Peloton: How did Barry make his way into the world of startups and come to work with Reed Hastings at Netflix? What are his single biggest takeaways from working with Reid? Why did Barry decide to move to cold Stockholm to work with Daniel Ek and Spotify? What makes Daniel the special leader that he is? Was Barry nervous about assuming the role of CEO @ Peloton? Are the elements he was most worried about the elements that are his biggest challenges today? 2. Barry McCarthy: The Leader What does "high performance" in business mean to Barry? Daniel Ek has described Barry as the "most strategic dealmaker in the world". What does Barry believe makes him so good at dealmaking? Where do so many go wrong? Barry pioneered the model of the direct listing, why does he believe they are better? Why was it right as an approach for Spotify? Will we continue to see more? What is Barry's framework for making tough decisions? How has it changed over time? 3. Barry McCarthy: The Master of Boards: Barry has sat on some of the best boards from Netflix to Spotify to now Peloton and Instacart, what does Barry believe makes the best boards? Where do many boards go wrong? Where do they become dysfunctional? What can and should be done to stop that? How does Barry advise other board members on the right way to deliver tough news constructively? What is the single biggest advice Barry would give to young board members assuming their first boards? Where do many young board members go wrong? 4. Barry McCarthy: Mastering the Mechanics: Daniel Ek suggested that I had to ask about “demand creation theory and your ideas about whether the market is efficient”. What did he mean by this? How does Barry think about it? How does Barry think about the interplay between gross margin, experience and retention? Why did Barry decide it was the right decision to evolve the strategy from owning distribution to working with Amazon etc?

Hadi Partovi is a tech entrepreneur and investor, and CEO of the education nonprofit Code.org. Before founding Code.org, Hadi founded two prior startups: Tellme Networks (acquired by Microsoft, discussed on 20VC with Emil Michael), and iLike (acquired by Newscorp). Hadi has also been an active advisor and angel investor to some of the best including Facebook, Dropbox, airbnb, and Uber. If that was not enough, Hadi currently serves on the Board of Directors of Axon and MNTN. In Today's Episode with Hadi Partovi: 1.) From the Iran-Iraq War to Founding Startups: How Hadi and his family made their way from war-torn Tehran to the US and Silicon Valley? How did seeing his family have nothing and struggle financially impact Hadi's mindset as an entrepreneur? What does Hadi believe he is running from? What is he running toward? 2.) Lessons from Ballmer and Zuckerberg: How did Hadi first come to meet a young Mark Zuckerberg when TheFacebook had less than 10 employees? Why did Hadi believe he was so special from that first meeting? What are Hadi's biggest takeaways from working with Steve Ballmer? How did the reign and leadership of Ballmer compare to the reign of Bill Gates? Hadi has helped both Facebook and Dropbox with their engineering hires, what is the secret to hiring amazing engineers? How does he structure the process? Where do so many go wrong? 3.) Hadi Partovi: The Leader: How does Hadi define "high performance" in leadership? How has it changed with time? What is Hadi's framework for making tough decisions? How does Hadi teach that framework to his team? What are the biggest mistakes leaders make in decision-making? How important does Hadi believe speed of execution is? How does Hadi determine when is the right time to go slow to go fast? 4.) Hadi Partovi: The Person: How does Hadi analyze his relationship with money today? How does it change over time? Hadi stepped off the for-profit treadmill with Code.org, why did he make that decision? How does he avoid the trappings of chasing wealth? How does Hadi think about ego and ego management today? How does Hadi separate self-worth from financial gain and accomplishment? Items Mentioned in Today's Episode: Hadi's Favourite Book: Sapiens: The #1 bestselling journey through human history and anthropology

Maggie Hott is the Director of Sales @ Webflow where she leads their Sales Dev, Account Executive, and Solution Engineering orgs. Prior to Webflow, Maggie spent an incredible 6 years at Slack in a period of hypergrowth for the company having joined as the founding AE scaling to a Sr Enterprise Leader. Before Slack, Maggie was the founding Sales hire at Eventbrite. If that was not enough, Maggie is also an active angel investor, an advisor to Cowboy Ventures, Scribble Ventures, and is a Founding Operator and LP @ Coalition Partners. In Today's Episode with Maggie Hott We Discuss: 1. The Cold Email that Led to a World-Class Sales Career: How a cold email to Kevin Hartz @ Eventbrite led to Maggie's career in sales? What are the 1-2 biggest takeaways from her time at Slack? How did they impact her mindset? What does Maggie know now that she wishes she had known when she entered sales? 2. The Sales Playbook: PLG and Enterprise: How does Maggie define the sales playbook? What is it? What is it not? Is it possible for early-stage companies to do both enterprise and PLG at the same time? When is the right time to add enterprise to a PLG motion? What are the steps to build an outbound sales engine in enterprise? Where do many go wrong? 3. Building the Bench: Hiring Your First Sales Team: Should founders look to hire a Senior Head of Sales first or a more junior sales rep? Should they be hired one at a time? What are the benefits of hiring many at the same time? What is the right process to hire your first sales hire? What are the core traits and habits that make the first 10x sales hire? What are the right questions to ask to unveil those characteristics? 4. Making the Machine Work: The Process: What can sales leaders do to proactively build relationships with other parts of the org? How can more junior sales reps build relationships with other functions? Why does Maggie believe that mis-hiring can be a $1M mistake? What are the early signs that a new hire is not working out in sales? How does this differ for outbound? Why is it dangerous to make your self-serve product too good?

Ben Chestnut is the Co-Founder of Mailchimp, the all-in-one marketing platform for small businesses. Last year, in Sept 2021 it was announced that Intuit would acquire Mailchimp for a reported $12BN. There are so many things to love about the Mailchimp journey to this point. First, Mailchimp was founded as the result of a side project of a design agency Ben and his co-founder, Dan, used to run. Second, Mailchimp is and has always been based in Atalanta, eschewing the notion you have to be in SF or NYC to build a massive business. Then third, they never raised venture funding for the business all the way until their $12BN acquisition. Ben led Mailchimp to over 1,200 employees and millions of global users. In Today's Episode with Ben Chestnut We Discuss: 1. From Mama's Kitchen to the Smell of Business and Founding Mailchimp: How did Ben turn a mediocre agency into the founding of Mailchimp? What was the a-ha moment? At what stage of the business did Ben quit the agency and go all in on Mailchimp? What sign did he need that Mailchimp had true product-market fit? When Ben's mother died, he bought every flower in the local town to commemorate her. How did Ben's mother impact the type of father and husband he is today? How did she impact the way that he led Mailchimp as CEO? Ben's fishing trips with his father played a big role in his early years, what were the single biggest lessons for Ben from his fishing trips with his father? 2. Ben Chestnut: The Leader: How does Ben define the term "high performance" in leadership? What does Ben mean when he says "the secret to happiness is to stay in your lane"? Why would Ben describe himself as the "leader of the misfits"? How did that early experience and labeling impact both the people he hired and the culture he created at Mailchimp? What does Ben mean when he says he used to have a "hands off, eyes off" leadership style? What have been the single biggest drivers in his development as a leader? 3. Ben Chestnut: The Person: Relationship to Money: How does Ben reflect on his relationship to money? How has it changed over time? Why does Ben still to this day buy lottery tickets with his wife? Conquering Fatherhood: What does being a great father to Ben mean? How does Ben attempt to instil the same work ethic and drive when his children are born into immense wealth? The secret to Marriage: What does Ben believe is the core to a successful and thriving marriage? How does Ben view his role in the marriage? How has it changed over time? Potential Lost Identity: A founder's identity is so closely tied to their company, how did Ben manage the challenge of selling his company but retaining his identity? What did Ben learn about himself through many different acquisition processes? 4. Mailchimp: The Business: Why did Ben never raise venture money in the 21 year journey of Mailchimp? Why did Ben never accept any of the acquisition offers that came before Intuit? How did Ben motivate his team after they knew each acquisition offer was being turned down? Why did Ben decide the acquisition by Intuit was the right decision for the company? How does Ben view his role in the company now and moving forward?

Bob Pittman is Chairman and CEO of iHeartMedia, Inc., the number one audio company in America. Prior to iHeart, Bob has just had the most amazing career as a co-founder and programmer who led the team that created MTV. He has also led some of the most incredible turnarounds as CEO of MTV Networks, AOL Networks and Time Warner Enterprises and as COO of America Online, Inc. and later AOL Time Warner. In Today's Episode with Bob Pittman We Discuss: 1. From Flying Lessons to Radio: How Bob first made his way into radio at the age of 15? What does Bob know now that he wishes he had known when he started his career? What is the most painful lesson Bob has learned in his career that he is pleased to have learned? 2. Decision-Making in Leadership: How does Bob structure all decision-making as CEO today? Why does Bob ensure that all decisions are made within 24 hours? What are the pros and cons? How does Bob prevent consensus decision-making? How does Bob create dissent in a discussion? How do the best leaders know when to kill a project? What do most do instead? 3. Tactics vs Strategies: Why Plans Are BS! What is the difference between a tactic and a strategy? When is the right time to change your strategy and tactics? What have been Bob's biggest lessons on how to get teams on board with tactical changes? Why does Bob believe that plans are BS? When can they be useful? 4. The Secret to Messaging and Storytelling: What does Bob believe is the universal truth to successful consumer messaging? What has changed and what has not changed in the way companies tell stories to their customers? Is there a difference between a great product and a great company? What are examples? What excites Bob most about consumer habits today? 5. Bob Pittman: AMA: What does Bob believe is the success to successful parenting? How has it changed? How does Bob analyze his own relationship to money today? How has that changed? Why does Bob not believe in legacy? What do people get most wrong when it comes to ego?

Marty Cagan is one of the OGs of Product and Product Management as the Founder of Silicon Valley Product Group. Before founding SVPG, Marty served as an executive responsible for defining and building products for some of the most successful companies in the world, including Hewlett-Packard, Netscape Communications, and eBay. He worked directly alongside Marc Andreesen and Ben Horowitz at Netscape and Pierre Omidyar at eBay. In Today's Episode with Marty Cagan We Discuss: 1. Entry into the World of Product From Engineering: How Marty first made his way into the world of product, having started life as an engineer? What does Marty know now that he wishes he had known when he started in product? What are Marty's biggest tips to anyone making the move from engineering to product? 2. Lessons from Marc and Ben at Netscape and Pierre @ eBay: What are the single biggest lessons Marty took from working side by side on product with Ben Horowitz and Marc Andreesen? What did Netscape do right? What did they do wrong? With hindsight, what would Marty have done differently? How did Marty break all of his rules by working with Pierre Omidyar? 3. Hiring a World Class Early Product Team: When is the right time to make your first product hire as a startup? What is the right profile for that first product hire? Senior or junior? If you go for the junior hire, how do you structure the rest of the team? If you go for the Senior hire, how do you structure the rest of the team? What are the single biggest mistakes startups make when hiring their first in product? Does Marty prefer someone with or without expertise in the domain you are in? 4. Mastering the Onboarding Process: What is the optimal onboarding process for all new product hires? How can leaders ensure that product hires see and understand all areas of the business? What can product leaders do to proactively impress in the first 30-60 days? What are clear red flags that a new product hire is not working out? How long do we give them?

Martin Casado is a General Partner @ a16z where he focuses on enterprise investing. At a16z, Martin has led investments and serves on the board of dbt Labs, Fivetran, Material Security, Ambient AI and many more incredible companies. Before venture, Martin was previously the Co-Founder and CTO at Nicira, acquired by VMware for $1.26 billion in 2012. While at VMware, Martin served as Senior VP and General Manager of the Networking and Security Business Unit, which he scaled to a $600 million revenue run-rate business. In Today's Episode with Martin Casado We Discuss: 1. From $1.26BN Founder to Leading Enterprise Investing for a16z: How did Martin make his way into the world of VC and come to lead enterprise investing for a16z? What does Martin know now that he wishes he had known when he started investing? What have been some of his biggest investing lessons from Marc and Ben? 2. The VC Model is Broken and Why: Why does Martin believe that the current model for venture is broken? Why does Martin believe that VCs are not oracles and they were not gifted with picking ability? How will asset allocation more broadly fundamentally change over the next decade? Why will Silicon Valley take over and run Wall St? Why does Wall St not care about innovation and true technological development? Who will be the winners and who will be the losers in the next 10 years of venture? 3. Surviving a Crash - What Founders Need To Know: Layoffs: What is Martin's advice to founders on doing layoffs today? How much is the right amount to cut? Should it be done in one go? How should this be communicated to investors and the board? Scenario Planning: What three scenario plans should all founders be creating right now? How should they know which one is the right one to execute against? Comparisons: How should founders use and look to public company performance and market cap to determine which plan they should choose? Hiring Freeze: Why does Martin believe the biggest companies in the world make massive mistakes by freezing hiring? What should they do instead? 4. The Changing Guard at a16z: What have been the single best and worst changes a16z have made over the last 24 months? What are the first things to break when a firm scales as fast as a16z has done? Does Martin agree a16z returns will reduce with the scaling of their funds larger than ever? How does Martin look to train and educate his junior team? How does he advise them on surviving a downturn? What should they do? What should they not do? 5.) The Makings of a Great Board: What are the three types of board members? What is the best? What is the worst? What does Martin believe makes the truly great boards? What is the biggest advice Martin gives to young board members today? How has Martin changed as a board member over time? What does he need to improve? Items Mentioned in Today's Episode: Martin's Fave Book: The Weirdest People in the World: How the West Became Psychologically Peculiar and Particularly Prosperous

Will Hockey is the Co-Founder and Co-CEO @ Column, the only nationally chartered bank built to enable developers and builders to create new financial products. Before co-founding Column, Will was the Co-Founder, President, and CTO @ Plaid, a world-leading data network and payments platform. In 2020, Visa attempted to acquire Plaid for $5.3BN, however, this was blocked due to regulatory issues and the company went on to raise at a reported $13.4BN valuation just 9 months later. Additionally, Will is on the board of Scale.ai. In Today's Episode with Will Hockey We Discuss: 1.) The Founding of $13.4BN Plaid: How did Will make his way into the world of startups and come to found Plaid with Zach? If we are all a function of our histories, what is Will running from? What is he running toward? What does Will know now that he wishes he had known when he started Plaid? 2.) Will Hockey: The Makings of a Decacorn Founder: What does the term "high performance" mean to Will? How has this changed over time? Having had such a successful time building Plaid to $13.4BN, how does Will assess his own relationship to risk and his relationship to money? How does Will approach his own personal portfolio planning? Equity, debt, real-estate? How does Will optimize his own personal wealth? Column is his second time founding a company, what did Will decide to take from Plaid that worked well? What did he decide he would not do having seen it work badly at Plaid? 3.) The Building of Truly Great Teams: Why does Will believe that companies can be built so much slower than people think? How does Will determine the decisions that have to be made fast vs those with time? How does Will ensure the same size of urgency and speed within his team without this time or funding pressure? What have been Will's single biggest lessons when it comes to people acquisition and retention? 4.) Fintech: The Next 10 Years: How will the next 10 years look different from the last in fintech? What changes will be better? What will be worse? What is Will worried about? What is he excited about? What does Will mean when he says, "the US financial system can function like a protocol"? What does Will believe are some of the core myths of the US financial system? Why does Will believe the current financial system can and will fix a lot of what crypto is trying to solve? What barriers will prevent this from happening? Items Mentioned in Today's Episode: Will's Favourite Book: The World for Sale: Money, Power and the Traders Who Barter the Earth’s Resources, Merchants of Grain: The Power and Profits of the Five Giant Companies at the Center of the World's Food Supply

Jason Lemkin is one of the OGs of SaaS of the last decade. As the Founder of SaaStr, he has inspired more SaaS founders than one can imagine building "The World’s Largest Community for Business Software." Jason also invests out of the $100M SaaStr Fund and in the past Jason has led rounds into TalkDesk, Pipedrive, Algolia, Gorgias, Salesloft, and many more incredible companies. Prior to founding SaaStr, Jason was the Co-Founder of Echosign, an early e-signature business, funded by Emergence Capital and that was acquired by Adobe for $100M. In Today's Episode with Jason Lemkin On Algolia We Discuss: 1.) Meeting the Unicorn: Algolia: How did Jason first come to meet Nicolas (Founder) and Algolia? What specific elements of cold emails make the best attract Jason's attention? What do they have in them? What are the most common mistakes people make with cold emails? What is the single biggest mistake Jason made when making the deal with Algolia? How did Jason lead their seed round when their round was "oversubscribed"? 2.) Competition and TAM: The Reasons To Say No: Competing with Free: How did Jason analyze the competitive landscape Algolia was facing? How did he gain comfort that they could compete and win against free and open-source? TAM Analysis: The TAM at the time for Algolia was $2M. How did Jason analyze the TAM at the time? How did he get comfortable with such a small TAM? What are the single biggest mistakes investors make when analyzing competition today? What are the biggest mistakes founders make when presenting the competitive landscape? What are the single biggest mistakes investors make when analyzing TAM today? What are the biggest mistakes founders make when presenting the TAM and how it breaks down? 3.) Investing Lessons Transition from CEO to VC: Jason has previously said one of his biggest lessons is "bet on what you know when you go from CEO to VC"? What did he mean by this? How can one keep this operator knowledge and mentality when one is a VC for a long time? What are the biggest pieces of advice that Jason would give to operators becoming investors? What are the biggest mistakes that Jason made in his first 3 investments as a VC? How did he change? 4.) Mastering the World of Venture Today: Why does Jason believe that he has become a worse investor with the rise of "remote investing"? Why does Jason believe he is a worse investor without having a partner in SaaStr Fund? Why does Jason believe that even the best founders do not want hard feedback anymore? Should we as VCs still give it to them? What has Jason learned here? Will we see great LP churn and many LPs leaving the asset class? What will happen to the existing incumbents with massive AUM and reduced performance?

Miki Kuusi is the CEO of Wolt and Head of DoorDash International. In 2014 Miki founded Wolt with a mission to turn the smartphone into a remote controller for life, starting with delivering your favorite restaurant food, to you at home. Today Wolt operates in 23 countries, across several different categories, has over 4,000 employees, and last year, Doordash made the move to join forces with Wolt in a deal worth a reported $8.1BN. Previously, Miki was the CEO of Slush, one of the leading tech and investor events in the world attended by more than 25,000 people annually. In Today's Discussion with Miki Kuusi: 1.) Founding Slush and Wolt: An Entry into Startups: How did Miki come to found Wolt? What was that a-ha moment? Did Wolt have product-market-fit from Day 1? What was the turning point when they did? What does Miki know now that he wishes he had known when he started Wolt on Day 1? 2.) The Makings of a Truly Great Leader: How does Miki define "high performance" today in leadership? How does Miki think about what focus means in leadership? What is the hardest decision Miki has had to make when it comes to focusing the company? What did he learn from Ilkka @ Supercell? What does Miki believe is the KPI of success as the CEO? How does it change? What does Miki believe is the difference between good vs great leadership? What does Miki believe is the biggest sacrifice he has made as the CEO? 3.) Hiring a Team to Compete on a Global Stage: How does Miki use compensation to create a culture of ownership and accountability? Does Miki start from a position of trust and it is there to be lost or no trust and it is there to be gained? What is the difference between a team and a family in company building? What is the core difference between trust and safety in company building? Why does Miki always want to have trust but not want to have safety? What are the single biggest hiring mistakes that Miki has made? How has he learned from them? Why does Miki believe you do not want to hire people that have done it before but hire the people who have seen those people do it before? Why does Miki believe most companies are merely glorified recruiting operations? Does Miki believe that companies need to be as big as they have grown into, headcount-wise? 4.) Miki Kuusi: The Personal Journey What single day was the hardest day of the Wolt journey for Miki? How did it change him? Why does Miki believe that for their Series B, all-bar one VC turned them down? How does Miki assess his own relationship to risk and money today? Why is Miki an advocate for founders taking secondaries along the journey? What can Europe do to become a powerhouse in tech moving forward? Why did Miki decide to sell the company to Doordash? What is he most excited to learn from Tony Xu, Doordash Founder and CEO? Items Mentioned in Today's Episode: Miki's Favourite Book: The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers

Casey Winters is the Chief Product Officer at Eventbrite. Prior to Eventbrite, Casey led the growth product team at Pinterest. Before Pinterest, Casey started the marketing team at Grubhub and scaled Grubhub’s demand-side acquisition and retention strategies.  Elena Verna is the Interim Head of Growth at Amplitude. Former exec @ Miro, Netlify, SurveyMonkey. Growth Advisor to companies including Krisp, MongoDB, Ledgy, Builder.io and SimilarWeb. Kieran Flanagan is SVP Marketing at HubSpot, where he has helped the business grow internationally, move to a product-led business, quadrupled its marketing demand, and built out its media team, including the acquisition of ‘The Hustle.’ Andy Johns career started in growth at Facebook when the company scaled from 100M-500M active users. Since he has worked in some of the leading growth orgs at companies like Twitter, Quora and more recently at Wealthfront as Head of Growth and President. Bangaly Kaba is the Director of Product Management @ Youtube. Prior to Youtube, Bangaly led the product growth and consumer product orgs at Instacart and before Instacart was Head of Growth @ Instagram, helping grow Instagram from 440M to > 1B monthly actives in 2.5yrs. Ed Baker is a growth advisor to various startups including Lime, Zwift, Whoop, Crimson Education, GoPeer, and Playbook. Ed was the VP of Product and Growth at Uber from 2013-2017. Prior to Uber, Ed was the Head of International Growth at Facebook. Adam Fishman was the Chief Product and Growth Offer @ Imperfect Foods. Before Imperfect, Adam was VP of Product and Growth @ Patreon, Before Patreon, Adam was the Head of Growth @ Lyft, Adam was the first growth and marketing employee hired and grew the team to 18 people. In Today's Discussion on When To Hire a Head of Growth: 1.) When is the right time to hear your first growth hire? 2.) Is this hire a senior growth leader or a more junior growth engineer? 3.) What can early-stage startups do to entice senior growth leaders to their early-stage company? 4.) What data infrastructure should be in place prior to hiring your first growth hire? 5.) What does the optimal onboarding process look like for all growth hires? 6.) What can founders and CEOs do to set their growth hires up for success?

Jeffrey Katzenberg is an entertainment industry executive and entrepreneur, who throughout his career has repeatedly reshaped the media landscape. Jeffrey co-founded DreamWorks SKG, serving as CEO of DreamWorks Animation, which he grew into the world’s largest animation studio, known for Shrek, Kung Fu Panda, Madagascar and more. In 2016, DreamWorks Animation was sold to Comcast for $3.8 billion. Before founding DreamWorks, Jeffrey was Chairman of The Walt Disney Studios, where he took the studio from last place to first at the box office with hits like Three Men and a Baby, Pretty Woman, Father of the Bride and Sister Act. Most recently, Jeffrey co-founded WndrCo alongside Sujay Jaswa and has led WndrCo’s investments in Airtable, Frame.io, Quibi, Vise, Placer.ai, NexHealth, Deel, and ID.me. Sujay Jaswa is one of Silicon Valley’s leading business innovators. At Dropbox, he created and led the company’s global business and finance organizations. Sujay and his teams raised over $1 billion, launched and scaled Dropbox’s products for businesses, created partnerships responsible for over 100 million users, executed some 20 acquisitions, and scaled the global business team from two to more than 500 employees in seven global offices. During this period, the company significantly scaled overall revenue from $12 million in 2010 to over $500 million run rate, Dropbox for Business revenue from $1 million to over $200mm run rate, and users from 15 million to 300 million. Most recently, Sujay Jaswa and Jeffrey Katzenberg co-founded WndrCo and Sujay has led WndrCo’s investments in Figma, 1Password, Databricks, Pango, Pilot, Rally, Zagat / The Infatuation, and other great companies. In Today's Episode with Jeffrey Katzenberg and Sujay Jaswa: 1.) From Dreamworks and Dropbox to Venture with WndrCo: How did Jeffrey and Sujay both make their way into the world of venture from Dropbox and Dreamworks? What was Jeffrey's single biggest lesson from his time leading Dreamworks and being in Hollywood? What was Sujay's biggest takeaway from being at the helm as COO at Dropbox? 2.) Operating Experience is Irrelevant and Can Be Dangerous: Why does Sujay believe that operating experience is irrelevant? What are the single biggest mistakes that operator investors make when it comes to advising their founders? What do both Sujay and Jeffrey do to try and refresh their operating experience in real time? How did Quibi impact their willingness and desire to take large risk both investing and operating? 3.) Building Teams and Hiring People: What are the single biggest hiring mistakes Jeffrey and Sujay have made? What did Jeffrey mean when he said at Disney, “if you do not come in on Saturday, do not bother coming in on Sunday”. How do Jeffrey and Sujay feel about remote work? Why did it not work for them? What did Alfred Lin @ Sequoia teach Sujay about the question all managers need to ask themselves on questing whether they should let someone go? 4.) Silicon Valley: Dead and Entitled? Why does Jeffrey strongly disagree with the death of Silicon Valley? What will happen to the generation of companies that raised too much with no product-market fit? How will the mass layoffs in the valley change the valley as it is today? Does Sujay agree that millennials are the worst segment to hire from? Are they entitled?  

Semil Shah is the Founder of Haystack, one of the leading pre-seed and seed firms of the last decade. Among Semil's portfolio include the likes of DoorDash ($DASH), Instacart, Hashicorp ($HCP), Opendoor ($OPEN), Figma (acquired by Adobe), Carta and many more exceptional companies. Semil's first fund is marked between a 30 and 40x fund, astonishing. In Today's Episode with Semil Shah We Discuss: 1.) The Makings of Semil Shah: What is Semil running away from? What is he running towards? What does Semil know now that he wishes he had known when entering venture? What is Semil's biggest advice to managers raising their first funds now? 2.) Fund Sizing: Growing vs Staying Disciplined: Question from Hunter Walk: How does Semil determine the right size fund to raise with each fund Question from Satya Patel: Why have you resisted increasing AUM? In the last episode Semil mentioned a three-year deployment cycle for the fund, did he stick to it? What are the benefits and drawbacks? What investing mistakes did Semil make over the last 3 years that he wishes he had not made?   3.) The Secret to Fundraising for a Fund: What is Semil's biggest advice to emerging managers on finding new LPs? What works? What materials do managers need to have in place for a new fundraise? Deck? Dataroom? What are the most common mistakes VCs make when pitching LPs their funds? How does Semil follow-up with potential LPs post-call? What works? What does not? How does Semil suggest creating a sense of urgency for LPs to commit to a fund? How does Semil feel about giving preferential terms to convince LPs to commit to the first close? 4.) The Current Landscape: For VCs: How will the current landscape impact emerging managers' ability to raise? What advice would Semil give to them? Raise smaller? Kyle Harrison said on the show recently, “differentiation will kill 80% of venture firms, especially the so-so ones”. Does Semil agree? Who is set to struggle? Who is set to thrive in this environment? For LPs: What does Semil think are the biggest mistakes LPs made over the last 2-3 years? How will they respond in this market cycle? If Semil were handed an endowment fund, how would he allocate today? Does Semil agree, we will see a denigration of venture returns to those of PE like multiples? Why? For Founders: How does Semil advise founders on raising today when everyone says they are investing but very few really are? How does Semil advise founders on how to think about valuation inflection points with respect to raising capital? Items Mentioned in Today's Episode: Semil's Favourite Article: Master of Play Semil's Most Recent Investment: Impart Security

Oana Olteanu is a Partner @ SignalFire where she focuses on enterprise software at Seed, Series A and Series B. Prior to joining SignalFire, Oana was at Scale Venture Partners where she invested in applied ML and developer tooling. Oana sourced Scale’s investments in Observe.ai, Flatfile, and Proscia. She was part of the deal teams for Honeycomb and AllyO (acquired by HireVue). She also supported existing portfolio companies such as Dialpad, Matillion, and BigID. Prior to Scale, Oana was an AI seed investor at SAP.io, SAP’s $35M seed fund, where she sourced the investments in Plum.io, Oto.ai, and Akorda. In Today's Episode with Oana Olteanu We Discuss: 1.) From Tank Driving in Romania to VC's Rising Star: How Oana made her way from driving tanks in Romania to becoming a VC? How did leaving Romania for Germany and then moving to the West Coast impact her mindset? What does Oana know now that she wishes she had known when she entered VC? 2.) How to Assess a VC: The Founders Guide: Pre-investment, how can founders know whether a VC can add value? What are the signs? What three core questions will reveal how much value a VC can add? Post-investment, what can founders do to extract the most value from their VCs? What should the founders ask their investors for help with? What should they do themselves? 3.) The VC <> Founder Relationship: Oana has the highest founder NPS of any VC I have ever had on 20VC, what does Oana believe makes her founders rate her contribution so highly? What works? What does not? How does Oana give sometimes very hard feedback to founders but retain that relationship of trust and safety at the same time? What mistakes do other VCs make in giving feedback? What does Oana believe are the single biggest misalignment between VCs and founders? 4.) VCs Behaving Badly: 101 What are the single biggest ways Oana sees VCs behaving badly? How does Oana think founders expectations of the product of venture should change? Does Oana believe boards are valuable? What can be done to improve them? Items Mentioned in Today's Episode: Oana's Favourite Book: The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living: Featuring new translations of Seneca, Epictetus, and Marcus Aurelius

Oliver Jay (OJ) is one of the most successful sales leaders of the last decade. Most recently, OJ spent 6 years as CRO @ Asana and grew the team from 20 to over 450, becoming a master in sales onboarding in the process. Before Asana, OJ spent 4 years at Dropbox, where OJ was Head of APAC & LATAM. Jordan Van Horn is a Revenue Leader @ Monte Carlo. Prior to this role, Jordan spent 4 years at Segment as VP of Sales, leading a sales team of 50+ Account Executives. Before Segment, Jordan was at Dropbox for 4 years leading enterprise sales for Dropbox Business. Dannie Herzberg is a Partner @ Sequoia Capital and before Sequoia, Dannie spent 4 years at Slack as their Head of Enterprise Sales, growing the business from $100M – $1B in revenue. Before Slack, Dannie spent over 5 years at Hubspot building sales teams. Zhenya Loginov is the CRO @ Miro. At Miro, Zhenya runs the go-to-market team of 700+ people across. Prior to Miro, Zhenya was the COO @ Segment where he built and ran the global go-to-market team of 200+ people. Pre-Segment, Zhenya led a 100-person team at Dropbox across different functional areas. Lauren Schwartz is VP of Enterprise Sales at Fivetran, where she has scaled the team to nearly 100, while more than tripling enterprise revenues. Previously, Lauren spent close to 4 years at Segment where she started as the first female AE and ultimately built and led sales teams in enterprise and growth. Kyle Parrish is VP Sales @ Figma, where he built the sales engine from scratch to today, with over 100 in sales. Before Figma, Kyle spent over 5 years at Dropbox in numerous different roles including Head of Sales, and Global Partnerships lead, responsible for growing Dropbox’s partner ecosystem. In Todays Episode on Sales Onboarding We Discuss: 1.) How should the onboarding process for all new sales reps be structured? 2.) How should the onboarding process for a new sales leader be structured? 3.) What specific things can leaders do to set both reps and leaders best up for success? 4.) What are the single biggest red flags in the first 30 days that a rep is not going to work out? 5.) What tools and software can be used to improve this process of ramping new reps?

Cathie Wood is the CEO & CIO @ ARK Invest, focusing solely on disruptive innovation, primarily in the public equity markets. ARK has become renowned for opening up its research and becoming a ‘sharing economy’ company in the asset management space. Prior to ARK, Cathie spent twelve years at AllianceBernstein as CIO of Global Thematic Strategies where she managed over $5 billion. Cathie joined Alliance Capital from Tupelo Capital Management, a hedge fund she co-founded, which managed $800 million in global thematic strategies. Prior to Tupelo Capital, she worked for 18 years with Jennison Associates LLC as Chief Economist, Portfolio Manager and Director.  In Today's Episode with Cathie Wood We Discuss: 1.) Entry into Hedge Funds at 20: How did Cathie get her first role in the world of finance at the tender age of 20? What is Cathie running from? What is Cathie running towards? What are some of Cathie's biggest lessons from seeing the dot com bust at Tupelo? What does Cathie know now that she wishes she had known when she started investing? 2.) Why Benchmarks and Passive Investing are Bad: Why does Cathie believe that benchmarks and indexes have become dangerous for consumers? Why does Cathie not believe what everyone else does regarding inflation? How much of the performance of large-cap tech stocks is tied to the growth of passive investing? Why does Cathie think the Fed is making a huge mistake? 3.) Time to Pick Companies: Why does Cathie believe that Facebook is emerging as an attractive value stock? How does Cathie believe Elon Musk and Jack Dorsey could build the largest universal wallet? If Cathie were to put all her money into one of their companies, what would it be? Why does Cathie believe Zoom is one of the most misunderstood companies? 4.) Why Venture: Why Now: Why did Cathie decide to do a venture fund with ARK now? Why did Cathie decide to do a no-carry structure with a higher management fee? How does that align incentives with investors? In venture, the asset chooses the capital, how does Cathie analyze why the best founders in the world will pick and work with ARK over other amazing VCs? What is the single biggest risk you are underwriting when investing in ARK's venture fund? Items Mentioned in Today's Episode: Cathie's Favourite Book: The Emperor of All Maladies: A Biography of Cancer

Martín Escobari is Co-President, Managing Director and Head of General Atlantic’s business in Latin America. Martín is Chairman of the firm’s Investment Committee and also serves on the Management and Portfolio Committees. Before joining General Atlantic in 2012, Martín was a Managing Director at Advent International. Prior to that, he was Co-Founder and CFO of Submarino.com, a leading Brazilian online retailer that went public and was sold to Lojas Americanas in 2006. Martin started his career as a management consultant at The Boston Consulting Group. Thanks to Seba Kanovich @ dlocal for the introduction today. In Today's Episode with Martín Escobari: 1.) From Bolivia to Harvard to Leading General Atlantic: How did Martin make his way into the world of venture from a small town in Bolivia? How did being an operator going through a bust impact how Martin invests and works with founders? How does Martin advise young members on his team about surviving through a bust? 2.) Market Matters: Founders, Product or Market: Why does Martin believe the single most important element when investing is the market you are entering? How does Martin assess both market size and market growth? What does Martin believe makes a "beautiful business model"? What is the difference between good vs great? Why have we seen a generation of bad business models? How did Martin's analysis of Nubank's market lead him to turn them down? How did Martin change his approach to investing on the back of turning down Nubank? 3.) The Venture Landscape: What made Martin believe there was a downturn last year? What three signs always suggest we are in a bubble? As a result, how did General Atlantic retain their discipline when others did not? Where did they lose their discipline and invest at the top of the market? How does Martin analyse the performance of the crossover funds in the last 24 months? Who did well? Who did not? Do they remain in the market? Is Martin concerned by the exodus of capital out of South America with the bust? 4.) Martin Escobari: The Investor and Board Member: How has Martin's style of investing changed over the last decade? How does Martin reflect on his own price sensitivity? Does Martin engage in outcome scenario planning? What has been Martin's biggest hit? How did it change his mindset? How would Martin analyze his own style of board membership? How does Martin advise young board members gaining their first boards?

Hugo Barra is the OG of consumer hardware of the last decade. In Hugo's current position, he is the CEO @ Detect, building tools that empower people to understand their health and make informed, timely decisions. Before Detect, Hugo spent an incredible 4 years as VP of VR @ Meta with Oculus. Prior to Oculus, Hugo was in China as VP of Global @ Xiaomi, the 3rd largest phone maker in the world. Finally before Xiaomi, Hugo was a product leader @ Google for over 5 years including as VP of Android Product Management. In Today's Episode with Hugo Barra We Discuss: 1.) Entry into Product: How did Hugo make his way from Brazil to Silicon Valley and Beijing Product OG? What is one takeaway from Google, Meta, and Xiaomi that influenced the way Hugo approaches product today? What is 996 Chinese work culture? How does the experience of working and leading teams in China impact his approach to team building today? 2.) The Secret to Success in Hardware: Why is hardware so much harder than software? What are the main differences? What are the biggest challenges faced when building V1 and V2 in hardware? How much do you rely on data vs gut and intuition? What are some of Hugo's biggest consumer product hardware failures? What did he learn from them? 3.) Feature King vs Budget King: Previously Hugo has said, "in the beginning, there is only two types of consumers." What does he mean by this? How does that impact his approach to product building? Can a budget king product leader also be an amazing feature king leader? What is the difference in the two? Why is it harder to be a budget king product leader? What happens if you have both budget king and feature king in one product? What happens then? 4.) Product Management 101: How does Hugo define product management today? What does it really mean to Hugo? Gustav @ Spotify has said before, "details are not details, they are the product." How does Hugo think about this statement in terms of great product management today? When do product orgs start to break down? What are the catalysts? What can be done to stop this? 5.) Brand Marketing vs Product Marketing: What is the difference between product and brand marketing? Why does Hugo believe you should always start every product build with the press release? What is the difference between good and great in a press release? What do the best have? What are the single biggest mistakes founders and product leaders make in storytelling today? 6.) Masterclass in Hiring: Why does Hugo do 3-and-a-half-hour interviews when hiring new candidates? What are the benefits of their being so long? What does he want to achieve? What core questions does he ask every time? What differentiates good from great? How does he get people to really open up and show true vulnerability?

Brian Armstrong is the Co-Founder and CEO @ Coinbase, the easiest place to buy and sell cryptocurrency. Over the last 10 years, Brian has led Coinbase to today, a public company with over 3,500 employees and revenues of over $7.5BN in 2021. Brian also raised venture funding before going public from some of the best including Fred Wilson @ USV, Micky Malka @ Ribbit, Marc Andreesen @ a16z and Garry and Alexis at Initialized. Prior to founding Coinbase, Brian was a Product Manager @ Airbnb. In Today's Episode with Brian Armstrong We Discuss: 1.) Founding Coinbase: How did Brian make his way from PM @ Airbnb to founding Coinbase? What is Brian running from in his past? What is he running toward in his future? What does Brian know now that he wishes he had known at the start of Coinbase? 2.) Brian Armstrong: The Leader: What does "high performance" mean to Brian in leadership? How does Brian think about stepping off the treadmill for a second and appreciating what has been achieved? How does one celebrate as a team without creating laziness or arrogance? How has Brian most changed as a leader over the last 10 years? On reflection, what does Brian believe are his biggest weaknesses today? 3.) Crucible Moments in the Coinbase Journey: What does Brian mean when he says, "you need to be able to differentiate between a real emergency and a fame emergency?" What is the difference? When Brian made the speech to the Coinbase team on political views in the company, was that a real or fake emergency? What happened? What would he have done differently? Is the failed NFT launch, a real or fake emergency? What big mistakes were made? What are Coinbase doing to correct and improve them? "Bankrupt Coinbase" campaign on social earlier this year, real or fake emergency? What has been Brian's biggest lessons on how to deal with fake news? 4.) Crypto and The Ultimate Mission for Coinbase: What is different about this crypto winter from all other crypto winters? Why did Brian ban discussion on the market cap from employees within Coinbase? How does Brian maintain morale internally when everyone sees the stock at all-time lows? How does the Coinbase mission extend far beyond financial freedom for the world? What does Brian want Coinbase to be in 10 years?  

Michael Mauboussin is Head of Consilient Research at Counterpoint Global. Previously, he was Director of Research at BlueMountain Capital, Head of Global Financial Strategies at Credit Suisse, and Chief Investment Strategist at Legg Mason Capital Management. He is also the author of three incredible books, including More Than You Know: Finding Financial Wisdom in Unconventional Places, named in The 100 Best Business Books of All Time by 800-CEO-Read. Michael has taught at Columbia Business School since 1993 and received the Dean's Award for Teaching Excellence in 2009 and 2016. In Today's Episode with Michael Mauboussin We Discuss: 1.) Entry into Venture and Finance: What does Michael actually do as "Head of Consilient Research"? What does Michael know now that he wishes he had known when he entered finance? How did Michael and Bill Gurley meet in business school? What does Michael believe makes Bill such a special investor today? 2.) Booms and Busts: How This Compares? How does the current macro downturn compare to prior crashes Michael has worked through? What is the same? What is different? How do political and health events impact the macro? Why was 1987 the end of the world at the time? How did the recovery take place? How does Michael analyze the duration of bull markets vs the duration of recovery time? What advice does Michael give to young people today questioning if they are good investors? 3.) The Investment Decision-Making Process: How does Michael advise on the structuring of your decision-making process? What makes a good process vs a bad process? What can be done to remove politics from the decision-making process? What can be done to ensure all people, regardless of hierarchy feel safe in the process and feel they can share their thoughts without repercussions? What are the single biggest mistakes Michael sees people make in their decision-making process? How do you know when is the right time to change your process? 4.) Everything is a DCF: What does Michael mean when he says that "everything is a DCF"? How does Michael advise and apply this thinking to early-stage venture investors? How does Michael think through highly diversified portfolios vs super concentrated portfolios in venture? Items Mentioned in Today's Episode: Michael's Favourite Book: Consilience: The Unity of Knowledge by E.O Wilson

Raf Illishayev is the Co-Founder and CEO @ GoPuff, one of the market leaders delivering daily essentials in minutes. GoPuff’s latest funding round priced the company at a reported $8.9Bn in March 2021 and to date, Rafael has raised over $2.4Bn for the company from the likes of Accel, Softbank, Fidelity, Baillie Gifford, D1 Capital and more. Rafael has scaled the company to over 1/3 of the US with over 12,000 employees nationwide. In Today’s Episode with GoPuff's Rafael Ilishayev You Will Learn: 1.) From Student to Global CEO: How Raf came up with the idea for GoPuff and started the company as a student with no funding? What were the early signs of product-market fit that Raf observed in the early days? In hindsight, does Raf wish they had raised external funding sooner than they did? What would raising external funding sooner have changed about the way they run the business? 2.) The Rise and Fall of Quick Commerce: What are the core drivers that have led to capital drying up for players in the quick commerce space? With the changing environment, is it a race to profitability for all providers in the space? Is this the perfect time for GoPuff to acquire? What are the characteristics of businesses in the space that GoPuff would vs would not like to acquire? How does Raf see the quick commerce space looking in 5 years time? 3.) Getting to Profitability: The Levers That Matter: Customer Service: Why does Raf believe that all players pulling back on investing in customer service are making a massive mistake? What can be done instead? Delivery Time: Why does Raf believe the 10-minute delivery model is fundamentally unprofitable? How do GoPuff approach it as a result? Inventory: With a changing macro-environment, why does Raf believe it is prudent to focus more attention on alcohol and convenience goods? What do prior recessions show us about consumer spending patterns changing? Metrics: What are the single most important metrics which dictate the speed of getting to profitability? Why is the amount of orders a driver can deliver per hour the most important metric? 4.) Business Expansion Opportunities: How does Raf analyze the opportunity for GoPuff in Europe? Why does Raf believe they should have pulled out of Spain much sooner? Why are they so focused on the UK now? Why does Raf believe it is the right decision to stop investing in GoPuff pharmacy? Why is Raf so bullish on GoPuff kitchens? How does the unit economics of the kitchens compare to the core business for GoPuff? What are the positive effects of kitchens on GoPuff core product? What was the most recent disagreement the board has had when it comes to determining what to prioritize vs what not to? Mentioned in Today's GoPuff Episode: Raf's Mentor and Advisor: Emil Michael, Former Chief Business Officer @ Uber

Brian Singerman is a Partner @ Founders Fund, one of the best-performing funds of the last two decades. Among their portfolio, they have the likes of Airbnb, Facebook, Stripe, Anduril, and many more generational-defining companies. As for Brian, he has led investments in the likes of Affirm, Oscar Health, Wish, Asana, Oculus, and Postmates to name a few. Brian also sits on the board or is an observer to The Long Term Stock Exchange, Solugen, Cloud9, Modern Health, and of course, Anduril. Prior to Founders Fund, Brian spent a very successful 4 years as an engineer and executive at Google. In Today's Episode with Brian Singerman We Discuss: 1.) From Google to Befriending Sean Parker to Founders Fund: How Brian's friendship with Sean Parker led to his joining Founders Fund over 15 years ago? What does Brian believe makes Founders Fund such a unique fund? What does Brian know now that he wishes he had known when he started in venture? 2.) The Landscape Today: Where Are We Now? Why does Brian believe there is a huge price mismatch between private vs public companies? How does this impact the pace with which Founders Fund invest? Why does Brian not feel any pressure to invest in this environment? What are the 10 hypergrowth companies that Brian is looking to invest in today? What advice does Brian give to young investors today who are concerned at their first market correction and questioning if they are actually any good at this? 3.) Brian Singerman: The Investor: How does Brian reflect on his own investing style? What is he world-class at? What is he bad at? Why does Brian think boards are a waste of time? What is better than a board? Why does Brian not ever think about reserves? How does Brian answer LPs concerns when they cite them on the topic of cross-fund investing? What does Brian believe is the secret to venture capital? What elements make those at Founders Fund thrive? What characteristics make those that do not work out, fail? 4.) Founders Fund: The Firm: How does Founders Fund structure and optimize its decision-making process today? How does Founders Fund approach the hiring process for all new team members? What one question do they need to be able to clearly answer with all team members joining? How do Founders Fund approach the reference checking process for all new hires? What questions do they find most revealing of the true talent of the candidate? What are the single biggest hiring mistakes Brian has made? What did he learn from them? Items Mentioned in Today's Episode: Brian's Most Recent Investment: Anduril

Chris Sacca is the Founder and Chairman @ Lowercase Capital, one of the best performing funds in the history of venture capital with a portfolio including Uber, Stripe, Twitter, Instagram, Twilio, Docker and many more. From interviewing some of the world's richest married couples, how did gaining wealth change their relationship and marriage? What does Chris do to actively ensure his children remain hungry and know the value of money? Chamath Palihapitiya is Founder & CEO @ Social Capital. Social’s portfolio includes the likes of Slack, Yammer, Front, Intercom and Carta to name a few. What does Chamath mean when he says we need to think through the mindset of "infinite games" not finite games? How does this change how you think about money? How does Chamath think about his relationship to risk today as a result? Brad Gerstner is the Founder and CEO of Altimeter. Brad’s notable deals that he has helped lead include Snowflake, Mongo, Bytedance, Gusto, Unity, Okta, dbt, Modern Treasury, EPIC Games, Hotel Tonight and Zillow. What is the most important thing parents can do to ensure that despite wealth, their children remain grounded and ambitious? Why does Brad, despite being a billionaire, still live in a modest house and not spend on the excesses of life? How does Brad embrace essentialism with wealth? Cyan Banister is one of the most successful and renowned early-stage investors in the last decade. Her portfolio includes the likes of SpaceX, Uber, Affirm, Opendoor Postmates, Niantic and Thumbtack to name a few. Why did Cyan used to hate money? Why was she "anti-capitalist"? How does Cyan approach risk management today? Why does she invest every dollar she makes back into the ecosystem? George Zachary is a General Partner @ CRV, one of the nation's oldest and most successful early-stage venture capital firms with a portfolio including the likes of Airtable, DoorDash, Dropbox, Niantic and many more. What did George learn about how the way people view you changes with your increasing wealth? Why does George believe rich people like to hang out with rich people? Biz Stone is best known as the Co-Founder of Twitter and Medium. Biz is also an investor in the likes of Slack, Square, Intercom, Beyond Meat and Blue Bottle Coffee. What does Biz mean when he says, "wealth only serves to amplify the person you are?"

Vaibhav Sahgal is VP of Consumer Product @ Reddit where he has been for close to 5 years. Prior to his leading consumer product, Vaibhav spent 3 years as Head of Growth at Reddit. Before Reddit, Vaibhav spent an incredible 8 years at Zynga across different roles including Director of Product and GM for "Words with Friends". In Today's Episode with Vaibhav Sahgal We Discuss: 1.) Entry into Product + Growth: How did Vaibhav come to lead some of the best growth orgs in the world at both Reddit and Zynga? What are 1-2 of Vaibhav's biggest takeaways from working with Mark Pincus @ Zynga? What is the most painful growth lesson that Vaibhav learned that he is also pleased to have learned? 2.) WTF Really is "Growth": How does Vaibhav define growth today? What is it not? How does Vaibhav fundamentally differentiate between value connection and value creation? Is growth an art or a science? What tactics have died a death? What remains stronger than ever? 3.) Hiring Your Growth Team: How does Vaibhav advise founders on when is the right time to hire their first growth professionals? Where should they sit within the org? In product? In marketing? Standalone growth team? What are the biggest mistakes Vaibhav sees founders make when hiring their first growth hires? 4.) The Interview Process: How does Vaibhav structure the interview process for all new growth hires? What are the steps? What are the must-ask questions when hiring for growth? What are good answers? How can founders use case studies and data to determine the quality of a growth candidate? 5.) The Onboarding and Integration: What is the optimal onboarding process for all new growth hires? What are signs in the first 3 days that a growth hire will vs will not work out? What can leaders do to ensure growth hires are integrated with the rest of the teams? What are the biggest mistakes founders make when onboarding growth hires? Items Mentioned in Today's Episode: Vaibhav's Favourite Book: Andrew Chen: The Cold Start Problem

Emil Michael is the Former Chief Business Officer at Uber and is commonly referred to as Travis Kalanick's right-hand man. At Uber, Emil was instrumental in raising nearly $15BN from some of the largest investors in the world, making Uber the most valuable private tech company ever. Emil was also core to Uber's China strategy and led deals with Didi and Baidu. Before Uber, Emil spent 9 years at TellMe Networks where he was central to Microsoft raising their acquisition price from $300M to $800M. Emil is also an advisor to some of the greats including Raf @ GoPuff, Zach @ Codeacademy, Jared @ Fundera and many more. In Todays Episode with Emil Michael: 1.) From Politics to Travis's right-hand man at Uber: How did Emil make his way into the world of startups with TellMe networks? Harvard, Stanford, Goldman, Politics, which career shaped Emil the most? When Emil looks at his cohort of Ali and Hadi Partovi, Alfred Lin, and many others, what did they have that Emil believes is core to their success today? 2.) Negotiations 101: A Masterclass: What is Emil's framework for dealmaking? How has it changed over time? What are the single most important elements to remember when making deals? What are the biggest mistakes people make when negotiating? What is the right way to use leverage in negotiations? How can one handle an opponent that is emotional or irrational when negotiating? How did Emil make Steve Ballmer @ Microsoft increase his offer for TellMe from $300M to $800M? What is the single deal that Emil made that he regrets the most? 3.) Uber: The Journey to the Most Valuable Private Company: Why were Emil and Travis removed from Uber? Does Emil think it was fair? Is it true that Travis lost the support of the team? How did his removal take place? How did the Uber China deal go down with Didi? What got DiDi over the line on the deal? How did Emil raise $3BN from Saudi in just 60 days with Travis needing to attend only one meeting? 4.) Uber: The Review: How does Emil assess the management and performance of Uber CEO, Dara Khosrowshahi? If Travis and Emil were still in charge, what would Emil have done differently? Why does Emil think Dara and Uber have made a $30BN mistake in food delivery? Why does Emil think Postmates, Careem, and others have been the worst acquisitions in tech? 5.) The Venture Landscape: Emil entered the world of VC with Coatue, why did he decide that VC was not for him? How does Emil analyze the VC landscape today? Who are risers? Who are fallers? What are the single biggest points of misalignment between founder and VC? What are the core improvements that Emil would like to see made to the VC world? Items Mentioned in Today's Episode: Emil's Favourite Book: Sun Tzu: The Art of War

Kyle Harrison is a General Partner @ Contrary and one of my favorite writers on the venture space with his blog, Investing 101 2.0. Before joining Contrary, Kyle worked in the ranks of some of the biggest and best names in venture, starting with a spell at TCV before moving to Coatue and making his final stop at Index. Across firms, Kyle has led or participated in investments including Ramp, Pave, Anduril, Gitlab, Databricks and Snowflake to name a few. In Today's Episode with Kyle Harrison: 1.) From Film Lover to Technology Investor: How Kyle went from creating a professional services marketplace around film to joining the ranks of TCV and investing in breakout technology companies? What was Kyle's biggest takeaway from TCV? How did it impact his mindset? What was Kyle's biggest lesson from working with the Laffont's at Coatue? How did it change the way he thinks about price and market sizing? Why was Index such a transformational school of venture for Kyle? How did that experience change how he thinks about what it takes to be a great investor? 2.) The Death of So So Venture Firms: Why does Kyle believe many of the "so so" venture firms will die? What does Kyle believe makes a venture firm "so so"? Who is vulnerable then? How does Kyle think the lifespan and "death" of venture firms will change in the next decade? 3.) The Rise of "The Blackstone of Venture Firms": How does Kyle define "the Blackstone of VCs"? Who are they? With increasing fund sizes will we see VC returns denigrate to PE returns? How is the world of family offices changing the venture environment? Will we see more or less money flood into venture over the coming years? Of the incumbents, who has done "The Blackstone" model well? Why? Who has failed? Why? 4.) The Rise of Community in Venture: What does "community" really mean to Kyle? Why does he believe it will play such a prominent role in the way the best invest in the future? How have existing players failed to build, sustain and productize communities? What are the best opportunities for new entrants to create and utilise communities to invest? Items Mentioned in Today's Episode: Kyle's Favourite Book: Reinventing Knowledge: From Alexandria to the Internet

Lauren Schwartz is Vice President of Enterprise Sales at Fivetran, the leading platform for modern data movement. She has helped scale Fivetran's enterprise business from its infancy to a team of nearly 100, while more than tripling enterprise revenues. Previously, Lauren spent close to 4 years at Segment where she started as the first female AE and ultimately built and led sales teams in enterprise and growth. Lauren earned an MBA from Stanford Graduate School of Business after 6 years at Google where her enterprise sales career began.   In Today's Episode with Lauren Schwartz: 1.) How Being Rejected as an Eighth Grader Can Lead to World Class Sales Leader: How Lauren made her way into the world of enterprise sales with Google? Why, for a while, Lauren wanted to get away from the label of a salesperson? Why "salesperson" does not do the job of sales justice? Why does Lauren believe that one of the core traits the best salespeople have is being able to cope with rejection? How has Lauren been rejected? How did she respond? What changed their mind? 2.) The Sales Playbook: What, Who, When: How does Lauren define the term "sales playbook"? What are the nuances? Does Lauren believe the founder should always be the first sales rep? What are the core signs that a founder is now ready to bring in their first sales hires? What are the 3 biggest mistakes founders make when they hire their first sales reps? What are the core traits that the best early sales reps have? 3.) The Hiring Process: Building the Best Sales Team: How does Lauren structure the hiring process? What are the most unconventional but useful questions Lauren uses to determine the depth and quality of potential sales hires? What are the glaring red flags that Lauren looks for in this interview process? How does Lauren use case studies and deal reviews in the interview process to determine the quality of a candidate? 4.) Scaling the Machine: The Onboarding Process: What are the single biggest mistakes founders make when onboarding sales reps? How should sales team onboarding be structured? What materials should the founder have in place for the sales team to learn from on Day 1? How can sales leaders ensure new sales team members engage across functions?

Drew Houston is the Co-Founder and CEO @ Dropbox, for over 700 million users and +600,000 teams, Dropbox is the choice for storing and sharing their most important files. Prior to their IPO in 2018, Drew raised funding from some of the best including Sequoia, Index, Greylock, and IVP to name a few. Drew also currently sits on the board of Meta and is a seasoned angel with a portfolio including Gusto, Scale AI, Pilot and Superhuman to name a few. Prior to Dropbox, Drew founded Accolade, a bootstrapped online SAT prep company he started while in college. In Today's Episode with Drew Houston We Discuss: 1.) Entry into Startups and Y Combinator: How did Drew make his way into the world of startups with an SAT prep planning startup? How did Drew convince Paul Graham to accept him and Dropbox into Y Combinator? If we are all a function of our pasts, what is Drew running towards and what is he running away from? 2.) Drew Houston: The Leader and CEO: How does Drew define "high performance" today? How would Drew describe his style of management? How has it changed over time? How did taking an enneagram test change how Drew leads? What did he learn? What have been Drew's biggest hiring mistakes? What mistakes does he see others make? What have been Drew's biggest lessons in how to let people go the right way? 3.) Crucible Moments: Getting Sequoia, Acquisitions and Steve Jobs: How did Drew convince the Sequoia team to invest in Dropbox? How did it all start in a rug shop thanks to Pejman Nozad @ Pear? Has Drew had opportunities to sell the company? Why did he not take them? How does he advise founders on the decision to sell or not? How did Drew come to meet Steve Jobs? How did the meeting go? 4.) Drew Houston: AMA: Is Dropbox a B2B company or a B2C company? What is the hardest element of Drew's role with Dropbox? What has Drew recently changed his mind on? When press cycles were against him, how did Drew get through those tough times? What is Drew's biggest takeaway from joining the Meta board? Items Mentioned In Today's Episode: Drew's Fave Book: High Output Management by And

Tristan Handy is the Founder and CEO @ dbt, a data transformation tool that enables data analysts and engineers to transform, test and document data in the cloud data warehouse. To date, Tristan has raised over $400M from the likes of Sequoia, Altimeter, Coatue, ICONIQ and GV with the latest funding round valuing the company at $4.2BN. Prior to founding dbt, Tristan was the VP Marketing @ RJ Metrics and got his break in the world of startups through former 20VC guest, Anthony Casalena with a Director of Operations role at Squarespace. In Today's Episode with Tristan Handy: 1.) Entry into Startups: How did Tristan make his way into the world of startups with his first role at Squarespace? How did Tristan's time with Squarespace impact how he builds dbt today? What does Tristan know now that he wishes he had known when he founded dbt? 2.) Our Jobs Are Not That Hard: Why does Tristan believe that our jobs are not that hard? If going down this line, how does Tristan hire? What does he look for? How does he test for it? When does experience matter? When does it not matter? 3.) dbt: The Company Why does Tristan believe that remote work does not work? What financial packages have dbt put in place to allow their employees this physical interaction? What does Tristan believe is the hardest element of building a hybrid company? When does everything start to break? What are the biggest lessons Tristan and dbt have taken from Gitlab? 4.) Tristan: The Leader How does Tristan conduct and execute on the best performance reviews? How does Tristan create an environment of safety where people feel they can be honest and transparent? What are the elements that you cannot be transparent on? Where does transparency break down? 5.) Trading Freedom for Scale: dbt could have been a small and super profitable company, why did Tristan decide to trade off the freedom and raise big from VCs? How did Tristan raise over $414M without ever talking about an efficiency metric? Is Tristan concerned about living into the $4.2BN valuation in what is a very different time? With the benefit of hindsight, is Tristan pleased he went big and raised venture?

Gustav Söderström is Spotify’s Chief Research & Development Officer. He has the CPO & CTO responsibility, overseeing the product, design, data, and engineering teams at Spotify and is responsible for Spotify’s product strategy. Gustav is also an entrepreneur and investor who has founded and sold startups that he co-founded to Meta’s Oculus in 2014 and then also his first startup which he co-founded and led as CEO, up until their acquisition by Yahoo! Gustav is also the host of the podcast mini-series  -- Spotify: A product story -- which offers a glimpse into the decisions that have guided Spotify’s product evolution. In Today's Episode with Gustav Söderström 1.) From Selling Companies to Yahoo and Meta to Leading Spotify's Product: How did Gustav first make his way into the world of tech and startups? What was it that made Gustav so compelled to join Daniel Ek and build Spotify? What does Gustav know now that he wishes he had known when he started? 2.) "Never Fight a Macro Wind": What does Gustav mean when he says "never fight a macro wind"? What models can product leaders construct to measure the size, importance and timing of a macro wind? What can product leaders do to change the macro wind and have it blowing in their back and not their face? When did Gustav experience this? What did he change to have the wind blow in his back? How did this alter his mindset and mentality? 3.) "Do Something Completely Different to the Competition": Why does Gustav believe startups should do the complete opposite to the competition? Does this change if your competition is other startups vs incumbents? What is the story of how Spotify did the complete opposite to Youtube? Why did it work? On the flip side, when did Spotify do the complete opposite and it did not work out? 4.) Mastering the Learning Process: How does Gustav approach the learning process for all new skills and disciplines? Why does Gustav believe that all technology leaders have to be the master of their domain? How did this lead to Gustav going back to University to study machine learning? What are the single biggest mistakes people make in the learning process? 5.) Gustav: The Product Leader: Why does Gustav believe that product is 100% science and not art? What does Gustav mean when he says, "talk is cheap and so we should do more of it"? How does Gustav structure internal debates? Who sets the agenda? Who is invited? What makes a good vs a bad internal debate? How does Gustav make everyone feel safe? What can leaders do to ensure an environment where everyone feels they can debate with the boss? 6.) Spotify: The Crucible Moments: What is Gustav's favourite near-death experience in the Spotify journey? Why did Spotify decide to make the move into podcasting and video? How does that additional complexity change the product paradigm of an audio-only platform? How do the single most impactful platforms in the world approach market expansion and when to add new products? What are the best companies in the world not merely technology innovations but also business model innovations? Items Mentioned in Today's Episode: EXCLUSIVE NordVPN Deal ➼ https://nordvpn.com/20vc Try it risk-free now with a 30-day money-back guarantee!

Brad Gerstner is the Founder and CEO of Altimeter, a life-cycle technology investment firm that manages public and private portfolios. Brad has personally participated in more than 100 IPOs as a sponsor, anchor, and investor. Brad’s notable deals include Snowflake, Mongo, Bytedance, Gusto, Unity, Okta, dbt, Modern Treasury, EPIC Games, Hotel Tonight, and Zillow. Prior to founding Altimeter, Brad was a 3-time co-founder where he sold all three businesses (to IAC, Google, and Marchex), a founding principal at General Catalyst; a securities lawyer, a former Deputy Secretary of State of Indiana, and a pilot. In Today's Episode with Brad Gerstner We Discuss: 1.) From Humble Beginnings in Indiana to 100 IPOs: When did Brad realize his original love of finance and entrepreneurship? What one single question does Brad ask all potential new recruits to determine if they have hustle? What does Brad know now that he wishes he had known at the beginning of his career? 2.) The Power Law and Supercycles: What is a power law? Why is it the single most important thing in investing? How do the best investors in the world build a framework around supercycles? How does Brad approach market sizing? How does Brad think about market creation when aligning that to his thesis of investing in power laws? How does Brad determine if a large opportunity is a "super-cyle" or a short, time-stamped fad that is unsustainable? How does Brad assess the importance of market timing? 3.) Building Anti-Fragile Portfolios: Portfolio Construction: Why does Brad disagree that the answer to risk mitigation is portfolio diversification? How many companies is enough companies for a diverse portfolio? Price Sensitivity: How does Brad reflect on his own relationship to price? How does this process and mindset change on re-investments? What is needed for Brad to re-invest? Time to Exit: How does Brad analyze when is the right time to exit a position? What are the single biggest mistakes people make when it comes to timing their exit? 4.) The Venture Landscape: Today, What is Happening? Why does Brad believe what has happened over the last 24 months is a great disservice to founders? What are the biggest examples of a complete lack of investor discipline? Why does Brad believe that for all positions valued over $500M, we should apply a 20% discount? Is today's pricing actually just the new normal? How has the public market pricing impacted the deployment of growth stage checks? How will this play out in the next 12 months? Why does Brad believe there is "not blood on the streets yet"? How does the speed of interest rate change impact our ecosystem so dramatically? Items Mentioned in Today's Episode: Brad's Favourite Book: The Snowball: Warren Buffet and the Business of Life

Kevin Weil is President of Product and Business @ Planet and Operator in Residence @ Scribble Ventures. In the past, Kevin has been Head of Product at Twitter, Instagram, and Novi (the digital currency effort within Facebook). During his seven years at Twitter, he helped the company scale from 40 to 4000 people and from $0 to $2B in revenue. He then moved to Instagram in 2016 to lead the product and data teams and led through an inflection point as Instagram grew from 400M to over 1B users, including launching Instagram Stories. Kevin then co-founded Diem (formerly known as Libra) and Novi and built both for three years before moving to Planet in 2021. If that was not enough, Kevin is also on the board of Strava, the Nature Conservancy, and the Black Product Managers Network. In Today's Episode with Kevin Weil We Discuss: 1.) Lessons From Leading Product for Instagram and Twitter: What does Kevin believe makes Instagram so inherently good at product? How did leading product for Instagram change the way Kevin thinks and operates? What are 1-2 of Kevin's biggest lessons from working with Kevin Systrom, Instagram's Founder? What are the biggest takeaways for Kevin from leading product at Twitter? 2.) Launching Products, Customer Discovery and Product Sessions: What were Kevin's biggest learnings from launching Instagram stories? How did Kevin's conviction impact the product building and success of Instagram stories? How does Kevin advise founders on the best way to approach customer discovery? What are the best questions to ask to reveal the truth? How does Kevin approach product testing today? Why does Kevin not like softly softly testing new products? 3.) Kevin Weil: Leadership 101 What are some of the biggest leadership mistakes that Kevin made in his time at Twitter? How does Kevin approach decision-making frameworks? How does one balance the speed vs the quality of the decision? What makes a great product strategy? Where do so many go wrong in their product strategy? How do the best leaders communicate with their team? How does this change over time? What is Kevin's preferred medium and style of communication with his teams? 4.) Kevin Weil: The Athlete, Father and Husband: Kevin is an ultra-marathon runner, what does his training routine look like? What 1-2 changes has Kevin made that have had the biggest impact on performance? How does Kevin manage, investing, advising, training and being a father and husband?  

Geoff Lewis is a Founder and Managing Partner of Bedrock, one of the breakout and new venture firms of the last decade, famously in search of narrative violations. He serves or has served on the Board of Directors for companies including Lyft (NASDAQ: LYFT), Nubank (NYSE: NU), Epirus, and Vercel. Additionally, he has led sizable early-stage venture capital investments in dozens of companies including Upstart (NASDAQ: UPST), Tilray (NASDAQ: TLRY), Leafly (NASDAQ: LFLY), Wish (NASDAQ: WISH), Workrise, and Rippling. Prior to founding Bedrock, Geoff served as a partner at Founders Fund for several years. In Today's Episode with Geoff Lewis: 1.) Meeting Parker Conrad: A Generational Defining Entrepreneur: How did Geoff first come to meet Parker Conrad, over a decade prior to making the first Rippling investment? What was it about Parker that compelled Geoff so much in the early days? How did Geoff analyze the chip on Parker's shoulder from Zenefits? How does he believe it has driven him with Rippling? 2.) Searching for Narrative Violations in Rippling: Why does Geoff believe Parker himself is a "narrative violation"? What does Geoff believe is the foundational narrative violation in the way Parker is building Rippling? Rippling has a large portion of its team as former founders, how does Geoff believe this impacts the culture of Rippling? What does Geoff believe are the single biggest barriers to Rippling being the "App Store for Business"? On the upside case, if Rippling goes right, how big could this be? 3.) Rippling: The Financing: What has been Geoff's biggest lesson on price and price sensitivity that he has learned through Rippling? Why does Geoff never do uncapped notes? Why did Geoff break that rule with Rippling? What gave Geoff the conviction to write Bedrock's largest ever check in Rippling's Series D? What was the massive mistake that both Geoff and Bedrock made in not financing their Series C? 4.) Geoff Lewis: The Investor What single trait does Geoff believe all generational defining founders share? How does he test for it? Does Geoff believe he has a chip on his shoulder today? How has his relationship to the chip on his shoulder changed over time? To what extent does Geoff engage in outcome scenario planning when making investments? What upside scenario plan does Geoff need to be able to see for him to make an investment? Has Geoff ever lost money in an investment? What were his takeaways from this experience?

Parker Conrad is the Founder & CEO @ Rippling, the company that lets you easily manage your employees’ payroll, benefits, expenses, devices, apps & more—in one place. To date, Parker has raised over $697M for Rippling from some of the best including Sequoia, Founders Fund, Greenoaks, Bedrock, Kleiner Perkins and Initialized to name a few. Prior to founding Rippling, Parker was the Co-Founder and CEO @ Zenefits and if that was not enough, Parker is also a prominent angel having invested in Census, Pulley and then also AgentSync and TrueNorth, alongside 20VC Fund. In Today's Episode with Parker Conrad: 1.) Entry in Startups and Zenefits: How did Parker make his way into the world of startups? How did Parker end up being kicked out of his own company, Zenefits? How did he respond? How did that experience of being kicked out of Zenefits inspire him to build Rippling? 2.) Parker Conrad: The Leader: How does Parker define "high performance"? How would Parker describe his leadership style today? Why does Parker fundamentally disagree that with speed comes a trade-off in quality? How does Parker ensure Rippling does all things fast and to the best of its ability? How would Parker break down his decision-making framework today? How does he decide what to prioritize vs not? How does he decide what to delegate vs not? What are Parker's biggest insecurities in leadership today? How have they changed over time? What does Parker do to combat and mitigate them? 3.) Rippling: The Compound Startup How does Parker define a compound startup? What types of business do this verticalized approach work for vs not work for? What does Parker believe are the 4 core benefits of this approach? What are the single biggest challenges of building a compound startup? 4.) Rippling: The Economics: How does this compound startup approach impact ability to cross-sell? How much net new ARR today comes from cross-sell? What have been some of Rippling's biggest lessons on what it takes to do cross-sell so effectively? How do the margin profiles differ across their different products? How have the margin profiles changed over time? Why does Parker not believe that most startup margins are accurate? How does the compound startup approach change the amount invested in R&D? How does that impact the fundraising requirements of the business? 5.) Rippling: The Partner Ecosystem: How does Rippling think about building out the best partner ecosystem? What will it take for that to work? Why do Rippling want to introduce services that compete with their own products? Why do they not only build their own? How do the margins differ when comparing revenue share on partner products vs Rippling products? What are the single biggest barriers to this partner ecosystem working?

Tarek Mansour is the Founder and CEO @ Kalshi, the first regulated exchange where you can trade directly on the outcome of events. Tarek has raised funding from some of the best including Alfred Lin @ Sequoia, Ali Partovi @ Neo, Ron Conway, Charles Schwab and Henry Kravis. Before founding Kalshi, Tarek worked at the likes of Citadel, Palantir and Goldman Sachs, in various different roles. In Today's Episode with Tarek Mansour We Discuss: 1.) Entry into Startups: How did Tarek make his way from a nerdy kid in Lebanon to having his first startup funded by Sequoia and billionaires likes Charles Schwab and Henry Kravis? How did his mother's continuous desire for excellence change Tarek's mindset? What are the biggest lessons that Tarek took from his mother's strict parenting and how did he apply them to how he manages the team at Kalshi today? 2.) What it Takes to Succeed: Why does Tarek believe that the world does not want your startup to exist? In that case, what are the core traits that founders need to fight this headwind? Does Tarek believe in work-life balance? What are some of the struggles of this? Does Tarek believe you should work on your weaknesses or double down on your strengths? 3.) Building the Team: Does Tarek believe that naivete is a strength or a weakness? At what point does it change between being a strength to being a weakness? Does Tarek prefer to hire more senior experienced people or younger hustlers with more energy? What have been the single biggest hiring mistakes that Tarek has made? How has it changed his approach to team building? What is the one single trait that if Tarek sees, he will not hire? How does Tarek make the interview process both fun but different and challenging? Where do so many founders make mistakes in how they construct the hiring process? 4.) Tarek Mansour: AMA: What have been the single biggest lessons from working with Ron Conway and Alfred Lin? What are some of Tarek's biggest insecurities in leadership today? What does Tarek know now that he wishes he had known at the beginning of his time with Kalshi? What would Tarek most like to change about the world of startups? Items Mentioned in Today's Show: Tarek's Favourite Book: Never Split the Difference: Negotiating as If Your Life Depended on It 

Kipp Bodnar is the Chief Marketing Officer of HubSpot, where he sets HubSpot’s global inbound marketing strategy. Prior to his role as CMO, Kipp served as VP of Marketing at HubSpot, overseeing all demand generation activity worldwide and building out the EMEA and APAC marketing teams. Kipp serves as a marketing advisor for SimplyMeasured, InsightSquared and Guidebook. Kipp is the co-author of “The B2B Social Media Book: Become a Marketing Superstar by Generating Leads with Blogging, LinkedIn, Twitter, Facebook, Email, and More.” In Today's Episode with Kipp Bodnar We Discuss: 1.) The Journey to CMO @ Hubspot: How Kipp made his way into the world of marketing and came to be CMO @ Hubspot? What does Kipp know now that he wishes all CMOs knew when they started? 2.) Choosing The Channel: How does Kipp advise founders on which channel they should focus on? What is the framework which will tell them which channel is right for them? How many different channels should they try? How focussed should they be? Should they have independent teams for each channel? How do the best founders allocate resources to new channels? How do you know when one is not working and you need to stop? When do you just need to keep going and persisting? What have been some of Kipp's biggest mistakes when entering new channels? 3.) Product Marketing, Brand Marketing and Founders Marketing: How does Kipp advise founders who say that, "social and personal brand is just not for them"? In what two ways does Kipp believe that all businesses are constrained? Does Kipp agree that the state of product marketing has never been worse? What is truly great product marketing to Kipp? How does Kipp distinguish between good and great brand marketing? How has what it takes to be great at brand marketing changed over time? 4.) The Best Marketing People: What are signs of clear 10x performers in marketing? What advice would Kipp give to someone aspiring to be a CMO? What mistakes do 95% make that they should change? How do the best CMOs manage up and manage their team? Why does Kipp compare the role of the CMO to the general manager in NFL teams? Why does Kipp believe the role of the CMO is a lonely one? What are the hardest elements? What framework for learning does Kipp use to learn all new topics? What works? What does not?

Paul Davison is the Co-Founder and CEO @ Clubhouse, the startup that believes people are at the centre of every moment, providing a platform to talk with friends and meet new friends. To date, Paul has raised over $310M with Clubhouse from a16z, DST, Elad Gil, Naval Ravikant, and many more. Prior to co-founding Clubhouse, Paul was the Founder of Highlight, a location-based consumer social service backed by Benchmark. Before Highlight, Paul actually spent time at Benchmark as an EiR. In Today's Episode with Paul Davison We Discuss: 1.) Entry into Startups: How Paul came to found Highlight in the early days of consumer social? What elements worked with Highlight that he took with him to Clubhouse? Which elements did not work that he learned from? 2.) Clubhouse: What Worked: What does Paul believe are the primary reasons that Clubhouse grew so fast? What metrics does Paul use to determine true product-market-fit and stickiness? What is good retention on Day 1, Day 7 and Day 30? How important is 12-month retention? 3.) Clubhouse: What Did Not Work: COVID: Does Paul believe that Clubhouse was the COVID antidote we all needed? How sustainable is that if so? What trends make it more sustainable? Live Does Not Work: How does Paul respond to Mike Mignano's comments that "live does not work"? Why does Paul believe that Clubhouse is not a content platform? Quality: Does Paul agree that the quality of live is not as good as the quality of produced content? Is that a problem? If the quality is worse, what is significantly better about live? 4.) The Future of Social: Does Paul agree that we are seeing the disregard of the once hailed social graph in favour of a new era of recommendation media? What does this mean for Clubhouse? With the rise of the likes of BeReal, how does Paul think about the importance of authenticity in the next wave of consumer social? How does Paul forsee Web3 and the next generation of consumer social being interlinked? What will it take for Web3 to break through? What are the core barriers today? Does Paul agree that the best consumer social tools empower creators with Superhuman powers? 5.) Lessons on CEOship: What are Paul's biggest lessons on successful company building? How does Paul manage the criticism and negativity of the press personally? How does Paul maintain the morale internally when the press cycle is so negative? How has Paul adapted himself to gain a thicker skin and not pay as much attention? Items Mentioned in Today's Episode: Paul's Favourite Book: Reality Is Not What It Seems: The Journey to Quantum Gravity, Information: A History, a Theory, a Flood

Julio Vasconcellos is the Founder and Managing Partner @ Atlantico, one of the leading early-stage funds in Latin America. Prior to the world of venture, Julio got his break in the world of startups as Facebook’s first country lead for Brazil. Julio then went on to co-found Peixe Urbano, a company he scaled to over 1,200 employees and $100M+ in revenue. Post the sale of Peixe Urbano, Julio became an EiR @ Benchmark Capital where he met Scott Belsky. Scott and Julio went on to co-found Prefer, a Benchmark backed company transforming the future of work. If that was not enough, Julio has a stellar angel track record with prior investments in the likes of Ipsy and Quinto Andar. In Today's Episode with Julio Vasconcellos We Discuss: 1.) Entry into Startups: What are 1-2 of Julio's biggest takeaways from being Facebook's first hire in Brazil? What does Julio know now that he wishes he had known at the start of his career in startups? 2.) Lessons from Scaling Peixe Urbano to $100M in Revenue: How does Julio advise founders on when is the right time to launch a second product or market? How does Julio advise founders on the right balance between growth and unit economics? When times are tougher, should founders cut fast or cut slower? What is irreversible? What are the single biggest and worst things to break in hyper-scaling? 3.) Investing: Why Not Enough Play To Win: What is more important, a great market or a great founder? Why do not enough VCs today play to win? If they do not play to win, what do they play to do? Why is greed the number one enemy of venture returns? What are the single biggest investing lessons Julio has learned from Benchmark Founder, Andy Rachleff? How have they impacted his investing mindset? Why does Julio believe you can have a close relationship with founders as an angel and not a VC? How did Julio's approach to investing change with the transition from angel to VC? Does Julio believe that boards really add any value? If so, how? What is Julio's biggest investing hit? How did it change his approach? What is his biggest miss? How did that impact his mindset? 4.) The Future for LATAM: Is Julio as concerned as I am by the removal of growth stage capital from the LATAM ecosytem? Does this mean a higher mortality rate for LATAM companies? How does Julio advise founders? How did COVID adoption of technology in LATAM fundamentally differ to the US?

David Lieb is one of the product OGs of the last decade. As the founder of Bump David pioneered how over 150M users shared data, contacts and more before the company was acquired by Google. At Google, David took this one step further by creating Google Photos, which he has led with immense success for the last 9 years. In the last few weeks, David announced his latest move, to join Y Combinator, one of the world's leading accelerators as a Visiting Group Partner. If that was not enough, David also has a stellar angel portfolio with the likes of Rippling, Flexport, Tally, Maven and many more. In Today's Episode with David Lieb We Discuss: 1.) Entry into Product: How did an idea at business school turn into Bump and ultimately the creation of Google Photos? What are the single biggest mistakes David made with the early Bump product? What does David know now that he wishes he had known at the start of Bump? 2.) Scaling the Team Alongside the Product: What is product-market fit to David? What is it not? What are the single biggest mistakes founders make when they think they have it? What should founders do first and most importantly, when they do have it? Why does David believe individual user data is more important than relying on data? 3.) Product: Art or Science: Why does the description we have for product managers need to change? How does David determine when to act on customer feedback vs stick to the current product plan? What is the right way to do customer discovery? What questions are best to ask? Where do founders make the biggest mistakes in customer discovery? Ultimately, is product more art or science? Is this changing with ever-increasing data? 4.) Product: The Process: How does David conduct product reviews? What are the biggest mistakes founders and product leaders make when managing product reviews? Who is invited? Who sets the agenda? Who determines who is accountable for what? How do product reviews change in a world of Zoom? What is better? What is worse? What can product leaders do to build culture in remote worlds? How can product leaders make everyone feel safe and comfortable to share how they feel, regardless of seniority, in product reviews? Items Mentioned in Today's Episode: David's Best Performing Investment: Flexport

Seba Kanovich is the CEO @ dlocal, the #1 payments leader with a single solution focused on Latin America and other emerging markets. In June 2021, dlocal raised $617M in their NASDAQ IPO listing valuing the company at nearly $9BN. Before their IPO, dlocal raised from some of the best including General Atlantic, Bond Capital, and Oren Zeev to name a few. Prior to dlocal, Seba was CEO @ AstroPay, a leading payment solution provider in Emerging Markets. In Todays Episode with Seba Kanovich We Discuss: 1.) The Journey to CEO of an $8BN Company: How Seba made his way to the role of CEO of an $8BN company through dinner at his mother-in-law's house? What does Seba know now that he wishes he had known when he first became CEO? 2.) Leadership 101: What does "high performance" in business and leadership mean? How important are velocity and speed of execution in startups? When should one trade speed for quality? Where is the nuance? How does Seba approach prioritization? What framework does he use to determine what to focus on? How does Seba think through effective delegation? How can leaders determine what only they can do? 3.) Leadership: The Challenges and Lessons: What are Seba's biggest insecurities in leadership today? How does he manage them? How have they changed over time? What is the single most painful leadership lesson Seba has learned that he is also pleased to have learned? What gets easier with scale as a leader? What gets harder? In a scaling organization, what is the first thing to break? What can be done to mitigate this? 4.) The Funding and The IPO: Why did dlocal bootstrap for 4 years instead of raise funding? How did that process change their mindset toward capital efficiency? What was good about it? What was bad? What are the single biggest advantages great investors can bring to the table? Why did Seba decide 2021 was the right time to go public? What was the biggest surprise about going public? What is better and what is worse about being a public company? Items Mentioned in Today's Episode: Seba's Favourite Book: Steppenwolf by Herman Hesse

Eleanor Dorfman is a Sales Leader @ Retool, the company that allows you to build internal tools, remarkably fast. Prior to Retool, Eleanor joined Retool when there were only three account executives and has scaled the sales org sales to over 30 AEs, many SEs, and an entire SDR team. Before Retool, Eleanor was at Segment, where she built out the company’s customer success operations team before pivoting to creating an expansion sales team, renewals team, and a new business sales team. Finally, before Segment, Eleanor made her way into startups, starting as an unpaid intern at Clever, just four years later, Eleanor was Head of Customer Success and Solutions Engineering. In Today's Episode with Eleanor Dorfman We Discuss: 1.) Entry into Sales from Working with the US Education Department: How did Eleanor get her first role as an unpaid intern at Clever? What are 1-2 of her biggest takeaways from her time at Segment? What are the biggest advantages of sales reps having experience in customer success? 2.) The Sales Playbook: How does Eleanor define, "a sales playbook"? When does it need to be created? Does it need to be the founder who creates it or can it be a Head of Sales? Is it possible to run a PLG and enterprise motion from Day 1? How does this change your sales playbook? How does Eleanor advise founders on when is the right time to layer on an enterprise motion, on top of a PLG motion? 3.) Who, What and When: Building the Sales Team Should founders hire a Head of Sales first or sales reps first? If sales reps, should founders always hire sales reps in two's? How does Eleanor structure the hiring process for all new sales team recruits? What are the clearest signals of 10x sales hires? What are red flags in the interview process? How does Eleanor use demo's and case studies to determine technical ability? 4.) The First 30, 60 and 90 Days: The Onboarding: What is the right structure for all new sales hires to be onboarded? Why does Eleanor believe you will always hire your Head of Sales Enablement too late? What are the signs that now is the right time to hire your Head of Sales Enablement? What tools, materials and resources can founders provide to shorten the ramp time for new AEs? What are the single biggest mistakes founders make in the onboarding of new sales reps?  

Will Quist is a Partner @ Slow Ventures. Over the last decade, the team at Slow Ventures have invested in the earliest rounds of over 500 companies including Robinhood, NextDoor, Airtable, Solana and many more. As for Will, prior to Slow he spent over 8 years at Industry Ventures and before industry, cut his teeth in the world of finance at Banc of America. In Todays Episode with Will Quist We Discuss: 1.) Entry into Venture: How Will made his way from 6th generation San Francisco to Partner @ Slow? What are 1-2 of the biggest takeaways from his early 1-1s with Don Valentine? What does Will know now that he wishes he had known when he started in venture with Industry? 2.) WTF Really is Venture Capital? Why does Will believe that 95% of venture capital today is not really venture capital? What is true venture capital in Will's mind? How does Will divide the world of VC into two with; venture classic and new venture? How are they different? How are their return profiles different? 3.) The Questions: Discovering Greatness: Why does Will believe “for the most part, investors across asset classes are just asking the same questions”? What are those questions? What different answers are each looking for? What are the 5 core questions that will needs to understand to determine conviction and accurately price an asset? How does Will think through and analyze the question when meeting founders of; “what needs to come true for this business to become a great business”? 4.) The Future of Venture Capital: How does Will predict the venture capital ecosystem will look in 5 and then 10 years? What are the most concerning traits of the venture ecosystem for Will today? Who will be the winners of the next decade? Who will be the losers? What happens to the crossover funds? What will happen to Tiger?

Mike Mignano is a Partner @ Lightspeed, one of the most successful venture firms of the last decade with a portfolio including the likes of Snap, Affirm, Epic Games, Mulesoft and more. As for Mike, prior to venture, he was Head of Talk for Spotify where he led the podcast, live, and video businesses for the world’s leading audio streaming platform. Michael came to Spotify through their acquisition of Anchor, a company he co-founded and is credited for democratizing podcasting globally. Mike has also been a prolific angel investor with a portfolio including Cameo, Pipe, Sandbox VR and Stir. In Today's Episode with Mike Mignano We Discuss: 1.) Exclusive News: What exclusive news does Mike have to share today? What would Mike most like to change about the way founders experience the product of venture capital? How can VCs be better? What is Mike most nervous about in the new role? 2.) The World of Social is Changing Forever: Why does Mike believe there has never been a better time for the next social media giant to be born? Why are the largest social giants leaving behind the social graph? What is recommendation media? Why is it a better business model? How does the shift from social graph to recommendation media change the way large social giants operate and interact today? 3.) Startups: Risers, Fallers and Is There Room For Another Giant? What does Mike believe Clubhouse did well? What was their undoing? Does Mike believe BeReal is defensible? What features make it both sticky and defensible? Will TikTok be a $2 trillion dollar company? Will Meta catch TikTok or have they gone too far ahead? Will OpenSea be able to sustain and make the market for NFTs, despite crypto crashing? Should startups be concerned about large social giants "copying" their features? What does true defensibility look like in consumer social today? 4.) Angel Investing: Hits, Misses and Lessons: From writing over 50 angel checks, what are the single biggest lessons Mike has learned? What has been his biggest hit? How did that change the way he thinks about investing? What has been his biggest miss? In what way did that change how he invests? What advice does Mike give to all angel investors looking to invest today?

Rene Haas is the CEO @ Arm. The technologies that Arm creates are used in over 230+ Bn devices with everything from sensors to smartphones to servers. In 2016 Softbank made Arm it's largest ever acquisition with a reported price of $32Bn. As for Rene, he was appointed CEO in February 2022 having spent the last 8 years in numerous different roles within the company. Before Arm, Rene was Vice President & General Manager of the Computing Products Business Unit at Nvidia where he enjoyed a very successful 7 years with the team there. In Today's Episode with Rene Haas We Discuss: 1.) Entry into Tech from Eastman Kodak: How did Rene make his way into the world of technology and innovation? What are 1-2 of the biggest takeaways from his 7 years at Nvidia? How did working with Jensen impact his leadership approach and philosophy? 2.) Decision-Making in Leadership: What is the single biggest mistake leaders make when making decisions today? How does Rene balance the trade-off between speed vs quality of decision? At what point does Rene believe leaders have enough data to make a decision? What does Rene know now that he wishes he had known when he started on decisions? 3.) Scaling the Org and Remaining Nimble: Agile: How does one retain the speed and agility of a startup when one is the size that Arm is today? Ambition: How does Rene as a leader inspire the same level of ambition and vision in his team when Arm is as large as it is? Risk: How does Rene encourage his teams to take large risks when they have so much more to lose? Breakage: What are the first things to break in scaling? What can leaders do to get ahead of them? 4.) Leadership 101: What really is strategy? What is it not? What mistakes do all leaders make when it comes to strategy? How does Rene define "high performance" in leadership? How has his style of leadership changed over time? How does Rene approach vulnerability in leadership? What are the pros and cons?  

Annie Pearl is the CPO @ Calendly, the company that makes scheduling meetings simple and painless. The company now has over 10M users around the world and over 50,000 companies loving the product. As for Annie, before Calendly, Annie led Glassdoor's product vision and user experience, managing a 70 person product and design org. Prior to Glassdoor, Annie led enterprise product teams at Box both before and after their 2015 IPO. If this was not enough, Annie is also on the Board of WorkRamp and Well Health. In Today's Episode with Annie Pearl We Discuss: 1.) Entry into Product From Consulting: How did Annie make her way into the world of product and come to lead product teams at Box and GlassDoor? What are 1-2 of her biggest takeaways from her time at Box and GlassDoor? How did they impact her product mindset? What does Annie know now that she wishes she had known when she started in product? 2.) PLG vs Enterprise: What, When, How: Is it possible to do PLG and top-down enterprise strategy together from Day 1? Why does every PLG company eventually have to adopt an enterprise strategy? What are the single biggest challenges companies face when moving to enterprise? How do founders know when is the right time to make this transition? How do founders need to restructure their org to make the transition to enterprise? 3.) Building the Product Bench: Hiring: When is the right time to hire your first product leader? What are the core signals? What are the core character traits needed for a first product leader? How do we specifically structure the interview to test for them? Who do we bring into the interview process from other parts of the org? Do we do case studies with candidates? If so, how long do they have with the data? What is the difference between good vs great with case studies? 4.) Product Strategy, Reviews and Alignment: How does Annie assess how often product strategy should be reviewed? When should it change? How does Annie approach post-mortems? What is the right way to structure them? How does Annie create alignment between sales and product? Why is this so important? What is the single biggest product mistake Annie has made? What did she learn?

Logan Bartlett is a Managing Director @ Redpoint, a firm with a portfolio including the likes of Stripe, Nubank, Twilio, Netflix, Snowflake and many more incredible names. As for Logan, at Redpoint he has led investments in the likes of Ramp, Monte Carlo, Cribl, Crossbeam and Acuity MD to name a few. Before joining Redpoint, Logan spent over 5 years with the team at Battery where he made investments in Pendo, Amplitude, Dataiku, Braze and Kustomer. In Today's Episode with Logan Bartlett We Discuss: 1.) Entry into Venture: How Logan made his way into the world of venture joining Battery Ventures? What are 1-2 of Logan's biggest takeaways from his time with Battery? What does Logan know now that he wishes he had known when he started in venture? 2.) The Venture Landscape Today: Is now really the best time to be investing? How does Logan compare today to prior vintages? How does this differ when comparing consumer to B2B? How does Logan analyze the state of the growth market? Is anyone really doing deals today? If so, what is the discount on price vs last year? How do the public markets impact the later stage financings which have disappeared in the last 3 months? How do the later stage financings impact the early stage? Does Logan agree that "venture has never been less collaborative as it is today"? 3.) The Role of the Venture Investor: Why does Logan believe that VCs have gotten lazy over the last 2 years? Does Logan believe we will see even more GPs at the top retire in the downturn? How does Logan analyse his role as a board member today? How has his style changed over time? What is the single best board Logan is on? Why that one? Who is the best board member Logan works with? What makes this board member so good? How does Logan assess the importance of personal brand in venture today? Why does Logan believe no company should hire PR firms from the early days? 4.) Investing Style and Lessons: What has been Logan's single biggest hit as an investor? How did seeing that impact his mindset? What has been Logan's biggest miss? How did not doing the investment change how he thinks about making new investments today? How does Logan assess his own relationship to price? How has it changed over time? As a growth investor today, how important is ownership? How does this change with stage? Items Mentioned in Today's Episode: Logan's Favourite Book: Team of Rivals: The Political Genius of Abraham Lincoln Logan's Most Recent Investment: AcuityMD

Whitney Wolfe Herd is the Founder and CEO @ Bumble, changing the way people date, find friends, and the perception of meeting online, for the better. Women make the first move. Over an incredible 6 year journey, Whitney has scaled Bumble to a community of over 100 million across six continents. Bumble has facilitated an incredible 1.8 billion first moves as of 2021 and so many more by now. Prior to founding Bumble, Whitney was the Co-Founder and VP of Marketing @ Tinder. In Todays Episode with Whitney Wolfe Herd We Discuss: 1.) Founding Bumble: How Whitney made her way into the world of startups with her co-founding Tinder? What happened when Whitney left Tinder in a very public way? How did that and the scrutiny that came with it, impact her? How did she change? 2.) CEOship 101: What does "High Performance" mean to Whitney? What are the biggest benefits and biggest downside of transparency? What are the few things that as a leader, you cannot be transparent about them? What does it mean to truly listen as a leader? What are the biggest mistakes leaders make when it comes to listening? 3.) Risk and Pressure in Leadership: What is the single moment of highest pressure Whitney has been through in the Bumble journey? How does Whitney deal with pressure as a leader today? How has that changed? How does Whitney approach risk as a leader today? What is too risky? How does Whitney think through her own decision-making framework? 4.) Whitney: The Mother and Wife What does Whitney believe makes a truly successful marriage? How does Whitney not lose an inch of performance as a public markets CEO and also be an amazing mother to two children under the age of 2? What does Whitney know now that she wishes she had known when she started Bumble? As a leader and mother, what gets easier with time, what gets harder? Items Mentioned in Today's Episode with Whitney: Whitney's Favourite Book: Shantaram

Over the last 7 years, I have scaled 20VC to 100M+ downloads, and listeners in 117 countries, and all of this with a spend of less than $1,000. Here are 10 of my biggest lessons: Lesson 1: Persistence: This is a game of who can last the longest. Lesson 2: Platform Selection: Choose the platform that best aligns to your skills and passion, not the one that is "hottest" at the time. Lesson 3: Just Start: The biggest reason people fail is because they do not take the first step. The V1 will never be perfect but it will improve. Press publish. Lesson 4: Consistency: You have to create a habit within your audience. You have to let them know when they should expect your content. This will also creating a forcing function for you to stick to. Lesson 5: Be Targeted on your Content Topic: Do not be vague. You have to be very specific in the topic you choose. Start very niche. Find your 100 true fans. Expand from there. Lesson 6: Every Piece of Content is Born Multi-Channel: You do a talk. This is not a single talk. This can be turned into a podcast. Several TikToks. A medium piece. No content is in isolation. Lesson 7: The Right Ratio Between Creation and Distribution: Do not create content and then press publish and think the work ends there. You have to spend the same amount of time distributing the content as you do creating it. Lesson 8: Create Champions: In the early days it is all about finding your 100 true fans. DM people that follow you. Make them feel special. They will retain and tell their friends. Create champions. Lesson 9: Bring People Into the Creation Process: When people feel a part of the creation of content, they will share it actively. Make more people feel part of the creation process. Lesson 10: Each Channel is Different, Optimise for Them: Different channels require different content types, formats, audio, optimise on a per channel basis.

Wes Chan is the Co-Founder and Managing Partner at FPV Ventures, a $450M early-stage fund, launched earlier this year. Wes is an investor in five $10B+ "decacorns," his most notable being Canva where he is a member of the board of directors and led the Series A and C rounds. Wes also wrote the first or very early check into Plaid, Flexport, Gusto, Lucid, and RobinHood. Before FPV Wes was a Managing Director at Felicis Ventures and before Felicis Wes founded GV’s seed investing program. If that was not enough, as an operator, Wes co-founded Google Analytics and Google Voice and holds 18 US patents for his work in creating Google AdWords. In Today's Episode with Wes Chan 1.) From Founding Google Analytics to Venture: How did Wes make his way from founding Google Voice and Google Analytics to starting GV's seed investing program? What are 1-2 of the single biggest product takeaways from working closely with Larry and Sergey @ Google? How did Wes make his way from Google to Felicis and scaling the firm with Aydin Senkut? 2.) Market vs Founder: Why Market Sizing is BS: Why does Wes believe that the market always wins over the founder? That said, what does Wes mean when he says "the best founders have 100 year plans?" How does Wes question and analyse 100 year plans? What makes the best? What makes the worst? Why does Wes not do market sizing? Why does Wes not do outcome scenario planning? What does Wes believe is the biggest fallacy of outcome scenario planning? 3.) The Venture Landscape: Does Wes believe that now is really the best time to be investing? Why does Wes believe there are some treacherous deals being done now? What are the signs that these deals are challenging? What advice does Wes give founders fundraising in these markets? What does Wes believe are elements that traditional VCs decide to do, which prevents founders from choosing to work with them? Does Wes believe VCs on board truly provide value? If so, which ones and why them? 4.) FPV: Firm Building and Portfolio Construction: With the new $450M fund, what is the portfolio construction that Wes chose? Why does Wes prefer to have more lines in the portfolio than a concentrated portfolio? Does Wes believe you can increase your ownership in your best companies over time? How does Wes think about capital concentration on a per company basis? What have been Wes' biggest lessons from his biggest hits and misses? Items Mentioned in Todays Episode: Wes' Favourite Book: Liar's Poker

Jordan Van Horn is a Revenue Leader @ Monte Carlo, the world's first data observability company. Prior to this role, Jordan spent an incredible 4 years in sales at Segment including as VP of Sales leading a sales team of 50+ Account Executives and leading the first international expansion for the company into Dublin. Before Segment, Jordan was at Dropbox for 4 years leading enterprise sales for Dropbox Business in California. In Today's Episode with Jordan Van Horn We Discuss: 1.) Entry into the World of Sales: How did Jordan make his way into the world of sales first with a vineyard? What are 1-2 of the biggest takeaways for Jordan from seeing the scaling sales teams at both Segment and Dropbox? How did seeing that impact his mindset? What does Jordan know now that he wishes he had known when he entered sales? 2.) The Sales Playbook: How does Jordan define "the sales playbook"? What is it not? What five core things should the sales playbook help you accomplish? Should the founder be responsible for the sales playbook? Can it be created by a Head of Sales? How does Jordan advise founders on three signals that now is the right time to bring in a sales hire? How does Jordan advise founders on whether the first sales hire should be a rep or a leader? 3.) The Secrets to Pricing and Discounting: Why does Jordan not care what price customers pay in the early days? If it is not about ARR, what should teams be optimizing for? When does price discipline become important in a company journey? What are the dangers of not having price discipline? What two tools do sales leaders have to use in order to create urgency in a deal closing process? How should sales leaders think about building multiple champions within a potential customer? At what price point is it worth it? 4.) The Hiring Process: How does Jordan structure the hiring process for all new sales hires? What are the must-ask questions that Jordan asks all new candidates? What does he want to see in those answers? Who else does he bring into the hiring process? At what stage do they get involved? What are they testing for? Does Jordan use case studies with candidates? What makes the best? What makes the worst? 5.) The Onboarding: What is the ideal onboarding process for new sales reps? What should founders do and prep for when onboarding their first sales hires? What materials and recordings should they have ready? What are some early signs that a new hire is not working out? How do we measure their impact? For enterprise sales, it takes a long time to close new deals, how can one determine effectiveness of new reps when the sales cycle is so long?

Sheel Mohnot is a Co-Founder and General Partner @ Better Tomorrow Ventures, a $225M fund that leads rounds in pre-seed and seed-stage fintech companies globally. Sheel and Jake (his co-founder) invested for many years together before founding BTV and wrote checks into Mercury, Flexport, Ramp, and Hippo Insurance to name a few. As for Sheel, before BTV he ran 500 Fintech for close to 7 years, and before that was a founder, founding two companies, both of which were acquired. If that was not enough, Sheel is also a master at measuring the width of swimming pools and making cameo appearances in music videos with Justin Bieber. In Todays Episode with Sheel Mohnot We Discuss: 1.) Entry into Venture: How Sheel made his way into the world of venture having founded 2 fintech companies? Why did no LPs give Sheel money in the early 500 Fintech days? What were some of his biggest lessons from investing in 100s of companies with 500 Fintech? How did BTV with Jake come together most recently? What are the biggest differences to Sheel of being a fund manager vs being an investor? 2.) The Power Law: How does Sheel define "the power law" in venture capital? What multiple of return would be power law status? Given the size of outcome available with these power law returns, how does Sheel approach portfolio construction? Would it not be best to invest in 100s of companies? Who does Sheel believe has done the indexing approach best? Why? 3.) Venture Capital has Never Been Less Collaborative: Why does Sheel disagree with Harry that venture capital has never been less collaborative? Why now, for the first time, are large multi-stage funds taking single-digit ownership? Does Sheel agree with Harry it is moronic to have "guaranteed pro-rata"? How does Sheel approach re-investment decision-making? When does he pay up vs not? 4.) The Biggest Wins and Misses: What have been Sheel's biggest wins from a cashback and a multiple perspective? How did Sheel miss the chance to invest in both Robinhood and Chime early on? What did he not see? How would he have thought differently with the benefit of hindsight? How have Sheel's biggest hits and misses impacted how he invests today? 5.) Emerging and Frontier Markets: Does Sheel share Harry's concern for the removal of capital from emerging markets? Why does Sheel believe that India, South East Asia and LATAM will be fine? Why does Sheel believe Pakistan and Africa are most in trouble? What advice does Sheel give to his emerging markets founders today? Items Mentioned in Today's Episode: Sheel's Favourite Book: Enders Game

Marcelo Claure is an entrepreneur and investor who has founded and led some of the world’s most iconic businesses. He is currently the Chairman & CEO of Claure Capital, a newly founded multi-billion-dollar global investment firm. Before this, Marcelo was COO @ Softbank Group, the world’s largest technology investment company. Bill Gurley is a General Partner @ Benchmark, one of the most successful funds of the last decade with a portfolio including Uber, Twitter, Dropbox, Modern Treasury, Snapchat, StitchFix, and many more. Michael Eisenberg spent 15 years as a General Partner @ Benchmark working alongside Bill and the Benchmark partnership. Following Benchmark, Michael co-founded Aleph, one of the leading Israeli venture funds of the last decade. David Tisch is the Founder and Managing Partner @ Box Group, one of the leading seed focused firms of the last decade with a portfolio including Airtable, Glossier, PillPack, Plaid and many more. Cyan Banister is one of the most successful and renowned early-stage investors in the last decade. Her portfolio includes the likes of SpaceX, Uber, Affirm, Opendoor Postmates, Niantic and Thumbtack to name a few. Zach Weinberg is a Co-Founder of Operator Partners, operators funding operators, with no outside LPs, just their own capital. Luciana Lixandru is a Partner @ Sequoia, one of the world’s most renowned and successful venture firms with Sequoia-backed companies accounting for more than 20% of NASDAQ’s total value. Jeff Lieberman is the Managing Director @ Insight Partners, one of the leading investing franchises of the last 25 years with their most recent flagship fund announced earlier this year being a staggering $20BN. Nick Shalek is a General Partner @ Ribbit Capital, specializing in fintech they are one of the most successful venture firms of the last decade with a portfolio including Robinhood, Coinbase, Revolut, Nubank and more. Frank Rotman is a founding partner of QED Investors, one of the leading fintech-focused venture firms investing today with a portfolio including the likes of Klarna, Kavak, Quinto Andar, Credit Karma and more. Geoff Lewis is the Founder and Managing Partner @ Bedrock, now with over $1BN in AUM, Bedrock invests in breakout technology companies that are incongruent with popular narratives. Justin Fishner-Wolfson is founder and the managing partner of 137 Ventures. Their portfolio includes SpaceX, Wish, Anduril, Flexport, and WorkRise (formerly Rigup) to name a few. David Sze is a General Partner @ Greylock where he has led some of the firms most notable investments including Facebook, LinkedIn and Pandora. In Today's Episode We Discuss Price Sensitivity: 1.) How do you assess your relationship to price and price sensitivity? 2.) When is the time to pay up and have less price discipline? 3.) When should we remain disciplined and not pay up for a deal and walk away because of price? 4.) Of the deals you have paid up for, did their growth rate justify the high entry price? 5.) Knowing all you know now on price, how do you advise younger investors today?

Kieran Flanagan is SVP Marketing at HubSpot, where he has helped the business grow internationally, move to a product-led business, quadrupled its marketing demand, and built out its media team, including the acquisition of 'The Hustle.' He is also an advisor and investor in early-stage companies. In Today's Episode with Kieran Flanagan We Discuss: 1.) Entry into Growth and Marketing: How did Kieran make his way into the world of growth and marketing? What has been 1-2 of Kieran's biggest lessons from seeing firsthand the hyper-scaling of Hubspot? On reflection, how would Kieran summarise both Hubspot's community building attempts and also their product messaging? 2.) Why You Need Growth Hires Pre Product Market Fit: What does "growth" mean to Kieran? Where do so many get it wrong? Why does Kieran believe that you should have a growth team/people before product market fit? What specifically do they do and work on during this stage? Pre PMF, what is the core metric that all startups should focus on? How does it change with time? 3.) Building Your Growth Team: What does Kieran believe are the 3 key stages to hiring for growth? How should founders determine whether to have external standalone growth teams or integrate them into existing functions? What are the single biggest mistakes founders make when hiring for growth? 4.) The Future is Content: Why does Kieran believe every great tech brand will have to become a media brand? Why is Elon Musk an example of the perfect brand? What has he done right? Why does Kieran say that data is the best and worst thing that has happened to marketing? 5.) WTF Really is Community: How does Kieran define "community"? What is it? What is it not? What makes the best communities? Why do some work and others not? Should every company have a community approach? Who does it make sense for? Have Hubspot done a good job at community building? On reflection, is there anything that Kieran would have done differently?

Mo Koyfman is the Founder and General Partner @ Shine Capital, who announced earlier this year Shine II, a $200M early-stage fund, and Shine Opportunities I, a $100M vehicle. Prior to founding Shine, Mo was the Managing Member @ Moko Brands where he made angel investments in Coinbase, Polychain, Harry's to name a few. Before Moko, Mo spent over 7 years as a General Partner @ Spark Capital where he made investments in Plaid, Warby Parker, Skillshare and Hivemapper, to name a few. Finally prior to Spark, Mo spent over 5 years at IAC where he oversaw group of companies that included Connected Ventures, parent of Vimeo, CollegeHumor & BustedTees. In Today's Episode with Mo Koyfman: 1.) From Entrepreneurial Parents to IAC, Spark Capital and Founding Shine: How did Mo make his way into the world of venture having worked with Dara Khros, Barry Diller and Jeremy Liew? What were some of the biggest takeaways from his time with Barry Diller and IAC? How did Mo's time at Spark impact his investing mindset? What did he learn that he took with him to founding Shine? 2.) Investment Firm vs Investment Partnership: What are the biggest differences between investment firms and investment partnerships? What are the biggest risks founders are taking when they take money from investment firms? Mo has very strong beliefs, how does he manage and inspire debates within his firm without shutting down or intimidating younger, less experienced team members? What does Mo mean when he says, "firms are great but partners matter". 3.) How To Win in Venture: Why does Mo always believe that small funds outperform large funds? What have been some of Mo's biggest lessons from Fred Wilson on fund strategy and sizing? How much of an emphasis does Mo place on the importance of ownership? Why does Mo believe the way to win in venture is to be collaborative? Why does Mo believe in the macro conditions we are entering, the landscape is about to become a lot more collaborative? Why does Mo believe any firm that says they will always do their pro rata is lying? 4.) The Lessons: Success and Failure: What are some of Mo's biggest lessons from his biggest wins, like Plaid at seed? That said, why does Mo believe it is so dangerous to try and learn lessons from the wins? What failures have been most impactful to Mo? What did he take away from them? Why does Mo believe that making great burgers is like building great companies? Items Mentioned in Today's Episode: Mo's Favourite Book: Portnoy's Complaint by Philip Roth

Sameer Shariff is the Co-Founder and CEO @ Cambly, the company that allows you to become fluent faster through one-on-one video chat lessons with native English tutors. To date, Sameer has raised over $60M with Cambly from the best including Jeremy Levine @ Bessemer, Sarah Tavel @ Benchmark, Monashees, YC and more. Prior to founding Cambly, Sameer spent close to 5 years at Google on the Search Quality team and became the Tech Lead of the Search experiments team helping make experimentation a core part of the launch process. In Today's Episode with Sameer Sharif We Discuss: 1.) Entry into Startups and Co-Founding Cambly: How did Sameer make his way into the world of tech with his joining Google straight out of college? What were the 1-2 biggest takeaways from his time at Google? How did it shape his mindset? What was the a-ha moment for Sameer with Cambly? 2.) The Trials and Tribulations of Leadership: What does "high performance" mean to Sameer in business? How has it changed over time? What are the first things to break in a scaling company? How do the best companies retain speed and agility with scale? What are the single biggest hiring mistakes Sameer has made? What did he learn? 3.) The Fundraise that Led to Cash Flow Positive: Why does Sameer think it was so hard to fundraise for Cambly in the early days? When they failed to raise their Series A, what 3-4 core decisions did they make to get Cambly to cash flow positive as fast as possible? How did Sameer communicate their failed fundraising to the team? How did he do this in a way that rallied the troops and did not worry or scare them? What was the tipping point for fundraising to become much much easier for the company? Given they have not touched any of their Series A or Series B funds, how does Sameer think about the balance of growth vs profitability? 4.) Marketplace Dynamics 101: How did Cambly acquire the first 100 customers on the demand side? What is the most challenging dynamic of Cambly; demand or supply side? Where does Sameer see most marketplace founders make the biggest mistakes? What does Sameer know now on the intricacies of marketplace dynamics that he wishes he had known at the beginning? Items Mentioned In Today's Episode with Sameer Shariff: Sameer's Favourite Book: The Most Human Human: What Artificial Intelligence Teaches Us about Being Alive

Shreyas Doshi is an investor, advisor, and all-around product OG. Most recently Shreyas spent over 5 years at Stripe where he was Stripe's first PM Manager and helped define and grow the Product Management function (from ~5 to more than 50 people). Before Stripe, Shreyas was a Director of Product Management @ Twitter and prior to Twitter spent over 6 years as a Group Product Manager @ Google. Today Shreyas has invested and advises some of the best including advising Airtable, Kalshi, Lendflow, to name a few. In Today's Episode with Shreyas Doshi: 1.) Entry into Product: How did Shreyas make his way into the world of product and product management? Why did Shreyas decide not to do business school when it was the conventional route for everyone going into product management? What were some of Shreyas' biggest takeaways from his time at Stripe and Google? How did they impact his product mind today? 2.) Product Management 101: How does Shreyas define product management today? How do many confuse it? How does Shreyas define product success today? What is the single biggest mistake Shreyas sees founders make when determining the success/PMF of their product? Does Shreyas believe that great product management is science or art? Data or intuition? When should you listen to customers? When should you not? 3.) Metrics 101 & How To Use Them: What is the single biggest mistake Shreyas sees founders make when it comes to selecting their North Star metric? How should founders think about input vs output metrics? What is the difference between the two? What are the 6 types of metrics that all founders and product teams need to focus on? How does their importance change over time? How should the responsibility for these metrics be split between different people and teams? 4.) Three Types of Product Leader: What are the three different types of product leaders? The Craftsperson: What is their core strength? What is their core weakness? How do they interact with the rest of the team and company? The Operator: What is their core strength? What is their core weakness? How do they interact with the rest of the team and company? The Visionary: What is their core strength? What is their core weakness? How do they interact with the rest of the team and company?

Kirsten Green is the Founder and Managing Partner @ Forerunner Ventures, one of the leading firms of the last decade investing at the intersection of innovation and culture. As a founder, Kirsten has led efforts to raise over $2B+ from leading institutional investors and invest in more than 100 companies. She currently serves as a board member at Glossier, Ritual, Faire, Hims & Hers, and Curated, to name a few. She has also invested in other smash hits including Chime, Jet, Warby Parker, Hotel Tonight and many more. Due to her immense success, Kirsten has been honored in Time’s 100 Most Influential People and named a Top 20 Venture Capitalists by The New York Times in 2018 & 2017. Prior to Forerunner, Kirsten was an equity research analyst and investor at Banc of America Securities. In Today's Episode with Kirsten Green We Discuss: 1.) Entry in Venture at 40 and Founding Forerunner: How did Kirsten make her way into VC at 40 with the founding of Forerunner having never had a role in VC before? What did everyone tell Kirsten when she was looking to break into venture? What did she tell herself when she heard this? What does Kirsten believe she is running from? What does she believe she is running toward? 2.) Fund Management and Leadership: How does Kirsten define high-performance today? What are the nuances of high performance in fund management? How would Kirsten describe her leadership style today? How has it changed over time? What have been some of Kirsten's biggest lessons in terms of what it takes to retain quality with scaling AUM and teams? What have been Kirsten's biggest lessons when it comes to giving hard feedback with kindness? 3.) The Venture Landscape Today and Forerunner's Position: Why does Kirsten believe the venture landscape is more dynamic today than ever? Does Kirsten agree with the statement that venture is less collaborative than ever? Why did Kirsten and Forerunner seem to amend strategy and move into B2B? Why does Kirsten disagree with the delineation between B2C and B2B? 4.) Parenting, Relationships and Life: What have been Kirsten's biggest lessons since becoming a parent? How has it impacted her mindset? Does Kirsten agree that relationships attract from sheer input on work? How does Kirsten separate relationships into two kinds of relationships? What does success in marriage mean for Kirsten? How has she seen that in her own marriage?

Jim Lanzone is the CEO @ Yahoo, a company that today reaches nearly 900 million people around the world and is the third largest property on the Internet. Prior to Yahoo, Tim was the CEO of Tinder, the world’s most popular app for meeting new people, downloaded by more than 400 million people. Before Tinder, Jim spent a decade as President and CEO of CBS Interactive, a top 10 global Internet company with brands ranging from CBS All Access to CNET. He joined CBS Interactive in 2011 when CBS Corporation purchased Clicker Media, where he was founder and CEO. Before founding Clicker, Jim served as CEO of Ask.com (formerly Ask Jeeves). In Today's Episode with Jim Lanzone 1.) Jim's Entry into the World of Startups: How did Jim go from law school to founding his first tech startup in the dot com boom? How did seeing the crash and the first company going bust, shape Jim's perspectives on great leadership? What does Jim know now that he wishes he had known when he started way back in 1999? 2.) Leadership 101: How does Jim define "high performance" in business today? What are the 4 things Jim always looks for when hiring new people? Why does Jim believe the standard interview process and questions are broken? How does he do it differently? What are his biggest lessons on how to hire effectively? How does Jim know when to let someone go? How long do you give under-performers? 3.) Crashes and Turnarounds: Jim has seen three crashes as a CEO, what are Jim's biggest lessons from 3 prior crashes? How does Jim advise founders to be acting today? What should they focus on? How can leaders maintain morale and optimism in the face of tough macro times? How does Jim advise founders to communicate both with their investors and board when it comes to reduced performance in harder times? 4.) The Yahoo Turnaround: What does Jim believe the 1-2 core things Yahoo needs to fix is? Why are they priorities? How does Jim approach turning round the Yahoo brand? How does he plan to make it attractive? What is the biggest misnomer that people have about Yahoo today? How does Jim think about running a portfolio approach with Yahoo moving forward? How has Jim changed the org structure and management of Yahoo most significantly? Items Mentioned in Today's Episode: Jim's Favourite Book: Team of Rivals: The Political Genius of Abraham Lincoln

Today we deconstruct the canonical question in early-stage sales. Does the founder need to create the sales playbook? Then secondly, if not, should the first sales hires be reps or a sales leader? Today we are joined by 7 of the best sales leaders to share their thoughts. Jordan Van Horn is a Revenue Leader @ Montecarlo. Previously Jordan spent 4 years with Segment and before that spent another 4 years at Dropbox. Oliver Jay (OJ) most recently spent 6 years at Asana where he was hired as the company’s first revenue leader. Before Asana, OJ spent 4 years at Dropbox where he scaled the sales team from 0 to 50 while tripling ARR. Dannie Herzberg is a Partner @ Sequoia Capital and previously spent 4 years at Slack as their Head of Enterprise Sales. Before Slack, Dannie spent 5 years at Hubspot building sales, opening an SF office, and then joining product to launch CRM & platform. Zhenya Loginov is the CRO @ Miro, where he runs the go-to-market team of 700+ people across 11 global offices. Prior to Miro, Zhenya was the COO @ Segment. Finally, before Segment, Zhenya led a 100-person team at Dropbox across numerous different functional areas. Kyle Parrish is VP Sales @ Figma, where he has scaled the sales team from 0 to over 100 people in sales. Before Figma, Kyle spent over 5 years at Dropbox in numerous different roles including Head of Sales, where he scaled the Austin, Texas office from 3 to over 80 people. Sam Taylor is the VP of Sales and Customer Success @ Loom, at Loom Sam leads Revenue Org including: Direct Sales, Customer Success, Self-Serve Revenue Growth/Assist. Prior to Loom, Sam spent over 4 years at Salesforce, following their acquisition of Quip, where he was the first sales leader. Before Salesforce and Quip, Sam spent over 3 years at Dropbox as a mid-market sales leader. Jeanne DeWitt Grosser is Head of Americas Revenue & Growth @ Stripe. Pre-Stripe, Jeanne was CRO @ Dialpad and also spent many years at Google in numerous different roles including most recently as Director of GSuite SMB & Mid-Market Sales, North America and LATAM. Mitch Tarica is Head of North America Sales at Zoom Video Communications. Before Zoom, Mitch spent over 5 years at RingCentral and before RingCentral, Mitch was at Oracle for over 7 years in numerous different sales roles. In Today's Discussion on Sales Playbooks We Learn: 1.) What is the right definition for a "sales playbook"? 2.) When is the right time to change your "sales playbook"? 3.) What are the biggest mistakes or misnomers made around the "sales playbook"? 4.) Should the founder be the one to create the first sales playbook or can it be a sales leader? 5.) When is the right time for founders to hire their first sales leaders? 6.) For the first sales hire, should founders hire sales reps or a sales leader? 7.) When should you hire a rep vs a sales leader? What are the nuances?

Tony Fadell, often referred to as the father of the iPod is one of the leading product thinkers of the last 30 years as one of the makers of some of the most revolutionary products in society from the iPhone and iPod to more recently founding Nest, creating the Nest Thermostat, leading to their $3.2BN acquisition by Google. Tony recently released Build, a masterclass taking 30 years of product and company building lessons and packaging them for you, check it out here. In Today's Episode with Tony Fadell: New York Times' 36 Questions of Love 1.) On reflection, what would Tony most like to change about his childhood? How did moving so much as a child change who Tony was as a person? How can parents instill that same grit and desire in their kids today? What does Tony think is the biggest problem with modern parenting? 2.) As a leader, should the company you are building be a family or a team? What does Tony believe are the 3 hats of being a great CEO? What is the biggest challenge in the transition between hats? Where does Tony see many founders make the biggest mistake? Which hat was Tony strongest with? What was he weakest with? 3.) How to solve the loneliness of being a solo founder? Why does Tony believe that everyone needs a co-founder? Why does Tony not like to invest in teams with a solo founder or more than 4 founders? For Tony, what is the ideal composition of that founding team? How does he test for these skills and traits pre-investing? 4.) How to think differently in the face of adversity? Tony has made bold bets when everyone says he is crazy, how does he not question himself and remain strong in the face of criticism? How does Tony know when to change his mind? When to accept that the bold idea was not right? Is Tony concerned in the face of macro challenges today, investment and commitment to climate change will be cut heavily?

Kyle Samani is the Co-Founder and Managing Partner @ Multicoin Capital, one of the leading crypto native funds of the last decade with positions in Solana, FTX, Fractal, and Helium to name a few. As for Kyle, before moving to the world of venture and crypto, he founded Pristine, a health IT startup that raised more than $5M in VC, and was acquired by Upskill. In Today's Episode With Kyle Samani We Discuss: 1.) The Founding of Multicoin Capital: How did Kyle make his way from a healthcare startup to founding Multicoin? What was his a-ha moment with the realization of the opportunity we have ahead of us in crypto? What does Kyle know now that he wishes he had known when he started Multicoin? 2.) Crypto Investing in 2022: Why does Kyle believe the crypt investing landscape is less collaborative than ever? What are the biggest challenges of token issuances today? How does the option of liquidity help and hurt Kyle's investor psychology? Is Kyle concerned the volatility in the market will harm institutional investor sentiment for crypto? 3.) Constructing a Crypto Portfolio in 2022: Why does Kyle not believe in temporal diversification? Why does sector-centric company diversification suck? Why are the loss ratios in crypto so much lower than in traditional venture? Why does Kyle believe a no reserves model is optimal in crypto? 4.) Multicoin vs Traditional Venture Firms: Why does Kyle believe that every person over 10 people in a venture firm is a net negative towards the investment decision-making process? What do Kyle and Multicoin do reach the truth together? How do they aggressively use writing and word docs to progress their thoughts? Their discussions are "brutal", how brutal can one be in a discussion on a deal? How does one make team members feel safe but also really push them for the truth and debate? Item's Mentioned in Today's Episode: Kyle's Favourite Recent Reading: Eugene Wei Kyle's Most Recent Investment: Delphia

Sam Taylor is the VP of Sales and Customer Success @ Loom, an essential tool for hybrid and remote teams allowing you to record quick videos of your screen and cam. At Loom Sam leads Revenue Org including: Direct Sales, Customer Success, Self-Serve Revenue Growth/Assist, Sales Development, Global Customer Support, Revenue Ops + Strategy and Sales Enablement. Prior to Loom, Sam spent over 4 years at Salesforce, following their acquisition of Quip, where he was the first sales leader. Before Salesforce and Quip, Sam spent over 3 years at Dropbox as a mid-market sales leader. In Today's Episode We Discuss: 1.) Entry into the World of Sales: How did Sam land his first big role in sales at Salesforce? How did the sales orgs differ when comparing Salesforce to Dropbox? What are 1-2 of Sam's biggest lessons from his time at Salesforce and Dropbox that shapes how he thinks today? 2.) Sales People Should Be Customer Therapists: What is the right way to approach customer discovery? How can sales reps get potential customers on a call in the first place? What are the right questions to ask? What engenders the most honesty? What are the wrong questions to ask? What are common mistakes? How do the best sales reps then feed that back to customer success and product? 3.) The When and The Who: When should founders consider hiring their first sales hire? Should this hire be a sales leader or a sales rep? What are the nuances? What are the characteristics of the best first sales hires? What are the first sales hires really on the hook for? Why does Sam disagree with the word "playbook" and instead suggest "frameworks"? 4.) How To Hire The Best: The Process What are Sam's lessons on what it takes to hire the very best sales reps? What are the right questions to ask in the interview process? What tangible case studies or tests are done to measure quality? Who is brought into the hiring process and at what stage?

Des Traynor is a Co-founder and the Chief Strategy Officer of Intercom, the modern customer communications platform that unifies every aspect of the customer journey. To date, Intercom has raised over $238M from some of the best including Index, ICONIQ, Kleiner, GV, and Bessemer. As for Des, before co-founding Intercom, he was a UX consultant, a university lecturer in computer science, and also a Ph.D. researcher. Des is also a prolific angel investor with a portfolio including the likes of Stripe, Algolia, Notion, Miro, and many more. In Today's Episode We Discuss: 1.) Origins of Intercom: How did Des make his way into the world of startups and come to co-found Intercom? When did they realize they really had something with Intercom and had to focus on it? What does Des know now that he wishes he had known at the start of Intercom? 2. Two of the Biggest Myths in Startups: Being First and Defensibility Why does Des believe that being the first does not matter? Why is it not an advantage? Why does Des believe that no company has defensibility on day 1? How does Des believe defensibility is built? What does Des mean when he says, when investing in companies he looks for a "long road to the starting line"? 3.) Product 101: A Masterclass on Product: How does Des answer the question of when to release a second product? How should the second product be resourced? MVP and lean or full budget and committed? What are the biggest mistakes people make when releasing a second product? What mistakes have Des and Intercom made when releasing new products? How does Des advise founders on when to stop working on a product? How do you know when it is not working? How does Des determine between a feature and a product both when building and when investing? 4.) Moving to Enterprise: What does Des believe are the three core things all companies need to scale into the enterprise effectively? Which should they do first? Which is most challenging? How does Des advise founders on when is the right time to move into the enterprise? How does the product need to change to meet enterprise needs and requirements? 5.) The Makings of Great Product Marketing: What does Des believe makes truly great product marketing? Who does it well today? How does your product marketing need to change as you scale from SMB to enterprise? If product marketing to both an end user and a separate buyer, which persona should one prioritise their messaging towards? How does Des advise founders on product marketing when they have a horizontal product with a very broad customer base? 6.) Angel Investing 101: From Stripe to Miro to Notion: Why does Des believe it is beneficial for operators to also be investing? What are the biggest lessons Des has learned from angel investing? How does Des approach both market sizing and outcome scenario planning today? How price sensitive is Des today? How has that changed over time? Item's Mentioned in Today's Episode with Des Traynor: Des' Favourite Book: How Will You Measure Your Life by Clayton Christensen

Peter Singlehurst is the Head of Private Companies at Baillie Gifford. As of 31st March 2022, funds under Baillie Gifford's management and advice totaled £277bn. The firm is owned and run by 51 of its senior executives who operate as a partnership, a structure that has endured for over a century. As for Peter, he has been with Baillie Gifford since graduating from Durham University 12 years ago and has backed some astonishing breakouts such as Wise, Grammarly and Zymergen to name a few. In Today's Episode with Peter Singlehurst We Discuss: 1.) Entry into Venture: How Peter landed his role with Baillie Gifford straight out of university? Why does Peter and Baillie Gifford prefer to hire young people without backgrounds or studies in finance? Why do they tend to be better investors? What does Peter believe are the basic building blocks that can be taught in investing? What cannot be taught and needs to be learned with experience and time? 2.) The Biggest Misnomers and Misalignments in Venture: Why does Peter believe the distinction between public vs private markets is BS? Why does Peter believe it is an advantage to invest at the same time in both public and private markets? Why does Peter think there is an inherent misalignment in venture between GPs and their LPs? 3.) Baillie Gifford: Constructing a Portfolio with £277BN: How does Baillie Gifford approach portfolio construction today? How many lines do they want to have in their portfolio? What is the right level of diversification? How does Peter think about sizing each position? How does Peter think about capital concentration across rounds vs first check being the largest? How does Peter approach outcome scenario planning? How does Peter think about downside protection and loss rates? 4.) Peter Singlehurst: The Investor: How has Peter's investing style changed over the last 10 years? What has gotten easier? What has gotten harder? What is Peter's biggest miss? How did it change his approach? What is Peter's biggest hit? What did he learn and take from this? How did the crossover funds change and impact the way that later stage venture was conducted? Item's Mentioned In Today's Episode: Peter's Fave Book: The Myth of Sisyphus Peter's Most Recent Investment: Grammarly

Luc Levesque is currently the VP of Growth at Shopify and also advises companies like Twitter, Pinterest, and Quora. At the age of 21, Luc founded TravelPod, the world’s first travel blogging platform. 10 years later, TravelPod was acquired by Expedia, where Luc led the creation of two award-winning products: TripWow and the Traveler IQ Challenge. Luc then served as an executive at TripAdvisor, where he built and led the growth team which helped TripAdvisor become the world’s largest travel site. Luc was then recruited by Mark Zuckerberg to Facebook where he was an executive and led the creation of Messenger Kids. In Today's Episode with Luc Levesque We Discuss: 1.) Entry into Growth: When did Luc realise the power of "growth" within every company? How did Luc subsequently make his way into the world of growth pose-selling his first company? What does Luc know now that he wishes he had known when he made the entry into growth? 2.) Growth and Viral Loops: How does Luc define "growth" today? How should leaders choose what is the right north star to focus on for their business? Should this north star change? If so, how often should the north star change? How does Luc define "viral loops"? What makes the best viral loops today? 3.) Growth: Building the Team: When is the right time for founders to start thinking about building a growth team? Should it be standalone or integrated into other functions in the company? Should the first growth hires be senior and tasked with hiring the team or junior and be more lean as a way to test growth as a new function? What are the signals Luc looks for when hiring for growth? What are the best questions that reveal the characteristics growth leaders need to have? 4.) Growth: The Action: What is a growth decision Luc made without data? How did it go? What are some growth tactics that have become stronger over time? What have died a death? How should leaders know when to kill a new project vs continue and keep testing? What are the biggest mistakes Luc sees founders make when building and scaling their growth team?

Matt Mullenweg is the Founder of Automattic, the force behind WordPress, Tumblr, WooCommerce, Jetpack, Longreads, Simplenote, Pocket Casts, and more. What started as a simple open-source blogging platform, Matt has turned into one of the most significant internet properties of our generation, now powering over 43% of sites on the internet. Alongside Automattic, Matt also invests through Audrey Capital and has backed the likes of Stripe, SpaceX, Gitlab, and Sendgrid to name a few. In Today's Episode with Matt Mullenweg We Discuss: 1.) The Origins of WordPress: How did Matt start the for-profit, Automattic, as a 19-year-old, having been a lead developer for WordPress? What were the clearest signs to Matt in the early days that WordPress could change the world? What does Matt know now that he wishes he had known at the beginning of WordPress? 2.) Matt Mullenweg: The Essence of Leadership: What does high performance mean to Matt? How has that changed over time? What does truly great listening mean to Matt as a leader today? Where do many get this wrong? How does Matt approach decision-making today? What are the two types of decisions? What are Matt's biggest insecurities in leadership today? How have they changed over time? 3.) Matt Mullenweg: The Person: Why does Matt have insecurities around his body? How do those insecurities manifest? What did Matt learn about himself in the pre-grieving process before his father's passing? How does Matt assess his own relationship to risk today? How does Matt think through his relationship to money today? Has it changed? 4.) WordPress: The Company: Why did Matt decide it was the right decision to buy Tumblr? Why did Matt make himself the CEO earlier this year? With many strong cashflow businesses within Automattic, how does Matt think through the balance between growth and profitability? Why does Automattic not have any emails within the company? How do 2,000 people communicate so effectively? Items Mentioned in Today's Episode: Matt's Favourite Book: Principles by Ray Dalio

Mike Chalfen is a solo GP with Chalfen Ventures and one of the most respected and successful early-stage investors in Europe over the last two decades. Among Mike's incredible portfolio includes the likes of King.com (makers of Candy Crush), Houzz, Tipalti, Snyk, and Tray.io, to name a few. Some incredible facts on Mike, he has a 15x career track record, he has a portfolio value of over $40BN+ and he joined the venture industry, the year of my birth! In Today's Episode with Mike Chalfen You Will Learn: 1.) Entry Into Venture and The Broken Customer Experience of VC: How did Mike make his original entry into venture way back in 1996? What does Mike mean when he speaks of the difference between "managing your career vs the money you invest"? What does Mike believe are some of the greatest challenges of venture partnerships today? What does Mike believe that the customer experience in venture partnerships for founders is broken today? How did seeing the prior booms and busts impact Mike's investing mentality today? 3.) Portfolio Construction 101: How does Mike think about portfolio construction today? With 9-10 core positions, why does Mike disagree with the traditional notion of "diversification"? How does the decision-making framework for Mike change when considering new investments vs re-investments? Does Mike believe that pro-rata is a lazy notion? What does Mike need to see on the upside to re-invest? How does Mike feel about the importance of temporal diversification? Why did Mike increase the cadence of his investing in 2021? Does he regret the increased speed? 3.) The Market 101: How does Mike think about the importance of market sizing? If we always underestimate the size of our winners, is this market sizing exercise not destined for failure? Why does Mike believe so many over the last few years have poorly sized markets they invested in? How does Mike assess market timing risk? What market risk is he willing vs not willing to take? What have been some of Mike's biggest mistakes when analyzing markets in the past? How did it change his perspective? 4.) Boards 101: How would Mike describe his style of board membership today? How has it changed over time? Why does Mike believe that boards at seed are not valuable? When do they become valuable? What is the single biggest mistake Mike sees so many young board members make today? What is his biggest advice to young board members? How does Mike advise founders on preparing for boards? What does he want to see? What are the biggest mistakes founders make when conducting board meetings? Items Mentioned in Today's Episode with Mike Chalfen: Mike's Favourite Books: Don't Let's Go to the Dogs Tonight: An African Childhood, Days Without End Mike's Most Recent Investment: Opply

Scott Belsky is an entrepreneur, master of product reviews, author, investor, and currently serves as Adobe’s Chief Product Officer and Executive Vice President, Creative Cloud. Tony Fadell, often referred to as the father of the iPod is one of the leading product thinkers of the last 30 years as one of the makers of some of the most game-changing products in society from the iPhone and iPod to more recently founding Nest. Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. Kayvon Beykpour is one of the most prominent product leaders of the last decade. For the last 7 years, Kayvon has been at Twitter where he led all of the teams across Product, Engineering, Design, Research and Customer Service & Operations. Aparna Chennapragada is Chief Product Officer @ Robinhood, the company revolutionising consumer finance with commission-free investing. In Today's Episode Breaking Down Product Reviews We Discuss: 1.) What makes a truly great product review? 2.) What are the biggest mistakes that product leaders make when leading product reviews? 3.) Who should be invited to the product review? How does this change with scale? How does this change in a world of remote work and Zoom? 4.) Who should set the agenda for the product review? 5.) How can leaders assign accountability and ensure that the follow-ups from product reviews are executed on? 6.) How can leaders ensure that they do not dominate product reviews with the weight of their words? How can they give designers and devs the space to share their thoughts without being judged?

Daniel Yanisse is the co-founder and CEO of Checkr, a leading HR technology company, currently valued at $5 billion. During the journey, Daniel has raised over $679M for Checkr from some of the best including Accel, Bond, Coatue, GV, Elad Gil and IVP to name a few. Prior to Checkr, Daniel was a software engineer and helped develop prototypes of the Mars Rover for NASA. Daniel has been recognized in Forbes “30 Under 30” and recently Checkr was recognized by Forbes as one of America’s best start-up employers. In Today’s Episode with Daniel Yanisse You Will Learn: 1.) The Origins of Checkr: The $5BN Company How did Daniel come to co-found Checkr? What was the a-ha moment? How did Daniel's experience with his prior company impact how he thought about building Checkr? What does Daniel know now that he wishes all first-time founders knew when they started? 2.) Hiring 101: What are the single biggest hiring mistakes Daniel made in the early days of Checkr? How does Daniel structure his interview process for new candidates today? How has it changed? How does Daniel test for ego and humility in the interview process? How does Daniel approach giving feedback today? How has it changed over time? What does Daniel believe is the right way to let someone go? How long does one give a team member who is not performing? 3.) Fundraising 101: How does Daniel advise founders going out to raise today in the challenging market conditions? What terms should founders optimize for? What terms should they not optimize for? What are the single biggest mistakes Daniel sees founders make when raising? What does Daniel wish he had done differently with Checkr's raises? What was the hardest raise for Checkr? Why was it so hard? What was the outcome? 4.) Going into Enterprise: Why does Daniel believe they went into enterprise too soon? What was the result of this? How does Daniel advise founders on when is the right time to go into enterprise? What changes in both your company and your product when moving to enterprise? Items Mentioned in Today’s Episode with Daniel Yanisse: Daniel’s Favourite Book: Accelerate: The Science of Lean Software and Devops: Building and Scaling High Performing Technology Organizations

Bill Gurley is a General Partner @ Benchmark Capital, Bill, is widely recognized as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix, and Zillow. Doug Leone is the Global Managing Partner @ Sequoia Capital, one of the world’s most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom and many more. Keith Rabois is a General Partner @ Founders Fund, one of the best performing funds of the last decade with a portfolio including Facebook, Airbnb, SpaceX, Stripe, Anduril, the list goes on.  Arthur Patterson and Jim Swartz founded Accel in 1983. Under their leadership, they have built Accel into one of the most prominent venture firms of the last 4 decades. Michael Eisenberg is a Co-Founder and Equal Partner @ Aleph, with a portfolio including the likes of Lemonade, Melio and HoneyBook, they are one of the leading early-stage firms of the last decade. Sonali De Rycker is a Partner @ Accel, one of the leading firms of the last 3 decades with a portfolio that includes the likes of UiPath, Miro, Spotify and many more incredible companies. Fabrice Grinda is the Founding Partner @ FJ Labs, with over 700 investments, Fabrice has had over 250 exits and built a portfolio including Alibaba, Coupang, Airbnb, Instacart, Flexport, and many more. In Today's Episode You Will Learn: 1.) How does the current environment compare to prior busts? 2.) How will the changing interest rates impact the startup funding climate moving forward? 3.) Why is the rate of inflation the only true metric which reveals the ultimate fate of the economy? 4.) What are the world's leading investors telling their founders? 5.) How are the best investors in the world thinking through reserves management?

Sonali De Rycker is a Partner @ Accel, one of the leading firms of the last 3 decades with a portfolio that includes the likes of UiPath, Miro, Spotify, and many more incredible companies. As for Sonali, Sonali led Accel’s investments in Avito (acquired by Naspers), Spotify (NYSE: SPOT), Primer, Monzo, Letgo (acquired by Naspers), Kry/Livi, Soldo, Hopin, and Sennder. Prior to Accel, Sonali was with Atlas Venture (now Accomplice). She also previously served on the board of Match.com (NASDAQ:MTCH). In Today's Episode with Sonali De Rycker You Will Learn: 1.) From Small Town in India To Leading Venture Capitalist: How Sonali made her way from a small town in India to becoming one of the most prominent VCs of the last decade? What were some of Sonali's biggest lessons from seeing the booms and busts of 2000 and 2008? What climate does the crash today resemble more? Why so? How does Sonali advise younger investors who have not lived through a downturn? What should their investor psychology be right now? 2.) Firm Building: Accel: What are the most challenging and non-obvious elements of building a firm today? What have been some of the biggest mistakes Accel has made when adding to the team? What qualities do Sonali and Accel specifically look for when interviewing candidates to join the team? What specific questions tease out whether the candidate has these traits? What specific structures does Accel have in place to encourage the team to work together as one cohesive unit? How do they use bonuses as a team incentive? 3.) Sonali: The Investor: How has Sonali's investing style changed over the years? What moments caused these changes to happen? What are some of the biggest mistakes Sonali has made in her investing career? What did she learn from them? On the flip side, from winners such as Spotify and Supercell, what did Sonali learn from her biggest winners? Why does Sonali believe that market sizing and outcome scenario planning is useless and will lead you to make the wrong decision? 4.) Decision-Making and Risk: What does Sonali mean when she speaks of Type 1 and Type 2 decisions? How should one's decision-making process change according to which type of decision it is? What are the two biggest risks startups are facing today? Does Sonali believe that seed-stage companies will take money from crossover funds? What does Sonali do when she loses faith in the founder? How does she communicate that to them in the right way? What have been some of her biggest lessons here? What have been some of Sonali's biggest lessons when it comes to reserves management? How does Sonali determine when to double down vs reserve cash? Items Mentioned in Today's Episode with Sonali De Rycker: Sonali's Favourite Book: A Fine Balance Sonali's Most Recent Investment: BeReal

Henri Pierre-Jacques is Managing Partner of Harlem Capital, on a mission to change the face of entrepreneurship by investing in 1,000 diverse founders over the next 20 years. From a kitchen table with his Co-Founder, Jarrid, Henri has scaled Harlem in just a few years to their latest fund last year of $134M, well over-subscribed from their $100M target. Prior to Harlem, Henri was in Private Equity at ICV Partners, and before PE was an Investment Banker at Bank of America Merrill Lynch. In Today's Episode with Henri Pierre-Jacques 1.) From Kitchen Table to $134M Fund: How did Henri make his way into venture having had the idea for Harlem at the kitchen table with his best friend? How did Henri use his angel investing strategically to position him to raise Fund I? How did Henri's mindset change when making the transition from angel to VC? 2.) The First Fundraise: Harlem I How long did it take to raise the first fund? How many meetings did they have? What were the most common reasons LPs said no for the first fund? What were their biggest lessons around what potential LPs did and did not like? How does Henri advise new managers when it comes to meeting new LPs? How does Henri use past deal memos to serve as discussion material with LPs? 3.) Building the Firm: The Strategy: What was the portfolio construction for the first fund? How does Henri separate the world of funds into 3 distinct groups? How did they approach reserves management with the first funds? What are some of Henri's biggest lessons when it comes to effective reserves management? How does Henri assess his own relationship to price and ownership? How does that change with fund size? What are some very important nuances that Henri does not believe many managers think about? 4.) It Is Time For Change: Specifically, what are Harlem street doing to ensure the next generation of investors is much more diverse? How do they leverage their intern program to achieve this? What would Henri like to see change in the world of LPs when it comes to allocating to more diverse managers? What legacy does Henri want to leave with Harlem? What will be a success for Henri? Items Mentioned in Today's Episode with Henri Pierre-Jacques: Henri's Most Recent Investment: Mueshi

Zhenya Loginov is the CRO @ Miro, the leading visual collaboration platform that helps bring teams together and meaningfully improves the way people work. At Miro, I run the go-to-market team of 700+ people across 11 global offices. Prior to Miro, Zhenya was the COO @ Segment where he built and ran the global go-to-market team of 200+ people, expanded the product-market fit into the Enterprise and grew revenue 6x, leading to their acquisition by Twilio for $3.2Bn. Finally, before Segment, Zhenya led a 100-person team at Dropbox across numerous different functional areas. In Today's Episode with Zhenya Loginov You Will Learn: 1.) Entry into Sales as an Outsider: How Zhenya made his way into sales as an outsider and came to be one of the most powerful revenue leaders today with Miro? What are 1-2 of the biggest takeaways for Zhenya from his time at Segment and Dropbox? How did they impact his mindset today? Why did Dropbox not win the enterprise when they had the chance? What mistakes did they make? 2.) The Sales Playbook: What, Why and How: What does "the sales playbook mean to Zhenya? Does the founder need to be the one to create the sales playbook? What are the signs that the founders needs to bring in their first sales hire? Should this sales hire be a sales leader or more junior sales rep? Is is possible to run a PLG and enterprise sales motion at the same time in the early days of the company? What do many founders misunderstand when contemplating adopting an enterprise sales strategy? 3.) Hiring the Team: How does Zhenya structure the interview process for new sales hires? Zhenya spends 5 hours with each candidate, what does he look to get out of each meeting? How does Zhenya break down the criteria for what he wants to see? What are some examples of this? How does Zhenya test to determine if the candidate has these criteria? What questions does he find to be most revealing? Why does Zhenya find case studies to not be useful? How does Zhenya use interview panels to ensure he makes the right hiring decision? Who is on the panel? At what stage do they meet the candidate? How does Zhenya like to use the panel? 4.) Laying the Groundwork: The Onboarding Process: What is the right way to structure the onboarding process for all new sales hires? What are some early signs that a new sales hire is not working? What can sales leaders do to ensure new reps get "early wins" on the board? What can leadership do to ensure the sales team has good cross-functional communication across the org? What works? What does not work? What are some of the biggest challenges of running a remote sales team?

Gary Vaynerchuk is a serial entrepreneur and serves as the Chairman of VaynerX,  the CEO of VaynerMedia and the Creator & CEO of VeeFriends. Now Gary is a content machine and documents his life as a CEO daily through his social media channels which have more than 34 million followers and garnishes over 272 million monthly impressions/views across all platforms. He is also a five-time New York Times Best-Selling Author and is a prolific angel investor with early investments in companies such as Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase and Uber. If this was not enough, Gary serves on the board of GymShark, MikMak, Bojangles Restaurants, and Pencils of Promise. In Today’s Episode with Gary Vaynerchuk We Discuss: 1.) From Wine Library to One of The Great Angels in Tech: How did Gary make the transition from scaling the wine library to $60M in revenue to angel investing in Twitter, Facebook and Tumblr? To what extent does Gary think luck plays a role in one's success today? What are Gary's biggest lessons from having FB, Twitter and Tumblr as his first investments? How has his style of angel investing changed over time? 2.) Hard Lessons Learned and Insecurity: What is the most painful lesson Gary has learned that he is also pleased to have learned? How did Gary's relationship with his father impact how he engages with his children as a father today? What are Gary's biggest insecurities today? How does he try and combat them? What works? 3.) Money and Success: How does Gary evaluate his relationship with money today? How has it changed over time? Why does Gary believe that most people think too short-term? What can one do to inspire a more long-term mindset to building? Does Gary believe that everything has a price? What is the one thing for Gary that does not have a price? 4.) Resource and Time Allocation: How does Gary determine the projects to do vs not to do? How does Gary know when to quit a new project? How does Gary advise founders on when something is not working and knowing when to quit? What are some of the biggest mistakes Gary sees founders make when it comes to resource allocation in the early days?

Nick Jones is the Founder & CEO @ Soho House, it all started in 1995 when Nick opened the first location above his restaurant, Cafe Boheme, a members’ club for the local artists and actors of London. Today, Soho House is a global brand, a private members club that includes 33 Houses in 14 countries, with more openings in Europe, Asia, and North America on the horizon. In 2021, Nick took Soho House public on the NASDAQ, 25 years since opening the first location. If that was not enough, Nick is also the owner of Babbington House and Cecconi's, one of my favorite restaurants in London. In Today's Episode with Nick Jones You Will Learn: 1.) The Start of Soho House: What was the founding moment for Nick with Soho House? What were the biggest lessons from his 3 prior restaurants not working? How did that experience change his approach to Soho House? Why does Nick believe resilience is the most important skill of any entrepreneur? When something is not working? What does Nick tell himself? With the rise of Instagram, how have the demands of the consumer changed over time in terms of what they expect from hospitality? 2.) The Art of Storytelling: What does Nick believe is the essence of truly great storytelling? What do all great stories contain? How do the best storytellers tell those stories? Where does Nick believe many founders make mistakes when it comes to storytelling today? 3.) The Art of Leadership: How does Nick define his style of leadership today? How has it changed over time? What does high performance mean to Nick? How does Nick think through retaining high performance while also having a family? How does Nick approach hiring? Why does Nick find interviewing so tough? How does Nick think through when to hire someone external vs promote internal talent? 4.) The Scale of Soho House: What was the single most challenging time in the scaling journey of Soho House? What changes when you go public? What are the good? What are the bad? What does Nick know now that he wishes he had known in the beginning?

Adam Fishman is one of the leading growth practitioners of the last decade. Most recently, Adam was the Chief Product and Growth Offer at Imperfect Foods, where Adam built a 40-person product and growth organization, responsible for 70% of overall company metrics and growing revenue by 400% in one year to $600M annually. Before Imperfect, Adam spent 4 years as VP of Product and Growth @ Patreon, driving the company pivot and rebrand and helping the company scale to $1BN GMV and $100M in revenue. Finally, before Patreon, Adam was the Head of Growth @ Lyft, Adam was the first growth and marketing employee hired, grew the team to 18 people, and reported directly to the founders. In Today's Episode with Adam You Will Learn: 1.) Entry into Growth: How Adam first made his way into the world of growth when "growth" did not exist as a function? What were Adam's biggest lessons from leading Lyft's growth team? How did that impact his mindset? What are some of Adam's biggest takeaways from his time at Patreon? What are some of the biggest mistakes he made at Patreon? 2.) The Basics: Growth 101: What and When: How does Adam define "growth" today? What is it? What is it not? When is the right time to hire your first growth hires? Should this first hire be a seasoned growth leader or a more junior growth rep? What characteristics and skill sets should this growth hire have? 3.) The Hiring Process: How should founders structure the hiring process for their first growth hire? What 3 questions should all founders ask in the hiring process for growth? How can founders use data and case studies to really test the skillsets of growth candidates? Why does Adam believe that the hiring process for growth and product is so broken? 4.) The Onboarding Process: What is the right way to structure the onboarding process for new growth hires? How should growth hires create cross-functional relationships and communication with the rest of the team? What has worked for Adam in the past? What has not? What are the signs that are new growth hire is not working? How long should they be given? What are the signs that are a new growth hire is working? What is the sign of "exceptional"? 5.) Adam Fishman: AMA: What growth decision has Adam made without data? How did it go? How does Adam define "viral loops"? What makes one better than another? Where do so many make mistakes with viral loops? Adam led the rebrand for Patreon, what is the secret to a successful rebrand? What are some of the most common pitfalls to avoid? Items Mentioned in Today's Episode with Adam Fishman Adam's Favourite Book: First 90 Days, Critical Success Strategies for New Leaders at All Levels

Dharmesh Shah is the Founder and CTO @ Hubspot, a full CRM platform with marketing, sales, service, and CMS software. Dharmesh started Hubspot in 2006 and today it is a publicly-traded company (NYSE: HUBS) with over 3,500+ people and a market capitalization of $16.9 billion. Prior to founding HubSpot, Dharmesh founded Pyramid Digital Solutions, which he bootstrapped with less than $10,000 and after 11 years of CEOship, Dharmesh helped the company get acquired in 2005 by SunGard Business Systems. In addition to co-authoring “Inbound Marketing" Dharmesh founded and writes for OnStartups.com -- a top-ranking startup blog and community with more than 1,000,000 members. Finally, if all of this was not enough, he is an angel investor in over 90 startups, including Coinbase, AngelList, Gusto, Okta and many more. and a frequent speaker on startups, growth, and the business of technology. In Today's Episode with Dharmesh Shah We Discuss: 1.) The Founding of Hubspot: How did Dharmesh's wife help Dharmesh find his co-founder in Brian? What about SMB did both Dharmesh and Brian find a shared passion for? What is the single biggest mistake Dharmesh made in the early days of Hubspot? 2.) The Culture Code: What is Dharmesh's single biggest advice to founders when it comes to culture? What does Dharmesh mean when he says "you have to treat culture like a product"? What does Dharmesh mean when he says he looks for a "low ego to accomplishment ratio"? How does he test for this when hiring new hires? How do the best people approach both responsibility and accountability? How does this show in their work and behaviour? 3.) The 3 Kinds of Risk in Startups: What does Dharmesh believe are the 3 core risks all startups face in the early days? How does Dharmesh advise founders when it comes to "testing for a market"? What is the right way to do customer discovery? What are the biggest mistakes founders make in the discovery process? How does Dharmesh advise founders on when to release their second product? What is the right framework for this decision? Where do so many founders make mistakes here? How does Dharmesh approach market timing risk? What have been his biggest lessons here? 4.) SMB vs Enterprise: Why does Dharmesh believe that SMB is the single best market for founders to choose? What are the single biggest challenges with enterprise? How do the long sales cycles and contracts in enterprise hide both customer satisfaction and prevent product development? What are some of Dharmesh's biggest lessons on pricing? Does Dharmesh agree you should always "raise your prices"? How does Dharmesh advise founders on when is the right time to go into enterprise from SMB? What are the single biggest changes founders need to know when making the move from SMB to enterprise? 5.) Angel Investing 101: What are Dharmesh's rules when it comes to angel investing? What have been some of Dharmesh's biggest lessons from analysing thousands of emails to founders pre-investing? What are the biggest signs in emails of future founder success? Why does Dharmesh not have calls with founders before investing? What are some of the biggest mistakes Dharmesh has made when angel investing? Items Mentioned in Today's Episode with Dharmesh Shah: The Hubspot Culture Code Dharmesh's Favourite Book: Les Miserables

Ruchi Sanghvi is a Founder and Partner @ South Park Commons Fund, a home for the most talented technologists, builders, and domain experts figuring out what's next. Prior to SPC, Ruchi was the first female executive at Dropbox and served as their Vice President of Operations. Prior to Dropbox, Ruchi was the first female engineer at Facebook, and was instrumental in implementing the first versions of key features like News Feed, Facebook Platform, Facebook Connect and Privacy. Ruchi has also served as a director on the board of Paytm, India’s largest mobile payments platform. Prior to SPC, Ruchi was an active angel investor in 50+ companies including Gusto, Pinterest, Paytm, Brex, Figma, and Stemcentrx. In Today's Episode with Ruchi Sanghvi: 1.) From First Female Engineer To Community Leader and Fund Manager: How Ruchi made her way into the world of tech becoming the first female engineer at Facebook? What were her biggest lessons from her time at Facebook? What does Ruchi believe makes Mark Zuckerberg the special leader he is? How did Ruchi's time at Dropbox impact how she operates today? Does Ruchi agree with the Facebook motto, "move fast and break things"? 2.) Answering Life's Big Questions: Ego, Money, and Insecurity: What advice did Ruchi's father give her before he passed away that really impacted how Ruchi operates and acts in the world today? How does Ruchi assess her own relationship to money? How has it changed over time? How does she use a spreadsheet to measure her relationship to money? Having had such success so young, how does Ruchi approach ego management? When has Ruchi been arrogant in the past? How does she manage her ego today? What are Ruchi's biggest insecurities today? Why are they? 3.) Will DAOs Replace Venture Capital: How does Ruchi analyze the crypto fund landscape today? Where are the opportunities? Does Ruchi believe that large multi-stage firms can simply hire crypto partners and win in the new world of Web3 and crypto? How does Ruchi believe DAOs will disrupt the venture model today? Will DAOs displace institutional LP dollars from venture funds and be directed to DAOs? How are DAOs governed today? Who makes the decisions? How are tokens allocated? 4.) -1 to Zero: The Art of the Pick: What does Ruchi mean when she speaks of -1 to zero? What stage of company formation is this? What is the right framework by which founders should approach picking an idea to work on? How should a founder know when to give up and try a new idea? What are the most common mistakes founders make in this stage of idea picking?

Kayvon Beykpour is one of the most prominent product leaders of the last decade. For the last 7 years, Kayvon has been at Twitter where he led all of the teams across Product, Engineering, Design, Research and Customer Service & Operations. Kayvon came to Twitter through Periscope, the live broadcasting app that raised from GV, Bessemer, Scott Belsky and was ultimately acquired by Twitter in 2015. If that was not enough, Kayvon is also an active angel investor today. In Today's Episode with Kayvon Beykpour You Will Learn: 1.) Entry into Product: How did Kayvon make his way into the world of tech and come to be Head of Consumer Product @ Twitter? What were some of Kayvon's biggest lessons from the journey with Periscope? What were some of Kayvon's biggest takeaways from working closely with Scott Belsky? 2.) Building Your Product Team: How does Kayvon advise on your first product hires? Should it be Head of Product or more junior product team members? When is the right time for the founder to hand off some core product decisions to these hires? What are the core traits and characteristics of some of the best first product hires? 3.) Perfecting the Hiring Process for Product Teams: How does Kayvon approach the hiring process for all new product team members? What are the stages? What does he look to learn at each stage? What questions reveal the most in product candidates? How do the best respond? How does Kayvon use case studies and product demos in the process? 4.) Building Product: 101: How does Kayvon approach product reviews? Who is invited? Who sets the agenda? How often? What have been Kayvon's biggest lessons about what leaders need to do to get the most from their product teams? How do they communicate? What has been one of Kayvon's biggest product mistakes? What did he learn? How does Kayvon advise founders on when to give up on a new product vs when to iterate and persist?

Ian Lee is the Co-Founder of Syndicate, a web3 startup that has raised over $28M from a16z, Kleiner Perkins, IDEO, and 300+ investors. Previously, Ian was Managing Partner of IDEO CoLab Ventures, a crypto venture fund backed by IDEO focused on web3, crypto, and blockchain startups. From 2017-2021, Ian led investments and helped incubate 80+ crypto startups in the areas of DeFi, NFTs, DAOs, and more. From 2014-2017, Ian was the Head of Crypto at Citigroup and Citi Ventures globally. Listen to our prior episode on DAOs with Avichal Garg here. In Today's Episode with Ian Lee We Discuss: 1.) Ian's Entry into Tech and Crypto: Why did Ian decide early on that he did not like being a VC? What was it that changed his mind, showing him the impact investing can have? What have been the most significant but non-obvious developments in crypto? 2.) Why DAOs Will Replace Venture Capital: Why does Ian believe that DAOs will replace venture capital firms over time? How does Ian analyze the current landscape of Web3 investing and VC? Can existing firms layer on a Web3 Partner or Fund and win in the new Web3 landscape? How will the next generation of Web3 native firms be structured? 3.) DAOs 101: What really is a DAO? What is not a DAO? How are DAOs structured? How many people are invited? Who decides who is invited? How are decisions made within DAOs? How does this differ dependent on structure? What are the single biggest challenges that DAOs face today in operations? 4.) Crypto is The Future of the Internet: What does Ian mean when he says "crypto is the future of the internet"? What does this mean for the distribution of ownership and wealth in the next generation of the internet? Do DAOs and Web3 do more to harm or hurt income inequality today? What are the drivers that would lead Web3 to centralize wealth even further? Items Mentioned in Today's Episode with Ian Lee: Ian's Fave Book: The Innovator's Dilemma: The Revolutionary Book That Will Change the Way You Do Business Ian's Fave Web3 Resources: a16z's Crypto Canon, Jesse Walden's: The Ownership Economy 2022

Over the last 10 days, we have seen unprecedented levels of layoffs from some of the biggest quick commerce providers in the world from Getir to GoPuff to Zapp and Gorillas. Today we dive into the world of quick commerce in emerging markets to uncover what is the same and what is different about the model in emerging markets. Usman Gul is the Founder & CEO @ Airlift, one of the fastest-growing quick commerce providers in the world with core operations in Pakistan. Airlift has raised over $100M in funding from First Round, Josh Buckley, Sam Altman, and 20VC. Ralf Wenzel is the Founder & CEO @ JOKR, a unique provider in the quick commerce market with their dual operations in both the US and LATAM. They are one of the only providers to operate in both emerging and developed economies. To date, JOKR has raised over $288M from Softbank, Balderton, GGV, and Kaszek to name a few. Aadit Palicha is the Founder & CEO @ Zepto, they have taken the Indian quick commerce market by storm since their early days in YC. To date, Aadit has raised over $360M with Zepto from YC, Lachy Groom, Breyer Capital, and Rocket Internet to name a few. In Today's Episode on Quick Commerce in Emerging Markets You Will Learn: 1.) Emerging Markets vs Developed Economies: Where is Quick Commerce Best? What are the single biggest benefits for quick commerce providers in emerging markets? What are the single biggest challenges of operating quick commerce companies in emerging markets as compared to developed economies? From a cost of goods and delivery perspective, what is the single biggest difference comparing operating in emerging markets? 2.) Warehouses, Picking and Delivery: The Economics Broken Down: What % of revenue does Zepto, Airlift and JOKR spend on average for new warehouses in mature markets? How does this change over time? How do they select warehouse locations? What % of revenue is picking costs for Zepto, Airlift and JOKR? What are some needle moving things that could reduce this picking cost? What % of revenue is delivery costs for Zepto, Airlift and JOKR? What levers can make this driver efficiency and delivery cost more efficient? What % of AOV does Airlift and Zepto charge for delivery? How does Zepto leverage power users to subsidise the delivery costs for newly acquired users? Why does JOKR not agree with charging delivery fees? How does charging delivery fees impact usage, frequency and AOV? 3.) Product Selection and Margins: Who Goods Have The Highest Margins? How do Zepto, Airlift and JOKR select the products they sell? How do the margins differ across different product categories? Why is fruit and vegetable the most important category for all three providers? What other metrics are heavily impacted by large spend on fruit and vegetable spend? 4.) AOV and Customer Spend: What is Good? What is the AOV for Airlift, JOKR and Zepto today? How do new markets compare to more mature markets? What are the drivers of the increase? Why does Zepto not believe that AOV is the right metric to be tracking? Why is gross profit per order the right metric to be tracking? 5.) Additional Business Models: Advertising: How much revenue does JOKR, Airlift and Zepto make from advertising revenue today? What can be done to increase this? How have JOKR been able to scale advertising revenue in such a short space of time? What has worked? What has not worked? How important is advertising revenue to the future sustainability of the business model?

Keith Rabois is a General Partner @ Founders Fund, one of the best performing funds of the last decade with a portfolio including Facebook, Airbnb, SpaceX, Stripe, Anduril, the list goes on. As for Keith, he has led the first institutional investments in DoorDash, Affirm and co-founded Opendoor. He has also led investments in Faire, Ramp, Trade Republic, and Stripe. As an operator, Keith has an unparalleled track record as a Senior Exec at Paypal, he then went on to influential roles at Linkedin and being COO at Square. Finally, as an angel, Keith made early investments into Airbnb, Lyft, Palantir, Wish and more. In Today's Episode with Keith Rabois: 1.) Buy Low, Sell High: What BS! Why does Keith believe that "buy low, sell high" does not work in venture? Why would it lead you to very dangerous investment decisions at the early stage? How does the size of your fund impact the appropriateness of "buy low, sell high"? 2.) The Current Landscape: Does Keith believe the current state of public markets is an over-reaction or a new normal? How does Keith respond to the suggestion that Founders Fund has paused new investments given the uncertainty in the market? How does Keith think about investing through cycles and temporal diversification? How does Keith advise young investors today questioning whether they are actually any good at this? What does Keith believe are his biggest fears and insecurities today? 3.) Outcome Scenario Planning and Competitor Analysis: Does Keith believe outcome scenario planning is important? Why does Keith believe you can always tell your biggest hits early? What have been the core signs for him? What have been some of Keith's biggest lessons from Mike Moritz and Vinod Khosla when it comes to upside maximization? What are the right questions to ask? Why does Keith believe you do need to look through public market comps when investing in startups? 4.) Time Allocation and Losing Faith in Founders: How does Keith approach time allocation across the portfolio? Spend time with the winners or help the struggling companies? What have been his biggest lessons here? What does Keith do when he has lost faith in the founder? How does he communicate it to them? What does Kieth believe VCs do wrong when they no longer believe in the founder or company? 5.) Do VCs Add Value? What does Keith believe is the acid test for whether he is doing his job as a VC properly? Why does Keith believe there are only 5 board members that add true value to their companies at scale? Who is the best board member Keith has ever worked with? Why? Why does Keith believe that age is not your friend as an investor? How does he combat this? 6.) The Downfall of SF and Wokeness: Will we see a reduction of wokeness in companies with the public markets correcting and power shifting from employees to employers? Is Keith concerned by the lack of coherence in the US today when it comes to politics? What are the core reasons for the downfall of SF to Keith? Why does he believe it is a net negative to build a company in SF today? Items Mentioned in Today's Episode: Keith's Most Recent Investment: Found

Aydin Senkut is the Founder and Managing Partner of Felicis. An original super angel turned multi-stage investor, he has been named on the Forbes Midas List for the past nine years (2014-2022). Felicis has been an incredible 16-year journey starting with a $4M Fund I back in 2006, their most recent fund in 2021 was $900M. Along the way, Felicis has invested in over 45 unicorns including Adyen, Canva, Shopify, Notion, Opendoor, and Plaid. Prior to starting Felicis, Aydin was a Senior Manager at Google where he spent an incredible 6 years. In Today’s Episode with Aydin Senkut: 1.) The Founding of Felicis: How did Aydin transition from a successful angel to the first $41M institutional fund with Felicis? How did Aydin's mindset change moving from investing personal to LP capital? What does Aydin know now that he wishes he had known when he started Fund I? 2.) Fund Mechanics: Building a Portfolio Why does Aydin believe portfolios need to have 40-50 positions to be diversified enough? Given Aydin being multi-stage, how important is ownership on first check for Aydin and Felicis? Does Aydin believe it is possible to really concentrate capital into your best performers? How does Aydin think through outcome scenario planning? What is his biggest takeaway from this? 3.) Aydin Senkut: The Investor What have been the biggest changes in Aydin's style of investing over the last 16 years? What was Aydin's biggest miss? How did it impact his mindset moving forward? What is Aydin's biggest insecurity as an investor today? How has it changed? Where does Aydin still believe he is weak as an investor? What is he doing to combat it? 4.) The Venture Landscape: Why does Aydin believe that despite the pricing, seed is the best risk-adjusted asset class? How does Aydin evaluate where crossover funds will move with the death of many growth rounds? What segment of the market will be hit hardest by the crunch? What worries with this? What would Aydin most like to change about the venture landscape today? Why? Item’s Mentioned In Today’s Episode with Aydin Senkut Aydin’s Favourite Book: The Black Swan: The Impact of the Highly Improbable

Oliver Jay (OJ) is one of the most successful sales leaders of the last decade. Most recently, OJ spent 6 years at Asana where he was hired as the company's first revenue leader. As CRO, OJ was responsible for product-led and sales-led revenue and grew the team from less than 20 to over 450. Before Asana, OJ spent 4 years at Dropbox in a period of hyper-scaling for the business where OJ was Head of APAC and LATAM. At Dropbox, OJ scaled the sales team from 0 to 50 while tripling ARR. If that was not enough, OJ is also an independent board member at Grab, the leading Super app in Southeast Asia. In Today’s Episode with Oliver Jay You Will Learn: 1.) Entry into Sales: How did OJ make his way into sales with Dropbox? If OJ were to choose 1-2 lessons from his time at Dropbox and Asana that have stayed with him, what would they be? How did they impact his mindset? What were some of the non-obvious but crucial things Asana and Dropbox did in sales that led to success? 2.) The Playbook: Why does OG disagree with so many definitions of "the sales playbook"? What is the sales playbook to OJ? What are the different chapters? Should the founder be the one to create the sales playbook? What are the signs that the founder has a repeatable and scalable playbook? When is the right time to hire the first sales rep? Should it be a Head of Sales or Sales Rep? How does the first hire depend on whether you are PLG or enterprise sales led? 3.) The Hiring Process: How does OJ structure the hiring process? How does OJ know the qualities that he wants to uncover in each candidate? What questions does OJ ask to unpack whether the candidate has those qualities? How does this differ when hiring sales reps vs sales leaders? How does OJ use the sales demo to test the quality of a candidate? What does he want to see? Who does OJ bring into the interview process? When do they get involved? What are two questions that will immediately tell whether someone is a good manager? 4.) Sales Onboarding: How does OJ segment sales onboarding into 3 crucial steps? Chapter 1: Support: Why does OJ believe it is so important for reps to spend their first week with support? What should they look to learn? What questions should they be asking? Chapter 2: Market Knowledge: How can sales leaders teach and educate new reps on market landscape, dynamics and competition? Why does this have to come before sales training? Chapter 3: Sales Training: In the final step, what does the sales training process? What does OJ look for in the final sales demo? When does OJ let reps speak to customers? How does this differ when comparing enterprise to PLG?

Oren Zeev is the Founding Partner @ Zeev Ventures and one of the OGs of solo capitalism. Oren has an incredible portfolio including investments in Audible, Houzz, Chegg, Riverside, Tipalti, TripActions, and Firebolt to name a few. Oren is also very unlike any other VC firm, he does not employ any associates, principals, or staff. He doesn't have partners or partner meetings. No LP meetings. No processes. No investment committees or memos. Nada. Oren is doing it differently. Prior to starting Zeev Ventures, Oren spent 12 years as a GP @ Apax Partners where he c-headed their technology practice in their Silicon Valley office. In Today’s Episode with Oren Zeev You Will Learn: 1.) Origins into Venture: How did Oren make his way into venture over 20 years ago? How does the crash of today compare to the dot com and 2008? What is the same? What is different? Why did Oren decide to leave Apax and start Zeev Ventures on his own? 2.) Deployment Pace: Why does Oren believe that the benefits of temporal diversification are overstated? Oren raised 3 funds and over $1BN in a year, how does this current environment impact how Oren thinks about deployment pace? Will he change anything? How does Oren explain deployment pace to LPs who question him? 3.) Ownership: How central a role does ownership play for Oren in terms of his investor psychology? Does Oren believe it is possible to increase your ownership in subsequent rounds, in your best companies? What are the biggest mistakes that big funds make with regards to ownership requirements? Why is there a misalignment between GP and LP when it comes to increasing ownership vs markups? 4.) Price Sensitivity: How does Oren evaluate his own relationship to price today? What have been some of Oren's biggest lessons on price from his biggest wins and losesses? What mistake do the majority of investors make when it comes to price? 5.) Diversification: Why does Oren believe that both GPs and LPs are wildly over-diversified in their portfolios? What is the right amount of companies for GPs to have in their portfolio? How does Oren advise LPs on the right amount of funds for them to be invested with? 6.) Oren Zeev: AMA: What does Oren know now that he wishes he had known when he started his career in venture? What elements of the world of LPs would Oren most like to change? Why does Oren feel that the concept of pro-rata is a lazy one? Item’s Mentioned In Today’s Episode with Oren Zeev Oren’s Most Recent Investment: Bad Blood: Secrets and Lies in a Silicon Valley Startup

Ian Siegel is the Founder and CEO @ ZipRecruiter, a leading online employment marketplace that uses AI-driven matching technology to actively connect millions of businesses and job seekers to their next great opportunity. Since co-founding the company in 2010, more than 1.8M employers have used ZipRecruiter to find their next great hire and over 500 million job applications have been submitted through the site. Prior to their IPO last year, Ian bootstrapped the company for many years to many millions in revenue before taking venture funding from IVP, Wellington Management and Basepoint Ventures to name a few. Before founding ZipRecruiter, Ian served in key leadership roles at CitySearch, Stamps.com, and Rent.com (an eBay company). In Today’s Episode with Ian Siegel You Will Learn: 1.) The Founding of Olo: How did Ian co-found ZipRecruiter from his kitchen with no venture funding and his 3 friends? Why did they decide to not raise venture funding in the early days? What was the catalyst at $50M in revenue for realising now was the right time to raise funding? 2.) The Art of Great Storytelling What does truly great storytelling mean to Ian? What are the components of a great story? Why do so many people today f*** up their product marketing and messaging? Why does Ian believe Version 1.0 is the only one that takes true courage? 3.) CEO's Do As Little As Possible Why does Ian believe his job as CEO is to do as little as possible? How does Ian determine between the things he, the CEO should do, vs those those he should delegate? Why does Ian believe the art of leadership and the art of parenting are the same? 4.) The Art of Hiring: How has Ian's approach to hiring changed over the years? What does Ian mean when he says, "I look for pointy people"? How does he detect them? What are the two qualities that make the best execs? What questions reveal them? 5.) Parenting and Marriage: Does Ian worry that with increasing family commitments, he loses an inch on work? Why does he believe he is in an advantage as a CEO to those that do not have children? What was the biggest argument he has had with his wife? How did it change his perspective? Item’s Mentioned In Today’s Episode with Ian Siegel Ian’s Favourite Book: Living with a SEAL: 31 Days Training with the Toughest Man on the Planet

Darius Contractor is one of the pre-eminent growth leaders of the last decade. As a growth OG, he has been VP Growth @ Airtable, where he led the growth, engineering, and product teams. Before Airtable, Darius was Head of Product Growth @ Facebook Messenger and finally, before Facebook, Darius spent 4 years as Head of Growth Engineering at Dropbox; here, Darius helped drive Dropbox to $100M in net new revenue through Dropbox Business. If that was not enough, Darius is also an active angel and fund investor with a portfolio including Calm, Airtable, Clubhouse, Census and LP checks in Maven Ventures and Long Journey Ventures. In Today’s Episode with Darius Contractor You Will Learn: 1.) Darius Contractor: Entry into Growth: How did Darius make his way into the world of growth? What was that first entry position? What are 1-2 of the biggest takeaways for Darius from his time at Airtable, Dropbox and Facebook? What 1-2 pieces of advice would Darius give to a growth leader starting a new role today? 2.) When is the Right Time: What does the term"growth" really mean to Darius? How do so many confuse it? When is the right time to make your first growth hire as a startup? Should this hire be a junior growth person or a growth leader? Should this initial growth team be placed inside an existing team or as a standalone team? Where do so many startups make mistakes when making this first hire? 3.) Who To Hire: How does one structure the process for your first growth hire? What are the stages? What are the qualities that we are looking to uncover in these first hires? What are the 4 interview stages to go through to test for these qualities? How should founders use case studies and practicals as a way to test for these qualities? 4.) Onboarding and Integration: What does the optimal onboarding process for new growth hires look like? What do the best growth hires do in the first 30/60/90 days? What are some early red flags that a new hire is a mis-hire? How can leaders encourage cross-functional communication between growth and the rest of the org?

David Fialkow is the Co-Founder and Managing Director @ General Catalyst, one of the leading venture firms of the last decade with a portfolio including Stripe, Snap, Airbnb, Anduril, Canva and many more amazing names. Prior to founding General Catalyst with Joel Cutler, David was a serial entrepreneur building and selling 4 successful companies. In Today’s Episode with David Fialkow: 1.) Everything Great Starts Small: How did David and Joel decide on a Hawaiin beach that they wanted to start General Catalyst? Why did they decide to name it General Catalyst? How did the first fundraise go for GC Fund I? 2.) Creating a Firm: The Early Days What design objectives did Joel and David have when they started the firm? How did Joel and David think about firm expansion; going to the West Coast? Coming to Europe? Going multi-stage? What drives their decision to do new products? On reflection, what were some of the toughest elements of the early days with GC? What does David believe they got right? Why? What did they get wrong? How would he change it? 3.) The Partnership: What does David believe makes for a truly successful venture partnership? How does a great venture partnership align to what makes a successful marriage? How does David approach trust? How does he build it with people? What situations would cause David to lose trust? Why do so few people understand it? What does David believe is the true secret to authentic relationship building? 4.) Doing the Impossible: Generational Transition: What does David believe they did so right in their generational transition at GC? What do many firms get wrong in handing over the reins to the next generation? What are the biggest commonalities between venture partnerships and filmmaking? Mentioned in Today’s Episode with David Fialkow: David’s Favourite Book: The 7 Habits Of Highly Effective People

Tony Fadell, often referred to as the father of the iPod is one of the leading product thinkers of the last 30 years as one of the makers of some of the most game-changing products in society from the iPhone and iPod to more recently founding Nest, creating the Nest Thermostat, leading to their $3.2BN acquisition by Google. Tony recently released Build, this is a masterclass taking 30 years of product and company building lessons and packaging them for you, check it out here. In Today's Episode with Tony Fadell: 1.) Everything Great Starts Small: How did Tony make his way into the world of product in the early days? What were his biggest takeaways from the massive flop of General Magic? How did Tony come to Apple and what were the early creation days of iPod and iPhone? 2.) Data and Brand: Does Tony believe great product building is art or science? When should teams listen to their gut vs the data? When was a time that Tony listened to his gut? When was a time Tony listened to the data? How did each situation evolve and turn out? How does Tony think about creating a truly special first mile experience? Where do so many companies go wrong in the first mile today? How does Tony balance between business decisions (COGs etc) and product decisions that will delight customers? 3.) Lessons from Steve Jobs on Product Marketing: How does Tony define great product management? Why do so many people get it wrong? What are Tony's biggest lessons from working with Steve Jobs on what makes great product marketing? Where does Tony see so many companies make the biggest mistakes when it comes to messaging? What is the difference between messaging, marketing and communications? 4.) Hiring Product Teams: What are the clearest signals of the best product talent when interviewing them? What questions does Tony always ask product people to determine quality? How do great product teams remain upbeat when launches fail and remain modest when they are wildly successful? 5.) Apple Watch, iPod and Apple HiFi: Why was the product messaging for the Apple Watch wrong in the early days? How did it change? Why was the iPod a bad business until the 3rd Generation? What changed? Why did the Apple HiFi fail? How did that impact Tony's mindset? Mentioned in Today's Episode with Tony Fadell: Tony's Favourite Book: Only the Paranoid Survive

Fabrice Grinda is the Founding Partner @ FJ Labs, with over 700 investments, Fabrice has had over 250 exits and built a portfolio including Alibaba, Coupang, Airbnb, Instacart, Flexport, and Delivery Hero, and many more. Prior to FJ Labs, Fabrice served as CEO for three multinational companies; including OLX, one of the largest websites in the world with over 300 million unique visitors per month. As a result of his incredible investing success, Fabrice was named the #1 Angel Investor in the world by Forbes. In Today's Episode with Fabrice Grinda: 1.) Everything Great Starts Small: How did Fabrice make his way into the world of investing from founding 3 companies? How does Fabrice feel about founders raising funds with external LPs? Why does Fabrice feel that investing as an angel made him a better CEO? 2.) WTF is Going On: The Market Today How does Fabrice assess what is happening in the market today? What is causing the massive public market drops we are seeing? How do inflation rates and interest rates have such an impact on where we are? How much of this is a result of COVID, the shift to goods from services and supply chains? 3.) The Optimistic Case: How does Fabrice think things could get better from here? What needs to happen? What could the Fed do to enable this optimistic outcome to take place? What would need to happen in geo-politics and Russia for this to happen? What is the probability today of this optimistic case happening? 4.) The Great Stagnation: How does Fabrice think the economy could go sideways from here? What are the core drivers of this? Why is this the most likely outcome of all? What is the probability of this happening? 5.) The Catastrophe: How could this market get so much worse? What level of interest rate change would cause this outcome to occur? Why does Fabrice think that Switzerland is a "House of Cards"? What would this mean if Switzerland fell? What other European countries does Fabrice think are vulnerable? 6.) What this Means for Venture: How will LPs respond to these differing situations? How does this impact how Fabrice thinks about his rate of deployment? What segment of the market is Fabrice most excited for; early or growth? Mentioned in Today's Episode with Fabrice Grinda: Fabrice's Favourite Book: Sapiens: A Brief History of Humankind

Jason Lemkin is the Founder and Managing Partner @ SaaStr, a social community of 500,000+ SaaS founders and a $100M venture fund. In the past, Jason has made investments in the likes of Algolia, Talkdesk, Pipedrive, and RevenueCat to name a few. Prior to SaaStr, Jason was the Co-Founder and CEO @ Echosign, backed by Emergence Capital, Echosign was bought by Adobe and is Adobe Sign as we know it today. In Today’s Episode with Jason Lemkin You Will Learn: 1.) Origins into Venture: How Jason made his way into the world of venture having sold EchoSign? What were some of Jason's biggest lessons from his first 4 investments being unicorns? 2.) The Importance of Ownership & Multi-Stage Funds How does Jason assess the importance of ownership today? If companies can be $20BN, does ownership really matter? How does Jason advise founders who have offers from multi-stage funds at seed? Why does taking multi-stage money at seed result in less pressure for founders? Does Jason believe that signaling risk from large funds is real, when investing at seed? 3.) Building Your Sales Team Does the founder have to be the one to create the sales playbook? What are the nuances? Should you hire a Head of Sales or sales reps first? What should you expect from each? What are the one criteria that you must look for when hiring your first sales reps? What are the signals that a sales rep or leader is a 10x hire? What works when hiring sales reps, 80% of the time? 4.) Boards and VC Value Add: Why has Jason changed his mind when it comes to boards? Why are some inefficient and some very efficient? How do the best founders manage their board? How do they bring in their exec team? What is the right documentation to prepare for board meetings? Why does Jason prefer slide decks over Notion and Coda? How can leaders use board meetings to direct and goal set with functional leads? Item’s Mentioned In Today’s Episode with Jason Lemkin Jason’s Most Recent Investment: Owner

Chris Sacca is the Founder and Chairman @ Lowercase Capital, one of the best performing funds in the history of venture capital with a portfolio including Uber, Stripe, Twitter, Instagram, Twilio, Docker and many more. Why does Chris believe we have bred a generation of asshole kids? What is the right way to negotiate with children? How has that impacted how he manages his team? Anne Wojcicki is the Founder & CEO @ 23andMe, offering DNA testing with the most comprehensive ancestry breakdown, personalized health insights, and more. How did having kids change Anne's approach to time allocation and risk? Harley Finkelstein is the President of Shopify. Over the last 12 years, Harley has partnered with Tobi to the tune of building Shopify’s revenue to over $4.6BN in 2021 and the team to over 10,000 employees.  Does Harley believe he has always been a good father? What changes has Harley made to be more present and there for his children? Why does Harley advise couples therapy as early in a relationship as possible? Deena Shakir is a Partner at Lux Capital, one of the leading firms investing in emerging science and technology ventures at the outermost edges of what is possible. What specific negotiation tactics from parenting can be applied to business? How can a parent show their children they listen, they understand and are there for them? Why does Deena believe children make you more productive and more efficient? Eric Liaw is a General Partner @ IVP, one of the leading later-stage venture capital and growth equity firms of the last decade with $8.7 billion of committed capital and a 40-year IRR of 43.1%. What have been the biggest challenges for Eric of managing family and work? What have been some of Eric's biggest lessons in terms of how he communicates about his work to his family? Scott Dietzen is Vice Chairman of the Board of Pure Storage and served as the Company’s CEO from 2010 to 2017. Under his leadership, Pure grew to thousands of employees and completed an IPO in 2015. What can parents learn from nature programs? What core elements of parenting are directly transferrable to management?

Harley Miller is the Founder and Managing Partner @ Left Lane Capital, one of the fastest-growing growth equity firms of the last five years. Just yesterday, Left Lane announced the closing of their new fund taking their AUM to over $2BN with an early portfolio including M1 Finance, Masterworks, Choco, GoStudent, to name a few. Prior to founding Left Lane, Harley spent over 9 years at Insight Partners investing in the likes of DeliveryHero, HelloFresh, N26, Calm, Udemy and many more breakout companies. In Today’s Episode with Harley Miller You Will Learn: 1.) Origins into Venture: How Harley made his way into the world of venture with his first role at Insight? What were Harley's biggest lessons and takeaways from 10 years at Insight? 2.) Left Lane: Fundraising What are harley's biggest takeaways on fundraising from speaking to 2,500 LPs for Left Lane I? With that experience in mind, what advice does Harley give to other first time fund managers on what it takes to raise successfully? How did the Left Lane pitch to LPs change over time? What worked? What did not work? With the benefit of hindsight, what fundraising elements would Harley have done differently? 3.) Left Lane: Firm Building What are the hardest elements of building a firm today? How did Harley navigate the transition from investor to fund manager? What was challenging? What is Harley's biggest advice to young people in venture looking to scale their career fast? What are 1-2 core inputs aspiring VCs should focus on as they build their career? 4.) Left Lane: Investing and Consumer How does Harley approach portfolio construction with the new fund? How does Harley think through outcome scenario planning and ownership requirements with the new fund? How does Harley think traditional growth equity models can be applied to consumer investing? What will Left Lane be in 20 years? What firm does Harley want to build? Item’s Mentioned In Today’s Episode with Harley Miller Harley’s Most Recent Investment: Masterworks

Noah Glass is the Founder and CEO @ Olo, the interface between restaurants and the on-demand world powering millions of orders per day. Olo is an incredible tale of capital efficiency, at IPO the company had a net burn of just $6M with $122M in ARR. Noah raised from some of the best in the business with names such as David Frankel @ Founder Collective, Danny Meyer, Scott Shleifer @ Tiger Global, all on the cap table. Prior to founding Olo, Noah was International Expansion Manager for Endeavour Global, launching the first African Endeavour affiliate. If that was not enough, Noah is also on the board of Portillo's, Share our Strength and the Culinary Institute for America. In Today’s Episode with Noah Glass You Will Learn: 1.) The Founding of Olo: What was the founding a-ha moment for Noah with Olo? What did David Frankel do that compelled Noah, now was the time to start Olo? What have been some of Noah's biggest lessons from working with David Frankel? 2.) Capital Efficiency: Scaling to $122M ARR with $6M Net Burn Why did Noah and the team not raise more money in the early Olo days? How does Noah advise early founders who are concerned if they do not raise, their competition will? What are 2-3 of the core levers that allow Olo to be so efficient? What can others learn from them? What would Noah have done differently fundraise wise, with the benefit of hindsight? 3.) Decision Making: The Secret What does Noah mean when he says; "capital allocation and attention allocation are intertwined"? How has Noah changed and evolved his decision-making as a leader? How does Noah use a CEO coach? What do they discuss? How often? What works? What does not? What decision did Noah make that proved to be the wrong one? How did he come back from it? 4.) Noah Glass: The Father and Husband How does Noah do so much as CEO and also not lose an inch on being an amazing father and husband? What does Noah believe is the secret to a truly successful marriage, while also being public markets CEO? How has Noah changed as a father and husband over the years? What has worked? What has not worked? Item’s Mentioned In Today’s Episode with Noah Glass Noah’s Favourite Book: Setting the Table by Danny Meyer

Mitch Tarica is Head of North America Sales at Zoom Video Communications. Before joining Zoom, Mitch spent over 5 years at RingCentral including as Senior VP of Worldwide Sales and Customer Success. Finally, before RingCentral, Mitch was at Oracle for over 7 years in numerous different sales roles. In Today’s Episode with Mitch Tarica You Will Learn: 1.) Entry into Sales: How did Mitch make his way into sales with one of the first SaaS companies in the world? What were his early lessons on what truly great sales entails? What elements does Mitch fear we have lost in the art of sales over time? 2.) The Playbook: Should the founder be the one to create the sales playbook? What are the signs that the founder has a repeatable and scalable playbook? When is the right time to make the first sales hire? Should it be a Head of Sales or Sales Rep? How does the first hire depend on whether you are PLG or enterprise sales led? 3.) The Hiring Process: How does Mitch structure the hiring process? Step by step, what does he want to achieve? What questions does Mitch ask in the first interview, always? What are the 3 traits that Mitch believes all great sales hires have? How does he test for them? How do Zoom use practical sales tests to determine the ability of a potential sales hire? How does Mitch see many founders make mistakes in the sales hiring process? 4.) Sales Onboarding: What are the crucial steps to do sales onboarding right? How should leaders structure the first 30,60 and 90 days for their new reps? What are some early red flags that leaders should watch for with new reps? What more can leaders do to make sure their reps are as successful as possible in the early days?

Deena Shakir is a Partner at Lux Capital, one of the leading firms investing in emerging science and technology ventures at the outermost edges of what is possible. Deena has led a number of investments including in Maven Clinic, Mos, Ramp, Alife and SteadyMD to name a few. Before joining Lux, Deena was a Partner at GV and previously led product partnerships at Google for early-stage products in healthcare, AI/ML and search at Google. Before tech and venture, Deena was an aspiring anthropologist, journalist, diplomat, aid worker and was a Presidential Management Fellow at the U.S. Department of State under Secretary Clinton. There Deena helped launch President Obama’s first Global Entrepreneurship Summit in 2010. In Today’s Episode with Deena Shakir You Will Learn: 1.) Origins into Venture: How Deena made her way from journalism and the world of politics to rockstar healthcare investor? What were Deena's biggest takeaways from seeing her parents build a new life in the US? 2.) Competition in Venture: Why should founders not take multi-stage fund money at seed? What problems does it cause? How do VCs try and justify it? What red flags should founders look for? How does Deena advise her companies when it comes to pre-emptive rounds? When should they take them? When should they not take them? 3.) Deena Shakir: The Person How has becoming a parent changed Deena's operating mentality? Why does Deena believe she has never been better as an investor post becoming a mother? Why does Deena feel so many questions around parenting are wrong? In what ways would she like those questions of female operators and investors to change? 4.) Diversity and Inclusion: We Should Be Optimistic Why is Deena optimistic about the future of diversity and inclusion in tech and venture? What drives her optimism? What remains a cause for concern for Deena on this topic? What more can both companies and venture funds do to improve the landscape? Item’s Mentioned In Today’s Episode with Deena Shakir Deena's Favourite Book: The Power Law: Venture Capital and the Art of Disruption Deena's Most Recent Investment: Mos: Banking for Students

Bill Cillufo is Partner and Head of International Investments at QED, one of the leading fintech venture firms today with a portfolio including Nubank, Kavak, Klarna, Quinto Andar and Bitso to name a few. As for Bill, he has led investments in Nubank, Loft, Wagestream and Creditas among others. Prior to joining QED, he spent nearly 20 years at Capital One, spanning several roles and leading several businesses. During Bill’s last 3 years at Capital One, he led its Co-Brand and Private Label credit card business, building the business nearly from scratch to one of the top few players in the US market. In Today’s Episode with Bill Cillufo You Will Learn: 1.) Origins into Venture: How Bill made his way from 20 years at Capital One to becoming a Partner @ QED? How did Capital One inform his mindset around unit economics? Having seen booms and busts firsthand with Capital One, how did that impact his investing mindset today? 2.) The Landscape: What is Happening? Where does Bill believe the biggest crunch in funding markets is today? Does Bill believe this will trickle down to the early stage? How does Bill advise his portfolio companies on runway and burn given the environment? What does Bill believe that many have not seen that is coming? 3.) Bill Cillufo: The Investor How does Bill analyse his own relationship to price and price sensitivity? How has Bill changed as an investor over the last 5 years? What caused the changes? How does Bill reflect on reserves management given the new landscape we are in? 4.) QED: The Expansion Does Bill believe that expanding geographically has become easier with time? What has become harder about expanding into new geographies? How important does Bill believe partnering with local firms is when VCs enter new territories? Item’s Mentioned In Today’s Episode with Bill Cillufo Bill’s Favourite Book: Tom Clancy: The Hunt for Red October Bill’s Most Recent Investment: Refyne

Aparna Chennapragada is Chief Product Officer @ Robinhood, the company revolutionizing consumer finance with commission-free investing, and tools to help shape your financial future. As for Aparna, prior to Robinhood, she spent an incredible 12 years at Google, most recently as VP and GM for Consumer Shopping and also as the lead AR and Visual Search products. Aparna is also an active angel investor with a portfolio including Khatabook, Statsig and On Deck to name a few. If that was not enough, Aparna is also a board member at Capital One. In Today’s Episode with Aparna Chennapragada You Will Learn: 1.) Origins in Product: How Aparna made her way into the world of product and product management? What were Aparna's biggest takeaways from her 12 years at Google? What does product management mean to Arpana today? 2.) Customer Discovery: 101 What are the 3 different stages of product management? What does great customer discovery look like? What are the best questions to ask? How should one dig deeper? Where do so many make mistakes in customer discovery? What should product people take from the answers? What should they disregard? 3.) The Hiring Process: How should founders breakdown the process of hiring for their first in product? What does the interview process look like? How should founders structure it? What core questions should teams ask of prospective candidates? What are red flags when interviewing potential product hires? What literal tests and case studies can founders do to test the quality of candidates? 4.) The Onboarding Process: How should founders structure the onboarding process for new product hires? What can founders do to make PMs successful in their first 30 days? Where do many product hires make the biggest mistakes in the first 30 days? What can product hires do to build trust with their new team? Items Mentioned in Today's Episode with Aparna Chennapragada Aparna's Fave Resource: Shishir's Executive Onboarding

Henrique Dubugras is the Founder and CEO @ Brex, the company re-imagining financial systems so every growing company can realize its full potential. To date, Henrique has raised over $1.1BN for Brex from some of the best including Ribbit, Greenoaks, DST, IVP, Caffeinated Capital and Elad Gil to name a few. Henrique is also a board member at Mercado Libre. Prior to co-founding Brex, Henrique co-founded Pagar.me, there he scaled the company to $15BN in GMV and over 100 people before selling the company in 2016. In Today’s Episode with Henrique Dubugras You Will Learn: 1.) The Founding of Brex: What was the founding a-ha moment for Henrique and Pedro with Brex? What advice did Evan Spiegel give Henrique when it comes to being a great CEO? 2.) Hiring: The Trials and Tribulations What have been Henrique's biggest hiring mistakes? How do founders know when they are ready to bring in the seasoned exec vs the younger jack of all trades candidate? What have been Henrique's biggest lessons in what it takes to hire true A* talent? Where does Henrique see other founders make big hiring mistakes? 3.) Product Expansion and Marketing: How does Henrique assess when is the right time to release a second product? What have been Henrique's biggest mistakes and lessons when it comes to product marketing? How can one retain the simplicity of product messaging with scaling the product? Brex expanded the product too far, too fast. How did they walk it back so successfully? 4.) Henrique: The Leader How does Henrique approach his own relationship to money today? How has it changed over time? What luxury expenditure has Henrique made over the last 12 months that he feels is worth it? How does Henrique think about ego management? What does he do to keep his in check? Item’s Mentioned In Today’s Episode with Henrique Dubugras Henrique’s Favourite Book: The Innovator's Solution: Creating and Sustaining Successful Growth

Domm Holland is the Founder and CEO @ Fast. Last week Fast announced they would be shutting down the company. In this exclusive 20VC episode we discuss: What really happened with Domm's towing business in Australia? What are the 1-2 biggest mistakes made at Fast? Why has Bolt worked in a way that Fast has not worked? What is it like having Stripe as an investor in your company? Could the board have done more to prevent what happened at Fast?  

Avichal Garg is Co-Founder & Partner @ Electric Capital, last month Electric announced they had raised $1BN for their new fund making them one of the largest independent and crypto-native VC firms in the world. As for Avichal, prior to Electric, he was an investor in crypto projects such as Anchorage, Bitwise, Lightning Labs, and OpenSea and unicorns such as Airtable, Cruise, Deel, Figma, Notion and many more. On the operating side, Avichal successfully sold his last company to Facebook where he became Director of Product Management for the Local product group, a team of 400 engineers responsible for billions in revenue. In Today’s Episode with Avichal Garg You Will Learn: 1.) Origins into Venture: How did Avichal make his way into the world of startups and angel investing? How did Avichal make the pivot from software to crypto investing? Was Avichal nervous when making the move to institutionalize what had been personal investing? What does Avichal know now that he wishes he had known at the start of Electric? 2.) The Landscape: Crypto Investing How does Avichal assess the crypto fund landscape today? Will we continue to see a small number of firms (a16z, Katie Haun, Paradigm, Electric) dominate the market? What happens to all the small crypto funds that have been raised in the last year? Why does Avichal believe crypto investing is much more collaborative than venture investing? How can venture size returns be made if the ownership levels are so much smaller? 3.) Crypto Firms vs Traditional VC Firms: Why does Avichal believe that crypto is software eating money? What does this mean for traditional venture? Who will survive? Who will die? Who will thrive? Why can generalist firms not compete with crypto native firms? How are the teams of crypto native firms structured so differently to those of traditional VCs? Do crypto projects and investments need the same level of service and help that generalist VCs provide with their platform services? 4.) Tokens - Equity - Liquidity: How does Avichal advise investors on how to think through token vs equity investing? When does it make sense to have a token vs not having a token? How are crypto tokens priced and valued? What do you need to know when buying tokens? How does the liquidity of crypto markets make it challenging for investor psychology? What is the biggest lesson Avichal has learned on when is the right time to sell? 5.) DAOs: 101 What are DAOs? Are they not just another form of government? What makes one DAO successful and another not? What tooling and infrastructure are required to manage a DAO successfully? What does Avichal believe the vision of a DAO should be? How should they define success? Item’s Mentioned In Today’s Episode with Avichal Garg Avichal’s Favourite Book: The End of the World Is Just the Beginning: Mapping the Collapse of Globalization Avichal’s Most Recent Investment: Magic Eden

Eric Liaw is a General Partner @ IVP, one of the leading later-stage venture capital and growth equity firms of the last decade with $8.7 billion of committed capital and a 40-year IRR of 43.1%. At IVP eric has led investments in Datadog, Github, Klarna, Robinhood and UiPath to name a few. Prior to joining IVP, Eric was with Technology Crossover Ventures (TCV) and was actively involved in originating, executing and managing investments, including Netflix, Zillow and eHarmony. As a result of his investing success, Eric was recognized by GrowthCap as one of the Top 25 Software Investors of 2021 and 2020. In Today’s Episode with Eric Liaw You Will Learn: 1.) Origins into Venture: How did Eric make his way into the world of venture way back over 20 years ago? What were some of Eric's biggest lessons from his early years at TCV? What are the most significant changes in venture over the last decade? 2.) Eric Liaw: The Investor: How has Eric changed as an investor over the last decade? What caused those changes? How does Eric reflect on his own relationship to price? How does he determine when to pay up vs when to remain disciplined? What has been Eric's biggest miss? How did it alter his style of investing? From UiPath to Supercell, what has been Eric's favourite story of travelling around the world to win a deal? 3.) The Market: Venture How does Eric expect IPO markets to behave as we move further in 2022? How does Eric expect large M&A to play out for the rest of the year? With the public markets crashing; how does this impact the large growth rounds of 2021? What does Eric expect to happen to early stage pricing with the crash at late stage? How does Eric expect crossover funds to behave in this new environment? 4.) Eric Liaw: The Person How does Eric think about being an awesome Dad and also not losing an inch on being a world class investor? How does Eric reflect on his own ego when having such large investing wins? Where does he feel he is most insecure? How did having children really impact his mindset towards investing and working with founders? Item’s Mentioned In Today’s Episode with Eric Liaw Eric’s Favourite Book: No Rules Rules: Netflix and the Culture of Reinvention Eric’s Most Recent Investment: Aiven

Brian Hale is Vice President of Consumer Product & Growth @ Doordash. Before joining Doordash, Brian spent an incredible 10 years at Facebook, most recently as VP of Product Growth working across Instagram, Messenger, Whatsapp and more. Prior to Facebook, Brian was Director of Growth @ Uptake.com and it all started for Brian in 1999 working at ACDSee in Canada where he was asked to “figure out that search engine thing”.  In Today’s Episode with Brian Hale You Will Learn: 1.) Brian Hale: Entry into Growth: How Brian made his way into the world of growth from being a "marine ceramic engineer"? What were 1-2 of his biggest takeaways from his 10-year journey with Facebook? What are 1-2 of the biggest misconceptions about the Facebook growth team? 2.) When is the Right Time: When is the right time for startups to hire their first growth leads or reps? How should the founder allocate resources to the growth team? Hire new designers, engineers etc for the team or pluck them from existing teams within the company? What are the biggest mistakes startups make on the timing of this hire? How can startups accurately assess whether they have product-market-fit? What levels of retention suggest PMF? How does this change by industry? 3.) Who To Hire: Step by step, how does Brian structure the interview process for all new growth hires? What are the must-ask questions for growth leaders to ask candidates in interviews? What are the clear signs and answers that suggest a 10x growth hire? How do the very best interact with data? What do they really hone in on? What literal tests does Brian do to determine the quality of a hire? How do the best perform? 4.) Onboarding and Integration: What is the optimal onboarding process for all new growth hires? What can leaders do to set their new growth teams up for success? What are the biggest ways new growth hires can mess up in the first 60 days? What have been some of the biggest challenges for Brian in his onboarding at Doordash?

Thomas Tull is a leading entrepreneur and investor as the Founder, Chairman and CEO of Tulco, LLC. he has made notable investments in the likes of FIGS, Colossal, IL MAKIAGE, Pinterest, Zoox and Oculus Rift. Previously, Tull was the founder, CEO and Chairman of Legendary Entertainment, the film company that produced blockbusters including The Dark Knight trilogy, 300 and The Hangover franchise. Outside of his investment work, Thomas is a trustee of Carnegie Mellon University, Yellowstone Forever, the National Baseball Hall of Fame and Museum, and the Smithsonian Institution. If that was not enough, Tull is also part of the ownership group of the Pittsburgh Steelers, the six-time Super Bowl champions. In Today’s Episode with Thomas Tull You Will Learn: 1.) From Laundromats to Legendary Entertainment: How did Thomas first make his way into the world of business starting with laundromats? How did growing up without money impact Thomas' early mindset? What advice does Thomas give to young people today on starting their own business? 2.) Thomas Tull: The Investor: How does Thomas approach risk today? Where is the boundary of acceptable vs unacceptable risk? How does Thomas assess his own relationship to money? How has it changed over time? How does Thomas protect himself from people and occasions where one is being used for their money or status? To what extent does Thomas believe success is luck vs skill? 3.) Legendary Entertainment: How did Thomas make his way into the movie business with the founding of Legendary Entertainment? How did Thomas first meet Chris Nolan? What did the early days of making Batman Begins look like? What were some of the most memorable times from making 300 with Gerard Butler? What were some of the most challenging elements of scaling Legendary? With the benefit of hindsight, is there anything that Thomas would do differently? 4.) The Macro: Why does Thomas believe public markets are the least rational they have ever been? From geo politics to climate change, what is Thomas most worried about today in the world? What does Thomas believe we should focus on as positives moving forward? What should we be excited about? Item’s Mentioned In Today’s Episode with Thomas Tull Thomas' Favourite Book: Sapiens: A Brief History of Humankind Thomas' Most Recent Investment: Colossal

Eduardo Vivas is the Co-Founder and CEO @ Curated, a network where product experts monetize their passion and help consumers make the perfect purchase. To date, Eddie has raised over $141M from some of the best including CapitalG, Greylock and Forerunner to name a few. Eddie is also a stellar angel investor with a portfolio including Telegram, Truebill, AppLovin and Dollar Shave Club among others. Prior to Curated, Eddie spent 3 years at Linkedin as Head of Talent Solutions, following his startup, Bright, being acquired by them in 2014. In Today’s Episode with Eddie Vivas You Will Learn: 1.) The Founding of Curated: What was the aha moment for Eddie with Curated? What were Eddie's biggest takeaways from his prior companies? What did he take with him that worked? What did he disregard that did not work? What were some of Eddie's biggest lessons from Linkedin? How did it impact his mindset? 2.) The Compound Startup: Why did Eddie decide it was right to build so much of the tooling themselves? How does Eddie determine when to buy vs build? What are the biggest mistakes Eddie sees founders making when building multiple internal tools at the same time? How does build a compound startup increase the strategic value of a company? 3.) Hiring: Missionaries not Mercenaries How does Eddie structure his hiring process at Curated? Why does he not believe that startups are for everyone? What are the biggest signals that a person is a missionary and not a mercenary? How do mercenaries act in a way that is different to missionaries? What questions in an interview process show these traits? What are some of the biggest mistakes Eddie has made when hiring? 4.) Equity and Compensation: What is Eddie's biggest advice to founders when it comes to equity allocations for the team? Why does Eddie believe it is crucial to offer and provide secondaries for the team? How does Eddie feel about the amount of secondaries founders take today so early? Item’s Mentioned In Today’s Episode with Eddie Vivas Eddie’s Favourite Book: Predictably Irrational: The Hidden Forces That Shape Our Decisions

Olivia Nottebohm is the Chief Revenue Officer @ Notion where she leads the Sales, Marketing, Customer Success and Customer Experience teams. Prior to Notion, Olivia was the COO @ Dropbox where she achieved the first 4 quarters of profitable growth. Before Dropbox Olivia spent over 5 years at Google including as VP Cloud GTM Operations and Global SMB Sales. Finally, before Google, Olivia spent a whopping 15 years at McKinsey & Company. In Today’s Episode with Olivia Nottebohm You Will Learn: 1.) Origins: How Olivia made her way into the world of startups and tech? What are 1-2 big takeaways Olivia has from her 5+ years at Google? How have they shaped her operating mindset today? How does Olivia balance her love for analysis and data with speed and agility of decisions? 2.) Good vs Great Operations (Ops): What does great ops really mean to Olivia? What are the 1-2 things founders can implement today to improve their ops immediately? What are the core mistakes founders make when instilling ops for the first time? How does Olivia coordinate the global Notion team to be as effective as possible? What has worked? What has not worked? 3.) The Hiring Process: Why does Olivia believe all leaders will have to accept they will not have all the talent they need over the coming years? With that in mind, is it best to hire B players or always keep the bar high? If and when can the bar be lowered? How does Olivia construct the hiring process? What are the core questions she will always ask? What is the secret to great referencing? How does Olivia enable the other side to feel safe telling her everything they know about the candidate? 4.) Cross-Functional Communication: How does Olivia advise founders on the best way to get different functions working together? What works? What does not? What are some big mistakes Olivia sees over and over? At what point in company scaling does this comms begin to breakdown? Item’s Mentioned In Today’s Episode with Olivia Nottebohm Grow Fast or Die Slow: The role of profitability in sustainable growth

Jeff Lieberman is the Managing Director @ Insight Partners, one of the leading investing franchises of the last 25 years with their most recent flagship fund announced earlier this year being a staggering $20BN. As for Jeff, over the last 24 years at Insight, he has led investments in leading companies such as Qualtrics, DeliveryHero, HelloFresh, Cvent, Mimecast, and Udemy. As a result of his many investing successes, he has been selected by AlwaysOn as a Venture Capital 100 winner and by Forbes as a member of the Midas List. In Today’s Episode with Jeff Lieberman You Will Learn: 1.) Origins into Venture: How did Jeff's roommate at college open his eyes to the world of venture capital? What were Jeff's biggest lessons from seeing the work ethic of his parents? How does Jeff imbue the same level of ambition on his children that he had growing up with no money? Why is Jeff keen for his children not to go to college? How does he advise them? 2.) Jeff Lieberman: The Investor: What are Jeff's biggest observations on the current landscape given his seeing first hand the dot com bust and 2008? How is now different? How is it the same? Price Sensitivity: How does Jeff reflect on his own price sensitivity? How has it changed over time? Deployment Pace: How does Jeff analyse deployment pace today both for the industry and for Insight? Does Jeff agree with the notion of "playing the game on the field"? The Biggest Miss: What have been some of Jeff's biggest misses? How did those misses impact the process with which he invests? 3.) Insight: The Firm What are the most challenging elements of firm building today? Why do all juniors have control over the Partners calendars? How does this work in practice? How does Jeff create an environment of safety where very young, junior people feel like they can challenge anyone and have discussion? How do Insight train young people? What is the process? What works? What does not work? 4.) AMA: What does Jeff know now about venture that he wishes he had known when he started? What would Jeff most like to change about the world of venture capital? What advice does Jeff give to young people today entering the industry? Item’s Mentioned In Today’s Episode with Jeff Lieberman Jeff’s Favourite Book: Man's Search For Meaning Jeff’s Most Recent Investment: Choco

Casey Winters is the Chief Product Officer at Eventbrite where he leads the PM, product design, research, and growth marketing teams. Prior to Eventbrite, Casey spent close to 3 years at Pinterest where he led the growth product team. Andy Johns is one of the pre-eminent growth leaders of the last decade. Andy’s career started in growth at Facebook when the company scaled from 100M-500M active users. Since he has worked in some of the leading growth orgs at companies like Twitter, Quora and more recently at Wealthfront as Head of Growth and President. Bangaly Kaba is the Head of Platform Growth @ Popshop Live, a live streaming mobile marketplace that combines commerce, entertainment, and social. Prior to Popshop, Bangaly led the product growth and consumer product orgs at Instacart and before Instacart was Head of Growth @ Instagram, where he built and led the product team that helped grow Instagram from 440M to > 1B monthly actives in 2.5yrs. Elena Verna is a master when it comes to all things starting and scaling growth organizations. Previously, Elena spent over 7 years as SVP Growth @ SurveyMonkey where she ran product, growth marketing, and data teams. Post SurveyMonkey, Elena worked with the rocket ship that is Miro both as Interim CMO and as an advisor. Ed Baker is an angel investor and growth advisor to various startups including Lime, Zwift, Whoop, Crimson Education, GoPeer, and Playbook. Ed was the VP of Product and Growth at Uber from 2013-2017. Prior to Uber, Ed was the Head of International Growth at Facebook. Rob Schutz is Chief Growth Officer and Co-founder at Ro, the healthcare technology company building a patient-centric healthcare system. Under Rob’s growth leadership, Ro has become one of the fastest-growing companies in the country. Prior to Ro, Rob was VP of Growth at Bark, the makers of BarkBox, and helped scale revenue from zero to $100 million. In Today’s Episode with Ed Baker You Will Learn: 1.) Casey Winters: How does Casey define "growth"? How does it differ from product? How do the best growth leaders decide between art vs science when making growth decisions? 2.) Andy Johns: What is Andy's biggest advice to founders looking to build their first growth team? What unexpected choice did Andy decide to make at Twitter that moved the needle for new user acquisition? 3.) Bangaly Kaba: What were some of Bangaly's biggest takeaways from scaling Instagram from 440M users to 1BN? What decisions did Bangaly make without data? How did they go? What did he learn? 4.) Ed Baker: What are Ed's biggest takeaways from facebook around structuring growth teams? What are Ed's biggest pieces of advice for startyups looking to grow internationally? What were some of Ed's biggest learnings from working with Travis @ Uber? 5.) Elena Verna: What is the difference between a good vs great growth model? When does one need to change or amend their growth model? How does one know when it is working? 6.) Rob Schutz: Why does Rob believe that startups should not diversify their customer acquisition channels too quickly? How does Rob assess resouirce allocation and spend on new channels? How did this process look when partnering with the MLB for Ro?

Grant LaFontaine is the Founder & CEO @ Whatnot, the fastest-growing marketplace in the US, empowering people to make a living off their passion. To date, Grant has raised over $225M for Whatnot from the likes of CapitalG, a16z, YC, Scribble Ventures and Wonder Ventures to name a few. Prior to Whatnot, Grant was a PM @ Facebook working on the Oculus App Store and before that was the founder of Kit.com, ultimately acquired by Patreon. In Today’s Episode with Grant LaFontaine You Will Learn: 1.) The Founding of Whatnot: How did Grant make his way into the world of tech and startups? What were some of his biggest lessons from Facebook? How did that impact how he has built Whatnot? 2.) Impossible To Hire Product Managers: Why does Grant believe it is impossible to hire product managers today? How does this impact the decision-making powers of engineers? How does Grant test for this product knowledge in all engineers he adds to the team? What are clear signals of 10x engineers in hiring processes? 3.) A/B Testing and Risk Mindset: Why does Grant not believe in the effectiveness of A/B testing? Why does it not work? Why does Grant believe one of the biggest reasons for startups failing is they do not take enough risk? How does Grant try to ensure that his team takes as much risk as possible with everything that they do? How does mindset to risk change with scale of company and with leadership? 4.) AMA: Why does Grant disagree with founders angel investing? What are the biggest challenges Whatnot has faced in scaling? CEO coach? Who? When? What is the biggest lesson? What is the single driving metric of Whatnot? How does Grant advise founders to determine their North Star metric? Item’s Mentioned In Today’s Episode with Grant LaFontaine Grant’s Favourite Book: Foundation: 1/3 (Foundation Trilogy)

Luciana Lixandru is a Partner @ Sequoia, one of the world’s most renowned and successful venture firms with Sequoia-backed companies accounting for more than 20% of NASDAQ's total value. As for Luciana, at Sequoia she has led investments in the likes of PennyLane, Xentral, Veed and Ledgy to name a few. Prior to joining Sequoia in 2020, Luciana was a Partner @ Accel where she made investments in Hopin, Miro, UiPath, Tessian and Deliveroo. As a result of such investing success, Luciana was #2 on the Midas List in 2021. In Today’s Episode with Luciana Lixandru You Will Learn: 1.) Origins: How did Luciana make her way from a small town in Romania to being Partner @ Sequoia? What were the 1-2 crucible moments in her life that changed the course of her life? 2.) Luciana: The Investor How has Luciana's investing style changed and developed over the years? How does Luciana reflect on her own relationship to price? What misses caused these changes? Hopin, Miro, Deliveroo, UiPath, how did having such winners so early impact Luciana's investing mindset? What would Luciana say is her biggest insecurity today? What drives this? 3.) Sequoia: The Team What are Luciana's biggest takeaways from working with Doug Leone, Alfren Lin, Roelof Botha and Pat Grady? What does the decision-making process look like for new deals within Sequoia? How does the Sequoia partnership create an environment of safety where everyone can discuss and debate freely? How does Luciana approach training and mentorship? What works and what does not? 4.) Sequoia in Europe + Sequoia's Arc: What is Arc? Why was now the right time for Sequoia to do it? What is the structure for the program? How many startups are part of it? Who is able to apply? How much capital do the startups receive? What else do they receive in mentoring etc? In 5 years time, what would success look like for Luciana with Arc? Item’s Mentioned In Today’s Episode with Luciana Lixandru Luciana’s Favourite Book: The Spy and the Traitor: The Greatest Espionage Story of the Cold War

Lenny Rachitsky is one of the OGs of product, having spent over 7 years at Airbnb as a product lead he left to start his newsletter, find it here. This has scaled to thousands upon thousands of readers and is one of the most popular newsletters on Substack. Lenny is also an extremely active angel investor with a portfolio including Figma, Sorare, Clubhouse, Vanta, WhatNot and many more incredible companies. If that was not enough, Lenny also has the best course on product management, check it out here. In Today’s Episode with Lenny Rachitsky You Will Learn: 1.) Origins in Product: How did Lenny make his way iunto the world of product management at Airbnb? What were some of his biggest takeaways from his time at Airbnb on product? What mistakes did he make on product at Airbnb? How did it impact his product thinking? 2.) Product Management: 101 How does Lenny define product management today? How is the role of PM changing? When is the right time to hire your first PM as a startup? What is the difference between Head of Product and CPO? When do you hire each? What are the biggest mistakes founders make when hiring their first product hires? 3.) The Hiring Process: How should founders breakdown the process of hiring for their first in product? What does the interview process look like? How should founders structure it? What core questions should teams ask of prospective candidates? What are red flags when interviewing potential product hires? 4.) The Onboarding Process: How should founders structure the onboarding process for new product hires? What can founders do to make PMs successful in their first 30 days? Where do many product hires make the biggest mistakes in the first 30 days? What can product hires do to build trust with their new team? Items Mentioned in Today's Episode with Lenny Rachitsky Lenny's Fave Book: The Mom Test

David Friedberg is Founder and CEO of The Production Board (TPB), a holding company established to solve the most fundamental problems that affect our planet, by reimagining global systems of production. Prior to founding The Production Board, David founded The Climate Corporation, a 10-year journey that culminated in their $930M acquisition by Monsanto. If that was not enough, David is the Founder and Chairman at Metromile and also sits on the board of Soylent, Clara Foods, Tillable, Cana Technologies and more. In Today’s Episode with David Friedberg You Will Learn: 1.) Origins: How David made his way into the world of startups and technology from academia and physics? What were David's biggest takeaways from scaling The Climate Corp to $930M exit to Monsanto? How did the exit put pressure on David for all future companies he builds? How does he manage that? 2.) The Macro: Venture + The Economy How does David foresee the impending rate hikes? What impact will this have on venture and the economy? What segment of the market will be first to be hit? Why is growth investing last to be hit? How does early stage play out in this very new environment? How will we see the velocity of capital deployment change in this new period? What does David believe are some of the crucial flaws of the venture model? How does David reflect on his own price sensitivity? What lessons has he learned from deals he has done or missed that have changed his perspective? 3.) David Frankel: The Business Builder What is David's rubrik for business value creation? How has this changed with time? How mentally plastic does one have to be around the time it takes to see margins, unit economics etc change from negative to positive? How does David and the team approach building new companies at TPB? Where do they find the founding teams? How do they incentivise them? How does TPB approach continuous funding for the companies they create? What milestones need to be hit? How do they assess them? How does David approach liquidity with regards to exits for the companies they create? Why does their holding company structure mean they have different incentives to VCs? 4.) David Friedberg: Father and Husband How does David reflect on his own relationship to money today? How has it changed over time? What have been David's biggest realisations on what provides him true happiness? How did having children change his operating mentality? What does being a great father mean to David? Item’s Mentioned In Today’s Episode with David Friedberg David’s Favourite Book: Zen Mind, Beginner's Mind

Sid Sijbrandij is the Co-founder & CEO @ GitLab. GitLab’s single application helps organizations deliver software faster and more efficiently while strengthening their security and compliance. Prior to their IPO last year, Sid raised funding from some of the best including ICONIQ, GV, Tiger, Coatue and D1 to name a few. Under his leadership, the company has grown to over 1,500 employees and over 30 million registered users. If that was not enough, Sid is also an active angel and sits on the board of Meltano, a spinout of Gitlab that allows you to manage all the data tools in your stack. In Today’s Episode with Sid Sijbrandij You Will Learn: 1.) The Founding of Gitlab: How did Sid make his way into the world of tech and startups? What was it about Gitlab as a project that excited Sid so much from Day 1? How did Sid convince his co-founder to turn Gitlab from a project into a company? 2.) The Future of Work: Why does Sid believe it is a fallacy that everyone will go back to the office? What are the 1-2 most important things for companies to do when moving to a remote work environment? Where does Sid see many make mistakes? What have Gitlab done to create a remote working environment so successfully? What have they tried that has not worked? What stage of company building does remote work best for? When is it most challenging? 3.) Sid: The Leader How has Sid changed and evolved as a leader over the Gitlab journey? How does Sid look to get as much feedback as possible on his leadership? How does Sid create an environment of safety where everyone feels they can provide feedback? How does Sid work with his CEO coach? Should every CEO have one? What should one look for in them? How do you know when you need to change your CEO coach? 4.) Sid: The Board Member: What have been Sid's biggest lessons on what makes successful board management? In prep for the meeting, what materials does Sid provide? When does he send them? Does he present to the board? What mistakes do founders make in boards? From being on the other side as a board member, what does Sid believe the best members do? What would Sid most like to change about board meetings today? Item’s Mentioned In Today’s Episode with Sid Sijbrandij Sid’s Favourite Book: High Output Management

Jeanne DeWitt Grosser is Head of Americas Revenue & Growth @ Stripe. In this role, Jeanne is responsible for all sales functions across the region including Sales Development, AEs, Solutions Architects, and many more. Jeanne also continues to spearhead Stripe's Enterprise strategy. Prior to this role, Jeanne was Stripe's Head of North America Sales where she built out Stripe's Acquisition Sales teams. Pre-Stripe, Jeanne was CRO @ Dialpad and also spent many years at Google in numerous different roles including most recently as Director of GSuite SMB & Mid-Market Sales, North America and LATAM. In Today’s Episode with Jeanne DeWitt Grosser You Will Learn: 1.) Entry into Sales: How did Jeanne make her way into her first sales job in tech? What did Jeanne learn from her many years at Google about how sales should interact with engineering? In hindsight, what would Jeanne have done differently/improved from her time with Dialpad? How did the role with Stripe come about? 2.) The Playbook: Does the founder need to be the one to create the sales playbook? When is the right time to bring in the first sales hire? Should they be a sales leader or rep? How does both the playbook and the type of sales hire change when hiring for a product-led-growth motion vs a traditional enterprise motion? What are the single biggest mistakes founders make when hiring their first in sales? 3.) The Hiring Process: How should founders structure the hiring process for their first sales hires? What did Dialpad do in the sales hiring process that worked well? How has Jeanne taken that to her hiring process at Stripe? What should be achieved or learned in each consecutive interview? How can founders use sales case studies most effectively? How can founders know if sales candidates truly have a strong grasp of the product? What are early signs of a 10x sales hire? What are red flags to look out for in the process? 4.) Sales Onboarding: What does the ideal onboarding process look like for new sales hires? What tasks and duties should all sales hires perform in the first 60 days? What are early signs that a new hire is not performing to the right standard? How does the first few months differ for sales reps when comparing a product-led-growth company to an enterprise company? What should sales leaders do to ensure that new hires engage with product and customer success efficiently?

Harley Finkelstein is the President of Shopify, the platform modern commerce is built on. Over the last 12 years, Harley has partnered with Tobi to the tune of building Shopify's revenue to over $4.6BN in 2021 and the team to over 10,000 employees. On the side, Harley is an Advisor to Felicis Ventures and in the past has held board seats at CBC, Omers Ventures and The C100. If that was not enough, you can see Harley on a screen near you as one of the “Dragons” on CBC’s Next Gen Den. In Today’s Episode with Harley Finkelstein You Will Learn: 1.) The Founding Story: What was Harley's first entrepreneurial endeavour? How did seeing his family lose everything impact Harley's mindset and ambition? How did Harley first meet Tobi @ Shopify? How did the Shopify journey begin? 2.) Leadership Lessons: How has Harley changed as a leader over the 13 years with Shopify? How does Harley embrace vulnerability and authenticity in his communication with the team? What is Harley most insecure about when he looks at leadership today? What have been some of the biggest lessons Harley has learned from his board on what great leadership is? 3.) The Art of Marriage: What does Harley believe makes the most successful marriage? Why have Harley and his wife been seeing a marriage therapist from the early days? What is the biggest mistake people make when communicating with partners? How has Harley changed as a husband over the years? 4.) The Joy of Fatherhood: Does Harley always believe he has been a good father? What was his realisation moment that he was not being the father he wanted to be? What core elements of his behaviour did he change? How did that impact his relationship with his kids? How does Harley ensure he performs at the highest level while also being there and being present for his family? Item’s Mentioned In Today’s Episode with Harley Finkelstein Harley’s Favourite Book: The Book of Ichigo Ichie: The Art of Making the Most of Every Moment, the Japanese Way

Scott Dietzen is Vice Chairman of the Board of Pure Storage and served as the Company’s CEO from 2010 to 2017. Under his leadership, Pure grew to thousands of employees and completed an IPO in 2015. Dietzen is a four-time successful entrepreneur with WebLogic, Zimbra, and Transarc. Before Pure, he was President and CTO of Zimbra (now part of VMware), but originally acquired by Yahoo!, where Dietzen served as interim SVP of Communications and Communities. Prior to Zimbra, Dietzen was CTO of BEA Systems, where he helped craft the technology and business strategy for WebLogic that drove BEA from $61m in annual revenues prior to the WebLogic acquisition to over $1B. In Today’s Episode with Scott Dietzen You Will Learn: 1.) The Journey to Pure Storage CEO: How did Scott make his way into the world of tech and startups? What was the hardest element of making the transition from CTO to CEO? What advice would Scott give to more technical leaders looking to make the move to CEO? Where do so many make mistakes? 2.) How To Build Trust in a Team: What are the most important ways that leaders can build trust with their teams? How can leaders be honest and share the hard truths without damaging role? What is the right tone to communicate both the big wins and big losses? Why does Scott always believe the losses teach more? How does Scott approach post-mortems? 3.) The Biggest Mistakes Founders Make: What are the single biggest hiring mistakes that founders make? What are the single biggest firing mistakes executives make? Why should founders sometimes say no to customers? How should founders approach investor selection and valuation for rounds? 4.) How to Optimise a Board: What specifically can founders do to optimise their board? What are the biggest errors founders make when communicating with their board? What is the value per word framework? How does it tell which board member is the best? Item’s Mentioned In Today’s Episode with Scott Dietzen Scott’s Favourite Book: The 22 Immutable Laws Of Marketing

Sahil Bloom is the Founding Partner @ SRB Ventures, a $10M fund that leverages the 500K followers Sahil has amassed to invest at the intersection of venture and media. Previously, Sahil spent 7 years at a large investment fund managing >$3.5 billion in capital and serves on the board of 4 companies. He has also been an active angel investor in over 30 companies. In Today’s Episode with Sahil Bloom You Will Learn: 1.) How Sahil made his way from a career in traditional finance to building a media company and leveraging that to raise the latest SRB fund? How does Sahil advise others is the best way to "find their zone of genius"? 2.) How To Build a Media Engine: What have been some of Sahil's biggest lessons on what works on Twiter and what does not work? What is the golden rule for Twitter? How does Sahil plan and come up with ideas for his Twitter threads? What tools and software does he use? How long does each thread take? 3.) The End of the Road for Traditional Venture: Why does Sahil think traditional venture is dying? What newcomers will take the place of the existing incumbents? Why does he think they are weak? What do new players provide that they do not? Which existing players will remain and be strong? Which will fade out? Does Sahil believe that VCs really provide any value? 4.) SRB Ventures: Why did Sahil decide to raise the new fund? How did he decide on size of the fund? What is the strategy? What is the portfolio construction? How does SRB provide media services others do not? How did Sahil meet Tim Cook and get him to invest in the fund? What is the biggest thing Sahil believes most people misunderstand about luck? Item’s Mentioned In Today’s Episode with Sahil Bloom Sahil’s Favourite Book: When Breath Becomes Air: Kalanithi Paul Sahil’s Most Recent Investment: Wander

Tiger Global are one of the most discussed venture firms on the planet. With a deal cadence and capital deployment speed that is unmatched, they have made their mark on the venture landscape like no other over the last 24 months. Today we are joined by leaders from Sequoia, Benchmark, Thrive Capital, General Atlantic, GGV and Aleph to discuss the rise of Tiger and how it impacts the venture ecosystem. In Today’s Episode on Tiger Global You Will Learn: 1.) Doug Leone: Sequoia Capital Why we need to change the words when use in venture? Why we need to get rid of "the game"? How does the rise of Tiger compare to the rise of prior entrants with the same approach? Why does Doug believe that the craft of venture will persist despite these new entrants? 2.) Bill Gurley: Benchmark Capital How does Bill analyse the change in late stage venture today? What are the main drivers of the increased competition in late stage venture? Why does Bill get concerned not by Tiger but how others respond to Tiger's model? How does Bill analyse the entry of hedge funds and PE funds into traditional venture models? 3.) Michael Eisenberg: Aleph How does Michael think about the "weaponisation of capital"? What are the significant benefits for a fund of having more capital than their competitors? How does this capital advantage change in boom and bust times? 4.) Anton Levy: General Atlantic Why does Anton believe that funds are leveraging their assets more efficiently than ever? How does Anton approach the mindset of AUM scaling without lowering returns? Why does Anton never want to compete on price? How does GA think about competing in a world of Tiger and hedge funds investing in tech? 5.) Hans Tung: GGV Why did Hans always believe the model to look at moving forward was Tiger? Why does Tiger's business model allow them structural and financial advantages over their competitors? What does Hans make of the data network effects of Tiger with their strategy? 6.) Kareem Zaki: Thrive Capital Why does Kareem think Tiger's approach makes absolute sense? Why does Kareem believe so many in venture like to try and discredit the Tiger model? How does Tiger's approach differ to Thrive's?

Max Rhodes is the Co-Founder and CEO @ Faire, the online marketplace where retailers discover their next bestsellers from independent brands across the globe. To date, Max has raised over $1.1BN with Faire from some of the best including Sequoia, Founders Fund, DST, Forerunner, Lightspeed and many more. Prior to starting Faire, Max spent close to 5 years at Square in numerous different roles including Director of Consumer Product at Caviar. In Today’s Episode with Max Rhodes You Will Learn: 1.) The Founding Story: How Max made his way into the world of startups with his joining an early Square team? How did his 5 years at Square impact how he approaches company building with Faire? How did Square's approach to product and mission impact Max's thinking? 2.) How To Hire Effectively: How does Max construct the hiring process? Where do many founders make mistakes? What does Max mean by "deep behavioural interview"? What questions does he ask? What are the signals of 10/10 candidates? What are red flags he looks for? How does Max determine capability? What literal tests can be done to test for this? 3.) How To Reference People: How does Max approach the referencing process when hiring people? How does Max make the other side feel comfortable, so they will open up and share everything? What have been some of Max's biggest lessons on what it takes to do referencing well? Where do many make mistakes with referencing? How does Max use an "out of 10" system to determine the quality of the candidate? 4.) How to Strategise: How does Max use strategy docs to orient the direction of the company? How often does Max write them? How long do they take to write? What are the core components of the strategy docs? Who else is involved in their writing? Once written, what is the right format to discuss with the team? How does Max approach how rigid he is to the strategies outlined? How does he determine whether he should change strategy or stick to plan? Item’s Mentioned In Today’s Episode with Max Rhodes Max’s Favourite Book: Good Strategy Bad Strategy, Who: The A Method for Hiring

Ed Baker is an angel investor and growth advisor to various startups including Lime, Zwift, Whoop, Crimson Education, GoPeer, and Playbook. Ed was the VP of Product and Growth at Uber from 2013-2017. Prior to Uber, Ed was the Head of International Growth at Facebook, a company he joined after they acquired a startup he co-founded called Friend.ly, which had grown to over 25 million users. In Today’s Episode with Ed Baker You Will Learn: 1.) Ed Baker: Entry into Growth: How Ed made his way into the world of growth from his start founding a dating site while at Harvard? How he made his way to lead international growth at Facebook? How his time with Facebook led to his joing Uber to start Uber's growth team? What were Ed's biggest lessons from Uber and Facebook? How did his approach to growth and mindset change as a result of his time there? 2.) When is the Right Time: When is the right time for startups to hire their first growth leads or reps? How should they determine whether to promote from within or hire externally? What are the biggest mistakes startups make on the timing of this hire? How can startups accurately assess whether they have product-market-fit? 3.) Who To Hire: Step by step, how does Ed structure the interview process for all new growth hires? What are the must ask questions for growth leaders to ask candidates in interviews? What are the clear signs and answers that suggest a 10x growth hire? What literal tests does Ed do to determine the quality of a hire? How do the best perform? 4.) Onboarding and Integration: What is the optimal onboarding process for all new growth hires? How do the best growth hires start in the first 60 days? What do they achieve? What are some of the early signs that a growth hire is not working out? How should the relationship be between the CEO and the Head of Growth? How can the Head of Growth foster a strong relationship between growth and product teams?

Geoff Lewis is the Founder and Managing Partner @ Bedrock, now with over $1BN in AUM, Bedrock invests in breakout technology companies that are incongruent with popular narratives. In the past, Geoff has backed some generational defining companies such as Wish, Lyft, Nubank, RigUp, Vercel, Anduril and many more. Prior to founding Bedrock, Geoff was a Partner @ Founders Fund. In Today’s Episode with Geoff Lewis You Will Learn: 1.) How Geoff made his way into the world of venture with his joining Founders Fund? How his time with Founders Fund led to his co-founding Bedrock with Eric? 2.) Geoff Lewis: The Investor: How does Geoff reflect on his own relationship to price? How does he determine when to pay up vs walk away? How does Geoff approach the re-investment decision-making process? Where do most go wrong when it comes to allocating reserves? What have been some of Geoff's biggest misses? How did they impact his investing mindset? Why does Geoff not believe that ownership is as crucial as other VCs suggest? 3.) Bedrock: The Firm What have been some of the biggest challenges in building Bedrock? Where does Geoff believe many firms make core mistakes in firm building? What are the differences between principles and rules? Why does Geoff believe all firms need to have principles? How does Geoff approach internal talent building? What are the signals of people that will succeed in venture? How do they approach learning? 4.) The Market: How does Geoff analyse the current state of the venture market? Does Geoff agree with the notion of "play the game on the field"? Why does Geoff think markups are BS and just VCs looking for external validation? How has Geoff learned to isolate from the VC community and retain that purity of mindset working with great entrepreneurs? Item’s Mentioned In Today’s Episode with Geoff Lewis Geoff’s Favourite Book: Friedrich Nietzsche Geoff’s Most Recent Investment: Praxis

Aaron Levie is the Founder and CEO @ Box, the company incorporating the best of secure content collaboration with an intuitive user experience suited to the way people work today. Prior to their IPO in 2015, Aaron raised from some of the best in the business including the main man Mark Cuban, a16z, Emergence, DST, Coatue, DFJ and many more. Aaron founded the company from his dorm room at the University of Southern California and has led the company to 1,900 employees and over $770M in revenue, as of 2021 data. In Today’s Episode with Aaron Levie You Will Learn: 1.) How Aaron founded Box from his dorm room at the University of Southern California? What was that founding a-ha moment? What did the first year look like? Does Aaron agree, "serial entrepreneurship is overrated"? 2.) Phases of Leadership and Company Growth: How does Aaron define the different phases of leadership required as a company grows? Which phase did Aaron find the most challenging? How did he overcome it? What are the first things to break when companies grow? What can founders do to prevent this? Does Aaron agree, "the best CEOs are the best resource allocators"? 3.) The Market: How does Aaron thinkj about the dislocation between private company valuations and public company market caps? What does Aaron believe are the biggest challenges founders face when they are over-capitalised? What does Aaron mean when he says, "raise when cash is cheap, spend as if it was expensive"? How does Aaron advise founders on fundraising today? 4.) The Team and Culture: How does Aaron create a safe space where all team members can come to him with anything? How does Aaron approach effective goal setting? How does one balance between achieveable and also aggressive goals? How does Aaron approach the art of delegation? What is his decision-making framework for what to delegate vs what to control? Item’s Mentioned In Today’s Episode with Aaron Levie Aaron’s Favourite Book: Innovator's Dilemma: When New Technologies Cause Great Firms to Fail (Management of Innovation and Change)

Scott Belsky is an entrepreneur, author, investor, and currently serves as Adobe’s Chief Product Officer and Executive Vice President, Creative Cloud. Scott oversees all of product and engineering for Creative Cloud, as well as design for Adobe. In 2006, Scott founded Behance, the leading online platform for the creative industry, and served as CEO until Adobe acquired Behance in 2012. Behance now has over 25M members. Scott is also an early advisor and investor in Pinterest, Uber, Sweetgreen, Carta, Flexport, Airtable, and several others. Finally, if that was not enough, Scott is the author of two national bestselling books - Making Ideas Happen and The Messy Middle. In Today’s Episode with Scott Belsky You Will Learn: 1.) Narrow the Focus, Increase the Quality: What does Scott believe is the core challenge in product? What was the single biggest product challenge Scott faced at Behance? How did they overcome it? When should product teams listen to customer feedback vs ignore it? What are the core questions product teams should ask user groups to extract the most feedback and value? 2.) The Importance of the First Mile: What does Scott believe makes a great first mile when it comes to the product experience? Where do so many companies go wrong in creating the first mile user experience? Which company at scale has retained this simplicity of the first mile? How did they do it? What does Scott mean when he says, "the devil is in the defaults"? What can product teams learn from this? 3.) The Makings of a Great Product Leader: What are the 3 core questions every great product leader should ask on every screen? How do the best product leaders structure product reviews? Who is invited to product reviews? How often are they? Who sets the agenda? When is it sent? What do the best product leaders do to retain direction and productivity in reviews when there are many people and many ideas? How do they stay on track? 4.) The Hirings of a Great Product Team: How can founders know whether to hire the product leader or retain the role? When is the right time? What are the single biggest mistakes founders make when hiring their first product hires? How should founders structure the hiring process for product hires? What should they look to gain from each interview? What are the must ask questions in those interviews? How do the best respond? What case studies or physical tests can be done to determine the quality of a candidate?

David Frankel is a Co-Founder and Managing Partner @ Founder Collective, one of the great seed firms of the last decade with a portfolio including Uber, Coupang, Airtable, Whoop and many more incredible companies. Previously, David was Co-Founder and CEO of Internet Solutions (IS), the largest ISP in Africa, ultimately acquired by NTT. David is also a founding board member of Endeavor SA and in the past has been selected by the World Economic Forum for the Global Leader of Tomorrow (GLT) program. In Today’s Episode with David Frankel You Will Learn: 1.) How David made his way into the world of angel investing? How his mindset changed when making the transition from angel to an institutional investor with the founding of Founder Collective? 2.) Building the Firm: Founder Collective What are the biggest challenges in venture firm building today? Why is "deploy" and "the game" banned as words within Founder Collective? What terms are promoted as an alternative? How does David construct investment decision-making in the partnership? How does David create a safe space where all team members can share their thoughts in a non-judgemental, safe environment? What are the biggest mistakes or challenges that David sees firms make when building? 3.) David Frankel: Investor Mindset How does David analyse the current seed market today? What does he like? What worries him? Does David agree that early stage investing has never been less collaborative? How does David reflect on his own relationship to price today? How does he determine when to pay up vs when not to? How does David think about the compression on fund deployment timelines? Will this change? How does David keep a fresh and clean mind when viewing new opportunities, having seen many work and not work? How does one retain that mental purity when investing? What have been some of David's biggest misses? How did it impact his style of investing? 4.) The Partnership: What was the most recent disagreement David had with the partnership? How was it resolved? How does David approach self-doubt and insecurity within the partnership? How can this be managed successfully? What have been some of David's biggest lessons on how to give effective feedback without being judgemental? In a world of Zoom, how did the partnership retain the same level and quality of connection that they had in person? What works? What does not work? Item’s Mentioned In Today’s Episode with David Frankel David’s Favourite Book: The Code Breaker: Jennifer Doudna, Gene Editing, and the Future of the Human Race David's Most Recent Investment: PairTree

Mark Cuban is a serial entrepreneur, investor, and owner of the Dallas Mavericks. Today we are focused on Mark's latest entrepreneurial endeavor, starting Mark Cuban's Cost Plus Drug Company, the online pharmacy taking out the middlemen, meaning no price games and huge drug savings. As mentioned, Mark is also the proud owner of Dallas Mavericks, since his taking over they have competed in the NBA Finals for the first time in franchise history in 2006 – and became NBA World Champions in 2011. Before Dallas Mavericks, Mark co-founded Broadcast.com – streaming audio over the internet. In just four short years, Broadcast.com (then Audionet) was sold to Yahoo for $5.6 billion dollars. If that was not enough, Mark is also one of ABC’s “Sharks” on the hit show Shark Tank. In Today’s Episode with Mark Cuban You Will Learn: 1.) Cost Plus Drugs: Origin Why Mark decided to build Cost Plus Drugs? Why has no one done it before? How does Mark think about resource and time allocation with Cost Plus? 2.) Building the Team: Hiring How does mark analyze his approach to hiring? Where is he weak? Where is he strong? What one motto does Mark always use when it comes to hiring? What is the most common mistake Mark sees founders make when it comes to team build? How does Mark identify stress removers? What are the core signals? 3.) Brand + Capital + Business Strategy: Why is the current cost structure of healthcare so damaged in the US? How does Cost Plus change this? How does Mark think about what it takes to build great brand today? Why will Cost Plus not be doing big TV and traditional media advertising? What types of guerilla marketing is Mark most excited by? Why will Mark never have a billboard in Times Square? 4.) AMA with Mark Cuban: What 3 traits does Mark most want his children to adopt? What worries Mark most today? What are Mark's biggest strengths? What are his biggest weaknesses? What single purchase has brought Mark the greatest joy?

Dannie Herzberg is a Partner @ Sequoia Capital and one of the great sales leaders of the last decade. Prior to entering the world of venture, Dannie spent 4 years at Slack as their Head of Enterprise Sales, there Dannie built & scaled the self-serve / SMB, mid-market, and enterprise sales orgs across the Americas as Slack grew from $100M - $1B in revenue. Before Slack, Dannie spent over 5 years at Hubspot building sales, opening an SF office, and then joining product to launch CRM & platform. In Today’s Episode with Dannie Herzberg You Will Learn: 1.) How Dannie got her first job in sales at Hubspot through being a waitress in a Boston Diner? What were her biggest lessons from her 5 years scaling sales at Hubspot? How did Dannie's 4 years at Slack impact her operating and sales mindset today? 2.) The Playbook: Does the founder need to be the one to create the sales playbook? When is the right time to bring in the first sales hire? Should they be a sales leader or rep? When is the right time to bring in a CRO, sales enablement and revenue ops? What are the single biggest mistakes founders make when hiring their first in sales? 3.) The Hiring Process: How should founders structure the hiring process for their first sales hires? What should be achieved or learned in each consecutive interview? How can founders use sales case studies most effectively? What are early signs of a 10x sales hire? What are red flags to look out for in the process? 4.) Sales Onboarding: What does the ideal onboarding process look like for new sales hires? What tasks and duties should all sales hires perform in the first 60 days? What are early signs that a new hire is not performing to the right standard? How does the first few months differ for sales reps when comparing a product-led-growth company to an enterprise company? How can new sales hires really engage with broader functions within the team in the first 30 days? Item’s Mentioned In Today’s Episode with Dannie Herzberg Inbound Marketing, Revised and Updated: Attract, Engage, and Delight Customers Online

Roger Ehrenberg is a Founding Partner @ IA Ventures, one of the most successful seed funds of the last decade with $475 million across their four funds. Previous investments include The Trade Desk, Datadog, Digital Ocean, Wise and Recorded Future. Most recently, Roger took a step away from the day-to-day running of the firm, since he started IA Sports Partners, investing in sports franchises and other sports-related assets. Last month, Roger, alongside his two sons, started Eberg Capital, an investment vehicle focused on web3, crypto, NFTs and next-gen infrastructure. In Today’s Episode with Roger Ehrenberg You Will Learn: 1.) How Roger made his way into the world of angel investing and venture having had a successful career on Wall St? How did seeing the booms and busts of the dot com and 2008 impact his investing mindset today? How does today compare to those times? 2.) The Investor Mindset: What is Roger's #1 rule when it comes to managing investor psychology in volatile times? What does Roger do to calm his mind and prevent worry and fear when markets crash? What works? What does not work? How does one assess how close we are to the bottom? Why does Roger believe there is more "blood on the streets to come"? When does Roger believe is the right time to pullback vs when to be aggressive in deployment? What company profiles will do well vs poorly moving into this new cycle? 3.) Investing Strategy: How does this new market impact the three different investing categories; early, Series A & B and growth? Why does Roger believe deployment timelines will be extended? How will pricing be impacted? Why does Roger believe that the Series A & B crunch is the most worrisome? How will their bar for what makes a great company change? Should early stage managers alter their reserves strategy in the face of more stringent Series A rounds? Why does it not make sense to invest in "pay to play" rounds? How does Roger adivse the companies that he works with today on burn vs growth? 4.) AMA: How does Roger evaluate his own relationship to money today? How has it changed over time? What does Roger believes makes a truly successful marriage? What can one do to foster extreme trust and safety in a marriage? What does Roger believe have been some of the biggest insecurities he has had to overcome over the last decade? How did he overcome them? Item’s Mentioned In Today’s Episode with Roger Ehrenberg RIP Good Times by Sequoia Capital

Scott Sandell is the Managing General Partner of NEA, one of the leading firms of the last 3 decades with now close to $24Bn under management and a portfolio including Salesforce, Robinhood, Plaid, Databricks and more. As for Scott, since joining the firm in 1996 he has led investments in Salesforce.com, Tableau Software, WebEx and Workday and serves on the board of Robinhood, Cloudflare, Coursera and Divvy to name a few.  Rick Yang is a General Partner and Head of Consumer Investing @ NEA, since joining in 2007 he has led investments in the likes of Masterclass, Plaid, Robinhood and many more. In Today’s Episode with Scott Sandell and Rick Yang You Will Learn: 1.) How Rick came to meet Vlad, Robinhood Founder, for the first time? What impressed Rick most in that first meeting? How did the internal discussions proceed at NEA? Was it a unanimous decision to make the investment? 2.) The Market: How did Rick and Scott evaluate the market at the time? Bottoms up, top down? How did the market change and evolve both in ways they did and did not expect? How do Rick and Scott evaluate market timing risk today when investing? How did Rick and Scott approach outcome scenario planning with Robinhood? 3.) The Traction: What core signals and datapoints made Rick realise Robinhood had product-market-fit? How did Rick and NEA analyse Robinhood's early organic customer acquisition? How did the board advise on how to spend their first marketing dollars? How does the cost structure of the business compare to Charles Swaab and eTrade? Why is Robinhood such a superior model? 4.) The Team:  How has Vlad evolved and developed as a leader over time? How did Vlad handle the 36 hours in Feb 2021 when he had to go and raise $3BN+? Who is the unsung hero of the Robinhood team? What have they done to deserve this?

Jonathan Neman is Co-Founder & CEO of Sweetgreen, the mission-driven restaurant brand that serves healthy food at scale. Alongside his co-founders, Jon has scaled Sweetgreen from one small restaurant to one of the US' leading food brands with over 5,000 employees, over 140 locations and $300M+ in revenue. If that was not enough, Jon is also an active board member of MeUndies. In Today’s Episode with Jonathan Neman You Will Learn: 1.) How Jon took the decision to leave his "dream job" as a consultant at Bain to start Sweetgreen? What did his Bain boss tell him that persuaded Jon it was the right decision to leave? How does Jon think about and advise people when it comes to choosing the safe vs the risky path? 2.) How Sweetgreen was not an Overnight Success: At what moment did Jon really not think that Sweetgreen would make it? Why? How did he deal with those moments of intense stress and pressure? How does Jon test for true grit and resilience both in hires and in founders today? 3.) Brand + Capital + Business Strategy: How does Jon think deeply about what brand means today? What did Sweetgreen do right when it comes to their brand building? How did they marry art and science in the right way? What do the unit economics look like on a per store basis? What is the payback period on a per store basis? How has this changed over time? How does the store design impact the profit per store? How has store design changed over time? What have been some of the biggest lessons in terms of when, where and how to open new stores? 4.) Leading Through COVID: What were some of Jon's biggest lessons from leading a consumer brand through COVID What were some of the toughest elements for Jon? How did he overcome them? How can founders bring people along with their thought process and inspire? Who is Jon's biggest mentor? What has he learned from them? Item’s Mentioned In Today’s Episode with Jonathan Neman Jon’s Favourite Book: Thinking, Fast and Slow: Daniel Kahneman

Anne Wojcicki is the Founder & CEO @ 23andme, offering DNA testing with the most comprehensive ancestry breakdown, personalized health insights, and more. To date, Anne has raised over $1BN for the company from the likes of Sequoia, GV, NEA and many more incredible names. Prior to founding 23andMe, Anne spent a decade on Wall Street investing in healthcare and felt frustrated by a system built around monetizing illness instead of incentivizing prevention. If that was not enough, Anne is also on the board of Cazoo and The Anne Wojcicki Foundation and is an active angel investor with investments in the likes of Embark and Maven Clinic. In Today’s Episode with Anne Wojcicki You Will Learn: 1.) How Anne made her way from Wall St healthcare investing to founding one of the leading healthcare companies of the last decade in 23andme? 2.) Trust and Friendship: How does Anne determine whether someone is genuine or is being transactional? What are the signs? How does Anne approach trust in relationships? Start from a base of full trust and it is to be lost or start with none and it is to be gained? What does Anne believe are the core of the best and most healthy relationships she has? 3.) Leadership: How does Anne reflect on her own decision-making processes today? How does Anne create a safe space where her team feel they can pushback on her and tell her how they feel? How does Anne approach internal role migration? What does Anne do to get the very best out of her team? How has Anne's leadership style changed over the years? How has being on the board of Cazoo changed how Anne reflects on her own board leadership? What have been some of her biggest lessons from Alex Chesterman? 4.) AMA: What is the hardest element of Anne's role with 23andme? What is Anne's morning routine? What 3 traits would Anne most want her children to have? Anne can have a billboard anywhere, what do it say on it and why? What would Anne most like to change in the world of healthcare over the next decade?  

Ali Partovi is the CEO @ Neo, a mentorship community and communal VC fund that announced their new $150M fund last year on the back of early hits from Fund I including Vanta and Kalshi. As an angel, Ali has made personal investments in Dropbox, Uber, Airbnb, Facebook, Convoy and many more. Prior to investing, Ali founded 2 companies, the first; LinkExchange which he sold to Microsoft for $265M in 1998 and the second, iLike which was acquired by Microsoft in 2009. In Today’s Episode with Ali Partovi You Will Learn: 1.) How Ali made his way into the world of startups with the founding of his first company? How Ali made his way into angel investing and then starting and raising Neo, as a fund? 2.) How To Kill a $125M By Being Too Honest: How did Ali lose this $125M with Jerry Yang and Yahoo? What led Ali to believe that Paul Graham was so special in 1995? What would Ali have done differently with the benefit of hindsight? How does Ali feel about investment misses today? What are his biggest misses? How has it impacted his mindset and approach to investing? 3.) The Meeting with Steve Jobs Did Not Go Well: Why did the meeting with Steve Jobs not go well? What was wrong with the way Ali phrased his final statement? What did this teach Ali about how founders should communicate the difference between hype and reality? What did this experience teach Ali about how founders should run both fundraising and M&A processes? How does Ali build trust with every touchpoint? 4.) U2, Airbnb and Google at Seed: How did Bono come to save the day for Ali for his startup in 2009? What did this teach Ali about how to frame risk and when to go all in vs hold back? How did Ali miss investing in the seed for Airbnb? How did he make up for it with a later investment? How did Ali come to miss investing in the Google seed round? Does FOMO haunt Ali today? Item’s Mentioned In Today’s Episode with Ali Partovi Ali’s Favourite Book: Sapiens: A Brief History of Humankind

Rob Schutz is Chief Growth Officer and Co-founder at Ro, the healthcare technology company building a patient-centric healthcare system. To date, Ro has raised over $870M with a last reported valuation of $5BN and under Rob’s growth leadership, Ro has become one of the fastest-growing companies in the country. Prior to Ro, Rob was VP of Growth at Bark, the makers of BarkBox, and helped scale revenue from zero to $100 million. He also founded a Washington DC-based daily deals site that was acquired by kgbdeals in 2011. In Today’s Episode with Rob Schutz You Will Learn: 1.) How Rob made his way into startups and growth through the world of daily deals? How that led to his leading growth for Bark and ultimately founding Ro? How did leading marketing for Bark impact his growth strategy today with Ro? 2.) What is "Growth" and When to Hire For It: How does Rob define "growth and "Head of Growth"? When is the right time to start thinking about a growth team? Should founders hire a "Head of Growth" first or hire younger growth reps? Where should the growth team sit within the organization? 3.) How to Hire Growth Leader and Reps: What is the step-by-step process to hire growth leaders and reps? How does it differ when hiring growth leaders vs reps? What questions does Rob always ask? What separates good from great answers? What case studies does Rob like to use to determine candidate quality? How can one tell whether marketeers and growth candidates truly understand data? 4.) How to Structure the Onboarding Process: What does the optimal onboarding process look like for new hires? What tasks and duties do you expect reps and growth leaders to complete in the first month?  What are some early red flags that the candidate you have is not good enough? How can leaders deliberately manufacture moments for growth teams to interact with other teams? What are the biggest mistakes growth teams and leaders make in the early days?

Frank Slootman currently serves as Chairman and CEO at Snowflake and has over 25 years of experience as an entrepreneur and executive in the enterprise software industry. Prior to Snowflake, Frank served as CEO and President of ServiceNow taking the company from around $100M in revenue, through an IPO, to $1.4B. Before ServiceNow, Frank served as President of the Backup Recovery Systems Division at EMC following the acquisition of Data Domain Corporation/Data Domain, Inc., where he served as the CEO and President, leading the company through an IPO to its acquisition by EMC for $2.4B. You must check out Frank's book, Amp It Up. It can already be pre-ordered here. In Today’s Episode with Frank Slootman You Will Learn: 1.) Narrow the Focus, Increase the Quality: How does Frank determine what to focus on? What does the prioritisation process look like? What one question does Frank ask his team to ensure they are focused? What are the best answers? What are the worst? When should you change focus? 2.) When There is Doubt, There is No Doubt: What does Frank mean by this? What does it apply to? When is there nuance? How long does Frank give people who are underperforming? How does he communicate their underperformance to them directly but productively? What is the right way to fire someone? Why are performance reviews BS? 3.) Make The Good People Great: How does Frank get the very best out of his teams? How does he make the good great? How does he use compensation and equity structures to supercharge his teams? How does Frank set stretch targets that are both ambitious but also attainable? 4.) The Art of Leadership and Board Management: Why does Frank believe every CEO should be anxious? How has Frank changed as a leader over time? What is the biggest mistake founders make when it comes to board management? How can founders actively manage and control their board? Item’s Mentioned In Today’s Episode with Frank Slootman Frank’s Favourite Book: Courage Is Calling: Fortune Favours the Brave, The Speed of Trust: The One Thing that Changes Everything

Devin Finzer is the Founder & CEO @ Opensea, the world's first and largest NFT marketplace allowing you to discover, collect, and sell extraordinary NFTs. To date, Devin has raised over $423M for the company with their last $300M round valuing Opensea at $13.3BN. Before changing the world of NFTs, Devin co-founded ClaimDog which was acquired by Credit Karma and before founding ClaimDog, Devin was an engineer at Pinterest. Do want to say, I always love Semil Shah's startup of the year, for 2021 it was Opensea, check out his piece here. In Today’s Episode with Devin Finzer You Will Learn: 1.) How Devin made his way into the world of NFTs and came to found the first and largest NFT marketplace in the form of Opensea? 2.) The Scaling Story: What were the first early signs that Opensea was working when they were in YC? What core metrics did they look at to determine success? Given NFTs not being "hot" at the time, how was the fundraising process for Opensea coming out of YC? What were the early investors most excited about? What was the inflection point when Opensea and NFTs really started to take off? What most surprised Devin about the way in which the inflection point happened? When scaling from $150M to $4BN in GMV, what are the first things to break in a company? How does Devin maintain company morale with such volatile crypto and NFT markets? 3.) The Next Decade of NFTs: How does Devin predict large brands and companies will utilise NFTs for their businesses? In what ways does Devin think creators and celebrities will use NFTs moving forward to create more efficient business models? How does Devin respond to the statement, "NFTs do more to harm than help income inequality?" What are Devin's biggest concerns moving forward when analysing the NFT market? How does Devin see the future for the development and experimentation of NFTs? 4.) The Future of NFT & Gaming: How does Devin see NFTs impacting the world of gaming most? How does Devin think about interacting with these gaming communities that are external to the centralised Opensea marketplace? Item’s Mentioned In Today’s Episode with Devin Finzer Devin’s Favourite Book: Homo Deus: A Brief History of Tomorrow

Ralf Wenzel is the Founder & CEO @ JOKR, a global platform for instant retail delivery at a hyper-local scale serving both the US and LATAM. Ralf has raised over $260M for the company, most recently valuing it at $1.2BN. Prior to JOKR, Ralf spent 7 years as the Founder & CEO @ foodpanda, as well as, enjoying roles as Chief Strategy Officer @ Delivery Hero, Interim Chief Product and Experience Officer @ WeWork and even moving to the other side of the table as a Managing Partner with Softbank. In Today’s Episode with Ralf Wenzel You Will Learn: 1.) What is the unit economic breakdown for quick commerce business models? What levers can be used to improve it over time? 2.) Comparing the US to LATAM: What is the AOV (average order value) in the US vs LATAM? What is the order frequency in the US vs LATAM? How does labour cost vary when comparing LATAM to the US? How does real estate cost for fulfilment centres differ when comparing LATAM to the US? How do product margins on a per product basis differ when comparing US to LATAM? 3.) New Market Growth and Maturation: What is the payback period for new markets? How has this changed over time? How does the payback period reduce with every new market being opened? What % of AOV is spent on marketing when a new market is opened? How does this marketing spend change over time? In mature markets, how much new customer acquisition is organic vs paid? What is the average weekly growth rate in new vs mature markets? 4.) Business Model Expansions: How does Ralf and JOKR approach the potential for private label goods? How does private label change the margin structure of the goods? What have been their lessons from starting their first private label goods? How does Ralf approach the ability to integrate advertising and paid search? What is needed for paid search and advertising to be a meaningful part of the business?

Mark Carney is Vice Chair of Brookfield Asset Management and Head of Transition Investing. Prior to Brookfield, Mark served as the Governor of the Bank of England from 2013 to 2020, and prior to that as Governor of the Bank of Canada from 2008 until 2013. Mark was also Chairman of the Financial Stability Board from 2011 to 2018. Mark is a long-time and well-known advocate for sustainability and is currently the United Nations Special Envoy for Climate Action and Finance. If that was not enough, Mark serves on numerous other boards including Stripe, Bloomberg Philanthropies and the Foundation Board of the World Economic Forum to name a few. In Today’s Episode with Mark Carney You Will Learn: 1.) How Mark made his entrance into the world of finance and came to the role of Governor of the Bank of Canada? How did that role lead to his becoming Governor of the Bank of England? How did seeing multiple booms and busts impact Mark's investing mindset? 2.) Governments, Central Banks and Regulation: How do governments and central banks retain control in a completely decentralized financial world? Can traditional currencies and digital currencies peacefully co-exist? What are Mark's predictions for central bank digital currencies? How does Mark expect governments and central banks to regulate digital currencies in the coming years? 3.) The Winners and Losers: What does the future hold for crypto exchanges? How do competitors for digital gold perform? Why does Mark believe in crypto "only the niche will survive"? What does the rise of Defi mean for traditional banks? What will determine those that survive? What does Mark mean when he says the winners will decide "what is my interface with this crypto world?'' 4.) The Future of NFTs: Do NFTs do more to help or to harm income inequality? How does Mark see the future for the development and experimentation of NFTs? Who are the winners and losers in the next decade for NFTs? How does Mark feel about the pause between productivity gains and real wage benefits that exist today?  Item’s Mentioned In Today’s Episode with Mark Carney Mark’s Favourite Book: Arcadia by Tom Stoppard

Will Ahmed is the Founder and CEO @ Whoop, the company on a mission to unlock human performance with their wearable device that is your digital fitness and health coach. To date, Will has raised over $400M for the company with the last round valuing Whoop at $3.6BN and with a cap table including the likes of Softbank, Accomplice, Founder Collective, Foundry Group, IVP and more. In Today’s Episode with Will Ahmed You Will Learn: 1.) How Will went from being a professional athlete and college student to founding one of the hottest startups in fitness and healthcare? What are the similarities and differences of being an athlete and being a CEO? 2.) What does Will mean when he says, "there is value in the struggle early on"? How does Will advise founders on when to give up vs when to stay the course? If Will had not struggled with funding in the early days, would the Whoop journey be different? How does Will advise founders when it comes to taking funding when it is on the table? What are the nuances to this? 3.) In what way does Will believe "realism is overrated"? When does Will believe it is good to be realistic? In what ways can it be good to be idealistic? How did Will get some of the largest sports stars on the planet to use Whoop in the early days? Why did Will always refuse to pay sports stars to use Whoop? What were the benefits of doing this? 4.) How does Will define high performance? Why does Will believe it is crucial for leaders to disassociate their own personal feelings from the progress of their company? What advice does Will give to leaders in an attempt to do this? What has Will done to be a better CEO in the last year? What does Will believe are his biggest weaknesses as a CEO?  Item’s Mentioned In Today’s Episode with Will Ahmed Will’s Favourite Book: Shoe Dog: A Memoir by the Creator of NIKE

Bangaly Kaba is the Head of Platform Growth @ Popshop Live, a live streaming mobile marketplace that combines commerce, entertainment, and social. Prior to Popshop, Bangaly led the product growth and consumer product orgs at Instacart and before Instacart was Head of Growth @ Instagram, where he built and led the product team that helped grow Instagram from 440M to > 1B monthly actives in 2.5yrs. If all of this was not enough, Bangaly has also spent time investing as a Sequoia Scout having made investments into Career Karma, Binti.com and Squad App to name a few. In Today’s Episode with Bangaly Kaba You Will Learn: 1.) How Bangaly made his way into the world of growth and came to lead some of the largest growth orgs in tech at the likes of Instacart and Instagram? 2.) How does Bangaly define the rule of "Head of Growth"? When is the right time for founders to start hiring a growth leader? How do they know whether to hire a growth leader or junior growth reps? Where should founders place these first growth hires in the org? Product or marketing? 3.) How would Bangaly structure the hiring process for any growth hire? What are the must-ask questions? What case studies would Bangaly ask all candidates to complete? What are the signals of a 10x growth hire? What are some core red flags that show in the interview process? 4.) What does the ideal onboarding process look like for new growth hires? What are the signs that a new growth hire is hitting target and expectations? What are some early warning signs that a growth hire is not meeting expectations?   5.) What is the ideal relationship between the Head of Growth and the CEO? How often should they meet? How should they structure the discussion? How should the growth team work with product teams to be successful? How should growth teams work with marketing teams?

John Doerr is an engineer, venture capitalist, the chairman of Kleiner Perkins, and the author of the #1 New York Times best-seller Measure What Matters. For over 40 years, John has helped build some of the most generational defining companies of our generation. He was an original investor and board member at Google and Amazon, helping to create more than a million jobs. A pioneer of Silicon Valley’s cleantech movement, John has invested in zero emissions technologies since 2006. Check out his latest book, Speed & Scale: An Action Plan for Solving Our Climate Crisis Now. In Today’s Episode with John Doerr You Will Learn: 1.) What was John's entry into climate change investing? Having backed the likes of Amazon and Google, why did John decide then was the right time to do a climate fund, a pandemic fund, an iPhone fund? How does John think about market timing risk today? How does John determine between risks he is vs is not willing to take? 2.) What was one of John's biggest lessons on risk and upside from working alongside Tom Perkins? How did the Google deal come together? Where did John first meet Larry and Serge? What convinced John to write them a $12M check for 12% of the company? Why was it a contested deal within the partnership? How did the discussion go internally? 3.) Why and how is climate innovating and investing different today than it was in 2008? What are the core OKR's laid out in the book, that we need to achieve as a society? Why does John believe that governments are the biggest problem to us achieving these objectives? What does John mean when he says, "I am hopeful but not optimistic"? 4.) What does truly great listening mean to John? How would John describe his style of board membership? What do the truly special board members do? What does John do that makes him often cited as one of the best at recruiting? What is John's biggest investing miss? How did it change his mindset and approach? What investment is John most proud of, that no one knows?  Item’s Mentioned In Today’s Episode with John Doerr John’s Favourite Book: How to Avoid a Climate Disaster: The Solutions We Have and the Breakthroughs We Need

Kyle Parrish is VP Sales @ Figma, the company that connects everyone in the design process so teams can deliver better products, faster. At Figma, Kyle built the sales engine from scratch to today, with over 100 incredible people in sales. Before Figma, Kyle spent over 5 years at Dropbox in numerous different roles including Head of Sales, where he scaled the Austin, Texas office from 3 to over 80 people to Global Partnerships lead, where he was responsible for growing Dropbox’s partner ecosystem. In Today’s Episode with Kyle Parrish You Will Learn: 1.) How Kyle first made his way into the world of sales and came to be one of the 3 performing sales reps in a 300+ sales team? How that led to his joining the hypergrowth journey of Dropbox? What led Kyle to make the move from Dropbox to the rocketship that is Figma? 2.) When and Who: Does the founder need to be the person to create the sales playbook? How can a founder know whether it is right to hire sales reps or a Head of Sales first? In terms of ARR, is there a time when you have to have a Head of Sales? Does Kyle agree with Jason Lemkin in terms of bringing in reps, two at a time? Where do founders make the biggest mistakes when it comes to the timing of these hires? 3.) How To Know and Test: What non-obvious characteristics do 10x sales hires have? What questions or case studies does Kyle find to be most revealing in identifying these non-obvious traits? How should founders structure the process for new reps and a Head of Sales? Meeting by meeting, what should we look to achieve? 4.) Setting Up for Success: What does the ideal onboarding process look like for new sales reps? What tasks and processes would Kyle expect new reps to complete within the first month or two on the job? What are the clearest signs of a new rep hire not working out? How should founders approach 1-1 and 360 reviews with their new reps?   5.) Working Together: What is the ideal relationship between the founder and the new Head of Sales? How often should they meet? What should the founder expect from the new Head of Sales? How should the Head of Sales work with the Head of Marketing most efficiently? Item’s Mentioned In Today’s Episode with Kyle Parrish Kyle's Favourite Sales Blog Post: The Sales Learning Curve

Bill Gurley is a General Partner @ Benchmark, one of the most successful funds of the last decade with a portfolio including Uber, Twitter, Dropbox, Modern Treasury, Snapchat, StitchFix, and many more. As for Bill, widely recognized as one of the greats in venture having worked with GrubHub, NextDoor, Uber, OpenTable, Stitch Fix, and Zillow. Prior to Benchmark, Bill was a partner with Hummer Winblad Venture Partners. Michael Eisenberg spent 15 years as a General Partner @ Benchmark working alongside Bill and the Benchmark partnership. Following Benchmark, Michael co-founded Aleph, one of the leading Israeli venture funds of the last decade with a portfolio including Lemonade, Melio, and HoneyBook, just to name a couple of Aleph's unicorns. In Today’s Episode with Bill Gurley and Michael Eisenberg You Will Learn: 1.) How does the current market activity in venture today compare to the dot com bubble? What elements are different? What elements are the same? What were the ramifications of the dot com bubble? Would Bill and Michael expect to see the same again? Is there anything good that comes from bubbles? How did the prior bubble impact Michael and Bill's investing mindset? 2.) Does Bill Gurley agree that Benchmark are the only firm to have retained price discipline in this crazy market? How do Bill and Michael think about their own relationship to price today? How does Bill try and answer the question, "what could go right?" when he meets entrepreneurs today? On reflection, what have been Michael and Bill's biggest miss? How did it change their approach? 3.) How does one compete in a world of Tiger and crossover funds? When it comes to capital deployment and pacing, do Michael and Bill agree with the suggestion of "playing the game on the field"? What are the nuances to this statement? What companies does Bill believe capital can be a moat for? What companies is capital not a moat and they should be conservative with raising and pre-emptive rounds? 4.) Do Bill and Michael believe that ownership still matters today with outcomes being larger than ever? How do Bill and Michael feel about the importance of temporal diversification today in a world of compressed deployment cycles? What investing lesson learned over 25 years in the business do Bill and Michael wish they had known when they started?  Item’s Mentioned In Today’s Episode with Bill Gurley and Michael Eisenberg Bill’s Favourite Book: The Storytelling Animal: How Stories Make Us Human

Adam Foroughi is the Co-Founder and CEO @ AppLovin, the company that allows developers to market, monetize, analyze and publish their apps. Under Adam's leadership, he has taken the company public, grown the team to over 1,000 people around the world, and scaled revenue in 2020 to $1.5Bn. Prior to AppLovin, Adam founded two companies—Lifestreet Media and Social Hour, and before that Adam started his career as a derivatives trader. In Today’s Episode with Adam Foroughi You Will Learn: 1.) How Adam made his way into the world of startups and came to found one of the world's largest gaming, advertising and marketing companies in the form of AppLovin? 2.) Adam founded 4 companies before AppLovin, does Adam believe in the benefits of serial entrepreneurship? What has he done differently with AppLovin having learned from past experience? What did he do the same, having seen it work before? 3.) Why does Adam advocate for as few meetings as possible within the company? Why does Adam believe meetings are unproductive? How do decisions get made internally without meetings? What is the structure and process? How does Adam create an environment where people make decisions without the fear of the repercussions? What are the breakpoints in company scaling? 4.) Why does Adam think that VCs did not want to invest in the early rounds? What were his biggest takeaways from those early fundraising days? How has Adam found the transition to being a public markets CEO? What does he like? What does he not like? How does Adam feel about pleasing the street but also having a long-term mindset?   5.) How does Adam structure his day? With 5 children, how does Adam approach work/life balance? What does his exercise and sleep routine look like? How does he do both weights and running without losing the productivity of the weights? What changes has he made in the last year that have made a significant difference? Item’s Mentioned In Today’s Episode with Adam Foroughi Adam's Favourite Book: Never Split the Difference: Negotiating as if Your Life Depended on It

Christoph Janz is the Co-Founder and General Partner @ Point Nine, one of Europe's leading early-stage firms with a portfolio including the likes of Zendesk, Algolia, Revolut, Nex Health, Loom and of course, Contentful. Prior to co-founding Point Nine, Christoph was a prolific angel investor and also the Co-Founder @ Pageflakes, leading the company from inception to their acquisition by LiveUniverse in 2008. Christoph is also one of the most thoughtful writers in SaaS and you can find his writing here. In Today’s Episode with Christoph Janz You Will Learn: 1.) How did a cold email from the solo founder of Contentful convince Christoph to lead their first round? What was it about the email that made Christoph excited? How does Christoph advise founders today when it comes to crafting cold emails to VCs? 2.) The Market: How did Christoph analyze the market when making the investment? How much of a role does market sizing and analysis play in determining whether Christoph will make an investment? What matters more team or market? How did the market change in a way that Christoph was not expecting? How did it evolve in a way he was expecting? 3.) Business Model: How does Christoph advise SaaS founders today in crafting variable pricing mechanisms? How can you create a pricing mechanism that does not disincentivize usage but also optimizes for value extraction? Where does Christoph see many founders go wrong when it comes to pricing? 4.) Fundraising: How did the early fundraising rounds for Contentful come together? How does Christoph advise founders today on whether to take pre-emptive rounds? When can they be helpful? In what circumstances can they be very damaging? What is the best outcome that founders should be optimizing for today with fundraising?

Eugene Wei is one of my favorite thinkers, writers, and strategists in tech today. Having spent the majority of his professional career at consumer internet companies, Eugene started his career with a 7-year stint at Amazon with a focus on product. He then joined Hulu leading the product, design, editorial, and marketing teams. Post Hulu, Eugene co-founded Erly, later acquired by Airtime, and then joined Flipboard as Head of Product. Finally, Eugene's last position was with Oculus as Head of Video. You have to check out Eugene's blog and can find his writing here. In Today’s Episode with Eugene Wei You Will Learn: 1.) How Eugene made his way into the world of tech and startups with his first position at Amazon? What did Eugene do differently that made him stand out to the recruiters at Amazon? 2.) Decision-Making: Why does the process and medium by which decisions are made matter so much? How has Euegene's decision-making process changed over time? Where do many people go wrong in constructing and optimising their decision-making process? What are Eugene's biggest takeaways and lessons from Jeff Bezos and Steve Jobs on messaging? 3.) The World of Social: What does Eugene believe is the graph design problem for so many social apps today? What does Eugene believe are the best and the worst design choices social media incumbents have made? How does Eugene encourage the next generation of consumer social founders to think through design decisions? 4.) Status as a Service: What does the concept of "Status as a Service" mean to Eugene? What is the biggest misunderstanding people have with the concept? What has fundamentally changed this concept in the last 2-3 years? How does the rise of crypto and NFT's impact the notion of "status as a service"? How does Eugene believe this will look in 10 years? 5.) The World of Media: How does Eugene think through the attention economy today? Why is media and content harder than ever today? Why does Eugene believe media has now become zero-sum? What does Eugene believe will be the future business model for media? Item’s Mentioned In Today’s Episode with Euegene Wei Eugene's Favourite Book: The Sound and the Fury, The Visual Display of Quantitative Information

Andy Johns is one of the pre-eminent growth leaders of the last decade. Andy's career started in growth at Facebook when the company scaled from 100M-500M active users. Since he has worked in some of the leading growth orgs at companies like Twitter, Quora and more recently at Wealthfront as Head of Growth and President. Andy is also an active angel investor and advisor with companies such as Poshmark, Robinhood, Webflow, Blue Bottle Coffee, and Opendoor. If that was not enough, Andy is currently a Venture Partner @ Unusual Ventures where he focuses on consumer social and network-driven startups. In Today’s Episode with Andy Johns You Will Learn: 1.) How Andy made his way into the world of startups and growth with his joining the Facebook growth team? What were the biggest takeaways from his time with Facebook, Twitter and Quora? How did that impact his mindset today? 2.) How does Andy define "VP and Head of Growth"? When is the right time to start hiring for your growth team? How should founders determine whether they need a growth leader or growth engineers in the early days? What is the core question founders need to ask on network effects to answer this question? Should the growth team be incorporated into the product team? 3.) How does Andy structure the hiring process for growth hires? What does the structure of the interviews look like? How does Andy test for real depth with candidates? What case studies does he do to really understand their quality? Where do many go wrong with the interview process? What are Andy's biggest suggestions for how to optimise the process? 4.) What does the optimal onboarding process for new hires look like? What takes and processes should they complete in their first month? What are early signs of a poor candidate? How long should one give them if they are not performing? How does Andy approach structure post-mortems within the team? What is the ideal relationship between CEO and Head of Growth?

Kareem Zaki is a General Partner @ Thrive Capital, with a portfolio including Stripe, Instacart, Instagram, Nubank, Github, Glossier and many more, they have cemented their position as one of the leading venture firms of the last decade. As for Kareem, he is a co-founder and board member to Cedar, Nava, Scope Security and Cadence and has invested in the likes of Affirm, Lemonade, Ramp and Trade Republic. Prior to entering venture, Kareem spent 3 years in private equity with Blackstone. In Today’s Episode with Kareem Zaki You Will Learn: 1.) How Kareem made his way from the world of private equity to backing some of the most innovative next-generation companies with Thrive Capital? 2.) Portfolio Construction: What is the one rule that drives all decision-making at Thrive? How does Kareem think about maintaining focus with such a broad mandate? How do Thrive think about asset allocation internally with such a broad mandate? How does incubating companies also help Kareem be a better investor? 3.) Investing Style: How has Kareem's investing style changed over the last 10 years? What does he focus on now that he did not before and visa versa? How does Kareem assess his own relationship to price? Through what lens does Kareem approach market sizing and timing? Where do many investors make mistakes here? 4.) The Landscape: How does Kareem respond to the activity and cadence of Tiger? In what way does Kareem believe the venture landscape will have changed most significantly in the next 10 years? How do the existing incumbent firms need to change in the wake of this? How do Thrive respond to the pace and cadence of check writing today? Item’s Mentioned In Today’s Episode with Kareem Zaki Kareem’s Favourite Book: How Will You Measure Your Life Kareem's Most Recent Investment: Cadence

Brian Singerman is a General Partner @ Founders Fund, one of the most prominent venture firms of the last decade with a portfolio including Anduril, SpaceX, Tesla, Palantir, Stripe, Affirm, Airbnb, Facebook, and many more. As for Brian, he has led investments in the likes of Affirm, Oscar Health, Wish, Asana, Oculus, and Postmates to name a few. Brian also sits on the board or is an observer to The Long Term Stock Exchange, Solugen, Cloud9, Modern Health, and of course, Anduril. Prior to Founders Fund, Brian spent a very successful 4 years as an engineer and executive at Google. In Today’s Episode with Brian Singerman on Anduril, You Will Learn: 1.) How did Brian first come to meet Palmer and the Anduril team? Where did the meeting take place? How did the discussion go? Did Brian instantly feel that Palmer was special? What about the way Palmer presented, suggested this to Brian? 2.) The Market: What gave Brian the confidence Anduril would be successful where so many others had failed? How did the market change or evolve in a way Brian did expect? In what ways did the market surprise Brian? Does Brian think we will see the relationship between Silicon Valley and the DOD change over time? 3.) Anduril: The Business: Why is Anduril as a business, so hard to copy? How did Brian gain comfort around their defensibility? What does Brian think is the biggest misconception people have of Anduril as a business? How does Brian think about when is the right time to add secondary and ancillary products? 4.) Investing Today: Why is Brian no longer Zoom investing today? What does Brian mean when he says you have to, "play a different game to the hedge funds today"? In what way does he and Founders Fund look to do this? How does Brian think about the current levels of pricing? How does he determine when to pay up vs when to be disciplined?

Arthur Patterson and Jim Swartz founded Accel in 1983. Under their leadership, they have built Accel into one of the most prominent venture firms of the last 4 decades. Starting with Arthur, as the lead investor, Arthur has helped management teams develop companies into market-defining leaders over an incredible four decades. Prior to co-founding Accel, Arthur was a General Partner of Adler & Company with his career in venture starting at Citicorp Venture Capital.  As for Jim, Jim has been the lead director of more than 50 successful companies. He was instrumental as a founder/mentor of Accel London and in the founding of Meritech Capital. Before Accel, Jim was the founding general partner of Adler & Company, which he started with Fred Adler in 1978 after his tenure as a vice president of Citicorp Venture Capital. In Today’s Episode with Arthur Patterson and Jim Swartz You Will Learn: 1.) How Arthur and Jim made their first entry into the world of venture capital in the 70's? What was the founding moment for them with Accel? Where did the first discussion happen? Did they align on strategy? Why did they decide to name the firm Accel? 2.) What did the venture ecosystem look like when Arthur and Jim founded Accel in 1983? Why does Arthur believe the specialist always beats the generalist? What was the hardest Accel fund to raise? Why was it the hardest to raise? When did the Accel brand hit an inflection point and fundraising became easier? Where do Arthur and Jim disagree on this? 3.) How do Jim and Arthur feel about the current frothiness of the venture market? Why does Jim believe we are entering a market correction? How do they feel about the inflation of asset value? Through what lens is now the same vs different to 1999/2000? What have been their biggest lessons from experiencing 5 macro booms and busts? 4.) How did Jim and Arthur think about when to expand with a new Accel product? What did Accel do specifically to make the expansion to London and India so successful? What is the key to doing generational transition well? Where do many go wrong here? Do Jim and Arthur agree with Doug Leone, "when you lose seed, you become private equity"? 5.) How do Jim and Arthur think about partner selection within the firm? How have they structured decision-making to ensure politics do not get introduced? How does one create a decision-making framework of accountability without fear to take big risks? What do Arthur and Jim mean when they speak of "the prepared mind"? How does it help them think and operate better?

Ryan Denehy is the Founder & CEO @ Electric, the company that provides a modern IT solution that's simplified. To date, Ryan has raised over $188M for the company from the likes of GGV, Bessemer, Slack Fund, and 01 Advisors to name a few. As for Ryan, he is a 3x entrepreneur with his first company being acquired by USA TODAY Sports and his second company, Swarm Mobile being acquired by Groupon in 2014. In Today’s Episode with Ryan Denehy You Will Learn: 1.) How Ryan made his way into the world of startups with his first startup being acquired when he was still in college? How have experiences raising $180M with Electric, impacted how he thinks about the venture market today? 2.) Is Ryan concerned by the lack of due diligence investors are doing today? How has the DD process changed over the years? What materials should founders provide to investors? How should founders reference check investors? What do many founders do wrong here? 3.) Should founders always take the most money at the highest price? When thinking about price, what do you founders have to think through? Why are some of the prices we are seeing today so crazy? How can founders outcome scenario plan to come to the best price option? When are founders and investors misaligned when it comes to price? 4.) What does Ryan mean when he says, "sales and product-market fit are more closely related than people think"? How does Ryan advise founders on when to really raise big? Does Ryan believe in the notion of "skipping a round"? Does this ever happen? Does Ryan ever believe the "this will be our last round before we breakeven" statement?

McKeever "Mac" Conwell II is the founder and managing partner of RareBreed Ventures, a pre-seed fund that invests outside of large tech ecosystems, with a concentrated portfolio approach being the first check with up to $250K. Mac's journey into venture is nothing short of inspirational, Mac went from being homeless to being an engineer to founding his own companies to today, raising Rarebreed largely on Twitter. In Today’s Episode with Mac the VC You Will Learn: 1.) How Mac went from being homeless to becoming an engineer and starting his own company? How did his time operating lead to his becoming a VC and building his Twitter brand? 2.) What are the biggest ways that venture is messed up today? Why does Mac believe it does not matter about getting into hot deals? Why does Mac believe that the brand of the VC that does your round does not matter? Does Mac see the leading venture brands investing outside SF and NYC? What elements of an investment compel them more than others? 3.) In the wake of the George Floyd event, who does Mac note did not say anything? How does Mac want to see diversity introduced at the institutional LP level? What does Mac believe institutional LPs care about? What can institutional LPs do structurally to allow themselves to invest in the next generation of emerging managers? 4.) Why does Mac not like AngelList Rolling Funds? How did he structure his fund in a creative way? How does Mac feel about the requirements for GP commits? How did Mac use Twitter very specifically to raise his fund? Which people went out of their way to help him? What were some of the biggest takeaways from those discussions? Item’s Mentioned In Today’s Episode with Mac the VC Mac’s Favourite Book: Why Should White Guys Have All the Fun?: How Reginald Lewis Created a Billion-Dollar Business Empire

Elena Verna is a master when it comes to all things starting and scaling growth organizations. Previously, Elena spent over 7 years as SVP Growth @ SurveyMonkey where she ran product, growth marketing, and data teams. Post SurveyMonkey, Elena worked with the rocket ship that is Miro both as Interim CMO and as an advisor. Elena has also advised some of the best growth orgs with advisor roles at HP, MongoDB, Netlify, Maze, and many more awesome companies. In Today’s Episode with Elena Verna You Will Learn: 1.) How Elena made her way into the world of tech and growth from a Craiglist job listing? What was her big break in the world of growth with her first Head of Growth role? 2.) How does Elena define "growth" and "Head of Growth"? When should startups not have a growth team? What are the 3 main levers to the growth model today? How does Elena advise between hiring a CMO vs Head of Growth? Where do many founders make mistakes with this decision in mind? 3.) Who are the wrong people to hire for your growth team? What characteristics and traits do these people have that make them bad for growth? What questions does Elena ask in interviews to determine if they have these traits? How does Elena advise founders structure the process of hiring their "Head of Growth"? Should it be internal promotion or external hire? 4.) Where do most founders go wrong in the onboarding phase of their growth team? What do you have to have in place before the growth team starts? What are the biggest red flags for founders when reviewing their growth teams in the first 3 months? Why does Elena not like post-mortems? What is the optimal relationship between CEO and Head of Growth? 5.) How can growth teams work most effectively with both product and engineering teams? How do they need to communicate to ensure a healthy relationship? Where do growth teams most often make mistakes here? What have been some of Elena's lessons on how growth can experiment without angering engineering teams?

Will Shu is the Founder & CEO @ Deliveroo, the company that provides your favorite restaurants and takeaways, delivered to your door. Prior to their IPO earlier this year, Will raised over $1.7BN for the company from some of the best including Accel, Index, General Catalyst, Greenoaks, and more. Before Deliveroo, Will worked in finance as an analyst with SAC Capital, ESO Capital, and Morgan Stanley in New York and London. Fun fact, Will still enjoys regularly delivering food orders on his bike. In Today’s Episode with Will Shu You Will Learn: 1.) How Will made his way from hedge funds and Morgan Stanley to changing the world of food and delivery with Deliveroo? Why did Deliveroo not work the first time Will started it? 2.) Restaurant + Customer Acquisition: How did Will acquire the first restaurants to the platform? What did that education process look like for them? What do the restaurants care about? How did Will acquire the first customers? How has that changed over time? What matters to customers; speed, selection or price? How does this change by geography and country? 3.) New Markets: How do Deliveroo select new markets to enter? What makes one more attractive than another? From a resource perspective, what does it take to open a new market? What have been some of the biggest lessons on zone maturity and time to breakeven? Why does Deliveroo not track driver efficiency on a number of drops basis? What is the right mechanism to measure driver efficiency? 4.) Competition: How did Deliveroo come late to markets like France and end up winning them? What was it like competing against Uber with Eats? How important is restaurant exclusivity to Deliveroo retaining its position? What would Will have done differently with regards to competition, with the benefit of hindsight? 5.) Quick commerce: What does Will make of the unprecedented rise of quick commerce? Will we see many winners on a per market basis or will this be a consolidatory environment? What do many of the new entrants mistake or not understand? Why is the vertical ownership of the supply chain such a superior model to working with grocery partners? Item’s Mentioned In Today’s Episode with Will Shu Will’s Favourite Book: From Third World to First: Singapore and the Asian Economic Boom

Ankur Nagpal is the Founding Partner @ Vibe Capital, today announcing his new $70M solo GP fund and with a track record that includes the likes of Roam Research, Eight Sleep, Circle, Hone Health and Maven to name a few. Prior to entering venture, Ankur was the Founder and CEO @ Teachable, a platform where educators can create and sell their own online courses. Ankur led the company until their reported $250M acquisition to Hotmart in 2020. In Today’s Episode with Ankur Nagpal You Will Learn: 1.) How Ankur made his way into the world of venture investing having founded and exited Teachable for over $250M having raised just $13M in venture funding? 2.) From Angel to Fund: How did Ankur's mindset change with the transition from angel to institutional VC? How does Ankur feel about the rise of party rounds? What does Ankur advise founders trying to get brand names on cap tables? 3.) Portfolio Construction: With the new fund, how does Ankur think through portfolio construction? What is his required level of ownership? How does Ankur feel about optionality checks to get data and information for a larger check down the road? Does Ankur feel it is possible to build ownership in your best companies? 4.) The Future of Venture: Why does Ankur feel that largely, VCs detract value when they invest in a company? Base level, what is Ankur's promise to founders he invests in? From his time as a founder, what does founders most want in their cap table? Will we see a generation of operator-led funds? Will this be a game of the 1%? How will the large funds respond to this? 5.) Emerging Markets: What are the 3 core characteristics that make emerging markets so attractive for Ankur? What elements concern Ankur when investing in emerging markets? How does he screen for integrity with more granularity? How does Ankur analyse the progression of emerging markets in terms of their own hype cycles? Item’s Mentioned In Today’s Episode with Ankur Nagpal Ankur’s Favourite Book: Losing my Virignity

Fidji Simo is the CEO @ Instacart, the company that allows you to order whatever you want from local stores, delivering it straight to your door. Fidji joined the Instacart board 10 months ago and just 3 months ago, Fidji joined Instacart full time as CEO. Prior to Instacart, Fidji spent an incredible 10 years at Facebook in numerous different roles including Head of Facebook App and before that Vice President of Games, Video and Monetisation. If this was not enough, Fidji earlier this year announced her co-founding of Metrodora, an integrated medical ecosystem with the vision of advancing women’s health. In Today’s Episode with Fidji Simo You Will Learn: 1.) How Fidji made her way from a small coastal fishing town in France to leading the Facebook App and becoming one of the most powerful CEOs in tech with her new role at Instacart? 2.) The Rise @ Facebook: How did Fidji rise in the ranks at Facebook so much faster than anyone else? What were the biggest inflection points in her rise? What bets did she make that others did not see? How did they play out? Did any of the bets go wrong? What did Fidji learn about management style when the bet went wrong? 3.) Problem Solving and Decision-Making: What framework does Fidji use to have the most effective problem-solving and decision-making process? How does Fidji built such tight trust and honesty with her team members? In what way can leaders make people feel safe to take big bets but also not lose accountability if it does not work out? 4.) The Move To Instacart: Why did Fidji decide that CEO of Instacart was the right next move for her? What was Fidji's hypothesis of how the first 100 days would go? What has been a surprise in the first 100 days? How do the best leaders onboard into new CEO roles? How does the role of CEO change when moving from private to public company? Item’s Mentioned In Today’s Episode with Fidji Simo Fidji’s Favourite Book: The Night Circus

George Kurtz is the CEO and co-founder of CrowdStrike, a leading provider of next-generation endpoint protection, threat intelligence, and services. Prior to Crowdstrike's incredibly successful IPO in 2019, George raised funding from the likes of Accel, General Atlantic, CapitalG, IVP and Warburg Pincus to name a few. Before founding Crowdstrike, George spent close to 7 years at McAfee in roles such as Worldwide Chief Technology Officer and GM as well as EVP of Enterprise. Finally, before McAfee, George started Foundstone in 1999 leading them very successfully to their acquisition by McAfee in 2004.  In Today’s Episode with George Kurtz You Will Learn: 1.) How George came to found Crowdstrike having been Worldwide CTO @ McAfee? How did the founding of his prior companies impact how George thought about the early days of Crowdstrike? What does George believe are the pros and cons of serial entrepreneurship? 2.) Funding: With the benefit of hindsight, how does George reflect on his approach to fundraising? How did what George needed from VCs change over time? How does George approach investor selection? Through what framework does George advise founders as the right way to construct their cap table? Where do many go wrong on investor selection? 3.) Talent Acquisition: What has enabled George to hire some of the best talent in the world? What is the right way to construct the hiring process to recruit the best? What does George mean when he says, "you cannot forget the spouse factor"? Why is cash a moat and important when it comes to talent acquisition? 4.) Leadership: How has George's style of leadership changed over time? What stage of leadership did George find the most challenging? How does George find being a public markets CEO? What elements does he enjoy the most? What does he enjoy the least? Why does George believe the company has been so well received by public markets? Item’s Mentioned In Today’s Episode with George Kurtz George’s Favourite Book: Good to Great: Why Some Companies Make the Leap...and Others Don't

Chris Sacca is the Founder and Chairman @ Lowercase Capital, one of the best performing funds in the history of venture capital with a portfolio including Uber, Stripe, Twitter, Instagram, Twilio, Docker and many more. Despite this incredible success, in 2017, Chris and his wife, Crystal announced they would be stepping back from day to day investing to focus on ongoing efforts to rescue our democracy, heal the planet, promote diversity within venture capital. Earlier this year, they announced Lowercarbon Capital, with $800M AUM, with the mission to back companies that make real money slashing CO2 emissions, and buying us time to unf**k the planet. Fun fact: As a result of his incredible investing success Chris has also been a Shark on Shark Tank and even starred in an episode of Billions. In Today’s Episode with Chris Sacca You Will Learn: 1.) How Chris made his way into the world of investing having started life as a lawyer? What was his first investment? How did the first Twitter $25K angel check come about? 2.) How does Chris evaluate his own relationship to money and wealth? Why did Chris and Crystal interview some of the wealthiest people? What did they learn from those discussions? How does Chris view the role of luck? Why was it when Chris lacked optimism he lost the most money? How did being $4M in the hole from public markets impact his mindset? 3.) What does it mean for Chris to bring up healthy and happy children? Why does Chris believe today's parenting has bred a generation of asshole kids? In what way is great parenting aligned to great team management? How does Chris give feedback to his teams vs his children? What tone should be used? Should it always be "radical candor"? Should it be immediate? 4.) Does Chris believe that VCs really add any value? What does Chris believe is his secret sauce? Why does Chris believe that as a VC you have to be outspoken and loud about the value you provide? What have been some of the biggest lessons for Chris from sitting on boards and working with Bill Gurley? Why does Chris believe that most VCs are shitty managers? 5.) Why did Chris decide to come back from retirement and found Lowercarbon with Crystal? Why did he not decide to do it all with his own money? Why is now different for climate tech than prior generations of climate tech innovation? How big does Chris want to scale Lowercarbon? Will Chris make more money from climate investing than from tech? Item’s Mentioned In Today’s Episode with Chris Sacca Chris’ Favourite Book: Not Fade Away: A Short Life Well Lived, How To Raise an Adult

Anthony Casalena is the Founder & CEO @ Squarespace, the company that allows you to create a website, sell anything and market your business. To date, Anthony has raised over $948M for the company from the likes of General Atlantic, Index Ventures, Tiger Global; culminating in their IPO in May 2021. Despite the incredible size and scale of Squarespace today, Anthony started the company from his dorm room in 2003 and bootstrapped the business for many years to today with over 1,100 employees around the world. In Today’s Episode with Anthony Casalena You Will Learn: 1.) How Anthony came to start Squarespace from a dorm room and turn it into a public company with over 1,200 employees globally? 2.) Why did Anthony decide to bootstrap with Squarespace for over 6 years when the company was scaling fast and profitable? How was Anthony's mindset impacted by the efficiency of bootstrap scaling? How did Anthony's mindset change when Squarespace raised their first large round? How does Anthony advise founders today on raising venture vs bootstrapping? 3.) Why did Anthony decide to do the direct listing over the more traditional IPO or a SPAC? How does Anthony advise other founders contemplating the same exit choices? How does Anthony personally describe this chapter of the company? Does he enjoy being a public company CEO? What are the best elements? What are the worst? 4.) E-Commerce has been a massive driver for growth for Squarespace, how does Anthony feel about the future of e-commerce on Squarespace? Only 1% of Squarespace's $700M ARR comes from enterprise, does enterprise hold a meaningful position in the future of the company? What are the core challenges of moving into enterprise? How does the company need to change? 5.) With the growth of the company, how has Anthony changed his style of leadership? What are his biggest strengths? What are his biggest weaknesses? What are the most obvious breakpoints in the scaling of companies? Item’s Mentioned In Today’s Episode with Anthony Casalena Anthony’s Favourite Book: Thinking Fast and Slow

Anton Levy is Co-President, Managing Director and Global Head of General Atlantic’s Technology sector. Anton has led General Atlantic’s investments in the likes of Alibaba, CrowdStrike, Facebook, Slack and Snapchat and co-led investments in Adyen and Bytedance. As a result, Anton has been named to the Forbes Midas List of top investors each year from 2014 to 2021. Anton has also enjoyed board positions either as a member or observer in companies such as Uber, MercadoLibre, Klarna and Meituan to name a few. In Today’s Episode with Anton Levy You Will Learn: 1.) How Anton made his way into the world of growth investing? What have been some of Anton's biggest lessons from seeing the booms and busts of the macro-environment? 2.) The Landscape: What does Anton believe are the two largest changes/trends in the venture landscape today? What does Anton think is the right way to respond to the threat of Tiger Global? How should founders think about active vs passive cash? How does Anton reflect on his own price sensitivity? What have been some of his biggest lessons on pricing? 3.) Portfolio Construction: How have GA had to change their approach to investing over the last few years? Why have they decided actively to move earlier and write smaller checks? How does a $50M investment from an $8BN impact portfolio construction thinking? How does GA determine which of their winners to size up into and write a $500M check? What is the process for that? 4.) Deployment Cycles: How does Anton think about the compression of deployment cycles in venture? Are people acting rationally? When will the bubble burst? How do interest rates impact capital inflows into venture? Why does Anton believe we are entering a golden age of innovation? What elements concern him? 5.) Culture- Building: What have been Anton's biggest lessons when it comes to culture building internally? Where do many make mistakes here? What have been the most surprising elements of scaling GA to Anton? What mistakes did they make? How did they move to correct them? Item’s Mentioned In Today’s Episode with Anton Levy Anton’s Favourite Book: Bridge to Terabithia Anton’s Most Recent Investment: Articulate

Keith Rabois is a General Partner @ Founders Fund, one of the most successful venture firms of the last decade with home runs in the likes of SpaceX, Palantir, Stripe, Anduril, Facebook, Airbnb, Nubank and many more. As for Keith, he led the first institutional investments in DoorDash, Affirm and has also led investments in Ramp, Trade Republic, Faire and Stripe. Prior to venture, Keith had the most stellar operating career, joining PayPal when their monthly burn-rate was $6 million; Keith joined LinkedIn, Slide and Square when they had no revenue. Fun fact, five companies Keith helped build are now publicly traded with market caps >$1 Billion. Three others have been acquired for greater than $1 Billion or are publicly traded IPOs. If that was not enough, Keith is also the Co-Founder and CEO @ OpenStore, acquiring small DTC businesses. In Today’s Episode with Keith Rabois You Will Learn: 1.) How Keith first came up with the idea for Opendoor? How a conversation with Peter Thiel led to the founding of the first iteration of the company? Why did it take Keith close to a decade to pursue the idea fully, post having the idea in 2003? 2.) The Market: What made Keith so excited to pursue Opendoor from a top-down market analysis perspective? What does Keith look for in markets he likes to invest in? How did Keith expect the market to change and evolve? What did the market do differently to how Keith thought it would behave? 3.) The Business Model: With debt being the oxygen for Opendoor, how many homes did they need to acquire before they could prove they could price homes accurately? What were Keith's lessons from the first homes they bought? What did not go to plan? Why does Keith disagree, if macro hits real estate, Opendoor's model is challenged? Why does Keith believe it is stronger then? 4.) The Team: What does Keith look for in the founding teams he backs? How does Keith detect diamonds in the rough? How can teams systematically de-risk an opportunity with their experience? With the benefit of hindsight, what would Keith have done differently with the team? 5.) The Funding: Was fundraising for Opendoor always easy? How did the seed round go down? How does Keith feel today about pre-emptive rounds where little company development has taken place? Why did Opendoor decide to SPAC? Why not a direct list? Was this the right choice? What makes for the best SPAC partner?

Ralf Wenzel is the Founder & CEO @ JOKR, a global platform for instant retail delivery at a hyper-local scale. To date, Ralf has raised over $170M for the company from the likes of GGV Capital, Balderton, Softbank and Kaszek, just to name a few. Prior to JOKR, Ralf spent close to 7 years as the Founder & CEO @ foodpanda as well as enjoying roles as Chief Strategy Officer @ Delivery Hero, Interim Chief Product and Experience Officer @ WeWork and even moving to the other side of the table as a Managing Partner with Softbank. In Today’s Episode with Ralf Wenzel You Will Learn: 1.) How Ralf made his way into the world of startups and came to found foodpanda? What were his biggest takeaways from foodpanda that have impacted how he thinks about scaling JOKR today? 2.) Fulfillment Centres: What are the selection criteria when deciding what is the right location for a fulfillment center? How does real estate cost differ when comparing LATAM to the US? How does Ralf think about the balance between consumer choice and SKU minimization? In what way does Ralf believe they have a moat due to their catalog management system? 3.) The Driver: Why is JOKR different to every other provider in the way they employ their riders? Does it not severely impact their margins by providing equal benefits across their entire rider workforce? How many drops per hour is a good level of driver efficiency? What have been Ralf's biggest lessons when it comes to driver retention? 4.) The Consumer: How did JOKR acquire their first consumers on the demand side? What marketing strategies worked? What did not work? Is Ralf concerned by the immense amount of money invested in the space driving customer acquisition prices way higher? How has Ralf seen CACs change over time in mature markets? 5.) Expansion Opportunities: How does Ralf feel about incorporating own brand products, produced by JOKR over time? How does this change the margin profile of the business? How does Ralf feel about paid search as a core part of their business? Will CPGs be able to pay to be ranked higher in JOKR?

Casey Winters is the Chief Product Officer at Eventbrite where he leads the PM, product design, research, and growth marketing teams. Prior to Eventbrite, Casey spent close to 3 years at Pinterest where he led the growth product team. At Pinterest, Casey turned SEO into a scalable acquisition strategy, increasing conversion to signups 5x. Before Pinterest, Casey started the marketing team at Grubhub and scaled Grubhub's demand-side acquisition and retention strategies. Casey played an instrumental role in scaling Grubhub from 3 cities to 1,000+ and from a $1 million series A to an IPO and $7.3 billion exit. If that was not enough, Casey has also advised the likes of Canva, Hipcamp, Reddit, Faire and Career Karma to name a few. In Today’s Episode with Casey Winters You Will Learn: 1.) How Casey made his way into the world of startups and came to lead some of the most powerful growth orgs in the world from Pinterest to Grubhub to Eventbrite? 2.) How does Casey define "growth" and "Head of Growth"? When is the right time to start thinking about implementing a growth team? When should one hire a growth leader? How should founders structure the process of hiring a Head of Growth? What do the stages look like? What signals suggest A* talent? What questions does Casey always ask? What tests does Casey do? 3.) What does the optimal onboarding process look like for growth teams? What tasks should a growth team perform in their first few months? What are clear signs you have an amazing candidate in place? What are some obvious red flags? How do the best growth teams approach post-mortems? How are they structured? Who attends them? How often? 4.) What is the ideal relationship between the Head of Growth and the CEO? How often do they meet? What do the best CEOs expect from their growth teams? How does Casey approach the relationship between growth teams and product teams? How does one know when to have an independent growth team vs within the product or marketing team? 5.) Casey AMA: What has been a decision that Casey made without data to back it up? How did it go? What were Casey's lessons? How does Casey prevent past experiments from impacting his future tactics? How does Casey's management style differ when managing larger vs smaller growth teams? How has angel investing impacted his approach to scaling growth teams?

Hans Tung is a Managing Partner at GGV Capital, one of the leading venture firms of the last 2 decades with a portfolio including Alibaba, Xiaomi, Peloton, Airbnb, Slack, and many more. As for Hans, he has been named to the Forbes Midas list nine consecutive years from 2013-2021, most recently ranking #3. His portfolio includes 18 unicorns including Affirm, Airbnb, Coinbase, Divvy Homes, Peloton, Poshmark, Slack, Wish and Xiaomi. In 2005, he was among the first Silicon Valley VCs to move to China full time, spending eight years investing in the fastest-changing tech landscape in the world before returning to Silicon Valley in 2013 to join GGV Capital. In Today’s Episode with Hans Tung You Will Learn: 1.) How Hans made his way into the world of venture from founding his first two companies? How did seeing the booms and busts of the macro-financial markets impact both his investing mindset and the companies he likes to back? 2.) The Landscape: How does Hans analyze the current venture landscape today? How does one compete in a world of Tiger and crossover funds writing term sheets post first meeting? How does Hans think about his own price sensitivity today? How does he determine when to pay up vs when to say no? What have been some of his biggest lessons on price? 3.) Working with the likes of Peloton, Square, Alibaba, what have been some of Hans biggest lessons on market size? What do most investors get wrong when it comes to market sizing? How does Hans think about an attractive enough exit multiple for a growth stage check? What did Peloton teach Hans about insertion points when investing? 4.) How does Hans think about when is the right time to sell? What have been some of his biggest lessons on taking cash off the table? Despite the success, how does Hans ensure he has the mental plasticity to approach every new deal with a fresh perspective? What does he do to ensure he does not have an unconscious bias from his past successes? Item’s Mentioned In Today’s Episode with Hans Tung Hans’ Favourite Book: Outliers: The Story of Success Hans’ Most Recent Investment: JOKR

Nazim Salur is the Founder & CEO of Getir, one of the leading rapid delivery service providers that distribute over 1,500 everyday items within minutes. With an established status in Turkey, where the company trends towards a super-app, and a London launch behind it, Getir has further European and US expansion plans on the horizon. To fuel this expansion, Getir has raised over $1BN from Sequoia and Mike Moritz, Silver Lake, Mubadala, and Tiger Global to name a few. Prior to founding Getir, Nazim launched his first tech startup in 2012, BiTaksi, which brought people taxis in three minutes. In Today’s Episode with Nazim Salur You Will Learn: 1.) How Nazim made his way into the world of startups with his founding of BiTaksi and how that led to his realization of the need for Getir? 2.) Why does Nazim believe that owning the entire vertical stack is a superior model? What are the selection criteria for the micro-fulfillment sites? What makes one more attractive than another? How does Getir think about the balance between SKU minimization and consumer demand? How does Getir think about building defensibility through their warehouse management system? 3.) How did Getir acquire their first drivers? What worked? What did not work? How does their driver acquisition strategy change depending on location? What is the core measurement that Getir uses to measure driver efficiency? What is the secret to driver retention? How has Nazim seen driver acquisition costs change over time in mature markets? 4.) How did Getir acquire their first customers? What is the most important element for consumers; speed or choice? How does Getir think about allocating marketing spend efficiently today? How has Nazim seen CACs change over time with the maturation of markets? With the immense funding for the space, is Nazim concerned about this? 5.) What are the decision-making criteria for what makes an attractive region to expand into? How much capital does it take to launch a new region? What is the time to profitability on each zone? How has this changed over time? How does Nazim think about expansion into the US? What excites him most about the expansion? What elements will be most challenging?

Doug Leone is the Global Managing Partner @ Sequoia Capital, one of the world’s most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom and many more. As for Doug, he joined Sequoia over 33 years ago and has led investments in Nubank, Meraki, ServiceNow and TradeRepublic to name a few. In Today’s Episode with Doug Leone You Will Learn: 1.) How a 5PM Monday meeting with Don Valentine led to Doug joining Sequoia over 33 years ago? What did Don ask Doug in the meeting? What does Doug believe led Don to offer him his first role at Sequoia? 2.) The Leader: How did Doug change when he made the transition from a "COO" role to more of a "CEO" role with Sequoia? Doug has previously said, "Sequoia is a team, not a family". What does he mean by this? How do Doug and Sequoia do to give the team an unwavering sense of duty to the Sequoia brand? What does Doug believe Sequoia have done so well to allow them to move seamlessly from generation to generation? 3.) The Investor: Doug's first 3 investments all went on to successful IPOs, how did this impact his mindset at the time? What does Doug mean when he discusses "the abyss" he went through post this time? How does Doug advise others going through the abyss? What are the signs certain people will make it through vs not? 4.) The Landscape Today: How does Doug think about and react to newer entrants like Tiger and Softbank? How does Doug think about and assess his own price sensitivity today? How does Doug determine when to be disciplined vs when to pay up? Through what lens does Doug assess the compression of deployment cycles in venture today? Should we "play the game on the field"? 5.) The Expansion: In 2005, Sequoia expanded to China. Why was this the right time? What was the decision-making process for the Sequoia China team? Why does Doug believe, "when you lose pre-seed, you become private equity"? How does Doug react to the notion that success in venture is cyclical and compounds? Item’s Mentioned In Today’s Episode with Doug Leone Doug’s Favourite Book: The Fountainhead: Ayn Rand, Antifragile: Things that Gain from Disorder

Sameer Gandhi is a Partner @ Accel, one of the leading venture firms of the last decade with a portfolio including the likes of Facebook, Dropbox, Atlassian, Hopin, Spotify and more. As for Sameer, he led investments in Crowdstrike, Dropbox, Flipkart, Spotify and more. Prior to Accel, Sameer spent close to 10 years as a Partner @ Sequoia. In Today’s Episode with Sameer Gandhi You Will Learn: 1.) How Sameer first came to meet George, Crowdstrike Founder and CEO? How did a 30-minute meeting turn into a 2-hour discussion leading to Accel's investment? 2.)The Market: How did Sameer analyze and break down the market at the time of the investment? What hypothesis did he have on market evolution going in? What elements went as thought? In what way did the market evolve in a way Sameer did not expect? How does Sameer think through market timing today? Through what approach does Sameer assess market sizing today? 3.) Financing: How did Sameer build the confidence to lead multiple rounds of financing, one after the other? How did Sameer build the trust and strength of relationship with George to win each round? Why did Sameer advise George to "go shop his term sheet"? What was the rationale? How does Sameer advise founders on taking pre-emptive rounds today? 4.) Execution: What specifically allowed Crowdstrike to move so fast in the early days? Does Sameer believe that speed of execution is the strongest moat a company can have? How does Sameer advise companies today on services revenue? In what shape did this look with Crowdstrike in the early days? What is a healthy proportion of services to product revenue? 5.) The Team: How did George evolve and develop as a leader in the decade Sameer worked with him? What were some of the core inflection points that caused those changes? Who are some of the unsung heroes behind the scenes who moved the needle for Crowdstrike? What is Sameer's favorite memory from working with the company? Item’s Mentioned In Today’s Episode with Sameer Gandi Go to thetwentyminutevc.com to download the original Crowdstrike Investment Memo. 

Marcelo Claure serves as CEO of SoftBank Group International and COO of SoftBank Group Corp., the world’s largest tech investor. At Softbank, Marcelo oversees the company’s strategic direction and its portfolio of operating companies, including WeWork, SB Energy, Fortress, Boston Dynamics, as well as SoftBank’s stake in T-Mobile U.S. He also spearheads the SoftBank Latin America Fund, a $5 billion fund dedicated to investing in technology growth opportunities throughout the region. If that was not enough, Marcelo serves as Exec Chairman @ WeWork, is on the board of Arm, is the president of Club Bolívar, Bolivia's most popular and successful soccer team; co-owner and Chairman of Inter Miami CF and most recently co-owner of Girona FC. In Today’s Episode with Marcelo Claure You Will Learn: 1.) How Marcelo made his way into the world of startups and came to found his first company, Brightstar? How did Brightstar lead to Marcelo meeting Masa and moving to Tokyo to invest $1BN per week with him? 2.) From spending a year with Masa in Tokyo, what did Marcelo learn about Masa that he did not know before? How did spending this time with Masa impact Marcelo's operating mindset and his investing mindset? What were the most memorable founder meetings that Marcelo and Masa had in that year? Why did those ones stand out? 3.) When starting Softbank's LATAM Fund, what hypothesis did Marcelo have going into investing in LATAM? Which were confirmed? On the flip side, which proved to be wrong? How does Marcelo respond to people that say "LATAM produces copycat companies"? Why does Marcelo bet that Softbank will have 8 portfolio companies in LATAM go public next year? 4.) How does Marcelo think about the importance of price and price discipline today? What is their decision-making framework when determining whether to pay up or not for a deal? What have been some of Marcelo's biggest misses? How did they impact his decision-making process moving forward? How does Softbank approach conflicts when investing today? 5.) How does Marcelo analyze the increasing competition in the LATAM ecosystem? How has his style changed as a result? Through what lens does Marcelo assess the role that Tiger has played over the last 18 months? Why does Marcelo think that other firms have trash-talked Softbank before? How does Marcelo see the venture landscape as fundamentally changed? Item’s Mentioned In Today’s Episode with Marcelo Claure Marcelo’s Favourite Book: Endurance: Shackleton's Incredible Voyage to the Antarctic Marcelo’s Most Recent Investment: Uala

Frank Rotman is a founding partner of QED Investors, one of the leading fintech-focused venture firms investing today with a portfolio including the likes of Klarna, Kavak, Quinto Andar, Credit Karma and more. As for Frank, prior to QED, Frank was one of the earliest analysts hired into Capital One and spent almost 13 years there helping build many of the company’s business units and operational areas. Post Capital One, Frank went on to found a student lending company before joining up again with Nigel Morris to co-found QED. In Today’s Episode with Frank Rotman You Will Learn: 1.) How Frank made his way into the world of venture having spent 13 years scaling Capital One? What was the founding moment for Nigel and Frank with QED? How does Nigel compare to poker to venture capital? Where are they similar? Where are they different? 2.) Does Frank feel that price discipline has disappeared in the venture market today? What have been some of Frank's biggest lessons on price? Is Frank concerned by the compression in deployment timelines for funds? How does Frank feel on the rise of pre-emptive rounds? In what way does Frank advise his founders when they are offered pre-emptive rounds? 3.) How important does Frank believe sizing your initial position is, from an ownership perspective? Is it possible to build ownership in your winners? What have been some lessons for Frank with regards to the speed of which breakout companies are clear? How does Frank assess and analyse bridge rounds and whether to participate or not? 4.) Why does Frank believe that the VC world is less collaborative than ever today? What has caused this? What can VCs do to change this? How do we solve the structural problem of VCs needing ownership for their business and founders not wanting excessive dilution? What does Frank believe is the most dangerous trend in the VC market today? 5.) How does Frank think about what he can do to improve his investment decision-making process? What repeatable process has Frank landed on that works? Where do many make mistakes here? How does Frank view the relationship between process and outcome? Item’s Mentioned In Today’s Episode with Frank Rotman Frank’s Favourite Book: Tom Robbins Frank’s Most Recent Investment: Hello Alice

Emilie Choi is the President and Chief Operating Officer @ Coinbase, the easiest place to buy and sell cryptocurrency. Prior to their IPO earlier this year, Coinbase raised funding from some of the best in the business including USV, a16z, Initialized and Ribbit to name a few. As for Emilie, before Coinbase she was Head of Corporate Development for @ LinkedIn and before Linkedin served in various positions at Warner Bros., including as Manager of Corporate Business Development and Strategy. If that was not enough, Emilie currently serves on the board of Naspers and ZipRecruiter. In Today’s Episode with Emilie Choi You Will Learn: 1.) How Emilie made her way into the world of startups, came to lead Corp Dev @ Linkedin and how that led to her joining forces with Brian @ Coinbase as COO & President? What lessons did Emilie learn from Reid Hoffman and Jeff Weiner that she has taken with her to Coinbase? 2.) Corp-Dev Guide: Why are so many startups trying to hire Head of Corp Devs today? What are the signals that suggest now is the right time? How would Emilie structure the process of hiring a Head of Corp Dev? What questions should be asked? How can you test their skills? What mistakes do CEOs often make when hiring Head of Corp Devs? 3.) COO Guide: What does the role of COO really mean to Emilie? How does Emilie advise founders on whether they do actually need a COO? How would Emilie structure the process of hiring a COO? What are some common red flags that concern Emilie when hiring COO's? What is the right relationship between CEO and COO? 4.) Resource Allocation: How does Coinbase think about internal resource allocation between core product and their venture products? What was the thinking behind Coinbase Ventures? Why do they have no full-time staff? What is the core objective of the fund? Why does Emilie think it will be one of the best performing funds in venture? Item’s Mentioned In Today’s Episode with Emilie Choi Emilie’s Favourite Book: The Secret History

Angela Strange is a General Partner at Andreessen Horowitz, one of the leading venture firms of the last decade with a portfolio including the likes of Facebook, Github, Slack, Airbnb, Asana and more. As for Angela, she largely focuses on investments in financial services and a16z has made significant investments in LATAM in the likes of Loft, Jeeves, Pomelo and Addi to name a few. Prior to a16z, Angela was a product manager at Google where she launched and grew Chrome for Android and Chrome for iOS into two of Google’s most successful mobile products. In Today’s Episode with Angela Strange You Will Learn: 1.) How Angela made her way into the world of venture from a career of running marathons and product management at Google? 2.) Does Angela believe we are going to see regional winners in LATAM with players owning their segment for Argentina, Mexico, Brazil etc? Why does Angela believe there is a huge business to be had in catering to the unbanked? How does Angela analyze whether startups can acquire distribution before incumbents acquire innovation? 3.) How does Angela respond to the suggestion that LATAM merely produces copycat companies of Western alternatives? How does Angela respond to claims that there is a lack of viable exit opportunities with insufficient local public markets and few international acquirers in the region? Does Angela believe there is a sufficient depth of engineering talent in the region? 4.) What has been Angela's biggest miss? How did it change her investment process? How does Angela analyze TAM? Where does Angela think many make mistakes in their underwriting of market size? How has Angela learned to think through societal and behavioral changes that impact market timing (cash-based economies, COVID etc?) Item’s Mentioned In Today’s Episode with Angela Strange Angela’s Favourite Book: More More Than You Know: Finding Financial Wisdom in Unconventional Places Angela’s Most Recent Investment: Jeeves

Nicolas Szekasy is a co-founder and Managing Partner of Kaszek Ventures, the largest venture capital firm in Latin America with a portfolio including the likes of Nubank, Notco, Creditas, Bitso and more. Before Kaszek, Nicolás was CFO for 10 years at MercadoLibre (Nasdaq: MELI), Latin America’s largest online commerce and payments platform, where he led its $333 million IPO in 2007. Before MercadoLibre, Nico spent 7 years as CFO @ PepsiCo. If that was not enough, Nico is also on the board of Endeavour, empowering a global ecosystem of entrepreneurs. In Today’s Episode with Nicolas Szekasy You Will Learn: 1.) How Nico made his way into the world of startups with MercadoLibre? What were the biggest takeaways from his 10 years with MELI? How did his time with MELI and seeing the boom and bust impact his investing mindset? 2.) What have been the most significant changes in the LATAM ecosystem over the last 20 years? What has improved? What has become more challenging? Is Nico concerned by the sheer amount of capital now flowing into the LATAM ecosystem at such speed? 3.) How does Nico respond to the statement that LATAM just produces "copycats" of successful companies from other geographies? How does Nico respond to the common suggestion of the challenges in scaling engineering teams in LATAM? How does Nico respond to the assumption that exit opportunities and IPOs are less available to LATAM companies? 4.) How was the experience of raising the first Kaszek fund? What has been the biggest challenging in the scaling from a $100M fund to a $1BN fund? How has Nico seen his own investing style change over the last decade? What does he know now that he wishes he had known when he started Kaszek? 5.) How does Nico reflect on his own style of board membership? What does Nico believe makes the best board members? What takeaways did he have from his time @ MELI on what makes the truly special board member? Item’s Mentioned In Today’s Episode with Nicolas Szekasy Nico’s Favourite Book: Guns, Germs and Steel: A short history of everybody for the last 13,000 years Nico’s Most Recent Investment: Notco

Ann Miura Ko is the Co-Founding Partner @ Floodgate, one of the leading early-stage firms of the last decade with a portfolio including the likes of Twitter, Twitch, Lyft, Okta, Outreach and more. As for Ann, not only did she lead the round for Lyft but in the last 12 months has led rounds for 2 of the hottest companies in the valley; Popparazzi and Popshop Live. Due to her immense investing success, Ann is a multiple Forbes Midas Lister and is also a lecturer in entrepreneurship at Stanford, a co-director of the Mayfield Fellows Program at Stanford, and a member of the Board of Trustees for Yale University. In Today’s Episode with Ann Miura Ko You Will Learn: 1.) How Ann made her way from a PhD in Quantitative Modelling at Stanford to co-founding one of the leading early-stage firms in the valley? 2.) What does Ann believe is the secret to successful seed investing? What insight development did Ann believe Lyft had? How had they approached customer development in such a unique way? What are the leading signals to Ann today that founders really understand the customer development process? What questions does she ask to discover this? 3.) Why does Ann not engage in the compression of fundraising timelines today? How does she build relationships of trust and honesty with founders so early? Does Ann worry that founders have such large capital injections too early today? Why should employees examine capital efficiency, not capital raised? How does Ann advise founders on pre-emptive rounds? 4.) How did Ann and the Lyft team approach prioritization in the early days? In what ways did Lyft decide to "play their own game" when it came to the competition? How did Uber and its growth impact the financing strategy for Lyft? In what deliberate ways did John and Logan set the culture for Lyft? What have been Ann's biggest lessons from them on culture building? 5.) Does Ann believe that capital in itself is a competitive moat today? What does Ann believe needs to be proven before capital can be used as a weapon to win? In the case of Lyft, what signals or measurements did Ann define as guiding metrics for success? How did they change over time? How can founders determine their own in their businesses?

Mike Lazerow is a serial entrepreneur and now Co-Founder and Managing Partner @ Velvet Sea Ventures alongside his wife, Kass. Prior investments from the Velvet Sea Partners include Twitter, Square, SpaceX, Snap Inc., Facebook, Pinterest, Domo, and more. Prior to becoming an investor, Mike founded Buddy Media in 2007, selling the company to Salesforce just 5 years later for $745M. Before Buddy Media, Mike co-founded Golf.com, a multi-million dollar profitable golf media property that Mike and Kass sold to Time Inc in 2006. In Today’s Episode with Mike Lazerow You Will Learn: 1.) How Mike made his way into the world of startups way back in 1993, how that led to Golf.com and Buddy Media? Why did he decide he wanted to be a VC? How did seeing the dotcom era fundamentally impact Mike's approach to business and investing? 2.) Why does Mike believe how you operate as an investor is more important than who you are and what you have done? How does Mike aim to invest and operate with this in mind? What are 3 core elements that Mike looks for in every deal? How does Mike approach his own investment decision-making process? How has it changed over time? How does he use gut to make decisions? 3.) What does Mike believe are his biggest insecurities as an investor? How does Mike think about the challenge of moving from a collaborative angel to a competitive VC? How does Mike think about the importance of ownership today? What has Mike learned about how the best VCs engage with round construction? 4.) How does Mike analyse his own style of board membership today? Why does Mike believe that boards are more helpful for the entrepreneur than for the investor? As an entrepreneur, how did Mike prepare for his boards? How does Mike advise founders to get the most out of their boards? Where do many make mistakes? How can one optimize the board member/founder relationship? 5.) Why does Mike believe that "having sex with your partner is a feature, not a bug"? How do Kass and Mike work together in such a complementary fashion? How do they ensure that personal matters never intrude on work decisions? How does Mike think about his relationship to money today? How does Mike want to imbue the same hard work and ethics to his children? Item’s Mentioned In Today’s Episode with Mike Lazerow Mike’s Favourite Book: Man's Search for Meaning Mike’s Most Recent Investment: LeoLabs

Christa Quarles is the CEO @ Corel Corporation, building software solutions that simplify the task journey for knowledge workers. Prior to Corel, Christa spent close to 4 years as CEO @ Opendoor, driving a chapter of transformational change for the company. Before Opendoor, Christa was Chief Business Officer @ NextDoor, and finally pre-NextDoor, Christa spent 4 years at The Walt Disney Company where she led Disney Interactive to profitability as Senior Vice President, Interactive Games. If that was not enough, Christa is also on the board of Affirm and Kimberly Clark. In Today’s Episode with Christa Quarles You Will Learn: 1.) How Christa made her way into the world of startups having spent close to 10 years in investment banking? What were the biggest takeaways from her time at Walt Disney? How did her 3 years as CEO @ Opentable impact how she approaches leadership today? 2.) Company Breakpoints: What are the different breakpoints in the scaling of companies? When did this start to happen at Opendoor? How does decision-making need to change with scale? How can leaders ensure teams feel safe to be the most ambitious they can be? In what ways can leaders create environments of safety for them to be their best selves? 3.) The Role of the CEO: What decisions can only the CEO make? How can leaders determine when a C-Suite hire is a stretch too far? How has Christa's board membership on other boards changed how she runs her board today? Given a board's limited information, how can leaders extract the most out of them? 4.) "Operating is a Full Contact Sport": When has Christa found operating and leading the hardest? When faced with hard times, how does she push through them? How does Christa advise leaders on the challenges of their own scaling process? Where do many make mistakes in their own scaling? What is a "stuck state" and why is it the worst state to be in? 5.) Team Building and Trust: How does Christa approach trust today? Does she start from a position of being fully trusting or not trusting and there to be gained? What is Christa's favourite interview question to ask? In what way does Christa believe truly special candidates represent their passions in interviews? Item’s Mentioned In Today’s Episode with Christa Quarles Christa’s Favourite Book: Caste, The International Bestseller

Nick Shalek is a General Partner @ Ribbit Capital, specializing in fintech they are one of the most successful venture firms of the last decade with a portfolio including Robinhood, Coinbase, Revolut, Nubank and more. As for Nick, he started his career as a Senior Analyst @ Yale Investments Office before moving to the world of operations as Director of Business Operations @ Verne Global, a provider of 100% carbon neutral data centers. In Today’s Episode with Nick Shalek You Will Learn: 1.) How Nick made his way from Senior Analyst at Yale's Investment Office to be one of the leading fintech investors in the world with Ribbit? What were Nick's biggest lessons from his time working with David Swenson @ Yale? How would Nick summarise Yale's investment algorithm? 2.) Entering Venture and Advice: Why does Nick tell many friends entering venture, to not join a new fund? What does Nick believe is takes to build an enduring firm in venture? What were the core reasons and inflection points in the success of Ribbit? What have been some of the biggest challenges in the professionalisation of Ribbit over the years? 3.) Pricing and Ownership: Is Nick concerned by the levels of pricing we are seeing in fintech today? How does Nick analyze his own relationship to price? How does Nick view the importance of ownership? Is it possible to build ownership across rounds? How does Nick advise founders now receiving very fast offers to pre-empt their rounds? 4.) Investment Decision-Making: How does Ribbit structure its investment decision-making process for initial investments? In what way does this process change for re-investments? Why does Nick believe in the benefits of not having attribution within venture partnerships? 5.) AMA: What has been Nick's biggest miss? How did it change his investment decision-making process as a result? What does Nick know now that he wishes he had known when he started in venture? What have been Nick's biggest lessons from his working with Micky? Item’s Mentioned In Today’s Episode with Nick Shalek Nick’s Favourite Book: A Piece of the Action: When the Middle Class Joined the Money Class Nick’s Most Recent Investment: Kavak

Jeff Immelt is a Venture Partner @ NEA serving on both the technology and healthcare investing teams. Prior to entering the world of venture, Jeff served as chairman and CEO of GE for 16 years where he revamped the company’s strategy, re-established market leadership and quadrupled emerging market revenue. As a result, Jeff has been named one of the “World’s Best CEOs” three times by Barron’s. In addition, Jeff is on the board of Sila Nanotechnologies and Twilio. In Today’s Episode with Jeff Immelt You Will Learn: 1.) How did it feel when Jeff was told he was going to be CEO at GE? How did that come about? Did he feel the weight of responsibility when it was announced? 2.) When it comes to incumbents embracing innovation, what strategies work? Why do they work? What lessons does Jeff take from his time at GE on what worked? What strategies do not work? What are the biggest mistakes large incumbents make when adopting new products or strategies? What advice does Jeff continuously tell large company CEOs who ask this question? 3.)  When does Jeff believe boards can be fundamentally impactful? In what circumstances do boards actually cause harm? What are the signs of the truly great board members? What are the causes of why board members can be misaligned with their founders? How should founders approach whether to listen or not to their board? 4.) How does Jeff think about trust in teams? Does he start fully trusting and it is their to be lost or start not trusting and it is their to be gained? What people do you want around you in a crisis? What are the signals of these people? What does Jeff mean when he speaks of "crisis accelerants and crisis absorbers"? 5.)  How does David think about fear in leadership? What is the one thing that leaders are allowed to be afraid of? How do the best founders approach their relationship to paranoia? How do the best communicate their fears to their team?

David George is a General Partner @ Andreessen Horowitz where he leads their growth investing practice. Since joining in 2019 David has invested in the likes of Clubhouse, Coinbase, Databricks, Figma, Instacart, Robinhood and TripActions just to name a few. David also sits on the board of Current, Greenlight, and Workrise. Prior to a16z, David spent 7 years growth investing at General Atlantic where he invested in the likes of Airbnb, Crowdstrike, Opendoor, Slack and Uber. In Today’s Episode with David George You Will Learn: 1.) How David made his way into the world of growth investing with General Atlantic and how that led to his leading the newest iteration of a16z growth funds? What were David's biggest takeaways from his time with General Atlantic? How did it impact his investing? 2.) Misconceptions of Growth Investing: Why does David believe that great business models are table stakes at growth today? What gives the best the edge? Why does David believe that people over-rotate on TAM? Why is it misleading in many ways? What is the right way to assess TAM at growth today? What does David look for when digging into unit economics? When is the right time to focus on unit economics? 3.) Portfolio Construction and Scenario Planning: How does David think about portfolio construction with the new a16z growth fund? What is the right level of diversification? How does David think about loss ratio today? How does David approach outcome scenario planning? What is an attractive level of upside for David to engage at growth? How has that expectation changed over time? 4.) Valuations and Crossover Funds: How does David assess the valuation landscape today? How does David determine whether he will pay up or sit out on an investment? How has the rise of crossover funds, PE funds and hedge funds entering growth impacted the valuations being paid and the investment process itself? What does David make of these new entrants? What challenges do they bring? 5.) Investment Decision-Making: How do a16z approach decision-making at growth? Who is on the core IC? Why does David strongly believe in the single trigger model in venture when it comes to decision-making? What are the biggest reasons for politics in venture firms today? What can be done to mitigate them? Item’s Mentioned In Today’s Episode with David George David’s Favourite Book: Increasing Returns To Scale David’s Most Recent Investment: Loom

Nick Mehta is the CEO @ Gainsight, the leader in all things customer success helping you put your customer at the heart of your business. Last year, as a result of their incredible success, Gainsight was acquired by Vista for a reported $1.1Bn but prior to that had raised over $156M from Lightspeed, Battery, Bessemer, Insight and Bain to name a few. As for Nick, he has been named one of the Top SaaS CEOs by the Software report three years in a row and holds one of the highest Glassdoor approval ratings for CEOs. Prior to Gainsight, Nick was the CEO at LiveOffice, which grew substantially and eventually sold to Symantec. In Today’s Episode with Nick Mehta You Will Learn: 1.) When did mental health really become a prominent thought for Nick? When was the first time Nick feels he really showed true vulnerability in leadership? 2.) Self-Worth: Does Nick feel like he is enough? What does he do when he questions himself severely? How does he talk to his wife about these challenging thoughts? Where does Nick believe this comes from? What are the dangers of people-pleasing? How does Nick try and counter people-pleasing in his role as a leader? 3.) Identity: How does Nick think about his own identity when it is so attached to Gainsight? In what ways does he try to detach? What has worked? What has not worked? How have children helped Nick in this way? 4.) Striving: Why does Nick believe that hunger and striving are fundamentally a good thing? How does Nick try and factor gratitude and appreciation into the work and success he experiences? How does Nick encourage this same striving in his children? 5.) Relationship to Money: How would Nick evaluate his relationship to money? How has it changed over time? How does Nick try to imbue the same values he had growing up in his children? Does Nick believe it is possible to "change" your children and have that impact?

Marc Lore is a serial entrepreneur turned investor who’s started and sold four companies. Most recently Marc was the President and CEO of Walmart eCommerce US following the sale of his company, Jet.com, to Walmart for $3.3 billion in 2016. Prior to that, Marc founded Diapers.com/Quidsi which sold to Amazon in 2011 for $550 million. As an investor, Marc announced his new venture firm, Vision Capital People, with his co-founder, Alex Rodrigues, earlier this year with $50M of Alex and Marc's own money. Fun fact, in 1996 Marc qualified to be in the US national bobsled team. In Today’s Episode with Marc Lore You Will Learn: 1.) How Marc made his way into the startup world, how he came to found Jet.com and what led to his most recent transition to the world of investing? 2.) How does Marc assess human potential? What does he mean when he says "the resume test"? What are the clearest signals of outperformers? What are signs of lack of performance? Why does Marc not believe in referencing? Does Mark start from a position of trust for it to be lost or with none and for it all to be gained? 3.) How does Marc evaluate his relationship to risk and fear? How has it changed over time? What did Marc's wife say when he left his safe job and put all their savings into his new business? What does Marc mean when he discusses finding "Sixth Gear"? How does Marc balance that intensity and ambition with romance and family life? 4.) Why does Marc believe Chief People Officer should be one of your first hires? What are the commonalities of the best Chief People Officers? What does the optimal relationship between CEO and CPO look like? How does Marc test for his core characteristics in interviews? What questions does he ask every candidate? What are the most revealing? 5.) How does Marc think about portfolio construction with the new fund today? Does Marc believe it is possible to take 40%+ of companies without alienating future investors? Is Marc concerned about over-capitalising companies too early? How does Marc think about reserves strategy and concentrating capital into the best companies?

Laela Sturdy is a General Partner @ CapitalG, Alphabet's independent growth fund with investments in the likes of Stripe, UiPath, Looker, Robinhood and Lyft to name a few. As for Laela, she joined CapitalG shortly after inception in 2013 and has led investments in Stripe, Duolingo, Gusto, UiPath and Unqork, to name a few. Prior to CapitalG, Laela was at Google as Managing Director of Emerging Businesses and held leadership roles within YouTube and search. In Today’s Episode with Laela Sturdy You Will Learn: 1.) How Laela made her way into the world of venture and came to be a General Partner at Alphabet's independent growth fund, CapitalG? 2.) The Market: With the rise of crossover funds, hedge funds, private equity, all entering growth stage venture, how does Laela analyse the current state of the market? How has the increase in capital supply impacted pricing at growth? How do CapitalG compete in a world where competitors pay 2x the valuation and have different outcome expectations? 3.) Portfolio Construction: Given CapitalG's single LP and evergreen structure, how do CapitalG think about portfolio construction? What is the right level of diversification? How doe CapitalG structure internal investment decision-making? How does this change for re-investments? How do CapitalG think about attribution internally? 4.) Upside and Downside: Given prices being so high, when outcome scenario planning, how does Laela think about good vs great when it comes to multiple expectations? How has this changed over time? On the flip side, how does Laela think about loss ratio at growth today? Has this changed with rounds becoming more and more pre-emptive? 5.) Scaling Unicorns: What are the commonalities in the biggest challenges founders face post-product-market fit but prescaling? What are the clear signs to Laela that a founder is uniquely skilled at hiring? Does Laela agree that the best founders do not need help on hiring? How does Laela feel about the future of venture being services platforms? Item’s Mentioned In Today’s Episode with Laela Sturdy Laela’s Favourite Book: The Great Gatsby Laela’s Most Recent Investment: Webflow

Jeff Lawson is the Founder & CEO @ Twilio, the company that allows you to unite communications and strengthen customer relationships across your business. Prior to their incredibly successful IPO in 2016 Jeff raised funding from some of the best including Bessemer, Union Square Ventures, Redpoint, Salesforce and Founders Fund to name a few. Before founding Twilio, Jeff was co-founder & CTO of NineStar, founding CTO of Stubhub.com, co-founder, CEO & CTO of Versity, and one of the first product managers for Amazon Web Services. In Today’s Episode with Jeff Lawson You Will Learn: 1.) How Jeff made his way into the world of tech and startups and what that founding a-ha moment was for Jeff with Twilio? When explaining new ideas to people, what signals to Jeff that the idea is resonating? Are there clear indicators an idea is not resonating? 2.) Leadership: What does great leadership mean to Jeff today? How has Jeff's leadership style changed and evolved over the years? What does Jeff believe is the key to great storytelling? How has the leadership style required, changed in a COVID world? What have been the biggest inflection points in his leadership? 3.) Culture: What does Jeff believe are the 3 key ingredients to company culture? How can leaders create a tribe that people associate with? What are the biggest lessons we can take from sport and religion when it comes to culture building? At what points has Jeff been concerned about the Twilio culture? What did he do to rectify it? Why are "values nice but principles better"? 4.) Decision-Making: How has Jeff created a culture of decentralised decision-making? What has Jeff done to ensure the best ideas rise to the top? In what ways can leaders ensure people feel safe to be bold and go big, without the fear of failure? How does Jeff determine when to give or remove resources from new ideas? How does Jeff think about the importance of "focus"? 5.) Diversity: Frank Slootman previously said, "diversity should not override merit". What are the core problems that Jeff has with this statement? How do Twilio construct their recruitment pipelines to ensure diversity? Why does Jeff believe the secret to human assessment is one of "miles travelled"? What are the signals of this? Item’s Mentioned In Today’s Episode with Jeff Lawson Jeff’s Favourite Book: Made to Stick: Why some ideas take hold and others come unstuck As always you can follow Harry and The Twenty Minute VC on Twitter here!

Mark Mullen is the Co-Founder of Bonfire Ventures, one of LA's leading early-stage funds, now on their 3rd Fund with $101M in the latest. In the past, Mark has invested in the likes of Trade Desk, Scopely, GOAT, ChowNow, Niantic and Pendo to name a few. Prior to co-founding Bonfire, Mark was a solo GP with Double M and then through Mull Capital, Mark is also an LP in other funds investing in 15 including the likes of Upfront, Freestyle, Backstage and Crosscut to name a few. In Today’s Episode with Mark Mullen You Will Learn: 1.) How Mark made his way into the world of venture, came to found Double M and why he decided he wanted to co-found Bonfire and be in a partnership, not a solo GP model? 2.) Portfolio Construction: With the new fund, how did Mark think about the right portfolio construction? What is the right level of diversification? How many lines should be in the portfolio? How important is ownership today? Is it possible to build ownership in your best companies over time? How does Mark think about proactive reserve allocation today? 3.) Investment Decision-Making: How does Mark think about the right investment decision-making structure with Bonfire today? How can one retain speed but also increase the number of decision-makers? How does Mark feel about the compression of fundraising timelines today? What advice does Mark give to founders when selecting their cap table? 4.) Boards and Time: How does Mark evaluate his own style of board membership? How has it changed over time? What do the best do on boards that makes them so great? How does Mark think about time allocation across the portfolio? Should you only spend time with winners? What have been some of his biggest lessons from this? Item’s Mentioned In Today’s Episode with Mark Mullen Mark’s Favourite Book: Undaunted Courage Mark’s Most Recent Investment: Topia As always you can follow Harry and The Twenty Minute VC on Twitter here!

Rishi Sunak was appointed Chancellor of the Exchequer on 13 February 2020. He was previously Chief Secretary to the Treasury from July 2019 to February 2020, and Parliamentary Under Secretary of State at the Ministry of Housing, Communities and Local Government from January 2018 to July 2019. He spent his professional career before politics in business and finance, working internationally. He co-founded an investment firm working with companies in multiple geographies and used that experience to help small and entrepreneurial British companies grow.  In Today’s Episode with Rishi Sunak You Will Learn: 1.) Rishi's first job was waiting table in a restaurant, what were his biggest takeaways from that first job? How did Rishi's time at Stanford impact his operating mindset today? How did Rishi make his way into the world of politics following a very successful career in finance? 2.) Talent: What does the UK need to do to become a global talent hub? How can Visa programs be reformed and innovated to ensure the UK is an attractive destination for the best talent? On reflection, where has the UK done well on talent and immigration? On the flip side, what has not worked? Why? What would Rishi have done differently? 3.) Entrepreneurs Relief & Capital Gains: What is the logic behind the removal of entrepreneurs relief? Why is it inefficient in its current form? How does Rishi think about using capital gains as a tool to attract the best to build and invest in the UK? Why does Rishi believe the UK is the most attractive place to build a business from a tax perspective? How does the UK compare to the EU and US? 4.) Driving Further Investment in the UK: What worked and what did not work with regards to "The Future Fund"? What would Rishi have done differently? What can Rishi and the UK do to encourage pension funds to invest more in venture moving forward? What are some elements the public assume the government can and should do, but in reality, you cannot? 5.) Rishi Sunak AMA: What does Rishi's morning routine look like? What time does Rishi wake up? What does he have for breakfast? What does the workout routine look like for Rishi? Who is his favourite Peloton instructor? Why? What is his guilty treat food-wise? How often does he have it? How did it feel for Rishi when he delivered his first budget? Was he nervous? How does Rishi deal with nerves today? Item’s Mentioned In Today’s Episode with Rishi Sunak Rishi’s Favourite Book: Roald Dahl As always you can follow Harry and The Twenty Minute VC on Twitter here!

Rafael Ilishayev is the Co-Founder & Co-CEO @ GoPuff, one of the market leaders delivering daily essentials in minutes. GoPuff's latest funding round priced the company at a reported $8.9Bn in March 2021 and to date, Rafael has raised over $2.4Bn for the company from the likes of Accel, Softbank, Fidelity, Baillie Gifford, D1 Capital and more. Rafael has scaled the company to over 550 US cities with over 7,000 employees nationwide. In Today’s Episode with Rafael Ilishayev You Will Learn: 1.) How Rafael made his way into the world of startups with the founding of GoPuff and how he turned it from a college delivery business into a nationwide leader with over 7,000 employees? 2.) Funding: Why did Raf wait until 2.5 years into the business before raising funding? What did that time bootstrapping the business teach Raf? How did it change his thinking on unit economics? How were GoPuff able to be EBITDA profitable from day 1? How do they have such superior margins in an industry blighted by low margins? 3.) New Markets: How does GoPuff determine attractive markets to scale into? What are the leading indicators of "good markets"? What resources are required to open new markets? What is the time to breakeven on new markets? How many micro-fulfilment centres does it take to win a new market? What are the biggest challenges moving into new markets? 4.) Competition: The market has become a lot more competitive, why does Raf feel this is not a market you can win without years of experience? What have they built that other new entrants do not have? Will this be a consolidatory landscape or will many of the new entrants die? Why is Raf planning to invest hundreds of millions into Europe over the coming years? 5.) Driver Efficiency & CACs: What have been Raf's biggest lessons when it comes to driver efficiency? How many deliveries does a driver need to make in one hour for the model to work? How does Raf think about the negative network effects of the model where the more demand, the longer delivery time? How can GoPuff prevent that? Item’s Mentioned In Today’s Episode with Rafael Ilishayev Rafael’s Favourite Book: Trillion-Dollar Coach: The Leadership Handbook of Silicon Valley's Bill Campbell As always you can follow Harry and The Twenty Minute VC on Twitter here!

Jay Simons is a General Partner @ Bond Capital, with their $1.25Bn debut growth fund in 2019 they made their mark on the venture landscape and have since made investments in the likes of Revolut, Canva, NextDoor, IronClad and my favourite, On Running. As for Jay, prior to entering venture, he spent an incredible 12 years at Atlassian including 9 years as President, playing an instrumental role in their hyper-growth journey. Jay is also a board member with both Zapier and HubSpot, two of my favourite SaaS companies. In Today’s Episode with Jay Simons You Will Learn: 1.) How Jay made his way into the world of startups following a stint as a pianist in Asia and how that startup journey led to his joining Bond on the venture side? 2.) Why does Jay believe the best companies build economies around themselves? What does this look like in reality? When is the right time for the company to start building these economies? As an investor, what are the signs that a founder is proactively thinking about this? What are some of the biggest mistakes people make when building economies? 3.) Why does Jay believe Partner/Channel networks can be so powerful? When is the right time to build out channel partners? What is the training framework for these partners before they can represent your products in market? How do channel partners change the internal structure and resource allocation for a company? What mistakes do people make with these partners? 4.) How does Jay think about when is the right time to build a second product? What were the biggest takeaways from his time at Atlassian on building product suites? How does Jay determine when is the right time to move upmarket into enterprise? How does this change in a world of product-led growth? 5.) Why did Jay decide now was the right time to move into venture with Bond? For what reasons did Jay choose Bond, over all the other firms? What have been the biggest surprises for Jay from his first 100 days in venture? What have been the most challenging elements? How did Jay embrace the common challenge of building the conviction to write the first check? Item’s Mentioned In Today’s Episode with Jay Simons Jay’s Favourite Book: The River Why Jay’s Most Recent Investment: Sentry As always you can follow Harry and The Twenty Minute VC on Twitter here!

Tony Xu is the CEO and Co-founder of DoorDash, the company empowering merchants to grow their businesses by offering on-demand delivery, data-driven insights, and better in-store efficiency. Prior to their IPO in December 2020, Tony raised over $2.5Bn for DoorDash from some of the best including Sequoia, Coatue, Softbank, Kleiner Perkins and DST, to name a few. Before co-founding the business in 2013, Tony worked in Product at Square, led special projects for the CEO and CFO at eBay, and began his career at McKinsey and Company. In Today’s Episode with Tony Xu You Will Learn: 1.) How did Tony make his way into the world of startups and what was that founding a-ha moment for Tony with the founding of DoorDash? What were Tony's biggest takeaways from seeing his parents work ethic at such a young age? How did it impact his operating mentality? 2.) Leadership Style: What does great leadership mean to Tony today? In what ways has Tony's leadership style changed over the DoorDash journey? How does Tony assess his own persistence and grit? Through what framework does Tony decide what to delegate vs what to control? 3.) Decision-Making & Risk: How does Tony evaluate his decision-making process today? What does Tony mean when he says, "you have to reduce the scope"? How does Tony think about understanding the interplay of different variants in a decision? Through what framework does Tony assess risk today? How has Tony's approach to risk and decision-making changed over time? 4.) Talent Acquisition: What have been Tony's biggest lessons in acquiring the best talent? What has worked well in the past? In what ways have they not acquired talent they should have acquired? What type of talent worked in the early days? How has that changed? Through what framework does Tony decide between a stretch VP and a stretch too far? 5.) Culture & Diversity: How does Tony think through the breakpoints in the scaling of culture? At what points did Tony feel the DoorDash culture was not what he wanted it to be? How did he react to change it? Through what process has Tony measured the success of DoorDash's diversity efforts? Which initiatives have worked? Are there any that have not? Item’s Mentioned In Today’s Episode with Tony Xu Tony’s Favourite Book: Score Takes Care Of Itself: My Philosophy of Leadership As always you can follow Harry and The Twenty Minute VC on Twitter here!

Eric Glyman is the Founder and CEO @ Ramp, the only corporate card and spend management platform designed to help you spend less. To date, Eric has raised over $390M for the company from some of the best including Thrive, Stripe, Founders Fund, Coatue and Box Group to name a few. Prior to changing the game of spend management, Eric founded Paribus, the price-tracking app that raised seed funding from General Catalyst and Greylock, which was acquired by Capital One in 2016. In Today’s Episode with Eric Glyman You Will Learn: 1.) Entry to Startups: How Eric made his way into the world of startups with Paribus and how that journey and exit led to his founding the recently minted unicorn, Ramp? 2.) Decision-Making: How does Eric deal with moments of intense pressure as a leader? How does pressure impact Eric's decision-making quality? Through what framework does Eric evaluate his decision-making process today? Why does Eric believe operational velocity is so key to company success? How does Eric determine between being fast vs spending real time on something? 3.) Funding Rounds: Why does Eric believe that "funding rounds are science experiments"? What should founders look to prove or disprove with each round? Why does Eric believe "you should never take the highest price"? What are the downsides? How does it impact employee stock options? Does it change investor sentiment? How does it change customer acquisition through referrals? 4.) The Rise of Crossover Funds: What does Eric make of the rise of crossover funds? In what way does their value differ to the value provided by traditional VCs? How does their communication style differ compared to traditional VCs? Does Eric worry about the signalling risk of having crossover funds invested early? Does Eric believe they will change the landscape of venture? 5.) Board Management: How does Eric analyse his style of board management today? How has it changed over time? Where does Eric believe many founders go wrong when it comes to board management? How can boards be used to bring together the wider team and company? What documents does Eric always prepare for the board? Item’s Mentioned In Today’s Episode with Eric Glyman Eric’s Favourite Book: John Wooden: The Legendary UCLA Coach's Top 20 Quotes As always you can follow Harry and The Twenty Minute VC on Twitter here!

Byron Deeter is a Partner @ Bessemer Venture Partners and one of the world's leading investors in SaaS and cloud. To date, nineteen of Byron’s investments are valued above $1 billion, including ten IPOs and counting. Some of the incredible companies within Byron's portfolio include Twilio, ServiceTitan, Hashicorp, Canva, Intercom, DocuSign, SendGrid, the list goes on. Prior to joining the world of venture, Byron was an entrepreneur, raising a Series A from Bessemer and scaling the company to be one of the first global SaaS companies, reaching profitability and successfully selling to IBM. CLICK TO LISTEN ON ITUNES In Today’s Episode with Byron Deeter You Will Learn: 1.) How Deven made his way into the world of venture and how that led to his becoming a Managing Director @ Insight, way back in 2000? 2.) The Market: Many people passed on Twilio, what did Byron see that others did not? Did Byron have concerns around the TAM? What made Byron feel comfortable they were not too early? How did Byron assess whether customers would churn off Twilio when they scaled to a size they could build their own infrastructure? How does Byron advise founders on this challenge today? 3.) The Team: What did Byron find some compelling about Jeff so early on? Jeff has been an incredible CEO from pre-seed to post-IPO, what has enabled Jeff specifically to scale with the company so successfully? What does Byron do to build the trust and rapport with founders that he does? What works? What does not work? How does that look today with Zoom? 4.) The Incumbents & Competition: Why does Byron believe the incumbent advantage is actually an incumbent disadvantage? What specifically has Byron found underwhelming about how the incumbents have tried to respond? In what tangible and specific way are startups better placed to win than incumbents? How does Byron advise founders to assess other startup competitors? 5.) The Funding: Twilio is Bessemer's single largest position ever, how does Byron know when is the right time to double down on an investment? What signals does he look for? Has this changed with the massive price inflation we have seen over the last year? How does Byron analyse the influx of new capital? Where is it good? What are the challenges to it? Item’s Mentioned In Today’s Episode with Byron Deeter Revolut Business is a financial super app for all things business. It’s a super easy, powerful and personalised account that gives you control over all your business finances and processes in one place. Joining Revolut Business lets you send and receive money at the interbank rate, with no hidden fees as well as opening accounts in more than 28 currencies. You can also streamline your business processes by integrating all your apps or plugins, like accounting and expenses, and manage it from one place. You get more control over your day-to-day business finances, processes and management which means you can focus on your actual business goals. I’ve partnered with Revolut Business to bring you an exclusive 2-month paid plan for free, so you can move your business forward. Click here to claim your free 2-month trial and get started. As always you can follow Harry and The Twenty Minute VC on Twitter here!

Nigel Morris is the Co-Founder and Managing Partner of QED Investors, one of the leading fintech-focused venture firms of the last decade with numerous unicorn investments, including Credit Karma, NuBank, Avant, SoFi, Klarna, GreenSky, and AvidXchange. Prior to QED, Nigel co-founded Capital One Financial Services in 1994. During his 10-year tenure, Nigel transitioned Capital One from an emerging start-up to an established public company valued at over $20 billion with over 15,000 employees. Finally, Nigel also sits on or has sat on the board of Nubank, Prosper, Zopa, Klarna, The Economist and London Business School to name a few. In Today’s Episode with Nigel Morris You Will Learn: 1.) How Nigel made his way into the world of startups with Capital One back in 1994 and how that journey led to his founding one of the leading fintech investment firms in QED? What made Nigel want to develop QED from a family office into a large scaling venture firm? 2.) Where does Nigel's passion for mental health stem from? Why does Nigel believe VC and entrepreneurship is riddled with mental health problems? How does Nigel deal with his own self-doubt and insecurity? In what way does Nigel analyse his own relationship to money today? How has it changed over time? How has that relationship to money changed how he thinks about investing? 3.) What does Nigel believe it takes to be a great listener? How does Nigel think about asking the risk questions to move the founder to the right insight? How does Nigel create the conditions where the entrepreneur can be much more open? What questions would Nigel never ask? How does Nigel describe his style of board membership? How has it changed? 4.) How does Nigel think about the centrality of unit economics? What does Nigel look for in the way that the entrepreneur thinks through and analyses unit economics? When does Nigel believe you have tangible data to rely on to justify unit economics? What is the biggest challenge with unit economics? What should companies do when their competitors raise massive funding rounds? 5.) Why does Nigel believe that "bundling" is a canard? What does not work regarding how traditional "bundling" works? Why might it be different for the next generation of fintech providers to bundle different products? Why does Nigel believe lending is a much harder insertion point to start than current accounts? How does Nigel think about the right insertion point? Item’s Mentioned In Today’s Episode with Nigel Morris Nigel’s Favourite Book: Leadership and the New Science: Discovering Order in a Chaotic World Nigel’s Most Recent Investment: Bitso As always you can follow Harry and The Twenty Minute VC on Twitter here!  

José Neves is the Founder, CEO & Chairman @ Farfetch, the #1 destination for high-end fashion offering the world's Greatest Selection of Luxury. Now a public company, José has raised over $1.7Bn with Farfetch from some of the biggest names including Alibaba, Richemont, JD.com, Index Ventures and DST to name a few. Prior to Farfetch, José has been involved in the fashion start-up world since the mid-1990s when he launched footwear business SWEAR. José later founded SIX London, a fashion licensing and wholesale company selling to 600 retailers worldwide. Finally, in 2001 José opened the renowned boutique bstore, which won the British Fashion Award for Retailer of the Year in 2006. In Today’s Episode with José Neves You Will Learn: 1.) How José made his way from creating footwear brands in the days of the Spice Girls and cyberpunk to changing the fashion industry itself with Farfetch? 2.) Why does Zen Buddhism resonate with José in such a profound way? How does his adoption of it impact his style of leadership today? How does José deal with the loneliness of being a CEO? What does José mean when he says the most successful leaders, "know how to fall and how to get up"? How has José responded to his greatest failures? 3.) How does José think about decision-making today? What are the biggest misconceptions people have with regards to effective decision-making? Why is head vs heart the wrong way to think about decision-making? How does José adopt a sense of emotional detachment when making decisions? What works? What does not work? 4.) How does José evaluate his relationship to money today? In what ways has it changed over time? What does José believe that others do not believe when it comes to risk and risk management? How does José balance the demands of Wall St and investors with the knowledge that everything is inherently uncertain? 5.) Does José ever feel self-doubt? How does he manage it? In what ways does he advise earlier stage founders to grapple with their own self-doubt? How does José think about tying one's own identity to their company? Why is this so dangerous? Item’s Mentioned In Today’s Episode with José Neves José’s Favourite Book: The Master and His Emissary: The Divided Brain and the Making of the Western World As always you can follow Harry and The Twenty Minute VC on Twitter here!

Deven Parekh is a Managing Director at Insight Partners, one of the leading investing franchises of the last 25 years with $30Bn+ in capital commitments, 400+ primary investments and over 200 portfolio acquisitions. Deven himself has made more than 90 investments since joining in 2000 including in the likes of Twitter, Alibaba, JD.com, Chargebee and Automattic (WordPress) to name a few. Deven also sits on the boards of Checkout.com, Calm, Saks.com, Optimizely and 1stDibs, again naming a few. If that was not enough, Deven also serves on the Board of the Carnegie Endowment for International Peace and the Board of the Tisch New York MS Research Center. As a result of his investing success, Deven has been named on Forbes Midas List 5 time and has been selected as a Top 100 Venture Capitalist by CB Insights 4 times. In Today’s Episode with Deven Parekh You Will Learn: 1.) How Deven made his way into the world of venture and how that led to his becoming a Managing Director @ Insight, way back in 2000? 2.) How does Deven analyse the current fundraising mania? Does portfolio discipline and temporal diversification matter anymore? How has Deven and Insight seen the velocity of fundraises change over the years? What can Deven and Insight do to get compress their decision-making timeliness with the compression of fundraising timelines? 3.) How does Deven assess his relationship to price and price sensitivity? What have been some core lessons for Deven when comparing deals that they did which were "cheap" vs "expensive"? How do Insight think about required levels of ownership today? Does Deven believe it is possible to build ownership over time? What is required to do so? What are the challenges? 4.) How would Deven describe his style of board membership today? How has it changed over time? What advice does Deven have for younger board members scaling into the role? How does Deven think about his time allocation across the portfolio? What is the optimal? How does this differ from reality? Why do your winners never need you? 5.) How does Deven evaluate his own insecurities and self-doubt today? In what way have these changed over time? How does Deven analyse the "weight of his words" within Insight? How does Insight structure the internal decision-making process to ensure that everyone's voice is heard? In what ways can firms foster that security for young partners to feel they can bring anything to the table? Item’s Mentioned In Today’s Episode with Deven Parekh Deven's Favourite Book: What We Know About Climate Change (The MIT Press), Draft No. 4: On the Writing Process Deven’s Most Recent Investment: TetraScience As always you can follow Harry and The Twenty Minute VC on Twitter here!

Ryan Smith is the Founder and Executive Chairman @ Qualtrics, the leader in customer experience and creator of the experience management (XM) category. Ryan has grown the company from a basement startup to one of the fastest-growing technology companies in the world, with 25 offices globally and more than 13,000 customers. Qualtrics raised $400M in funding from Accel, Sequoia, and Insight Venture Partners. Three days before the company was initially scheduled to go public, SAP announced its intent to acquire Qualtrics for $8B, which was the largest private enterprise software acquisition ever. In 2020, Qualtrics and SAP announced plans to take Qualtrics public as an independently operated company. In Today’s Episode with Ryan Smith You Will Learn: 1.) How Ryan made his way into the world of startups having travelled the world and came to found Qualtrics in his basement over 21 years ago? 2.) How does Ryan think about his relationship to happiness and what it means to "be happy"? How does Ryan think about identity and founders aligning their identities to their company? How does Ryan think, if not careful, tech can eat you up? What does Ryan mean when he says he would rather be "opportunistic than an entrepreneur"? 3.) How does Ryan approach decision-making today? In what situations does Ryan think with his head vs his heart? How does Ryan approach risk today? How has his relationship to risk changed over time? What did the sale process to SAP look like? What was that decision-making process to sell to SAP for $8BN in cash vs IPO? What advice did his wife give him? 4.) How does Ryan evaluate his relationship to money today? How did it feel when Ryan sold Qualtrics to SAP for $8BN in cash? How does Ryan think about giving his children the right mentality and upbringing while being brought up in extreme wealth? What are the challenges of doing so? 5.) How does Ryan think about the weight of responsibility? Ryan and his brother Jared, did a lot very young, did Ryan feel the pressure of having to grow up faster than one usually would? How did that impact his mentality? How did Ryan's travels to Mexico and Japan change the person he is today? Item’s Mentioned In Today’s Episode with Ryan Smith Ryan’s Favourite Book: Alchemist: A Fable about Following Your Dream As always you can follow Harry and The Twenty Minute VC on Twitter here!

Marcos Galperin is the Founder and CEO @ MercadoLibre, one of LATAM's most successful companies of the last 2 decades. Today MercadoLibre's market cap exceeds $78Bn and the business includes everything from commerce to payments to logistics. Marcos is widely considered one of the great entrepreneurs of the last 2 decades scaling the business from its founding in 1999 while in business school at Stanford to today, a leader in LATAM operating across 18 countries and plans to end 2021 with over 32,000 employees. In Today’s Episode with Marcos Galperin You Will Learn: 1.) How Marcos made his way into the world of startups and came up with the idea for MercadoLibre while at Stanford Business School? 2.) Talent Acquisition and Retention: What have been some of Marcos' biggest lessons on what it takes to acquire A* talent? Does Marcos believe individuals can scale across company stages? When is a stretch hire a stretch too far? What has been the secret to Marcos having such a retained leadership team? What works? What does not? 3.) Risk and Decision-Making: How does Marcos evaluate his relationship to risk today? What frameworks does Marcos use to make effective decisions today? How does Marcos think about short term vs long term when it comes to resource allocation? How does Marcos prioritise where he makes decisions vs where he is willing to delegate? 4.) Funding and The Crash: How does Marcos reflect on his biggest lessons from going through 2 crashes with MercadoLibre? How did he change the way he ran the business post crash? How does Marcos advise founders today when big rounds are on offer, take the money or wait? What other components are important to consider in this decision? Item’s Mentioned In Today’s Episode with Marcos Galperin Parker’s Favourite Book: Built To Last: Successful Habits of Visionary Companies As always you can follow Harry and The Twenty Minute VC on Twitter here!

David Tisch is the Founder and Managing Partner @ Box Group, one of the leading seed focused firms of the last decade with a portfolio including Airtable, Glossier, PillPack, Plaid and many more. Prior to founding Box, David was Managing Director of Techstars New York and was a prolific angel investor making early angel investments in the likes of Vine and Warby Parker to name a few. In Today’s Episode with David Tisch You Will Learn: 1.) How David made his way into the world of tech and startups and came to change the state of seed funding in NYC with the founding of Box Group? 2.) Why does David believe that ownership requirements are "VCs projecting their problems on founders"? Why does David believe that ownership today fundamentally does not matter? How does David feel about his own relationship to price? Why is it important to be price aware across the portfolio, not on a per deal basis? 3.) What does David make of the rise of pre-emptive rounds? How does David advise portfolio founders who have them on the table? What other arguments does David use to founders contemplating taking seed rounds from multi-stage funds? How does David believe founders should assess their importance to the fund investing in them? 4.) How does David feel about his relationship to FOMO today? What have been some of his biggest misses in recent years? How have some of his biggest misses changed how he acts as an investor today? How have some of his biggest successes changed his investing lens? What changes did David and Box make to their decision-making process as a result? 5.) What does David believe are the biggest mistakes to turn down a company? Why is "too early" never a reason to turn down a company? How does David assess and think about market size today? Through what framework does David evaluate and assess competition today? What does David believe are some core concerns that are reasonable to turn down an opportunity? Item’s Mentioned In Today’s Episode with David Tisch David’s Most Recent Investment: Ramp As always you can follow Harry and The Twenty Minute VC on Twitter here!

Chris Fralic is a Board Partner @ First Round Capital, one of the leading seed-stage venture firms of the last decade with investments in the likes of Uber, Square, Notion, Warby Parker and more. As for Chris, he has led deals in Roblox, Ring.com, HotelTonight, Rec Room and many more incredible companies. Prior to the world of venture, Chris was VP of Business Development at social bookmarking and tagging company del.icio.us through the Yahoo! acquisition. He was also one of the early employees at Half.com and after the eBay, acquisition spent six years with eBay in a variety of business development, media and entertainment roles. In Today’s Episode with Chris Fralic You Will Learn: 1.) How did Chris come to first meet Dave and the team at Roblox? Where was the first meeting? Who was in attendance? How did Chris feel post that first meeting with the team? 2.) Turning the company down: Why did First Round turn down Roblox on first look? How does Chris assess his own relationship to price? Through what mechanism does he determine whether to pay up or not? How does Chris retain relationships with founders when saying no? Does Chris believe you can buy up ownership post first check today, with the capital proliferate we have? 3.) What does Chris mean when he discusses the lessons from First Round's portfolio when it comes to "slow bake vs fast bake"? How did the First Round partnership analyse the Uber, Square, Roblox portfolio at the time? Through what framework does Chris think about reserves management given the challenge of "slow bake companies"? How does he address it today? 4.) What does Chris mean when he discusses the hype to substance ratio? Why is it more important than ever today? What does this mean for startups? How can startups with a low hype to substance ratio raise funds at good prices? What advice does Chris have for them? How does Chris think about the importance of firm and individual brand in venture today? 5.) How has Chris seen Dave evolve as a leader and CEO over time? What caused the changes in his leadership style? What moments stand out as the most challenging moments to Chris in the scaling of Roblox? Who does Chris believe are the behind the scenes rockstars that made Roblox possible? As always you can follow Harry and The Twenty Minute VC on Twitter here!

Parker Conrad is the Founder and CEO @ Rippling, the employee management platform allowing you to manage your employees' payroll, benefits, devices and more—in one place. To date, Parker has raised over $197M for Rippling from the likes of Founders Fund, Kleiner Perkins, Initialized, Bedrock, Greenoaks and Coatue. Prior to founding Rippling, Parker was the Co-Founder and CEO @ Zenefits and if that was not enough, Parker is also a prominent angel having invested in the likes of Census, Pulley and then also AgentSync and TrueNorth, alongside 20VC Fund. In Today’s Episode with Parker Conrad You Will Learn: 1.) How did Parker make his way into the world of technology and startups? What was the founding a-ha moment for Parker with Rippling? How did his journey with Zenefits change or alter his leadership style today with Rippling? 2.) Why does Parker believe that the conventional advice of focus, focus, focus is BS? What does Parker mean when he states, "The Compound Startup"? How does the approach of the compound startup differ from traditional approaches of product and company building? What are the core benefits of using the compound startup approach? 3.) How does Parker think about providing sufficient product quality with an increasing breadth of product offering, entailed within a compound startup? In what way does pricing differ when comparing compound startups to traditional startups? How can compound startups optimise their pricing on a bundle basis? What has Slack and Microsoft taught us about this? 4.) Why does Parker disagree with the conventional analogy of the VC <> founder relationship being a marriage? Why does Parker refer to it more as a "General Contractor" relationship for a house? What can founders do to sufficiently protect themselves from overarching VCs? What can VCs do to be the very best partners to the founders they work with? 5.) How does Parker evaluate his relationship to money today? How has it changed over time? What does Parker know now that he wishes he had known at the start of his founding of Rippling? What have been Parker's biggest lessons on talent acquisition? Why did Parker decide to bring on a COO when he did? How has it changed his role? Item’s Mentioned In Today’s Episode with Parker Conrad Parker’s Favourite Book: Matilda by Roald Dahl As always you can follow Harry and The Twenty Minute VC on Twitter here!

Peter Reinhardt is the Founder and CEO @ Segment, the leading customer data platform with over 20,000 companies using Segment to collect, clean, and control their customer data. Prior to their $3.2BN acquisition by Twilio in 2020, Peter raised over $283M for Segment from Accel, Thrive, Meritech, GV, General Catalyst and Kleiner Perkins to name a few. Peter is also an active angel investor having made investments in the likes of Retool, Newfront, Pilot and more. In Today’s Episode with Peter Reinhardt You Will Learn: 1.) How Peter made his way into the world of startups and how he came to found a company, Segment, by actively trying to prove to his co-founder that it would not work? Why does Peter believe the Airbnb story is the most destructive myth for founders to follow? 2.) Learning: How does Peter think about learning frameworks for new topics? How does he construct his? How does Peter use data within this learning process to increase his rate of learning? Where do the majority of people go wrong in constructing their framework for learning? 3.) Listening and Debate: What does Peter believe is required to be "a good listener"? What questions do the best listeners ask? What tone do they use to ask these questions? How does Peter create an environment of safety internally where people feel they can debate? How does one balance between debate and thinking vs putting those thoughts into action? 4.) Problem-solving: How does Peter breakdown problems into their component parts? Through what mechanism does he determine what to prioritise first? How would Peter describe his decision-making process? How does he determine between head vs heart in decisions? In what way does Peter use data to further inform the decisions he makes? 5.) How would Peter describe his management style today? Has it changed over time? In what way has working with a coach changed the way Peter thinks about leadership? What elements do they focus on? How often does he see his coach? What have been some of his biggest takeaways? Item’s Mentioned In Today’s Episode with Peter Reinhardt Peter’s Favourite Book: The Chalice and the Blade, Crucial Conversations As always you can follow Harry and The Twenty Minute VC on Twitter here!

David Sze is a General Partner @ Greylock where he has led some of the firms most notable investments including Facebook, LinkedIn and Pandora. David has consistently been at the forefront of innovation in the consumer landscape leading to his investments in Discord, Roblox, Medium and more. Prior to Greylock, David was SVP of Product Strategy at one of the first search pioneers, Excite and then Excite@Home. Before Excite, he was in interactive entertainment — in product marketing at Electronic Arts and development at Crystal Dynamics. As a result of his incredible investing track record, David has been frequently named to the Forbes Midas List.  In Today’s Episode with David Sze You Will Learn: 1.) How David made his way into the world of venture and came to lead consumer investing at Greylock with investments in Facebook, Linkedin, Roblox and Discord? 2.) How did David's investments in Facebook and Linkedin challenge Greylock's investment strategy at the time? Paying $500M for Facebook, how does David reflect on his own relationship to price and price sensitivity? How does David evaluate the rise of pre-emptive rounds today? Is David concerned by the excess supply of capital in the market today? 3.) Having worked with Mark @ Facebook, Reid @ Linkedin, David @ Roblox, what are the commonalities of these incredible founders? What does David do to build relationships of trust and vulnerability with founders? How does David do this in the compressed fundraising timelines we have today? 4.) The Partnership: What does David believe Greylock have done well in terms of creating an environment of safety within the partnership where people can really challenge each other? What works? What does not? For younger VCs, what is the difference between those that succeed and those that do not? What is David's biggest advice to those in the earlier years of their VC career? 5.) The Board: How does David evaluate his own style of board membership today? How has it changed over the years? What does David believe are his biggest strengths and his biggest weaknesses as a board member? What advice does David give to younger VCs assuming their first board roles? As always you can follow Harry and The Twenty Minute VC on Twitter here!

Wade Foster is the Co-Founder & CEO @ Zapier, the company that moves info between your web apps automatically, so you can focus on your most important work. Post YC in 2012, Wade raised $1.4M for the company from Bessemer and Threshold but since that round, he scaled the company to $140M in ARR and a $5Bn valuation with Sequoia and Steadfast buying out some early investors earlier this year. In Today’s Episode with Wade Foster You Will Learn: 1.) How Wade made his way from email marketing manager to founding one of YC's most successful alum in the form of Zapier? Does Wade agree with the "fake it till you make it theory"? How does Wade advise grads on starting a company vs joining a startup vs joining an incumbent? 2.) Remote Work: Zapier has been remote since 2012, what do Zapier do very specifically that Waade believes has enabled them to be so successful remote? What did not work? What were some of the biggest challenges of scaling the team remotely? In terms of tooling, what specific tools do Wade and Zapier use to make the org as transparent as possible? 3.) In the scaling journey, what have been the most significant breakpoints in the org scaling? How has Eade scaled his style of leadership? What has been the most challenging element to scale? How does Wade structure internal meetings? Who is invited to what? What materials are shared? How are the meetings structured? 4.) Why did Wade decide not to take the venture path and scale the company from revenues? What does Wade believe so many founders misunderstand when it comes to fundraising? What does Wade believe they gained from the bootstrapped approach? Why did Wade still maintain relationships with VCs? How did he choose those he wanted to stay in touch with? 5.) How does Wade feel about his relationship to money? What does Wade think about the rise of secondaries? In what framework does Wade advise founders who have the chance to take secondaries? What is the right amount to take off the table? How does one communicate this? Item’s Mentioned In Today’s Episode with Wade Foster Wade’s Favourite Book: Harry Potter As always you can follow Harry and The Twenty Minute VC on Twitter here!

Nikolay Storonsky is the Founder & CEO @ Revolut, one of the world's largest and fastest-growing fintechs offering everything from personal to business banking, providing a better way to manage your money. To date, Nikolay has raised over $905M with Revolut from Ribbit, Index, DST, Balderton and Bond Capital to name a few. Nikolay has scaled Revolut to over 2,000 employees across 4 continents. Before changing the world of neo-banking, Nikolay spent 8 years as a derivatives trader at both Lehman Brothers and Credit Suisse in London. In Today’s Episode with Nikolay Storonsky You Will Learn: 1.) How Nikolay made his way into the world of startups from derivatives trading and how that led to his changing the world of fintech with Revolut? 2.) How would Nikolay describe his style of leadership today? How did his time in banking impact his operating style? What elements has Nikolay found the hardest to scale into as a leader? How does Nikolay assess his relationship to ambition? What drives him today? How does Nikolay deal with self-doubt and vulnerability in leadership? 3.) Why does Nikolay feel the most important thing in a company is the speed of product shipment? From a product perspective, how does Nikolay determine what to do next vs what to do later? What does that prioritisation process look like? Has it changed over time? 4.) How does Nikolay think about gepgraphic expansion today? Given Monzo's challenges in the US, why did Revolut decide the US remained a good strategy? What does it take to launch and scale a new country? How does Nikolay think about the relationship between growth and profitability? What companies does Nikolay admire most for their international scaling? Item’s Mentioned In Today’s Episode with Nikolay Storonsky Nikolay’s Favourite Book: Principles by Ray Dalio (PDF) As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Guillaume Pousaz is the Founder and CEO of Checkout.com, one of the world's leading global payments solutions providers and one of Europe's most valuable private companies. Guillaume founded Checkout.com in 2012 and bootstrapped the business until its record-breaking $230M Series A led by Insight and DST in 2019. Since, Guillaume has raised a further $600M for Checkout from the likes of Coatue, Tiger, Blossom, GIC and Greenoaks. As part of this process, Guillaume has scaled the team to over 900 people around the world and Checkout as one of the category leaders in payments with a reported $15Bn valuation. In Today’s Episode with Guillaume Pousaz You Will Learn: 1.) How Guillaume made his way into the world of payments following a travelling experience? How that experience led to his founding the now $12Bn, Checkout.com? 2.) Why did Guillaume wait 7 years into the running of the business before raising a massive $230M Series A? Why was then the right time? Was it a difficult mental transition to move from lean, capital efficiency to raising $230M? Why have Checkout never spent a single dollar on marketing? Is it true, Checkout has never spent a single dollar you have raised? 3.) What does Guillaume mean when he says he "has 3 roadmaps for life"? How does he structure his planning for the next 2,5 and 10 years? How does Guillaume think on his own identity and how it is tied to Checkout, the company? How does Guillaume advise founders in terms of tying their identity to their company? 4.) Why does Guillaume believe that becoming a father made him a better CEO? How did it impact his operating style? How does Guillaume analogise the role of the CEO to the profession of being a sailor? How does Guillaume think through his relationship to money today? How has it changed over time? How does he think about ensuring it does not impact his children? 5.) In what way does Guillaume structure his decision-making process today? What does Guillaume believe it is about the velocity of decisions that determine the quality of the leader? What topics does Guillaume struggle to make fast decisions on? What advice does Guillaume give to founders in situations when you just do not know what to do? Item’s Mentioned In Today’s Episode with Guillaume Pousaz Guillaume’s Favourite Book: Dune by Frank Herbert As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Olivier Pomel is the Founder & CEO @ Datadog, the company building the next generation of tools for DevOps teams. Prior to their incredibly successful IPO in 2019, Olivier raised over $147M for the company from Index, ICONIQ, Meritech, IA Ventures, Amplify and OpenView, to name a few. Prior to founding Datadog and changing the world of devops, Olivier was a VP with Wireless Generation for 8 years leading an engineering team of close to 100 of the best developers in NYC. In Today’s Episode with Olivier Pomel You Will Learn: 1.) How Olivier made his way into the world of startups and what was the a-ha founding moment for his creating of Datadog, changing the world of devops? 2.) Why does Olivier believe that "short term failure is a source of long term success?" Why did both seed and Series A investors not get Datadog? What would Olivier have done differently if fundraising again? What do investors misunderstand today when investing in big markets looking for the "entry wedge"? 3.) What has been Olivier's biggest learnings on how to run Datadog during a pandemic? What attributes does Olivier look for when hiring senior leaders? Why does Olivier believe the CEO has to be the "equaliser in chief"? What does that mean in practice? How can leaders creat eenvironments of safety where their team can approach them with anything? 4.) What have been the biggest challenges in moving from a single product to a multi-product company? How does one know when is the right time to add additional products? What is Olivier's decision-making process to determine which products to build next? 5.) How does Olivier assess his relationship to money today? How has it changed over time? In what ways has becoming a father impacted Olivier's operating mindset? What 3 traits would Olivier most like his children to adopt? Item’s Mentioned In Today’s Episode with Olivier Pomel Olivier’s Favourite Book: Kurt Vonnegut As always you can follow Harry and The Twenty Minute VC on Twitter here!

Linda Lian is the Co-Founder and CEO @ CommonRoom, the place where your organization and your community come together. To date, Linda has raised over $50M with CommonRoom from the likes of Danny Rimer @ Index Ventures, Sarah Guo @ Greylock, Dylan Field @ Figma, Dick Costolo and of course 20VC Fund. Prior to changing the world of community though, Linda spent close to 3 years at Amazon as a Senior Product Manager on AWS and Alexa. Before Amazon, Lida was on the other side of the table in venture as an associate at Madrona. In Today’s Episode with Linda Lian You Will Learn: 1.) How Linda made her way into the world of startups and came to start on the venture side with Madrona? How did Linda's time at Amazon shape her thinking around founding CommonRoom? What were Linda's biggest lessons from her time at Amazon and then also being mentored by Jeff Weiner 2.) How does Linda describe her leadership style today? What are the biggest lessons Linda has learned in terms of how to speak with compassion but also directness and clarity? Why is Linda not a fan of "the shit sandwich"? What is the most effective way to give feedback? 3.) What did Linda decide to only hire senior and experienced individuals with CommonRoom? What are the benefits of doing so? What are the downsides? How does Linda approach hiring such senior talent? What works? How is this also challenging? What does Linda mean by "the long poach"? 4.) How does Linda approach delegation today? What framework does Linda use to determine what to do vs what to delegate? How does Linda approach head vs heart when it comes to decision-making? What does it take for Linda to change her mind? What is required? 5.) What does Linda believe are the biggest misnomers around the search for product market fit? Why did Linda deliberately choose to stay in stealth despite raising over $50M from some of the world's best investors? How did that impact their ability on both product and customer discovery? As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Peter Fenton is a General Partner @ Benchmark, one of the great venture firms of the last 3 decades with a portfolio including the likes of SNAP, Twitter, eBay, New Relic, Stitchfix and many more. As for Peter, he has led deals, sits or has sat on the boards of Elastic, New Relic, Digits, Docker, Optimizely, Yelp and Zuora to name a few. Prior to Benchmark, Peter was a General Partner @ Accel Partners in San Francisco. As a result of his incredible track, Peter has been on the Forbes Midas List more times than I have done podcast episodes! In Today’s Episode with Peter Fenton You Will Learn: 1.) How a round of golf led to Peter Fenton leading the New Relic Series A? What did the deal look like both in check size and valuation? What does Peter think that round would be in today's market? 2.) How does Peter create an environment of safety with entrepreneurs where they feel they can be vulnerable with him? How does Peter approach building relationships of trust in compressed fundraising timelines? In what way has Peter seen relationships go bad? What can been done to mitigate that and optimise the Founder <> VC relationship? 3.) How does Peter assess market timing when making investments today? What does Peter mean when he says, "you have to understand whether you are unlocking consumption"? What does unlocking consumption look like in reality? How does Peter think about positive or negative externalities that could impact the business? 4.) Does Peter agree with Bill Gurley that the biggest challenge today is the "oversupply of capital"? Where does the oversupply of capital become a real challenge? What does Peter advise growth-stage founders do to prevent this from damaging them? How does Peter think about capital efficiency in the companies where he is on the board? 5.) What were Peter's biggest lessons on what it takes to be a great board member from his 12 years at New Relic? How did he see his style of board membership change? On the founder side, how do the very best founders manage and navigate their board? What do most boards misunderstand or mismanage? Item's Mentioned In Today's Episode with Peter Fenton Peter's Favourite Book: Nonviolent Communication: A Language of Life As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

David Velez is the Founder & CEO @ Nubank, one of the fastest growing digital banks in the world with operations in Brazil, Mexico, Argentina and Colombia. To fuel this growth, David has raised over $1.5BN for Nubank from some of the best in the business including Doug Leone @ Sequoia, Micky @ Ribbit, Thrive, Founders Fund, DST, Tiger and more. Before changing the world of LATAM finance, David was a Partner @ Sequoia where he was responsible for all LATAM investments. Prior to Sequoia, David was the co-founder of General Atlantic's South American investment programme. In Today’s Episode You Will Learn: 1.) How David made his way into the world of startups through becoming a Partner @ Sequoia? How that led to his founding of Nubank? How his time at Sequoia impacted how he thought about building Nubank? 2.) How does David think about the relationship between growth and quality in company scaling? When scaling so fast, what are the first things to break? How does one know when is the right time to expand geographically? What is the right thought process to go through when determining how to know when is the right time to expand product lines? 3.) Looking at the market today, how does David for-see the future of digital banks? Will we seen increased consolidation over the coming years? How does David think through the verticalisation of neo-banks? What does the reduction in barriers to creating neo-banks really mean? How did Nubank scale to the scale it is today with $0 CACs? 4.) How has David seen his leadership style change with the growth of the company? Why does David feel it is wrong that the titles of Founder & CEO are so inextricably linked? What element of being a great founder are actually not good for CEOs to have? What elements of great CEOs are bad for founders to have? What has David found the hardest to scale in himself? 5.) How does David use "the responsibility framework" when making decisions today? What are David's thoughts on imposter syndrome within leaders today and how it can be harnessed for good? How does David approach head vs heart when it comes to decision-making today? Does David engage with regret minimisation as part of this? Item’s Mentioned In Today’s Episode David’s Favourite Book: One Hundred Years of Solitude As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jeremy Levine is a Partner @ Bessemer Venture Partners, one of the leading venture firms of the last 2 decades with a portfolio including the likes of Pinterest, Shopify, LinkedIn, Yelp, Twilio and many more. As for Jeremy, five of his early-stage investments—LinkedIn, MindBody, Pinterest, Shopify and Yelp—grew into billion-dollar publicly traded companies. As a result of his incredible portfolio, he has featured on the Forbes Midas List for several years running. In Today’s Episode with Jeremy Levine You Will Learn: 1.) How Jeremy came to make one great decision and make one big mistake all in one rainy afternoon in Palo Alto? What was the story behind meeting the Pinterest team for the first time? Who was there? How did it go down? 2.) Market: How did Jeremy analyse the market at the time of the investment? What had been some core lessons Jeremy had learned on what made successful user-generated content plays? Where was Jeremy wrong in how he analysed the market? In what way is Jeremy surprised with how the market evolved? How does Jeremy analyse market timing today? 3.) Team: Jeremy has previously called Ben Silberman a "product visionary", what made Jeremy say this about Ben? How did Jeremy get over the concern of many VCs that Pinterest did not have a technical co-founder? Having seen Ben change over the last decade, what have been the biggest changes in Ben's leadership style over the last 10 years? 4.) Traction: When evaluating traction, where does Jeremy think so many investors make mistakes today? How should founders determine what is their core North Star metric? What gave Jeremy the confidence Pinterest could "cross the chasm"? How did the early Pinterest cohorts look both from usage and retention? What elements surprised and impressed? 5.) Pre + Post Mortem: What did Jeremy see as the likely reasons why Pinterest would not work? How did Jeremy think through what it took for UGC platforms to monetise at the time? Where was he wrong here? What did Jeremy see as the upside? What did he believe Pinterest could be if all the stars aligned? As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jason Fried is the Founder & CEO @ Basecamp, the project management and team communication tool trusted by millions. Over an incredible 22 year journey, they have scaled to over 3.5M accounts and in 2020 they went back to being a multi-product company with the launch of their integrated email client & service, HEY. Jason is also the co-author of the widely acclaimed, ReWork and has also made several angel investments in the likes of Intercom, Gumroad and Hodinkee to name a few. In Today’s Episode You Will Learn: 1.) How Jason Fried made his way into the world of startups and came to found one of the leading project management and team communications tools in the form of Basecamp? 2.) How does Jason analyse and evaluate his relationship to money? Why does Jason believe that he has this inherent downside protection when it comes to money? How does he structure his personal finances between stocks, cash, crypto etc etc? What have been some of Jason's biggest lessons when it comes to tying happiness to monetary levels? 3.) What does Jason mean when he says, "I have a fantasy of getting fired"? How does Jason think about knowing when is the right time to step away from the business? What would he like to do with that time? How does Jason feel about the challenge of tying his identity to his company? What are the dangers of doing so? 4.) How does Jason approach decision-making frameworks? What does Jason believe is the right way to respond when a decision does not go as planned? Where do many make mistakes here? Does Jason feel regret with decisions? How does Jason try and minimise regret? 5.) How does Jason feel about his biggest insecurities as a leader and CEO today? What are Jason's views on a CEO's ability to have self-doubt and be vulnerable? How have his views on this changed over the years? In what way has having kids impacted Jason's operating mindset? How has it changed what he values and appreciates? Item’s Mentioned In Today’s Episode Jason’s Favourite Book: In Praise of Shadows As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Simón Borrero is the Founder & CEO @ Rappi, the startup that has become a cornerstone of the Latin American mobile ecosystem, coined as "the next Everything Store of Latin America". To date, Simon has raised over $1.7Bn for the company from the likes of Sequoia Capital, a16z, Softbank, DST Global, Y Combinator and more. Prior to Rappi, Simon was the founder of multiple former companies including Imaginamos, a software studio he grew to over 300 people. In Today’s Episode You Will Learn: 1.) How Simon made his way into the world of startups and came to found "the next Everything Store of Latin America" in Rappi? 2.) How does Simon think about the importance of zone density for a business like Rappi? What are the number of deliveries required for Rappi to make for the business to be breakeven? What is the key metric that determines the success of the business for Rappi today? 3.) How does Simon approach the balance of capital efficiency vs growth? How does one know when to pour fuel on the fire and go for growth? When is the right time to really focus on unit economics? Why does Simon believe expanding Rappi can be analogised to scaling a coffee shop? 4.) Rappi has now raised $1.7Bn from some of the best investors in the world, what does Simon believe Rappi did to enable them to be so successful fundraising? Was it a difficult shift for Simon to make moving from lean to capital abundance with the successful fundraises? What changed? How did Simon change as a leader? What is the story of Sequoia coming in? 5.) Customer acquisition: What were some of the biggest challenges when it came to initial customer acquisition for Rappi? What does Simon mean when he says "donuts for downloads"? What is the story there? 6.) Driver acquisition: In the UK and the US, driver acquisition is a big challenge, what did Rappi to do enable them to scale their driver supply so efficiently? What works? What does not work? 7.) Restaurant acquisition: What were the hardest elements of onboarding the first restaurants? How did Uber Eats entering the market actually make Rappi so much more efficient as a business and service? Item’s Mentioned In Today’s Episode Simon’s Favourite Book: The Prosperity Paradox As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Tony Fadell, often referred to as “the father of the iPod,” is currently Principal @ Future Shape, a global investment and advisory firm coaching engineers and scientists working on foundational deep technology. Prior to Future Shape, Tony was the Founder & CEO @ Nest Labs, the company was ultimately acquired by Google for a reported $3.2Bn. Before Nest, Tony spent an incredible 9 years at Apple Inc, where, as SVP of Apple’s iPod division, he led the team that created the first 18 generations of the iPod and the first three generations of the iPhone. Fun facts, Tony has filed more than 300 patents for his work and is also a prolific angel investor having invested in the likes of mmhmm and Nothing to name a few. In Today’s Episode With Tony Fadell You Will Learn: I. The building blocks of an entrepreneur What was the moment that Tony realised that he wanted to be an entrepreneur? “I got my first money when I was in third grade, because I had an egg route. We'd go get eggs from the farmer, and I'd load them in my wagon. Then my younger brother and I would go door to door around the neighborhood, and we'd sell eggs. And that was an every week or every other week situation. And I got money in my hands. And I was like, Oh my God, I can do whatever I want with that money – I don't have to ask anybody, I can just do it. And so that was the level of freedom that, especially when you're young, feels really cool. And then as I got older, I started to buy Atari video game cartridges for my 2600 (yes, I'm that old!), and that was really, really fun too.” What was the biggest lesson that Tony learned from his father on sales and building trusted relationships? "And he said, very clearly, Look, this is a relationship. If I make this person successful, he's gonna want to come back to me over, and over, and over. But if I sell him something and it doesn't sell, and he has to discount and he loses money, he's not going to come back. Even if I don't have the right product, I'll tell him where to go to get the right product they're looking for, or if they're picking the wrong one, I'll tell them, here's the right one, because my job is to make them successful. Because if they're successful, they'll come back to me year after year after year. And even when we have a down year, they're going to trust me, and they're going to come back." II. Reflections on experience How does Tony Fadell think about and assess his own relationship to money? How has it changed over the years? "So my relationship to money now is that it's just a means to make change happen. And so literally, for me, I can just have a backpack, my computer, my phone, a couple of roller bags with my clothes. And that's enough to live life with my family. I don't need all this other stuff. COVID taught me that even further." How does Tony determine true friendships vs transactional relationships? “If it's not a reference – if it's not coming from somebody saying, Hey, you really need to meet this person – I take everything with a grain of salt. With anybody who comes to me cold, I think they probably want something. I try to find that out through the network, Do you know this person? What are they about?" III. Tony Fadell on becoming a mentor Why does Tony Fadell believe that founders have to be "coachable"? “I think anybody who's trying to do something that the world has never seen before, or trying to work with people who are, they'd better be coachable. Because you're going to be so narrowly focused, you're going to be so heads down, you're going to be so on a mission, that sometimes you'll be blinded, and you'll need somebody to come from left field and go, Wait a second, dude, you're not thinking about this right." What are the core signs that an individual is coachable? Trustworthiness 2. Willingness to listen What does Tony believe is the right way to deliver advice without fluff? "First, it's about trust. You have to be able to have a trusted relationship with somebody. And second, there are different ways of delivering a message. You can deliver a message the first time in an iron-fist-in-a-velvet-glove kind of way. But sometimes the velvet glove is going to come off." How do people make mistakes when giving advice? “I'm in too many board meetings; we have over 200 investments. I've seen all kinds of different CEOs and different boards, where the investors don't want to feel like they're going to get a bad rep because the CEO is going to say something if they say something negative." What does Tony Fadell advise founders when it comes to finding mentors? “Usually, a really great mentor is going to be highly selective. They're going to be like, I don't want to work with you. They only have so much time for people who are actually coachable." What are the characteristics of the best mentors? "You're gonna have tough love with them, you're gonna say things that they don't want to hear, you're not going to be liked all the time. Hopefully, one day, you'll be respected if not liked. And that's what it means to be a mentor.”  IV. Changing perceptions How does Tony assess his own relationship to self-doubt? “Everyone goes through imposter syndrome. Everyone does. We all have gone through it, I go through it. Because you know what, when you're doing stuff you've never done before, and you're changing the world, no one else has done it either. No one else has done it either. That means it's okay. And I always say, if you don't have butterflies in your stomach each day, you're either not paying attention, or you're not pushing hard enough and taking enough risk." What are Tony's views on failure? “Now, there's taking stupid risks versus risk mitigation and taking calculated risks. But you should always be living on the edge of pushing yourself because that's where the growth is, that's where the change is happening." Does one learn more from success than from failure? "How we do and change the world is through the same method. We go do, and then we fail, and then we learn from that, and then we do again.” What does Tony mean when he says, "do, fail, learn." “Look, it's do, fail, learn; do, fail, learn. There's no such thing as learn and then you're able to do. No, no, no. When you really learn in life is after you've tried to do it." What is the right way for entrepreneurs to present their boldest of ambitions? "Look at Elon now. If he was pitching what he's doing now 15 years ago, people would go, No way! A few people, like Jurvetson and others, said, Yeah, sure, okay, great. But very few people would get behind that huge boldness." “So what they do is – and this is what I've had to do – they start and just pitch that simple ‘What's the next three to four years look like?’ and never tell anybody about the big picture. Because you scare most people off." How do investors need to change how they think about ambition and upside? 5.) Why does Tony believe the first trillionaire will originate from the climate change space? Why is the majority of plastics recycling total BS today? Why does Tony believe we need to fundamentally transform our economies? How do funding markets need to change to fund this structural reshaping of society?

Scott Sandell is the Managing General Partner of NEA, one of the leading firms of the last 3 decades with now close to $24Bn under management and a portfolio including the likes of Salesforce, Robinhood, Plaid, Databricks and many more incredible companies. As for Scott, since joining the firm in 1996 he has led investments in many industry-transforming technology companies including Salesforce.com, Tableau Software, WebEx and Workday. Scott also serves on the board of rocketships including Robinhood, Cloudflare, Coursera and Divvy to name a few. As a result of this investing success, Scott is among the most frequently named venture capitalists to the Forbes Midas List. In Today’s Episode You Will Learn: 1.) How Scott made his way into the world of venture close to 3 decades ago back in 1996? How he came to be Managing General Partner of NEA today? What is entailed in the role of "Managing General Partner"? 2.) What has been the single biggest change in the venture landscape that Scott has observed since his entering in 1996? How did the boom and bust of the dot com and 2008 impact his investing mindset? Consequently, how does Scott advise founders to think about capital efficiency and business model flexibility? What concerns Scott today? 3.) Why does Scott believe "this is an incredible moment in history for the asset class of venture"? How does Scott think about the core physics of company building changing? How is it companies are able to scale and grow so much faster today? Does their speed of growth change their capital requirements? 4.) Does Scott agree with Bill Gurley, "the biggest challenge is the oversupply of capital today"? How does Scott analyse his own relationship to price and price sensitivity? What is Scott's framework for determining when to pay up vs when to remain disciplined? How does Scott feel about the rise of SPACs? How will this shake out over the coming years? 5.) How much have NEA companies raised over the last decade? Of that, how much did NEA invest? Is the answer to continuously scale AUM? How does NEA approach investment decision-making with the size of partnership it has? What does Scott mean when he says, "we vote on the process"? How do you create a partnership of trust at scale? Item’s Mentioned In Today’s Episode Scott's Favourite Book: The Old Man and the Sea Scott’s Most Recent Investment: Loanpal As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Daniel Ek is the founder, Chief Executive Officer, and Chairman of the board of directors of Spotify, the world’s most popular audio streaming subscription service with 345m users, including 155m subscribers, across 170 markets. In Today’s Episode With Daniel Ek You Will Learn: 1.) How Daniel made his way into the world of startups and came to found the most popular audio streaming subscription service in the world in the form of Spotify? 2.) How does Daniel approach effective decision-making today? What is his core process? How does Daniel determine between reversible and irreversible decisions? What does Daniel's learning process look like for new topics and material? How does this differ from topic to topic? What does Daniel mean when he says "I look to become the Chief of X Officer" for a time? 3.) How does Daniel think about the transition from Founder to CEO? Why is the topic not discussed enough? Where does Daniel see many founders struggle to make the transition? Which elements did Daniel find the most challenging? How has he scaled into them over time? Is it possible to change who you are as a person with this transition? 4.) How does Daniel think about what it takes to create an environment of safety where everybody can feel free to express their ideas, thoughts and concerns? What sort of failure does Daniel accept? What sort of failure does Daniel not accept? How does good news flow through an organisation differently to bad news? How does Daniel determine when to quit a project vs when to persist and stick to it? 5.) Prima Materia: Why is Prima not just another fund? How is Prima fundamentally different? What does Daniel believe Shak is world-class at? A walkthrough of Shak and Daniel's decision-making process for choosing to partner with each other on Prima? What has been their first investment? Why gave them the conviction to write this check as their first? Item’s Mentioned In Today’s Episode with Daniel Ek Daniel’s Favourite Book: Shantaram As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here.

Vlad Tenev is the Founder & CEO @ Robinhood, the company that provides commission-free investing, plus the tools you need to put your money in motion. To date, Vlad has raised over $5.6BN with Robinhood including a $2.4Bn raise this month and some of their investors include the very best in the business; Ribbit, Sequoia, Greenoaks, Index, IVP, Thrive, GV and more incredible names. Before Robinhood, Vlad started two finance companies in New York City. In Today’s Episode You Will Learn: 1.) How Vlad made his way into the world of startups and how the "Occupy Wall St" movement spurned much of the inspiration for the founding moment of Robinhood? 2.) Looking back over the last month, does Vlad believe Robinhood is a victim or an enabler of the crisis? What does Vlad believe upset customers the most? With the benefit of hindsight, what would Vlad have done differently? What does Vlad believe are some of the biggest misconceptions about how the last few weeks played out? 3.) Funding: Why did Robinhood need the scale of funding that it took, so fast? What are the capital requirements for a business like Robinhood? Who regulates their compliance? Was Robinhood forced to put the interests of the business ahead of the interests of their customers? Why does VAR need to be changed as a risk estimation mechanism? 4.) What has Vlad learned as CEO about managing through a crisis? What did Vlad do to ensure morale remained high internally, despite the external events? What works? What does not work? What did Vlad learn about himself through the experience of the congressional committee and testifying before them? As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Sebastian Siemiatkowski is the Founder and CEO @ Klarna, the company that makes online shopping simple, allowing you to buy what you need today and pay later. To date, Sebastian has raised over $2.1Bn for the company from the likes of Sequoia, Silver Lake, Blackrock, DST, Northzone, Creandum and even Snoop Dog to name a few. Klarna has been an incredible 16-year journey for Sebastian with it now being the most valuable private technology company in Europe with over 3,500 employees. In Today’s Episode You Will Learn: I. The Importance Of Learning To Learn Fast What is the best way to learn fast?  “People talk about it like there's this learning curve, and the best spot is at the place where you're challenged to the precise point where you're almost giving up, but not entirely. That's exactly it.  “And I have this amazing swim teacher for my children, her name is Petra, and she's just fantastic. I just love watching her because she has this ability of taking my children in the pool and pushing them to that exact point where they are almost, almost giving up, and they're learning at such a pace. And if I can recreate such an environment in Klarna, if I can create an environment, if I can be part of creating an environment where we put people in that position where they just are exactly at that curve where they are challenged, supported, and kind of at the edge and being given the ability to learn really fast and really discover what it means to have an impact.”  Does Sebastian compare his work to other companies’? “I don't think that much about what other people or other companies or other things out there could have done different. And there's pros and cons to that. But the benefits of that is that it speeds up my learning. Because a lot of people – and I've realized that as I manage other people – is that because they're so obsessed with trying to think about what other people could have done differently, and why situations arose, and why it wasn't their responsibility and so forth, they spend a lot of time on that, because we've unfortunately been brought up in some kind of guilt that it's bad to do wrong, and it's bad if it's our fault, and you want to avoid that.  “And these psychological constraints, unfortunately, hinder people from developing much faster, because if you go into every situation and say, the only thing that's relevant here is what I could have done differently, what I could have learned from this – if that's the only thing, it's just like, whatever, I accept my responsibilities. What could I have done differently? If you only focus on that, you just learn much faster.”  How does Sebastian transform his self-doubt into a positive? “I think self-doubt is not nothing. It's not a bad thing, right? It's a very healthy thing, if it represents you continuously trying to understand, am I doing the right thing? Is this something that I want to do? Am I making the right decisions? So I think it's extremely healthy to do that. I'm not saying it's not painful or tough when you have it. But I think it's a very positive thing.  “I'm much more worried when people tell me they have no self-doubt. And then I'm like, uh-oh, because that means that you're not really reflecting on your actions, and you're not learning from them. So I wish I could give you something more comforting than that, but I would actually say enjoy it. Be happy that you have it, and it's gonna make you a better person.”  II. Sebastian’s Management Philosophy What does Sebastian believe companies can learn from soccer?  “I love the fact that Michael Moritz wrote this book that I still haven't read, so it's kind of funny that I'm referring to it, but he wrote this book about Ferguson, that manager of Manchester United. And I think it's very relevant, because today, the saying is that for people to be motivated at work, they need to have a higher purpose, the company needs to do something good, and so forth. And I am not disputing that, that is very true that it contributes to people's sense of purpose, and so forth. But before you even get to that level, we have to ask ourselves, what is it really that makes people motivated and enjoy themselves? And I think when I think about that, I often look at sports, because why do people love soccer? What's the higher purpose of winning Champions League? People say, oh, there's a massive higher purpose, but not entirely, you're not really making the planet better by winning. Still, people are massively engaged in these things. Why?  “Because it's a team effort, there are clear roles, you know exactly what you're supposed to do – I'm supposed to put the ball in that score. And then it's very clear how you win, there is a referee that stops people from cheating. And so there's a lot of things in that environment that makes it motivating, that makes people engaged, and those things are usually lacking in companies.” How do you know when someone is at that crucial point of the learning curve? “The problem with a company is that it's a much more complex environment with a lot of other things going on in parallel in people's lives. And so I have definitely occasionally missed to see that people are beyond that point.” “In Sweden, there's this course called Situation Adopted Management, which basically means that there is no single management technique. You look into the situation, you try to understand it from multiple angles. And then depending on where that individual is, and how you perceive the mental status, and the mood of that individual, and so forth, you try to adapt. Either you coach or you challenge or you instruct or you do different things. There's not a single methodology that will allow you to deal with those situations. But a lot of it is empathy. It's the ability to look at people and read them, and try to understand, and ask them questions, and understand where they are.” III. How Sebastian Manages Complexity At Scale What are Sebastian’s biggest lessons learned from Klarna growing to 3000+ people spread across multiple offices across the world? It’s the manager’s job to deal with the complexity in a company  It’s not for everyone  What role does Sebastian believe a manager should play in a company as it scales? “I think a lot of times as a company grows, what ends up happening is the thing just becomes so complex. So management tries to organize the company in a way that makes sense to them and that is easy to understand for them. But the consequence of that often, unfortunately, is it makes no sense for the person who's actually doing the job. So they lose the purpose. Why am I coming to work? What are we trying to achieve? All of these things get lost.  “So what we said is, we have to do the exact opposite. The critical element is that the people who are actually supposed to do something – not the manager – the people actually supposed to do something, if they program or to do a marketing campaign, or whatever they're doing, they need to come to work every day and feel I know exactly why I'm coming, I know how I'm contributing, I know who I'm contributing for, I know what value I'm creating.  “And if that thing creates tons of complexity for us, as managers, because the whole system becomes much more complex, then that's what we're getting paid for. That's the one. That's why we're getting a good salary. Because we need to manage that complexity.” What does Sebastian look for in talent?  “Keep very close on the recruitment … Especially in a country like Sweden, a country where a typical saying is, alla ska komma med, which means, everyone should come, everyone should join. And it's very nice. And I appreciate that with Swedish culture, I'm not trying to really call it. I think it's fantastic and it's a fantastic society. But as a consequence, it took us some time to conclude something which maybe in the US or maybe even in the UK as it would have been much more obvious, which is that it's not a company for everyone. It is a company for the people that want to have that challenge, that want to be in that environment, that think that's interesting, that want to learn a lot fast, and want to get a lot of things done. And that's not everyone, and that's okay.  “Like when you play soccer – some people play soccer for fun, other people play to win the Champions League. People do it for different reasons. And they have different ambitions with it and different objectives with it. And the same applies to us.  “So it took us some time to realize that we need to tell people, look, just so you know, this is not going to be your standard company, you're going to be expected to do a hell of a lot of things, you're going to be expected to be challenged, you're going to expect it to do your utmost. And we're going to try to support you and help you and grow. So just know what you're getting into, before you get into it.” IV. Retail Banking 10 Years From Now What does Sebastian see as the future of everyday banking services? “One thing I would say, it's going to be a much smaller industry. And that's because it is ridiculous that moving money back and forth is a trillion-dollar industry. That is ridiculous. There is no good reason for that whatsoever. This is going to be a much more cost-efficient, much smaller revenue business than it is today. But even though it would be much smaller than it is today, it's still massive, and Klarna has the opportunity to be one big player in that industry, similar to what Tesla is doing in cars or whatever, that's what I want to do. And I feel we have all the prerequisites to accomplish that.”  “There's going to be this push that's going to transform this industry and the people are going to lose on it are the suits in the marble offices in the city centers. That's where the pain is going to be felt, but the winner is going to be the consumer.” What do the next five years look like for Klarna? “It's a little bit like self-driving cars – we all know it's going to happen, the question is when. And based on what I've seen in the last 15 years, and I've seen how retail has gone from retail to ecommerce and all these trends, this decade is going to be the disruption of retail banking.  “At the end of this decade, there will be a couple of new total players that will be very dominating in this space, and the rest will either cease to exist, will merge and try to acquire some of the new ones, or maybe a few of them will manage to reinvent themselves. But this is going to be an extremely interesting time.” Sebastian’s Favourite Book: The Neverending Story As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Patrick Spence is the CEO @ Sonos, the sound experience company connecting millions of listeners around the world to the content they want. Prior to their IPO, they raised over $450M from the likes of Mike Volpi @ Index, Satish @ Redpoint and e.ventures to name a few. As for Patrick, prior to Sonos, he spent an incredible 14 years with RIM (makers of Blackberry) across multiple different roles. In Today’s Episode You Will Learn: 1.) How Patrick made his way into the world of tech and startups and became an instrumental part of the exec team at Blackberry? How that led to his joining Sonos as COO and later becoming CEO? 2.) How did building and growing RIM influence everything that Patrick does at Sonos? From the battle with Apple, what were Patrick's biggest lessons on the right way to approach competition? How does Patrick think about both partnering with Google today whilst also suing them at the same time? 3.) From COO to CEO: How did Patrick make the transition from COO to CEO so successfully? What were the most challenging elements to scale into? How does Patrick empower his team to have the confidence to stand up and say no to the CEO? How can one encourage debate and dissent in the team? 4.) How does Patrick feel about the role that vulnerability has to play in leadership? How does Patrick approach his own self-doubt as a leader today? How does he manage it? How does he advise founders unsure if they can scale into their leadership roles? What mentors does Patrick have? What has he learned from them? Item’s Mentioned In Today’s Episode Patrick’s Favourite Book: The Infinite Game: How Great Businesses Achieve Long-Lasting As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jeremy Liew is a Partner @ Lightspeed Venture Partners, one of the leading firms of the last decade with a portfolio including the likes of Affirm, Snapchat (Snap), Mulesoft, Epic Games, Carta and more amazing companies. As for Jeremy, in the past he has led deals and sat on the boards of Snap, Affirm, Blockchain.com and The Honest Company to name a few. Before Lightspeed, Jeremy was with AOL, first as SVP of corporate development and chief of staff to the CEO, and then as general manager of Netscape. Due to his incredible investing success, Jeremy has been featured on the Forbes Midas List multiple times. In Today’s Episode We Dissect The Snapchat Memo: I. How Jeremey first learned of Snapchat How Jeremy Liew first heard about Evan Spiegel and Snapchat? "It's actually kind of a roundabout story. We first heard about Snapchat, because one of my partners Barry Eggers is a very involved dad. And he noticed that his daughter had started taking weird selfies" What was the process to first get in touch with Evan? "The challenge was, the website only had info at Snapchat email address was the only info The only contact info available. So I emailed them, and I never heard back. Why was it such a challenge? "I then looked up Snapchat on LinkedIn, and I couldn't find any contact information. And I was in a little bit of a loss, I wasn't getting any responses from the email, there was nothing listed on LinkedIn. So I ended up doing a who is look-up to try to find out who had registered the Snapchat URL, and I got an info@ snapgrouplimited email. So I emailed that. And then as again, I didn't get any response. What was the breakthrough in the end? "....Finally, what I decided to do was since Evan was a student at Stanford, and since I graduated from Stanford for business school, at that time, Facebook allowed you to message people who were in the same network, and Stanford constituted that. So I messaged him through Facebook, and I finally got a response. But this time, I got a response within five minutes." II. The Analysis Of Snapchat's Early Market What are the 4 things Jeremy looks for when making an investment in consumer? Can this become part of pop culture? Does this create new habits? Is there a scalable way to grow? Does the founder have a unique insight that explains the success? Why does Jeremy believe that usage with young females is the biggest predictor of future consumer social success? "Generalising, Women build their relationships through, you know, conversations, and they build those relationships through sharing information with each other. And obviously, that sort of conversation or relationship is a fantastic conduit for word of mouth for anything that people really appreciate." In what ways does Jeremy like to see consumer social companies become part of pop culture? "Today, if you think about whether it be social networking, apps, messaging, e commerce, streaming media, it's all part of pop culture. And so as much as movies or television or music or dance, and so if you ask yourself who are the early adopters of pop culture" What are examples of this? "Social networking, apps, messaging, e commerce, streaming media, it's all part of pop culture." Did the market evolve the way that Jeremy thought it would? "And one of the things that surprised us a little bit was that this was very strong in Southern California, Northern California, and Georgia, when we first invested and parts of the South" What was a surprise to Jeremy Liew in terms of market evolution? "In Norway, which had actually transcended, that sort of high school and college-age population, in fact, become the number three most downloaded app, most popular app, in Norway at that time. So ahead of Instagram, ahead of Facebook, and so forth. And so that's what I think gave us that early indication that the app was going to be able to break out beyond its high school, college student, initial starting point, not just in the US, but everywhere" III. Reflections on Snapchat's Early Traction What did the Snap user to install count look like at the time? "In, you know, March, April of 2012, they had about 90,000, daily active users off of the base of 180,000 installs." How does this compare with many others in the consumer social space? "That's a very, very high ratio." What were Snap's retention numbers at the time? "50% retention after 90 days, which again, suggests high engagement, high retention, high growth that speaks to upside volatility" How did Snap's frequency of usage on an individual basis look like at the time? "So people were opening the app six times per day, they were opening at least once every second day." Across, retention, usage and user to install, what are the benchmarks for great, good and average? " I would say as a rule of thumb, in messaging and social networks, you would want to see at least a DAU to MAU ratio of north of 50%. And you would want to see at least a D 30 of say 30 to 40%, for your for something to really be working to be sort of at that outlier level." IV. The Truth About The Snapchat Founding Team What unique insight does Jeremy believe that Evan always held for the company and the product? "One of the things that was so special about Evan, and that I think, has continued to contribute to the success of the company has been that he's always been able to do that to look at something with fresh eyes, and not iterate over what the current state of the art is that, you know, just from first principles basis" How has Jeremy seen Evan change and evolve as a leader? "I think his maturity as a business leader, as a leader of people, as a manager, you know, as a strategist, although he always had very good strategic instincts, but they've just continued to grow and evolve and blossom." What were some of the big inflection points in his development? "So you know, the feed has always been up until this point, in reverse chronological order, I think largely because that's what friendster do choose to do. And then Evan comes along. He says, How do you tell stories beginning, middle, end. Now go to social media? How do they tell stories in reverse chronological order means and middle beginning? Well, that doesn't make any sense. And so he said, we're going to create a whole new feed of stories, and they're going to be told in chronological order beginning middle end." Who are some unsung heroes from the Snap journey that were transformational? "Bobby doesn't get enough credit. From the very beginning from I think maybe a couple of months in was thinking about the breakthroughs that had been happening computer vision and the implications for what that could build....Imran Khan, he really helps take a lot of the load off of Evan allowed me to focus on product engineering, he took over sales and monetization Ops, he did a lot of the financing work in the time when Snapchat raised a lot of capital."

Todd McKinnon is the Co-Founder & CEO @ Okta, the identity layer for the internet, providing one trusted platform to secure every identity, from customers to your workforce. Prior to their IPO in 2017, Todd raised over $229M for the company from some of the best in the business including Sequoia, a16z, Greylock, Khosla and Floodgate to name a few. Prior to founding Okta, Todd was VP of Development @ Salesforce.com where he spent an incredible 5 years and before that enjoyed an 8 year run in the software development team @ PeopleSoft. In Today’s Episode You Will Learn: 1.) How Todd made his way into the world of startups with PeopleSoft and Salesforce? What was the a-ha moment for Todd with the founding of Okta? What were the biggest management takeaways from his time with PeopleSoft and Okta? How did Todd convince his wife that leaving a safe job with Salesforce to found a company was the right decision? 2.) How does Todd approach decision-making today? What frameworks does he use to optimise his decisions? How does Todd analyse reversible vs irreversible decisions? How does Todd know when he has done enough work and is ready to make the decision? Who does he debate the most important decisions with? 3.) What does Todd believe makes for a truly great enterprise software entrepreneur today? What were the first elements to break in the scaling of Okta? When is the right time to hire your first recruiters and Head of People? What should you look for in those people? How did Todd make mistakes when it comes to hiring recruiters? 4.) What are Todd's biggest lessons on successful board management? How would Todd describe his style of board management? How has it changed over the years? What can CEOs do to extract the most value from their board? What were the biggest mistakes Todd made in the early interactions with his board? 5.) How does Todd balance the growth expectations of Wall St on a quarter by quarter basis with the long term vision and strategy? Why does Todd believe that Okta has been able to make the transition from unsexy to one of Wall St's most loved companies? What is the secret to investor relations as a public company? Item’s Mentioned In Today’s Episode Todd’s Favourite Book: Slaughterhouse 5 As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Assaf Wand is the Founder & CEO @ Hippo Insurance, with over $700M in funding Hippo are setting a new standard for home insurance and offer protection for what’s important to today’s homeowner. Nima Ghamsari is the Founder & CEO @ Blend, with over $665M in funding they are the digital platform streamlining the journey from application to close — for every banking product. Max Simkoff is the Founder & CEO at States Title, with $229M in funding States Title are using machine intelligence to create a vastly more simple and efficient closing experience for lenders, real estate professionals, and homebuyers. Brendan Wallace is a Co-Founder and Managing Partner at Fifth Wall, with over $1.3Bn in commitments and AUM across multiple different vehicles, they are the largest venture firm focused on the real estate industry and property technology for the Built World. In Today’s Episode You Will Learn: 1.) 3 of the largest and most successful founders in the financial real estate market, what have been their biggest learnings from their friendship over the last 5 years? What have been some of the most hotly debated topics they have had as a group? How did their opinions and views change as a result? 2.) How do they think and feel about the tech exodus from Silicon Valley, temporary movement due to COVID or fundamental shift? How closely correlated is the move out of California with the explosion of liquidity from IPOs and acquisitions? What pisses Max off most about people leaving CA currently? 3.) How have their roles as leaders changed in the time of COVID? What have been the most challenging elements? What have they had to embrace? What have they had to disregard or stop? What advice do they give to other founders scaling into hyper-growth in a remote format? 4.) What do they believe is the fundraising strategy that allowed them to raise over $1.5Bn as a group? How do they think about what they look for in each stage of investors? How does it change when entering growth stages? How has their experience been having corporates play a large role in their financing? What are the biggest challenges of working with corporates? What does one need to do to extract the most value from them? Item’s Mentioned In Today’s Episode Max’s Favourite Book: A Heartbreaking Work of Staggering Genius As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Christian Reber is the Founder & CEO of Pitch, the collaborative presentation software for modern teams. To date, Christian has raised over $52M for Pitch from some of the best in the business including Index, Thrive, Blueyard and then some amazing individuals including Instagram's Kevin Systrom and Mike Krieger, Zoom's Eric Yuan, Datadog's Olivier Pomerol and Tiny's Andrew Wilkinson. Prior to Pitch, Christian was the Founder @ Wunderlist, raising $35M from the likes of Sequoia and Atomico before being acquired by Microsoft. In Today’s Episode You Will Learn: 1.) How Christian Reber made his way into the world of startups? How that led to his founding te global phenomenon, Wunderlist? How his experience with Wunderlist led him to start Pitch most recently? 2.) Does Christian regret selling Wunderlist to Microsoft? What was the reasoning and logic behind it? What does Christian believe Microsoft did wrong that resulted in Wunderlist no longer being in existence today? How did Christian deal with the personal depression post the sale of Wunderlist? 3.) How does Christian assess and evaluate his personal relationship to risk? What does he do when making risky and large decisions to ensure he is comfortable? How does Christian feel about his relationship to money? How has it changed over time? How does Christian approach personal finance today between startup investing, fund investing, cash and savings? 4.) How does Christian think about what great product design means today? How does he balance gut and instinct with granular data when making product decisions today? How has this changed over time? How has Christian structured his team to make the fastest and most efficient product decisions? 5.) How would Christian reflect on his own style of board management? How has it changed over time? What element does he still to this day find most challenging? What board moment would he say is his most memorable? Who has been his favourite board member to work alongside? Item’s Mentioned In Today’s Episode Christian’s Favourite Book: The Unbanking Of America: How the New Middle Class Survives As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Matan Bar is the Co-Founder & CEO @ Melio, the company that provides the simplest way to pay vendors and contractors. To date, Matan has raised over $254M for Melio from the likes of Accel, Bessemer, Aleph, Coatue and General Catalyst to name a few. Prior to founding Melio, Matan Bar was Head of PayPal Consumer Product Center and before that was a Head of Product and GM @ eBay in their Israel Innovation Center. In Today’s Episode You Will Learn: 1.) How Matan Bar made his way into the world of startups and came to found one of the fastest-growing companies today in the form of Melio? 2.) What is the single most important thing in a financial transaction business? How does Matan think about the balance between optimising for transaction volume vs revenue? What does Matan believe are the core network effects within payments businesses? Why do most opt for closed network effects? How is Melio different? 3.) What have been some of the biggest challenges of adding 170 people in one year? What breaks first? What needs to be in place to ensure the culture can scale with the headcount? How does Matan structure the leadership team to manage this hyper-growth? Has Matan struggled with self-doubt in his leadership during this hyper-growth? 4.) What specifically has Melio and Matan done to achieve a 49% female to male ratio within the company? What works when it comes to implementing diversity at scale? Where do so many people make mistakes? What specific strateies have allowed Melio to hire some of the best female engineers? 5.) How does Matan most like to interact with his board? How does he determine the advice to ingest vs the advice to reject? What have been some of his biggest lessons when it comes to successful board management? Where do many first time founders make mistakes when it comes to investor value add and extraction? Item’s Mentioned In Today’s Episode Matan’s Favourite Book: The Unbanking Of America: How the New Middle Class Survives As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Michael Eisenberg is a Co-Founder and Equal Partner @ Aleph, with over $550M under management and a portfolio including the likes of Lemonade, Melio and HoneyBook, they are one of the leading early-stage firms of the last decade. Prior to founding Aleph, Michael spent 15 years as a General Partner @ Benchmark and before that, made his way into venture with Israel Seed Partners where he built an incredible portfolio over an 8 year period. If all of this was not enough, Michael is also an author having published 4 books. In Today’s Episode You Will Learn: 1.) How Michael made his way into venture over 25 years ago and how his 15 years at Benchmark led to his founding Aleph? 2.) How has seeing multiple booms and busts impacted Michael's investing mindset? What do many misunderstand when it comes to reserve allocations in market cycles? Why does Michael believe busts are more psychologically impactful than financially impactful? 3.) How does Michael approach portfolio construction with Aleph today? How does Michael think about the right level of portfolio diversification? How does Michael think about the right level of capital concentrated into one company? How does Michael assess the difference between risk and uncertainty? What do many misunderstand between the two? 4.) Why does Michael believe in generalist VCs over specialist VCs? Why do they win? Why does Michael believe in small boutique firms vs large multi-stage firms? How does Michael think about the notion of ownership on first check? Is it possible to really build ownership across rounds today? 5.) How does Michael reflect on his own style of board membership today? How has it changed? What have been some of Michael's biggest lessons on board membership from Bruce Dunlevie @ Benchmark? What advice does Michael have to newer investors joining boards for the first time? Item’s Mentioned In Today’s Episode Michael’s Most Recent Investment: Melio As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Justin Fishner-Wolfson is founder and the managing partner of 137 Ventures, a growth-stage venture firm that provides customized liquidity solutions to founders, investors, and early employees of high-growth private technology companies. Their portfolio includes the likes of SpaceX, Wish, Anduril, Flexport, and Rigup to name a few. Previously, Justin worked on the investment team at Founders Fund and before that served in the US Department of State under Alan Larson, Undersecretary for Economic, Business and Agricultural Affairs. In Today’s Episode You Will Learn: 1.) How Justin made his way into the world of venture with Founders Fund and how that led to his founding 137 Ventures? What specific lessons did he learn from Peter Thiel that he has applied to his investing mindset? 2.) What does Justin mean when he says, "it is the last double that matters"? Why does Justin believe that liquidity aligns incentives between VCs and founders? When is the right timing for this liquidity and are there limits to the sizes of secondaries founders and teams should take? 3.) How does Justin think about his own price sensitivity today? Why does Justin believe that the conventional VC views on ownership are outdated and no longer as relevant to this class of company? How does Justin think about diversification among the portfolio today? What is the right level? What is too diversified? What is too concentrated? 4.) Why does Justin believe that standard thoughts around CAC/LTV are wrong? How have they changed over time? How should founders think about this and present these metrics to investors? Given these metrics, how does Justin feel about the revenue multiples we are seeing today both in private and public markets? Item’s Mentioned In Today’s Episode Justin’s Favourite Book: The Hitchhiker's Guide to the Galaxy Justin’s Most Recent Investment: Lattice As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ilkka Paananen is the Co-Founder & CEO @ Supercell, the makers of some of the most wildly successful games of the last decade including Hay Day, Clash of Clans, Boom Beach and more. Prior to Tencent acquiring a majority stake in the company at a reported $10.2Bn acquisition, Ilkka raised over $143M for the company from Accel, Index, Atomico, IVP, LVP, Initial and Lifeline. Throughout his incredible leadership of Supercell he has coined the term, "the least powerful CEO", a fascinating concept and one we dig into in this episode. In Today’s Episode You Will Learn: 1.) How Ilkka made his way into the world of startups and came to found one of Europe's most valuable companies in the form of Supercell? 2.) How does Ilkka think about his own relationship to risk? Why does Ilkka believe the No 1 reason companies die is due to their relationship to risk? How does Ilkka evaluate his relationship to money? How has it changed? How does Ilkka feel the weight of responsibility with his wealth? 3.) What does being "the least powerful CEO" mean in practice? What does Ilkka belive is key for leaders to really empower their team to be bold and ambitious? How can leaders create environments of safety where it is ok to fail? Where do many leaders go wrong here? 4.) The first 3 Supercell games were failures, how did Ilkka deal with those really hard times? How can leaders sustain morale in such hard times? Supercell then had 3 big hits in a row, how does one prevent ego and over-confidence in teams? What is the beer vs champagne culture? 5.) How does Ilkka think about the importance of focus? What has Ilkka done and learned to be a much more focused leader? How does Ilkka approach the aspect of competition today? Item’s Mentioned In Today’s Episode Ilkka’s Favourite Book: What You Do Is Who You Are: How to Create Your Business Culture by Ben Horowitz As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Hubert Palan is the Founder & CEO @ ProductBoard, helping product managers understand what customers need, prioritize what to build next, and rally everyone around the roadmap. To date, Hubert has raised over $64m for ProductBoard from the likes of Sequoia, Index, Kleiner Perkins, Bessemer and Credo Ventures to name a few. Prior to founding the company, Hubert was VP Product Management @ GoodData where he played an instrumental role in their scaling from 6 to 300 people. In Today’s Episode You Will Learn: 1.) How Hubert made his way from Eastern Europe to SF, made his way into the world of product management and came to found ProductBoard? 2.) Why does Hubert believe that "founder insight" is overrated? What strategies and tactics does Hubert give to founders to be more mentally plastic and flexible? How does one know when to persist when things are not working vs when to give up? What is the decision-making framework? 3.) Why does Hubert believe that "big and bold product vision can be dangerous"? How does Hubert think about when is the right time to release a second product? What are the core elements to tackle when thinking about a second product? Where do many make mistakes here? 4.) Why does Hubert believe that, "if you get to product market fit by accident, you could be in trouble?" What does Hubert advise in terms of studying if and how you got to product market fit? How can one use post-mortem analyses here effectively? 5.) Why does Hubert believe that transparency is so necessary today with the team? Should founders be transparent when it comes to M&A, fundraising etc? Where are the limits? What makes it so hard to instil effectively? What do many founders misunderstand? Item’s Mentioned In Today’s Episode Hubert’s Favourite Book: Elad Gil's High Growth Handbook As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Alfred Lin is a Partner @ Sequoia Capital, one of the world's most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom, Doordash and many more. As for Alfred, he has led deals in the likes of Airbnb, Doordash, Instacart, Reddit and Houzz to name a few. Prior to the world of venture, Alfred was Chairman and COO @ Zappos for 6 years leading to their acquisition by Amazon. In Today’s Episode You Will Learn: 1.) How Alfred made his way into the world of venture and came to be a Partner @ Sequoia? How Alfred first met DoorDash? Where did the meeting take place? Who was there? What were the first impressions? 2.) Market: How did Alfred breakdown the food delivery market when doing the diligence for the investment? How did Alfred forsee the market changing over time? What were some unexpected elements of the market Alfred did not forsee? What does Alfred look for in markets; size or growth? 3.) Competition: How did Alfred analyse the competitive landscape for food delivery at the time? Why does Alfred believe that great companies are not built by focusing on the competition? What does Alfred mean when he says, "you have to be customer-obsessed and competitor aware"? 4.) Traction: Does Alfred agree with Sarah Tavel in the dangers of chasing topline GMV? What negative behaviours can chasing GMV trigger? What does Alfred mean when he says, "founders have to be able to distinguish between input and output metrics"? 5.) Acquisition: What does Alfred believe DoorDash did so well in terms of acquiring drivers more efficiently? How did they retain them so effectively? What allowed DoorDash to compete so effectively when it came to merchant acquisition? What were some of Alfred's biggest takeaways when it came to DoorDash's customer acquisition journey? As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Phil Libin is the Founder and CEO @ mmhmm, the app that allows you to level up your remote presentations, making high-quality video content in minutes. To date, Phil has raised over $30M for the company from an incredible investor base including Sequoia, Kevin & Julia Hartz, Tony Fadell, Instagram's Kevin Systrom and Mike Krieger and Brianne Kimmel. Prior to mmhmm, Phil was a Managing Director @ General Catalyst and prior to his time in venture, Phil most famously founded Evernote, where he led the business with phenomenal success, as CEO for over 8 years. In Today’s Episode You Will Learn: 1.) How Phil made his way into the world of startups, came to found Evernote and how that led to his founding of mmhmm, most recently? 2.) How would Phil describe his management style today? How has it changed over time? Why does Phil believe shortcuts are the greatest mistakes startups make? What does Phil believe you can vs cannot take shortcuts on? What have been some real world lessons there? 3.) What were Phil's biggest takeaways from his time in venture? How did it change his operating mindset? Does Phil believe there is an incentive misalignment between founder and VC? Why is Roelof Botha the best board member Phil has worked with? What makes him so special? 4.) How does Phil think about the unbundling/verticalisation of Zoom? How does he predict the market evolving? How does Phil see the differing usage patterns between consumer and business? Why does Phil believe more can be learned from looking at similarities and not differences? 5.) What does Phil believe are the two classes of mistakes when scaling startups? What have been Phil's biggest lessons on acquiring and retaining the best talent? How does Phil create an environment of dissent where anyone can bring their entire self and beliefs to the table? Item’s Mentioned In Today’s Episode Phil’s Favourite Book: Kafka on the Shore As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Andrew Dudum is the Founder & CEO @ Hims & Hers, offering a modern approach to health and wellness and one of the fastest-growing companies to reach $1Bn. Prior to their going public on Tuesday this week, Hims raised over $158M from some of the best including Thrive, Forerunner, Founders Fund, IVP, Redpoint and more. As for Andrew, alongside his role at Hims he is also Co-Founder of Atomic, a company builder and venture fund all in one, backed by Peter Thiel and Marc Andreesen to name two. Prior to Atomic, Andrew led product at TokBox managing a team of 30 leading to their acquisition by Telefonica in 2012. In Today’s Episode You Will Learn: 1.) How Andrew made his way from Head of Product at Tokbox to venture capitalist with Atomic to changing healthcare with Hims? 2.) What are the biggest misconceptions people have with regards to what it takes to build a successful company? Why do you not need big teams? How can leaders drive efficiency within small teams? What have been Andrew's biggest lessons in acquiring the best talent in market? What works? 3.) Hims is the fastest company to scale to $1Bn, how does Andrew reflect on how he managed hyper-growth? What did he do well? What was the first to break? What would he do differently? When is the right time to go from generalist to specialist? When is the right time to add more products? 4.) Why did Andrew believe now was the right time to IPO just 4 years into the founding of the business? How did the SPAC process play out? What are the core advantages to Andrew of the SPAC over an IPO? Why will more founders use it in the future? How does Andrew assess the importance or lack of, when it comes to the pricing pop on IPO day? 5.) How does Andrew reflect on his relationship to money? Why does he feel more scared of it now than ever before? How does he think about bringing up his children with an appreciation and respect for money? What 3 traits would Andrew most like his children to have? Item’s Mentioned In Today’s Episode Andrew’s Favourite Book: The Planet Remade: How Geoengineering Could Change the World As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Josh Silverman is the CEO @ Etsy, leading the company as it builds a platform that empowers creative entrepreneurs around the world. Prior to their IPO, Etsy raised funding from some of the best in the business including Danny Rimer @ Index, Albert Wenger @ USV and Jim Breyer @ Accel to name a few. Prior to Etsy, Josh served as President of Consumer Products and Services at American Express, was the CEO of Skype, and CEO of shopping.com, and he held various executive roles at eBay. Josh is also currently on the board of directors of Shake Shack. In Today’s Episode You Will Learn: 1.) How Josh made his entry into the world of startups, came to be CEO of Skype and how he came to be CEO of Etsy? How did Josh's political background prepare him for being a public markets CEO? 2.) How does Josh think about 10 year plans? What is the right alternative? What does Josh do when he does not know what to do? How does Josh think about head vs heart in decision-making? How does Josh think about downside protection and risk mitigation with decisions? 3.) Why does Josh believe that you should, "never let a crisis go to waste"? How does he interpret that? Does Josh believe you learn more from success than failure? Why does Josh believe many succeed in spite of, not because of? How does Josh connote happiness to a milestone of success? What is true happiness for Josh? 4.) How does Josh think about winning today? What is the framework Josh believes founders need to put in place to optimise their chance of winning? How does Josh structure his team at Etsy to optimise for speed and experimentation? What has worked? What has not worked? 5.) How can leaders create a system where failure is minimised? How does Josh implement a "red hat vs green hat" decision making process around new ideas at Etsy? What question does Josh and the team ask with every experiment? How should one analyse the cost of rolling back a decision? 6.) How does Josh determine between dogma and good practice in a company? What is the right way to remove antiquated dogma without damaging morale? What were some of the biggest challenges from his doing this on entry at Etsy? Item’s Mentioned In Today’s Episode Josh’s Favourite Book: Grant As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ali Ghodsi is the Founder & CEO @ Databricks, bringing together data engineering, science and analytics on an open, unified platform so data teams can collaborate and innovate faster. To date, Ali has raised over $897M for the company including from the likes of a16z, NEA, Microsoft, Battery, Coatue, Greenbay and more. Prior to Databricks, Ali was one of the original creators of open source project, Apache Spark, and ideas from his research have been applied to Apache Mesos and Apache Hadoop. In Today’s Episode You Will Learn: 1.) How Ali made his way from fleeing Iran as a refugee to living in a Swedish ghetto? What was the founding moment for Ali with Databricks? 2.) How does Ali think about and evaluate risk today? Why does Ali always make his team do downside scenario planning? How does Ali think about his relationship to money today? Why does Ali disagree with gut decisions? What is his process for making decisions effectively? 3.) Stage 1: The Search for PMF: What are the core elements included in this phase? What types of leaders thrive in this phase? What type struggle? How can leaders sustain morale in the early days when it is not up and to the right? Who are the crucial hires in this phase? 4.) Stage 2: Scale Go-To-Market: What are the core roles needed to expand GTM fast and effectively? Why should you hire sales leaders before marketing leaders? Why is hiring finance leaders so crucial here? What mistakes are most often made here? How do the board resolve them? 5.) Stage 3: Process and Efficiency: What are the first and most important processes that need to be implemented? How does Ali need to change the type of leader he is to fit this stage? How does one retain creativity and nimble decision-making at scale and with process? Item’s Mentioned In Today’s Episode Ali’s Favourite Book: Good Strategy Bad Strategy: The Difference and Why it Matters As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Annie Duke is a former professional poker player and the author of National Bestseller, "Thinking in Bets" & "How To Decide". During her poker playing days, Annie was a World Series of Poker bracelet winner, the winner of the 2004 Tournament of Champions and the only woman to win the NBC National Poker Heads Up Championship. Today, Annie is also the founder of How I Decide, a non-profit that creates curricula and tools to improve decision making and critical thinking skills for under-served middle schoolers. In Today’s Episode You Will Learn: 1.) How Annie made her way from professional poker player to National Bestselling author and coach to the world's leading investors? 2.) How does Annie evaluate the nature of risk? What is good risk vs bad risk? How does Annie think through reversible vs irreversible decisions? What is her framework? Why does Annie believe most irreversible decisions are actually reversible? How does it change your thinking? 3.) How does effective solo-decision-making differ from effective group decision-making? What decision-making biases does Annie often see venture being guilty of making? What 3 things can one do to improve the decision-making of the collective group? 4.) How does Annie think about sunk cost? How does one know when enough is enough and you have to walk away? How does this tie into Annie's thinking on portfolio theory? How does Annie think about pre-mortems? How should they be structured? What is included? 5.) How does Annie define critical thinking? What tips would Annie give to someone in really advancing their level of critical thinking? What behaviours can one implement to seek to protect critical thinking? How does this differ in team environments? Item’s Mentioned In Today’s Episode Annie’s Favourite Book: The Success Equation: Untangling Skill and Luck in Business, Sports, and Investing As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Biz Stone is best known as the Co-Founder of Twitter and Medium. Biz is also an investor in the likes of Slack, Square, Intercom, Beyond Meat and Blue Bottle Coffee. Biz also co-founded Jelly, a "human in the loop" AI search service, which was acquired by Pinterest. Due to his many successes, Biz has been recognized as INC Magazine Entrepreneur of the Decade and one of TIME's 100 Most Influential People in the World. In Today’s Episode You Will Learn: 1.) How did Biz make his way into the world of startups and come to found Odeo/Twitter one day on a car trip with Ev Williams? 2.) How does Biz evaluate his relationship to money? How does Biz think about teaching his son the value of money? What does Biz mean when he says wealth 'accentuates your current self"? How did Biz get off the treadmill of always wanting and chasing more? 3.) How does Biz think about insecurity and self-doubt? How does Biz approach saying no? How does he get comfortable with not always being Mr Popular? What is so challenging here? How does Biz feel about founding tieing their identities to their company? 4.) Why did Biz come back to Twitter in 2017? With hindsight, what would he have done differently if he were to return again? What were the biggest challenges when he arrived? Why was internal morale low? What did he and Jack do to increase it? What worked? What did not? 5.) Why does Biz not feel Silicon Valley is an "insider-only" universe? Why does Biz feel Silicon Valley is a mindset? How does Biz think about the decentralisation of talent moving forward? How does Biz compare the UK to the US startup ecosystem? What is worse in the UK? Item’s Mentioned In Today’s Episode Biz's Favourite Book: Emergence: The Connected Lives of Ants, Brains, Cities and Software As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.    

Howard Marks is co-chairman and co-founder of Oaktree Capital Management, a leading investment firm with more than $120 billion in assets. Prior to founding Oaktree, Howard spent 10 years at The TCW Group, where he was responsible for investments in distressed debt, high yield bonds, and convertible securities. Howard has also written two books, most recently Mastering the Market Cycle: Getting the Odds on Your Side, and it was Warren Buffet who said, “When I see memos from Howard Marks in my mail, they’re the first thing I open and read. I always learn something.” Bill Gurley is a General Partner @ Benchmark Capital, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many many more. As for Bill, widely recognised as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix and Zillow. Prior to Benchmark, Bill was a partner with Hummer Winblad Venture Partners. Before entering venture, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at CS First Boston. In Today’s Episode You Will Learn: 1.) In March Ray Dalio stated we would be entering a "global recession", how do Howard and Bill feel about this statement? How does today's environment remind Howard and Bill of 2010/11? What is similar? What is different? How does Bill think about investing through cycles? 2.) How does Bill think about investing through cycles? What have Bill's lessons been from seeing many venture vintages on LP performance across cycles? How does Howard think about investing through cycles from a distressed debt perspective? What have his lessons been from Oaktree's performance over the years? 3.) Do Howard and Bill agree we will not see interest rates go anywhere for the next 3-5 years? What is the impact of this sustained low-interest rate environment? What could be done that would see interest rates increase in the future? How does Bill believe this will impact the supply of LP dollars in venture? 4.) How do Bill and Howard evaluate the state of the public markets today? Why does Howard believe that FOMO has really taken effect? How does Bill think about network effects and the laws of compounding with regards to public companies? 5.) Do Howard and Bill agree we are seeing a retreat from globalisation? What are the core impacts of this retreat? Why is Bill so concerned about "regulatory capture"? Why does Bill fear that today, "Washington is for sale"? What would he like to see change? Item’s Mentioned In Today’s Episode Howard’s Favourite Book: Across That Bridge: A Vision for Change and the Future of America Bill’s Favourite Book: How Innovation Works As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for all things 20VC.

Quentin Clark is a Managing Director @ General Catalyst, one of the most prominent firms of the last decade with a portfolio including Stripe, Airbnb, Snap, Anduril, Deliveroo and Cazoo to name a few. As for Quentin, at GC he has led deals in the likes of Kernel, Coda, Commure just to name a few. Before entering the world of venture Quentin was the CTO @ Dropbox and before that he was the Chief Business Officer @ SAP. Finally, before SAP, Quentin spent an incredible 20 years at Microsoft in a variety of different roles play a key part in their hyper-growth. In Today’s Episode You Will Learn: 1.) How Quentin made his way from CTO @ Dropbox and 20 years at Microsoft to being an MD with General Catalyst today? 2.) What were Quentin's biggest management takeaways from his 20 years at Microsoft? What is his favourite story about working with Bill Gates? How does Quentin think about the art of delegation? How does Quentin differentiate between leadership and management? 3.) How does Quentin believe the world of fundraising has changed with COVID? How does Quentin build relationships of trust in these compressed fundraising timelines? What works? What does not work? How can you really build that relationship off Zoom? How does this change the fundraising landscape moving forward? 4.) What does Quentin mean when he says he likes to "lead without authority"? How does that translate into his management style? How does Quentin evaluate his style of board membership? How does Quentin know whether to wear the investor vs the operator hat on the board? 5.) Does Quentin believe we are really moving the needle in terms of the projects that venture is funding today? What would Quentin like to see more of? What would Quentin like to change about the world of venture? How does Quentin evaluate market timing risk when investing? Item’s Mentioned In Today’s Episode Quentin’s Favourite Book: Stranger in a Strange Land Quentin's Most Recent Investment: Sprout Therapy As always you can follow Harry and The Twenty Minute VC on Twitter here!

Avlok Kohli is the CEO of AngelList Venture which has facilitated the funding of over 5,000 startups including 47 unicorns and is home to 4,300 funds and syndicates with $2.2B in assets under management. This year, AngelList Venture launched the much-discussed, Rolling Funds and Avlok recently launched his own rolling fund, Avlok Capital. Prior to AngelList, Avlok built and sold two companies; FastBite, acquired by Square in 2015 and Fairy, also acquired. If that was not enough, Avlok is also an angel in 25 companies. In Today’s Episode You Will Learn: 1.) How Avlok made his way into the world of facilitating over $2Bn in AUM having sold 2 prior companies on the other side of the table as a founder? What is Avlok's favourite Jack Dorsey story? 2.) Why does Avlok believe Rollings Funds are the "printing presses of innovation" for capital markets? Does Avlok believe that everyone should be a fund manager and managing capital? What are the benefits of rollings funds vs traditional micro funds? 3.) How does the rise of rolling funds impact the early stage pricing of companies? How does it impact the competitive landscape for seed and pre-seed allocations? Is Avlok concerned about a wave of undisciplined capital entering the market? 4.) How does Avlok evaluate reserve allocations for early stage and micro fund managers today? What does the data show for funds that do reserve for pro-rata vs those that do not? How has this impacted Avlok's own approach to pro-rata and reserve deployment? Item’s Mentioned In Today’s Episode Avlok’s Favourite Book: Meditations As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

David Hsu is the Founder & CEO @ Retool, the company that allows you to build internal tools, remarkably fast. David has raised over $69M with Retool from the very best in startups including Sequoia, YC, Patrick and John @ Stripe, Henrique & Pedro @ Brex, Paul Graham, Nat @ Github, Peter @ Segment, Tomer @ Gusto and Elad Gil to name a few incredible names. Today Retool works with some of the biggest companies in the world from Amazon to Volvo to Mercedes Benz. In Today’s Episode You Will Learn: 1.) How David made his way from studying philosophy at Oxford to creating one of the valley's hottest companies in the form of Retool? 2.) How does David analyse pivots today? How does one balance between vision and persistence vs realism and knowing when is the right time to pivot? How did a conversation with John Collison change the course of Retool? What advice does David have for founders on pivoting? 3.) Why does David believe that YC is useful pre-product-market fit but useless post-product-market fit? What elements are so helpful vs not about YC? Why did David raise his Series A as a split between Sequoia and prominent angels? Why was that transformational for the company? 4.) Why was David sceptical of VCs for a long time? Why does David believe VCs are useless pre-product-market fit and useful post-product-market fit? What have been David's biggest takeaways from working with Bryan Schrier @ Sequoia? 5.) Why does David believe that once you are profitable and growing it is actually quite hard to become unprofitable? How does David advise founders considering raising VC vs bootstrapping? How does David know when to allocate resources more aggressively to a segment? What are the signs? Item’s Mentioned In Today’s Episode David’s Favourite Book: Godel, Escher, Bach: An Eternal Golden Braid As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Dylan Field is the Founder & CEO @ Figma, the company that helps teams create, test, and ship better designs from start to finish and is one of 2020's fastest-growing companies. To date, Dylan has raised over $132M with Figma from some of the best including Sequoia, a16z, Index, Greylock, Founders Fund and Kleiner Perkins. Figma's latest round valued them at a reported $2Bn. Prior to founding Figma, Dylan enjoyed internships at Flipboard, LinkedIn and O'Reilly Media. In Today’s Episode You Will Learn: 1.) How Dylan made his way from an internship at O'Reilly Media and a Thiel Fellowship to founding Figma, one of the fastest-growing unicorns? 2.) How does Dylan feel about the future of education? What core questions do students need to ask before entering? How does Dylan assess the impact of the Thiel Fellowship today? Why does Dylan believe that everyone should be an intern? What did he take from that experience? 3.) How would Dylan describe his leadership style today? How has it changed over time? How did he get past micro-managing in the early days and learn to delegate? How does Dylan think about insecurity and vulnerability as a young leader today? 4.) What does Dylan foresee as the biggest challenges in Figma's transition from application to platform? How does Dylan evaluate the success of the Figma plugin ecosystem? How does Dylan think about the right cadence to roll out new products? How does Dylan think about catering to power users vs catering to the standard everyday user? 5.) What have been the most significant impacts of COVID for Figma? Why did Dylan choose to adopt a hybrid model for Figma in terms of working styles moving forward? What have been Dylan's biggest lessons of what it takes to attract the very best talent? What works? What does not? Item’s Mentioned In Today’s Episode Dylan’s Favourite Book: Snow Crash As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Johnny Boufarhat is the Founder & CEO @ Hopin, one of the fastest-growing companies on the planet, providing an online events platform where you can create engaging virtual events that connect people around the globe. In the last 13 months, Johnny has raised over $174M for Hopin from the likes of Accel, IVP, Slack, Northzone, Coatue, Salesforce and of course, 20VC Fund. With the funding, again in just 13 months, Johnny has grown the team from 10 people to over 210 people in 37 countries. In October of this year, Semil Shah awarded Hopin the label, "The Breakout Tech Startup Of 2020". In Today’s Episode You Will Learn: 1.) How Johnny made his way into the world of startups and how severe health challenges led to his realisation and founding of Hopin? 2.) What have been Johnny's biggest lessons scaling the team from 10 to 235 in just 12 months? What starts to break and when? What does Johnny believe are the 3 stages of startup growth? What have been Johnny's learnings on what it takes to acquire the very best talent? 3.) Why does Johnny believe that remote has so fundamentally changed the game? How does remote culture differ from physical culture? What advice does Johnny have for those shifting from physical to remote? Where does Johnny see so many make mistakes with the remote model? 4.) Why does Johnny believe fundraising is a game of leverage? How does Johnny advise founders to structure their raise? Should they shop their term sheets around? Should founders always be raising? How should they think through a pre-emptive round? How does COVID change the world of fundraising? 5.) What does the world of virtual events look like in a post COVID world? What events will remain virtual? What will not? How does Hopin expand beyond purely events into the much wider "connection" space? How does that look both from M&A and product expansion? Item’s Mentioned In Today’s Episode Johnny’s Favourite Book: Nineteen Eighty-Four As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Reid Hoffman is a Silicon Valley stalwart in the modern technology world. On the investing side, he is a Partner @ Greylock, one of the leading venture firms of the last 2 decades with a portfolio including Facebook, Airbnb, Dropbox, Figma, Appdynamics and Okta to name a few. Reid has led investments in Airbnb, Convoy, Coda and Aurora to name a few. As an operator, Reid co-founded LinkedIn, the world’s largest professional network and before LinkedIn, Reid served as executive vice president at PayPal, where he was a founding board member. If that was not enough, Reid is the co-author of Blitzscaling and two New York Times best-selling books: The Start-up of You and The Alliance.  In Today’s Episode You Will Learn: 1.) How Reid made his way into the world of startups, came to found Linkedin and how that led to his joining Greylock? 2.) Does Reid consider himself an innate and natural leader today? How has his leadership style changed over time? What elements does Reid struggle with? How has he scaled to these leadership challenges? What does Reid believe are the different strands of leadership? 3.) How does Reid think about what separates the good from the great board members? What is the biggest danger for board members today? How do the very best founders manage their boards? How does Reid think about the weight of his words today? 4.) How does Reid think about the importance of ownership? How does Reid analyse price today? What was the story behind Greylock investing in Airbnb? What did Reid see so clearly and before anyone else saw it? What is the story with Stripe? Why did Reid turn Stripe down? 5.) How does Reid think about ensuring venture partnerships always have a learning mindset? What can be done deliberately to ensure this? Where do many people struggle here? How can partners develop trust within venture partnerships? Where does trust most often break down? Item’s Mentioned In Today’s Episode Reid’s Favourite Book: Thinking, Fast and Slow, Amusing Ourselves to Death: Public Discourse in the Age of Show Business As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Katrina Lake is the Founder & CEO @ Stitch Fix, a multi-billion dollar public company, which has brought an entirely new model to retail apparel by combining data science, technology, and personal stylists, to create a unique shopping experience tailored to the individual consumer. Prior to their IPO in 2017, Katrina raised just $42M in venture funding from some of the best in venture including Bill Gurley @ Benchmark and Steve Anderson @ Baseline. In just 6 years Katrina took the company from founding moment to $2BN IPO and was even cash flow positive after just 3 years. If that was not enough, Katrina is also on the board of both Grubhub and Glossier. In Today’s Episode You Will Learn: 1.) How Katrina made her way from being an associate at a venture firm to reshaping the world of fashion with Stitch Fix? 2.) On reflection, is Katrina happy that the business was forced to be so capital efficient so early? What did Katrina do to structure the business and its inventory management to preserve cash? How does Katrina think about the balance between growth vs profitability? 3.) What have been some of Katrina's biggest lessons from working with Bill Gurley? How does Katrina ensure not to overweight his opinion on the board? What have been Katrina's biggest lessons on effective board management? How has being on the Grubhub and Glossier board changed the way she operates the Stitch Fix board? 4.) How does Katrina think about imposter syndrome and self-doubt today? How does she remedy it? How does Katrina ensure she remains on the front lines with customers despite being a public company CEO? What benefits are there for founders to stay in the trenches even when a large company? 5.) How does Katrina think on the importance for founders to have a vision today? Where do they need to be flexible? What are some dangers or pitfalls associated with "the vision"? How far are Stitch Fix along in cementing their vision? Item’s Mentioned In Today’s Episode Katrina’s Favourite Book: Between The World And Me As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Vlad Tenev is the Co-Founder & CEO @ Robinhood, the company that provides commission-free investing, plus the tools you need to put your money in motion. To date, Vlad has raised over $2.2BN with Robinhood from some of the very best in the business including Sequoia, Greenoaks, Index, DST, Ribbit, IVP, Thrive, NEA, GV and more incredible names. Before Robinhood, Vlad started two finance companies in New York City. In Today’s Episode You Will Learn: 1.) How Vlad made his way from Bulgaria to studying Math at Stanford to founding one of the fastest-growing companies of the decade in Robinhood? 2.) How does Vlad describe his own style of leadership today? How has this changed with the scaling of the business? What phase has been the most challenging? Why does Vlad think so much about "the tempo" of the company? What can you do to ensure the highest tempo? 3.) How does Vlad think about self-doubt as a leader when recognising the sheer size of the Robinhood team today being over 1,000? How does Vlad analyse the role that fear has to play in leadership? How does Vlad manage the weight of expectation? What works? What does not? 4.) What have been Vlad's lessons in what it takes to acquire the very best talent? Where do many founders make mistakes here? How does Vlad think about the role of mentorship with young team members? Why and how does Vlad bet so big on giving young team members responsibility? 5.) How does Vlad assess the current state of the fintech landscape today? Does Vlad believe we are entering a period of bundling or unbundling? Will we see the continued rise in the M&A activity we saw earlier this year? Why? What is likely to change in 2021? Item’s Mentioned In Today’s Episode Vlad’s Favourite Book: The Mars Project As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Sarah Tavel is a General Partner @ Benchmark, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many more. As for Sarah, prior to joining Benchmark, she was a General Partner at another globally renowned firm, Greylock, where she led deals in Sonder and Gixo. Pre-Greylock, Sarah was the first PM @ Pinterest where she led three acquisitions, launched Pinterest internationally, and was responsible for closing their $100m Series C financing. 20VC: Benchmark's Sarah Tavel on Why Chasing GMV Will Lead To The Wrong Direction, The 2 Crucial Tipping Points For Marketplace Adoption, Why UGC Plays Are Like Marketplaces & How To Determine Between Existential and Non-Existential Risk In Today’s Episode You Will Learn: 1.) How Sarah made her way from being the first PM at Pinterest to being a General Partner at one of the world's leading venture firms, Benchmark? 2.) What does Sarah mean when she says, "the small things are not the big things"? How does Sarah determine between existential vs non-existential risk? How does this impact the type of board member Sarah is? How has Sarah seen the best board members engage? Who are they? 3.) Why does Sarah believe that in marketplaces, chasing GMV will lead you in the wrong direction? How does Sarah think about good vs great when it comes to 1.) Average order values? 2.) Repeat purchase rates. 3.) NPS? 4.) Net revenue retention? How should they change with time? 4.) In marketplaces, what is a tipping point? What are the 2 crucial tipping points to be aware of? How can marketplaces ensure demand brings further demand? What can they determine from how demand engages with different suppliers? How does Sarah feel about feedback systems? 5.) Why does Sarah believe that UGC plays are like marketplaces? What lessons can be drawn from TikTok to suggest this? How does Sarah think about her biggest lessons when analysing the growth of DoorDash? What do many not see that is important to recognise? Item’s Mentioned In Today’s Episode Sarah’s Favourite Book: Pachinko: The New York Times Bestseller As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Alexis Ohanian is the Founder @ Seven Seven Six, his new fund which just recently announced their first investment leading the $4M seed round for Dispo. Prior to founding Seven Seven Six, Alexis was the Co-Founder & Managing Partner @ Initialized Capital, where he backed many a unicorn including Ro, Flexport, Patreon, GOAT just to name a few. Alexis is also the co-founder @ Reddit, commonly referred to as the front page of the internet, their latest valuation priced the company at $3Bn. In Today’s Episode You Will Learn: 1.) When Alexis left his L Sats to go get waffles, what did he learn about himself? How did that lead to founding Reddit? How did Reddit lead to angel investing? How did that lead to Initialized? 2.) Why did Alexis leave Initialized? Why was now the right time? What worked with Initialized that he has taken with him to Seven Seven Six? What did not work with Initialized that he has learned from? How does he view VC NPS as a result of this and the learnings? 3.) How does Alexis analyse his own relationship to money today? How did his relationship with his mother and her illness impact how he thinks about wealth and happiness? How did he feel when at 22 he sold Reddit? How does he feel about the "keeping up with the Jones'" mentality? 4.) How did having Olympia change how Alexis operates and invests today? How does Alexis define backing projects he would be proud to talk to Olympia about? How does he feel about the type of deals many investors make today? 5.) How did Alexis first meet PG from YC? How did he feel when he heard he believed in him and Steve with Reddit? How did that change how Alexis feels about being the first person to really back someone? Item’s Mentioned In Today’s Episode Alexis’ Favourite Book: Superforecasting: The Art and Science of Prediction Alexis’ Most Recent Investment: Dispo As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Stewart Butterfield is the Founder & CEO @ Slack, the leading channel-based messaging platform, used by millions to align their teams, unify their systems and drive their businesses forward. Prior to their direct listing in June 2019, Stewart raised over $1.3Bn from the likes of Accel, Thrive, Softbank, Kleiner, IVP, T Rowe, GV and a16z to name a few. Prior to founding Slack, Stewart co-founded Flickr, a company he built into one of the largest web services in the world. Due to his many incredible successes, Stewart has been named to the 100 Most Influential People in the World by Time Magazine, and one of the Top 50 Leaders by BusinessWeek. In Today’s Episode You Will Learn: 1.) How Stewart made his way into the world of startups and came to found Flickr? What was his founding moment for the Slack journey? 2.) How does Stewart think about and assess his relationship to money? How has it changed over time? What does Stewart believe are the 3 levels of wealth? How does Stewart think about his identity being tied to the company? Is that a challenge? How does he mitigate it? 3.) How does Stewart describe his management style and philosophy today? How has it changed over time? How does Stewart approach reversible vs irreversible decisions? How does Stewart structure post-mortems? Why does Stewart believe effective entrepreneurship is like parkour? 4.) How does Stewart think about and advise on the debate between direct listing, IPO and SPAC? What has been better/worse and different since making the transition to being a public company? What have been some of the biggest surprises? 5.) Why does Stewart believe that for most companies, comprehension is the reason for the lack of adoption and customer acquisition? How does he look to solve that with Slack? What have been their biggest mistakes on messaging and branding? Item’s Mentioned In Today’s Episode Stewart’s Favourite Book: Leadership and Self-Deception: Getting Out of the Box, Crucial Conversations Tools for Talking When Stakes Are High, The Courage To Be Disliked As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Dan Levine is a Partner @ Accel, one of the world's leading venture firms with a portfolio including the likes of Facebook, Slack, Qualtrics, UiPath and Deliveroo. As for Daniel, he actually joined Accel in 2010 before leaving to join Dropbox. At Dropbox, he worked on the platform team helping open the platform to third-party developers and launched and managed many of the company’s developer-facing initiatives. Following Dropbox, he rejoined Accel and has led investments in Scale.ai, Mux, Vercel and Sentry to name a few. In Today’s Episode You Will Learn: 1.) How Dan made his way into the world of venture with Accel? How that led to his joining Dropbox? What led to his re-joining Accel 3 years later? 2.) How does Dan assess the current state of the seed and Series A landscape? How does Dan analyse the rise of pre-emptive rounds? How does Dan determine when to lean in and pre-empt vs when not to? What does Dan think is the biggest myth about raising a Series A? 3.) How does Dan analyse multi-stage funds so actively entering seed? What has Accel's seed portfolio data shown? How many went on to raise a Series A? How many did Accel lead? How many companies died? What is the biggest problem this portfolio presents? 4.) How does Dan analyse the trio of people, product and market? How does Dan approach market sizing? How does Dan approach the risk associated with market timing? What risk is he willing to take? What is he not? When can one stretch on market? When is it a stretch too far? 5.) How does Dan evaluate the rise of solo capitalists? What does he see as the core pros and cons of the model? What are the pros and cons of the partnership model like Accel has? How does Dan evaluate the rise of investor personal brands today? What worries him? Item’s Mentioned In Today’s Episode Dan’s Favourite Book: Titan: The Life of John D. Rockefeller, Sr. (Vintage) Dan’s Most Recent Investment: Altinity As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Derek Zanutto is a General Partner @ CapitalG, Alphabet’s independent growth fund with investments in the likes of Stripe, UiPath, Looker, Robinhood and Lyft to name a few. At CapitalG, Derek has led investments in Collibra, Dataiku and Armis as well as sitting on numerous boards. Prior to CapitalG, Derek spent a decade investing in such companies as Uber, Airbnb, Lynda.com and CAA at investment firms TPG, Hellman & Friedman and GIC. In Today’s Episode You Will Learn: 1.) How Derek made his way from the world of TPG and growth equity to being a GP with Alphabet's independent growth fund, CapitalG? 2.) Does Derek agree with Bill Gurley, "the biggest challenge is the over-supply of capital"? How does Derek see this changing with interest rate changes or lackof? How do interest rate changes impact later stage pricing? How does Derek assess his own relationship to price? 3.) How does Derek approach investments thinking through the bundling vs unbundling lens? What have been some core examples of this over the last decade? How does Derek assess market timing risk? What risks is he willing to take? How does he build a thesis ahead of meeting companies? 4.) What does Derek make of large later stage firms moving earlier and doing Seeds and Series A's? What do entrepreneurs need to know about these firms? What does Derek think about early-stage firms scaling into multi-stage firms? Why is stage specificity so important? 5.) What are the core economics of venture capital that all entrepreneurs need to understand? How do different GPs and funds have different motivations according to fund size? How do different funds approach carry allocation and fees? Why does this matter to founders? Item’s Mentioned In Today’s Episode Derek’s Favourite Book: Sapiens: A Brief History of Humankind Derek’s Most Recent Investment: Armis As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.    

Zach Weinberg is a Co-Founder of Operator Partners, operators funding operators, with no outside LPs, just their own capital. Fun fact, 20VC Fund has actually invested with them in 3 companies from Alt, Dooly.ai and Boom Pay. Prior to founding Operator Partners, Zach was the Co-founder/COO of Flatiron Health (acq @Roche for $2b) and before Flatiron Zach co-founded Invite Media (acq @Google for $81m). If that was not enough, Zach has also been an incredibly successful angel in the past with a portfolio including RigUp, Ro, Color, BlueApron and Plaid to name a few. In Today’s Episode You Will Learn: 1.) How Zach made his way into the world of startups, came to found Flatiron (acq for $2Bn) and how that led to Operator Partners? 2.) How does Zach analyse his own personal capital allocation? How much in funds? How much in cash, equities, direct, credit etc etc? How does Zach analyse his relationship to money? How has it changed over time? How does Zach evaluate his relationship to risk? 3.) What does Zach make of the rise of pre-empted rounds? When should founders takem them vs reject them? How does Zach feel about multi-stage funds re-entering seed aggressively? How does he advise founders? What are the pros and cons of having multi-stage money? 4.) How does Zach think about the importance of ownership? How does Zach analyse the re-investment decision? How does he approach reserve allocation? How does Zach reflect on his own price sensitivity? How has his relationship to price and ownership changed with time? 5.) How does Zach feel about Brian Armstrong's piece on employees bringing their own political and external beliefs into the workplace? Why does Zach believe that companies are not a democracy? Why does Zach believe that we do not live in a democracy any longer? Item's Mentioned In Today's Episode Zach's Favourite Book: Calling Bullshit: The Art of Skepticism in a Data-Driven World Zach's Most Recent Investment: David Energy As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Barry Eggers is a Founding Partner @ Lightspeed Venture Partners and currently Chair of the National Venture Capital Association (NVCA) Board of Directors. Lightspeed is one of the premier funds of the last decade with homeruns including Snapchat, Affirm, Mulesoft, Nutanix and Stitch Fix. Prior to LSVP, Barry spent close to 6 years as @ Cisco developing Cisco's initial M&A program and leading the company's first wave of acquisitions and integrations. In Today’s Episode You Will Learn: 1.) How Barry made his way into the world of venture over 20 years ago and how he came to found one of today's leaders, Lightspeed? 2.) What are the implications of a Biden administration? How does this compare to a Trump administration? What can be done to mitigate the tax concerns around Biden's policies? How does Barry think about each candidate's stance on immigration? What are the challenges here? 3.) How will SPACs change the world of venture? What will it take for them to be viewed in the same class as IPOs? Why are they often better than direct listings? How does the rise of solo capitalists change the state of venture? What does Barry make of rolling funds being born? 4.) What does Barry believe we can do to swing the race pendulum in venture? What were Barry's biggest lessons in taking the Lightspeed partnership from 1 to 10 female partners? How can this be done with ethnic minorities also? What advice does Barry give to his counterpart GPs? 5.) How would Barry describe his own style of board membership? How has it changed over time? How does Barry keep his head in boards with many around him are losing theirs? What advice does Barry give to new board members adopting board seats for the first time? Items Mentioned In Today’s Show: Barry’s Favourite Book: Channel Kindness: Stories of Kindness and Community As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

David Helgason is the Founder @ Unity, the company that gives content creators the tools to create innovative RT3D experiences and deliver better processes for almost every industry. Prior to their IPO in 2020, Unity raised from the likes of Sequoia, Thrive, DFJ, SilverLake and then individuals including Max Levchin and VMWare's Diane Greene. If that was not enough, David is currently a Partner @ Nordic Makers, a group of ten top Nordic angels working together to be the best angel investors in the Nordics. David also serves on the board of Labster, Realm.io and Quizup. In Today’s Episode You Will Learn: 1.) How David made his way from founding Unity in a cafe in Denmark to the $10Bn+ public company it is today? 2.) How would David describe his leadership style? How has it changed over time? What were the biggest challenges David faced as the Founding CEO? 3.) What was the decision-making behind David's transition out of the CEO role? What was challenging? What was key to make the transition successful? How did David know John Riccitiello was the right person for the role? How does David advise other founders contemplating the same? 4.) How does David analyse his own board management style? What are the most important elements a board member can do to help the company and founder? What makes Roelof Botha such a special board member to have? How does David advise new board members today to be successful? 5.) Why does David believe running a company is like a liberal art? How does David think about the importance of vision? How does David assess the current state of the European tech landscape? What can be done to improve it? How can investor approach change for the better? As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Roleof Botha is a Partner @ Sequoia Capital, one of the world’s leading venture firms with a portfolio including the likes of Airbnb, Instacart, Stripe, UiPath, Zoom, the list goes on. As for Roelof, at Sequoia he has led rounds into the likes of YouTube, Instagram, Eventbrite, Square, MongoDB, 23andMe and Unity Technologies to name a few. Before joining the world of venture, Roelof was the CFO @ Paypal playing a key role in their hyper-growth from 2000-2003. In Today’s Episode You Will Learn: 1.) How did Roelof go from actuary in South Africa to CFO @ Paypal? What were his biggest lessons from seeing Paypal burn $10M per month? How did Paypal lead to his joining Sequoia as a Partner? 2.) Market Evaluation: Does Roelof agree that the market is crazy today? How does today compare to prior vintages? How does Roelof assess the compression of fundraising timelines? With compressed timelines, how does he build relationships of trust with founders? 3.) Founder Evaluation: What were Roelof's lessons on founder assessment from Don Valentine? What matrix did Don teach Roelof to assess founders on? How does Roelof feel about the rise of competitive rounds? When should founders take them vs remain heads down on execution? 4.) Investment Mentality: How did Roelof prevent becoming too confident when early investments went well? How does Roelof prevent relying on past failures as a reason for turning down opportunities today? What can investors do to retain a very flexible mind? Why does Roelof believe you are only as good as your next investment? 5.) Sequoia's Edge: How does Roloef think about what it takes for Sequoia to retain it's edge at the top? How does Roloef measure the success of the Sequoia scout program? How did they structure it? How has the structure changed? What do they plan to do moving forward? 6.) Board Membership: How would Roloef evaluate his current style of board membership? How has that style changed over time? What elements did he find challenging? What advice would Roelof give to new board members adopting their first board seats? Items Mentioned In Today’s Show: Roelof’s Favourite Book: Man's Search For Meaning Roelof’s Most Recent Investment: mmhmm As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.    

Eoghan McCabe is a technology entrepreneur. He's started a number of companies, the most notable of which is Intercom, the conversational relationship platform. He was CEO of Intercom for nearly 10 years, during which he grew the company to hundreds of millions in annual revenue, nearly 700 employees, and raised nearly $250M from the likes of Kleiner Perkins, Index, Bessemer, and ICONIQ. He's also invested in dozens of companies including Stripe, Figma, SuperHuman, and Coda. In the summer of 2020 he moved to the role of Chairman of Intercom. In Today’s Episode You Will Learn: 1.) How Eoghan made his way into the world of startups from Ireland and came to build one of the Valley's greats with Intercom? 2.) How does Eoghan thinking about living and thriving with a chip on one's shoulder? What does Eoghan advise in terms of one's search for their true selves? What were his biggest learnings in his search? What does Eoghan advise people who maybe feel they have lost themselves? 3.) Having been CEO of a $Bn company for close to 10 years, how does Eoghan think about dealing with the weight of expectation placed on shoulders? How did he manage it? How does he think about his identity being so tied to his company? 4.) In terms of being one's authentic self, how can one achieve this while also respecting their stakeholders who may hold different views? How does Eoghan think about being an authentic leader vs bowing down to the demands of your team? What is the right balance? 5.) Why does Eoghan think that vision can actually be limiting? How does Eoghan think about stress testing one's vision and ambition? What adversity from early VCs did Eoghan have to fight against? How does Eoghan encourage dissent and debate within his teams? Items Mentioned In Today’s Show: Eoghan’s Fave Book: Breathe: simple breathing techniques for a calmer, happier life As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Cyan Banister is one of the most successful and renowned early-stage investors of the last decade. Her portfolio includes the likes of SpaceX, Uber, Affirm, Opendoor Postmates, Niantic and Thumbtack to name a few. Today Cyan is a Partner @ Long Journey Ventures, joining the team there following a 4-year stint @ Founders Fund where she led deals in both Niantic and HQ Trivia. Prior to Founders Fund, Cyan was a super successful operator and angel, co-founding Zivity and before that being an early employee at Ironport, leading to their acquisition by Oracle. In Today’s Episode You Will Learn: 1.) How Cyan made her way into the world of startups? How SpaceX came to be her 1st angel investment? How that led to her joining the world of VC? 2.) How does Cyan think about and assess her relationship to money? Why does someone believe she had a fear or loathing of money? What made Cyan the capitalist she is today? How does Cyan analyse her relationship to risk? Has Cyan always trusted her own convictions? 3.) How does Cyan think about her own investment decision-making process? What were Cyan's biggest lessons from her experience with HQ Trivia? How did she change how she interacts with founders pre-investment? Why does Cyan never Google someone before meeting? 4.) How does Cyan think about price sensitivity today? Why does she believe there will be a reckoning? How will this shake out in terms of who succeeds and who fails? Why is Cyan in favour of party rounds? How does she think about VCs with sharp elbows? 5.) Why does Cyan believe SF is eating itself? What can be done to reinvigorate the city positively? What can be done to solve much of the homelessness problem? Why does Chesa Boudin never convict anyone? Why does Cyan believe her "BLM tweet is not spicy"? Why is Cyan fundamentally sad and worried for the current state of the world? Items Mentioned In Today’s Show: Cyan’s Fave Book: Snow Crash As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.    

Spike Lipkin is the Founder & CEO @ Newfront Insurance, the modern insurance brokerage empowering risk management experts with advanced technology to deliver innovative solutions to their clients'. To date, Spike has raised from some of the best in the business including Founders Fund, Meritech and 20VC Fund. Prior to founding Newfront, Spike was one of the first employees at Opendoor, where he helped grow the team from 5 people to an enterprise value of over $5Bn today. Prior to Opendoor, Spike was an investor at Blackstone, where he served on the startup team that built Invitation Homes into the largest owner of single-family real estate in the United States. In Today’s Episode You Will Learn: 1.) How Spike made his way from banking to be one of the first operators at Opendoor to founding the next generation of insurance with Newfront? 2.) What were some of the biggest takeaways for Spike from his time at Opendoor as employee #5? How does Spike approach prioritisation? How does he determine what to delegate vs what to control? 3.) How would Spike describe his own style of leadership? How has Spike needed to change his style with the business? What does Spike believe is his biggest weakness as a leader? What is he doing to confront it and grow as a leader? What is the most important thing a leader can do? 4.) How does Spike think about what it takes to acquire the very best talent? What does his framework for hiring look like? Why did Spike decide to hire a COO? Why was then the right time? How does Spike think about the balance between hiring external vs promoting internal? 5.) Why did Spike believe it was important not to announce any of his prior fundraises? How did Spike approach investor selection with Newfront? Does Spike believe founders should meet with VCs between fundraises? Which angel has done the most to move the needle for the company? How? Items Mentioned In Today’s Show: Spike’s Fave Book: Team of Rivals: The Political Genius of Abraham Lincoln As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

George Zachary is a General Partner @ CRV, one of the nation's oldest and most successful early-stage venture capital firms with a portfolio including the likes of Airtable, DoorDash, Dropbox, Niantic and many more. As for George, today at the firm he focuses on advancing health through revolutionary computer science, centred around bio-engineering. During his incredible 16 year tenure at CRV, he has led deals in the likes of PillPack, Udacity, Scribd and HealthIQ. Before joining CRV, George was a General Partner @ Mohr Davidow Ventures for over 6 years. In Today’s Episode You Will Learn: 1.) How George made his way into the world of venture over 21 years ago and how he came to be a General Partner @ CRV 16 years ago? 2.) How did seeing the booms and busts of the dot com and 08 impacts George's investment mindset? What is the right way to voice concerns in an internal investment discussion? How does George now view capital intensity? How does it impact his conviction and check size? 3.) Why does George believe one should invest in founders who do not need their investors help? Why does George believe the best founders have experienced some form of parental instability? How does George detect the psychological need to win when he meets founders? What are the signs? 4.) How would George describe his own philosophy of board membership? How has it changed over time? What are the 2 control functions that a board member has? What advice does George give to new board members today? Where do many young board members make mistakes? 5.) How does George analyse his own personal relationship to money? How has it changed over the years? How did his relationship to money change his relationship with people? Was that challenging? How did he cope with it? How does he advise others who experience the same? Items Mentioned In Today’s Show: George's Favourite Book: Foundation Trilogy George’s Most Recent Investment: Glympse Bio As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

David Lawee founded CapitalG, Alphabet’s independent growth fund, in 2013, drawing on his experience both at Google and as a serial entrepreneur. Since then, he has helped transform high-potential startups into some of the most highly valued businesses of our generation, including Airbnb, Lyft, Snap, Robinhood, Credit Karma, Oscar, Lending Club and Thumbtack. Prior to CapitalG, David played a pivotal role in Google’s growth story--first as Google’s Chief Marketing Officer and then as the instrumental VP of corporate development where his group spearheaded over 100 acquisitions for the company. CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) How David made his way into the world of startups, came to be the first CMO @ Google and how that led to his founding CapitalG? 2.) Having operated and invested through both the dot com and 08', how has seeing the booms and busts impacted David's investing mindset? How does David think about temporal diversification today with CapitalG? Why does David believe diversification is largely overrated? 3.) How does David think about portfolio construction today, given CapitalG is a growth fund? How does David compare early-stage to growth today? How does David think about loss ratios at growth? How does David benchmark good vs great from a multiple perspective at growth? 4.) How does CapitalG approach investment decision making today? How does David avoid consensus thinking/following the crowd when it comes to deals? Why does David believe investment clubs operate much more successfully than partnerships? How does that change the structure for CapitalG? 5.) How has David seen himself evolve and develop as a board member of the years? What type of board member would David say he is today? How does that change with the founder? Who is the most memorable board member David has sat on a board with? Items Mentioned In Today’s Show: David’s Fave Book: Born A Crime: Stories from a South African Childhood  David’s Most Recent Investment: Albert As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Arlan Hamilton is the Founder and Managing Partner @ Backstage Capital, the seed fund that has paved the way investing exclusively in startups that are led by underrepresented founders. Backstage Capital also expanded their model and now have Backstage Accelerator working with companies across 4 cities. Last month, Mark Cuban gave Arlan $6M to invest in underestimated founders (ArlanWasHere Investments Fund I). Arlan is also an Author of "It's About Damn Time". If you would like to invest with Arlan, you can, check out BackstageCrowd.com with over 2,000 accredited and non-accredited investors, they just completed their 6th deal and $1m raised within 3 months of launch. In Today’s Episode You Will Learn: 1.) How Arlan made her way from the airport floor to founding her own venture firm, Backstage Capital and writing a book, "It's About Damn Time"? 2.) How does Arlan assess her own relationship to money and wealth? What is Arlan's thinking around her desire to give away 90% of her wealth? How does Arlan evaluate her own appetite for risk? How has that changed over time? 3.) From a strategic perspective, what are some core elements to Arlan's strategy that are not obvious? What are the main misconceptions that remain with regards to under-represented founders? What does Arlan believe are the leading indicators when assessing founders today? 4.) What does Arlan believe have been the biggest challenges in building the firm that is Backstage? What have been the core breaking points in the scaling of people and strategy? How does Arlan think about the relationship between brand vs reputation? What does Arlan believe are the main misconceptions people have about her? 5.) How would Arlan like to see the world of venture change over the next decade? What can LPs do to encourage more under-represented founders are backed? How can this be measured? Who should be held accountable? Items Mentioned In Today’s Show: Arlan’s Fave Book: What I Know For Sure by Oprah Winfrey As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Katherine Boyle is a Partner @ General Catalyst, one of the leading venture firms of the last decade with a portfolio including the likes of Stripe, Snapchat, Airbnb, Canva, Cazoo, the list goes on. As for Katherine, at GC she has led deals in game-changing companies such as Anduril, Nova Credit, Spring Discovery and Airmap to name a few. Prior to General Catalyst, Katherine entered the world of venture with Founders Fund and before that spent an incredible 4 years at The Washington Post where Katherine investigated entrepreneurship in many forms. In Today’s Episode You Will Learn: 1.) How Katherine made her way from investigating entrepreneurship at The Wall St Journal to being an intern at Founders Fund to today, being a Partner @ General Catalyst? 2.) Why does Katherine believe that journalism is like venture? Why does Katherine believe there are two different styles of venture? What were Katherine's biggest takeaways from her formative years in venture with Founders Fund? How did that impact her investing mindset? 3.) What does Katherine mean when she says she "invests solely on founder narrative fit"? Are there leading indicators of this fit? What advice did Katherine take from her conversation with Mike Moritz pre VC career? How does Katherine strategically avoid consensus thinking and decisions? 4.) How does Katherine approach market sizing? How does Katherine think about strategic insertion into niches that expand to much larger markets? How does Katherine assess market timing? How does Katherine determine the velocity of a market tailwind? What is an example of this? 5.) How does Katherine evaluate the rise of pre-empted rounds today? What advice does Katherine give to founders considering taking multi-stage money at seed? Why did it make sense for Anduril? How does Katherine gain the time of the founders when they are not raising? Items Mentioned In Today’s Show: Katherine’s Fave Book: The Decadent Society: How We Became the Victims of Our Own Success Katherine’s Most Recent Investment: Ophelia As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Palmer Luckey is the Founder @ Anduril Industries, founded on the premise of radically transforming the defence capabilities of the United States and its allies by fusing artificial intelligence with the latest hardware advancements. To date, Palmer has raised over $385M with Anduril from Founders Fund, a16z, Elad Gil, Spark Capital, Lux Capital, General Catalyst and 8VC to name a few. Prior to changing the world of defence, Palmer founded Oculus VR where he designed the Oculus Rift. Oculus VR was acquired by Facebook for $2.3Bn in 2014. In Today’s Episode You Will Learn: 1.) How Palmer made his way into the world of startups, made his way from trailer to selling Oculus for $2.3Bn to changing the defence industry with Anduril today? 2.) How does Palmer evaluate his own relationship to money? How has that changed since his $2.3Bn Oculus exit? How does Palmer assess his relationship to risk? How does Palmer approach the correlations between money, risk and happiness? 3.) What were some of Palmer's biggest takeaways from his time scaling Oculus? How have they informed his mindset with Anduril? What worked? What did not work? How has Palmer changed as a leader? How does Palmer approach personal development? How does he optimise for it? 4.) Palmer scaled Oculus to 1,400 people in 1 year, where do organisations break with scale? Why does Palmer believe, "you never want to play yourself"? Where does he feel his biggest weakness is as a scaling leader? How does Palmer approach hiring at scale yet maintaining culture? 5.) From a defence standpoint, why does Palmer feel the US needs to be more like the Chinese? Why is the DoD so poor at investing in innovation? What does it take to sell into the DoD really effectively? Why have the only 2 successful defence companies been founded by billionaires? Items Mentioned In Today’s Show: Palmer’s Fave Book: The Three-Body Problem As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Shishir Mehrotra is the Founder & CEO @ Coda, the startup that brings all of your words and data into a flexible all-in-one doc. To date, Shishir has raised over $140M from some great names including Greylock, Kleiner Perkins, General Catalyst, NEA and Homebrew to name a few. Prior to founding Coda, Shishir spent an incredible 6 years at Google in a couple of different roles; first as Director of Product for Youtube Monetisation and then moving to Youtube VP of Engineering, Product and UX. Before Google, Shishir was with Microsoft for 6 years as a Director of Program Management. Shishir also serves on the board of Spotify. In Today’s Episode You Will Learn: 1.) How Shishir made his way into the world of tech, came to be VP of Engineering, Product and UX @ Youtube and how it led to founding Coda? 2.) What is the No 1 quality of a good decision? How does Shishir think through reversible vs irreversible decisions? What are the 4 phases of decision-making? When should decisions be based on speed vs not? How can teams adjust questions to come to more productive outcomes? 3.) How does Shishir encourage debate and dissent within team discussions? How can leaders build deep trust with their teams? How can leaders create true democracy for idea sharing and meritocracy? Should ideas always be acted on immediately? What are the pros and cons? 4.) How does Shishir think about and evaluate his own operating cadence? How has this changed over time? How does Shishir approach time allocation? What have been his core learnings? How does Shishir divide his time between proactive and reactive tasks? 5.) How does Shishir approach OKR setting? What can leaders do to create aspirational and inspirational goals? How should goals be correctly communicated across orgs? How many OKRs should one team/person have? How should attribution across OKRs be given? Items Mentioned In Today’s Show: Shishir’s Fave Book: Switch: How to change things when change is hard  As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Alex Pall and Drew Taggart are the Founders of The Chainsmokers and Mantis. The Chainsmokers are one of the most sought after musical acts of our time. As for Mantis, just last week they announced their first $35M venture fund and have backing from Ron Conway, Mark Cuban and Keith Rabois. They have already invested in hotly contested rounds for Fiton and Loansnap. Drew and Alex also own a production studio, are stakeholders in the spirit brand JaJa Tequila and last year co-founded the anti-scalper ticketing platform Yellowheart. In Today’s Episode You Will Learn: 1.) How Drew and Alex made their way into the world of tech and startups and how they came to found a venture firm with Mantis? 2.) Why did Alex and Drew decide now was the right time for the fund? What did they look for in their LPs? How do they use their LPs to strategically help their companies? What is their preferred stage, sector? Do they have ownership requirements? 3.) Are Alex and Drew nervous about making the move into venture? If everyone has a chip on their shoulder, where does the chip on their shoulder come from? How do they think about their own vulnerabilities? How do they manage them? What works? What does not? 4.) What ways do Alex and Drew most like to work with their founders? Where do they provide outsized value? What are some examples of this? How do they think about working with VCs to get into the best rounds? How do they want to position Mantis in the ecosystem? 5.) With the tequila brand, the film production company and now the venture fund, how do they think about the expansion of "The Chainsmokers Empire"? What does this look like in 10 years? How would they like it to expand and grow? Items Mentioned In Todays Episode Drew's Favourite Book: The Unbearable Lightness of Being As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Austen Allred is the Founder & CEO @ Lambda School, the startup that remotely trains people to become a web developer or data scientist and the students pay no tuition until they are hired. Just last month, Lambda's $74M Series C was announced led by Gigafund bringing their total funding to date to over $129M with prior investors including Stripe, Bedrock, GV, Gigafund and GGV to name a few. Prior to founding Lambda, Austen was Senior Manager for Growth @ LendUp and before that co-founded Grasswire. In Today’s Episode You Will Learn: 1.) How Austen made his way into startups having slept in a Honda Civic and how he went from homeless to rockstar founder @ Lambda? 2.) How does Austen evaluate his own attitude to risk? How does Austen think about downside protection today? How has this changed over time? How does Austen feel about founders taking secondaries? How does Austen think about his own relationship to money? 3.) Having raised his Series C last month, why did Austen choose the investors he did? How did the round progress? What made Gigafund different to alternate options? What makes the best board members in Austen's mind? What makes the worst? 4.) What have been the most challenging elements for Austen of scaling the team? How does complexity change with time in team scaling? Why did Austen bring in a COO? What did he look for in the role? How does Austen advise others on bringing in a COO? 5.) Why does Austen believe that post-COVID we will never go back to the valley as we knew it? Why does Austen believe the valley represents the biggest potential squandering of wealth in history? How does Austen evaluate the government intervention we have seen? As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ravi Gupta is a Partner @ Sequoia Capital, one of the world's leading venture firms with a portfolio including the likes of Airbnb, Instacart, Stripe, UiPath, Zoom, the list goes on. As for Ravi, prior to Sequoia, he spent 4 years as COO & CFO @ Instacart playing an integral role in their hyper-growth journey. Before that Ravi spent 10 years as a Director @ KKR. In Today’s Episode You Will Learn: 1.) How Ravi made his way from KKR to being one of the key execs leading Instacart? How Instacart led to Ravi becoming a Partner @ Sequoia? 2.) When thinking about team, what does Ravi believe is the single most important question to ask? How does Ravi determine between good and great when assessing talent? What are the leading indicators? What have been Ravi's lessons on what it takes to acquire those great talents? 3.) How does Ravi think about and approach prioritisation today? How does Ravi analyse what to delegate vs what to control? Should you get good at your weaknesses and double down on strengths? How does Ravi think about vulnerability within leadership? How did he show that vulnerability as a leader at Instacart? 4.) In joining Sequoia, what has Ravi been most impressed with in regards to the team? What has he been most surprised by? Why is Ravi so bullish unanimous decision-making is right? How do founders determine which Sequoia Partner will be on their board? 5.) How does Ravi think about what it takes to be the very best board member? Who is the best board member Ravi has worked with? What made them so special? What advice does Ravi give to new board members adopting board seats for the first time? Items Mentioned In Today’s Show: Ravi’s Fave Book: Clay Christensen: How Will You Measure Your Life? As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Alex Tew is the Co-Founder and Co-CEO @ Calm, the #1 App for Meditation and Sleep allowing you to find your calm, sleep more, stress less and live better. To date, the company has raised over $143M in funding from some of the best including Lightspeed, Insight, TPG and then some very cool names such as Ashton Kutcher, Harry Styles, Brad Feld and Jason Calacanis. Prior to Calm Alex founded numerous other startups including PopJam, Pixelotto and most famously rose to internet fame with his founding of The Million Dollar Homepage. In Today’s Episode You Will Learn: 1.) How Alex went from playing Fifa with Michael Acton Smith in Berwick St, London to founding one of the hottest startups in the valley, Calm? 2.) What does Alex believe the very best brands do today? How do they message? How do they present? How do they divide opinion? How did Alex think about the early Calm brand? How has it changed? How does Alex advise others looking to build a company brand? 3.) Does Alex agree with Peter Fenton, "there is a lack of free and open distribution"? How does Alex analyse the economics for customer acquisition costs today? What is a good paid vs organic ratio? How do CACS change over time in Alex's experience? 4.) What have been Alex's biggest learnings on what it takes to build a viral product? Where do many people go wrong? Why does Alex believe pressure is the enemy of creativity? Does Alex believe people should create time for creative thought? What does Alex do to stimulate idea creation? 5.) How has Alex seen himself evolve and develop as a leader over the last 5 years? What have been the hardest elements to scale? How does Alex think about effective delegation? What have been Alex's biggest lessons on what it takes to hire A* people consistently? Items Mentioned In Today’s Show: Alex’s Fave Book: Godel, Escher, Bach: An Eternal Golden Braid As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Angela Strange is a general partner at Andreessen Horowitz, one of the leading venture firms of the last decade with a portfolio including the likes of Facebook, Github, Slack, Airbnb, Asana and more. As for Angela, she largely focuses on investments in financial services and is currently a board member of Addi, SynapseFi, and Tally. Prior to a16z, Angela was a product manager at Google where she launched and grew Chrome for Android and Chrome for iOS into two of Google's most successful mobile products. In Today’s Episode You Will Learn: 1.) How Angela made her way into the world of venture and came to be one of the leading fintech VCs with Andreesen Horowitz? 2.) Why does Angela believe that every company is going to be a fintech company? What is driving this shift? How does removing the barriers to entry for more products change both product quality and cost? How does Angela think about the role of regulation here? 3.) How does Angela think about what makes the best insertion points? How big does the initial wedge into the market have to be? When do you need to be able to prove you can transition from the insertion to the wider market? How does Angela fundamentally assess market size today? 4.) How does one transition to being the system of record? Do you have to be the system of record from day 1? Which examples are most striking for Angela on becoming a system of record? What are the biggest challenges in making this transition? Which metric tells you if you have become it? 5.) Does Angela think we are in a period of bundling or unbundling? What are the leading indicators of each? How does Angela assess the Fintech M&A market today? Will we continue to see large consolidatory moves in the form of Credit Karma, Plaid etc etc? Items Mentioned In Today’s Show: Angela’s Fave Book: Investing: The Last Liberal Art As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Alyson Friedensohn is the Founder & CEO @ Modern Health, a one-stop solution for employee mental well-being through evidence-based support and digital content. To date, Alyson has raised over $45M in funding from some of the best in the business including Kleiner Perkins, Founders Fund, John Doerr, 01 Advisors and Katrina Lake to name a few. Prior to founding Modern Health, Alyson was a Product Partner for Operations at Collective Health and before that was an operations manager @ Keas (acquired by Welltok). CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) How Alyson made her way into the world of startups and came to change how we think about mental health with Modern Health? 2.) How does Alyson think about and assess her own psychology? How does Alyson deal with crisis modes? What works? What does not? What is the driver for Alyson to get her through the very toughest of times? How does Alyson approach her own attitude to risk? 3.) What is Alyson's biggest pieces of advice for non-technical founders? What are the biggest challenges Alyson has had to overcome as a non-technical founder? How did she do it? How did Alyson strategically invest in the sales process? What worked? What did not? How does Alyson think about the balance of hitting sales quota and mental health? 4.) With some of the best VCs in the world, how did Alyson approach the process of investor selection? What can VCs do to build that relationship of trust with their founders? How does multi-stage VCs investing impact whether the founder remains in a "sales process" for the next round? How does Alyson temper the weight of John Doerr's words? 5.) What have been Alyson's biggest lessons in making it work marrying another founder? What works? What is challenging? How do they as a couple think about switching off? How does Alyson advise Harry on his own love life?! Items Mentioned In Today’s Show: Alyson’s Fave Book: How to Win Friends and Influence People As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Kevin Hartz is Co-Founder & Partner @ A*, a newly listed special acquisition company which raised $200M to acquire and take public a tech startup. Kevin is also the Co-Founder, former CEO, and Chairman Eventbrite (NYSE: EB). Before Eventbrite, Kevin was the Co-Founder & former CEO of online money transfer service, Xoom (acquired by PayPal for $1.1B). Kevin is also one of the most successful early-stage investors in the business with a portfolio including the likes of Airbnb (Seed, Series A), Uber (Series B), Pinterest (Seed, Series A), Trulia (first check) and PayPal (Seed). Troy Steckenrider is Kevin's co-founder and Partner @ A*. Prior to A*, Troy was COO @ ZeroDown changing the landscape for homeownership with $136M in funding. Before ZeroDown, Troy spent 5 years at Opendoor as Director of Capital Markets. Before that hyper-growth experience at Opendoor, Troy enjoyed roles at both Bain Private Equity and McKinsey. In Today’s Episode You Will Learn: 1.) How Troy and Kevin came together to co-found A*? What is a SPAC? What are Kevin and Troy looking to achieve with the SPAC? 2.) What does Kevin believe are the primary drivers for the rise in SPAC's over the last few years? How will they change the structure of both the VC and startup industry? How will the SPAC landscape evolve over the next few years? What is the biggest challenge they face? 3.) Why does Kevin believe that the fee structure for SPACs is egregious? How would they like to change the incentive structure? How does the timeline for a SPAC transaction compare to that of an IPO? How does the fee structure compare when comparing SPACs to banks in IPOs? 4.) Why did Kevin and Troy choose $200M for the right size for their first SPAC? How does the size of the SPAC determine the type of company the SPAC will merge with? What are Kevin and Troy looking for in their partner company? 5.) What does the fundraising process look like for a SPAC? How do SPAC sponsors deal with the challenge that LPs call pull out if they do not like the proposed partner deal? When evaluating SPACs, what do investors look to invest because of? What makes A* special? Items Mentioned In Today’s Show: Troy’s Fave Book: Churchill: Walking with Destiny As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jennifer Tejada is the CEO @ PagerDuty, the company that provides a real-time operations platform ensuring less downtime for your digital services. Prior to their IPO in 2019 PagerDuty raised funding from some of the best in the business including Accel, a16z, Baseline, Bessemer and Harrison Metal to name a few. As for Jennifer, prior to PagerDuty, she was CEO of Keynote Systems leading to their acquisition by Dynatrace. Before Keynote, Jennifer was Executive Vice President and Chief Strategy Officer at Mincom, leading them to their acquisition by ABB. If that was not enough, Jennifer is also on the The Estée Lauder Companies Inc. (NYSE: EL). CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) How Jennifer made her way into the world of SaaS and came to be one of the leading enterprise CEOs today with PagerDuty? How does Jen advise graduates on joining a startup vs large incumbent? 2.) How does Jen analyse and evaluate her relationship to risk? What does Jen do to remove herself from her environment and make the clearest decisions? How has Jen's decision-making process changed? How does Jen encourage debate and free thought sharing internally? 3.) How does Jen think about the role of insecurity within leadership? What would Jen say are her biggest insecurities? How does Jen manage them and mitigate them today? What works? What does not? Why does Jen believe data is the key to overcoming insecurities? 4.) What have been Jen's biggest lessons on what successful board management looks like? What separates good vs great board members? How can CEO's structure their board in an optimal way? What do they need? What do they not need? How does scale change this? 5.) How does Jen think her style of leadership has changed over the years? What have been Jen's lessons on what it takes to both acquire and retain the very best execs? Where do many go wrong here? Items Mentioned In Today’s Show: Jennifer’s Fave Book: Tuesdays With Morrie: An old man, a young man, and life's greatest lesson As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Sahil Lavingia is the Founder and CEO @ Gumroad, the company that helps creators do more of what they love. With Gumroad, Sahil has raised funding from an all-star list of investors including Accel, Kleiner Perkins, First Round and then Max Levchin, Chris Sacca, Ron Conway and Naval Ravikant on the individual side. However, most recently Sahil has made waves launching one of the first rolling funds on AngelList with his being $6M per year. In the past, Sahil has backed the likes of Lambda School, Figma, HelloSign and Haus to name a few. In Today’s Episode You Will Learn: 1.) How did Sahil make his way into the world of startups and angel investing? What were his biggest takeaways from being employee #2 at Pinterest? How did that experience impact his mindset? 2.) Why did Sahil decide to make his new fund an AngelList rolling fund? How is it structured? Does Sahil think this will represent a seismic shift in early stage investing? Is this a game of the 1%? Why does Sahil think early-stage remains so undervalued? How will this impact Series A pricing? 3.) How does Sahil assess his own price sensitivity today? How does Sahil think about the right way to turn down a founder? Where do many go wrong? How does Sahil feel about the rise of pre-empted rounds? How does Sahil advise seed founders with offers from multi-stage firms? 4.) What does Sahil believe founders care most about today in their investors base? How does Sahil think about investor brand and distribution? How does Sahil analyse the pros and cons of party rounds? How does Sahil advise founders on constructing their early cap table? 5.) How does Sahil think about his relationship to risk and to money? How did Sahil deal with it when his investors wrote off his company? How did Sahil feel about the weight of expectation placed on his shoulders at such a young age? How did he deal with this? Items Mentioned In Today’s Show: Sahil’s Fave Book: How to Win Friends and Influence People As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ben Rubin is the Founder & CEO @ /talk, the anti-meeting tool for fast, decentralised conversations. Prior to co-founding /talk, Ben was the Co-Founder & CEO @ Houseparty, where he scaled the product to millions of users and raised over $70M in funding from the likes of Sequoia, Greylock and Entree Capital to name a few. In addition over the last few years Ben has enjoyed roles at Sequoia as a Scout and then also at Benchmark as an Entrepreneur-In-Residence. In Today’s Episode You Will Learn: 1.) How Ben made his way into the world of startups and came to found Life on Air, later turning into Meerkat and Houseparty? 2.) What were Ben's key learnings from the Houseparty scaling experience? Why are the traditional metrics we use to measure startup success (DAU, MAU etc) insufficient? What is the nuance to metrics? How does Ben think about being first to market vs being the best to market? 3.) How does Ben believe the product principles differ when comparing the 0-1 stage vs 10-100 stage? How does Ben think about where to be rigorous on product? How does Ben advise founders to discover the key guiding product principle? What was it for Ben with Meerkat? 4.) Meerkat pivoted to Houseparty 3 months after having raised $40M, how did Ben communicate that to the board? How did they respond? How does Ben believe the best boards operate? What does Ben most look for in his board members? Where do many go wrong with board management? 5.) From the team side, when in hypergrowth, when do things start to break? What profiles are usually the first to break? Does that mean one should not hire those profiles? What can the leader do to create that intimacy and trust amongst the team? Items Mentioned In Today’s Show: Ben’s Fave Book: Seneca: The Shortness of Life As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Apurva Mehta is the Managing Partner @ Summit Peak Investments, investing in early stage venture capital funds and making direct co-investments. To date they have backed the likes of Raymond Tonsing, Lachy Groom and Josh Buckley to name a few on the fund side and then on the direct side, invested in Airtable, Virta Health and Sourcegraph. Prior to founding Summit Peak, Apurva spent 7 years as the Deputy Chief Investment Officer at Cook's Children's Hospital and before that spent 3 years as Director of Portfolio Investments at The Juilliard School. In Today’s Episode You Will Learn: 1.) How did Apurva make his way into the world of fund investing? How did that lead to his founding Summit Peak and also becoming a GP? 2.) How does Apurva think about how much importance to place on references when diligencing managers? What reference types mean a lot? Which mean less? Why does Apurva still believe early-stage is the most inefficient segment of the venture landscape? 3.) How does Apurva think about GP commits? Is it fair to have a required benchmark? How does Apurva advise founders on LP concentration limits? When is one LP too much of a fund? How does Apurva advise managers on selling a stake in the management company? 4.) As a fund of funds, how does Apurva approach fund portfolio construction today? How does this differ between the fund portfolio vs the direct portfolio? How does Apurva think about the compression of fundraising timelines both with GPs and Founders? Why does Apurva believe founders at the early-stage care less about firm brand today? 5.) How does Apurva feel about investing in managers he has not met in person? How does the GP/LP fundraising process need to change? How does COVID change the fundraising process for venture funds? How will LPs react to these changes? Items Mentioned In Today’s Show: Apurva’s Fave Book: Principles: Life and Work by Ray Dalio Apurva's Most Recent Investment: Sourcegraph As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Anna Khan is a General Partner @ CRV, one of the pre-eminent firms of Silicon Valley stretching over what is now an incredible 18 funds. In their portfolio, they have the likes of Airtable, Doordash, Postman and PillPack to name a few. As for Anna, prior to joining CRV, she spent an incredible 6 years at Bessemer investing in the likes of Intercom, NewVoiceMedia, RainforestQA and Zylo. If that was not enough, Anna is also the Founder & CEO @ Launch X Ventures, offering female entrepreneurs an immersive opportunity to learn how to raise capital for their businesses. In Today’s Episode You Will Learn: 1.) How Anna made her way into venture as an analyst with Bessemer and how that led to her scaling the venture ladder to now being GP @ CRV? 2.) How does Anna feel about the importance of analysts in venture? Should founders spend meaningful time with analysts? How should they determine which to spend time with? What were the biggest lessons Anna learned about venture and people from being an analyst at Bessemer? 3.) With the rise of rounds being pre-empted, how does Anna determine when to lean in and move on a deal vs when to wait? How does Anna determine when to stretch vs be disciplined on valuation? Why does Anna believe very few firms are "doing real early-stage investing" today? 4.) Why does Anna believe that there are so much fewer women in venture? How does Anna respond to the suggestion that it is a "pipeline problem"? How would Anna advise an all-white male partnership looking to truly change how they work? How does carry come into showing commitment? 5.) What advice does Anna give to people on developing your early network? Why does Anna believe VCs spending time with VCs is antithetical? How has Anna's investment decision-making process changed over the last 9 years? How does Bessemer's compare to CRV's? Items Mentioned In Today’s Show: Anna’s Fave Book: Why We Sleep: The New Science of Sleep and Dreams As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Dev Ittycheria is the President and CEO @ MongoDB, recognized as the world's most popular next-generation database and the first database company to go public in over 26 years. Prior to their IPO, MongoDB raised from some of the best in the business including Sequoia, USV and NEA to name a few. As for Dev, before Mongo Dev was Managing Director at OpenView Venture Partners, Venture Partner at Greylock Partners, and CEO/Co-founder of BladeLogic, which was acquired by BMC for $900 million. Dev has also sat on some incredible boards including AppDynamics, athenahealth and BazaarVoice. In Today’s Episode You Will Learn: 1.) How Dev made his way into the world of startups? How Dev made his entry into the world of venture? How that led to his joining Mongo as CEO? 2.) How has Dev seen his style of leadership change over the last few years? What are the 3 core benefits of being vulnerable with your investors? Why does Dev believe you sometimes have to be inefficient to be effective? What element/trait would Dev like to improve and develop as a leader? 3.) Where does Dev believe the majority of leaders make mistakes when it comes to scaling their teams and orgs? How does Dev think about the debate of whether to promote internally or hire externally for a role? Why does Dev believe the asymmetry of information there is dangerous? 4.) What has been Dev's biggest lessons when it comes to the speed that information is relayed within orgs? How does this differ between good news and bad news? What can leaders do to create environments where bad news is shared freely? Where do many go wrong here? 5.) How does Dev advise founders on the criteria they should use to determine which investors to work with? What has been so impressive to Dev about working with Sequoia? How would Dev describe Roelof Botha's style of board membership? How can investors crucially build trust with their CEOs? Items Mentioned In Today’s Show: Dev’s Fave Book: High Output Management As always you can follow Harry and The Twenty Minute VC on Twitter here!

Joe Thomas is the Founder & CEO @ Loom, the startup that helps you get your message across by making it easy to record instantly shareable videos. To date, Joe has raised over $68M from some of the valley's leading firms including Sequoia, Kleiner and Coatue as well as individuals such as Mathilde @ Front, Kevin & Mike @ Instagram and Dylan Field @ Figma to name a few. Prior to founding Loom, Joe was in LA as Director of Product at MyLife.com and before that Director of Operations at MediaPass. Due to Loom's success, Joe has been named to Forbes 30 Under 30 for Enterprise Tech. In Today’s Episode You Will Learn: 1.) How Joe made his way from the mid-West to the valley and came to found one of the hottest startups today in Loom? 2.) What does Joe believe are 3 rules to operate remote teams successfully? Why does Joe believe in remote + HQ as a model so much? How do the tools and culture need to change with this as a new format for work? How do leaders now need to learn to write more than ever before? 3.) How has fundraising fundamentally change in the world of COVID? What are the benefits? What can founders do and tools can they use to increase their chances of getting funded in a COVID world? What did Coatue do to build rapport and trust without meeting in person? 4.) What advice would Joe give to founders on how to pick their early VCs? How does Joe advise founders when it comes to accepting multi-stage money at seed? Why does Joe believe you need to be upfront with your VCs about their ability to build future ownership? 5.) Sequoia and Coatue led the Series B, how did the round go down many months before Joe and Loom planned to raise it? What did Sequoia do to win and close the deal? How did that as a founder make Joe feel? How does Joe advise VCs on what it takes to win the most competitive of deals? Items Mentioned In Today’s Show: Joe’s Fave Book: Enders Game, Think On These Things As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Steve Jurvetson is the Co-Founder @ Future Ventures who announced their debut and flagship $200M Fund in 2019. Steve's incredible portfolio includes the likes of SpaceX, Tesla, Planet, Memphis Meats, Hotmail, and the deep learning companies Mythic and Nervana. Steve also sits on the board of both SpaceX and Tesla. Prior to founding Future, Steve was the co-founder of renowned valley firm Draper Fisher Jurvetson where he led investments in 5 companies that went public in successful IPOs and several others that became billion-dollar acquisitions. In Today’s Episode You Will Learn: 1.) How Steve made his way into the world of startups and Silicon Valley and how that led to his creation of “The Lean Startup Movement”? 2.) How does Steve think about and assess market timing? How does Steve assess technical risk? Given the long term horizons of such deep tech projects, does Steve think we need to change the 10 + 2-year fund life structure? How would Steve like to see funds structured? 3.) Given the sheer size of outcomes if these plays work, how does Steve assess his own price sensitivity? How does Steve approach the challenge there is a lack of downstream investors for such deep tech projects? How does Steve try and catch an industry on the cusp of a transition? 4.) How does Steve assess his own relationship to money? How has it changed over the years? Why does Steve fundamentally believe that venture partnerships do not scale? Where do venture partnerships breakdown? How can one introduce cognitive diversity into a firm? 5.) Having worked with Elon Musk across both SpaceX and Tesla, what does Steve believe makes Elon one of the most gifted entrepreneurs of our time? What is Steve's most memorable moment from his many years of friendship with Elon? What have been his biggest takeaways from SpaceX and Tesla? Items Mentioned In Today’s Show: Steve’s Fave Book: Out Of Control: The New Biology of Machines, Social Systems, and the Economic World Steve's Most Recent Investment: Prellis Biologic As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Clay Wilkes is the Founder & CEO @ Galileo, the API standard for card issuing and digital banking, powering many of the leading global FinTech companies including Chime, TransferWise and Monzo to name a few. Prior to their reported $1.2Bn acquisition by SoFi, Clay raised just $86M in funding with Galileo from the likes of Accel and Ryan Smith @ Qualtrics, having run the company as a profitable company before that for over 15 years. Clay also has a keen interest in philanthropy having created the Galileo foundation with his wife in 2005. In Today’s Episode You Will Learn: 1.) How Clay made his way into the world of tech and startups more than 20 years ago and how he came to build the foundations for many fintechs today with Galileo? 2.) When looking at the current financial ecosystem does Clay believe we are in a phase of bundling or unbundling? Does Clay believe we will see the verticalisation of banking? Will every company become a payments company? Does Clay believe we will see consolidation in the space? 3.) What does Clay believe were the benefits of going 15 years withour raising VC money, building a profitable business? What are the trade offs? What could he have done if he had raised? With hindsight, does Clay wish he had raised earlier? Why was then the right time to raise? 4.) Why does Clay believe the discovery mechanism for VCs finding startups is broken? How did Clay select the venture firm he chose to work with, Accel? What advice does Clay give to board members when it comes to being the best board member to their founders? 5.) Why did Clay believe that selling to SoFi was the right decision? What are the benefits of the merger? How does Clay think about the competitive element that many of Galileo's current clients are competitors with SoFi? How do they remedy and solve for that today? Items Mentioned In Today’s Show: Clay’s Fave Book: Why Nations Fail: The Origins of Power, Prosperity and Poverty As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Brad Feld is a Co-Founder and Managing Director @ Foundry Group, one of the most successful venture firms of the last decade with a portfolio including the likes of Zynga, Fitbit and Sendgrid to name a few. Brad is also a co-founder @ Techstars and prior to Foundry, he co-founded Mobius Venture Capital.  Tracy Lawrence spent the last 8 years as Founder & CEO @ Chewse, the startup that it effortless for office managers to order delicious food for their teams.  Tracy grew the team to 300 people across 4 markets, raised millions in venture capital, and ultimately sold the business to Foodee. Jerry Colonna is the CEO of Reboot.io where he is now the professional coach to some of the world's leading founders. Prior to his work with Reboot, Jerry was an early-stage VC co-founding Flatiron alongside Fred Wilson in 1996. In Today’s Episode You Will Learn: 1.) How did Brad, Jerry and Tracy all experience their first forms of depression? At what stage did it become a more prominent part of their life? Why do they think then was the catalyst? 2.) Why does Jerry believe that despite what people say, no one is crushing it? How can founders present their vulnerability as a strength? At what point did Tracy realise this? How did she convey her vulnerability to her team? Who is to blame for the lack of vulnerability and fear of opening up? 3.) How does Brad think about tying happiness to milestones? What are the biggest dangers of doing so? Does this mean one does not have goals? How does one balance between ambition and appreciating the present? How did Brad learn this when Amy asked for a divorce? How did he respond? 4.) Why does Brad believe fear, guilt and anxiety are useless emotions? What was the result of Tracy tying her mental state to her revenue line? How does Tracy think about the loneliness of being a founder? What does Brad believe is some of the biggest BS in the industry? As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Steve Blank is one of the leading luminaries of Silicon Valley, credited with being foundational to the creation of The Lean Startup movement and having spent the last 9 years at Stanford University as a professor and the last 8 as a Senior Fellow @ Columbia University. Steve is the author of "The Four Steps To The Epiphany" and "The Startup Owner's Manual". Prior to joining the world of academics and writing Steve spent over 20 years in the world of entrepreneurship as part of, or co-founded eight Silicon Valley startups ranging from semiconductors, video games, personal computers, and supercomputers. If that was not enough, Steve is also on the Defense Business Board for the United States Department of Defence. In Today’s Episode You Will Learn: 1.) How Steve made his way into the world of startups and Silicon Valley and how that led to his creation of "The Lean Startup Movement"? 2.) Why does Steve vehemently disagree with Adam's Smith's "Invisible Hand" theory when it comes to government intervention? Why is this proven to have failed? How does this only help the rich become richer? As a result, what needs to change in the mechanics of the economy? 3.) Why does Steve not believe that there is accountability placed on investors and founders for projects they create and invest in? Why does Steve believe for the majority of investors today, they have no social conscience? How could this be changed and improved? 4.) How did seeing the booms and busts of the dot com and 2008 impact Steve's operating mentality? What are the 3 core traits that will ensure success for founders in a post COVID world? How should founders change their decision-making process post-COVID? Why does Steve believe in "benign dictatorship"? Items Mentioned In Today’s Show: Steve’s Fave Book: Innovator's Dilemma: When New Technologies Cause Great Firms to Fail As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Chamath Palihapitiya is Founder & CEO @ Social Capital, the organisation on a mission to transform society by using technology to solve the world’s hardest problems. Social's portfolio includes the likes of Slack, Yammer, Front, Intercom and Carta to name a few. As for Chamath, prior to founding Social, he spent an incredible 4 years at Facebook including as the original exec in charge of FB Platform as well as being responsible for overseeing core growth components and overseeing FB's mobile efforts. If that was not enough, Chamath is also an owner @ The Golden State Warriors & Chairman @ Virgin Galactic. In Today’s Episode You Will Learn: 1.) How Chamath made his way into the world of tech and startups, came to be a VC with Mayfield before joining Facebook and then starting Social? 2.) What were Chamath's biggest takeaways from his team building the growth team at Facebook? Why does Chamath believe that forecasts are worthless? What should founders focus on instead? What did Facebook teach Chamath about defensibility and moat building? 3.) What was the realisation moment for Chamath that the venture firm he was building with Social was not what he wanted to build? Why does Chamath believe the biggest mistakes he made were "compensation and partner selection"? How would he do them differently now? What does he look for most in partners today? How does he detect for integrity? 4.) Why has Chamath doubled down on the SPAC model? What are the core benefits both to the founders and investors? What are the core challenges with both direct listings and IPOs? How does Chamath think about scaling his SPAC strategy? What are the core challenges in doing so? 5.) Facing alcoholism and psychological challenges with his parents, how did Chamath deal with becoming a carer sooner than expected? How has becoming a parent changed Chamath's operating mentality today? How does Chamath analyse his relationship to money today? Items Mentioned In Today’s Show: Chamath’s Fave Book: Liar's Poker: From the author of the Big Short As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Alex Mather is the Founder & CEO @ The Athletic, the startup bringing you in-depth sports stories you won't hear anywhere else. To date, Alex has raised over $139M with The Athletic from some of the best in the business including Founders Fund, Bedrock, Y Combinator and Emerson Collective to name a few. Before founding The Athletic, Alex spent an incredible 5 years as part of the hyper-growth @ Strava serving Vice President of Product Management and Product Design. In Today’s Episode You Will Learn: 1.) How Alex made his way into the world of tech and startups with Strava? How did his time at Strava lead to his founding The Athletic? 2.) With the scaling of The Athletic to over 500 people, how has Alex seen his leadership style change and adapt? What does he need to improve? How did having children impact how he thinks about management? What lessons did he take from Strava on what worked for community building? 3.) What was it like raising money for a subscription media business back in 2016? Who was the first person to really take a bet on Alex and The Athletic? What value adds does Alex think are the most important for VCs to provide? What are the biggest investor misconceptions around media? 4.) How does Alex see the future structure of the media landscape? What elements of media is Alex most concerned about right now? Does Alex view Substack as competition? What does Alex believe will be the 2 ways to succeed in media moving forward? 5.) What have been the biggest customer acquisition learnings for Alex from The Athletic? How does Alex feel about platform reliance for customer acquisition with Facebook? What does it take to successfully acquire customers on Facebook at scale? Items Mentioned In Today’s Show: Alex’s Fave Book: The Kingdom of God is Within You As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.    

Joe Lonsdale is a General Partner @ 8VC and in the past has invested in many notable companies including Wish, Oculus, Oscar and Guardant Health. As a result, in both 2016 and 2017, Joe was the youngest member of the Forbes 100 Midas List. Prior to 8VC, Joe co-founded Palantir, one of the world's most impactful multi-billion dollar software companies. Joe also co-founded and serves as Chairman @ Addepar, which has over $1.8 trillion managed on its wealth management technology platform. If that was not enough, Joe is also a founder of Affinity, Anduin and Esper. In Today’s Episode You Will Learn: 1.) How Joe made his way into the world of tech and startups, came to co-found Palantir and Addepar and how that led to his founding 8VC? How does Joe believe the study of history makes one a better investor? 2.) Why does Joe believe that the best VCs are company builders? How does Joe think about, evaluate and put into action the incubator model? How does Joe respond to LPs that suggest it is a distraction? How does voting for incubations differ for investment voting? 3.) What does contrarian thinking really mean to Joe? What does Joe do to specifically engender contrarian thinking in the 8VC partnership? What is the relationship between contrarianism and political correctness? How does Joe think about the dangers of woke culture today? 4.) How does Joe advise founders to think through cash burn and runway today? What is going to happen to companies that sacrified growth for gross margin in 1 year? How does Joe advise founders on the balance of sticking to your vision and mission vs knowing when to give up? 5.) Why does Joe think it is important to not just start new companies but new cities also? Despite the insane cost of living, why does Joe believe the Valley has given rise to the insane levels of innovation it has done? Will the dominance of the valley remain over the next decade? Items Mentioned In Today’s Show: Joe’s Fave Book: How Innovation Works, A Time to Build: From Family and Community to Congress and the Campus Joe’s Most Recent Investment: Beacon As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Julia DeWahl is one of the rising stars of the Silicon Valley angel investor community with a portfolio including the likes of Linear (Sequoia-backed), Modern Fertility (USV backed) and Primer (Founders Fund backed). Prior to angel investing Julia was one of the first 10 employees at Opendoor seeing their hyper-growth first hand in many different roles from Head of Seller Experience to being General Manager of Pheonix & City Operations. Before Opendoor, Julia spent 3 years as a consultant at Bain. If that was not enough, Julia is also an avid cyclist and is setting up a women's cycling apparel line alongside her investing. In Today’s Episode You Will Learn: 1.) How Julia made her way into the world of startups with Opendoor from Bain and how that position at Opendoor led to her angel investing? What were the 1-2 takeaways for Julia from her time at Opendoor that have most impacted how she angel invests today? 2.) Customer Discovery: When is the right time to engage in deep customer discovery work? How does one select the customers to go deep with? How does Julia structure the process? What questions are most revealing? Where do many go wrong? How does one determine the feedback to accept vs which to reject? 3.) How does Julia think about implementing systems for growth? What is the structure of these systems? Where does one start? How does Julia determine the metrics to track and focus on? How does Julia balance between growth vs profitability? 4.) Does Julia believe people can really scale with the company? What are the leading indicators that people are struggling to scale with the company? How does Julia advise generalists to survive and thrive in a scaling organisation? Should they specialise? 5.) What have been some of Julia biggest lessons of what it takes to be successful as an angel today? Who has Julia learned and gained the most from in this new discipline? How does Julia measure her own success as an angel? What are the core challenges? Items Mentioned In Today’s Show: Julia’s Fave Book: The Courage To Be Disliked: How to free yourself, change your life and achieve real happiness Julia’s Most Recent Investment: Primer: Homeschool with superpowers As always you can follow Harry and The Twenty Minute VC on Twitter here!

Oren Zeev is the Founding Partner @ Zeev Ventures, one of the best and most under the radar firms in the early stage Silicon Valley landscape. Over the past decade, Oren has backed the likes of TripActions, Tipalti, Audible, Houzz, Chegg and Hippo Insurance to name a few. Prior to crushing it with Zeev Ventures, Oren spent 12 years as a General Partner @ Apax Ventures, starting in Israel and then moving to the US where he headed the Technology Practice of Apax and the Silicon Valley office. In Today’s Episode You Will Learn: 1.) How Oren made his way into the world of venture with Apax and how that led to his founding his own firm, Zeev Ventures? 2.) Having been in a venture partnership, why did Oren want to be a solo GP? What are the benefits? How does it change decision-making? What are the downsides? How does Oren discuss deals and ideas without partners? How does Oren explain the decision to LPs on being a solo GP? 3.) Why does Oren not believe in thesis-driven investing? What are the dangers and downsides to it? Why do most managers still do it then? Why does Oren specifically look for under-appreciated markets? How is pricing and competition different there? How does Oren assess his own price sensitivity? 4.) Why does Oren think that diversification is overrated? How does Oren think about cross-fund investing? Why is it such a strength that managers should use? Why do many not do it? How does Oren think about reserve allocation? Why is he the only VC to not have a reserves strategy? 5.) How does Oren think about fund deployment timelines? Why do LPs not like the annual fundraising approach? How does Oren size up his position in companies over time and round? How does Oren feel about founders taking secondaries? Items Mentioned In Today’s Show: Oren’s Fave Book: The Last Lion: Winston Spencer Churchill: Defender of the Realm Oren’s Most Recent Investment: Treeverse As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Lo Toney is the Founding Managing Partner @ Plexo Capital, a very unique firm making both direct investments and fund investments. They have invested in Precursor, Boldstart, Female Founders Fund and WorkBench on the fund side and then PlayVS, Replicated and StyleSeat on the direct side. Prior to Plexo, Lo was a Partner @ GV (Google Ventures) and before that was a Partner with Comcast Ventures where he led the Catalyst Fund. Before venture Lo was an operator enjoying exec roles at Zynga, Nike and eBay. In Today’s Episode You Will Learn: 1.) How Lo made his way into the world of venture with GV and how that led to his innovating on the venture model investing in both funds and directly with Plexo today? What were Lo's biggest takeaways from his 5 years as a Partner @ GV? 2.) How will GPs raising today be impacted by COVID? How does this differ dependent on the stage they invest and the size of fund they are raising? How does Lo advise managers communicating with existing and new potential LPs today? 3.) What does Lo mean when he discusses your "minimum viable fund size"? How does Lo advise GPs when it comes to closing strategies? How much do they need for first close? How many closes should there be thereafter? Should they take the money when it is on the table? 4.) How does Lo feel about anchor LPs taking/investing in the GP? What are the benefits for the manager of doing so? Why does Lo believe there is such a binary view towards it? Why does Lo disagree with the benchmarks set of what a GP commit "should be"? 5.) Why does Lo believe we will see the hybridization of GP/LP over the coming years? What are the benefits of having your LP also direct invest? What are the core challenges to the model? How does Lo envisage the world of venture evolving over the next decade? Items Mentioned In Today’s Show: Lo’s Fave Book: Why Should White Guys Have All the Fun?: How Reginald Lewis Created a Billion-Dollar Business Lo's Most Recent Investment: PlayVS As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.      

Andrew Wilkinson is the Managing Partner @ Tiny, a vehicle that buys, builds and invests in wonderful internet companies. Within their family of companies is Dribble; home to the world's best design professionals; MetaLab and Supercast to name a few. Tiny does also make venture investments in the likes of Superhuman, SpaceX, Pitch and Buffer. Today Andrew oversees a group of companies with over 300 employees and tens of millions in revenue. In Today’s Episode You Will Learn: 1.) How Andrew made his way from founding a design agency in Canada to starting Tiny and building a family of companies with over 300 people? 2.) What does Andrew mean when he says, when buying companies he looks for companies like New Zealand? What qualities/features do they have? How does Andrew think about price sensitivity when acquiring these companies? What determines paying a premium price to Andrew? 3.) How does Andrew assess and analyse true defensibility within company strategies today? Why does Andrew not believe they will lose any companies? How does Andrew think about grow vs profitability? Are they mutually exclusive? When does one pour fuel on the fire and raise big? 4.) How has Andrew seen himself develop and change as a leader over the last 5 years? What does truly great delegation look like? What is Andrew's biggest weakness? What is his biggest insecurity? How does Andrew think about sink the boat vs non-sink the boat decisions? 5.) Does Andrew believe we will see the unbundling of social networks moving forward? What are the core characteristics that determine whether a social network will win? Why does Dribble have defensibility as a brand against all large incumbents? Items Mentioned In Today’s Show: Andrew’s Fave Book: Tao of Charlie Munger: A Compilation of Quotes from Berkshire Hathaway's Vice Chairman As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

David Sacks is the Co-Founder @ Craft Ventures, one of Silicon Valley's leading early-stage funds with David's portfolio including the likes of Facebook, Tesla, SpaceX, Palantir, Affirm, Airbnb, Slack and Bird to name a few. David started his career in tech as the first product leader and COO @ Paypal, growing payment volume from $0-$500M per month, leading to their $1.5Bn acquisition by eBay. David then founded Geni.com, creating a family tree for the whole world, the company was acquired 3 years later by MyHeritage. David then founded Yammer, the secure solution for internal corporate communication and collaboration, acquired by Microsoft for $1.2Bn. Finally, David then became COO and Interim CEO @ Zenefits before starting Craft. In Today’s Episode You Will Learn: 1.) How David made his way from founding Yammer to creating one of the valley's newest and most prestigious firms in Craft Ventures? Given David's operating success he could have angel invested continuously, why decide to start a fund? What does he ultimately want to achieve with Craft? 2.) How did experiencing the Dot Com Bubble with Paypal and then 2008 impact David's investing and operating mindset? Does David believe VCs really are "open for business" today? How is VC behaviour shifting when comparing early to later stage? How is Craft responding? 3.) Unit Economics: How does David assess unit economics in early-stage opportunities he is looking to invest in? What does proper attribution look like? Where do many go wrong with unit economics? Is it too early to try and assess unit econ at seed? How does David think about having mental plasticity towards unit economics, recognising how they change over time? 4.) Customer Acquisition: Does David agree with Peter Fenton, "there is a complete lack of free and open distribution"? What are the rules of thumb on CAC that David does and then does not agree with? How does David feel about blended CAC? What separates good from great when it comes to CAC/LTV? 5.) Churn: How does assess net negative churn in the businesses he works with? What is great, good, decent and poor? How does avid think about logo vs dollar retention? How does David advise founders who feel COVID has not impacted churn for them? What should they expect? 6.) Burn + Capital Efficiency: How does David analyse burn and capital efficiency today? What does he mean when he discusses "the burn multiple"? How should the burn multiple change with the stage of the business? How does David advise founders on how aggressively to cut burn today? Items Mentioned In Today’s Show: David's Fave Book: Thucydides’ Trap David's Most Recently Announced Investment: Sourcegraph As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Chris Best is the Founder & CEO @ Substack, the company that makes it simple for a writer to start a paid newsletter. To date, Chris has raised over $17M in funding from the likes of a16z, Y Combinator, Twitch CEO Emmett Shear and Zynga Co-Founder Justin Waldron to name a few. Prior to founding Substack, Chris was the Co-Founder & CTO @ Kik, letting users connect with friends, groups and the world around them. The company raised over $220M in funding from Spark, Tencent and USV to name a few. In Today’s Episode You Will Learn: 1.) How Chris made his way into the world of startups and came to found Kik? How his journey with Kik led to his founding Substack? 2.) During COVID, traditional media publications have been hit hard and Substack has taken off, how does Chris see the correlation there? Given the public journal of record has always been free, how does Substack interact with public news? What does Chris 3.) Why does Chris believe that micropayments are a fundamentally bad idea? Structurally why would they not work? Does Chris agree the biggest problem consumers face today in content is one of discovery? Why not? 4.) When designing the Substack product today, how does Chris think about incentive design? Why does Chris believe with incentives, Substack is the opposite of Twitter from a product perspective? Why have the "economics of attention now been flipped?" 5.) How has Chris seen himself evolve and change as a leader over the last 3 years? What advice would Chris give to CTOs making the move into the role of CEO? What does Chris believe his greatest strengths and weaknesses are as a leader? How does Chris find the war for talent today? Items Mentioned In Today’s Show: Chris’ Fave Book: The Death and Life of Great American Cities As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.    

Merci Victoria Grace is a Partner @ Lightspeed Venture Partners, one of the valley's leading venture firms of the last decade with a portfolio including the likes of Snapchat, Mulesoft, Affirm, AppDynamics and more. As for Merci, prior to entering the world of venture, Merci spent 3 years at Slack including as Head of Growth where she grew the growth team to over 50 people and drove DAU's from 500K to 5M in under 2 years. Merci is also the Founder of Women In Product a global community of incredible women in product management. CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) How Merci made her way into the world of venture having led the growth team at Slack for close to 3 years? 2.) Merci has been working to productise venture, so what core elements of venture need productising? What systems and tools has Merci put in place to create a product around these processes and methods? What have been the biggest challenge in the attempt to productise VC? 3.) How does the decision-making process look like at Lightspeed? How does Merci use post mortems to help her improve post having lost a deal? How does she structure those post-mortems? What have been some of the core takeaways? What internal tech stack does LSVP run itself on? 4.) How does Merci see the future of the collaboration tools market? Are we entering a period of bundling or unbundling? How does Merci feel about the debate between synchronous and asynchronous? How does Merci determine between those who have grown sustainably vs unsustainably in the time of COVID? 5.) Why do the majority of collaboration tool startups fail? What do they get so wrong in their go-to-market? For those that succeed, what are the commonalities in those that succeed? Why is being good at Twitter a competitive advantage? How does Merci feel about the Superhuman, high touch onboarding style? Items Mentioned In Today’s Show: Merci’s Fave Book: Never Split The Difference: Negotiate As If Your Life Depended on It As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Daniel Erickson is the Founder & CEO @ Viable Fit, the startup that allows you to find product-market fit faster than ever by collecting structured user feedback to measure PMF on an ongoing basis. Daniel has raised funding from the likes of David Sacks @ Craft Ventures, Todd Goldberg and Superhuman Founder, Rahul Vohra and then also Brianne Kimmel @ Worklife Ventures. Prior to founding Viable Fit, Daniel was VP Engineering @ Eaze and before that spent time as CTO @ Getable and then also had a front-row seat for the hyper-growth of Yammer with a 3-year stint there. In Today’s Episode You Will Learn: 1.) How Daniel made his way into the valley and startups from setting up a consultancy in Portland and how that led to founding Viable Fit? 2.) How does Daniel define product-market fit today? Why does Daniel believe it is the single most important metric for startups? What happens if you do not have product-market fit? How does Daniel feel about investors spending so much time analysing unit economics at seed? 3.) What is the single most important question one can ask to determine whether you have PMF? How does customer segmentation play a role in revealing the true PMF number? How do you productise this and put it in a process? What does Daniel make of the rise of closed betas? 4.) Once they have the customer data, what elements of the data should founders double down on to determine PMF? How do they determine between feedback to adopt vs discard? Why does Daniel believe PMF is transient and you always have to measure it? Items Mentioned In Today’s Show: Daniel’s Fave Book: Atomic Habits by James Clear As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.    

Ryan Petersen is the Founder & CEO @ Flexport, the operating system for global trade with over $1.3Bn in funding from the likes of Softbank, Founders Fund, DST, GV and First Round to name a few. Justin Kan is the Founder @ Atrium and Twitch (acq by Amazon for $1Bn). Justin is also a prolific angel with a portfolio including the likes of Scale AI, Digits, Cruise and Triplebyte to name a few. Matteo Franceschetti is the Founder & CEO @ Eight Sleep, the #1 Smart Mattress, designed to help you fall asleep faster and stay asleep. To date, Matteo has raised over $70M from Founders Fund, Khosla Ventures, Craft Ventures, Kevin Hartz and Ryan Petersen to name a few. Steve Schlafman is a Coach and Investor @ High Output. Previously Steve was a Partner @ Primary Ventures in NYC and before that Principal @ RRE. CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) What was your realisation moment for stopping drinking? How did it come about? What was your prior relationship to alcohol like? 2.) For me I always found an excuse to not stop drinking, when you think about your attempts to give up, what excuses did you provide as reasons for continuing to drink? What insecurities and vulnerabilities did drinking hide and mask for you? How did it impact them? 3.) From a literal standpoint, how did you approach giving up the act of drinking? What tools did you find most helpful? What resources do you recommend? How has your life changed since you stopped drinking? Matteo, you have the data from Eight Sleep, what does the data say about how stopping drinking truly impacts your sleep? 4.) People often say that stopping drinking kills your social life, what would you respond to that commonly held belief? What other core misconceptions do you find people hold towards drinking? To those considering giving up drinking, what would you advise them? What do you know now about alcohol that you wish you had known earlier? As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Avi Meir is the Founder & CEO @ TravelPerk, the travel management platform that combines the best of leisure and corporate travel into one smooth experience. To date, Avi has raised over $134m with TravelPerk from the likes of DST, Spark Capital, Felix Capital and Heartcore to name a few. Prior to founding TravelPerk, Avi co-founded HotelNinjas, a hotel management product that was acquired by Booking.com. Before that Avi was VP Product at budgetplaces where he managed a team of 50 across product and marketing. In Today’s Episode You Will Learn: 1.) How Avi made his way into the world of startups and came to change the way we think of corporate travel with TravelPerk? 2.) Why has Avi advocated for the re-opening of society much sooner than others have done? If Avi were in government, what would he advocate for and do? How does Avi try and effectively assess the core risks of COVID both from a societal and economic perspective? 3.) How does Avi feel when he hears the comparison of COVID to Saars or 9/11 when it comes to their impact on travel? Why is this so different? Why does Avi believe 2021 will be a bigger year for business travel than 2019? 4.) How does Avi advise founders heavily impacted by COVID to really effectively analyse their spend and optimise runway? How does Avi think approach the element that sales and marketing is now non-revenue driving? How does Avi approach resource allocation as a result? 5.) Does Avi believe we will see a fundamental re-shaping of corporate travel? What will change? How does domestic travel change? What will the landscape look like on the other side? Who will survive? Who will thrive? Does Avi feel now is an opportune time for M&A? Items Mentioned In Today’s Show: Avi’s Fave Book: The Hundred-Year-Old Man Who Climbed Out of the Window and Disappeared As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Elad Gil is one of Silicon Valley's most successful and prominent angels of the last decade with a portfolio including the likes of Stripe, Square, Airbnb, Pinterest, Instacart, Flexport and Brex to name a few. Prior to solely company investing, Elad was an operator as Founder and CEO @ Color Genomics for their first 3 years. Before Color, Elad was a VP of Corporate Strategy @ Twitter following their acquisition of the company he founded, Mixer Labs. Before founding Mixer, Elad spent 3 years at Google where he was involved with 3 acquisition including the Android acquisition. In Today’s Episode You Will Learn: 1.) How Elad made his way into the world of startups and how that led to his investing in some of the most prominent companies of the last decade? 2.) How is the venture and startup landscape shifting right now? What does Elad make of the large multi-stage funds re-entering seed? How does Elad advise founders when it comes to taking secondaries? 3.) What are the core elements startups need to assess to fully understand their cash position? What is the optimal runway to have and to raise for today? How can founders stress test their runway models? Where does Elad see the most mistakes when it comes to runway? 4.) Does Elad believe the VC messages of "Open for Business" during COVID? How does Elad advise founders when it comes to valuation sensitivity today? What are the core terms that founders should watch out for when raising? How does Elad see venture fund reserve allocations changing? 5.) What are the core tenets of an effective layoff strategy? How should they determine the right level of aggression with which to make cuts? How can layoffs be done in a way that maintains internal culture and morale? Where does Elad see many going wrong when it comes to layoffs? 6.) Which business will thrive in COVID times? Which will die? What are the leading indicators of each? How does Elad determine in the businesses that are growing immensely during COVID, those that are sustainable growth and those which are purely due to COVID? Items Mentioned In Today’s Show: Elad’s Fave Book: Master of the Senate: The Years of Lyndon Johnson Elad’s Most Recent Investment: Deel As always you can follow Harry, The Twenty Minute VC and Elad and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ariel Cohen is the Founder & CEO @ TripActions, the company trusted by more than 4,000 companies to manage their business travel and expenses. To date, Ariel has raised more than $980M with TripActions from the likes of Lightspeed, Oren Zeev and a16z to name a few. Prior to TripActions, Ariel co-founded StreamOnce, a business multimedia integration platform which was acquired by Jive Software. Prior to StreamOnce, Ariel led Product Management in a senior leadership role at Hewlett-Packard. In Today’s Episode You Will Learn: 1.) How Ariel made his way into the world of tech and came to change the way we think about business travel today with TripActions? 2.) What are TripActions doing in their business to be there for their partners, customers and suppliers in the long term? TripActions engaged in layoffs, how did Ariel approach the size of layoff required? What is the right way to do layoffs? How does this change in a remote world? 3.) Given the uncertainty, how does Ariel advise founders to assess and correct their burn and spending? What is a reasonable amount of runway to reserve for? For those hit hard on the demand side, what can they do to build durable defensibility when they can't scale demand? 4.) How does Ariel view the future of business travel? Does Zoom replace much of the business trips? What will the landscape look like in 3 years? What players will survive? Who will thrive? 5.) From a founder psychology perspective, what has Avi done to cope in these very challenging times? What has worked? What has not worked? What does Ariel advise founders struggling to cope psychologically? What can investors do to be there for their founders? Items Mentioned In Today’s Show: Ariel’s Fave Book: Mr Vertigo As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.    

Hamilton Helmer is the Managing Partner & Chief Investment Officer @ Strategy Capital a long-only public equity fund that selects securities for investment based on Power Dynamics, a proprietary model of fundamental value, developed by Hamilton over decades of strategy consulting with clients such as Hewlett-Packard, Adobe and more. Hamilton is also the author of one of my favourite books, 7 Powers. If that was not enough, Hamilton is also an Instructor in the Economics Department @ Stanford University. In Today’s Episode You Will Learn: 1.) How Hamilton made his way into the world of investing from advising some of the largest tech titans on the planet with Adobe and HP? 2.) What is a strategy mental model? What makes the most effective strategic models? What characteristics do they have? How should founders balance between sticking to models and being willing to change them? What are Hamilton's biggest takeaways from working with Netflix? 3.) "All strategy begins with invention", what did Hamilton mean by this? How does Hamilton explain the success of copycats in markets? How does Hamilton separate between first mover and creator? How does Hamilton analyse the transition from startup to pricer with scale economics? 4.) How does Hamilton advise founders to view and approach competition? Why does Hamilton totally disagree with the requirement of being 10x better than your competition? Is product innovation alone enough without brand or business model innovation? 5.) How does Hamilton define "brand"? Is brand an attainable strategy alone or is it the byproduct of something else? How transferable is brand in one category to alternative categories? How does a brand truly know when they have sustainable leverage and power? Items Mentioned In Today’s Show: Hamilton’s Fave Book: The Road to Reality: A Complete Guide to the Laws of the Universe, Stardust As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Sarah Kunst is the Founder and Managing Director @ Cleo Capital with a portfolio including the likes of StyleSeat, Glow Bar and PlateJoy to name a few. Prior to venture, Sarah served as a senior advisor at Bumble where she focused on their corporate VC arm, Bumble Fund, and on the board of the Michigan State University Foundation endowment. If that was not enough, Sarah is also a contributing editor @ Vanity Fair. Due to her success, Sarah has been named a Future Innovator by Vanity Fair and a top woman in VC by Wall St Journal. In Today’s Episode You Will Learn: 1.) How Sarah made her way into the world of venture from Bumble and how that led to her founding Cleo Capital? 2.) Does Sarah believe VCs really are still "open for business"? What does Sarah make of all the dry powder sitting on the sidelines? How does Sarah think reserve allocation strategies will change today? Why does Sarah believe another great vintage of funds is to come, as it did in 08'? 3.) What would Sarah most like to change about the world of venture? Does Sarah agree that GP commit expectations prevent diversity in venture? How was the fundraising process for Sarah? How can VCs prove skin in the game without having personal capital? 4.) What is the #1 piece of advice Sarah is giving her founders in these COVID times? How does Sarah advise her founders on approaching the talent market today? How does Sarah advise her founders on burn and capital allocation given COVID? Items Mentioned In Today’s Show: Sarah’s Fave Book: Attached: Are you Anxious, Avoidant or Secure? How the science of adult attachment can help you find – and keep Sarah’s Most Recent Investment: Planet Forward As always you can follow Harry, The Twenty Minute VC and Sarah and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Mike Maples is a Founder & Partner @ Floodgate, one of the leading early-stage firms of the last decade with investments in the likes of Lyft, Twitch, Twitter, Okta and Sonos to name a few. He has been on the Forbes Midas List since 2010 and was also named one of “8 Rising Stars” by FORTUNE Magazine. Before becoming a full-time investor, Mike was involved as a founder and operating executive at back-to-back startup IPOs, including Tivoli Systems (IPO TIVS, acquired by IBM) and Motive (IPO MOTV, acquired by Alcatel-Lucent.) In Today’s Episode You Will Learn: 1.) How Mike made his way from founding startups to entering the world of venture and the gap he saw in the market when founding Floodgate? 2.) Mike has previously said, "a startup is not a company, it is a series of breakthroughs". How does Mike define a breakthrough? What are the 2 most meaningful breakthroughs a startup can experience? Which excites Mike the most to see? How do the best startups scale pre-breakthrough to post-breakthrough? 3.) What are the core ways inflections can create breakthrough opportunities? What were Mike's learnings on inflections from investing in Lyft? What does Mike mean when he talks about the importance of "backcasting"? What did investing in Twitch teach Mike about forecasting? 4.) How does Mike feel about the rise of operator and angel funds? How does Mike analyse the re-entrance of large multi-stage funds back into seed markets? Does Mike agree with Semil Shah, "founders are voting with their feet and taking multi-stage money at seed"? 5.) As Mike's peers have all moved into larger funds, Mike did not, why? How does Mike view "fund size as your strategy"? How does Mike think about the centrality of ownership? Does Mike really believe you can concentrate capital into your winners? What are the challenges? Why does Mike feel self-promotion is one of the biggest challenges in VC? Items Mentioned In Today’s Show: Mike’s Fave Book: Superforecasting: The Art and Science of Prediction Mike’s Most Recent Investment: CommonStock As always you can follow Harry, The Twenty Minute VC and Mike and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Conor White-Sullivan is the Founder & CEO @ Roam Research, the tool taking over our industry providing a seamless note-taking tool for networked thought. Prior to founding Roam, Conor founded 2 prior businesses and also worked at HuffPost as a Co-Founder of HuffPost Labs where he reported directly to Arianna Huffington and HuffPost CTO. In Today’s Episode You Will Learn: 1.) How Conor's high school wrestling career taught him "how to win"? What was the founding story with Roam? How does Conor think about when to stay true to the vision and persist vs when to give up? 2.) How does Conor think about the product design philosophy they have @ Roam? Conor has said before, "Roam is not about taking better notes", what is Roam about then? How does Conor think about the importance of adding challenge to a product? What does he mean when he discusses the importance of "low floors and high ceilings" with regards to product design? 3.) How would Conor analyse his own hiring and team-building philosophy? Why are the two most important traits, "girt and autodidacts"?How does Conor really stress these two characteristics in an interview process? Why does Conor choose to live with the team? What are the benefits of this? 4.) Does Conor believe we are in a phase of bundling or unbundling when it comes to collaboration tools? Does Conor believe we will see large players acquire and consolidate over the coming months? Why does Conor compare Roam more to Google than other collaboration tools? 5.) How does Conor think about go-to-market today? What were some of Conor's biggest takeaways for bootstrapping for years with revenue from customers? Why is Conor borrowing from the Tesla GTM? What does that really mean in practice? Items Mentioned In Today’s Show: Conor’s Fave Book: How to Read a Book: The Classic Guide to Intelligent Reading As always you can follow Harry, The Twenty Minute VC and Conor and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Mark Cuban is a serial entrepreneur, investor, and owner of the Dallas Mavericks. His career began with his founding of MicroSolutions, a company he went on to sell to CompuServe in 1990. Then in 1995 Mark co-founded Broadcast.com - streaming audio over the internet. In just four short years, Broadcast.com (then Audionet) was sold to Yahoo for $5.6 billion dollars. Following the acquisition in 2000, Mark acquired the Dallas Mavericks where since his taking over they have competed in the NBA Finals for the first time in franchise history in 2006 - and becoming NBA World Champions in 2011. They are currently listed as one of Forbes' most valuable franchises in sports. If that was not enough, Mark is also one of ABC's "Sharks" on the hit show Shark Tank. In Today’s Episode You Will Learn: 1.) How Mark made his way into the world of technology and startups having been fired from his first job in sales? 2.) How does Mark evaluate his relationship to wealth and money? How has that changed over time? What advice does Mark have to those that tie happiness and money together? 3.) What does Mark think about Silicon Valley investors today? Why does he believe they and the valley are like Hollywood? Why does Mark believe that if the greatest tech companies of today had been started elsewhere, they would be more successful? 4.) How does Mark evaluate his own investing philosophy today? How does Mark think about price and price sensitivity? Why is Mark so keen to have his investment funded from the cashflow of the business? Does this not narrow opportunity and limit upside? How does Mark evaluate risk today? 5.) Why does Mark believe post-COVID is the single greatest time to be an entrepreneur? What advice would he give to an entrepreneur starting their new business in this time? How would Mark go about the re-opening of society post lockdown? Items Mentioned In Today’s Show: Mark’s Fave Book: Rebooting AI: Building Artificial Intelligence We Can Trust, Healthy Buildings: How Indoor Spaces Drive Performance and Productivity As always you can follow Harry, The Twenty Minute VC and Mark and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Wayne Chang and Jeff Seibert are the co-founders @ Digits, the company that gives you a complete, real-time understanding of your expenses, all in just a few clicks. To date, Wayne and Jeff have raised over $32M for Digits from some of the best in the business including Peter Fenton @ Benchmark and Jess Verrilli @ GV and then with the most incredible base of angels with the founders from Box, Github, Stitch Fix, Tinder, Gusto and more. Prior to Digits, Wayne and Jeff co-founded Crashlytics, acquired by Twitter for a 9-figure sum in Jan 2013 and then acquired from Twitter by Google in 2017. If that was not enough they are also LPs in some of the world's most exclusive funds and angels in the likes of Gusto, OpenDoor and SoFi to name a few. In Today’s Episode You Will Learn: 1.) How did Jeff and Wayne make their way into the world of tech and startups? How did Wayne crashing a startup dinner start everything for them? 2.) How did Jeff and Wayne's prior success with Crashlytics impact their operating mindset scaling Digits today? What worked? What did not work? What gets easier with time? What gets harder the second time around? 3.) What have been Wayne and Jeff's biggest lessons from having a remote team from Day 1? What structure and framework do they use to hire the best remote talent? How does that change at the exec level? How do they think about optimising product management for remote teams? 4.) How would Wayne and Jeff summarise their design philosophy with Digits? Why does Wayne believe "minimalism only favours the designer"? When does it make sense to actually add some complexity to your product? 5.) Digits raised $33M pre-launch, why did they favour this approach? How do they think about when to transition from lean and iterative to aggressive and pouring fuel on the fire? Why did they choose to work with Peter Fenton? How do they think about optimising their angel network? Items Mentioned In Today’s Show: Wayne’s Fave Book: Enders Game Jeff's Fave Book: Creative Selection: Inside Apple's Design Process During the Golden Age of Steve Jobs As always you can follow Harry and The Twenty Minute VC on Twitter here!

Howie Liu is the Founder & CEO @ Airtable, the all in one collaboration platform that has taken so much of our ecosystem by storm. To date, Howie has raised over $170M from some of the best in the business including Benchmark, Thrive, Coatue, Caffeinated Capital, Founder Collective, CRV and Freestyle to name a few. Prior to founding Airtable, Howie was the Co-Founder @ Etacts, an automated intelligent CRM that was acquired by Salesforce just 9 months after creation. Howie then led the social CRM product at Salesforce. Fun fact, Howie started his career as an intern at Freestyle Ventures. In Today’s Episode You Will Learn: 1.) How Howie made his way from founding Etacts to changing the way we think about databases and spreadsheets today with Airtable? How did Salesforce acquiring Etacts impact Howie's operating mentality with Airtable? 2.) With the rise of remote work, what have been Howie's core observations from the last month of the world going WFH? What does it take to succeed? What mistakes have Airtable made in their process of work from home? Why did it not work? What lessons did Howie take from that? 3.) How does Howie think about Airtable's transition from an application to a platform? What does he perceive as the core challenges in making the transition? What lessons has he learned from studying others who have done it? Why did Howie choose Peter Fenton @ Benchmark to work with? 4.) How has Howie seen himself evolve and scale as a leader over the last few years? What have been the most challenging elements? How does Howie think about which individuals he would like as mentors? How does he determine which advice to ingest vs to reject? 5.) How does Howie analyse the remote work/collaboration tools environment today? Does Howie believe we will enter a period of consolidation with the proliferation of new tools created? Does Howie believe we will see an unbundling in collaboration tools? Items Mentioned In Today’s Show: Howie’s Fave Book: Hard Drive: Bill Gates and the Making of the Microsoft Empire, Spying on Whales As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Rahul Vohra is the Founder & CEO @ Superhuman, the startup that has rebuilt the inbox from the ground up creating the fastest email experience ever made. To date, Rahul has raised over $56m with Superhuman from some of the best in the business including a16z, First Round, Box Group and then 2 of my favourites in Jeff Morris Jr @ Chapter One and Ed and Elliot @ Boldstart. Prior to founding Superhuman, Rahul was the Founder @ Rapportive, a company later acquired by LinkedIn in 2014. If that was not enough, Rahul is also an investor having co-founded a new firm with Todd Goldberg just last year. In Today’s Episode You Will Learn: 1.) How Rahul made his way from making the first plugin for Gmail with Rapportive to changing how we think about email today with Superhuman? 2.) Why does Rahul believe game design is worth doing? What is the difference between game design and gamification? What does it take to create a game? What is the truth on game design? 3.) What are the core 5 factors that make up effective game design? How can products incorporate goals to make the user feel emotion when engaging? What emotions does one want the user to feel? How can they be tested? What controls should be placed around the UX? Why are controls so fundamental? 4.) What is the difference between a toy and a game? How can one effectively incorporate toys into their product? How has Superhuman done this effectively to date? Hw can designers create a system of flow in the user experience? What works? What does not work? 5.) Did Rahul intentionally create an entirely new category when it comes to onboarding? Why does Rahul pushback on people that suggest 1-1 onboarding is not scalable? What does the unit economics look like? How does this scale to $100M ARR? Items Mentioned In Today’s Show: Rahul’s Fave Book: The Art of Game Design: A book of lenses As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

Mark Suster is the Managing Partner @ Upfront Ventures, one of LA's leading and largest venture firms with a portfolio including the likes of Bird, GOAT, Maker Studios and Ring.com to name a few. Prior to joining the world of venture, Mark was the founder & CEO of two successful enterprise software companies, the most recent of which was sold to Salesforce.com where Mark became VP, Products. Mark is also the author of one of my favourite industry blogs, Both Sides of The Table. In Today’s Episode You Will Learn: 1.) How Mark made his way from founding enterprise companies to joining "the dark side" of venture with his move to Upfront? 2.) How does the current economic landscape change the world of B2B? How will renewals be impacted? How will customers approach discounting? Similarly, how will the world of B2C be impacted by COVID? How does this impact marketing and ad spend? 3.) How does Mark think about reserve allocation today with Upfront? How does that change in the face of COVID? Why does Mark believe this environment will redefine valuations? How should founders respond in the face of heavily changed valuations? 4.) Does Mark believe we will see a graveyard of new venture firms who have deployed too quickly and have too many hungry mouths to feed? How does Mark think about building temporal diversification into the portfolio? How can managers use reserves more intelligently moving forward? 5.) Does Mark agree with the Twittersphere that VCs remain "open for business"? How will we see deal volume impact? How will we see size of transaction impacted? What is the most important role a VC can play today? How will the M&A market also be impacte din the face of COVID? Items Mentioned In Today’s Show: Mark’s Fave Book: Disunited Nations: The Scramble for Power in an Ungoverned World Mark's Most Recent Investment: Solve As always you can follow Harry, The Twenty Minute VC and Mark and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Sarah Cannon is a Partner @ Index Ventures, one of the world’s leading venture funds with a portfolio including the likes of Dropbox, Skype, Figma, Bird, Slack and many more incredible companies. As for Sarah, at Index, she works with groundbreaking companies including Notion, Slack, Pitch, Quill and Instabase. Prior to Index Sarah spent time at CapitalG, Warburg Pincus and even worked in The White House as Policy Advisor for the National Economic Council. Akshay Kothari is the COO @ Notion, the company that has taken the modern working world by storm as the all-in-one workspace to write, plan, collaborate and get organised. Just last week Notion raised a $50M round led by Index at a reported $2Bn valuation. Prior to Notion, Akshay spent 5 years at LinkedIn following his prior company, Pulse News, being acquired by LinkedIn in 2013. In Today’s Episode You Will Learn: 1.) How did Sarah make her way into the world of venture from The White House and come to be a Partner @ Index today? How did Akshay parlay his angel investment into Notion into joining as COO the company 5 years later? 2.) With such a proliferation of collaboration tools today, how does Sarah see the remote work/collaboration tools landscape playing out? Are wein a phase of bundling or unbundling? Will we enter a phase of heavy consolidation? How does Notion think about the transition from an application to a platform? What are the challenges in doing so? 3.) What have been some of Akshay's core observations and learnings from watching the world move to remote work overnight? What behaviours will remain post COVID? What behaviours will not? What sectors will be forever changed due to the crisis? What opportunities does that bring about? 4.) Why did Notion decide to keep the team so small for so long? What are the advantages? How does Notion think about maintaining quality when hiring for scale now? What have been some of Akshay's biggest learnings in what it takes to attract A* talent to Notion? 5.) Why did Notion choose the route of profitability over the more conventional early path of the VC treadmill? How does one's mindset change when suddenly raising a large round of new financing? What becomes possible? What guard rails still need to be set? Items Mentioned In Today’s Show: Akshay’s Fave Book: Order without Design: How Markets Shape Cities Sarah's Fave Book: Guns, Germs and Steel: A short history of everybody for the last 13,000 years As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.  

David “DHH” Heinemeier Hansson (@dhh) is the creator of Ruby on Rails, founder and CTO at Basecamp (formerly 37Signals), and the best-selling co-author of Rework and Remote: Office Not Required. If that was not enough, fun fact, he went from not having a driver’s license at 25 to winning, at 34, the 24 Hours of Le Mans race, one of the most prestigious automobile races in the world. It is often called the “Grand Prix of endurance and efficiency.” In Today’s Episode You Will Learn: 1.) How David made his way into the world of tech and startups from his childhood living in Copenhagen and how a cold email led to the founding of Basecamp with Jason Fried? 2.) What have been some of David’s core observations as people move to remote work over the last few weeks? What is the #1 mistake that 90% of teams make? How does David advise founders to approach loneliness and depression in their team? What strategies have Basecamp used to unite the team and inspire collaboration and teamwork? 3.) Why have David and Jason always tried to keep the Basecamp team as small as possible? Why does David believe one of the biggest problems is that execs have too much time? How does that manifest itself? What does David’s week look like? How does he approach meetings? 4.) Why does David hate the majority of “mission statements” today? What are the best composed of? What are the worst? What feelings does David believe your mission statement should inspire in the reader? What does David believe one needs to do to build a challenger brand today? 5.) Why has David and Basecamp always resisted the conventional path of raising VC funds? Why does David believe needs VC money is total BS? Why does David believe it is BS to chase being a unicorn? Why have founders got this so wrong today and what can they do to change? 6.) How would David describe his relationship to money? How has that relationship changed over time? What are the core challenges as one moves from a monetary to a deeper appreciation of what makes one happy? How did the transition occur for David? How does David advise others in terms of finding their moment for the transition? Items Mentioned In Today’s Show: David’s Fave Book: Erich Fromm: To Have Or To Be As always you can follow Harry, The Twenty Minute VC and David and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

Blake Scholl is the Founder & CEO @ Boom Supersonic, the world's fastest commercial aeroplane, aspiring to bring back supersonic passenger flight at an affordable price. To date, Blake has raised over $166M in funding with Boom from the likes of Paul Graham, Sam Altman, Ray Tonsing @ Caffeinated Capital, Homebrew and 8VC to name a few who have featured on the show in the past. Prior to changing the world of commercial flight, Blake started his career with a 5-year stint at Amazon as a Manager of Social Networks and Automated Advertising. Blake then went on to found his own company, Kima Labs, acquired by Groupon in 2012 where he then spent 2 further years before founding Boom. In Today’s Episode You Will Learn: 1.) How Blake made the move from Groupon to changing the way we think about commercial travel today with Boom Supersonic? 2.) How was the fundraising process for Blake given he was raising for supersonic jets? What is his most memorable fundraising moment? Where does Balek believe investors provide outsized value? Where could the investing class improve? How should the fund structures today change? 3.) What deliberate choices and decisions has Blake made to find and acquire the best talent? What is Blake's favourite interview question? What works? What does not work? What specific elements has Blake built into the culture at Boom to build operational excellence? 4.) How has Blake seen himself evolve and develop as a leader over the last few years? What have been the most challenging elements to develop and scale? How does Blake feel on whether founders should have experience on the industry they are entering or if there are benefits of not having so? 5.) What would Blake really like to change about the world of tech and Silicon Valley today? How does Blake feel about the current level of both innovation and founder ambitions? What can be further done to foster this in the coming years? Items Mentioned In Today’s Show: Blake’s Fave Book: Atlas Shrugged As always you can follow Harry, The Twenty Minute VC and Blake and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.    

Fred Destin is a Founding Partner @ Stride.VC, one of Europe's newest and largest early-stage seed firms. Prior to co-founding Stride, Fred was a General Partner @ Accel where he was the lead investor and board member at Deliveroo, Pillpack (acq. AMZN for $1BN) and Carwow. Prior to Accel, he was a partner at Atlas Venture (now Accomplice) where he invested in and served on the board of Pillpack, Zoopla (IPO), Secret Escapes, Integral Ad Science (partial exit to Vista at $850M) and TheCurrencyCloud to name a few. Fun fact, his portfolio has a total enterprise value of more than $10BN and he generated in excess of $700M in exit value to investors. In Today’s Episode You Will Learn: 1.) How did Fred make his way into the world of venture and come to co-found one of Europe's newest and largest seed funds in Stride.VC? 2.) If you look to Twitter, all VCs are "open for business", does Fred really believe the market is still open for business? How will deal volume be affected? How bad does Fred think this could get? How does this downturn compare to that of the dot-com and 2008? 3.) Why did Stride decide to take the decision to pause on investing at this moment in time? How does Fred respond to the suggestion of better pricing and less competition at this time? How does Fred believe venture investors view of risk evolves at this time? What is the first to change? 4.) With many new funds deploying their first fund in 18 months, does Fred think we will see a gravyard of new fund managers out of cash and with cash hungry portfolios? What advice does Fred give to newer managers of other elements they have to be minfdul/aware of? 5.) How does Fred think about the right way for managers to communicate with their LPs at this time? What has Stride done that has worked? Does Fred believe we will see many LPs defaulting on their initial commitments? How does Fred think emerging managers can navigate this? Items Mentioned In Today’s Show: Fred’s Fave Movie: Mulholland Drive Fred’s Most Recent Investment: Collective Benefits As always you can follow Harry, Fred and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ravi Viswanathan is the Founder and Managing Partner @ NewView Capital, launched in 2018 with their $1.35Bn Fund I, they have already set themselves as leaders in the world of growth funding with 3 massive exits in less than 2 years in the form of Plaid, sold to Visa for $5.3Bn, Acquia, sold to Vista Equity for $1Bn and then Scout, sold to WorkDay for $540M. Prior to founding NewView Ravis spent 14 years at one of the largest venture firms in the business, NEA where he co-led their venture growth equity practice and in 2016, became COO @ Nea. Before the world of venture, Ravi spent 4 years as a VP @ Goldman Sachs and before that was at McKinsey & Co. In Today’s Episode You Will Learn: 1.) How Ravi made his way into the world of venture from investment banking and how that led to his founding the monster $1.35Bn Fund I for NewView Capital? 2.) Given the first fund being $1.35Bn, how did Ravi find the fundraising process for NewView? On reflection, what did he and the team do well that they would do again? What did they not do well that they would alter? What advice would Ravi give to first-time fund managers raising today? 3.) Would Ravi agree with Bill Gurley, "the biggest challenge today is the sheer quantum of capital flowing into the industry"? What does Ravi make of the rise of private equity (PE) houses entering the venture landscape? How does it change the exit landscape? 4.) How does Ravi think about the right way for funds to navigate and approach the secondary market? What advice would he give to emerging managers? How does Ravi feel about founder secondaries? What framework does he use to determine whether the amount is reasonable? 5.) How does Ravi think about what it take to truly win the best deals in competition today? If one does not have the budget of a16z, how does one build a venture platform? Where do the majority of investors make mistakes when it comes to VC value add? Items Mentioned In Today’s Show: Ravi's Fave Book: Shoe Dog: A Memoir by the Creator of NIKE, Born A Crime: Stories from a South African Childhood Ravi’s Most Recent Investment: Plaid As always you can follow Harry, Ravi and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Businesses are always looking for ways to shorten their sales cycles. HelloSign provides secure, effortless eSignatures proven to speed up contract signing by 80%. Most clients go from a multi-week turnaround to a multi-hour one. They’re an industry leader and have been voted #1 for Ease of Use two years in a row on G2 Crowd. Don’t let pen and paper processes slow you down. Click Here to join the millions of users already using HelloSign to close more deals faster!

Jean-Charles Samulian is the Co-Founder & CEO @ Alan, the startup revolutionising health insurance with a service centred on people, simplicity and comfort. To date, Jean-Charles has raised over $85M in funding with Alan from some of the best in the business including Jan Hammer @ Index, Shakil Khan, Tom Stafford @ DST, Xavier Niel and Brent Hoberman to name a few. Prior to changing the healthcare insurance system, Jean-Charles founded Expliseat, revolutionising airline seating for economy class, now used by some of the world's leading airlines. In Today’s Episode You Will Learn: 1.) How Jean-Charles made his way from re-inventing the airline seating industry to re-inventing the way consumers experience healthcare insurance? How did re-inventing the airline seat prepare and impact Jean-Charles' mindset going into the highly regulated healthcare market with Alan? 2.) How does JC structure his investor updates? What framework does JC believe these investor updates should take? Does he include thank you's at the end? Does he include requests for help? How does he involve the team in the writing of these updates? How does JC insert core strategic thinking into his updates? How much time does JC allocate to writing updates? How does JC think about transparency when coming investor updates? 3.) How has JC created a culture of distributed ownership combined with radical transparency? What are the key elements to achieve this? Where do so many go wrong with culture maintenance and creation? What have been the biggest challenges in scaling from 20 to 190 people in just 2 years? What has worked? What has not worked? 4.) How does JC structure the hiring process at Alan? Why does JC believe in the importance of "shadowing" for people to be excellent at hiring? How does JC define "excellence" in a potential candidate? What questions does JC most like to ask candidates? How does JC think about the right way to optimise new employee onboarding? Where do many go wrong with onboarding? What have been their core lessons at Alan as to what it takes to make it great? 5.) How does JC think about extreme self-organization today? How does JC structure his day and his time? How would JC summarise his relationship to his phone? What does he actively do to reduce his dependence on his phone? What has worked and what has not worked with regards to increasing productivity? How does JC advise others looking to make their first steps in increasing their productivity? Items Mentioned In Today’s Show: Jean-Charles’s Fave Book: The Everything Store: Jeff Bezos and the Age of Amazon As always you can follow Harry, The Twenty Minute VC and Jean-Charles and on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

Howard Marks is the Co-Founder and Co-Chairman of Oaktree Capital Management, a leading investment firm with more than $120 billion in assets. Prior to founding Oaktree, Howard spent 10 years at The TCW Group, where he was responsible for investments in distressed debt, high yield bonds, and convertible securities. Previously, Howard was with Citicorp for 16 years, where he served as Vice President and senior portfolio manager in charge of convertible and high yield securities. Howard has also written two books, most recently Mastering the Market Cycle: Getting the Odds on Your Side, and it was Warren Buffet who said, “When I see memos from Howard Marks in my mail, they’re the first thing I open and read. I always learn something.” In Today’s Episode You Will Learn: 1.) How Howard first made his way into the world of finance over 50 years ago? How did not getting an investment banking job change the course of Howard’s life? 2.) What does Howard believe is the fundamental economic crisis occurring today? How does Howard expect liquidity availability to change over the next few years? What analogies of prior downturns and recessions can we look to learn from? How does this downturn differ and align to prior recessions and downturns? What policies would Howard like to see governments enact to prevent the worst-case scenario? 3.) In conditions of such uncertainty, how does Howard think about how to manage and move forward with such volatility? What are Howard's frameworks and mechanisms to analyse crises events like this? Taking the analysis one level further, how bad does Howard believe this could get? If short of The Great Depression, are there scenarios that could lead there? What are the leading signals? 4.) Being proactive, how does today's situation change the mentality and activity at Oaktree? Why does Howard not agree with the notion of "the falling knife"? How does Howard think about market bottoms? How does Howard determine the right insertion point? Why does Howard believe the best investors are unemotional? How can one manage the psychology of catching a falling knife that falls further? 5.) What advice would Howard give to the may millions of working professionals today that have never seen a recession in their professional career? What makes Howard the most nervous when he looks at and assess the landscape today? What does Howard believe is the biggest misconception people believe with regards to the current economic crisis? Items Mentioned In Today’s Show: Howard’s Fave Book: Fooled by Randomness: The Hidden Role of Chance in Life and in the Markets As always you can follow Harry, The Twenty Minute VC and Howard on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Alyssa Ravasio is the Founder & CEO @ Hipcamp, the startup that allows you to book unique camping experiences on over 300,000 campsites, cabins, RV parks, public parks and more. To date, Alyssa has raised over $41M in funding from some of the best in the business including Benchmark, a16z, Brad Feld, Dave Morin, Sam Shank @ Hotel Tonight and more. Prior to founding Hipcamp, Alyssa enjoyed numerous diverse roles including being Director of Sales & Marketing @ Revel Systems to working on International Information and Communication Policy in the US State Department. In Today’s Episode You Will Learn: 1.) How Alyssa made her way from the US State Department to founding the game-changer of camping experiences in the form of Hipcamp? 2.) How did Alyssa solve the classic chicken and egg problem for marketplaces in the early days with Hipcamp? How important does Alyssa believe it is for marketplaces to have truly differentiated supply? How does Alyssa think about what it takes to prevent leakage in marketplaces today? How can marketplace founders be strategic in building moats around their business? What works? What does not work when building marketplace defensibility? 3.) How does Alyssa manage the psychology of being CEO? What does Alyssa find to be the most challenging element of the role? What have been Alyssa's biggest lessons from her last 12 months in the role? How has she seen her style of leadership change and develop over time? How does Alyssa deal with the shit hit the fan moments? 4.) How did Alyssa find the fundraising process for Hipcamp? Why did Alyssa wait 5 years before raising the Series A? What changed in the business that made Alyssa realise then was the right time to raise big? How did the Series B with a16z and Andrew Chen catalyse so fast? Why did Alyssa select the investors she did? What investors did Alyssa not select or not select her that she would also loved to have worked with? Items Mentioned In Today’s Show: Alyssa’s Fave Book: The Overstory: Shortlisted for the Man Booker Prize 2018, Uncanny Valley: A Memoir As always you can follow Harry, The Twenty Minute VC and Alyssa on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

Manu Kumar is the Founder @ K9 Ventures, one of the leading seed firms of the last decade with a portfolio including the likes of Carta, Lyft, Twilio, Auth0 and Lucidchart to name a few incredible companies. Prior to K9, Manu was either the founder or co-founder of 4 companies, 3 of which with successful exits and the 4th being the fantastic Carta. Manu also has an incredible model with K9 where he not only invests in companies but also founds them and is currently the founder and CEO @ HiHello, the company that allows you to network smarter providing digital business cards designed to help you curate and grow your network.  In Today’s Episode You Will Learn: 1.) How Manu made his way into the world of venture having founded 4 prior companies and how he came to found K9 and be one of the OG's of pre-seed funding, having coined the term? 2.) What does Manu believe have been the biggest and most significant changes in the early stage market over the last 7 years? How does Manu evaluate the rise of operator and scout funds? Would Manu agree with Semil Shah, "founders are voting with their feet and taking multi-stage money at seed?" What advice does Manu give to founders on taking multi-stage money at seed? How does Manu evaluate their aggressive movement back into the seed stage? Why is it? 3.) Given Manu only makes 3-4 new investments per year, how does Manu think about and assess his own portfolio construction today? How does Manu think about building temporal diversification into the portfolio? What does Manu believe is the biggest mistake early-stage managers make in the first few years? Why does Manu believe that "group think" is so dangerous for funds today? What can they do deliberately to avoid it? 4.) Manu not only invests but also founds companies at the same time, how does Manu split his time and what does his day look like? What are the benefits of investing and operating simultaneously? What are the biggest challenges and drawbacks? What elements did Manu believe as an investor before starting his new company, HiHello, that he has now changed his mind on, post founding the company? Items Mentioned In Today’s Show: Manu’s Fave Book: How to Win Friends and Influence People Manu’s Most Recent Investment: Workona: A Better Way To Work As always you can follow Harry, The Twenty Minute VC and Manu on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Misha Esipov is the Founder & CEO @ Nova Credit, the startup that allows you to use your international credit history to apply for credit cards, apartment rentals, loans and more. To date, Misha has raised over $69M with Nova from some of the best in the business Kleiner Perkins, Index, First Round, Pear and Core Innovation Capital to name a few. As for Misha, prior to changing the world of credit history, he spent over 5 years in the more traditional world of finance including time at Apollo in the world of private equity and then also Goldman Sachs in the world of investment banking. If that was not enough, due to the incredible impact Nova is having, Misha also sits on the board of World Education Services. In Today’s Episode You Will Learn: 1.) How Misha made his way from the world of investment banking and private equity with Goldman and Apollo to changing the way we think about international credit with the founding of Nova? 2.) How does Misah think about and asses both risk and value creation? How did Misha's time at Goldman Sachs influence his operating mentality and how he thinks about the value of data today? Why does Misha find the growth at all costs and revenue later mindset challenging? What core fundamentals around unit economics did Misha establish early with Nova? How does Misha advise founders when it comes to unit economics? 3.) Misha has raised over $69M from some of the best, how did Misha find the process of fundraising? Where specifically does Misha believe his investors provide outside value? What is the optimal way to use an investor in the recruitment process? Where does Misha believe investors could do better and improve? How does Misha advise founders when it comes to manager selection? 4.) How does Misha manage the psychology of being CEO? How does he deal with the shit hit the fan moments? How has his role changed over the last 3 years? What elements have been the most challenging to learn and scale? 5.) How does Misha advise founders on building a diverse pipeline of recruitment candidates from day 1? Why does Misha believe that no recruitment firm can solve for diversity? What is his process as a result for ensuring a truly diverse team? What works? What does not? How does Misha building a culture of accountability? How does Misha think about optimising internal decision-making? Items Mentioned In Today’s Show: Misha’s Fave Book: Mastery (The Robert Greene Collection) As always you can follow Harry, The Twenty Minute VC and Misha on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

Toni Schneider is a Partner @ True Ventures, one of the valley's leading early-stage firms with a portfolio including the likes of Peloton, Hashicorp, Fitbit, Automattic (Wordpress) and Tray.io to name a few. As for Toni, he has spent 14 years as a Partner @ True but during that tenure, he was also the CEO of Automattic for 8 years where he helped WordPress.com become a top 10 global internet destination with close to a billion monthly visitors. Before that, he was a VP @ Yahoo post their acquisition of the company he was CEO of Oddpost, much of their work formed the basis for Yahoo mail.  (Note: Recorded Pre-Coronavirus) In Today’s Episode You Will Learn: 1.) How Toni made his way into the world of venture following two turns in the seat of CEO and then joining Yahoo? 2.) Does Toni fundamentally believe it helps when investing to have been both an operator with Automattic and Partner @ True? How did being CEO @ Automattic shape how he thinks about investing today? How did Toni manage the balancing act of a being a CEO and Partner at a venture fund for 7 years? Having been a CEO and having worked with the best, what does Toni believe are the qualities that make the great CEO of today? 3.) Why does Toni believe that startups do not have to be as stressful as they are or are portrayed to be? How does Toni deal with the shit hit the fan moments? What can an investor do in times of high stress when the founder is not performing? What is the right way for them to express that the performance is not where it needs to be? On the flip side, what is the right way for investors to show their support to the founders? 4.) What are Toni's biggest learnings from the Wordpress days on what it takes to run a truly successful remote team? Where does Toni see many people going wrong today? What does Toni advise those considering going remote first? What does Toni believe are the biggest pros and cons of the model? What infrastructure does one need to have in place to make it seamless? Does it still make sense for companies to be in the valley? Items Mentioned In Today’s Show: Toni’s Fave Book: Their Eyes Were Watching God, Predictably Irrational: The Hidden Forces That Shape Our Decisions Toni’s Most Recent Investment: Piavita As always you can follow Harry, The Twenty Minute VC and Toni on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Adena Hefets is Co-Founder @ Divvy Homes, the startup that turns your monthly rent into a down payment allowing you to get on the property ladder, sooner. To date, Adena has raised over $189M with Divvy from some of the best in the business including a16z, Ray Tonsing @ Caffeinated, Max Levchin, DFJ and Threshold Ventures to name a few. Prior to founding Divvy, Adena was an early-stage fintech investor at DF. Before the world of venture, Adena was part of the original team that started Square Capital and grew the product to over 10,000 advances ($50M) within 1 year. Finally, before that, Adena started her career in the world of private equity with TPG. In Today’s Episode You Will Learn: 1.) How Adena made her way from the world of venture with DFJ to changing the way we think about homeownership with Divvy? 2.) What does Adena believe are the 3 addictions of many early-stage startup founders? How does Adena advise founders on the right way to think about paid marketing? What have been some surprising lessons from seeing Divvy's CAC change over time? How does Adena advise founders to construct a playbook and cadence for hiring? 3.) How does Adena think differently about unit economics today? Is it fundamental to have this mindset from Day 1? Where does Adena believe many founders go wrong when it comes to unit economics? Who is to blame for this desire for synthetic growth? The founders? The VCs? 4.) Considering female founders get a tiny portion of VC funds raised, how was the fundraise for Adena with Divvy? How does Adena advise other female founders and minorities on fundraising successfully? Does Adena believe that founders should always be raising? How does raising debt differ to raising equity? Why is it so much more challenging? 5.) Why does Adena believe that micromanagement can be beneficial in the early days? How does Adena ensure that it does not lead to dependencies and dejected team members? What does Adena to do push people to really get the most out of them? What works? What does not? Items Mentioned In Today’s Show: Adena’s Fave Book: Evicted: Poverty and Profit in the American City As always you can follow Harry, The Twenty Minute VC and Adena on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Carta simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to carta.com/20vc to get 10% off. More than 800,000 employees and shareholders use Carta to manage hundreds of billions of dollars in equity and Carta now offers Fund Administration so you can see real-time data in the Carta platform and work with Carta’s team of experienced fund accountants. Go to carta.com/20vc to get 10% off.

Matt Mochary coaches some of the world's leading venture capitalists and founders helping them to build the best organizations possible. On the VC side, Matt has worked with Peter Fenton @ Benchmark, several Sequoia Partners, Hemant @ GC and Mamoon @ Kleiner to name a few. As for founders, Matt has worked with the founders of Brex, Coinbase, Plaid, Reddit, Flexport and more. Prior to coaching, Matt began his business career as an investor with Spectrum Equity Investors.  He then co-founded Totality, eventually sold to MCI/Verizon.  In his own words, Matt went on to have fun (making the Academy Award short-listed documentary Favela Rising) and do good (starting the Mochary Foundation). In Today’s Episode You Will Learn: 1.) How Matt made his way from growth investor to immensely successful founder to now coaching the world's leading investors and founders? 2.) How does Matt advise founders to think about their relationship towards fear and anger? Why doe they generate bad quality of decision-making? What should be done when one recognises they are fearful or angry? Where do many founders and investors go wrong here? 3.) How does Matt advise founders who struggle with issues of self-doubt and imposter syndrome? What process should they go through to gain their confidence? What should they not do? How should they communicate their self-doubt to their team and the world? 4.) How does Matt advise founders in terms of the optimal communication strategy both with their team and their co-founders? Does radical transparency need to be instant or should it be timed correctly? What are the best conflict resolution strategies between founding teams? 5.) Why does Matt believe boards are the death of investors? Why are board members not optimally placed to advise their founders? What does Matt believe makes the best board members having worked with the likes of Peter Fenton? What does Matt advise new board members to be the best board member they can be? As always you can follow Harry, The Twenty Minute VC and Matt on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Iman Abuzeid is the Founder & CEO @ Incredible Health, the startup that connects hospitals with nurses and other high shortage healthcare professionals to dramatically speed up the hiring process. To date, Iman has raised over $17M with Incredible Health from some dear friends of the show including NFX, a16z, Charles Hudson @ Precursor and Obvious Ventures to name a few. As for Iman, prior to Incredible, she was a medical doctor, a McKinsey alumnus and led product management at AliveCor, a Khosla-backed health tech startup. In Today’s Episode You Will Learn: 1.) How Iman made her way into the world of startups from a family of surgeons and then through being a medical doctor herself? 2.) How was the fundraising process for Iman as a female minority founder? What advice would Iman give to other women and/ or minority when it comes to getting the very best investors? Where does Iman see so many founders make mistakes raising? How should founders structure their meetings with VCs? 3.) Where does Iman believe VCs can be most helpful? Where do many think VCs are helpful but they are actually not? What does Iman think of the "VC Twitter" ecosystem at play today? What investors said no along the way but Iman really liked? Why? Why does Iman believe MBA's provide such an advantage to startup founders today? 4.) How does Iman manage the psychology of being a CEO? How does Iman deal with moments of self-doubt and imposter syndrome? How has Iman seen herself evolve and change as a leader over the last 3 years? What elements have been the most challenging to come to grips with? 5.) Why does Iman still believe if you are not building your startup in the bay, you are missing out? What is so special about Silicon Valley? What advice does Iman give to founders looking to build a diverse team from day 1? How does Iman think about inevitable hiring mistakes? When is the right time to pull the plug? Items Mentioned In Today’s Show: Iman’s Fave Book: The Hard Thing About Hard Things As always you can follow Harry, The Twenty Minute VC and Iman on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Mark Goldberg is a Partner @ Index Ventures, one of the leading venture firms of the last decade with a portfolio including the likes of Dropbox, Revolut, Supercell, Plaid and Transferwise to name a few. As for Mark, since joining Index he has largely specialised on all things financial services and sits on the board of Plaid, Nova Credit, Intercom, Pilot and more incredible companies. Prior to Index, Mark spent 3 years in BizOps at Dropbox where the company increased tenfold during his time there. In Today’s Episode You Will Learn: 1.) How Mark made his way into the world of venture with Index having spent 3 years at Dropbox during a transformational time for the company? What were Mark's biggest takeaways from seeing the growth cycle at Dropbox? How did that impact his investing mindset with Index? 2.) Why does Mark believe that venture as an asset class is commoditising? What does Mark believe the best funds will have to do to stay ahead? How does Mark build relationships of trust and authenticity so early with founders? What works? What does not? What is the right way to deliver direct and tough feedback to founders? 3.) How does Mark feel about multi-stage funds re-entering seed investing again? What are the right questions seed founders should ask multi-stage funds when determining whether to take their money? What does Mark believe it takes to be competitive and win the very best of deals? How is the Founder <> VC dynamic changing with capital supply? 4.) Why does Mark believe that most angels are going to lose their money? What does Mark wish all angels knew when they started? How does Mark feel about the rise of founders investing alongside operating? What are the pros? What are the cons? How does Mark feel about the rise of scout funds? Where is there place in the ecosystem? 5.) We are seeing unparalleled levels of activity in fintech, is this a boom or are we at the start of a fundamental shift in the landscape? Why does Mark believe we will soon see our first $100Bn neo-bank? Why does Mark believe we will see a strong rise in the consolidatory environment for fintech moving forward? Items Mentioned In Today’s Show: Mark’s Fave Book: Barbarian Days: A Surfing Life As always you can follow Harry, The Twenty Minute VC and Mark on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Tomer London is the Co-Founder @ Gusto, the people platform for small businesses providing one place to run payroll, manage benefits, and support your team. To date, Tomer and the team have raised over $520M with Gusto from some of the industry's leading investors including General Catalyst, CapitalG, Kleiner Perkins, T Rowe, Fidelity and more and then individuals including Shopify Founder Tobias Luttke, Sam Altman, Max Levchin, Matt Mullenweg, Kevin Hartz and Elad Gil to name a few. Prior to Gusto, Tomer did a PHD in Electrical Engineering at Stanford and before that was Founder and CEO @ Vizmo, mobile self-service technologies for enterprise to try to fix customer care. In Today’s Episode You Will Learn: 1.) How Tomer made his way from creating inventory management software for his Father's small business in Israel to Stanford and founding the unicorn that is Gusto? 2.) Why does Tomer believe that most founders approach fundraising with the wrong mindset today? What does he mean when he says, "fundraising = creating change"? What is the "values motivation alignment"? How can founders use it to help them select the right investor for them? Why should you add investors just as you would new team members? 3.) Having raised over $200M in the latest financing, how does Tomer think about when is the right time to pour fuel on the fire and go big? Is it a fundamentally different mindset when you have so much cash thrown on you? What would Tomer advise founders with suddenly expanded budgets? With 111 investors on the Gusto cap table, what would Tomer advise founders when it comes to cap table management? 4.) What have been Tomer's biggest learnings when it comes to building a delightful product at scale across different segments? How important does Tomer feel time to delight from the UX perspective is? How does Tomer think about testing levels of user delight? NPS? Product analytics? How does Tomer think about the balance between product development and going all out for scaling? 5.) How has Tomer seen himself change and evolve as a leader of the last 5 years? What elements has he found super challenging to come to grips with? Where does Tomer believe he has a superpower on the flip side? Question from Laela @ CapitalG, what specifically did you do to create the culture that you did in the early days? Items Mentioned In Today’s Show: Tomer’s Fave Book: No Room for Small Dreams: Courage, Imagination and the Making of Modern Israel As always you can follow Harry, The Twenty Minute VC and Tomer on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Vinod Khosla is the Founder @ Khosla Ventures, one of the valley’s most renowned firms of the last decade with a portfolio including Square, Affirm, DoorDash, Impossible Foods and OpenDoor just to name a few. As for Vinod, he started his career as a Founder, founding Daisy Systems, a company that went on to IPO. Then in 1982, Vinod founded Sun Microsystems where he pioneered open systems and commercial RISC processors. In 1986, Vinod joined his longtime friend, John Doerr and became a General Partner @ KPCB where he helped incubate Juniper Networks and helped transform the telecommunications business with Cerent Corporation, which was acquired by Cisco Systems in 1999 for $7.2 billion. In Today’s Episode You Will Learn: 1.) How Vinod made his way into the world of startups with the founding of Daisy and Sun Microsystems and how that led to his entry into the world of venture with KPCB and ultimately founding Khosla Ventures? 2.) How does Vinod feel about the term "venture assistance" today? Where does Vinod believe VCs can really drive value? How does Vinod allocate his time to drive as much value for the portfolio as possible? How does Vinod get involved when it comes to talent acquisition for the portfolio? 3.) Why does Vinod believe that most board members are not qualified to advise entrepreneurs today? Why does Vinod believe that most value is driven outside of the board? What can founders to do make their boards as efficient as possible? How does Vinod advise founders to determine which advice to take vs which to disregard? 4.) How does Vinod assess his own approach and attitude to risk today? What does Vinod believe are acceptable vs unacceptable risks in startups? How does Vinod believe the very best founders think about risk management? Does Vinod agree time is the biggest killer of startups? Why does Vinod believe startups are so much quicker to innovate than incumbents? 5.) Why does Vinod believe that tolerance for failure has gone down in Silicon Valley? How does Vinod determine between the realism of when something is not work and to give up vs the visionary persistence to see a project through to the very end? What experience of his own have really led his thinking here? Items Mentioned In Today’s Show: Vinod’s Fave Book: Life on the Edge: The Coming of Age of Quantum Biology, The Third Pillar As always you can follow Harry, The Twenty Minute VC and Vinod on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Emmett Shear is the Co-Founder & CEO @ Twitch, the world's leading live streaming platform for gamers and the things we love. Prior to Twitch's exit to Amazon for a reported $970M, Emmett raised over $42M in funding from some of the best including Thrive Capital, Bessemer, Mike Maples, Aydin Senkut, Paul Graham and Y Combinator. Emmett is also a part-time Partner @ Y Combinator, advising YC companies on everything from fundraising strategy to product decisions to hiring and firing. Before Twitch, Emmett co-founded Kiko, a company he later sold on eBay for 6 figures. In Today’s Episode You Will Learn: 1.) How Emmett made his way into the world of startups with Kiko? How he ended up selling that for 6 figures on eBay? How that led to the creation of Justin.TV & Twitch? 2.) Why does Emmett believe starting a startup is like "deciding to take on the burden of Sisyphus?" At what point in the journey does is start to get easier? Does Emmett agree with many on the show who say, "it does not get easier, it just gets different"? How does one know when to give up vs when to persist and follow the vision? 3.) How does Emmett think about structuring an org at 1,500 people? Why does Emmett believe there is a fundamental tension when scaling teams between centralisation and decentralisation? How does one structure a reorg without causing instability? How does one communicate the reorg to the team? Where does Emmett see many go wrong here? 4.) Does Emmett agree the best CEOs are the best resource allocators? How does Emmett approach internal resource allocation today between both functions and projects? What does he find most challenging here? What does the decision-making process look like? What are his taekaways from Apple, Amazon and Microsoft in how they determine and process resource allocation internally? 5.) How does Emmett believe he has changed and evolved as a leader over the last 10 years with Twitch? What elements has he found the most challenging to master? What has he done to combat those weaknesses? Where has he always been naturally strong? What makes him so good at those particular functions? Items Mentioned In Today’s Show: Emmett’s Fave Book: Order without Design: How Markets Shape Cities As always you can follow Harry, The Twenty Minute VC and Emmett on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ashton Kutcher is a Founder & General Partner @ Sound Ventures. Over the last 5 years, Ashton and his partner, Guy Oseary, have built Sound into one of the West Coast's leading new entrants with a portfolio including Lambda School, Calm, Gitlab, Affirm, Bird and many more incredible companies. As for Ashton, he started his investing career as an angel with early home runs including Spotify, Alibaba, Skype, Airbnb and Optimizely. Due to his immense success both in media and technology, Ashton has been named one of TIME magazine’s “100 Most Influential People in the World”. In Today’s Episode You Will Learn: 1.) How Ashton made his way into the world of startups with his foray into angel investing in Skype, Spotify etc? How did that lead to his founding Sound Ventures most recently? 2.) How does Ashton's background in the world of media impact Sound's investment strategy and the type of deals they get excited by? Question from Daniel Ek @ Spotify: How did your deal sourcing look lin the early days? How has that changed over time and with the institutionalisation of Sound? 3.) Why does Ashton believe people creating the future are perpetually young? What question does Ashton always like to ask founders? What does he look for in their answer? How does Ashton ensure founders feel comfortable with him? What does he do to allow them to open up? What is the hardest thing Ashton feels he has persevered through? 4.) How does Ashton build strong product intuition about products in areas he is not familiar with? In terms of great product, Ashton backed Spotify with Daniel Ek and Shak Khan, what did Ashton see in Spotify way back then? How did Shak and Daniel innovate on distribution and customer acquisition with him and Spotify? 5.) What have been Ashton's learnings in what it takes to truly win the best and most competitive deals? Before as an angel, Ashton's check size was friendly, now with Sound it is competitive with VCs, how does Ashton approach the element of now competing with many VCs he once co-operated with? What does Ashton make of the rise of many celebrity investors today? Items Mentioned In Today’s Show: Ashton’s Fave Book: The Undoing Project: A Friendship that Changed the World, Scale: The Universal Laws of Life and Death in Organisms, Cities and Companies Ashton’s Most Recent Investment: Community As always you can follow Harry, The Twenty Minute VC and Ashton on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Gabriel Weinberg is the Founder & CEO @ DuckDuckGo, the Internet privacy company that empowers you to seamlessly take control of your personal information online, without any tradeoffs. Over the last 12 years, Gabe has scaled DuckDuckGo to doing 1.6Bn private searches every month, a team of 83 full time fully remote employees, raising funding from some of the best in the business; USV and most importantly, being a profitable company. If that was not enough, Gabe has also written two phenomenal books, Traction and Super Thinking.  CLICK TO PLAY CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) How Gabriel made his way into the world of startups and came to found one of today's leading search engines and privacy companies in DuckDuckGo? 2.) Gabriel decided to raise $13M from USV 4 years into the life of DDG, why did he believe that was the right time? Why does Gabe believe that DDG never needed any primary capital? How does Gabe advise founders to think when it comes to chasing profitability early? How does Gabe view the relationship between growth and capital? Are they in conflict or aligned? What does Gabe make of the many $100M rounds getting done today? 3.) How does Gabe feel about the lack of free and open distribution today? How does Gabe strategise when it comes to channel diversification? What is the right level of marketing channel diversification to have? How do you know when to really double down on one that is working? How should founders be thinking about channel saturation rates? What have been Gabes biggest lessons on payback period over the last 12 years with DDG? 4.) How does Gabe feel about the digital advertising duopoly on the internet between Facebook and Google? Why does Gabe argue that this duo of incumbents are so much more powerful than any other prior generation of incumbents? How does Gabe think about strategies to reduce their data monopolies? 5.) DDG is 83 people and fully remote, what have been Gabe's biggest lessons on what it takes to run a fully-remote team from Day 1? What mistakes did they make? WHat would Gabe advise founders contemplating the fully remote strategy? Why does Gabe have nor formal hierarchy or org chart internally at DDG? Why is this so important for culture and employee morale? Items Mentioned In Today’s Show: Gabe’s Fave Book: The Advantage: Why Organizational Health Trumps Everything Else In Business As always you can follow Harry, The Twenty Minute VC and Gabe on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jude Gomila is the Founder & CEO @ Golden, creating the world's first self-constructing knowledge database built by artificial and human intelligence. To date, Jude has raised from some of the best in the business including Founders Fund, a16z, SV Angel and one of my dearest friends, Josh Buckley. Jude is also a prolific angel having invested in over 150 companies including Carta, Airtable, Superhuman, Gusto, Linear and many more incredible companies. Prior to Golden, Jude started Heyzap (now used by 100,000 mobile apps) alongside former guest Immad, now Founder of Mercury. In Today’s Episode You Will Learn: 1.) How Jude made his way into the world of tech and Silicon Valley having been born and raised in Harrow, London? How did he then make his way into the world of investing? 2.) What models should investors and founders have common ground on? Where are founders and investors often misaligned? What does Jude mean when he says he uses "algorithms for investing"? How are these algorithms structured? What is within them? How can/should people build their own? 3.) Why does Jude very much disagree with spray and pray to be the dominant model to make money at seed? How does Jude think about portfolio construction having now made 180 investments? How has Jude's approach and attitude to ownership changed over time? 4.) Does Jude agree with Semil Shah that founders are voting with their feet and taking multi-stage money at seed today? How does Jude evaluate the approach of multi-stage funds back into seed? How does Jude think about VC value add? Where does he believe they really can add value? Where do people think they do but they actually do not? 5.) How does Jude foresee the future of the early-stage market? Will we see a generation of old school venture firms die out? Why does Jude believe younger investors have a higher chance of finding and winning the next best deal? How does Jude believe the angel ecosystem will shake out? Will we fundamentally see the unbundling of capital? Items Mentioned In Today’s Show: Jude’s Fave Book: Godel, Escher, Bach: An Eternal Golden Braid Jude's Most Recent Investment: Linear As always you can follow Harry, The Twenty Minute VC and Jude on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Shoaib Makani is the Co-Founder & CEO @ KeepTruckin, the modern fleet management platform building solutions that make drivers and fleets safer, smarter, and more efficient. To date, Shoaib has raised over $229M from some of the world's leading investors including Index, GV, Greenoaks, IVP & Scale Venture Partners. Pre-founding KeepTruckin, Shoaib was an investor @ Khosla Ventures where he led investments in Instacart, Everlane and Indiegogo to name a few. Before venture with Khosla, Shoaib was on the operations side enjoying roles at both Google and Admob. In Today’s Episode You Will Learn: 1.) How Shoaib made his way from the very comfortable world of venture to changing the way trucking fleets are managed today with KeepTruckin? How does Shoaib analyse and assess his own attitude to risk today? 2.) How has Shoaib seen himself change and evolve as a leader over the last few years? How did his time investing impact how he approaches the role of CEO? How does Shoaib think about appropriate market sizing today? What advice does he give to founders on this? What is a reasonable market penetration to assume if successful? 3.) What advice would Shoaib give founders when it comes to successful board management? How does Shoaib ensure investors have the right context at the right time to provide advice? What does that information flow to investors look like? How does Shoaib determine between the advice to accept vs what to reject? 4.) Shoaib thought about distribution and customer acquisition long before he launched the product, why? What did this thought process conclude with? Does Shoaib believe you have to own your own lines of distribution to succeed? How does Shoaib feel when it comes to current CAC's on incumbent platforms? 4.) As a founder, what does Shoaib say is his biggest mistake made in the KeepTrickin journey? How does Shoaib think about what it takes to acquire the very best talent? How does Shoaib advise founders work with recruiters? What can they do to really get the most out of them? When can this function be brought in house? Items Mentioned In Today’s Show: Shoaib’s Fave Book: Presidents of War As always you can follow Harry, The Twenty Minute VC and Shoaib on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Todd Jackson is First Round Capital's newest Partner (announced today) having spent the last 2 years as a Founder-in-Residence working with the FRC portfolio. Prior to his time in venture, Todd spent close to 3 years at Dropbox as VP Product & Design. Before that he was with Twitter as Director of Product Management, following his startup, Cover, being acquired by Twitter in 2014. Before founding Cover, Todd was a Product Manager @ Facebook where he helped lead major redesign of Newsfeed. Finally, Todd started his career at Google as a Product Lead taking Gmail from 0 to 200m users in 4 years. Todd is joined today by his Partner @ First Round, Phin Barnes. Phin also writes the most fantastic blog, sneakerheadVC, that really is a must-read. In Today’s Episode You Will Learn: 1.) Phin, what is the exclusive news you would like to break on the show today? Todd, taking one step back, how did you make your way to this stage, what was your entry into technology and how did you come to be a Partner @ First Round Capital today? What were Todd's biggest takeaways from working on some of the most transformative social products in Gmail, Twitter, Newsfeed @ Facebook and Dropbox? 2.) What advice does Phin have for Todd when it comes to entering a venture partnership? Where do many people go wrong in their first year in venture? What should Todd be optimising for in the partnership? In terms of measurement, how does one measure success of the first year of work as a Partner? 3.) Todd, making the move from angel to institutional VC is a mindset shift, how does Todd think his investment mentality will be impacted by the shift from angel to institutional VC? Having raised funding as a founder, what type of founder experience and investor does Todd want to be and bring? 4.) Phin, it has been a long time since FRC added a Partner, walk me through the recent changes at the top of FRC? What are the most important qualities for First Round when adding a Partner? What are the biggest tips to doing generational transition well? Where do many firms go wrong in generational transition? Items Mentioned In Today’s Show: Todd’s Fave Book: Creative Selection: Inside Apple's Design Process During the Golden Age of Steve Jobs, Trillion Dollar Coach: The Leadership Handbook of Silicon Valley’s Bill Campbell Todd’s Most Recent Investment: Papaya Payments, Snackpass As always you can follow Harry, The Twenty Minute VC and Todd on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Businesses are always looking for ways to shorten their sales cycles. HelloSign provides secure, effortless eSignatures proven to speed up contract signing by 80%. Most clients go from a multi-week turnaround to a multi-hour one. They’re an industry leader and have been voted #1 for Ease of Use two years in a row on G2 Crowd. Don’t let pen and paper processes slow you down. Click Here to join the millions of users already using HelloSign to close more deals faster!

Alexa Von Tobel is the Founder & Managing Partner @ Inspired Capital, announced in 2019 as the largest ever female-led VC fund based in NYC. Prior to co-founding Inspired, Alexa founded LearnVest where she enjoyed an incredible 11-year journey culminating in their $250M exit to Northwestern Mutual in 2015. Alexa is also the author of New York Times Bestseller "Financially Fearless" and is an inaugural member of the Presidential Ambassadors for Global Entrepreneurship for the White House. In Today’s Episode You Will Learn: 1.) How Alexa made her way into the world of startups with the founding of LearnVest? How did that experience running LearnVest lead to her founding NYC's largest-ever female-led VC fund in the form of Inspired? 2.) How does Alexa think about portfolio construction with the new $200M fund? What does she mean when she says they have segmented it into 3 distinct and separate buckets? How much is in each bucket? How does Alexa think about reserves and re-investment decision making? What is the process here? 3.) As a former entrepreneur, how does Alexa think about those moments when the VC and the Founder are no longer aligned? What are those moments? How does Alexa approach the aspect of saying no to founders? What is the right way? How does Alexa feel about the compression in fundraising timelines? How does Alexa meet founders before they raise their round? 4.) Why does Alexa believe that capital is no longer the differentiator? How does Alexa think about personal brand in venture today? Where does Alexa believe are the most crucial times for reputation building? How does Alexa approach time allocation across the portfolio? What is the correlation between decision-making and reputation? Items Mentioned In Today’s Show: Alexa’s Fave Book: The Power of Moments: Why Certain Experiences Have Extraordinary Impact Alexa’s Most Recent Investment: Snackpass As always you can follow Harry, The Twenty Minute VC and Alexa on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Katie Stanton is the Founder and General Partner of Moxxie Ventures, investing in founders who make life and work better. Prior to Moxxie, Katie was a Founding Partner of #angels and has the most incredible angel portfolio including Airtable, Carta, Cameo, Coinbase and Modern Fertility to name a few. Katie also served in numerous executive operating roles at Twitter, Google, Yahoo, and Color and also served in the (Obama) White House and State Department. If that was not enough, Katie is also on the board of Vivendi and previously sat on the board of Time Inc. In Today’s Episode You Will Learn: 1.) How Katie made her way into the world of tech with Yahoo? How did that translate into her investing in Lowercase Fund I? How did the angel investing lead to founding Moxxie? How has Katie found her investment mindset has changed moving from angel to VC? 2.) How did Katie find the fundraise for Moxxie? How many LPs did Katie meet and how did she structure the process? What does Katie think she did well in the fundraise? What would she look to improve or change when raising for Fund II? What advice was Katie given in the process by Semil Shah which really changed her thinking? What advice would Katie give to other emerging managers raising today? 3.) Does Katie agree with Semil Shah that "founders are voting with their feet in taking multi-stage money at seed"? What advice does Katie give to founders who do have these offers from multi-stage funds at seed? How does Katie assess these later stage funds moving earlier? How should smaller micro-managers respond to this? 4.) How does Katie think about portfolio construction today with Moxxie? What are the hard rules that mean Katie is willing to walk away from a deal? How does Katie think about and assess her own price sensitivity? In terms of decision-making, what support system has Katie built around herself to enhance her decision-making process? 5.) How does Katie advice founders when it comes to selecting their VC? What are the most common ways founders look for and need to help with? How does Katie think about party rounds? When are they good? When are they not? Why does Katie believe so much of the power has shifted to the hands of the founders? Items Mentioned In Today’s Show: Katie’s Fave Book: Becoming by Michelle Obama, Angel by Jason Calacanis Katie’s Most Recent Investment: ethel's club As always you can follow Harry, The Twenty Minute VC and Katie on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Rick Nucci is the Co-Founder & CEO @ Guru, the knowledge management platform that delivers everything you need so you can spend less time searching and more time doing. To date, Rick has raised over $38m with Guru from some of the best in the business including Thrive, Emergence Capital, Firstmark, Slack and Salesforce. Prior to Guru, Rick was the Founder of Boomi, which defined and led a new segment as the first-ever cloud integration platform-as-a-service. Boomi was ultimately acquired by Dell where Rick went on to grow the organisation into the industry leader it is today. In Today’s Episode You Will Learn: 1.) How Rick made his way into the world of startups originally and how he came to change the way we think about knowledge management with his founding of Guru? 2.) How would Rick describe his leadership style today? How has he seen his style change over the years? What have been those learnings and the inflexion points causing them? Does Rick believe can be learned as a leader? What does he recommend to founders wanting to become more empathetic? 3.) Culture is a fluffy and overused term, what does it mean to Rick? What has Rick done to purposefully build a very specific culture that he wanted to create? What specific initiatives have worked well? What have not worked so well? How does Rick think about culture maintenance with scale? What are the challenges with scaling culture? 4.) How does Rick think about the interview process when adding to the team at Guru? How do they literally structure it? What does their culture interview encompass? How heavily is it weighted? What specific questions do they ask and responses they look for? If it does not work out, what have been Rick's biggest lessons on letting people go? 5.) Rick is based in Philadelphia, often people say if you are not in a tech hub it is not possible to get the best talent, does Rick agree with this? In what roles does it make sense to hire from a tech hub for? What are the advantages of hiring outside of a hub? Fundraising wise, does Rick believe you have to have a presence in a core hub to raise from Tier 1 VCs? Items Mentioned In Today’s Show: Rick’s Fave Book: The 9 Types of Leadership: Mastering the Art of People in the 21st Century Workplace As always you can follow Harry, The Twenty Minute VC and Rick on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Howard Marks is co-chairman and co-founder of Oaktree Capital Management, a leading investment firm with more than $120 billion in assets. Prior to founding Oaktree, Howard spent 10 years at The TCW Group, where he was responsible for investments in distressed debt, high yield bonds, and convertible securities. Previously, Howard was with Citicorp for 16 years, where he served as Vice President and senior portfolio manager in charge of convertible and high yield securities. Howard has also written two books, most recently Mastering the Market Cycle: Getting the Odds on Your Side, and it was Warren Buffet who said, “When I see memos from Howard Marks in my mail, they’re the first thing I open and read. I always learn something.” In Today’s Episode You Will Learn: 1.) How Howard first made his way into the world of finance over 50 years ago? How did not getting an investment banking job change the course of Howard's life? 2.) Where does Howard think we are in the cycle today? What leads his thinking here? What is it crucial for all investors to remember at any point in the cycle? From a risk distribution and diversification perspective, does Howard believe now is a better or worse time to increase risk? 3.) Having worked through and been at the forefront of some of the most significant downturns of financial markets, what have been Howard's biggest learnings from seeing the booms and busts? How did it impact his investment mindset? At a point in 2008, Oaktree were deploying $600M per week for 15 weeks running, so how does Howard think about when is the right time to be aggressive vs when to pullback? 4.) How does Howard think about and assess his own price sensitivity? If there is one thing Howard wants to know to determine the right price, what is it? How does Howard believe we are seeing pro-risk mindsets alter investors attitude to price? How does Howard think about his right vs wrong and consensus vs non-consensus matrix? 5.) Howard and his Partner, Bruce have a very special relationship, what have they done to foster a relationship of radical intellectual honesty and that environment of safety? What are some things Howard will say to his team to encourage productive disagreement? What to Howard is the most important skill an investor can have is? Items Mentioned In Today’s Show: Howard’s Fave Book: Fooled by Randomness: The Hidden Role of Chance in Life and in the Markets As always you can follow Harry, The Twenty Minute VC and Howard on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Sumeet Gajri is the Chief Strategy Officer @ Carta, the startup that helps companies and investors manage their cap tables, valuations, investments, and equity plans. Sumeet is largely responsible for all things fundraising and M&A and Carta have raised over $485m from a16z, USV, Thrive, Spark, K9, Lightspeed and Meritech to name a few. Sumeet is also Managing Partner @ Original Capital, where he has partnered with companies including Front, Tonal, Instabase, Everlywell and Cockroach Labs to name a few. Finally, Sumeet is also an LP in world-leading firms such as USV and Valar Ventures. In Today’s Episode You Will Learn: 1.) How Sumeet made his first foray into the world of venture in NYC having grown up in Scotland? How that led to his move to operations with Carta? How his learnings from Carta led to his establishing Original Capital? 2.) How is Original Capital different from every other micro-fund? How does Sumeet approach portfolio construction with the fund? What is the optimal number in a portfolio? How does Sumeet think about loss ratio? What 3 criteria dos every new investment have to pass to make it into the portfolio? How does check size vary by deal? 3.) How does Sumeet invest in some of the best companies in between "official rounds"? What does this conversation look like with the founders? How does Sumeet analyse reserve allocations? What makes the right strategy? What are his capital concentration limits per company? How does Sumeet think about using SPVs effectively? 4.) Sumeet helps his companies fundraise a lot, what does the first step look like? How does he advise on investor selection? How does he advise on pipeline management? Should founders speak to investors when they are not raising? How open should they be in these meetings? What can founders do to catalyse the process? Where does Sumeet see many founders make mistakes? 5.) How does Sumeet think about distribution vs product? What can founders do to adopt a more distribution first mindset? What have been some of Sumeet's biggest lessons in turning Carta from a single product company to a multi-product company? Do companies have to own their own lines of distribution today? Items Mentioned In Today’s Show: Sumeet’s Fave Book: Howard Marks: The Value of Predictions As always you can follow Harry, The Twenty Minute VC and Sumeet on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Samir Kaul is a Founding Partner and Managing Director at Khosla Ventures, one of the valley's most renowned firms of the last decade with a portfolio including Square, Affirm, DoorDash, Impossible Foods and OpenDoor just to name a few. As for Samir, he led the firm's investment in Guardant Health, Impossible Foods, Nutanix [NASDAQ: NTNX], Oscar, among others. Prior to Khosla, Samir spent five years at Flagship Ventures where he started and invested in early-stage biotechnology companies, including Helicos Biosciences which went on to IPO. Samir was also founding CEO of Codon Devices and led the Arabidopsis Genome Initiative at Craig Venter’s Institute for Genomic Research. In Today’s Episode You Will Learn: 1.) How Samir made his way into the world of venture from the world of biotech and came to found one of the leading firms of the last decade? 2.) How did seeing the booms and busts of the last 2 decades impact Samir's investing mindset? Why does Samir think it is dangerous for a VC to have a "conservative mindset"? How does Samir analyse and think about upside maximisation when investing today? How does Samir think about when to sell your position and how to determine the right time? 3.) What does investment decision-making look like at Khosla? What are the criteria that re-investments are made upon? Why does Samir believe that pro-rata is a kop out? Which should be the core questions that determine whether to double down or not? How does Samir and the partnership think about time allocation across the portfolio? 4.) How does Samir approach the exercise of market sizing? Why does Samir never want to take a risk when it comes to market? Why does Samir want to maximise his risk when it comes to technological risk? How does Samir think through having to carry these deep tech companies for longer? What were his learnings from the clean tech days on this? 5.) How would Samir analyse his own price sensitivity today? What was his most formative inflexion moment as an investor? What did he learn from it? From a people side, who had the biggest impact on Samir as an investor? What were the core elements he learned from them? How does Samir deal with the element of self-doubt? How does he get through those moments? Items Mentioned In Today’s Show: Samir’s Fave Book: Start Something That Matters Samir’s Most Recent Investment: Lightship: Direct to Patient Clinical Trials  As always you can follow Harry, The Twenty Minute VC and Samir on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Kurt Rathmann is the Founder & CEO @ ScaleFactor, the startup providing an automated bookkeeping solution at its core, bringing all of your company’s important financial information into one place. To date, Kurt has raised over $105m with ScaleFactor from the likes of Byron Deeter @ Bessemer, Coatue, Canaan Partners, Stripes Group and Firebrand to name a few. As Michael @ Coatue told me before the show, there is no way Kurt was not going to be the founder of a bookkeeping company given his background. Prior to ScaleFacotr, Kurt was the CFO of KNS Communications and a Senior Audit Professional @ KPMG. In Today’s Episode You Will Learn: 1.) How did Kurt make his way into the world of startups and come to found the gamechanger for bookkeeping in the form of ScaleFactor? Does Kurt believe that Founders do need to be mission-driven or can founding a company be a more analytical exercise? 2.) How did it come to be that Kurt raised 3 separate funding rounds and over $105m in just 13 months? How does Kurt feel about the saying, "when there is money on the table, take it"? Having had his B and C pre-empted, how does Kurt feel about the rise of pre-emptive rounds today? How did Kurt approach the mental challenge of transitioning from resource-starved to relative resource abundance? Was that tough to do? 3.) What is Kurt's biggest advice to founders when it comes to investor selection? What does Kurt believe are the 5 things that VCs can do to add value? Why does Kurt believe it is the responsibility of the founder to extract that value from the VC? What can founders do to really get the most out of their investors? What has Kurt found to be the biggest value from his cap table? Where do founders think VCs add value but they do not? 4.) What are some very unique and deliberate things that Kurt does to create an amazing culture at ScaleFactor? How does he advise on creating great energy in the office itself? How does Kurt think about retaining that core ethos with the expansion to multiple offices? What have been some of the biggest challenges in scaling communications internally? 5.) Does Kurt believe that being outside of a core tech hub severely limits his ability to hire the best talent? What do founders outside of these hubs need to very strategically do? How does being outside of a core hub also impact how Kurt thinks founders need to approach fundraising? What specifically can they do to increase their odds? Items Mentioned In Today’s Show: Kurt’s Fave Book: The Empowered Challenger Playbook: How Brands Can Change the Game, Steal Market Share, and Topple Giants As always you can follow Harry, The Twenty Minute VC and Kurt on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Gaurav Jain is Co-Founder & Managing Partner @ Afore Capital, one of the west coast's leading pre-seed funds with a $124M fund focused purely on pre-seed. To date, they have backed the likes of Petal, BetterUp, BenchSci and Modern Health to name a few. Prior to co-founding Afore, Gaurav was a Principal @ Founder Collective where he was directly involved with some incredible companies including Cruise (Acq. by General Motors for $1B+), Periscope (acq. by Twitter), Airtable and Dia & Co. Before venture, Gaurav spent time in operations both at Google as one of the first engineers for Android and then also founding his own company, Polar, a leading mobile solutions provider with $10m in funding. In Today’s Episode You Will Learn: 1.) How Gaurav made his way into the world of venture with Founder Collective and how that led to the realisation that Afore needed to exist in the funding landscape? What were the 3 biggest takeaways for Gaurav from his time at Founder Collective? 2.) Why does Gaurav believe now is the hardest time in the last decade to raise your first institutional round of funding? What is driving these capital reductions at pre-seed? How does Gaurav assess the rise of operator funds and super angels we have seen in the last 5 years? How does Gaurav advise founders on investor selection at pre-seed? 3.) What does Gaurav make of large multi-stage funds entering into pre-seed? Why does Gaurav strongly believe that you cannot apply the same financing product to a different market? Does this mean the multi-stage funds will revert back to later stages? 4.) How is Gaurav seeing Series A funds behaving? Why are they more aggressive now than ever before? What does Gaurav make of the rise of pre-emptive rounds? How does he advise founders on pre-emptive rounds? 5.) How does Gaurav think about portfolio construction today with Afore? What is the right level of diversification across the portfolio to be sufficiently diversified at pre-seed? How does Gaurav think about reserve allocation today? How does the decision-making process compare when comparing initial to re-investment decision? Items Mentioned In Today’s Show: Gaurav’s Fave Book: Trillion-Dollar Coach: The Leadership Handbook of Silicon Valley’s Bill Campbell Gaurav’s Most Recent Investment: Modern Health As always you can follow Harry, The Twenty Minute VC and Gaurav on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Rahul Vohra is the Founder and CEO @ Superhuman, the fastest email experience in the world. Fun fact, users get through their inbox twice as fast — and many see Inbox Zero for the first time in years! To date, they have raised funds from our friends at Boldstart, First Round, John Collison, Sam Altman, Wayne Chang, Mike Ghaffery and Yes VC just to name a few. Previously, Rahul founded Rapportive, the first Gmail plugin to scale to millions of users. Rapportive was ultimately acquired by LinkedIn. In Today’s Episode You Will Learn: 1.) How did Rahul make his way into the world of startups with the founding of Rapportive and how did that transition to changing the world of email with Superhuman? 2.) What does Rahul mean when he says, “you can reverse engineer a process to get to product-market fit”? What does Rahul believe is the defining metric which determines your “product-market fit score”? What is Julie Supan’s framework? How did Dropbox and Airbnb use it to increase their product-market fit? How can founders implement it into their process? 3.) What can founders do to expand the customer base to include users that currently are “somewhat disappointed”? What are the right questions to ask? What do we do with this feedback? How do we further segment the user base? Why should we “disregard the users whereby the primary benefit of the product does not resonate”? 4.) How does Rahul approach product roadmap and prioritisation? How can founders ensure that continuous tracking and user feedback is engrained within the organisation? What tools does Rahul do to monitor and capture this? What are some of Rahul’s biggest lessons from going through this painstaking process stage by stage? 5.) Finally on fundraising, what does Rahul mean when he says, “always be raising but never be actively raising”? What are the benefits of this? How can founders transition catch up coffee into fundraising subtly? How does Rahul feel about party rounds? What are the pros? What are the downsides? How does Rahul advise founders here? Items Mentioned In Today’s Show: Rahul’s Fave Book: The Art of Game Design As always you can follow Harry, The Twenty Minute VC and Rahul on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Rob Salvagno is VP of Corporate Development and Cisco Investments at Cisco, where he is responsible for leading all M&A efforts as well as managing Cisco’s strategic venture capital which invests hundreds of millions of dollars annually. At Cisco, Rob led the $1.2 billion acquisition of Meraki, one of the most successful platform acquisitions in Cisco’s history, and the $3.7 billion acquisition of AppDynamics, cementing Cisco’s place in the business intelligence, analytics and IT operations market. Most recently, Rob engineered the $2.3 billion acquisition of Duo, the leading provider of unified access security and multi-factor authentication delivered through the cloud. Prior to the world of M&A, Rob was a technology investment banker at Donaldson, Lufkin & Jenrette. In Today’s Episode You Will Learn: 1.) How Rob made his way from investment banking to leading the M&A and venture activity for one of the world's largest tech players of the last decade? 2.) How do M&A teams like to get to know startups that they could invest in or acquire? How does Rob like to work with the venture ecosystem? How does Rob think on Paul Graham's comment of "do not talk to corp dev"? What are the nuances here? How does it differ for consumer vs enterprise?  3.) How does Rob define true success when it comes to M&A evaluation? Should corp dev be strategy first or transaction first? What have been Rob's biggest lessons on successful integration? Where do so many go wrong with integration post M&A? What questions can be asked ahead of time to know if integration and culture will be a fit?  4.) How does Rob reflect on his own price sensitivity today? How does Rob feel about the multiples enterprise companies are currently trading at? What have Rob's most successful acquisitions taught him about price and price sensitivity? How does Rob deal with the inherent conflict of investing and also acquiring companies? How does he communicate that to the companies he invests in?  5.) What does the acquisition-decision making process look like at Cisco? How does it differ on a deal by deal basis? What do Cisco do to allow them to move so much faster than any other M&A teams? What have been Rob's lessons on the importance of speed in winning the best transactions?  Items Mentioned In Today’s Show: Rob’s Fave Book: The Poisonwood Bible Rob’s Most Recent Acquisitions: CloudCherry, Voicea As always you can follow Harry, The Twenty Minute VC and Rob on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Bill Gurley is a General Partner @ Benchmark Capital, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many many more. As for Bill, widely recognised as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix and Zillow. Prior to Benchmark, Bill was a partner with Hummer Winblad Venture Partners. Before entering venture, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at CS First Boston where his research coverage included such companies as Dell, Compaq, and Microsoft, and he was the lead analyst on the Amazon IPO. In Today’s Episode You Will Learn: 1.) How did Bill make his way into the world of VC from Credit Suisse and come to be GP at one of the world’s leading funds in the form of Benchmark? What were Bill’s biggest takeaways from seeing the boom and bust of the dot com? How did that impact Bill’s investment mentality today? 2.) Why does Bill believe that one of the biggest challenges today is the abundance of capital? Subsequently, does Bill agree with Peter Fenton statement, “never turn down a deal based on the valuation it is a mental trap”? How does Bill assess his own price sensitivity? What was his learning here in meeting Larry and Serge early on with Google? 3.) How does Bill think about and approach market sizing today? How important is it to him when analysing an investment? Where does Bill believe a lot of managers make mistakes when assessing market sizing today? What was his big lesson here with Uber? How does Bill think about and evaluate market creation and market expansion plays? 4.) Bill has spent over 3,000 hours on some of the most famed boards of the last decade, how has Bill seen his style of board membership change over the last 10 years? What advice would you give to someone who has just joined their first board? How does Bill think about time allocation across the portfolio? What is the right ratio? 5.) How does Bill and Benchmark approach the element of partner selection today? What are the 5 core things that Bill looks for when adding to the partnership? What have Benchmark done that have allowed them to be so successful in generational transition? Why is an equal partnership so transformative when it comes to generational transition? Items Mentioned In Today’s Show: Bill’s Fave Book: Complexity: The Emerging Science at the Edge of Order and Chaos Bill’s Most Recent Investment: Good Eggs As always you can follow Harry, The Twenty Minute VC and Bill on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Brandon Deer is VP of Operations & Strategy @ UiPath, one of the world's fastest-growing companies providing a complete software platform to help organizations efficiently automate business processes through robotic process automation. To date, UiPath has raised over $977m in funding from some of the best in the world including Sequoia, Accel, Meritech, IVP, CapitalG, Kleiner Perkins, Coatue and more. As for Brandon, prior to UiPath he spent 4 years as Vice President @ OpenView Partners where he made investments in Expensify, Logz.io, VTS and Pipefy to name a couple. Before OpenView, Brandon spent close to 4 years at Intuit in Strategy and Business Development. In Today’s Episode You Will Learn: 1.) How Brandon made his way from being a rising star in the world of venture with Openview to leading one of the fastest-growing companies in history in UiPath? What has been the most surprising element in making the transition from investor to operator? 2.) How does Brandon think about decision-making today? How does he determine what to spend time on vs what to delegate? What does he mean when he says, "you have to think whether it is rubber or crystal?" How does that ultimately guide decision-making? 3.) What does the UiPath software actually do? What is the relationship between RPA and AI? Where do they differ? Where do they intersect? Recently, RPA has seen a meteoric rise, is this sustainable over the long term? How does Brandon respond to the suggestion that RPA is replacing human jobs? What is the human and societal impact? 4.) How does Brandon think about vulnerability in leadership? Why does Daniel and Brandon's relationship work so well today? What has Daniel (Founder) taught Brandon about communicating that vulnerability the right way and authentically? What does Brandon advise founders in terms of being open to their vulnerabilities? 5.) What are the biggest challenges in scaling an organisation to the 1,000+ person organisation that UiPath is today? What breaks When does it break? How does one maintain culture wit such scale? What have been the challenges of building a truly global business from Day 1? How do they look to mitigate them? Items Mentioned In Today’s Show: Brandon’s Fave Book: The Five Temptations of a CEO: A Leadership Fable As always you can follow Harry, The Twenty Minute VC and Brandon on Twitter here!    

Adam D’Augelli is a Partner @ True Ventures, one of the West Coast’s leading early-stage funds with a portfolio including the likes of Fitbit, Peloton, Hashicorp, Tray.io, Ring, Automattic (makers of WordPress) and many more amazing companies. As for Adam, he has spent close to 10 years at True where he has led investments in Hashicorp, Ring, Splice and Namely, just to name a few. Prior to joining the world of venture with True, Adam was an instructor at The University of Florida in Business Finance. Before that Adam was the Founder of Perfect Wave Records, a donation-based record label - helping bands better monetize the relationships with their fans. In Today’s Episode You Will Learn: 1.) How Adam made his way into the world of venture with True having had a slightly unorthodox start as an Instructor at The University of Florida? 2.) How does Adam think about portfolio construction today with True? Is it still possible to get 20% ownership on first check? Does Adam believe you can build ownership in subsequent rounds? Does this mean we are seeing the end to rounds being co-led? What does Adam make of pre-emptive rounds? How do True respond to them today? 3.) How does True think about initial vs re-investment decision-making? How do the decision processes differ? Does Adam believe it is possible to stack rank companies and allocate capital accordingly? What is the right way to tell a founder you will not be re-investing? How does Adam think about risk maximisation at a company level? 4.) As a partnership, how does True look to create an environment of safety where both conviction and concerns can be expressed? What should partnerships not do? Why is attribution so dangerous to this EQ of the partnership? How does the partnership work with the companies at a company level? How does True view board seats? How does True think about when is the right time to roll off boards? 5.) What were Adam's biggest takeaways from leading Ring's seed to their acquisition by Amazon? How does Adam think about the importance of market vs the importance of people when investing? How does Adam think about company failure, post-mortems and subsequent next steps? Items Mentioned In Today’s Show: Adam’s Fave Book: Doing Capitalism in the Innovation Economy: Markets, Speculation and the State Adam’s Most Recent Investment: Membio As always you can follow Harry, The Twenty Minute VC and Adam on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

John Vrionis is the Founder and Managing Partner @ Unusual Ventures, the firm that is redefining seed investing and raising the bar for what entrepreneurs should expect from a seed investment firm. Prior to founding Unusual, John spent 11 years as a Partner @ Lightspeed where his investments included Mulesoft, AppDynamics, Nimble Storage and Heptio to name a few. Before Lightspeed John spent time in product management and sales @ Determina and Freedom Financial Network. In Today’s Episode You Will Learn: 1.) How did John make his way into the world of venture and come to be a Partner @ Lightspeed? How did that lead to his founding Unusual? How did his father's MS diagnosis change his mentality towards both investing and how he views the world? What were John's biggest takeaways from his 12 years with the Lightspeed partnership? 2.) Where does John feel the bar needs to be raised in venture? What does the current product not offer? What do seed-stage founders fundamentally need? How have Unusual structured the firm to provide this? How was the fundraise for John? What does John know post-closing that he wishes he had known at the beginning? What advice would John give to aspiring emerging managers? Why is LP diversity so important to John? 3.) Why does John believe taking multi-stage money at seed is not in the best interests of the founder? How does John explain this logically to founders? Does John agree with Semil Shah, "founders are voting with their feet and choosing multi-stage funds"? Why does John believe to be truly best in class, you have to specialise? Does this not go against the data of Benchmark, Sequoia, Founders Fund, all generalist funds, having the best returns? 4.) How does John think about being company vs being founder first? What does one do when alignment erodes between the interest of the firm and the interest of the founder? How does John look to build a relationship of trust and honesty with his founders? What works? What does not work? How does John feel about VCs being friends with their founders? 5.) What is the most challenging element of John's role today with Unusual? Who is the best board member John has ever sat on a board with? Why and what did he learn? What would John most like to change about the world of venture today? What would he like to remain the same? Items Mentioned In Today’s Show: John’s Fave Book: Shoe Dog: A Memoir by the Creator of NIKE, Give and Take: Why Helping Others Drives Our Success John’s Most Recent Investment: Shujinko As always you can follow Harry, The Twenty Minute VC and John on Twitter here!

Emmanuel Schalit is the Founder & CEO @ Dashlane, the company that provides your all-in-one internet shortcut for passwords, payments and personal info. To date, Emmanuel has raised over $192m in funding for Dashlane from some of the best in the business including Jim Goetz @ Sequoia Capital, Rick @ Firstmark, Alex @ Bessemer and Habib @ Rho, just to name a few. As for Emmanuel, prior to founding Dashlane, he was the CEO @ CBS Outdoor in France and before that COO @ La Martiniere Group. In Today’s Episode You Will Learn: 1.) How Emmanuel made his way from CEO of 5,000+ people companies to founding Dashlane and changing the world of passwords and identification? How does Emmanuel asses his own risk profile moving from CEO of a large company to starting Dashlane? 2.) Is Emmanuel concerned by the excess capital available today? Why does Emmanuel believe that raising a mega-round makes your life as a founder harder, not easier? What specifically becomes harder? How does Emmanuel advise founders when it comes to burn and capital efficiency? How does Emmanuel think about when is the right time to pour fuel on the fire?  3.) Where does Emmanuel think that VCs do tangibly add real value? Where does Emmanuel believe that despite what some think, VCs do not add value in certain areas? What have been Emmanuel's biggest lessons of operating and managing a VC board? What does he advise founders starting out on this learning curve? 4.) What does Emmanuel believe are the core challenges of scale? What breaks at what specific points? How has Emmanuel seen himself scale in his role as CEO? What have been the most challenging element to scale into? How did Emmanuel get through them and what does he do to mitigate them now? Items Mentioned In Today’s Show: Emmanuel’s Fave Book: Sapiens: A Brief History of Humankind As always you can follow Harry, The Twenty Minute VC and Emmanuel on Twitter here!

David Tisch is the Founder & Managing Partner @ BoxGroup, one of the leading early-stage firms in NYC with a portfolio that includes the likes of Flexport, RigUp, Ro, Glossier, Clearbit, PillPack and Plaid, to name a few. Recently they raised their first external capital with 2 separate vehicles totalling over $160m. David is also Professor and Head of Startup Studio @ Cornell Tech. Prior to BoxGroup, he was Managing Director of Techstars NYC and before that was an Executive Vice President @ KGB. In Today’s Episode You Will Learn: 1.) How David made his way into the world of early-stage investing? How he made the transition from prolific angel investor to raising $160m+ in external capital? Why did David feel now was the right time to raise external funding after 10 years of self-funding? How has taking on external capital changed his investing mindset? 2.) Many suggest that "concentrated seed investing does not work", how does David think about and assess portfolio construction? May others also suggest that, "seed investors are not company builders", does David agree with that? Does David believe investors can change the trajectory of a company? Where can they help the most? Where do many think they help but they actually do not? 3.) Why does David believe that founders do not speak openly about bad experiences with VCs? What have been David's biggest lessons on the right way to turn down an opportunity? Do founders really want direct and honest feedback? Is it actually damaging to give it to them? Why? How does David approach this? 4.) Why does David believe "consumer social is interesting again"? Why was it not interesting for a while? How does that mean David is approaching the category? What does David mean when he says, "for the first time ever there is no channel to arbitrage on the internet"? Is David concerned by the state of CACs today? How much attention does David pay to CAC/LTV in the early days? What are the key signals? Items Mentioned In Today’s Show: David’s Fave TV Show: Survivor As always you can follow Harry, The Twenty Minute VC and David on Twitter here!

Jason Brown is the Founder & CEO @ Tally, the startup that allows you to pay off your credit card debt faster and save money. To date, Jason has raised over $92m for Tally from the likes of Mamoon @ Kleiner, Angela @ a16z, Nikhil @ Shasta and Aileen @ Cowboy just to name a few. As for Jason, prior to Tally, he spent 5 years as the Founder and CEO Kleiner Perkins backed, Gen110. Before that Jason founded Bask, a company providing both technical support and pro-active maintenance. In Today’s Episode You Will Learn: 1.) How Jason came to change the world of consumer finance with Tally having spent 5 years in the solar financing sector and even a year in venture? Given his prior entrepreneurial activities, does Jason agree with Joe Fernande @ JoyMode that "serial entrepreneurship is overrated"? 2.) Does Jason believe that founders should always be raising? What is the right way to truly determine whether an investor is aligned to your mission? What should you look for in how they behave and speak? How does Jason like to build relationships with investors pre-term sheet? Is Jason concerned by the compressed fundraising timelines today? 3.) Why does Jason believe that VC funded companies are largely not over-priced? What elements of the macro-economy does Jason attribute as the reason for the high valuations today? Why does Jason believe that we should not celebrate new fundraising? Is the celebration not good for the morale of the team? What should we celebrate instead? 4.) Why does Jason believe that the target for investors is they provide no value? What are you looking to avoid? What are the core ways an investor can damage the success of a company? What can founders do to truly extract the most from their investor base? Does Jason believe one should focus on the VC partner or the firm? Why? 5.) What does Jason believe makes the best board members? What advice would Jason give to new board members on how they can truly be the best board member? Why does Jason do onboarding sessions for all new board members? What does he look to instil in this process? What behaviour at the board should not be tolerated? How should the founder communicate this to their investor? Items Mentioned In Today’s Show: Jason’s Fave Book: Sapiens: A Brief History of Humankind As always you can follow Harry, The Twenty Minute VC and Jason on Twitter here!

Josh Buckley manages a $50m early-stage fund and as an angel has built a portfolio that includes the likes of Clearbit (Chairman), Rippling, Boom Supersonic, Lattice, Embark and many more incredible companies. Josh is also the Founder & Chairman @ Mino Games, the gaming studio he scaled to $20m in annual revenue and raising $40m in funding for the company. In Today’s Episode You Will Learn: 1.) How did Josh make his way into the world of startups at the age of just 15? How did that lead to becoming the youngest YC founder ever? 2.) What does Josh mean when he says, "the best entrepreneurs are cockroaches"? How does Josh think about capital efficiency today? Does Josh agree with Bill Gurley in stating the biggest challenge today is "the oversupply of capital"? How does Josh advise his portfolio today on raising big rounds? Capital efficiency? Burn rates? 3.) As both a fund manager and founder, what have been some of Josh's biggest takeaways from now investing in 100+ companies as an angel? How has investing impacted Josh's operating mentality? What are the benefits of angel investing? What are the potential dangers? What advice would Josh give to founders entering the world of angel investing? 4.) What are the biggest elements people underestimate when it comes to CAC? What have been Josh's biggest lessons on the volatility of CAC over time? How are we seeing the platforms evolve and develop their tech and pricing? How important is channel diversity to Josh? What is balanced? What is not? What have been Josh's biggest lessons when it comes to payback period and it changing over time? Items Mentioned In Today’s Show: Josh’s Fave Blog/ Newsletter: Paul Graham Blog As always you can follow Harry, The Twenty Minute VC and Josh on Twitter here!

Ash Fontana is a Managing Director @ Zetta Venture Partners, the fund that invests in AI-first companies with B2B business models. As for Ash, prior to Zetta he started the money side of AngelList, where, he launched online investing, created the first startup ‘index fund’. He also ran special projects like AngelList’s expansion into Europe and the UK. Simultaneously, Ash led syndicates and made investments in Canva, Mixmax and others. Before AngelList, Ash co-founded Topguest, a Founders Fund-backed company that built customer analytics technology and was ultimately sold in an 8 figure transaction 18 months after the company was founded. In Today’s Episode You Will Learn: 1.) How Ash made his way into the world of venture with AngelList and how that led to his joining Zetta today, investing exclusively in AI? What did Ash's time working on his family farm teach him about vertically integrated businesses? What were his biggest takeaways from AngelList and working alongside Naval? 2.) What does AI-first really mean to Ash? How crucial is it for companies to have proprietary datasets today? Are data moats truly defensible and real? What are the 5 characteristics that determine the level of defensibility of a dataset? How does Ash analyse the quality of a dataset? What does Ash do to determine if they are predictive of value? 3.) We often hear the term, "system of record", why is Ash so much more excited by the "system of intelligence"? Why is the basis of competitive advantage shifting from SaaS today as a model? How do the margin structure vastly differ when comparing AI-first companies to SaaS companies? How does that mean one should view capital efficiency? 4.) What does Ash believe drives business model quality? What are the commonalities in the business models of those that have made it big? Why does Ash believe it is difficult for incumbent companies to become AI-first? How difficult is it for incumbents to acquire smaller AI-first firms and integrate their policies and technology? 5.) Why does Ash love Howard marks and what has been his biggest learnings from studying him? How has Ash applied these learnings to his investing today? What has Ash also learned from the Italian masters of design? How has this study helped Ash as a VC? What has Ash optimised lately? What is Ash's favourite optimisation? Items Mentioned In Today’s Show: Ash’s Fave Book: The Strategy of Life: Teleology and Mechanics in Nineteenth-Century German Biology As always you can follow Harry, The Twenty Minute VC and Ash on Twitter here!  

Dom Holland is the Founder & CEO @ Fast, the world's fastest login and checkout with no more passwords, no more typing credit card details or shipping addresses. The special announcement today, Fast have just raised their seed round led by Jan Hammer @ Index, joined by Susa Ventures, Kleiner Perkins, Global Founders Capital and then angels including Nick Molnar, Founder @ Afterpay and proud to say I joined the round as an angel also. Prior to Fast, Domm was a Director @ Tap Tins, a network of smart tap-to-donate collection terminals. Domm was also the Founder & CEO @ Tow, an on-demand towing platform which transacted $50m in its first 4 years. In Today’s Episode You Will Learn: 1.) How Domm made his way from founding an on-demand towing company in Queensland, Australia to founding one of Silicon Valley's hottest new startups in Fast? 2.) What did Domm do in prior companies that worked and he will do again with Fast? What did not work and he will look to avoid? Does Domm agree with Joe Fernandez @ JoyMode in saying, "serial entrepreneurship is overrated"? What advice does Domm give to first-time founders? Where do they most often make mistakes? 3.) Over the last few years we have seen incredible innovation on the merchant side of payments with Stripe and Adyen but why does Domm believe we have seen no innovation on the consumer side? Why have large internet platforms not built it themselves? Does it have to be an independent 3rd party, external to Google, Facebook, Amazon etc? 4.) With the war for talent, rising rents and a lower standard of living, why did Domm choose SF as the base for Fast? How has the move been? What have been the biggest challenges? What would Domm advise founders contemplating moving to SF? How has Domm been able to hire some big hitter valley operators so early on? How does Domm think about equity sharing and optimising ESOP plans? 5.) Jan Hammer @ Index has discussed Domm's work mentality, so how does Domm structure his day? What does Domm do to ensure he optimises every minute? What work habits has Dom found to be most effective? What has not worked? How does Domm think about balancing speed and quality when executing today? Items Mentioned In Today’s Show: Dom's Fave Productivity Tool: Superhuman As always you can follow Harry, The Twenty Minute VC and Domm on Twitter here!

Rick Heitzmann is a Founder and Partner @ Firstmark Capital, one of the leading East Coast venture funds of the last decade with a portfolio including the likes of Airbnb, Pinterest, InVision, Shopify and Discord to name a few. As for Rick, he led the seed round for Pinterest and also led the deals from Firstmark in Ro, Riot Games, Draft Kings, Discord and Airbnb. Prior to founding FirstMark, Rick was an entrepreneur as a founding member at First Advantage which he helped grow and sell to First American (NYSE: FAF). Rick has been recognized by CB Insights and the New York Times as a Top 100 Venture Capitalist globally. In Today’s Episode You Will Learn: 1.) How Rick made his way into the world of venture and came to found one of NYC's leading venture funds in the form of Firstmark? 2.) How did seeing the booms and bust of the macro impact Rick's investment mentality today? With the impending crash, what 2 things does Rick advise managers need to prepare their portfolio by doing? Does Rick agree with Bill Gurley in saying, "the biggest challenge of today is the over-supply of capital"? 3.) How has Rick seen his style of investing change over the last 20 years? How does Rick think about price sensitivity today? How has that changed over the years? How has Rick seen himself change and evolve as a board member? What does Rick believe makes the best board members? What advice would Rick give to someone who has gained their first board seat? 4.) How does Rick think about the structure of the Firstmark portfolio today? How important does Rick believe it is to have temporal diversification within the portfolio? How does Rick think about optimising investment decision-making processes at Firstmark? Why does Rick believe, despite the negatives, that attribution is fundamentally important? 5.) Does Rick believe that we are in a consumer bubble today? What are the core elements that pique Rick's interest when analysing a consumer investment today? How does Rick think about CAC's scaling way faster and higher than anyone expected? Why does Rick believe the duopoly of FB and Google is now over? Why does Rick believe that true venture size exits can still occur in consumer? Items Mentioned In Today’s Show: Rick’s Fave Book: Moneyball: The Art of Winning an Unfair Game Rick’s Most Recent Investment: Crisp As always you can follow Harry, The Twenty Minute VC and Rick on Twitter here!

Ryan Denehy is the Founder & CEO @ Electric.ai, the company that provides a world-class IT solution that's centralized, secure, and lightning-fast. To date, Ryan has raised over $37m in funding from some dear friends of the show in Rich @ GGV, Bessemer, Primary, Bowery, just to name a few. As for Ryan, he started his career at the tender age of 17 launching an action sports video production company, which was acquired just 4 years later. Ryan then spent 5 years at USA Today in numerous different roles. Following USA Today, Ryan started his second company, Swarm, acquired by Groupon just 3 years later. In Today’s Episode You Will Learn: 1.) How Ryan made his way into the world of startups from launching an action sports video production company at the age of 17? 2.) Having founded 2 prior companies, would Ryan agree with Joe Fernande @ JoyMode in saying that "serial entrepreneurship is overrated"? What did he do right in the first 2 companies that he would look to do again? What did not work that he is avoiding? Where does Ryan most often see first-time founders make mistakes scaling? 3.) How does Ryan think about and assess wartime leadership? What is the right leadership style and approach to battle through the really tough times? Ryan's investors talk of his speed of execution, how does Ryan balance the speed with the quality when it comes to execution? How has Ryan seen both his role and the way in which he executes it change with the scale of the company and of himself?  4.) How does Ryan thnk about and assess forward planning when it comes to recruitment? How should this recruitment planning align to fundraising? Why must it start before the fundraise? How does Ryan think about levelling up individuals internally vs hiring external candidates? How does Ryan think about and present internal expectation setting?  Items Mentioned In Today’s Show: Ryan’s Fave Book: Barbarians At The Gate As always you can follow Harry, The Twenty Minute VC and Ryan on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Lisa Edgar is a Managing Director @ Top Tier Capital Partners, one of the leading venture fund of funds over the last decade. Included in their stellar fund portfolio is the likes of Index, Initialized, True Ventures, a16z and Boldstart, to name a few. Prior to Top Tier, Lisa was part of the asset management team at WR Hambrecht + Co focusing on new and emerging private equity funds. Before that, Lisa spent ten years at Horsley Bridge. In Today’s Episode You Will Learn: 1.) How did Lisa make her way into the world of investing in funds and how did that lead to her becoming Managing Director at one of the leaders, Top Tier? 2.) Lisa has seen the boom and bust of the macroeconomy twice now, how has that impacted her mindset today when investing in funds? What have been the most prominent changes in the venture ecosystem that Lisa has seen over the last 20 years? What changes have been good? What changes have been bad? 3.) What is the best way to get in the room with LPs? Does it have to be through warm intro? What are the signs for the GP that that first meeting went well? If an LP does not respond to emails, does that mean they don't want to do it? How does Lisa and Top Tier structure the investment decision-making process? How does that differ when re-investing in existing managers? Is it worth it for first-time funds to pitch institutions for fund 1 when they know they will not invest in the fund? 4.) How does Lisa think about GP commits today? How does Lisa look at what is reasonable and what is required? Is it individual and context-based? How does Lisa feel about different carry structures? Are kickers when past a certain return profile amenable to LPs? 5.) Lisa has seen some of the best emerging managers in the US over the last decade, what learnings does she have from them in terms of what separates the good from the great? How do they think about partnership dynamics? How do they think about firm culture? How do they think about generational transition? Items Mentioned In Today’s Show: Lisa’s Fave Book: From the Mixed-Up Files of Mrs. Basil E. Frankweiler Lisa’s Most Recent Investment: Boldstart Ventures As always you can follow Harry and The Twenty Minute VC on Twitter here!

Vlad Magdalin is the Founder & CEO @ Webflow, the startup that allows you to build better business websites, faster, without coding. To date, Vlad has raised over $73m with Webflow from some dear friends of the show including Accel, Ron @ Rainfall, Brianne @ Work Life, Benjamin Ling and Y Combinator to name a few. Prior to founding Webflow, Vlad was a Senior Software Engineer @ Intuit. Before Intuit, Vlad co-founded Chatterfox, a web application allowing people to stay in touch with groups of friends, family, or co-workers. In Today’s Episode You Will Learn: 1.) How Vlad made his way into the world of startups? How did the original idea to democratise the world of design and site creation with Webflow come about? 2.) Webflow has had an unorthodox funding path with their recent $73m Series A, how was it for Vlad raising the seed round with Webflow? What lessons did he learn from that raise? Why did they drive to be breakeven so much earlier than others might? Why did Vlad believe now was the right time to go big and raise the Series A? 3.) Vlad chose to partner with Accel, what advice does Vlad give to founders in determining which funding partner to choose? What makes for the best VC <> founder relationships? What is the optimal way to build those relationships? Where does Vlad believe that VCs can strategically move the needle? Where do many think VCs can really help but they most often cannot? 4.) What have been Vlads biggest lessons when it comes to successful board management? What advice would Vlad give Harry when it comes to joining boards as new board member? What does Vlad mean when he says, the best board members come to the board with the mindset of "servant leadership"? How do they show that in their actions? How can investors create an environment of trust at the board? 5.) Vlad AMA: Why does Vlad believe that it is a distraction for founders to be angel investing alongside their role as a founder? How does he believe this creates a wedge between them and the team? How has having kids impacted how he thinks about operating today? What have been the big takeaways from fatherhood? Items Mentioned In Today’s Show: Vlad’s Fave Book: Leaders Eat Last: Why Some Teams Pull Together and Others Don't As always you can follow Harry, The Twenty Minute VC and Vlad on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ben Horowitz is a Co-Founder and General Partner at Andreessen Horowitz, one of the leading and most prestigious venture firms of the last decade with a portfolio including the likes of Facebook, Github, Slack, Lyft, Coinbase and many more incredible companies. Ben is also the author of the New York Times bestseller, The Hard Thing About Hard Things, and the upcoming Harper Business book, What You Do Is Who You Are, available October 29. Prior to a16z, Ben was Co-Founder and CEO of Opsware, acquired by Hewlett-Packard for $1.6 billion in 2007. Previously, Ben ran several product divisions at Netscape Communications, including the widely acclaimed Directory and Security product line. In Today’s Episode You Will Learn: 1.) How did Ben make his way into the world of venture having previously co-founded Opsware? What was the original thinking for a16z? How did seeing the booms and busts of the market as an operator, impact how Ben thinks about investing today? 2.) In the book Ben says, "If soldiers trust the general, communication will be vastly more efficient". What have been Ben's biggest lessons on how to create an environment of trust quickly? As a board member, how does Ben create an environment of trust for the founder? What is Ben's advice to Harry having just gained his first board seat last year? 3.) Ben has said before of the importance of creating "shocking rules". What are the rules for creating these shocking rules? What are the best rules composed of? Given their shocking nature, how does one instil them in the organisation? What does Ben think is the most shocking rule he has implemented at a16z? 4.) What does ben believe that founders can take away from the rituals of the Samurai? Why does Ben believe that "meditating on company downfalls will enable you to build your culture the right way". Why is the negativity so helpful in forming the right culture? How does ben advise founders when their company is struggling, the team knows it and morale is low? What happened at Okta? How did they turn the culture and business around? 5.) Ben has previously spoken about bringing in external leadership from the cultures you want to master. How does one know when is the right time to bring in this external influence? What can we learn from observing Google Cloud's strategy? How does one retain the old culture but augment it with the new? What were some of Ben's biggest hiring lessons when operating? How does Ben get employees to "feel a sense of urgency", when a change needs to occur? Items Mentioned In Today’s Show: Ben’s Fave Book: The Black Jacobins: Toussaint L'ouverture and the San Domingo Revolution As always you can follow Harry, The Twenty Minute VC and Ben on Twitter here!

Steve Huffman is the Co-Founder & CEO @ Reddit, home to thousands of communities, endless conversation, and authentic human connection. To date, Reddit has raised over $550m in funding from some of the world's leading investors including Sequoia Capital, Marc Andreesen, Peter Thiel, Ron Conway, Sam Altman, Josh Kushner, Alfred Lin and Tencent, just to name a few. Steve started his career at Y Combinator as one of their first alumni back in 2005. At YC, Steve co-founded Reddit with Alexis Ohanian, which they sold in 2006 to Conde Naste Publications. In 2010, Steve co-founded Hipmunk, making business travel seamless and easy. Then in 2015, Steve re-joined Reddit as their CEO. In Today’s Episode You Will Learn: 1.) How Steve made his way into the world of startups and came to be one of the very first ever entrants in the now hailed Y Combinator? How did that lead to the founding of Reddit? Why did Steve return to Reddit, the company he founded, in 2015? 2.) What were Steve's biggest lessons from his journey with Hipmunk when it came to product feedback and iteration? How does Steve assess people's reliance on data today to drive product decisions? Why does he believe 3 criteria must be considered? What are the other two? What time did Steve see the confidence of his own intuition really increase? 3.) How does Steve think about stress management today? What was he like when he was younger in his relationship to stress? What did he actively do to change his relationship to stress? How has Steve seen himself change and develop as a CEO? What have been the inflection points? What has he struggled and also made mistakes in the journey? 4.) What have been Steve's biggest lessons when it comes to hiring truly A* talent at scale? What are the commonalities in the very best hires Steve has made? In the cases of it not working, what does Steve advise founders on the right way to let someone go? How does one do it with efficiency and compassion? 5.) Why does Steve believe that in dense cities, self-driving cars will not be that useful? How does Steve envisage the future of consumer transportation? What does he believe are the alternatives to self-driving cars? How does Steve see the future for the unbundling of social networks? Will they be unbundled into specific communities? How will this look? Items Mentioned In Today’s Show: Steve’s Fave Book: Shogun: The First Novel of the Asian saga: A Novel of Japan As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Arif Janmohamed is a Partner @ Lightspeed Venture Partners, one of the leading firms of the last decade with a portfolio including the likes of Snapchat, Mulesoft, Max Levchin’s Affirm, AppDynamics and many more incredible companies. Some of Arif's most notable companies that he has led or been involved with for LSVP includel; TripActions, Blend, Nutanix, AppZen, MoveWorks and more. Prior to Lightspeed, Arif worked in the corporate business development team @ Cisco as part of transaction leadership and execution on a number of deals including WebEx. Before WebEx, Arif founded WVP Ventures, a student-run venture capital organization. In Today’s Episode You Will Learn: 1.) How Arif made his way into venture and came to be one of the valley's leading enterprise investors with Lightspeed? 2.) We are seeing pricing hit 100x ARR multiples, does Arif believe we are seeing enterprise investing as past it's peak? Are we seeing late-cycle momentum investing? Would Arif agree with matt Harris, "Series A pricing does not matter anymore?" How does Arif assess his own price sensitivity today? How has it changed over time? 3.) Why does Arif believe that market risk is the most dangerous risk to underwrite as a VC? How does Arif think about and assess market timing? What has changed over the last few years to unlock such quantums of capital into the enterprise market? With the acquisitions of Duo, Mulesoft, Qualtrics, will we have a next-gen incumbent set or will it be an environment of existing incumbent consolidation? 4.) What does Arif specifically believe founders need to get right when it comes to company design, in order to scale to a $5-10Bn market leader? In terms of the go-to-market, who does Arif think has nailed it most recently? Why? How does Arif test for a founding team's ability to execute on go-to-market when meeting them early on? Items Mentioned In Today’s Show: Arif’s Fave Book: Stumbling on Happiness, How Not To Die: Discover the foods scientifically proven to prevent and reverse disease Arif’s Most Recent Investment: TripActions As always you can follow Harry, The Twenty Minute VC and Arif on Twitter here!

Roy Bahat is the Head of Bloomberg Beta, one of the leading early-stage funds in the valley and NYC with a portfolio that includes the likes of Flexport, Kobalt, Textio, Rigetti Computing and more incredible companies. Prior to Bloomberg Beta, Roy was the Co-Founder & Chairman @ Ouya, the company that created a new kind of games console and raised over $33m from the likes of Kleiner, Alibaba and even $8.6m on Kickstarter. Before the world of startups, Roy held numerous incredible and fascinating roles including Director of International Strategy at New York's bid for the 2012 Olympic Games and also was a Senior Policy Director in the Office of the May of New York City. In Today’s Episode You Will Learn: 1.) How Roy made his way from policy director for Mike Bloomberg to entering the world of venture and leading Bloomberg Beta? 2.) What is the big news when it comes to Bloomberg Beta? Roy has previously said, "your fund size is your strategy", what did he mean by this? What does that mean for BB moving forward? How has Bill seen what founders want from their VC change over the last 6 years? How is being "founder-friendly" vs the founder being your "customer" different? 3.) Investment Decision-Making: Does Roy believe that speed is the biggest determinant in winning deals today? What else does Roy believe is crucial? What have been some of Roy's biggest lessons in how to build trust early with founders? How does Roy and BB approach investment decision-making on initial investment? How does this change when it comes to reserve allocation decisions? 4.) Price sensitivity: Roy has said before that, "price is the dependent variable", what does he mean by this? Why is it wrong to assume that the price a VC is willing to pay shows their level of belief in your company? How does fund size change this? How does Roy think about large multi-stage funds playing at seed? How has it impacted seed? 5.) Boards: Why does Roy call boards "b-o-r-e-d-s"? When does Roy think it is important to instil a board? Why is it dangerous to have a board too early in the life of a company? What have been some of Roy's biggest lessons from sitting on a board with Alfred Lin @ Sequoia? Items Mentioned In Today’s Show: Roy's Fave Book: Ain't No Makin' It: Aspirations and Attainment in a Low-Income Neighborhood Roy’s Most Recent Investment: States Title As always you can follow Harry, The Twenty Minute VC and Roy on Twitter here!

Brianne Kimmel is the Founder and Managing Partner @ Work Life Ventures, a very new firm focused on the future of work backed by some of the best in the valley including Marc Andreesen, Chris Dixon, Zoom's Eric Yuan, InVision's Clark Valberg and then dear friends of the show, Alexis Ohanian, Garry Tan and Matt Mazzeo. To date, Brianne has invested in the likes of Webflow, Tandem, Lunchclub and Girlboss to name a few. Prior to starting Work Life, Brianne spent 2 years at Zendesk on their GTM strategy; building Zendesk for startups, ultimately representing 3,000 startups and 250 accelerators. From 2013-2017 Brianne also taught over 5,000 students at General Assembly all things user acquisition and growth marketing. In Today’s Episode You Will Learn: 1.) How Brianne made her way into the world of startups and SaaS, how that led to her angel investing and what was that a-ha moment for the founding of Work Life? Why did Brianne choose to structure Work Life as a holding company? 2.) With the fund, how does Brianne think about portfolio construction? What is the right check size for her? Why does Brianne think we are seeing more angel funds than ever today? Why are we seeing so many celebrity names on the cap tables of great companies? How does Brianne think about scout programs? What impact have they had? Why is Brianne against founders actively angel investing? 3.) What does Brianne advise founders on how to structure a high-signal round? What are the two types of angels that exist in the world today? What can founders do to keep their angels actively engaged? How have what founders expect from their angels changed over the last few years? How does one measure the true value of an angel? 4.) Does Brianne agree with Semil Shah, we are seeing "founders vote with their feet and bypass seed funds for multi-stage funds"? How does Brianne advise founders when choosing between a boutique seed firm and a large multi-stage firm? What does Brianne believe are the pros and cons of taking multi-stage money at seed? Items Mentioned In Today’s Show: Brianne’s Most Recent Investment: Pace As always you can follow Harry, The Twenty Minute VC and Brianne on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Rachel Carlson is the Co-Founder and CEO @ Guild Education, the leader in education benefits offering the single most scalable solution for preparing the workforce of today for the jobs of tomorrow. To date, Rachel has raised over $71m in funding with Guild from some of the best in venture with the likes of Michael Dearing @ Harrison Metal, Wes Chan @ Felicis, Byron Deeter @ Bessemer, Aileen @ Cowboy Ventures and Scott Raney @ Redpoint, all backing Guild. As for Rachel, prior to Guild, Rachel was the Founder of Student Blueprint, providing students with academic and career planning tools.  In Today’s Episode You Will Learn: 1.) How Rachel made her way into the world of startups having started her career in politics and how insights gleaned from politics formed the idea for Guild Education? 2.) Why does Rachel believe that ambitious Mums are the most under-utilized asset in the economy? What are the biggest misconceptions people have about hiring and working with Mums? How can founders really implement practically facilities, tools and an environment where one can be both ambitious personally and professionally? 3.) Before the show, Byron Deeter @ Bessemer said, "Rachel has been among the best at recruiting star execs across their portfolio”. What have been Rachel's biggest lessons when it comes to hiring the very best talent? Where do most go wrong? How has her hiring style changed over the years? What are Rachel's favourite questions to ask candidates? 4.) Why does Rachel believe that mission and margin are tightly integrated? How did Rachel acquire Walmart as one of their first clients? What are the positives and negatives of having a client so huge, so early? What advice would Rachel have for other early-stage companies when they have such behemoths as clients in the early days? 5.) Why did Rachel make the move from SF to Colorado? What did Rachel strategically do to ensure the chances of success were higher? How does Rachel feel about keeping leadership teams in SF and then the rest elsewhere? How did the move impact their ability to hire the best talent? How did their move impact their ability to access the best capital? Between customers, capital and employees, who is it most important to be near? Items Mentioned In Today’s Show: Rachel’s Fave Book: To the End of June: The Intimate Life of American Foster Care, Where The Crawdads Sing As always you can follow Harry, The Twenty Minute VC and Rachel on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

John Fein is the Founder and Managing Partner @ Firebrand Ventures, one of the leading early-stage funds in the midwest with a portfolio including the likes of ScaleFactor, Replica, Dwolla and more fantastic companies. As for John, prior to founding Firebrand, he was the Managing Director of Techstars based in Kansas City and before that spent close to 9 years at OptumRx where he managed multi-billion dollar large-scale programs for the $15B pharmacy benefit manager division of UnitedHealth Group. In Today’s Episode You Will Learn: 1.) How John made his way into the world of venture from scaling a pharmaceuticals business to almost $2Bn in revenue and how that led to founding Firebrand? 2.) What was it like for John raising the first fund for Firebrand with no existing network of LPs or high-net-worth individuals? How did John approach his closing strategy? How did he decide the amount of money to raise for the fund? How did Techstars Founder, David Cohen change and impact his thinking here? Was John surprised by how long the fund took to raise? 3.) What does John know now that he wishes he had known at the beginning of the fundraise for the first fund? Does it ever get easier? What does John believe are the biggest challenges in managing your own fund? What does he do to mitigate them? How does running your own fund differ from operating in a venture partnership? 4.) "Seed" is so confused in meaning today so what does "seed stage" really mean to John? Does John agree with Harry that we are seeing the eradication of the pre-seed stage? Where does John believe is the ideal insertion point? Does John believe that ownership can be built over time? How does John think about reserve allocation? 5.) How does John think about the relationship-building process with founders? Is John worried by the compressed fundraising timelines we are seeing today? What can investors do to build trust with founders quickly? What signs impress John in the early days of getting to know the founder? What are some common red flags for John? Items Mentioned In Today’s Show: John's Fave Book: Reboot: Leadership and the Art of Growing Up by Jerry Colonna John’s Most Recent Investment: The Minte As always you can follow Harry, The Twenty Minute VC and John on Twitter here!

Jason Boehmig is the Founder & CEO @ Ironclad, the startup that provides powerful legal contracting for modern legal teams. To date, Jason has raised over $84m with Ironclad from some of the best in the business including Sequoia, Accel, Greylock, Emergence, IA Ventures, Semil Shah's Haystack and Ali Rowghani who led their recent $50m Series C from Y Combinator Continuity Fund. As for Jason, prior to founding Ironclad, he was both a corporate attorney with Fenwick & West and then also an adjunct professor of Law at the University of Notre Dame. In Today’s Episode You Will Learn: 1.) How Jason left the world of law and made his way into the world of startups and came to be founder of one of Silicon Valley's hottest startups, Ironclad? How did Jason's experience at Lehmann Brothers impact his operating mentality today as a founder? What were his big lessons on personal conviction from seeing Lehmann unravel? 2.) Ironclad is famed for their customer discovery process, so how does Jason think about product development in the early days? What core questions does Jason ask to understand customer needs and desires? How does Jason determine what to implement and what to prioritise? How does Jason think about the balance between data vs gut in product decision-making? What have been his lessons here? 3.) When it comes to hiring, how does Jason approach keeping top of funnel constantly full? Why does Jason believe that when hiring, "when there is doubt, there is no doubt"? What are the common reasons that Jason does not hire a potentially strong candidate? How does Jason determine between a stretch VP and a stretch too far? 4.) How does Jason think about relationship building with VCs? Where do so many founders make mistakes in this process? What advice does Jason have on successfully negotiating with VCs? What works? What does not? What value-add has Jason realised VCs really can and do provide? Where is there a suggestion that they do but rarely do? Items Mentioned In Today’s Show: Jason’s Fave Book: Meditations by Marcus Aurelius As always you can follow Harry, The Twenty Minute VC and Jason on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Brad Feld is Managing Director @ Foundry Group, one of the most successful venture firms of the last decade with a portfolio that includes the likes of Zynga, Fitbit, SendGrid and many more incredible companies. Prior to co-founding Foundry Group, he co-founded Mobius Venture Capital and, prior to that, founded Intensity Ventures. Brad is also a co-founder of Techstars, the worldwide network of entrepreneurs in 150 countries and 300,000 alumni. Brad is also the co-author of the incredible, Venture Deals, for your chance to win a signed copy email venturedeals@foundrygroup.com with the code "First Episode". In Today’s Episode You Will Learn: 1.) How Brad made his way into the world of venture following 40 angel checks and how that led to his co-founding Foundry Group? Why did Brad find the transition from angel to VC in the early days such a challenge? What 2 core things did he focus on when writing angel checks? How has that changed now as a VC? 2.) How did seeing the boom and bust of the dot com impact Brad’s investing mindset today? How does Brad think about investing through market cycles and the right way to think about investment cadence? Why does Brad believe that to be successful as a VC you have to be fundamentally optimistic? 3.) Where does Brad believe we are today in the cycle? Does he agree with Bill Gurley on the biggest challenge being the "oversupply of capital"? What must entrepreneurs understand with regards to market cycle dynamics and how they can and need to future-proof their business? 4.) From analysing his best investments, why has Brad come to the conclusion that TAM in the early days is really not helpful? What are the commonalities in how Brad's most successful companies approach experimentation? 5.) What does Brad mean when he says, "don't have fake CEO or fake VC days"? What does he mean when he often says, "run your fucking business"? What in Brad's mind would constitute a "fake day" vs moving the needle for your business? What does Brad think is the best way for VCs to truly get to know one another? Why is, "hey let's do a deal together one of the most hollow and fake statements in venture?" 6.) Brad has sat on some of the most meaningful boards of the last 2 decades, what have been Brad's biggest learnings on what it takes to be a great board member? How does that change with the progression of your career? What advice would Brad give to me, having just gained my first board seat? If the VC does not support the CEO, what is the right process? Why does Brad believe the VC should work for the CEO? 7.) What is Brad's biggest advice when it comes to learning how to say no? What advice does Brad hear most often that he commonly disagrees with? Why does Brad feel we are in a moment of peak noise in the ecosystem today? To be a great leader, what 2 skills does Brad believe you need to have? Items Mentioned In Today’s Show: Brad’s Fave Book: Reboot: Leadership and the Art of Growing Up by Jerry Colonna, The Moment of Lift: How Empowering Women Changes the World by Melinda Gates Brad’s Most Recent Investment: Boundless As always you can follow Harry, The Twenty Minute VC and Brad on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Julia Enthoven is the Founder & CEO @ Kapwing, the startup that provides a new, collaborative platform for creating images, videos, and GIFs. To date they have raised $13m from some dear friends of the show including Saar Guur @ CRV, Mamoon Hamid @ Kleiner Perkins, Niv Dror @ Shrug and Nikhil Basu Trivedi @ Shasta. Prior to founding Kapwing, Julia was an Associate Product Manager @ Google where she worked on everything from image search to sign up workflows. In Today’s Episode You Will Learn: 1.) How Julia made her way into the world of startups and came to found the future of content editing with Kapwing? 2.) What does Julia believe are the 4 benefits to building a website over an app today? How does this change your development cadence and speed of product iteration? How does this change your economics and margin structure? Where does Julia see many founders making mistakes here? 3.) Why does Julia believe that marketing innovation is as important as product innovation? Kapwing is now at 1m users per month, what has been Julia's biggest lessons in scaling a customer base to this size with very little spend? How does Julia think about marketing channel mortality rate? How should founders approach this? 4.) Why did Julia decide it was better to bootstrap than straight away trying to raise VC dollars? What were the benefits of this? Was it the right decision? What was the turning point when Julia realised was the moment to raise external funding? How did her mindset change as a result of the funding? How does bootstrap life compare to VC funded startup? 5.) How is Julia finding the personal scaling journey from PM to CEO? What have been some of the biggest challenges? What has she done to overcome them? What advice would Julia have for other newly minted CEOs? What have been some of Julia's biggest lessons in what it takes to hire the very best talent early? Items Mentioned In Today’s Show: Julia’s Fave Book: Influence: The Psychology of Persuasion As always you can follow Harry, The Twenty Minute VC and Julia on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Matt Harris is a Partner @ Bain Capital Ventures, a leading US venture fund with a portfolio that includes the likes of LinkedIn, Lime, SendGrid, Jet.com and more incredible companies. As for Matt, he specialises in financial technology and services and has led investments in the likes of Acorns, OpenFin, SigFig, Ribbon and Billtrust. Prior to joining BCV, Matt founded Village Ventures, which he ran for 12 years and where he focused on early-stage fintech investing. Before Village Matt actually started his investing career Bain Capital private equity in 1995. In Today’s Episode You Will Learn: 1.) How Matt made his way into the world of venture from private equity and what led him to specialise as he has done in the world of fintech? 2.) How did seeing the boom and bust of the dot com impact Matt's investing mindset today? How has Matt's fear of the cyclicality of markets actually lost him a lot of money in the past? What has that taught Matt on trying to time markets? What were the main takeaways for Matt from running his own firm? How does it differ to a partnership? 3.) Why does Matt believe we are seeing late-cycle momentum investing today? What is the evidence to suggest this? How does Matt think about the right cadence to invest through market cycles? What does Matt mean when he says, "Series A valuation does not matter anymore"? Why? How does Matt assess his own price sensitivity today? 4.) Why does Matt believe that investing in improbable ideas is a good strategy? What does this mean the internal investment decision-making process looks like at Bain? Why is full consensus sometimes a concern? How does Matt approach market sizing? Why does it not matter at Series A? When does it really start to matter? 5.) Matt has said before that "backing sociopaths can work". What did he mean by this? What founder type does Matt most like to back? Does one have to manage the relationship with them very differently to other founder types? What are the acceptable risks vs unacceptable risks with this founder type? Items Mentioned In Today’s Show: Matt’s Fave Book: The Third Plate: Field Notes on the Future of Food Matt’s Most Recent Investment: Finix As always you can follow Harry, The Twenty Minute VC and Matt on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Immad Akhund is the Founder & CEO @ Mercury, the startup that makes bank accounts that help tech companies scale. To date, Immad has raised funding from some of the best in the business including a16z and CRV on the fund side and then individuals including Elad Gil, Airtable's Howie Liu, Plaid's Zach Perret, Naval Ravikant, Justin Kan and OpenDoor's Eric Wu. Prior to founding Mercury, Immad held enjoyed numerous different roles including being a part-time partner at Y Combinator and then also founding HeyZap, building developer tools for mobile game developers, ultimately acquired in 2016. In Today’s Episode You Will Learn: 1.) How Immad made his way from studying in the UK to being a YC Partner in 2017 and building one of the valley's hottest startups today in the form of Mercury? 2.) What does Immad want to do differently this time around with Mercury vs his time with HeyZap? What 1-2 mistakes that he made the first time round is Immad looking to avoid? How does being a serial founder impact one's ability to acquire the best talent? What does Immad think is harder the second time around? How has becoming a parent changed the way that Immad thinks about founding and building companies? 3.) How does Immad approach the process of picking the idea? What was the specific process with Mercury, step by step? Why does Immad believe it is an advantage to not have a background or prior career in the space you are looking to innovate in? What advice does Immad have for founders looking to move into highly regulated industries? 4.) How does Immad approach and assess the element of competition? What is the right way for founders to present competition when pitching to investors? Why is a 2x2 matrix the wrong approach? What does Immad advise portfolio founders he has invested in with regards to competition and the landscape in front of them? 5.) What have been some of Immad's biggest learnings from making over 120 angel investments? How has angel investing specifically helped certain parts of how he thinks about operating and being a founder today? What advice does Immad give with regards to investor updates? What makes the best ones? What makes the worst? How often should they be? Items Mentioned In Today’s Show: Immad’s Fave Book: The Accidental Superpower: The Next Generation of American Preeminence and the Coming Global Disaster As always you can follow Harry, The Twenty Minute VC and Immad on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Semil Shah is the Founder & General Partner @ Haystack, one of the valley's leading seed funds of the last 5 years with a portfolio including the likes of Instacart, DoorDash, Carta, OpenDoor, Hashicorp and more $Bn companies. Alongside his role at Haystack, Semil is also a Venture Partner @ Lightspeed Venture Partners. Prior to founding Swell, Semil was on the operating side as an early advisor and employee at Concept.io (Swell), acquired by Apple in August 2014. In Today’s Episode You Will Learn: 1.) How did Semil make his way into the world of venture from his start writing about startups and financing rounds? How did that also lead to his role as Venture Partner @ Lightspeed today? 2.) What does Semil mean when he says, "the most talented founders are bypassing seed firms and seed rounds"? How does this mean that seed funds need to respond? For founders, what are the pros and cons of taking a multi-stage fund at seed? Will they really get GP time with such a small check? How should they also think about potential signalling risk? 3.) Does Semil share Harry's concern with regards to pricing today? What do multi-stage funds investing at seed do to pricing? Why is staying disciplined on price the biggest challenge for Semil? How does Semil assess his own price sensitivity and when to stretch? Does Semil believe that ownership is built on first check or overtime? 4.) How does the strategy for Semil change moving from a $25m fund to a $50m fund? Why does Semil think that temporal diversification is such an important element to bake into a portfolio? What are the benefits? How does Semil think about effective reserve allocation today? What does that investment decision-making process look like the 2nd time? 5.) How has Semil seen the ecosystem for VC fundraises change over the last 5 years? What would Semil like to change about the ecosystem of LPs? What blanket rule does Semil believe that LPs should introduce for new managers to ensure discipline? For Semil, how did the fundraise differ for the latest $50m fund compared to the prior $25m fund? Items Mentioned In Today’s Show: Semil’s Fave Book: Reboot by Jerry Colonna As always you can follow Harry, The Twenty Minute VC and Semil on Twitter her

Alex MacCaw is the Founder & CEO @ Clearbit, the marketing data engine for all of your customer interactions, from customer understanding to prospect identification to personalising every sales and marketing interaction. To date, Alex has raised $17m in financing from some incredible people including Geoff Lewis @ Bedrock, Ash Fontana @ Zetta Venture Partners, First Round Capital, Battery Ventures and then former guest Ilya Sukhar, Naval Ravikant and Josh Buckley. Prior to founding Clearbit, Alex spent time in the engineering teams at both Twitter and Stripe. In Today’s Episode You Will Learn: 1.) How Alex made his way from the UK to becoming one of the hottest founders in the valley with the rise of Clearbit? What does Alex believe is more important mission and vision or organisational discipline? What does Alex mean when he says he started the company as a "vehicle for growth thinking and self-actualisation"? 2.) What did Alex mean when he said, "when you hit product-market-fit, it is time to move into company making"? What does company making mean to Alex? What would Alex like to fundamentally change about the way we manage companies today? When is the right time to make this transition? What needs to be in place to do it successfully? 3.) What does Alex mean when he says, "The 6 Pillars Behind Clearbit"? What elements does Alex think the team should not have full transparency on? How does Alex approach transparency when it comes to fundraising and M&A opportunities? What have been some of Alex's biggest learnings on both delivering and absorbing feedback? What can one do to create an environment of radical candor and rich feedback? 4.) Why does Alex believe that health has to be the #1 priority for every founder? What does that look like in practice? What can one provide the team to encourage this? How does Alex respond to those that might say, "fine but we cannot afford it"? How does Alex suggest there are 3 ways you can become more self-aware as an individual? 5.) What advice does Alex give to founders on successfully negotiating with investors? What value has Alex found that VCs really do bring? What does Alex optimise for when selecting his investor base? What value do most think that VCs bring but they actually do not? When does Alex think one should establish a board? Why does Alex think your board should only have operators and no investors on it? Items Mentioned In Today’s Show: Alex’s Fave Book: The 15 Commitments of Conscious Leadership As always you can follow Harry, The Twenty Minute VC and Alex on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ilya Sukhar is a General Partner @ Matrix Partners, the firm steeped in 40 years of history with over $4Bn invested enjoying 110 acquisitions and 65 IPOs. As for Ilya, at Matrix he has led deals in the likes of FiveTran, Flock Safety, Slab and Height just to name a few. Prior to Matrix, Ilya was a part-time investing partner @ Y Combinator and before that was Head of Developer Products at Facebook. His time at Facebook came about as a result of his former company, Parse, being acquired by them for close to $100m in April 2013. If that was not enough, Ilya also has one of the best angel tracks in the business with a portfolio including the likes of former guest Scale, Checkr, Algolia, Airtable, Gitlab the list goes on. In Today’s Episode You Will Learn: 1.) How Ilya made his way into the world of technology and startups having moved to SF from the Soviet Union? How did his growing up in the Soviet Union and moving to the US shape his thinking, operating and investing mentality today? 2.) How did Ilya's mindset change with the shift from angel investing to institutional investing? How does Ilya assess how his operating experience has impacted the way he works and engages with founders today? What are the pros? What are the cons? Why does Ilya believe the engineering CEO is so crucial? 3.) How does Ilya feel the seed ecosystem is serving startups today? What are the core ways that Ilya believes it is not optimised? How does Ila think about advising founders on the right amount to raise and the appropriate amount of runway? How does Ilya feel on the subject of bridge rounds? How does Ilya approach price and price sensitivity? What have been his learnings on price from observing his angel portfolio? 4.) Why does Ilya believe that "referencing is one of the most important skills for founders and investors"? How should founders structure their referencing? Who should they speak to? How many people is an appropriate dataset? What are the core questions to ask? How can references lead one astray? What must you watch out for? 5.) How has becoming a father changed Ilya's investing mentality today? How has it affected how he selects the projects he wishes to work on? How has it changed his relationship to time and productivity? Why in many ways does Ilya wish he had had kids earlier? Items Mentioned In Today’s Show: Ilya’s Fave Book: When Genius Failed: The Rise and Fall of Long Term Capital Management, The Stranger Ilya’s Most Recent Investment: FiveTran As always you can follow Harry, The Twenty Minute VC and Ilya on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Alex Wang is the Founder & CEO @ Scale, the data platform for AI providing high-quality training and validation data for AI applications. To date, they have raised over $123m in financing from some of the best investors in the business including Founders Fund, Index Ventures, Thrive, Spark and Coatue and then also some of the world's best operators and founders of Dropbox, Instagram, Quora, Github and Twitch to name a few. Prior to founding Scale, Alexandr was a Tech Lead at Quora, directly responsible for all speed projects and before that a software engineer at Addepar responsible for building and maintaining financial models. In Today’s Episode You Will Learn: 1.) How Alex made his way from growing up in Los Alamos to being one of the hottest founders in the valley with Scale's new round giving them a unicorn valuation? How did growing up outside the ether of the valley shape Alex's operating mindset today? 2.) Why does Alex believe that AI is under-hyped relative to the state of technology today? Would Alex agree that most projects claiming to be AI are merely rebrandings from actuarial science, data science etc etc? What questions does Alex ask to determine true AI or BS? 3.) How does Alex think about how AI can deal better with ambiguity of data? What other core areas would Alex like to see meaningful step-function improvements in? How does Alex think about the value of data-set size? How does he think about the utility value of data reducing with every incremental data point? How does Alex think about the rise of synthetic data? How does this change the landscape? 4.) What are Alex's biggest lessons on what it takes to hire incredible people before you are a hot company? How does Alex determine whether someone has the right risk profile and desire to work in a startup? What questions reveal that? Where does Alex believe that many go wrong in the early days of hiring? What would he do differently now? 5.) For the $100m Series C, how did the round come together? What did the process look like? How did this round compare to the other rounds? How does Alex think about and approach the element of investor selection? How can founders build relationships with investors in these hyper-compressed fundraising timelines? What have been Alex's biggest lessons when it comes to CEO growth and then also board management? Items Mentioned In Today’s Show: Alex’s Fave Book: 7 Powers: The Foundations of Business Strategy As always you can follow Harry, The Twenty Minute VC and Alex on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Jana Messerschmidt is an investor @ Lightspeed Venture Partners, one of the best performing funds of the last decade with a portfolio including Snapchat, Mulesoft, Max Levchin's Affirm, Cameo, StitchFix and many many more incredible companies. Prior to LSVP, Jana co-founded #Angels in 2015, a first of its kind investment collective specifically designed to get more women on the cap tables of successful companies. Her portfolio includes the likes of Carta, Lambda School, Bird, Forward and Cameo to name a few. In addition to #Angels, Jana spent 6 years at Twitter as VP of Global Business Development and Platform where she led the 150+ person organization responsible for Twitter's global strategic partnerships. Finally, before Twitter, Jana spent 2 years at Netflix as Director of Business Development.  In Today’s Episode You Will Learn: 1.) How Jana made her way from the worlds of Twitter and Netflix to founding #Angels and becoming an angel to today, investing on the front lines with Lightspeed? 2.) What were some of Jana's biggest takeaways from her time with Netflix? How did that experience impact her operating mentality today? How can leaders determine the true quality of their team and their conviction in them? What is "the leaver test"? What does Netflix do internally to drive such high performance? What does Jana mean when she says, "leaders have to provide context, not control"? 3.) Does Jana believe that founders should "always be raising"? What is the right way for founders to approach OKR setting with regards to requirements for the next round? When should this OKR discussion for the next round take place? Who should be involved? How can founders get potential investors to do the work upfront and determine interest? 4.) In terms of metrics for the Series A, they depend based on the vertical and business model but what is required, metric wise, to raise a Series A in: A D2C brand? What revenue levels would be expected? What growth levels would be expected? A consumer subscription business? What level of churn is acceptable? What does Jana see as a good CAC/LTV? Why does Jana believe that you cannot grow your business on ad spend perpetuity? How does Jana think about the cost of advertising today? What have been her biggest lessons when it comes to how CAC changes over time? 5.) What tips and advice does Jana give to founders to allow them to enter fundraising negotiations with leverage? What can founders do to gain leverage if their numbers are not in place? What does Jana think should be some of the biggest considerations for founders when it comes to their cap table? 6.) How does Jana think that founders can put their cap table to work in the most effective way? Is there a way to stress their suggested "value-add" prior to their investment? What can be done to actively improve the lack of women and underrepresented minorities on cap tables? What would Jana like to see change here? Items Mentioned In Today’s Show: Jana’s Fave Book: Elad Gil's High Growth Handbook, Dark Money As always you can follow Harry, The Twenty Minute VC and Jana on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Clark Valberg is the Founder & CEO @ InVision, the digital product design platform powering the world's best user experiences. To date, Clark has raised over $350m with InVision from some of the world-leading investors including Iconiq, Spark Capital, Accel, Battery Ventures, Tiger Global, FirstMark and even Atlassian. Prior to founding InVision, Clark spent 8 years as the Co-Founder of Epicenter Consulting, a leading web application design business. If that was not enough, Clark is also a leading angel with a portfolio including Algolia, Voiceflow, Unsplash and BentoBox, just to name a few. In Today’s Episode You Will Learn: 1.) How Clark made his way from running a successful design agency to fundamentally changing the way designers design products and consumer experience them through InVision? 2.) Why does Clark believe that all aspiring entrepreneurs questions have a false premise? What is the fundamental false premise of entrepreneurship? How does Clark assess the importance of vision and mission over alternate elements? What advice does Clark give to the many aspiring entrepreneurs that ask for his advice? 3.) How does Clark think about market timing today as an entrepreneur? How does Clark think investors should approach and think about market timing? How does Clark look to measure impact not just size of the market? How has angel investing changed Clark's operating mentality as an entrepreneur with InVision? 3.) Why does Clark believe that enlightenment is a daily task? What does Clark do to fundamentally make himself present enough to appreciate those inflection points and moments of enlightenment? How can everyone use note-taking to gain this level of self-consciousness? How are the notes structured? What routine needs to be built around them? 4.) How does Clark think about taking the time to appreciate the milestones that are achieved? Why do we have to make celebrating a ritual? What can be done to ensure these moments of company and personal growth are recognised? What have been Clark's biggest moments of realisation on this theme? 5.) With InVision being an almost fully remote team, what have been Clark's biggest breakthroughs in making it work so well with his marriage and his family? What are "date days"? How does Clark use them to ensure the right balance of work and romance? What has Clark found to be the weirdest thing of operating a 900-person remote firm? Items Mentioned In Today’s Show: Clark’s Fave Book: Positioning: The Battle for Your Mind: The Battle for Your Mind As always you can follow Harry, The Twenty Minute VC and Clark on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Mike Vernal is a General Partner @ Sequoia, one of the world’s leading and most renowned venture firms with a portfolio including WhatsApp, Zoom, Stripe, Airbnb, Github and many more incredible companies. As for Mike he has led and sits on the board of Citizen, rideOS, Rockset, Threads and Houseparty (acquired by Epic). Prior to venture, Mike spent 8 years at Facebook as VP of Product & Engineering leading multiple different teams including Search, Commerce, Profile, and Developer product groups. Prior to Facebook Mike spent 4 years at Microsoft as a PM lead in Microsoft's Developer Division. In Today’s Episode You Will Learn: 1.) How Mike made the move from VP of Product & Engineering at Facebook to General Partner at the world-famous, Sequoia Capital? What were Mike's biggest takeaways from his 8 years at FB seeing the hyper-growth first hand? 2.) Mike has previously said that he has struggled in the past when it comes to "overthinking investments". What does he mean by this? How does it play out in reality? How does Mike balance between trusting his gut and relying on the data? How does Mike think venture partnerships should participate in this balancing act? 3.) Why does Mike believe decision-making in venture to be fundamentally different to decision-making in operations? How do they compare? How does the decision-making process and approach change as a result of this contrast? How does Mike think about his own time allocation now in venture? What is the most challenging element? 4.) How does Mike evaluate the proliferated SaaS landscape today? Why does Mike believe that the notion of SaaS as a construct will fade over the coming years? What does Mike believe is the reasoning for SaaS apps becoming more and more niche? What problem does that pose for VC? Will we enter a period of consolidation in SaaS? What size do the incumbents have to be to really engage in the M&A process moving forward? 5.) Why does Mike struggle to see the strength of data moats? What are the major downfalls associated with the argument of their strength? At what point is the asymptotic point of the utility value of the data for models today and how does that change over the coming years? What does Mike instead see as durable and sustainable moats? Items Mentioned In Today’s Show: Mike’s Fave Book: One Hundred Years of Solitude  Mike’s Most Recent Investment: Verkada  As always you can follow Harry, The Twenty Minute VC and Mike on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Daniel Kan is the Chief Product Officer @ Cruise, the company building cutting-edge hardware and software that work seamlessly together to transform the way we all experience transportation. In 2016, Cruise was acquired by GM for a reported $1Bn. Since the acquisition Cruise has raised $7.25 billion in committed capital and has attracted SoftBank, Honda, and T. Rowe Price as investors. As for Daniel, he started his career at a startup called UserVoice. He then founded Exec, an on-demand hospitality service company, and successfully sold Exec to Handy. As a result of his many success, Daniel was listed as number 7 on Fortune’s 2016 40 under 40 list for the most influential people in business. In Today’s Episode You Will Learn: 1.) How Daniel made his way into the world of startups and came to co-found the game-changing company of the next movement mega wave of transport innovation in Cruise? 2.) What have been Daniel's biggest lessons on what works for leaders in scaling themselves? How can a leader ensure their team feel real ownership and accountability for their roles? How does Daniel think about KPI and goal-setting? How does Daniel look to strike the balance between ambitious but achievable goals and then unrealistic? 3.) How does Daniel think about micro-management? Is there ever a time for it? What are the leading indicators you or someone on the team is micro-managing? What can they do to correct it? What are the dangers of micro-management? How does Daniel think about assessing human potential in terms of a stretch VP and a stretch too far? 4.) Why does Daniel believe that "if you are not growing, you are dying"? What has been transformational to Daniel in increasing his own level of self-development and learning? How does the organisation need to be set up to ingest these learnings in real-time and improve? Where do many go wrong when it comes to mistakes and learnings? 5.) At acquisition, Cruise had just 40 team members, today the team consists of 1,460. What have been some of Daniel's biggest lessons in the process of scaling the team with such rapidity? What have been some of the core challenges? How has Daniel's style of leadership had to change and evolve with the growth? Items Mentioned In Today’s Show: Daniel’s Fave Book: Shogun: The First Novel of the Asian saga: A Novel of Japan As always you can follow Harry, The Twenty Minute VC and Daniel on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Puneet Agarwal is a Partner @ True Ventures, one of the leading early-stage VC funds of the last decade with big wins including Fitbit, Peloton, Ring, Hashicorp, Duo Security and Blue Bottle Coffee, just to name a few. As for Puneet, at True he has led deals in Duo Security, Tray.io, Lumity, Solo.io and more. Before the world of VC, Puneet spent 6 years in product management with Geodesic Securities and BEA. Before product management, Puneet actually cut his teeth in the world of VC as an associate at Mayfield which he joined post a 2-year stint at JP Morgan. In Today’s Episode You Will Learn: 1.) How Puneet made his way into the world of venture from JP Morgan? How seeing the boom and bust cycle impacted his investing mindset today? How his career in operations led to his joining True? 2.) Why does Puneet believe that EQ is going to separate the good from the great in venture firms over the next decade? What can VCs do to remove the barriers to access them? What have been Puneet's biggest lessons on what it takes to build real relationships of trust and respect with founders? What is a test of a strong founder <> VC relationship? 3.) What does Puneet believe are the 2 feelings a board member can bring to a board meeting? Why would an investor bring fear to the board meeting? Why is this a sign and result of the culture of their own venture partnership? What have been Puneet's biggest lessons on how investors can bring the feeling of safety to a board meeting? How has Puneet changed his style of board membership over the last decade? 4.) Why does Puneet strongly advocate for a venture structure without attribution? What are the benefits of not having attribution? How does this also impact the re-investment decision-making process? How does Puneet think about how he spends his time across the portfolio? What have True done to optimise the investment decision-making process? Why is unanimity not required? 5.) How does Puneet and True think about portfolio construction today? What amount of initial checks give them enough diversification to feel comfortable but also enough reserves to double down? Does Puneet believe that ownership can be built over time? Where does Puneet believe there is a whole in the funding environment? How does True think about minimizing risk on the first check? Items Mentioned In Today’s Show: Puneet’s Fave Book: Billion Dollar Whale: The Man Who Fooled Wall Street, Hollywood, and the World Puneet’s Most Recent Investment: Upsie As always you can follow Harry, The Twenty Minute VC and Puneet on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Hiten Shah is the Co-Founder @ FYI, the startup that allows you to find your documents in 3 clicks or less. Before FYI, Hiten co-founded QuickSprout alongside Neil Patel, together they scaled the platform to over 500,000 readers every month. Before QuickSprout, Hiten was the Co-Founder and CEO of KISSmetrics, raising over $19m in the process for the company from the likes of True Ventures, Uncork Capital and Felicis Ventures just to name a few. Finally, Hiten is also the Co-Founder @ Crazy Egg, the heat mapping tool used by thousands to improve the effectiveness of their websites. Finally, Hiten is also an angel investor with a portfolio including Buffer, Clearbit, Front, Gusto and more incredible companies. In Today’s Episode You Will Learn: 1.) How Hiten made his way into the world of startups, growth market and SaaS and how that led to his co-founding FYI today? Having founded multiple startups, does Hiten agree with Joe Fernandez @ JoyMode that "serial entrepreneurship is overrated"? Why does Hiten believe that fundamentally, nobody knows what they are doing? 2.) How does Hiten feel about the compression of fundraising timelines today? How does Hiten advise founders on building authentic relationships with investors? What is it crucial that founders understand about the investing class? How does Chetan advise founders on building hype and urgency within their fundraising? What works? What does not? 3.) Why does Hiten believe that we have seen the eradication of the friends and family round? What other large trends has Hiten observed in the early stage over the last few years? How does Hiten advise founders on how to approach which seed investors they take on board? Does Hiten think founders and investors can be friends? 4.) How has Hiten seen himself change and evolve as a leader over the last decade? What have been the biggest learnings on what great leadership really means? What are the 5 core elements that all great leaders must focus on? How does he split his time across these 5 disciplines? Where do founders often not spend adequate time among the 5? 5.) How does Hiten think about the element of "burnout" and depression today? Has Hiten ever felt burned out himself? How does this stress manifest itself? How does Hiten think that burnout and control are correlated? What can one do to change their relationship to control? What has worked for Hiten? What has not? Items Mentioned In Today’s Show: Hiten’s Fave Book: The Courage To Be Disliked  As always you can follow Harry, The Twenty Minute VC and Hiten on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Chetan Puttagunta is a General Partner @ Benchmark, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many many more. As for Chetan, at Benchmark he has led deals in the likes of Duffel, Sketch and Pachyderm. Before Benchmark, Chetan was a General Partner @ NEA where he led investments in Elastic, MongoDB and Mulesoft to name a few. In Today’s Episode You Will Learn: 1.) How Chetan made his way into the wonderful world of venture, came to invest in Mulesoft and Elastic and how that led to becoming a GP with Benchmark today? 2.) How does Chetan feel about the push to run businesses based on metrics and benchmarks relative to other companies? What are the metrics they should hone in on? What are the metrics they should disregard? How does Chetan advise his portfolio on the right way to view competition? What is core to analysing competition effectively? 3.) How does Chetan assess the "war for talent" in terms of startup recruiting today? How do the very best CEOs recruit the best talent to their team? Who has done this best from Chetan's portfolio that comes to mind? How much weight does Chetan place on references? What should one watch out for with references? 4.) With the rise of remote, does Chetan believe that a startup even has to have an office in SF today? How does Chetan think about the "tribal knowledge" that remains within the valley? What does Chetan advise his companies that are not in the valley and contemplating it? What works? What does not? 5.) How does Chetan think about market size today when considering new opportunities? Where does Chetan think most managers go wrong when assessing TAM? How does Chetan think about time allocation across the portfolio? What have been his biggest lessons on managing his time effectively as an investor and board member? Items Mentioned In Today’s Show: Chetan’s Fave Book: Shoe Dog: A Memoir by the Creator of NIKE Chetan’s Most Recent Investment: Duffel As always you can follow Harry, The Twenty Minute VC and Chetan on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Waseem Daher is the Founder and CEO @ Pilot, the startup that takes care of your bookkeeping from start to finish so you can focus 100% on making your business succeed. To date, Waseem has raised over $58m in funding from some of the very best firms and people in the business including Index, Stripe, Okta's Frederic Kerrest, Gusto's Josh Reeves, Stripe's Patrick and John Collison and Lola's Paul English, just to name a few. As for Waseem, Pilot is the 3rd business he has founded with his co-founders, the first being Ksplice and the second Zulip, which was acquired by Dropbox in 2014. He has also enjoyed spells with the likes of Oracle and Dropbox in the interims. In Today’s Episode You Will Learn: 1.) How Waseem made his way into the world of startups over 15 years ago and how that lead to his founding of Pilot today, changing the world of accounting? Does Waseem agree with Joel Fernandez at JoyMode that "serial entrepreneurship is overrated? What has Waseem done differently this time as a result of his 2 prior founding experiences? 2.) Why does Waseem believe that "passion is overrated when it comes to starting companies"? If passion is not fundamental, what does Waseem believe is fundamental to ensuring one sticks the course? How does Waseem think about the craft of company building as a passion in itself? 3.) What is it about Waseem's relationship with his 2 co-founders that makes it so successful for the third time around this time? What do they do to ensure that unity and trust remains? Where do they have weaknesses and flaws in the co-founding relationship as a result of it's maturity? What advice does Waseem give to newer co-founding partners? 4.) Waseem has previously said that "VC is overrated". What does he mean by this? How does Waseem think about the decision to bootstrap vs to raise VC? What are Waseem's biggest lessons when it comes to investor selection? How much of a role does brand play? What core questions should the founders ask the VC? 5.) What does Waseem mean when he says, "never sell your company"? What were his biggest lessons from exiting two companies to Oracle and Dropbox? How did it shape his thinking on M&A and exits? How has Waseem seen his role scale and develop as a leader and as CEO? What are the biggest challenges he has found in his personal scaling? Items Mentioned In Today’s Show: Waseem’s Fave Book: Harry Potter As always you can follow Harry, The Twenty Minute VC and Waseem on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Smart executives and business owners know that harnessing the power of AI, embracing the cloud, and prioritizing cybersecurity are the cornerstones of growth. Every day, Wrike helps thousands of companies worldwide do this by revolutionizing how they approach work. Our secure, automated,cloud-based work management tool helps businesses future proof their cultures and evolve fast. How? Wrike ‘s award-winning, collaborative, all-company platform keeps everything in one easily-accessible space. Time to embrace next-gen work management at the executive level and encourage lean thinking from the top down. With Wrike, crushing your objectives and mitigating risks at scale is a cinch. Give Wrike a try for free.

Brian Norgard is the Former Chief Product Officer at the top-grossing mobile app in the world, Tinder. In less than 3 years, Tinder created over $11Bn in market value and with Brian's creation of Tinder Gold, Superlike and Boost, the platform has seen over 200m downloads and created millions of matches. Prior to Tinder, Brian founded Tappy, a mobile messaging application backed by Kleiner Perkins and acquired by Tinder. Before that, Brian built one of the fastest-growing Facebook applications in history (Chill) which reached over 30MM people. Fun fact about Brian also, at 25, Brian was the youngest GM/VP in the history of Rupert Murdoch’s News Corp after the acquisition of his first company Newroo where he served as the GM of MySpace News. If that was not enough, Brian is also a prolific angel investor with investments in Tesla, SpaceX, AngelList and Coinmine. In Today’s Episode You Will Learn: 1.) How Brian made his way into the world of startups and came to be the youngest VP at News Corp at the tender age of 25? How did that lead to his becoming CRO then CPO @ Tinder? 2.) What is the No 1 reason that products fail today? What can founders and designers do to retain the simplicity of product over time? How does complexity change the product experience? Why does Brian believe that product experience is an art? Bring in science, to what extent does Brian believe testing and iteration is key to success in product? How does one know how long is enough time to test for vs too short and not enough data? 3.) When thinking about distribution, what does Brian look for in the way that people describe a product to their friend? How does Brian think that the most successful products bake distribution into the core user behaviour? How does Brian think about community building around product? Who has done this best in Brian's mind? 4.) How should the very best founders and product people think about product risk? How can they know when to use risk to their advantage vs be mindful of excessive risk? On the features themselves, how important is it for a product to be 10x cheaper/faster etc? Why does Brian believe that is largely VC jargon? 5.) What were Brian's biggest takeaways from launching Tinder Gold and seeing Tinder become the Top Grossing App in the world? How does that sort of event also impact the team? How does Brian think about whether one should celebrate those moments or push forward to the next goal? Items Mentioned In Today’s Show: Brian’s Fave Book: The Old Man and The Sea As always you can follow Harry, The Twenty Minute VC and Brian on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Smart executives and business owners know that harnessing the power of AI, embracing the cloud, and prioritizing cybersecurity are the cornerstones of growth. Every day, Wrike helps thousands of companies worldwide do this by revolutionizing how they approach work. Our secure, automated,cloud-based work management tool helps businesses future proof their cultures and evolve fast. How? Wrike ‘s award-winning, collaborative, all-company platform keeps everything in one easily-accessible space. Time to embrace next-gen work management at the executive level and encourage lean thinking from the top down. With Wrike, crushing your objectives and mitigating risks at scale is a cinch. Give Wrike a try for free.

Jesse Beyroutey is a General Partner @ IA Ventures, one of the top-performing early-stage funds of the last decade. Their incredible portfolio includes the likes of TransferWise, DataDog, Digital Ocean, X.ai and The Trade Desk, just to name a few. As for Jesse, his investments at IA include Digital Ocean, IronClad, TransferWise, Sight Machine and more fantastic companies. Prior to joining the world of venture, Jesse studied Systems Engineering at the University of Pennsylvania. In Today’s Episode You Will Learn: 1.) How Jesse made his way into the world of VC pretty much straight out of University and how that led to his being a GP with IA today? 2.) What is Game Theory? What does it mean to Jesse and how does it impact his investing mindset today? How does Jesse think about and assess startup positioning today? How important is positioning in the early days of the company? How does Jesse think about data as a sustainable moat or not? Does Jesse think in today's excess supply of capital environment that cash alone can be a moat? 3.) How does Jesse and IA think about portfolio construction today? Does Jesse ever feel the "pressure to deploy"? How have IA structured their own fundraises to ensure they never feel that pressure? How important a role does ownership play for Jesse when making an investment? Does Jesse believe ownership is built on first check? 4.) How does Jesse assess his own price sensitivity? How has it changed over the last 8 years? How does Jesse and IA approach both investment decision-making and reserve allocation decisions? How does the lead rely on the rest of the team when making decisions? Why does capital efficiency become a core question when determining reserve allocations? 5.) Why does Jesse feel that the reading to writing ratio that currently exists between founders and investors needs to change? What should the ratio be? How does the relationship between founder and investor change when the investor provides more content? How does Jesse look to avoid news cycles in the week? What works? What does not? What is Jesse's advice for anyone looking to do the same? Items Mentioned In Today’s Show: Jesse’s Fave Book: 7 Powers: The Foundations of Business Strategy Jesse’s Most Recent Investment: Gauntlet  As always you can follow Harry, The Twenty Minute VC and Jesse on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Sid Sijbrandij is the Founder & CEO @ Gitlab, a single application for the entire software development lifecycle. From project planning and source code management to CI/CD, monitoring, and security. To date, Sid has raised over $145m in funding for Gitlab from the likes of GV, August Capital, YC, Khosla and Goldman Sachs just to name a few. What is incredible, Sid has scaled the team to over 762 team members across 55 countries and is famed for his openness and transparency on how he builds both the product and company. You can find the fantastic Gitlab handbook here. In Today’s Episode You Will Learn: 1.) How Sid made his way into the world of startups, learned Ruby in the early days and came to found Gitlab? What was that a-ha moment? 2.) In 2019 Gitlab is growing from 400 to 1,000 people, what are the biggest challenges that come with such operational growth? How does one hire at such pace and retain quality? How does Sid think about the right way to onboard new employees? How does Sid think about KPI and goal setting in the early days?  3.) Today all 750 Gitlab employees are remote, what does Sid believe is the secret to making remote teams work at scale? How does Sid think about the balance between fast shipping cadence and perfect product releases? Why does Sid believe, "you have to have a low level of shame on the product you release"? 4.) How does Sid think about operating Gitlab as a totally transparent company? What does that mean both in reality and in process? Why does Sid believe it is optimal to have a roadmap that is open for everyone to see? What are the pros? What are the cons of such transparency? How do competitors respond?  5.) If every great business is bundling or unbundling, where does Sid believe he and Sid are in the process today? How does Sid think about being too much to too many people? How does the open-source community really come into play in the development of Gitlab? Items Mentioned In Today’s Show: Sid’s Fave Book: High Output Management As always you can follow Harry, The Twenty Minute VC and Sid on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Santi Subotovsky is a General Partner @ Emergence Capital, one of the valley's leading venture firms of the last decade focusing on enterprise & SaaS applications. Within their incredible portfolio is the likes of Salesforce, Zoom, Box, Veeva Systems, SuccessFactors and many more. As for Santi, he has led deals in the likes of Zoom, Crunchbase, Clearbanc, Top Hat and Chorus.ai to name a few. Before Emergence, Santi founded AXG Tecnonexo, a SaaS e-learning company in Argentina which he expanded to 150+ employees across Latin America and the U.S. Santi is also a founding board member of Puente Labs, an organization that helps founders of Latin American high-potential growth companies scale their businesses globally. In Today’s Episode You Will Learn: 1.) How Santi made his way from founding a Latin American EdTech business to being one of the valley's most successful investors of 2019 with Zoom's IPO? What was the biggest barrier he faced when getting into VC? How did he overcome it? 2.) What does Santi believe his superpower as an investor is? What did Santi see in Eric Yuan and the 30 person team at the time that made him believe they would be successful? What made how Eric thinks about presents product so special? What did the relationship building process look like between Eric and Santi in the early days? 3.) How does Santi like to work with his portfolio companies? How does Santi think about time allocation across the portfolio? Why does Santi believe it is crucial to not just spend time with the CEO but the exec team also? Where does Santi most like to provide value and leverage to the CEO? Why does Santi believe all VCs are just sales reps? 4.) Why does Santi believe that a vertically focused fund is the optimal strategy to pursue today? What are the benefits? What are the drawbacks? How does Santi think about the obvious overlap between consumer and enterprise today? With the thematic focus, how does Santi think about loss ratio and batting average? How does Emergence approach the element of both ownership and price? Where do they optimise? 5.) With larger and larger funds, how does Santi see the future of venture? Why does he believe that we will see vertically focused capital-as-a-service? What does this look like in reality? Is Santi concerned by the extended window of privatisation that is now present in today's capital markets? How concerned is Santi by the compression of fundraising timelines and what does that to investor <> founder relationships? Items Mentioned In Today’s Show: Santi’s Fave Book: Candide by Voltaire Santi’s Most Recent Investment: Openpath As always you can follow Harry, The Twenty Minute VC and Santi on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Joseph Gordon-Levitt is the Founder @ HitRecord, the startup that allows you to be creative, together, encouraging less self-promotion and more collaboration, so you can create things you couldn't have made on your own. To date, Joe has raised funding from some personal favourites of mine in the form of Alex @ Javelin, Masterclass Founder David Rogier, Twitch Founder Kevin Lin and CrossLink Capital just to name a few. Alongside his role with HitRecord, Joe is also an A-List Hollywood Actor and filmmaker starring in some of my favourite films of all time including The Dark Knight Rises, Inception, 10 Things I Hate About You and many many more. In Today’s Episode You Will Learn: 1.) How Joseph made his way into the world of technology and startups with the founding of HitRecord? How did much of Joe's early acting career inform much of the HitRecord product today? 2.) Having had such success in the acting world, what caused Joe to really push forward with HitRecord? Question from David @ Masterclass: who has been Joe's biggest mentors in his transition to tech? What have been his biggest takeaways from them? How does Joe balance both being an actor and entrepreneur at the same time? What are the challenges? 3.) Why did Joe decide now was the time to raise VC funds for HitRecord this late into the company life? How does Joe approach the element of investor selection? What specific value add did Joe want to see in his potential investor? How did the pitch process go? How does it compare to presenting for a role in the acting world? What was Joe's biggest lesson about what successful technology pitches do? 4.) When Joe thinks about the HitRecord community, what has surprised him the most with the growth of the community? Why have they purposefully decide to never spend on user acquisition or traffic? What is the strategy behind this? What is Joe's biggest advice to individuals wanting to scale their community and the essentials? 5.) How does Joe assess both the content and social media landscape today? Why is the creative spirit of the world being killed by the current ad model of social platforms? How does Joe think this can be countered and where does HitRecord fit into this evolving landscape? Items Mentioned In Today’s Show: Joe’s Fave Book: Letters To A Young Poet As always you can follow Harry, The Twenty Minute VC and Joe on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Byron Deeter is a Partner @ Bessemer Venture Partners where he has established himself as one of the leading investors in SaaS and Cloud authoring the iconic laws on the state of cloud computing. In terms of track record, fourteen of Byron’s investments are valued above one $1 billion, including eight IPOs and counting. Byron's investments include the likes of Twilio, Intercom, SendGrid, Gainsight, Box, DocuSign and many more. Prior to the world of venture, Byron was a Bessemer Founder raising his Series A from them back in 2000 with Trigo Technologies. The company rapidly scaled to profitability and was acquired by IBM. In Today’s Episode You Will Learn: 1.) How Byron made his way into the world of venture from founding Trigo Technologies and selling to IBM in 2005? How have seeing multiple booms and busts impacted Byron's investment mentality today? 2.) What the heck is going on in cloud today? Is Byron concerned by the very rich multiples being paid in the ecosystem today? How does Byron think about how public market performance impacts his day to day role investing? Why does Byron believe that the floodgate for cloud IPOs is about to burst open? 3.) Having seen so many cloud IPOs, what should founders take from the lessons of those that have already been so successful? With 14 $Bn companies, what does Byron attribute his investing success to today? How does Byron think about what he wants to invest in today? Are we in an entirely new wave of cloud? 4.) As a former founder, how does Byron think that he engages differently with founders than more financial backgrounded VCs? What can board members really do to build that trusted relationship with the founder in the early days? Is it good for founders and board members to be friends? Is there a line of professionalism that has to be drawn? 5.) How has Byron seen his style of board membership change over the last decade? What would his advice be to someone who has just gained their first institutional board seat? What does Byron believe makes the best board members? What founder he has worked with most excels when it comes to board management? What made them so extraordinary? Items Mentioned In Today’s Show: Byron’s Fave Book: AI Superpowers, Legacy Byron’s Most Recent Investment: ScaleFactor As always you can follow Harry, The Twenty Minute VC and Byron on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Alex Rodrigues is the Founder & CEO @ Embark, the world's leading developer of self-driving trucks. Embark operates the longest automated freight route in the world. To date, Alex has raised over $47m in funding for Embark from some of my favourites in the form of Pat Grady @ Sequoia, Matt Ocko @ Data Collective, SV Angel and Y Combinator, just to name a few. As for Alex, it started early with his winning a World Robotics Championship while he was in Middle School (the championship was for adults). Post that incredible achievement he dropped out of Waterloo, became a Thiel Fellow, worked as a software engineer @ Nuance Communications, before joining Khan Academy as a software engineer and also teaching robotics @ Khan Lab School. CLICK TO PLAY CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) How Alex made his way from winning World Robotics Championships while he was in Middle School to founding the leader developer of autonomous trucks in Embark? 2.) Why does Alex believe in the medium to long term, self-driving is still under-hyped? What is the market analysis to support this? How did his meetings with the world's best public markets investors impact his thinking here? How does Alex think about adoption timelines for self-driving? How do investors think about this when investing? 3.) Does Alex believe that when it comes to self-driving vehicles, they will largely be a public utility? What ownership mechanism does Alex expect to see? What are the pros and cons associated with each? How does Alex think about ownership of the data generated through self-driving? How do we balance privacy and public safety? 4.) With such large milestones and proof points in self-driving, how does Alex think about effective goal setting? What are the core KPIs to be driving for? How can they be broken into more meaningful and achievable wins for the team to get around? What is the core challenge to morale maintenance when the challenge is so long term? 5.) Where does Alex see the commonalities in the biggest mistakes that young founders make? What does Alex know now that he wishes he had known at the start? What have been Alex's biggest lessons on hiring the world's best in their respective fields? What have been Alex's biggest takeaways when it comes to successful board management? Items Mentioned In Today’s Show: Alex’s Fave Book: High Output Management As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Pat Grady is a Partner @ Sequoia, one of the world's leading and most renowned venture firms with a portfolio including WhatsApp, Zoom, Stripe, Airbnb, Github and many more incredible companies. As for Pat, at Sequoia he co-leads the firms growth investment team and has been involved with some of the true greats, Hubspot, Zoom, Okta, Qualtrics, the list goes on. Prior to Sequoia Pat spent three years with Summit Partners. In Today’s Episode You Will Learn: 1.) How Pat made his way from Summit Partners to co-leading Sequoia's growth investment team? Was it intimidating for Pat entering a partnership with Jim Goetz, Don Valentine, Roelof Botha? How did he manage those nerves? 2.) So many different funds and activities, so what is Sequoia focused on today? Where does Sequoia think about their ideal insertion point today? How do they see the deployment of their blended capital across rounds? Does Pat believe in ownership on first check or building ownership over time? How does Pat think about the extended window of privatisation with IPOs being continuously delayed? 3.) Does Pat believe that VC really is a team sport today? Does Pat agree with Josh Kopelman's statement, "I would rather be a better picker of partners than investments"? What are the core requirements, skills and traits that Sequoia looks for when adding to their partnership? 4.) What is the investment decision-making process at Sequoia? How do they feel about unanimity vs conviction based investment decisions? What are the pros and cons of each? What does Pat believe is the most non-obvious investment decision that Sequoia have made? Sequoia run an incredibly rigorous process when investing, how does Pat balance between that level of rigour with the speed to win the deal? 5.) What advice would Pat give to someone that has just gained their first institutional board? What does Pat know now that he wishes he had known when he started in VC? How does Pat think about time allocation across the portfolio? Concentrate on winners or the strugglers are where your reputation is built? Leading Sequoia Growth and with a beautiful family, how does Pat approach work/life balance? Items Mentioned In Today’s Show: Pat’s Fave Book: God Friended Me Pat’s Most Recent Investment: Embark: Revolutionizing Commercial Transport  As always you can follow Harry, The Twenty Minute VC and Pat on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Steven Galanis is the Founder & CEO @ Cameo, the startup that allows you to book personalised shoutouts from your favourite people. To date, Steven has raised over $65m in VC funding for Cameo from some of the very best in the business including Bedrock, Nicole Quinn @ Lightspeed, Kleiner Perkins and Spark Capital, just to name a few. Prior to founding cameo, Steven was a Senior AE @ LinkedIn and before that was an options trader in Chicago. With their immense success, they have been featured in all major publications including The Ellen DeGeneres Show. Cameo has also been voted as "The Best Place To Work In Chicago" by GlassDoor. In Today’s Episode You Will Learn: 1.) How Steven made his way from AE @ LinkedIn to revolutionising what an autograph means today with his founding of Cameo? 2.) What does Steven believe is the No 1 reason that startup founders fail with their startup today? Why does Steven believe that you have to give up your job to pursue your startup, even in the earliest of days? What advice does Steven give to founders and young graduates who approach him for advice in the earliest of days? 3.) As the company scales, how does Steven think about and approach role allocation internally? How does he prioritise hiring for them? How does he think about internal upscaling? How has he dealt with letting go of responsibilities and delegating to the team? What are the core challenges here? What does he advise founders facing this? 4.) Steven has said before, "don't let good get in the way of great", what did he mean by this? How does he determine between good enough and a stretch too far? How does Steven think about the statement of hiring for 6 months ahead of where you are? What have been his biggest lessons from scaling internationally so fast? 5.) How does Steven think about and approach investor selection? What can founders really do to leverage their investor base and get the most value from them? How does Steven think about the incredibly high CACs of the core channels today? What must founders in the world of consumer do to acquire customers more efficiently? Items Mentioned In Today’s Show: Steven’s Fave Book: Blitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies As always you can follow Harry, Steven and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Bill Gurley is a General Partner @ Benchmark Capital, one of the most successful funds of the last decade with a portfolio including the likes of Uber, Twitter, Dropbox, WeWork, Snapchat, StitchFix, eBay and many many more. As for Bill, widely recognised as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix and Zillow. Prior to Benchmark, Bill was a partner with Hummer Winblad Venture Partners. Before entering venture, Bill spent four years on Wall Street as a top-ranked research analyst, including three years at CS First Boston where his research coverage included such companies as Dell, Compaq, and Microsoft, and he was the lead analyst on the Amazon IPO. In Today’s Episode You Will Learn: 1.) How did Bill make his way into the world of VC from Credit Suisse and come to be GP at one of the world's leading funds in the form of Benchmark? What were Bill's biggest takeaways from seeing the boom and bust of the dot com? How did that impact Bill's investment mentality today? 2.) Why does Bill believe that one of the biggest challenges today is the abundance of capital? Subsequently, does Bill agree with Peter Fenton statement, "never turn down a deal based on the valuation it is a mental trap"? How does Bill assess his own price sensitivity? What was his learning here in meeting Larry and Serge early on with Google? 3.) How does Bill think about and approach market sizing today? How important is it to him when analysing an investment? Where does Bill believe a lot of managers make mistakes when assessing market sizing today? What was his big lesson here with Uber? How does Bill think about and evaluate market creation and market expansion plays? 4.) Bill has spent over 3,000 hours on some of the most famed boards of the last decade, how has Bill seen his style of board membership change over the last 10 years? What advice would you give to someone who has just joined their first board? How does Bill think about time allocation across the portfolio? What is the right ratio? 5.) How does Bill and Benchmark approach the element of partner selection today? What are the 5 core things that Bill looks for when adding to the partnership? What have Benchmark done that have allowed them to be so successful in generational transition? Why is an equal partnership so transformative when it comes to generational transition? Items Mentioned In Today’s Show: Bill’s Fave Book: Complexity: The Emerging Science at the Edge of Order and Chaos Bill’s Most Recent Investment: Good Eggs As always you can follow Harry, The Twenty Minute VC and Bill on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Justin Kan is the Founder and CEO @ Atrium, the startup providing a full-service corporate law firm that uses modern technology to give startups a legal experience that is fast, transparent, and price-predictable. To date, Justin has raised over $75m in funding from some of the best in the business including Founders Fund, a16z, First Round, General Catalyst, Thrive, Initialized and more. Prior to founding Atrium, Justin was a Partner @ Y Combinator, the globally renowned accelerator and the birthplace of some of today's largest startups. Before that Justin was the Co-Founder @ Twitch, the world’s leading video platform and community for gamers which was acquired by Amazon for $970m. If that was not enough, Justin is also a prolific angel investor with investments in the likes of Cruise Automation, Rippling, Zenefits, Triplebyte and more. In Today’s Episode You Will Learn: 1.) How Justin made his way into the world of startups and YC? How that led to the founding of Justin.TV, later Twitch? What was that a-ha moment for Atrium? 2.) Why did Justin feel that being an investor full time was not for him? How does Justin think about and approach the learning process as a founder? What advice does Justin give to those who want to quit? What was it that made Justin embrace the series of self-improvement habits he now practices? 3.) What does Justin mean when he says, "attaching yourself to outcomes will only cause your own suffering”? How does Justin think about and advise founders when it comes to burnout? How does Justin feel about the "crushing it" culture in tech? What can we do to normalise vulnerability? What were Justin's biggest takeaways from "The Score takes Care of Itself"? 4.) What have been Justin's experiences with therapy? How does he advise founders thinking of engaging with therapists? What have been his biggest lessons that drive success in therapy? How does Justin look to show authenticity through positivity? What does that really mean? 5.) What have been Justin's biggest takeaways from "The 15 Commitments of Conscious Leadership"? What are the core principles? What is required to roll out these values and principles within an organisation? What are the fundamental challenges to successfully roll this out on a large scale within your company? Items Mentioned In Today’s Show: Justin’s Fave Book: The 15 Commitments of Conscious Leadership As always you can follow Harry, Justin and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jonathan Hsu is Co-Founder & General Partner @ Tribe Capital, one of Silicon Valley's newest funds on the block being founded by Jonathan, Arjun Sethi and Ted Maidenberg. To date, Tribe has invested in the likes of Carta, Cover, Mode Analytics, Prodigy and SFOX. As for Jonathan, before founding Tribe he was a Partner @ Social Capital where he utilized data and technology to augment sourcing, evaluation of investment opportunities and the management and value add for portfolio companies. Before that he led the creation of the analytics and data science team at Facebook, including leading the hiring of 200 of the world's leading data scientists and analysts. In Today’s Episode You Will Learn: 1.) How Jonathan made his way from leading 200 data scientists at Facebook to the world of venture and founding his own firm in the form of Tribe Capital today? 2.) If we structure VC simplistically, there are 4 core components: Sourcing: How does Jonathan think about the role of data in actively surfacing the best opportunities? that are the leading data fields that Jonathan would track? Why does Jonathan believe most early-stage firms are just using Linkedin Sales Navigator intelligently? Evaluating: How does Jonathan think about the potential for data to really aid in the picking process? At what stage does this really become possible? How much data is required for data to evaluate opportunities? Winning: Winning deals is seemingly a case of human relationships but how does Jonathan think intelligent data usage and benchmarking can actually help firms win the most competitive deals? Value Add: How does Jonathan think about portfolio management with data? How does this differ from the more traditional "value add" that other VCs provide? Where are the common pitfalls Series A companies you work with face in not achieving product-market fit? 3.) Given the data-driven nature of the approach, does Jonathan think that there is an optimal portfolio construction? Why does Jonathan strongly believe that historical loss ratios are too high? Does data allow firms to really intelligently price these assets at the Series A and B? What are the challenges in pricing these assets so early? 4.) How does Jonathan think about reserve allocation? Why is data more critical than ever in the decision to re-invest or not? What are the leading data signals that Jonathan looks for when determining reserve allocation? Why does Jonathan think that so many firms go wrong in how they approach reserve management and distribution? 5.) Question from Henry Ward @ Carta: What does N of 1 markets mean to you Jonathan? Why are they so inherently attractive? How do pricing dynamics play out in markets that are N of 1? How does Jonathan think about defensibility when analysing opportunities today? Is anything truly defensible anymore? Items Mentioned In Today’s Show: Jonathan’s Fave Book: The Origins of Political Order: From Prehuman Times to the French Revolution Jonathan’s Most Recent Investment: Carta As always you can follow Harry, The Twenty Minute VC and Jonathan on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Brad Bao is the Co-Founder & CEO @ Lime, the startup that provides distribution of shared scooters, bikes and transit vehicles, with the aim to reduce dependence on personal automobiles for short distance transportation. To date they have raised over $775m in funding from the likes of Andreessen Horowitz, GV, IVP, Uber, Fifth Wall, GGV, Atomico and Bain Capital Ventures just to name a few. As for Brad, prior to founding Lime he was Managing Partner @ Kinzon Capital for close to 6 years and before that spent an incredible 8 years at Tencent in numerous different roles including VP of Business Development for Tencent Games and General manager for Tencent's US branch where he was responsible for Tencent's US operations. In Today’s Episode You Will Learn: 1.) How Brad made his way into the world of technology with Tencent, how that led to the world of investing and then what was that a-ha moment for the founding of Lime? How did Brad's time with Tencent impact his operating mentality today with Lime? 2.) With significant levels of competition, how does Brad assess the competitive landscape today for micro mobility? Does Brad believe customer loyalty comes into play in the segment? Is capital itself a defensible moat in this market? Why is Brad adamant that it is important to spend $0 on marketing? What does this say about the product? 3.) How does Brad think about technological innovation within the space? Does it subscribe to Moore's law in the advancement of the core components? How does Brad think about inherent trade-offs that have to be made in product decisions? How does Brad think about prioritising for unit cost vs product superiority? Why can you not have it all? 4.) How does Brad think about launching new cities? What does it take to win in those geographies? What are all the necessary parts to setup when entering a new location? What is the biggest determinant of a location success? Density? Maturity? 5.) Brad has assembled a truly world-class exec team, what does Brad think it takes to attract truly A* talent? When should founders really start to think about building out their own exec team? What does Brad believe it is that makes his partnership with Toby Sun work so well? What have been his learnings from the development of that relationship? Items Mentioned In Today’s Show: Brad’s Fave Book: Good To Great by Jim Collins As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Scott Kupor is Managing Partner @ Andreessen Horowitz, one of the world's most renowned venture funds with a portfolio including the likes of Facebook, Airbnb, Github, Lyft, Coinbase, Slack and many more. As for Scott, he has been with the firm since its inception in 2009 and has overseen its rapid growth, from three employees to 150+ and from $300 million in assets under management to more than $7 billion today. Before a16z, Scott was a VP @ HP where he managed a $1.5 billion (1,300 person) global support organization for HP Software product portfolio. Scott joined HP as a result of his prior company Opsware, being acquired, where he served as a Senior VP across numerous roles across an incredible 8-year journey.  In Today’s Episode You Will Learn: 1.) How Scott made his way from the world of law to startups to being Managing Partner at one of the world's most renowned venture firms in the form of a16z? 2.) How did seeing the boom and bust of the dot com bubble and 2008 impact Scott's operating mindset today? Why does he argue that those times are so drastically different to today? How do public markets fundamentally diffferent? How do teams approach to capital efficiency and scaling differ significantly? 3.) What does Scott believe entrepreneurs get most wrong when pitching VCs? Why does Scott argue that product is not the core when pitching VCs? Does Scott agree with Fred @ Okta in weighing it: 70% market, 20% team, 10% product? What is Scott's weighting? Why does Scott believe that the compression of fundraising timelines is a problem? What pitch sticks out to Scott above all others? What made it so memorable? 4.) How does Scott advise founders on determining the right amount to raise for? Does Scott believe that founders should ask for a specific number or a range? Why does Scott believe raising for "runway" is the wrong mindset? Does Scott believe that most bridges are bridges to nowhere? If so, what is the next step? How does one relay that information to the founders? 5.) What have been some of Scott's biggest learnings from building the firm with Marc and Ben? What does Scott believe have been the biggest inflexion points in the public status of a16z? What have been the biggest challenges for Scott in the scaling of the firm? How does he foresee that changing in the future? Items Mentioned In Today’s Show: Scott’s Fave Book: Master of the Senate: The Years of Lyndon Johnson As always you can follow Harry, The Twenty Minute VC and Scott on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Zach Perret is the Founder & CEO @ Plaid, the startup providing the easiest way for users to connect their bank accounts to an app whether it be transactions, identity or authentication. To date, Zach has raised over $300m with Plaid from some of the best in the business including Mary Meeker, Index Ventures, Andreessen Horowitz, Felicis, Spark and Homebrew, just to name a few. As for Zach, as CEO he has scaled Plaid to today with over 300 employees, 3 international offices and over 10Bn transactions analysed. Prior to founding Plaid, Zach was a consultant @ Bain. In Today’s Episode You Will Learn: 1.) How Zach made his way into the world of startups from consulting at Bain and what led to the founding of Plaid and the mission to unlock consumer finance? What advice would Zach give to emerging grads today, questioning whether to join or start a startup? 2.) What does great leadership and CEOship look like to Zach? How has Zach seen himself evolve and develop as a leader over the last few years? How does Zach think about prioritisation? How does Zach determine what to say yes vs what to say no to? What has Zach found the most challenging in scaling as a CEO? What has he done to mitigate this? 3.) How does Zach think about constructing the optimal recruitment process? What have been some of Zach's biggest lessons in what it takes to really recruit world-class talent? What does Zach mean when he says, "you have to hire for spikes"? How does Zach manage the tension of keeping the high-quality bar whilst also sustaining the very steep growth curve? 4.) Plaid recently raised $275m, how does Zach think about capital efficiency with Plaid today? How does Zach determine when is the right time to transition from the mindset of lean and iteration to raising a war chest and going for the home run? What is Zach's biggest advice to founders when it comes to investor selection? Is it possible for the investor and the founder to be "friends"? 5.) When assessing the fintech landscape today, what is Zach most excited to see develop over the next 12-18 months? How are we seeing much larger incumbents like Goldman innovate in the proliferated world of fintech startups? How does the US view the fintech innovation that has occurred in the UK? What does this mean for US fintechs? Items Mentioned In Today’s Show: Zach’s Fave Book: Hard Drive: Bill Gates and the Making of the Microsoft Empire As always you can follow Harry, The Twenty Minute VC and Zach on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Zach Coelius is Managing Partner @ Coelius Capital and in his own words, "a pretty eclectic investor who loves to see just about any deal". To date, Zach has made investments in the likes of mParticle, Cruise Automation, Branch Metrics, SkySafe, ProsperWorks and more. In addition, Zach is or has been an advisor to LiveRamp, Hellosign, Art19, Loom.ai, Survata and StartGrid just to name a few. Prior to his investing career, Zach was CEO @ Triggit, an online adtech company which he raised over $18m for and was ultimately acquired in 2015. If that was not enough, Zach is also a Senior Advisor to McKinsey & Co. In Today’s Episode You Will Learn: 1.) How Zach made his way from the world of operating and adtech to investing and advising startups today? When does Zach feel the ecosystem really started to take him seriously as an investor? What did Zach learn from being in the adtech space that he has applied to his investing today? 2.) The Future of Venture: Naval has previously said we will see "the unbundling of VC", does Zach agree with this view? Why does Zach feel we are seeing both the bundling and the unbundling of venture platforms? What unique challenges does this pose for both sides of the equation? How should entrepreneurs evaluate the different options, bundled vs unbundled? 3.) Portfolio Construction: Why does Zach believe that portfolio construction is fundamentally inefficient? What 2 core areas of venture does portfolio construction cause issues for? When does Zach view to be the ideal insertion point if optimising for absolute returns and not following portfolio construction? 4.) Reserve Allocation and Pricing: Why does Zach think that the current mechanism for reserve allocation is broken? Why is it a fundamentally bias process? What does the optimal investment decision-making process look like to Zach? How does Zach think about the asymmetric information that is gained from being early into a company? How can investors really use it to their advantage? Why do they not? 5.) Why does Zach compare being an entrepreneur to being a gladiator and a rocketship? Why does Alex believe the transition from space articulation to product articulation is the most important thing an entrepreneur can do? What is the true sign of this transition in customer interactions? Where do many entrepreneurs make mistakes here? Items Mentioned In Today’s Show: Zach’s Fave Book: The Snowball: Warren Buffett and the Business of Life Zach’s Most Recent Investment: Mud\Wtr As always you can follow Harry, The Twenty Minute VC and Zach on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Kulveer Taggar is the Founder & CEO @ Zeus Living, the startup providing a home of your own for business travel with smartly furnished homes for extended stays. To date, Kul has raised over $14m in VC funding from some dear friends of the show in the form of Garry and Alexis @ Initialized, James and Pete @ NFX, Mike @ Floodgate, Y Combinator, GV and Naval Ravikant just to name a few. Prior to Zeus, Kul co-founded Auctomatic alongside Stripe's Patrick Collison, they ultimately sold the company for $5m. Before that, Kul co-founded Bosco, alongside former 20VC guest, Monzo's Tom Blomfield, they raised seed funding from YC before moving to the states to start Auctomatic. If that wasn't enough, Kul has also made several angel investments in the likes of Boom, Airhelp, Meetings.io and more. In Today’s Episode You Will Learn: 1.) How Kul made his way from Oxford University to being at the centre of one of tech's most powerful hubs of YC and then with the founding of Zeus? What were Kul's biggest takeaways from his first 2 startups? How did that impact his operating mentality? 2.) What did the idea generation process look like for Kul with Zeus? How was James Currier @ NFX so foundational helping here? Why does Kul believe that the idea "really is everything" today? Why does Kul believe that customer acquisition channels are a core part of the product that must be considered from Day 1? 3.) Before hitting on Zeus, Kul and the team had many ideas, what did that idea validation process look like? How did Kul keep morale high in the team when continuously trying and stopping work on new projects? How does Kul think you can use culture as a superpower? As a leader, how can you be both vulnerable and strong at the same time? 4.) Kul has previously said that "tech-enabled businesses are just much harder than pure software plays". Why is that? What makes them so much more challenging? How do the required skills to be successful change when moving from pure software to tech-enabled? What single question remains the most important to ask when innovating in either? 5.) VCs are not so used to such operationally heavy businesses so how did Kul find the fundraising process? Why does Kul advocate that all founders should speak to investors and A/B test their idea before starting work on it? How did investors differ when comparing SF vs NYC? How did the messaging have to change? What was the most common pushback or concern? What have Initialized done to have such a foundational impact? What makes Garry such a special investor to have on board? Items Mentioned In Today’s Show: Kul’s Fave Book: How The Mind Works by Steven Pinker As always you can follow Harry, The Twenty Minute VC and Kul on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Geoff Ralston is President @ Y Combinator, the world's leading accelerator with a portfolio that includes the likes of Stripe, Airbnb, Dropbox, Coinbase, Instacart, DoorDash, Flexport and so many more. As for Geoff, he started his career running engineering at Four11, where he built RocketMail, which in 1997 became Yahoo! Mail. At Yahoo! Geoff worked in engineering, then ran a business unit, then became Chief Product Officer. After Yahoo! he was CEO of Lala, which was acquired in 2009 by Apple. Post Lala, Geoff then co-founded the world’s first educational technology accelerator, Imagine K12 which funded dozens of edtech companies including ClassDojo, Remind, and Panorama Education. Imagine K12 merged with YC in 2016. In Today’s Episode You Will Learn: 1.) How Geoff made his way into the world of technology and startups, came to found Imagine K12 and how that led to becoming President @ Y Combinator today? 2.) What were Geoff's biggest takeaways from seeing the boom and bust of the macro environment in the dot com and 2008? How did those times impact both his operating and investing mentality? Why does Geoff believe 2000 was "purifying"? Why can the same not be said for 2008? How was 2008 so different? 3.) Frederic Kerrest @ Okta said: "it is 70% market, 20% team and 10% product", would Geoff agree with this weighting? How has his weighting changed over time? YC has "10 Minute Meetings", how can YC really determine whether someone is investable in 10 mins? How does Geoff think about the hailed VC term, "pattern matching"? Why does Geoff believe you lose as an investor if you fall back on "profiles"? 4.) Geoff has worked with 100s of founders in the idea validation stage, how does Geoff know when a founder has the right idea? How does Geoff think about the balance between mission and vision but then also being realistic about when something is not working? When do you quit? Why is the decision internal not external? What is the most important perspective any investor can give a founder? 5.) How does Geoff think about the coined term "product-market fit" and how does he analyse it in terms of retention and growth? If they have some signs of it, how should founders think about when is the right time to raise their first round? How does Geoff think about the benefits for founders of convertibles and now SAFE's? What does Geoff believe will be the future of legal round mechanics? Items Mentioned In Today’s Show: Geoff’s Fave Book: Titan: The Life of John D. Rockefeller As always you can follow Harry, The Twenty Minute VC and Geoff on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Mathilde Collin is the Co-Founder & CEO @ Front, reinventing the email inbox with new workflows and efficient collaboration so people can accomplish more together. To date, Mathilde has raised over $79m in VC funding with Front from some of the best in the business including Bryan Schreier @ Sequoia, Initialized, Uncork Capital, Boldstart and individuals including Andrew Chen, Elad Gil, Ray Tonsing the list goes on. With 4,500+ customers, and 100+ employees, in Paris, San Francisco and Amsterdam, Front is one of the fastest growing companies in SaaS and Mathilde has become a thought leader for the next generation of SaaS CEOs, read more on her blog here.  In Today’s Episode You Will Learn: 1.) How Mathilde made her way from product manager in Paris to founding one of the hottest and fastest growing companies in the world of SaaS in the form of Front? 2.) What does Mathilde mean when she says, "I would choose discipline over vision any day of the week"? What does discipline really mean to Mathilde? Why is it a priority in the early days? How can a VC stress test and determine the level of discipline a founder has in first meetings? What are the signs or leading indicators? 3.) Communications: Investor Updates: What is Mathilde's biggest advice to founders when it comes to investor updates? What should they contain? How often should they go out? How should founders ask for help in updates? Where do founders often make mistakes? Revenue Updates: Why does Mathilde do revenue updates with the team? Is there a danger of being too transparent? What are the benefits of this transparency? What is the structure of the update? Who is privy to it? Direct Reports: How does Mathilde communicate with her direct reports? Why does Mathilde believe that CEOs should have their calendar public? What is the right cadence for these direct reports? 4.) How does Mathilde approach and think about fundraises with Front today? How can founders know when is the right time to raise? How does Mathilde think about building relationships with investors when she is not raising? How transparent should founders be when they are not raising? What are Mathilde tips for always overshooting her numbers? How does Mathilde conduct DD on potential investors in the company? Items Mentioned In Today’s Show: Mathilde’s Fave Book: The Power of Now: A Guide to Spiritual Enlightenment As always you can follow Harry, The Twenty Minute VC and Mathilde on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jeff Housenbold is a Managing Partner @ Softbank Vision Fund, the leading and most influential firm in the venture space investing more than $93 billion in the businesses and technologies they believe will enable the next stage of the information revolution. To date, Jeff has backed the likes of OpenDoor, DoorDash, Wag, Clutter, Brandless and Katerra just to name a few. Prior to Softbank, Jeff spent 11 years as President and CEO @ Shutterfly, during his tenure the company enjoyed incredible growth with the growth of the team from 103 to 2,600 employees. In the past, Jeff has sat on the board of Caesers Entertainment (the world's largest casino entertainment company), Groupon and Chegg and is currently a member of the Board of Trustees of Carnegie Mellon University. In Today’s Episode You Will Learn: 1.) How Jeff made his way from being President and CEO of Shutterfly for 11 years to writing $200m-2Bn checks as Managing Partner @ Softbank Vision Fund? 2.) We have Wag on the small end and Uber on the high end, so how does Softbank think about portfolio construction and insertion point today? Blended, at what stage would Softbank like their capital to be most concentrated? Does Jeff believe that ownership is largely built on the first check or built over time? 3.) What does the internal investment-decision making process look like for Softbank? How does this decision-making process change when considering reserve allocation? How does Softbank think about and approach reserves given their later entry into companies? Given the size of check being written, what does diligence look like in the standard process for Softbank? 4.) Given the forthy pricing environment today, how does Jeff assess his own price sensitivity? Does this differ depending on the stage of entry? With many suggesting Softbank have extended the period of privatisation for companies, how does Jeff and the team think about liquidity? How does Jeff think about the future of secondaries for seed managers and angels? 5.) Question from Eric Wu @ Opendoor: How does Jeff think about and analyse the opportunity in fragmented categories? What is the bottoms up thought process to this thesis? Speaking of Opendoor, how does Jeff most like to work with the founders he backs? How does Jeff think about he allocates his time across the portfolio? Items Mentioned In Today’s Show: Jeff’s Fave Book: The Fountainhead Jeff’s Most Recent Investment: Katerra As always you can follow Harry, The Twenty Minute VC and Jeff on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Want to book your own travel and not have the admin team chasing you for every receipt? Take your business travel program to the next level with TravelPerk. They’ve built the world’s largest inventory of low-cost flights, hotels, airbnb, trains, cars, you name it, all in one gorgeous booking experience. AND they’re built for business. Book, manage, support, analyze, and optimize your business travel, all in one place. Add to this a support team made up of dedicated travel experts who deliver a 7-star experience around the clock, and you’re taking corporate travel out of the dark ages. 20VC listeners can score a free lounge pass to over 1200 airports for a whole year. Not only will you be able to add “company savior” to your email signature, but you can also enjoy the luxury of amazing airport lounges all over the world. Click here to find out more!

Jon Dishotsky is the Founder & CEO @ Starcity, the startup on a mission to make cities more affordable to everyone allowing you to live with great people in the city you love. To date, Jon has raised over $28m in funding for Starcity from the likes of Social Capital, Y Combinator, Bullpen Capital, NEA and Kima Ventures in Paris, just to name a few. Prior to founding Starcity, Jon did over 3M square feet of commercial real estate transactions for clients including Optimizely, Cruise Automation, Weebly, Zenefits and many more. Before that he spent 8 years at the prestigious Cushman & Wakefield. Jon is also an active angel investor with investments in the likes of Remote, Fond and Savvy. In Today’s Episode You Will Learn: 1.) How Jon made his way from doing real estate transactions for clients including YC to being one of the hottest prop tech startups making cities affordable with Starcity? 2.) Why did it take so long for the venture ecosystem to get excited by the rise of proptech? What was the catalyst? When advising VCs, how do you advise them to get comfortable investing in these heavy asset, non-lean startup businesses? What are the biggest mistakes investors make when analysing proptech? 3.) What were some of Jon's biggest takeaways from his time at YC? How does Jon advise other founders looking to get into YC today? When it comes to investor selection, in what cases would Jon take a lower valuation against other offers? How does Jon advise founders on investor selection? What questions should they ask? Why is it like hiring? What are the common mistakes that Jon sees founders make when selecting investors? 4.) How does Jon advise founders when it comes to improving the quality of their mental health? Where do Jon struggle? How does Jon engage with social media knowing the psychological effects it has? What have been some major breakthroughs for him? Why does Jon believe having kids has made him a better founder? Why does Jon believe that older entrepreneurs are actually more successful than younger founders? 5.) What is Jon's biggest advice to founders when it comes to building relationships with VCs? Should founders "always be raising"? How transparent should founders be with VCs both in the relationship building process and the fundraise itself? As always you can follow Harry, The Twenty Minute VC and Jon on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Mamoon Hamid is a Partner @ Kleiner Perkins, one of Silicon Valley's most prestigious venture firms counting Google, Airbnb, Amazon, Spotify, Square and many more $Bn companies among their portfolio. As for Mamoon, he has invested in and served on the boards of some of the most innovative software companies of recent times including Box, Figma, Intercom, Netskope, Slack and Yammer. Prior to joining Kleiner Perkins, Mamoon was a Co-Founder and General Partner at Social Capital and before that Mamoon was a Partner at U.S. Venture Partners (USVP), where he spent six years. In Today’s Episode You Will Learn: 1.) How did Mamoon make the transition from electrical engineer to VC and how did that translate to his role today as Partner @ KPCB? 2.) With Kleiner's new $600m early stage fund, Mamoon had a blank canvas, how does Mamoon think about portfolio construction from a bottom-up perspective? Why is that strategy optimal? How important does Mamoon believe it is for VCs to have a sector focus today? What does he mean when he says, "VCs need to have both majors and minors"? 3.) In today's heated early stage ecosystem, how does Mamoon analyse and reflect on his own price sensitivity? What deal has changed the way he thought about price and he either regrets not paying it or is thrilled he did pay it? How does Mamoon feel about the compressed fundraising timelines we are seeing today? Is this a concern? 4.) How does KPCB think about reserve allocation with the new $600m fund? How do they approach the opportunity cost of dollar deployment in terms of when to stop following on? How does the investment decision-making process change when comparing initial to reserve investment? 5.) Where does Mamoon believe that founders need the most help from their venture investors? Where does Mamoon see the commonalities in founders struggles to scale themselves with their role? What are the biggest mistakes Mamoon sees being made when initial traction has been hit and they start to scale? How can founders avoid these? 6.) How does Mamoon think about and address what it takes to build the most successful and efficient venture partnership? How does Mamoon compare this to a basketball team? Is venture really a team sport today? what are some of the biggest challenges in scaling venture firms over time? Items Mentioned In Today’s Show: Mamoon’s Fave Book: Principles: Life and Work by Ray Dalio Mamoon’s Most Recent Investment: Viz.ai As always you can follow Harry, The Twenty Minute VC and Mamoon on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Michele Romanow is the Founder & CEO @ Clearbanc, the startup that provides entrepreneurs capital to grow without giving up a piece of their company. In 2019 alone, Clearbanc plans to invest $1B in 2,000 companies. To fund these ambitious plans, they have backing from some of the best in the business including Founders Fund, Santi @ Emergence, Social Capital, Precursor Ventures and Y Combinator just to name a few. As for Michele, prior to Clearbanc, she founded SnapSaves, a leading mobile savings platform that was acquired by Groupon. Before Snapsaves, Michele founded Buytopia, one of Canada’s leading e-commerce companies with over 2.5m customers. If that was not enough Michele is also a Dragon on Dragons Den Canada, the youngest dragon ever. In Today’s Episode You Will Learn: 1.) How Michele made her way from serial entrepreneur with exits to Groupon and being a Dragon on Dragons Den to changing the way we fund today's businesses with Clearbanc? 2.) Why does Michele fundamentally believe we need to rethink the way we fund our businesses? Why does giving away equity to buy FC and Google ads not make sense? What is the solution? What types of business with what types of revenue does this work for? Why does Michele believe we need to fundamentally stop celebrating fundraisings? 3.) So if Clearbanc lends on repeatable revenue from Google and Facebook, how does Michele think about the volatility of CACs we see as businesses progress? Is Michele concerned by the large incumbents pushing up CACs on traditional platforms? Investors can also be wise strategic advisors, how does Michele think about the potential loss of these advisors and board members with an alternative financing mechanism? 4.) From Clearbanc's data, what have been the big learnings on how venture is currently distributed across the US? To what extent does Michele believe that unconscious bias pervades into the decision-making of much of venture? What have Clearbanc discovered in terms of the diversity of the founders they back, purely through objective data analysis of their businesses? 5.) How does Michele respond when shit hits the fan? What is her coping mechanism? How would Michele advise young founders today in coping with tough times? What were Michele's lessons from her first sturgeon caviar business not being a success? Items Mentioned In Today’s Show: Michele’s Fave Book: Little Black Stretchy Pants As always you can follow Harry, The Twenty Minute VC and Michele on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Want to book your own travel and not have the admin team chasing you for every receipt? Take your business travel program to the next level with TravelPerk. They’ve built the world’s largest inventory of low-cost flights, hotels, airbnb, trains, cars, you name it, all in one gorgeous booking experience. AND they’re built for business. Book, manage, support, analyze, and optimize your business travel, all in one place. Add to this a support team made up of dedicated travel experts who deliver a 7-star experience around the clock, and you’re taking corporate travel out of the dark ages. 20VC listeners can score a free lounge pass to over 1200 airports for a whole year. Not only will you be able to add “company savior” to your email signature, but you can also enjoy the luxury of amazing airport lounges all over the world. Click here to find out more!

Brendan Wallace is the Co-Founder and Managing Partner @ Fifth Wall, the fund with the core thesis being the physical world around us is colliding with technology. Within their portfolio is the likes of Lime, OpenDoor, Clutter, ClassPass, Lyric and Hippo just to name a few. As for Brendan, before co-founding Fifth Wall he co-founded Identified, a data & analytics company focused on workforce optimization that was acquired by Workday in 2014. Prior to that, Brendan co-founded Cabify, the largest ridesharing service in Latin America. If that was not enough, Brendan has been an active angel investor having led over 60 angel investments including Bonobos, Dollar Shave Club, Lyft, SpaceX, Clutter, Philz Coffee and Zenefits. In Today’s Episode You Will Learn: 1.) How Brendan made his way from founding the largest ridesharing platform in Latin America to changing the face of early stage real estate and consumer retail investing with Fifth Wall? 2.) What is really going on in retail today? Is "retail apocalypse" a fair term to give to the landscape today? What formats does physical retail no longer work for? What is it perfect for? How does Brendan think about the distribution of physical retail for emerging brands? Will they need 1,000s of stores or is the 1,000 store brand era over? 3.) Why do digitally native brands fundamentally need retail? How much of consumer US spend relies on physical retail still today? When do these DNVB's need to expand into physical retail? From speaking to DNVB CEO's what are the most common challenges they face when making the expansion? 4.) How does expanding into physical retail change the game in terms of customer acquisition for DNVBs? At what point do DNVBs hit the invisible asymptote where acquiring customers through traditional online channels is no longer efficient? How have Amazon impacted the CACs for DNVBs in recent years? 5.) Given the consumer retail focus of the fund, one would expect a lower loss ratio, is it right to assume the lower loss ratio? How does Brendan think about portfolio construction with the fund? How does reserve allocation differ when investing in physical retail vs pure software plays? Is Brendan concerned by the lack of downstream capital in the physical retail space? 6.) How does Brendan assess outcome potential when comparing physical retail to pure software plays? Why des Brendan believe we will see a ton of intermediate outcomes? How does this change the type of entrepreneur that Brendan looks to back with the retail fund? Items Mentioned In Today’s Show: Brendan’s Fave Book: The Great Gatsby Brendan’s Most Recent Investment: Heyday As always you can follow Harry, The Twenty Minute VC and Brendan on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Want to book your own travel and not have the admin team chasing you for every receipt? Take your business travel program to the next level with TravelPerk. They’ve built the world’s largest inventory of low-cost flights, hotels, airbnb, trains, cars, you name it, all in one gorgeous booking experience. AND they’re built for business. Book, manage, support, analyze, and optimize your business travel, all in one place. Add to this a support team made up of dedicated travel experts who deliver a 7-star experience around the clock, and you’re taking corporate travel out of the dark ages. 20VC listeners can score a free lounge pass to over 1200 airports for a whole year. Not only will you be able to add “company savior” to your email signature, but you can also enjoy the luxury of amazing airport lounges all over the world. Click here to find out more!

Frederic Kerrest is the Founder & COO @ Okta, the independent and neutral platform that securely connects the right people to the right technologies at the right time. To date Frederic has raised over $415m with Okta from some of the best in the business including Doug Leone @ Sequoia, Marc Andreessen @ a16z, a dear friend of the show in Mike Maples @ Floodgate, Aneel Bhusri @ Greylock and Vinod Khosla, just to name a few. Okta IPO'd in April 2017 at a stock price of $17, today they sit at $102. Before founding Okta, Frederic enjoyed roles with Hummer Winblad on the other side of the table as a VC and also at Salesforce and Sun Microsystems on the operations side. In Today’s Episode You Will Learn: 1.) How Frederic came to found the now public Okta having spent time with Salesforce, Sun Microsystems and Hummer Winblad as a VC? 2.) What about an idea makes it worth pursuing and investing in? Does Frederic agree with the advice he was given, "it is 70% market, 20% people and 10% product"? When evaluating a market, what characteristics make for the most attractive markets? How does Frederic think about insertion points into markets? How does he evaluate market adjacencies? Why is it so good to be a monopolist in a small market? 3.) What were some of the hardest times Okta went through? How does Frederic determine the balance between vision and realism? How does Frederic as the leader personally deal with these challenging times? How can a founder determine from their hiring process whether they have product-market fit? What were the key turnings points that contributed to Okta's success? What did you have to get right to keep scaling? 4.) A little birdy told me there was an amazing story behind the a16z investment, what is that story? How did Frederic meet Marc and Ben and how did his relationship with them evolve over time? When analysing his investor base, where did each add real strategic value? What advice does Frederic give to founders today on the theme of investor selection? What should the core considerations be? Items Mentioned In Today’s Show: Frederic’s Fave Book: Battle Cry of Freedom: The Civil War Era As always you can follow Harry, The Twenty Minute VC and Frederic on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Sarah Smith is a Partner @ Bain Capital Ventures, a leading US venture fund with a portfolio that includes the likes of LinkedIn, Lime, SendGrid, Jet.com and more incredible companies. As for Sarah, what a start she has had to her time at Bain leading investments in the likes Perksy and the unicorn that is Lime. Prior to joining Bain, Sarah spent 5 years at Quora both as VP of Advertising Sales and Operations and then also from 2012-2016 as VP of HR, Recruiting, and Operations scaling the company from 40 to 200 employees. Before Quora, Sarah spent 4 years at Facebook as Director of Online Operations where her team scaled revenue to $1 billion ARR while reducing churn and increasing customer satisfaction. In Today’s Episode You Will Learn: 1.) How Sarah made her way into the world of venture having seen the hyper-growth of both Facebook and Quora over 9 years in operations? What were the biggest takeaways from her time with Facebook and Quora? What lessons did Sarah learn as an elementary school music teacher that she has applied to her role in VC? 2.) Sarah and Bain led the Series D in Lime, so how does Sarah think about: Market Size: How did Sarah think about and assess market size when evaluating Lime? How does Sarah respond to Peter Fenton's statement, "I always laugh when I hear investors say they look for big markets"? Competition: How did Sarah look to get comfortable entering such a fiercely competitive space? Is capital itself a defensible moat? Dilution: With such huge future funding requirements for these companies, how did Sarah get comfortable with the level of dilution that will surely occur? Hardware & Unit economics: How does Sarah think about and respond to the current level of break rates? How does Sarah believe Lime can have positive unit economics within 18 months? 3.) Why does Sarah believe that engineers are fundamentally underpaid? How does this tie into their mindset and attitude to equity? Why does Sarah believe the 4-year vesting schedule is fundamentally outdated? What would Sarah advise founders in terms of comp package to put in it's place? Does Sarah believe the high attrition rate in the valley is a feature or a bug? 4.) Why does Sarah believe it is glib to say the lack of equality is merely the problem of VC being an old boy club? What are the more foundational and systemic problems that have caused this inequality? Why does GP commit fundamentally inhibit diversity? For firms looking to add a female partner, what is their literal next step? What does that process look like? What can they do to ensure their success in the first year? Where does Sarah see many firms going wrong here? What must firms avoid? Items Mentioned In Today’s Show: Sarah’s Fave Book: Brotopia: Breaking Up the Boys' Club of Silicon Valley, The Making of a Manager: What to Do When Everyone Looks to You Sarah’s Most Recent Investment: Perksy As always you can follow Harry, The Twenty Minute VC and Sarah on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

David Rogier is the Founder & CEO @ Masterclass, the startup that brings you online classes taught by the world's greatest minds including Steve Martin, Natalie Portman, Margaret Attwood and more. To date, David has raised over $140m in funding for Masterclass from the likes of IVP, NEA, Javelin, Michael Dearing @ Harrison Metal, Atomico and past guests of the show Sam Lessin and Philip Krim. As for David, prior to founding Masterclass, he was on the other side of the table as an investor with Harrison Metal. Before venture, David spent time with IDEO helping to create new consumer products and brands. In Today’s Episode You Will Learn: 1.) How David made his way into the world of startups? How a lesson from his grandmother when he was only 7 shaped the type of company David wanted to build? 2.) David has previously said, "as a founder, you have one job". What is that job? How does David think about how raising VC changes outcomes? Why does David think many founders approach fundraising the wrong way? What questions must founders always ask a VC pre-term sheet? How can founders do their work and diligence on the VC? 3.) Why does David try at all costs to not send the deck to the VC ahead of meeting? Why can this be damaging? How can founders say no politely? Does David agree with the conventional wisdom that "founders must always be raising"? What is the optimal way to structure relationship building with investors? 4.) What does David mean when he says, "pick your investors as board members, not investors"? What does David believe makes the truly special board members? What were David's biggest learnings from Michael Dearing @ Harrison Metal when it comes to boards? What does David believe are big red flags in potential future board members? 5.) When validating the idea and the product, how does David think founders should use testing to prove their thesis at every stage of the business? Why, if proved, does this automatically secure your funding for the next round? What do VCs like to see in this testing? How does David think about when is the right time to go and raise big? Items Mentioned In Today’s Show: David’s Fave Book: Creativity Inc As always you can follow Harry, The Twenty Minute VC and David on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jeremy Liew is a Partner @ Lightspeed Venture Partners, one of the leading firms of the last decade with a portfolio including the likes of Snapchat, Mulesoft, Max Levchin’s Affirm, AppDynamics and many more incredible companies. As for Jeremy, he is best known for being the 1st investor in Snapchat and has also led investments in StitchFix, Affirm, Ripple, Giphy and Bonobos just to name a few. Previously, Jeremy was with AOL, first as SVP of corporate development and chief of staff to the CEO, and then as general manager of Netscape. Due to his incredible investing success, Jeremy has been featured on the Forbes Midas List multiple times. In Today’s Episode You Will Learn: 1.) How Jeremy made his way into the world of venture with Lightspeed and came to be one of the valley's leading consumer investors and minds? 2.) How does Jeremy think about and approach sourcing today? How has mindset on sourcing shifted over the last decade? For a new VC, what would Jeremy advise them in terms of building them benchmark for distinguishing between good and great? How does Jeremy distinguish between good and great? Who does Jeremy believe is the most naturally gifted sourcer and hunter he has worked with? 3.) What does Jeremy mean when he says, "it is more important to be right than contrarian"? From winning some of the hottest deals, what have been Jeremy's lessons on what it takes to win the most competitive? What does he mean when he says, "you have to find your home advantage"? Should investors spend time amplifying their strengths or improving their weaknesses? How does Jeremy think about the round compression timelines on hot deals today? How can investors and founders build relationships fast? 4.) Why does Jeremy believe that founder to VC engagement can be similar to a driving instructor and student? What are the biggest mistakes startups make when they hit initial traction and start to scale? WHat patterns has Jeremy seen? How can founders avoid them? 5.) How does Jeremy fundamentally structure his week and time? What time is devoted to internal meetings and partnership meetings? How much time is allocated to the existing portfolio? How much time is spent with new prospective companies? What is Jeremy's favourite and least favourite activities within the role? As always you can follow Harry, The Twenty Minute VC and Jeremy on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Dylan Field is the Founder & CEO @ Figma, the startup that provides a better way to design, prototype and collaborate, all in the browser. To date, Dylan has raised over $82m in funding from some of the world's best investors including Sequoia, Greylock, Kleiner Perkins, Founders Fund, Index Ventures and more. Prior to changing the world of design with Figma, Dylan held roles at Flipboard, Microsoft and LinkedIn and was part of the renowned Thiel Fellowship. In Today’s Episode You Will Learn: 1.) How Dylan made his way from Thiel fellow to changing the world of design and prototyping with Figma? 2.) What is the story behind the 4-year journey to the launch of their first product? How did Dylan maintain morale with such an extended window between creation and launch? What are the core challenges of building tools companies and getting initial traction? How did Dylan satiate VCs desire for fast growth with such a long period to launch? Is it possible to "go slow to go fast" with VC dollars? 3.) Sequoia led Figma's Series C, how did the round come together? What was it that made Dylan choose the lead investors for each of his rounds? How did this round compare to prior rounds led by Index, Kleiner and Greylock? How does Dylan advise founders to build relationships of trust and transparency with their VC in short period of time? 4.) How did Dylan approach the topic of board construction? What did he most want to get out of his board? What have been some of Dylan's biggest learnings when it comes to board management? What has Dylan found the most challenging element? 5.) As a young founder himself, where does Dylan see commonalities in the mistakes that other young founders make today? As a young founder, how has Dylan been able to hire A** talent execs? What have been some of the biggest learnings on team assembly and construction through the process? Items Mentioned In Today’s Show: Dylan’s Fave Book: Stronger, Faster, and More Beautiful As always you can follow Harry, The Twenty Minute VC and Dylan on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Dave Sobota is the Vice President of Corporate Development @ Instacart, the company that delivers your groceries in as little as 1 hour. To date the company has raised over $1.9Bn in funding from some of the very best investors and operators including Mike Moritz @ Sequoia, Jeff Jordan @ a16z, Aaron Levie @ Box, Sam Altman, Garry Tan and more incredible names. As for Dave, prior to Instacart, he was Director of Corporate Development @ Google for over 10 years and before that was with leading law firm, Wilson Sonsini. In Today’s Episode You Will Learn: 1.) How Dave made his way from the world of law to Director of Corporate Development at Google to his position at Instacart today? 2.) In 2016, we had 513 BC backed exits, 499 were M&A, so how does Dave assess the M&A landscape today? Why id Dave bullish on the future M&A environment, at least for the next 12 months? Where are his concerns around M&A clustering? How does Dave view the entrance of large scale PE into the tech M&A arena? 3.) From leading Google's M&A practice, what have been Dave's core learnings on whether an entrepreneur should sell their company or remain independent? Paul Graham once said, "startups only talk to corp dev when they are doing really well or really badly". Does Dave agree? What are the reasons a startup would not speak to corp dev? What is the right way for them to communicate this while leaving the door open for future conversations? 4.) How does Dave operationalise the tracking of the startup market and determine what startups he wants to meet? How does Dave like to and think about working with the VC community here? What does that relationship building process look like? In those early meetings, what are the core questions that founders must ask? How much of a role does price play for Dave when considering an acquisition? 5.) How can founders ensure when they sell their company, that it will be properly integrated? What answers from the acquirer suggest it will or will not be? From countless M&A processes, what do the best integrations look like post-acquisition? Where are mistakes often made? Does Dave agree with Paul Graham in stating it is a "gruelling" process? Items Mentioned In Today’s Show: Dave’s Fave Book: Lonesome Dove Dave’s Most Recent Acquisition: Tenor As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Henry Ward is the Founder & CEO @ Carta, the startup that helps private companies, public companies, and investors manage their cap tables, valuations, investments, and equity plans. To date, Henry has raised over $147m in funding from some of the industries leading investors in USV, Spark, K9 Ventures and Meritech and then also leading founders including Flexport's Ryan Petersen, Transferwise's Taavet Hinrikus and Slack's Stewart Butterfield. Prior to founding Carta, Henry was Founder of SecondSight, a portfolio optimization platform for retail investors. In Today’s Episode You Will Learn: 1.) How Henry made his way into the world of startups and came to found the gamechanger of cap tables and valuations with Carta? 2.) What does Henry mean by the term "executive half-life"? How does Henry determine between an exec that can scale with the company and an exec that cannot? What are the leading indicators? When weaknesses are revealed, how does this manifest itself? Does the exec open up and admit to it or does the leadership team have to be proactive? 3.) Question from Manu @ K9: As a first time CEO, what have been the biggest personal challenges for Henry in the scaling of himself? Why does Henry think it is unfair founders are given exemption from blame in scaling but execs are not? How does Henry make decisions differently now to the early days? What have been the improvements? 4.) How does Henry buck the conventional wisdom with his willingness to go after very small markets? What does the N of 1 vs 1of N rule mean here? Why does Henry believe the N of 1 markets is the most attractive? What are the core advantages to owning your market? How can founders think about insertion points? When is the right time to add additional products? How does Henry respond to the traditional notion of "focus"? 5.) Why does Henry believe most founders are afraid to put investors to work? If fundraising is, as Henry suggests "an auction process", what can founders do to optimise it? How does Henry approach the element of value creation and value extraction? How does this influence his approach to pricing? How does Henry think more tech founders can leverage acquiring services businesses and automating their processes over time? Where is the arbitrage in pricing here? Items Mentioned In Today’s Show: Henry’s Fave Book: The Essays of Warren Buffett: Lessons for Corporate America As always you can follow Harry, The Twenty Minute VC and Henry on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Dayna Grayson is a Partner @ NEA, one of the leading venture firms over the last 4 decades with a portfolio including the likes of Opendoor, Jet.com, Uber, WorkDay, Plaid, Box and many more incredible companies. As for Dayna, she has led the firm's investments in the likes of Desktop Metal, Formlabs, Onshape, Glamsquad, Framebridge and Curalate, just to name a few. Prior to joining NEA, Dayna was an investor at North Bridge Venture Partners where she championed companies including Camiant (acquired by Tekelec) and Tapjoy. Before venture Dayna was an engineer at Eye Response Technologies, later acquired by Dynavox Mayer-Johnson and also a product designer at Blackbaud (BLKB), the leading global provider of software to nonprofit organizations. In Today’s Episode You Will Learn: 1.) How Dayna made her way into the world of venture and came to be a Partner at NEA from her roots in product design and engineering? 2.) Sourcing: How does Dayna approach the sourcing component of venture today? What does the deck filtering process look like to Dayna, prior to meeting? What has Dayna found works best in really building rapport in the first meetings? What does the conviction building process look like for Dayna from there? If negative, how has Dayna found is the most effective way to say no? 3.) Decision-Making: How does Dayna think about optimising the investment decision-making process? How does Dayna balance between data vs gut? Does NEA require unanimous decision-making? Why does Dayna believe that at A or earlier, the price really does not matter? When does price really become a big issue? 4.) Evolution of Expectations: How does Dayna believe entrepreneurial expectations of VC has changed over the last decade. Where does Dayna believe investors can really provide the most value? Which board member has been the most impressive to Dayna when sitting alongside them on the board? Why? Items Mentioned In Today’s Show: Dayna’s Fave Book: Dopesick: Dealers, Doctors and the Drug Company that Addicted America Dayna's Most Recent Investment: WhireWheel As always you can follow Harry, The Twenty Minute VC and Dayna on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jeff Russakow is the CEO @ Boosted, the startup producing vehicle grade electric skateboards rethinking how we travel. To date, they have raised $74m in funding from the likes of Khosla Ventures, iNovia Capital, Andreessen Horowitz and our friends at Initialized. Prior to Boosted, Jeff was CEO @ Gimbal where he doubled revenue in his first year and added 80 new enterprise clients. Before that, Jeff was the CEO @ Findly where he grew the company to 450 employees and 20m end users. Jeff also enjoyed prior roles with the likes of Symantec, Adobe, SAP and Yahoo. In Today’s Episode You Will Learn: 1.) How Jeff made his way from leading enterprise CEO to re-thinking the way we travel today as CEO of Boosted? 2.) How does Jeff analyse the current sentiment to fundraising in the valley, specifically with regards to business construction? How has Jeff seen the investor class fundamentally transition over the last 20 years? When approaching investor selection, what is the 1 question that Jeff always asks? Where do founders often make mistakes here? 3.) Having raised the $60m round in 2018, how does Jeff approach the theme of capital efficiency today with Boosted? How does Jeff determine when is the right time to pour fuel on the fire? Why is Series B often the most challenging phase when considering the focus on unit economics and vision simultaneously? 4.) What is Jeff's gut reaction to the statement, "hardware is hard"? Why does Jeff feel this to be a glib statement that misses the point? How does Jeff respond to the criticism of the commodity element of hard, easy to replicate and copy? How would Jeff like to see the investor class change their mindset to hardware? What is the right way to approach it? 5.) What are the core elements required for a successful CEO transition? For a potentially incoming CEO, what must they be wary of with regards to the information conveyed to them by investors of the company? Where has Jeff seen many go wrong in CEO transitions? What can the founders do to make this process as smooth as possible? Items Mentioned In Today’s Show: Jeff’s Fave Book: The Missing Piece  As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Garry Tan is the Co-Founder and Managing Partner @ Initialized Capital, one of the West Coast's leading early-stage funds with a portfolio including the likes of Coinbase, Instacart, Cruise, Flexport and Opendoor, just to name a few. As for Garry, before co-founding Initialized, he was a partner at Y Combinator for nearly five years where he advised and funded over 600 companies. He was also co-founder of YC-backed blog platform Posterous (acquired by Twitter in 2012). Before that he was employee #10 at Palantir, where he was a founding member of the engineering team for Palantir's financial analysis product, and also fun fact, Garry designed Palantir's logo. In Today’s Episode You Will Learn: 1.) How Garry made his way from Founder and YC Partner to managing over $500m AUM today with his leading of Initialized? How did Garry's investment mindset change with the transition from angel to an institutional investor? 2.) What does Garry believe is the one thing pre-seed and seed investors must do that is more important than anything else? What relationship to the very best founders have with failure? How do they think about and approach it? How has Garry seen his own conviction building process in founders change over time? How does Garry approach the turning down of opportunities? What is the right way to deliver that feedback? 3.) Ownership: Initialized's funds have scaled from Fund I being $7m to Fund 4 being $225m, how have their ownership requirements changed with the evolution of their fund size? How does Garry think about collaboration and co-opetition with others funds as a result? What are the core challenges here? 4.) Price Sensitivity: With the larger fund and slightly more flexibility, how does Garry evaluate his own price sensitivity? What deal has Garry passed on due to price and it has stuck with him and taught him a valuable lesson? On pricing, how does Garry and Initialized approach reserve allocation? 5.) Investment Decision-Making: Garry has previously said "decision-making is a differentiator", what do Initialized do to ensure the highest quality of internal discussion and decision-making? How do they approach unanimous vs single partner decision-making? How does Initialized approach internal attribution with this in mind? Items Mentioned In Today’s Show: Garry’s Fave Book: Peter Thiel's Zero To One, Paul Graham's Hackers and Painters Garry’s Most Recent Investment: Standard Cognition As always you can follow Harry, The Twenty Minute VC and Garry on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Joel Gascoigne is the Co-Founder & CEO @ Buffer, the social media management tool that makes it easy for businesses and marketing teams to schedule posts, analyze performance, and manage all their accounts in one place. They had raised both seed and Series A rounds but last summer, spent $3.3m to buy out the majority of their Series A investors, making them much more independent. Joel now runs Buffer as a profitable business with $2m in profit in 2017 and $3m in 2018. Before co-founding Buffer, Joel co-founded OnePage and StartupMill and was a web developer in the UK. In Today’s Episode You Will Learn: 1.) How Joel made his way from web developer in the UK to founder of Buffer, in 2018 a business that did $3m in profit? 2.) What does Joel mean when he says that "fundraising is a bigger decision than most people realise"? At what moments does Joel believe that the founders are no longer the boss? When did Joel feel he was no longer the boss? What does Joel wish founders knew more about the VC process and mechanics? What questions must they ask VCs? 3.) Would Joel agree with Anand Sanwal, previously on the show that "VCs foie-gras their startups", forcing synthetic growth? What is the right way for founders to respond to this pressure? How did Joel personally handle the pressure? How does Joel assess and analyse the current VC ecosystem? What would he most like to change? 4.) There was a time when individuals did not want Joel to be CEO, how did Joel deal with that? What would Joel advise founders in the same position? What are the right steps to take? Joel then lost his co-founder, how was that process for Joel? What does he know now that he wishes he had known at the beginning of that process? How does he look to retain that level of support and guidance from someone other than a co-founder? 5.) What does Joel mean when he says, "leaders must lean into transparency"? Are there any limitations to being overly transparent? Now as a profitable company, how does Joel think about profit sharing with the team? What does profitable status allow the team to achieve and do that is not normally possible for VC backed co's? Items Mentioned In Today’s Show: Joel’s Fave Book: A Little Life As always you can follow Harry, The Twenty Minute VC and Joel on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Alex Clayton is a Partner @ Spark Capital, one of the leading firms of the last decade with a portfolio including the likes of Slack, Postmates, Oculus, Cruise, Twitter, the list goes on. As for Alex, he co-led Spark's investments in Pendo and Outreach and then led Spark's investments in Justworks, Braze (Appboy) and JFrog. Before Spark, Alex spent three years at Redpoint Ventures as a senior associate where he sourced or was actively involved in the firm's investments in Duo Security, JustWorks, RelateIQ (Salesforce.com), Infer, Lifesize and Sourcegraph. Prior to joining Redpoint, Alex was in the TMT investment-banking division of Goldman Sachs where he worked with Intuit, Yelp, SanDisk, and others. Fun fact, in the past Alex played on the ATP World Tennis Tour, competing in the U.S. Open and many other ATP events. In Today’s Episode You Will Learn: 1.) How Alex made his way from the world of investment banking with Goldman Sachs to one of the valley rising stars in the world of enterprise investing? What were Alex's biggest takeaways from his time at Redpoint and working with Tom Tunguz? 2.) How does Alex think about and approach sourcing today? How does Alex find most of his deals? How does Alex breakdown both thesis and network driven sourcing? How does sourcing at growth differ to sourcing at the early stage? If Alex has to meet founders when they are not raising, what does Alex advise founders who are told that you should not "always be raising"? 3.) How does Alex think about market sizing and evaluation today? What does he mean when he says he closely examines "market depth"? How does Alex determine whether a company has the ability to scale from a niche into a much larger TAM? What are the risks Alex is willing vs not willing to take when it comes to market? 4.) How does Alex think about competitor analysis when evaluating an opportunity today? In a world of almost infinite capital, does Alex believe that cash alone is a significant moat for competition? In customer calls when they discuss competition, what excites Alex to hear? How does Alex structure those customer reference calls? 5.) Alex has studied some of the best in class when it comes to SaaS, what do the best in class look like when it comes to: 1.) Quota attainment. 2.) Payback period. 3.) Net dollar retention and churn? 4.) Capital efficiency? Growth rate? Ultimately, what does Alex believe that it takes to go public having studied so many S1s? Items Mentioned In Today’s Show: Alex’s Fave Book: Zero to One by Peter Thiel Alex’s Most Recent Investment: Braze As always you can follow Harry, The Twenty Minute VC and Alex on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Mike Hirshland is the Co-founder of Resolute Ventures, one of the leading pre-seed and seed stage funds of the last decade having recently announced their new $75m Fund IV. In prior funds they have the likes of OpenDoor, Mixmax, Greenhouse, AppZen and more incredible companies. As for Mike, prior to founding Resolute, he founded Dogpatch Labs, the community which helped launch over 350 companies including Instagram. Before Dogpatch, Mike was a partner with Polaris Venture Partners from 1999-2011, where he was the original seed investor behind Automattic, Q1 Labs (acquired by IBM for $600 million), Quantcast and KISSmetrics. In Today’s Episode You Will Learn: 1.) How Mike made his way from a legal clerk in the US Supreme Court to founding his own venture firm in the form of Resolute Ventures? 2.) What does Mike mean when he says Resolute invest at the "old seed stage?" What stage of development and traction are the companies at this stage? Why does seed investing out of a $Bn fund not make sense to Mike? What are the acceptable vs unacceptable risks at this stage? 3.) How does Mike think and assess portfolio construction today? How many lines in the portfolio is enough to be sufficiently diversified? How does Mike think about ownership given his thesis on diversification? How does Mike assess his own price sensitivity today? How does Mike think about loss ratio within the portfolio today? 4.) What are the ideal attributes of the founder/VC relationship to Mike? Is it right for the investor to also be friends with their founders? What can founders do to really build and deepen relationships with investors both during and outside of official fundraises? Where does Mike often see founders making mistakes here? 5.) How does Mike think about the right time to establish a board? What does Mike advise founders in terms of board composition in the early days? How does Mike look to build a sense of "board intimacy" with his founders? Why does Mike believe that there is a "counter-productivity to boards at seed"? Items Mentioned In Today’s Show: Mike’s Fave Book: A Little Life As always you can follow Harry, The Twenty Minute VC and Mike on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Adam Pritzker is the Chairman & CEO @ Assembled Brands, a holding company providing working capital and financial services to emerging brands. In October 2018, they raised $100m in development capital from the prestigious Oaktree Capital Management. As for Adam, he is also a co-founder of General Assembly where during his tenure, prior to its acquisition by Addecco Group, he served as Chief Creative Officer, Chief Product Officer, and Chairman. For his entrepreneurial endeavors, Adam was featured in Forbes’ 30 Under 30, Vanity Fair’s The Next Establishment, Inc. Magazine’s 30 Under 30, and Business Insider’s Silicon Alley 100. In Today’s Episode You Will Learn: 1.) How Adam made his way into the world of startups with the co-founding of General Assembly and how that led to his founding Assembled Brands and financing the future of brands? 2.) Why is Adam optimistic about the current state of the consumer brand and retail environment? How does Adam respond to Alex Taussig @ Lightspeed's suggestion of the "re-platforming of retail"? How does Adam approach the changing demographic of consumer spend? What does this mean for both the brands and the channels they use to acquire customers? Does Adam believe we are in a consumer bubble today? 3.) How does Adam think about the lack of free and open distribution today for consumer companies? Are the traditional channels now too expensive to acquire customers on? How does Adam advise consumer founders on the saturation rate of marketing channels? How can they foresee the ceiling ahead of time? 4.) Adam has previously stated that Instagram is the new QVC, what did he mean by that? What type of consumer brand is Instagram best suited for? Why does Adam believe that in many cases the venture financing method is suboptimal and wrong for these scaling brands? What can founders who have taken VC funds and now seen it was potentially a mistake do? 5.) Why does Adam believe that the "infrastructure to power emerging brands is broken"? How can the current stack and infrastructure for brands be improved? What metrics should consumer founders really hone in on today? What sort of metrics suggests a brand is VC backable vs is not VC backable? How does Adam think about the ability of the consumer brand space to provide venture returns at scale? Items Mentioned In Today’s Show: Adam’s Fave Book: (1.) The Coddling of the American Mind: How Good Intentions and Bad Ideas Are Setting Up a Generation for Failure. (2.) The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It Adam's Most Recent Investment: Felix Gray  As always you can follow Harry, The Twenty Minute VC and Adam on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Victoria Treyger is a General Partner & Managing Director @ Felicis Ventures, one of the leading venture firms of the last decade backing 2 unicorns per year since founding including Shopify, OpenDoor, Flexport, Adyen, Twitch, Fitbit and many more. At Felicis, Victoria led the firm’s investments in prior 20VC guest Assaf Wand @ Hippo, Sentio, Sentilink, Blume, Floravere, and other stealth brands. Prior to joining Felicis, Victoria was Chief Revenue Officer of Kabbage. During her six-year tenure, Victoria and her team were instrumental in scaling revenue into the hundreds of millions of dollars and delivered a compound annual growth rate of over 100%. Victoria’s deep operating experience also includes leadership roles at Amazon, American Express, Travelocity, and RingCentral. In Today’s Episode You Will Learn: 1.) How Victoria made her way into the world of VC as GP @ Felicis today having scaled revenue into the 100s of millions with Kabbage on the operating side of the table? 2.) Having just made the move from the world of operations, what are the most surprising aspects of venture? What elements have you found to be the most challenging? How does Victoria think about what it takes to be the most effective coach? What can the investor do to build that level of trust and transparency with the founder? 3.) In terms of being a board member, how involved does Victoria think the board member should be? Who is the best board member Victoria has worked with? What made them so special? What are Victoria's biggest pieces of advice to founders when it comes to how to run an efficiency board? What is the right way for founders to think about board composition? 4.) What 3 trends in the world of consumer and CPG make Victoria so excited to be investing in the space today? What has fundamentally changed about the distribution of those products that changes the way we consume the products? Does this mean Victoria would disagree we are in a D2C bubble today? 5.) Speaking of distribution, how does Victoria respond to the suggestion "there is a lack of free and open distribution today" with customer acquisition costs being so expensive? How does Victoria think about the consumer and CPG space's ability to provide venture returns at scale moving forward? Items Mentioned In Today’s Show: Victoria’s Fave Book: Mindset: How You Can Fulfil Your Potential, Personal History Victoria’s Most Recent Investment: SentiLink As always you can follow Harry, The Twenty Minute VC and Victoria on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Austen Allred is the Founder & CEO @ Lambda School, a 9 month, immersive program that gives you the tools and training you need to launch your new career—from the comfort of your own home. As a Lambda student, you pay nothing until you’re earning $50k or more. And if you don’t, it’s free. To date, Austen has raised over $48m with Lambda from a personal favourite of mine Bedrock, GGV, GV, Stripe and Ashton Kutcher just to name a few. Prior to founding Lambda, Austen was Senior Manager for Growth @ LendUp and before that co-founded Grasswire. In Today’s Episode You Will Learn: 1.) How Austen made his way from being broke, sleeping in a car to founding one of Silicon Valley's hottest startups in the form of Lambda School? 2.) Austen lived in his car for many months in Palo Alto, what did Austen come to learn about himself from that experience? Before Austen has said, "it is not about money", so how would Austen describe his personal relationship to money? Consequently, what does this mean for Austen's relationship to risk? 3.) Austen previously stated he was "determined to never raise VC again before Lambda School". 2 years and $47m later, what changed in his attitude to raising VC? How mus every founder examine their business model before raising VC? What is the one question they must ask pre-raise? 4.) Austen recently raised a $30m Series B round, how did that round come about? What is Austen's biggest advice when it comes to investor selection? How does Austen think about when is the right time to raise big? How does that impact and affect operating mentality? What was it about Geoff Lewis that made Austen take his offer over others? 5.) Question from Geoff @ Bedrock: How does Austen iterate on all aspects of the business so fast? Why does Austen believe that the speed and quality of decisions are not mutually exclusive? Why does Austen believe the faster you ship, the higher quality they will be? How does Austen determine which experiments to stick with vs drop? Items Mentioned In Today’s Show: Austen’s Fave Book: Les Miserables, The Wright Brothers As always you can follow Harry, The Twenty Minute VC and Austen on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jeff Richards is Managing Partner @ GGV Capital, one of the leading venture firms of the last decade with a portfolio including the likes of Alibaba, Slack, Square, Xiaomi, Peloton, OpenDoor, just to name a few. As for Jeff, he sits on the board of or is an observer at BigCommerce, Brightwheel, Gladly, Lambda School, Namely and Tile just to name a few. Jeff also led GGV’s investments in Buddy Media (acquired by Salesforce), HotelTonight, Flipboard and has been actively involved in GGV’s investments in Opendoor, Domo, Square and Wish. Prior to joining GGV, Jeff founded two software companies: R4 (acquired by VeriSign), and QuantumShift, backed by Texas Pacific Group (TPG). In Today’s Episode You Will Learn: 1.) How Jeff made his way into the world of VC with GGV from founding and scaling 2 software companies in the 90s? What were Jeff's 2 biggest takeaways from having the company he founded raise over $100m then go to $0 in the crash? 2.) How does Jeff approach and see the transition from founder to CEO today? When does this transition need to occur? How do first-time founders differ compared to experienced serial entrepreneurs when it comes to building their teams? Where do they often struggle or make mistakes? What advice does Jeff offer them? 3.) Jeff has previously said, "do not raise for the highest valuation", what is his thinking here? What specific examples does Jeff have of why it can hurt and damage both the founder and the company? How does Jeff think about his own price sensitivity today? How does he determine when a stretch is a stretch too far? From backing the likes of Alibaba, Xiaomi and Didi, what were his biggest takeaways when it came to price? 4.) Decision-making is one of the only products venture has, how does Jeff and GGV approach decision-making as a firm today? Being a slightly later stage firm, how do they think about reserve allocation? What does the re-investment decision-making process look like? How does GGV think about attribution as a firm today? What are the benefits? 5.) What advice would Jeff give to an individual that has just entered VC? What does Jeff know now that he wishes he had known at the beginning? How does Jeff think about what it takes to be a truly special board member? What one or two things can a board member do to move the needle in their relationship with their founder? Items Mentioned In Today’s Show: Jeff’s Fave Book: In an Uncertain World: Tough Choices from Wall Street to Washington Jeff’s Most Recent Investment: Lambda School, Electric As always you can follow Harry, The Twenty Minute VC and Jeff on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Rob Sadow is the Founder & CEO @ Scoop, the startup that dramatically improves your commute providing convenient carpools with co-workers and neighbours. To date, Rob has raised over $37m in funding for Scoop from the likes of Danny Rimer @ Index, Brook Porter @ G2VP, Zaw Thet @ Signia Venture Partners and BMW i Ventures just to name a few. Before founding Scoop, Rob was a Manager @ Bain & Company and before that spent time in Israel with Better Place, working to provide electric vehicle networks to help accelerate the global transition to sustainable transportation. In Today’s Episode You Will Learn: 1.) How Rob made his way from the world of consulting and Bain to founding the future of convenient commutes with Scoop? 2.) How does Rob approach key decisions? What does Brook Porter @ G2VP mean when he says, "from a first principles perspective"? How does Rob determine when to make decisions with the head or the heart? Does Rob agree with Fred Destin, "as a founder, decisions are never perfect, it is about batting average"? Where does Rob see many make mistakes when it comes to decision-making? 3.) How does Rob find the dynamics of working with his brother as his co-founder? What are some of the core challenges? How does one make it scale and how does the relationship need to change over time? What is Rob's biggest advice to others when thinking about the person they partner with? 4.) How does Rob think about board construction? What have been some of Rob's biggest lessons in really using your board to get the most out of them? What works well for this? What does not work? How can founders create this level of relationship with their board members? Should founders direct their ask to specific individuals when soliciting help from their board? 5.) Why does Rob believe that they have next to no attrition of employees at Scoop? What have been some of Rob's biggest lessons when it comes to both culture creation and maintenance? How does Rob think leaders can invest more in their employees? What does this look like? Where do many go wrong or misallocate? Items Mentioned In Today’s Show: Rob’s Fave Book: The Wheel of Time As always you can follow Harry, The Twenty Minute VC and Rob on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Frank Chen is a Partner @ Andreessen Horowitz, one of the world's most prestigious venture firms with a portfolio including the likes of Airbnb, Coinbase, Github, Lyft, Slack and many more incredible companies. As for Frank, prior to joining the world of venture, he was a VP of Products & UI Design at HP Software and before that held the same title at Opsware. Before that, even cooler, Frank was Director of Product Management @ Netscape where he led a cross-functional team that defined, shipped, and marketed Netscape's award-winning LDAP directory and security products.  In Today’s Episode You Will Learn: 1.) How Frank made the move from the world of operations with Opsware and HP to being a Partner at Andreessen Horowitz? 2.) How does Frank view the current state of play for AI and machine learning? How does the rise of automation shift the economy as we know it? What does it do to class distinctions? How does Frank view it's impact on the labour market? How does Frank think about the value of truly large datasets? Where is the asymptotic moment where the utility value of data is realised? 3.) With the rise of self-driving, how does Frank perceive the future of car ownership? Who will fundamentally own and operate the vehicles? Will it be a horizontal play or a vertical play? In terms of adoption, why is Frank negative towards a driver assisted transition phase and believe in a more binary transition? 4.) How does Frank perceive the rise of automation and self-driving cars impacting public infrastructure? How will the layout of our cities change over time? How does Frank believe urban real estate could be optimised in a more efficient manner? Which nations does Frank believe will be the first to innovate here? 5.) What is the most challenging element of Frank's position as Partner @ a16z? How does Frank think about the right way to say not to an entrepreneur? How does Frank look to scale the learning curve rapidly when investigating new industries? What are the challenges here? What advice would Frank give to someone looking to scale learning curves? Items Mentioned In Today’s Show: Frank’s Fave Book: The Chronicles of Narnia, The Lord of The Rings Frank’s Most Recent Investment: Branch As always you can follow Harry, The Twenty Minute VC and Frank on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Rahul Vohra is the Founder and CEO @ Superhuman, the fastest email experience in the world. Fun fact, users get through their inbox twice as fast — and many see Inbox Zero for the first time in years! To date, they have raised funds from our friends at Boldstart, First Round, John Collison, Sam Altman, Wayne Chang, Mike Ghaffery and Yes VC just to name a few. Previously, Rahul founded Rapportive, the first Gmail plugin to scale to millions of users. Rapportive was ultimately acquired by LinkedIn. In Today’s Episode You Will Learn: 1.) How did Rahul make his way into the world of startups with the founding of Rapportive and how did that transition to changing the world of email with Superhuman? 2.) What does Rahul mean when he says, "you can reverse engineer a process to get to product market fit"? What does Rahul believe is the defining metric which determines your "product market fit score"? What is Julie Supan's framework? How did Dropbox and Airbnb use it to increase their product market fit? How can founders implement it into their process? 3.) What can founders do to expand the customer base to include users that currently are "somewhat disappointed"? What are the right questions to ask? What do we do with this feedback? How do we further segment the user base? Why should we "disregard the users whereby the primary benefit of the product does not resonate"?  4.) How does Rahul approach product roadmap and prioritisation? How can founders ensure that continuous tracking and user feedback is engrained within the organisation? What tools does Rahul do to monitor and capture this? What are some of Rahul's biggest lessons from going through this painstaking process stage by stage?  5.) Finally on fundraising, what does Rahul mean when he says, "always be raising but never be actively raising"? What are the benefits of this? How can founders transition catch up coffee into fundraising subtly? How does Rahul feel about party rounds? What are the pros? What are the downsides? How does Rahul advise founders here? Items Mentioned In Today’s Show: Rahul’s Fave Book: The Art of Game Design As always you can follow Harry, The Twenty Minute VC and Rahul on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Steve Case is Chairman and CEO of Revolution with the mission being to establish themselves as the premier venture firm outside of Silicon Valley. On the other side of the table, Steve is recognised as one of America’s best-known and most accomplished entrepreneurs as the co-founder of America Online (AOL). Under his leadership, AOL was the first internet company to go public and became the world’s largest and most valuable internet company delivering an 11,616% return to shareholders. In 2000, Steve negotiated the largest merger in business history, bringing together AOL and Time Warner. Among many other achievements, in 2014, Steve was named a Presidential Ambassador for Global Entrepreneurship. Steve has also been a leading voice in shaping government policy and was instrumental in passing the JOBS (Jumpstart Our Business Startups) Act. Finally, Steve is also Chairman of the Case Foundation, where he and his wife, Jean, have invested in hundreds of organizations, initiatives and partnerships. In Today’s Episode You Will Learn: 1.) How Steve made his way into the world of technology with the founding of AOL in 1985 and how that led to his founding of Revolution and investing today in the "rise of the rest" today? 2.) Having sat on both sides of the table both as founder and VC, what does Steve thinks make the truly special VCs? How do they engage with entrepreneurs? How do they actively move the needle for their companies? How would he like to see VCs of the future change and adapt their ways? 3.) How does Steve think about market timing when investing today? What were some of Steve's biggest lessons from seeing the dot com bubble and 2008 in both the role of entrepreneur and investor? What does he mean when he says, 'it can be dangerous to have a depression mentality' when investing? 4.) How does Steve analyse and assess the current fundraising environment today? Why does Steve see an incredible opportunity in funding companies outside the 3 traditional hubs of Silicon Valley, NYC and Boston? What needs to happen to drive this equalisation of funding further? What would Steve like to see change? 5.) What does Steve think are the 3 seminal roles of the CEO? What does Steve mean when he says that the CEO 'must be a shock absorber for company morale'? How does Steve deal with s*** hit the fan moments? What are his coping mechanisms and how does he advise entrepreneurs on them? Items Mentioned In Today’s Show: Steve’s Fave Book: The Third Wave, Be Fearless: 5 Principles For A Life of Breakthroughs and Purpose As always you can follow Harry, The Twenty Minute VC and Steve on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Henrique Dubugas is the Founder & CEO @ Brex, the first corporate card for startups offering instant online application, no personal liability, and tailored rewards. In a staggering 2 years, Henrique has grown Brex to a $1.1Bn valuation having raised over $180m in funding from some of the best in the business including Peter Thiel, Max Levchin, Elad Gil, DST, Y Combinator and IVP just to name a few. As for Henrique, prior to founding Brex he founded Pagar.me, a payments solution that he sold in Sept 2016, a year that the platform processed over $1.5 billion in GMV. In Today’s Episode You Will Learn: 1.) How Henrique made his way from learning to code games in Brazil to starting a leading payment processor to founding one of the world's fastest growing B2B companies in Brex? 2.) How does Henrique think about hiring the very best people? How has that strategy shifted and changed over time? What is the best advice Henrique has been given on hiring? What interview questions does Henrique think are crucial to ask? What are leading indicators that an individual has the ability to scale with the company? 3.) Why does Henrique think it is wrong to down people for being "compensation motivated"? How does Henrique think about compensation structures? Should candidates have to take pay cuts to join startups? What have been some of Henrique's biggest learnings and challenges here? 4.) How does Henrique approach the current sentiment to fundraising in the valley today? Why does Henrique disagree with founders who have periods of not speaking to VCs? What does Henrique believe is the right way to build VC relationships? How does Henrique think about the right time to raise? What advice does Henrique have for founders when it comes to investor selection? 5.) How does Henrique think about his own personal development? Where would he personally like to improve and strengthen? What is he doing to make this happen? How has Henrique seen himself as CEO change over the last 2 years with Brex? What have been some of the challenges of scaling himself as CEO? Items Mentioned In Today’s Show: Henrique’s Fave Book: 7 Powers: The Foundations of Business Strategy As always you can follow Harry, The Twenty Minute VC and Henrique on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

David Cohen is the Founder and co-CEO of Techstars, the worldwide network that helps entrepreneurs succeed. To date, David has backed hundreds of startups including the likes of Uber, SendGrid, Twilio, ClassPass, PillPack and more. In total, these investments have gone on to create more than $80B in value. Prior to Techstars, David was a co-founder of Pinpoint Technologies which was acquired by ZOLL Medical Corporation in 1999. Later, David was the founder and CEO of earFeeder, a music service that was sold to SonicSwap. If that was not enough, David is also theco-author (with Brad Feld) of Do More Faster; Techstars Lessons to Accelerate Your Startup. In Today’s Episode You Will Learn: 1.) How David made his way from, his words "geeky hacker" to the founder of one of the world's largest accelerators, Techstars and investor in multiple unicorns? 2.) What does David mean when he says that when assessing founders he studies "the moment of integrity"? What does he want to see from founders in those moments? What are some potential red flags? If a negative response, what are the subsequent actions an investor must take in this situation? 3.) How does David think about the right time to establish a board? What are the benefits of establishing your board with the seed round? What does David believe is the key to highly efficient boards? How has David changed as a board member over the years? Why does David believe, when building a company, "you always have to have a pessimist in the room"? 4.) When negotiating deals, what does David mean when he says "the terms must match the story"? How does David determine between a bridge and a bridge to nowhere? What can investors do to protect themselves if the targets of the business are not met and they have an uncapped note in place? How should they communicate this? 5.) Techstars today invests in over 500 companies per year, how does David think about reserve allocation across the portfolio? How does David feel about stack ranking portfolio co's quarterly and concentrating capital accordingly? Why is this not effective? Why should seed and angel investing be an entirely different asset class to VC? Items Mentioned In Today’s Show: David’s Fave Book: The Soul of Money: Transforming Your Relationship with Money and Life David’s Most Recent Investment: Ordermark As always you can follow Harry, The Twenty Minute VC and David on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Anjney Midha is the Founder & CEO @ Ubiquity6, the startup that allows you to edit reality together, turning any location into a space for real-time, shared AR and VR experiences. To date, Anjney has raised over $38m in funding for Ubiquity6 from some of the very best in the business including Phin @ First Round, Mike Volpi @ Index and Mitch @ Benchmark. Prior to Ubiquity6, Anjney spent 4 years on the other side of the table as an investor @ Kleiner Perkins and then as Founding Partner @ KPCB Edge, Kleiner's program helping founders get off the ground in AR, VR and Computer Vision. In Today’s Episode You Will Learn: 1.) How Anjney made his way into the world of startups on the investing side of the table with Kleiner Perkins and how that transitioned to his founding of Ubiquity6? 2.) What does Anjney believe is structurally wrong with venture now more than ever? How does the extended period of privatisation affect emerging partners in venture firms? How does Anjney think the very best of investors think about and analyse history? Why does Anjney believe venture is the business of financing "creative hits"? 3.) What are the 3 structural impediments facing venture today? Why and how does Anjney believe we will see a new class of VC enter the space and be very successful? In what form could this take? How can they outcompete the current crop of VCs? What does Anjney mean when he discusses the "squishy middle" of VC? 4.) Anjney is backed by Index, Benchmark and First Round, what are the commonalities among those firms that make them so special? How do the very best of firms engage and build relationships with their entrepreneurs? How does Anjney believe that focus can be successfully applied to venture? What is the right way for VCs to evaluate themselves? 5.) What do VCs really want to know when they are approaching risk assessment with founders? What can founders do to mitigate risk when pitching to VCs? How do the very best founders attract the very best talent to their team? What are the commonalities? Where do some go wrong in building the optimal team? Items Mentioned In Today’s Show: Anjney’s Fave Book: Rainbows End As always you can follow Harry, The Twenty Minute VC and Anjney on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Sam Lessin is a Founding Partner @ Slow Ventures, one of the leading early-stage funds on the West Coast with a portfolio including the likes of Robinhood, Gusto, Pinterest, Casper, Postmates and many more incredible companies. Sam is also the Co-Founder & Co-CEO @ Fin Analytics, the startup that provides precision measurement and coaching for high-performance operations teams. Before founding Fin and Slow, Sam spent 4 years at Facebook as a VP of Product Management following their acquisition of his prior company, Drop.io. In Today’s Episode You Will Learn: 1.) How Sam made his way into the world of venture with the founding of Slow following the acquisition of his company and 4 years in product at Facebook? 2.) How does Sam think about the difference between investing small personal checks vs managing institutional funds? What is the subsequent effect on mindset when investing? How does one prevent an increased conservatism? What does Sam mean when he says "VC forces some businesses into existence and makes others hard to fund? 3.) Why does Sam believe that man + machine must have a symbiotic relationship in the future? What does this look like in reality? When comparing today to the industrial revolution, is Sam concerned by the increased rate of adoption today? What does this mean for different categories of work? Why does Sam believe we will need more philosophers? 4.) Why does Sam believe that too much emphasis in the world of crypto is placed on Dapps? Why is he concerned by Dapps? What are of crypto does Sam believe is most exciting and investable today? Does Sam agree with Elad Gil that we will see the re-centralisation of talent back to the valley with the scaling of crypto co's? 5.) On governments, why does Sam not believe that both local and national governments will allow scooter companies to become meaningfully profitable in the future? How does Sam think about the balance and trade-off between privacy and security that faces many governments today? Items Mentioned In Today’s Show: Sam’s Fave Book: Lessons of History Sam’s Most Recent Investment: Fetcher.ai As always you can follow Harry, The Twenty Minute VC and Sam on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Joel Flory is the Founder & CEO @ VSCO, the startup that allows you to take your photography to the next level, with the mission to help everybody fall in love with their own creativity. To date, Joel has raised over $70m in funding with VSCO from some of the best in the business including Accel, Glynn Capital Management and Goldcrest Investments. Prior to founding VSCO, Joel founded his own photography company which he ran successfully for 10 years. In Today’s Episode You Will Learn: 1.) How Joel made his way from photographer to one of San Francisco's hottest startup founders today? 2.) How does Joel approach the current sentiment and approach to fundraising? Why were Joel and his co-founder unable to raise in the early days? How does Joel approach the element of investor selection? Brand name or partner? How does Joel look to really build relationships with VCs in compressed timeframes? What is Joel's litmus test to determine if a VC is interested? What single value add can a VC provide that is most important? 3.) What does Joel mean when he says, "you have to align your business model with your mission?" How can one really determine if they are aligned? How does this alignment change and alter with scale? What was the thinking behind the shift to a subscription business with VSCO? Was Joel worried it would impact the valuation and change the valuation mechanism to a multiple of revenue assessment? 4.) What do the optimal leadership team dynamics look like to Joel? What has worked well for Joel in binding the leadership team together? What have been some of the biggest challenges? How does Joel think about cross-functional communication across the leadership team? 5.) How does Joel think about his personal development today? Where would he like to improve? Where is he already strong? With a family and company in hyper-growth, how does Joel think about attaining that work-life balance? What advice would he have for other here? How does Joel determine what to say yes vs no to? What are some tips and hacks to this? Items Mentioned In Today’s Show: Joel’s Fave Book: How To Talk So Kids Will Listen and Listen So Kids Will Talk  As always you can follow Harry, The Twenty Minute VC and Joel on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Are you thinking about life insurance in the new year? Ladder is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY. Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Josh Kopelman is Founder & Partner @ First Round, one of the world’s leading seed funds with a portfolio including the likes of Uber, Warby Parker, Flatiron Health, Square, HotelTonight, GOAT and more incredible companies. As for Josh, he founded First Round in 2004 to reinvent seed stage investing. Since he has invested in over 200 startups and been ranked 4th in Forbes Midas List and named one of the top ten ‘angel investors’ in the US by Newsweek magazine. Josh has previously sat on the boards of Flatiron Health, Clover Health, AppNexus and more.  In Today’s Episode You Will Learn: 1.) How Josh made his way into the wonderful world of venture from angel investing and what the inspiration behind the founding of First Round was? 2.) How does Josh think about price sensitivity today? What were his learnings from being priced out of the seed round for Twitter and Dropbox? How has Josh seen his relationship to price change over time? How did witnessing the boom and bust both as operator and investor affect his investing mentality today? 3.) How does Josh and First Round think about reserve allocation? How has their thinking changed and evolved over time? Does Josh believe that ownership is fundamentally built on first check? What does the investment decision-making process look like for reserves? In terms of allocation, how does Josh think about time allocation across portfolio? Spend it with the winners, they return the fund or the strugglers and save cents on the dollar? 4.) Josh has spent over 3,000 hours on boards, what have been some of the biggest inflection points that have changed the way he thinks about being a good board member? How has he seen his style and approach change over time? What advice would Josh give to an individual that has just gained their first institutional board seat? 5.) Why does Josh believe that we fundamentally neglect "the pick" today in startup world? Why does Josh believe a high degree of startup mortality begins at the pick (idea) stage? How do the very best founders aproach this stage? How should these founders approach picking their investors? What should they look for? What should they be wary of? 6.) Why does Josh want to be known as a better picker of partners than investments? How has Josh thought about the building ou of the first round partnership over time? If there was anything he would have done differently, what would it be? Why does Josh fundamentally disagree with attribution? How does Josh think about generational transition? What are the steps required to do it well? Items Mentioned In Today’s Show: Josh’s Fave Book: Thinking in Bets: Making Smarter Decisions When You Don't Have All the Facts As always you can follow Harry, The Twenty Minute VC and Joel on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Are you thinking about life insurance in the new year? Ladder is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY. Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Olof Mathé is the Founder & CEO @ Mixmax, the startup that provides powerful analytics, automation and enhancements for your outbound communications. In the past, Mixmax achieved the almost the impossible in SaaS, true viral growth and a $0 CAC. As a result, Olof has raised over $13m in funding from some dear friends of the show in the form of Jason @ SaaStr, Mike @ Harrison Metal, Mike @ Floodgate and Carl @ Creandum, to name a few. As for Olof, prior to Mixmax he led the team that built Inkling Habitat, now adopted by the world’s largest publishers and before that he was an entrepreneur and worked at Skype and McKinsey. In Today’s Episode You Will Learn: 1.) How Olof made his way from the world of McKinsey and Skype to changing the way we interact with our email today with Mixmax? 2.) What does Olof mean when he says that founders go through 3 stages of denial when scaling their team? How does Olof think about the right time to add certain roles? What have been some of his big learnings here? Where do people make mistakes in the timing of hires? How does Olof think about the transition from generalist to specialist with scale? 3.) Why does Olof believe that in the majority of cases, it is not optimal or possible for founders to hire through their network? What is the right way for founders to approach building candidate pipe? What is the right way for founders to engage with recruiters? What is required in the recruiter/founder relationship for it to be a success? 4.) Why does Olof get worried when he hears "they will grow into the role"? What are the core leading indicators that suggest someone has the ability to scale vs not scale with the role? How much time does one give an employee to provide value and show their ability in the team? How does Olof think about the right way to let someone go? 5.) What are the 3 interview questions that all founders must ask in the hiring process? What answers indicate a candidate that is best suited for the role and company? What are red flags to watch for both in their answer and tone? How has Olof changed his hiring style over the last few years with Mixmax? Items Mentioned In Today’s Show: Olof’s Fave Book: SPQR: A History of Ancient Rome As always you can follow Harry, The Twenty Minute VC and Olof on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Are you thinking about life insurance in the new year? Ladder is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY. Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Hunter Somerville is a Partner at Greenspring Associates, a leading venture firm and fund of funds. On the direct side their portfolio includes the likes of Sonos, App Annie, Docusign and Alibaba just to name a few. As for their fund investing, they have backed the likes of Accel, Founders Fund, Thrive, Lightspeed, Foundry Group and many more incredible managers. As for Hunter, he is actively involved in the assessment of micro-vc managers for the Firm where he sits on the LP advisory boards for the likes of Pear, Foundry Group, Scale Venture Partners and BullPen Capital just to name a few. Prior to joining Greenspring, Hunter worked as an Associate for Camden Private Capital. In Today’s Episode You Will Learn: 1.) How Hunter made his way into the world of fund investing and came to be a Partner @ Greenspring? 2.) How does Hunter assess the world of micro-VC today? Does Hunter think we will see the market start to shrink as LPs become over-allocated to the space? Why does Hunter believe the barriers for micro VCs to raise are lower than ever? What does this mean for the future of early stage? 3.) How does Hunter fundamentally approach the assessment of new funds? Is it all about track record? How does he look to build a framework/model to predict future performance? What makes Hunter sceptical when assessing new opportunities? Where do many managers go wrong in the fundraising process? How does Hunter think about loss ratio? 4.) As an LP having to allocate to multiple different stages, why does Hunter feel there is a shortage of dedicated A and B round funds? How does Hunter expect both reserve allocation and loss ration to alter as we move from early to later stage? How does Hunter feel about opportunity funds? How does Hunter and other LPs assess GP led restructurings? 5.) Why is Hunter bullish on the future for direct secondaries? Why does he believe this is fundamentally good for the ecosystem? How does Hunter think about early stage managers in their needs for early liquidity? To what extent will early stage managers need to navigate the private secondaries market to attain this liquidity? Items Mentioned In Today’s Show: Hunter’s Fave Book: Great Expectations by Charles Dickens Hunter’s Most Recent Investment: Amplify Partners As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Are you thinking about life insurance in the new year? Ladder. Is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY. Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Assaf Wand is the Founder & CEO @ Hippo, a new kind of insurance company that provides smart coverage for homeowners with a quote in just 60 seconds. To date, Assaf has raised over $109m in funding for Hippo from some dear friends of the show in the form of Felicis Ventures, GGV Capital, Fifth Wall, Zeev Ventures and Lennar just to name a few. Prior to re-imagining the world of insurance, Assaf founded Sabi, creating products that improve everyday life with superior functionality and design. Sabi was acquired by Urbio in 2015. Before that Assaf held numerous different roles including as a consultant at McKinsey and Investment Associate at Intel Capital. In Today’s Episode You Will Learn: 1.) How did Assaf being the worst employee in the world lead to his entrance into the world of early-stage startups and the founding of Hippo? 2.) How does Assaf analyse the current sentiment and approach to fundraising in the valley today? Why does Assaf believe that every company looks one round earlier than it should be for the VCs? How does Assaf think about investor selection? What is the single biggest value a VC partner can provide? Does Assaf agree that founders should "always be raising"? Why does Assaf believe that top funds should not get significant discounts? 3.) What does Assaf believe are the biggest mistakes entrepreneurs make when building their board? On boards, why does Assaf believe there is a danger that partners from top funds have their ideas overweighted due to the prestige of their fund? What can be done to prevent this? What does Assaf believe is the right screening process for new board members? 4.) What does Assaf believe separates the good from the great when it comes to board members? How does Assaf really look to building meaninful relationships with his board members? What has worked well? On the flip side, why does Assaf believe the No 1 element of a board is "do no harm"? Where can board members actually be damaging? 5.) Hippo is growing 30% MoM and will be in 80% of the US in the next 12 months, how does Assaf think about when is the right time to put the pedal to the metal? What are those leading indicators? Where do many founders go wrong here? Is it simply a case of whenunit economics work, one is ready to scale? Items Mentioned In Today’s Show: Assaf’s Fave Book: The Fountainhead, The Pillars of The Earth As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Are you thinking about life insurance in the new year? Ladder. Is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY. Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Fred Destin is a Founding Partner @ Stride.VC, one of Europe's newest seed funds with a portfolio including the likes of Cazoo and Forward Health. Over his 17 year career in venture, Fred has established himself as one of Europe's leading VCs with the exit value of 3 of his portfolio companies alone last year totalling more than $4.5Bn with PillPack's $1Bn sale to Amazon, Zoopla to Silverlake for $3Bn and Integral Ad Science to Vista for $850m. Fred has also led investments as a General Partner @ Accel in Deliveroo, the world leader of food on demand and Carwow, the number 1 for new car sales in the UK. In Today’s Episode You Will Learn: 1.) How Fred made his way into the world of venture and early stage? What was behind his decision to leave Accel to found Stride with Harry? 2.) Why does Fred think many today misunderstand "risk" in venture? How does that apply across the portfolio? Does Fred agree with Brian Singerman, "venture is a game of upside maximisation"? What risks does Fred define as acceptable vs non-acceptable risks? How does Fred really look to strength test the quality and depth of a founder pre-investment? What are the benefits of going through conflict early? 3.) How does Fred think about price sensitivity? What are the core questions a VC can ask when considering the pricing of an opportunity? How does Fred think about reserve allocation? How does Fred analogize this to the best traders? To what extent does TAM play a dominant role in Fred's evaluation? What does Fred mean when he says "we have to remember, we are the ones that get picked also"? 4.) How does Fred think about and assess innovation within venture? How does Fred perceive the role of data to impact venture over the coming years? Why does Fred believe it is exaggerated that data will disrupt the early stage in the coming years? Where would Fred like to see further innovation in the mechanics of venture? 5.) What does Fred believes separates the good from the great when it comes to board members? How can board members create an environment where the entrepreneur feels they can say all that is wrong? Where do many board members go wrong? Why are board members so wrong to bash a founder for missing their numbers? Why does Fred believe that plans are fiction? WHy is the framework of the plan what really matters? Items Mentioned In Today’s Show: Fred’s Fave Book: Man's Search for Meaning As always you can follow Harry, The Twenty Minute VC and Fred on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Are you thinking about life insurance in the new year? Ladder. Is the smart and easy way to get term life insurance online. With Ladder there are no commissioned agents and no policy fees — you can be done in minutes. Even better, coverage can start today, if you qualify, and you can cancel anytime. Ladder is licensed and backed by trusted partners, with billions in coverage. Visit ladderlife.com to apply and get an instant decision on fully underwritten term life insurance, and check life insurance off your list TODAY. Ready for tax season? Wishing you’d kept a closer eye on your books this year? Set yourself up for success in 2019 with Pilot. Pilot is a bookkeeping company focused on the needs of startups. Their team of SF-based bookkeepers are assisted by engineers to automate the most error-prone parts of bookkeeping, so you know you’re getting an accurate report every month. Plus, Pilot does accrual basis bookkeeping in Quickbooks Online, so you’re never locked into a proprietary platform. Learn more and sign up here. Don’t wait – the first 100 members of the Twenty Minute VC community get 20% off Pilot Core for six months.

Avi Meir is the Founder & CEO @ TravelPerk, the startup that allows you to book, manage and report all your business travel in one place. To date, Avi has raised over $73m with TravelPerk from the likes of Felix Capital, Yuri Milner, Spark Capital, Sunstone and LocalGlobe to name a few. Before founding TravelPerk, Avi founded HotelNinjas, a web-based hotel management software platform that was ultimately acquired by Booking.com. Prior to that, Avi was VP Product at Budgetplaces.com, which was acquired by Palamon in 2011. In Today’s Episode You Will Learn: 1.) How Avi made his way from the world of hotels to the world of founding startups and what was his entry point? How did Avi's experience with HotelNinja's impact his operating mindset with TravelPerk today? 2.) How does Avi think about attaining the right board composition? What is the ideal structure? How important is it to have industrial experience around the table? What are the 2 other core skills that Avi believes are required on the board? What can founders do to ensure plasticity of mindset at a board level? 3.) What makes the truly special board members? What do they do both in the good and the bad times to make them so good? What does Avi believe makes the more challenging board members to work with? Why does Avi believe that culture fit at the board level is not discussed enough? What can be done by the founder to improve this? 4.) TravelPerk has now raised over $75m in funding, what does Avi believe they have done well to date to allow them to raise this? For the next round, what would Avi like to improve upon and pushback on further? What advice does Avi have for founders entering negotiations when it comes to both valuation and option pool? 5.) Why does Avi believe that culture and growth are 2 sides of the same coin? What have been some of the biggest challenges in scaling the team with the scaling of the company? How does one retain startup culture when no longer a startup? What would Avi do differently with regards to expansion with the benefit of hindsight? Items Mentioned In Today’s Show: Avi’s Fave Book: Delivering Happiness: A Path to Profits, Passion and Purpose As always you can follow Harry, The Twenty Minute VC and Avi on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Scott Belsky is an executive, entrepreneur, author, and investor. He currently serves as Adobe's Chief Product Officer and Executive Vice President, Creative Cloud. Before Adobe, Scott co-founded Behance in 2006 and served as CEO until Adobe acquired Behance in 2012. Alongside his role at Adobe, Scott is a Venture Partner at one of the world's leading venture firms, Benchmark. Scott also actively advises and invests in startups personally having one of the most incredible angel portfolios with early checks in Pinterest, Uber, Periscope, Warby Parker, Carta, Flexport and more. Scott is also the author of Harry's favourite book of 2018, The Messy Middle. In Today’s Episode You Will Learn: 1.) How Scott made his way into the world of startups with Behance, how that translated to the world of angel investing and being Chief Product Officer @ Adobe? WHat does Scott mean when he discusses the correlation between utilisation and happiness? 2.) What does Scott mean when he says he looks for people whereby 'conversations improve by step function?" What are the best examples of this? How have they shown this? How does Scott think startups founders can manufacture motivation? How has Scott seen the best founders hire the very best team? How do the best founders determine between a stretch and a stretch too far? 3.) In terms of product, what does Scott mean when he refers to the "value of slow cooking"? How does that relate to product creation? Why does Scott often have issues with the MVP approach seen today? How does Scott think about the importance of product simplicity? How can one maintain that over time? Why does Scott believe more founders should spend more time crafting the last mile user experience than they do? 4.) Simplicity is great but VCs often suggest, non-defensible, how does Scott think about building defensibility with simplicity? Simplicity often also narrows market size, how does Scott think about and analyse market size today when investing? Where does Scott think many investors go wrong today when trying to measure market size? 5.) What does Scott mean when he says "resources are like carbs, resourcefulness is muscle"? Why does Scott believe we need to challenge our faith in the strength of resources? What advice does Scott given when founders ask, "when is the right time to raise big"? How has Scott's writing of the book influenced his mindset when engaging with founders today and investing? Items Mentioned In Today’s Show: Scott’s Fave Book: Endurance: Shackleton's Incredible Voyage to the Antarctic Scott’s Most Recent Investment: Assembled Brands As always you can follow Harry, The Twenty Minute VC and Scott on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Andrew Dudum is the Founder & CEO @ Hims, one of the fastest growing consumer brands of our time and the fastest growing men’s health and wellness brand. To date, they have raised over $97m in VC funding from some of the best in the business including Thrive, Founders Fund, Forerunner, IVP, Redpoint and SV Angel just to name a few. Andrew is also Venture Partner at Atomic, a venture-builder backed by Peter Thiel, Marc Andreesen and many of the world’s best investors who recently announced their new $150m fund to start companies solving the world’s problems. Prior to Atomic and Hims, Andrew led Product at TokBox.com, the leader in web-based communication and In 2012 TokBox was acquired by the global telecommunications company Telefonica ($TEF). In Today’s Episode You Will Learn: 1.) How Andrew made his way into the world of startups, came to build a venture builder backed by Thiel and Andreesen before starting the fastest growing men’s health and wellness brand in Hims? 2.) How does Andrew view the world of online and offline marketing in today’s proliferated D2C space? What were the core elements that allowed Hims to achieve such success with their branding? How does Andrew respond to suggestions that there is a lack of free and open distribution due to incumbents paying up for traditional channels making CAC unachievable for startups? How does Andrew look to solve for this? 3.) What does Andrew believe it is that has allowed Hims to execute faster than any other D2C brand in history? How does Andrew distinguish between people and process when considering the scaling at different stages of the business? What are the pros and cons of having such constraints on headcount? When is the right time to pour fuel on the fire? 4.) Hims raised their last round at a $200m valuation in less than a year of operating, how did Andrew evaluate this one? Does this not effectively price Hims out of the majority of M&A?  What leads Andrew’s thesis with his suggestion that he thought the valuation was “quite frankly, a great price for investors”? What advice would Andrew have for founders entering the fundraising process? 5.) Andrew is also the co-founder @ Atomic, so what really is a venture builder? How have Atomic built a framework around idea generation? How do Atomic determine which ideas to pursue and which to disregard? How does data and benchmarking play a central role in this process? Items Mentioned In Today’s Show: Andrew’s Fave Book: Creativity Inc As always you can follow Harry, The Twenty Minute VC and Andrew on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Much like how Carta changed how private companies manage their cap tables and 409A valuations, Carta are now doing the same for fund administration. With Carta’s new, modern fund administration software and services, you get a real-time dashboard of your general ledger, can securely share info with your LPs, and issue capital calls–from the same platform, you accept securities and request cap table access. So essentially, Carta simplifies how startups and investors manage equity, fund administration, and valuations. Go to carta.com/20VC to get 10% off.

Ted Wang is a Partner @ Cowboy Ventures, one of Silicon Valley's leading early-stage funds with the likes of Philz Coffee, Dollar Shave Club, Brandless, DocSend, Accompany and Brit + Co all in their portfolio. As for Ted, prior to VC, Ted spent X years as a leading Silicon Valley lawyer with Fenwick & West where he worked with some of the most notable companies of our times including Facebook, Dropbox, Twitter, Square and Spotify just to name a few. Ted also created the Series Seed Documents - a set of open-sourced financing documents posted on Github used by thousands around the world today. In Today’s Episode You Will Learn: 1.) How Ted made his way from one of the most renowned lawyers in the valley with Fenwick & West to partner @ Cowboy alongside Aileen Lee? 2.) How does Ted fundamentally approach risk today? Given this mindset, how does this impact Ted's thinking on optimizing portfolio construction? On the flip side, how has Ted seen many founders wrongly approach the theme of risk? What is the question they need to be asking? What is Ted's story about risk related to his time working with Jet? 3.) What is it that makes Ted believe that "advice is often oversimplified"? If so, how can VCs provide tangible advice to their portfolio companies today? How can founders determine what is the right advice to accept and integrate vs listen and disregard? How does this lead Ted's thinking on the 2 core value adds a VC can provide? What advice did Dropbox Founder, Drew Houston give Ted on when to accept advice? 4.) What does Ted mean when he says "there are 4 parts to venture"? How does Ted think about the theme of learning and self-improvement when assessing founders? How does he look to do this pre-investment? What questions reveal the most? Applying it to himself, where will Ted place his biggest efforts on learning within the realm of venture over the next 12 months? Items Mentioned In Today’s Show: Ted’s Fave Book: 7 Habits of Highly Effective People Ted’s Most Recent Investment: Fullcast As always you can follow Harry, The Twenty Minute VC and Ted on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC. Much like how Carta changed how private companies manage their cap tables and 409A valuations, Carta are now doing the same for fund administration. With Carta’s new, modern fund administration software and services, you get a real-time dashboard of your general ledger, can securely share info with your LPs, and issue capital calls–from the same platform, you accept securities and request cap table access. So essentially, Carta simplifies how startups and investors manage equity, fund administration, and valuations. Go to carta.com/20VC to get 10% off.

Dave Vasen is the Founder & CEO @ Brightwheel, the child management software solution you need and now the #1 platform for early education. To date, with Brightwheel, Dave has raised over $33m in funding from some of the best in the business including Bessemer, GGV Capital, Lowercase Capital, Chan Zuckerberg Initiative, our friends at Eniac Ventures and then the likes of Mark Cuban and Chris Sacca. As for Dave, prior to Brightwheel, he was a VP of Product @ AltSchool and before that spent 3 years at Amazon in numerous different roles including Head of K-12 Education on Kindle and developed and launched the “Made for Kindle” licensing program – both domestic and global. In Today’s Episode You Will Learn: 1.) How Dave made his way into the world of edtech and startups from being a consultant at Bain and product manager at Amazon? 2.) Why does Dave fundamentally disagree that founders should always be raising? What is the right way that founders should approach the fundraise? How can founders turn down investor meetings politely when requested and they are not raising? What is the right way to think about capital as a weapon today and the effective allocation of it? 3.) Why does Dave disagree with many elements that the Founder/VC relationship is a marriage? What one element, other than capital, does Dave most look for in a potential investor? What can founders do to really compress the fundraise timeline? How can founders build relationships with VCs under these compressed conditions? 4.) In the valley there is a large amount of glorification around the scaling and founding of companies, how does Dave feel personally about this glorification? How would Dave like to see this mindset fundamentally change? In terms of mindsets, why does Dave push back against the suggestion of VC "pattern recognition"? How has being an older founder and father changed the way he thinks about building Brightwheel today? 5.) How does Dave interpret the meaning of focus today with regards to company building? How does Dave determine the elements to really double down on? How does Dave think about saying no to opportunities? What framework does he use? What have been some of Dave's biggest learnings on culture and being prescriptive around it? Items Mentioned In Today’s Show: Dave’s Fave Book: The Five Dysfunctions of a Team: A Leadership Fable As always you can follow Harry, The Twenty Minute VC and Dave on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Anu Duggal is the Founding Partner @ Female Founders Fund, a leading early-stage fund investing in female-founded technology companies. Within their incredible portfolio is the likes of Zola, Rent The Runway, Maven Clinic, Tala and previous guest, Rockets of Awesome. They also have the most incredible mentor network including the founders of Stitchfix, Care.com, Zola and Tala. Prior to founding Female Founders Fund Anu was CEO @ Doonya, a dance fitness and media company inspired by Bollywood and fun fitness. Before that, Anu was Founder @ Exclusively.In where she headed up New Business Development. In Today’s Episode You Will Learn: 1.) How Anu made her way into the world of VC with her founding of Female Founders Fund? 2.) What does Anu mean when she says she likes to focus on "non-obvious opportunities"? What are some clear examples of this? These non-obvious opportunities often appear to have smaller markets, how does Anu think about market size and evolution when investing? Can one blame male VCs for sometimes not identifying with the problem set being solved? What can be done to solve this problem? 3.) What 3 elements do Anu most look for when investing in consumer today? How does Anu respond to the statement that consumer may produce healthy revenue but at the end of the day they will never really produce venture return and be sold for 1.6x EBITDA? How does Anu assess the state of the M&A market today in the world of CPGs? 4.) How was the first fundraising for Female Founders Fund? What did the process look like in terms of amount of meetings, total committed LPs and duration spent raising? What were the common pushbacks from LPs in the fundraise? What did Anu do well that she would do again? How did the raise of the 2nd fund compare to the raise of Fund I? 5.) What does Anu mean when she states, "the power of the female network"? How has Anu seen this work in the real world? How does this allow Anu to see the best deals? How does Anu think about scaling check size and ownership with fund II? How does Anu think about reserve allocation when re-investing? Items Mentioned In Today’s Show: Anu’s Fave Book: Educated: The international bestselling memoir Anu’s Most Recent Investment: Co-Star, Hyper-Personalized, Real Time Horoscopes As always you can follow Harry, The Twenty Minute VC and Anu on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Anand Sanwal is the Founder & CEO @ CB Insights, the tech market intelligence platform that ingests massive datasets, to answer complex questions and predict future trends. CB is the 9th best place to work in the US according to GlassDoor and one of the fastest growing SaaS companies in the US. To date, CB Insights has raised over $11m in VC funding, a topic Anand discusses at length in our episode today! Prior to founding CB, Anand held numerous roles at American Express including running a $50m Innovation Fund and managing the company's discretionary investment spend ($4-5Bn p.a.). Before American Express, Anand was one of the early team @ Kozmo.com, one of the most well-funded and infamous startups in NYC history. In Today’s Episode You Will Learn: 1.) How Anand came to found CB Insights from running American Express' $50m Innovation fund and the a-ha moment there? 2.) Why does Anand believe that revenue funding is the best kind of funding? What 3 elements does Anand believe it fundamentally allows? What does Anand mean when he says "most have 3 masters, you can only serve two of them at once"? Does Anand believe that founders today are treating their investors as customers? 3.) How does Anand distinguish between business that can be funded from revenue vs those that cannot? How does Anand think about the relationship between growth and margin? Why does it make sense for VCs today to push for the suggestion that startups need to raise big to grow? How can founders think about and respond to this? 4.) Why does Anand believe that most B2B content today is crap? What are the core pillars that make great B2B content today? How does Anand think about potentially going too far when it comes to the risque nature of the content? What advice would Anand give to B2B founders wanting to ramp up their game in content? Where do many go wrong? 5.) What does Anand mean when he says that "pedigree is often overrated"? How has that led Anand's thinking when building out the team at CB? Where does Anand see most founders make mistakes when it comes to both team and company scaling? What interview question does Anand find most revealing of an individuals' character? Items Mentioned In Today’s Show: Anand’s Fave Book: Influence: The Psychology of Persuasion As always you can follow Harry, The Twenty Minute VC and Anand on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Danny Rimer is a Partner @ Index Ventures, one of the world's leading venture funds with a portfolio including the likes of Dropbox, Skype, King, Bird, Slack and many more incredible companies. As for Danny, he is known for his investments in Dropbox, leading the company's Series B, Etsy, King (makers of world famous, Candy Crush), Skype and more recently many retail and fashion businesses such as Farfetch, Glossier and GOAT. He's been on the coveted Forbes Midas List for more than a decade and in 2017 was appointed an Officer of the Order of the British Empire (OBE) for services to business and charity and the New York Times included him in its list of the top 20 venture capitalists worldwide. In Today’s Episode You Will Learn: 1.) How Danny made his way into the world of venture and came to be a Partner @ Index Ventures? 2.) Having backed the likes of King, Skype, Glossier, how does Danny respond to Peter Fenton and Jeremy Levine's suggestions of a "consumer downturn"? Does Danny believe there is a lack of free and open distribution today? Can startups compete with such inflated CACs? Henry Davis @ Glossier asks: how have you seen acquisition models change over time? How do you envision acquisition models of the future? 3.) Peter Fenton said on the show previously, he always laughs when he hears VCs say they like big markets, how does Danny assess market sizing today? What have been Danny's biggest lessons on assessing market size when looking at his portfolio? How does Danny think about niche markets today in such an Amazon dominant world? How does Danny assess price today? How does Danny determine when to stretch vs stay firm? 4.) Having helped many companies scale to global success, what does Danny believe to be the core considerations in getting your startup ready for global expansion? How did Danny find Index's expansion when opening up their first US office in 2011 in SF? What were some of the biggest challenges? How does Danny think about and assess generational transition within venture and Index more specifically today? 5.) Danny has spent over 3,000 hours on boards to date, how has Danny seen himself evolve as a board member over that time? What were some inflection moments in those hours that fundamentally changed the way Danny thinks? What advice would Danny give me, having just gained my first institutional board seat? Items Mentioned In Today’s Show: Danny’s Fave Book: Killing Commendatore by Haruki Murakami Danny’s Most Recent Investment: Goodeggs As always you can follow Harry, The Twenty Minute VC and Danny on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Tom Blomfield is the Founder & CEO @ Monzo, in it's simplest words, the bank of the future allowing you to open a full UK bank account in minutes, from your phone. To date, Tom has raised over $190m in funding for Monzo from the likes of Thrive, Accel, General Catalyst, Stripe, Mike Moritz and Goodwater just to name a few. As for Tom, prior to Monzo he was the Co-Founder of another of London's rocketship startups in the form of GoCardless and before that co-founded student marketplace Boso.com alongside Triplebyte Founder, Harj Taggar. In Today’s Episode You Will Learn: 1.) How Tom made his way into the world of startups from University and came to found the bank of the future in Monzo? 2.) Why does Tom believe that scaling a company today can really be broken up into 3 distinct phases? What are those phases? How does what one needs for each phase differ accordingly? What elements has Tom found most challenging to navigate in the scale-up phase? Are there challenges or elements that are the same across every company? 3.) Why does Tom believe that product decision-making is both an art and a science? How does Tom determine when is the right time to add ancillary products? How can one really stress-test true customer love for the first product? How does Tom balance between product expansion vs geographical expansion? How does Tom balance between being customer-driven vs customer informed? 4.) Tom has grown Monzo to 1.2m users with virtually no advertising, how does Tom respond to the statement that there is a lack of free and open distribution today? What does Tom mean when he says "when it comes to customer acquisition you have to play a different game"? In building community, what have Monzo done so right? Where have they made mistakes? What have been some big lessons on early community building? 5.) Having raised over $190m in VC funding, what have been some of Tom's biggest lessons when it comes to fundraising? Why does Tom believe that so few boards are managed and run well? Where do they go wrong? What do great board managers do to run an efficient process? What does Tom mean when he says "use board meetings as a tool to instil operational excellence?" Items Mentioned In Today’s Show: Tom’s Fave Book: The Hard Thing About Hard Things by Ben Horowitz As always you can follow Harry, The Twenty Minute VC and Tom on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Laura Deming is Founding Partner @ The Longevity Fund, the first VC firm dedicated to funding high-potential longevity companies. To date, Laura has raised $26m across 2 Longevity funds and has backed the likes of Unity Biotechnology, Precision Biosciences, Metacrine, Navitor, and Alexo Therapeutics. Prior to Longevity, Laura was accepted to MIT at the age of 14 to study physics and then dropped out to join the Thiel Fellowship and start The Longevity Fund. If that wasn't enough, Laura most recently founded Age1, a four-month startup accelerator program focused on founders creating longevity companies. In Today’s Episode You Will Learn: 1.) How Laura made her way from studying physics at MIT at just 14 to founding The Longevity Fund and dropping out to join The Thiel Fellowship? 2.) As a 16-year-old, looking to raise a fund to invest in longevity, how was the fundraise process for Laura? Why does Laura believe that raising your first fund is very much like raising a seed round for a company? What was the catalytic moment when the fundraise started to come together? What were the biggest challenges of the raise? 3.) Why does Laura believe that there is a shortage of young biotech founders today? What can be done to solve this and increase pipe? How does Laura find biotech founders compare to more traditional consumer and B2B founders she engages with? How does what they look for from their investor base differ? 4.) Laura has spoken before of "the importance of going against the herd"? How does Laura assess the current landscape for biotech investing? Is Laura concerned to see the entrance of much more traditional VCs into the space? How does Laura look to try and avoid groupthink? What is crucial to this? 5.) How does one need to think about portfolio construction when investing in an inherently riskier biotech space? Does Laura agree with the conventional wisdom around the lack of follow-on funding for biotech companies? How does Laura think about reserve allocation with Longevity today? Items Mentioned In Today’s Show: Laura’s Fave Book: The Mysterious Stranger by Mark Twain, Laura’s Most Recent Investment: System1 As always you can follow Harry, The Twenty Minute VC and Laura on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Jeff Morris Jr is the Founder of Chapter One, an early stage seed fund investing in blockchain assets, mobile and subscription businesses. Chapter One's Portfolio includes the likes of Lyft, Brandable, Crypto Kitties and many more incredible companies. However, Jeff is unique as Chapter One is only one of his hats, Jeff is also the Director of Product & Revenue @ Tinder and when asked to lead the revenue team they were ranked #17 in the app store. Within a year, under Jeff's leadership, Tinder became the #1 top grossing app in the world. In Today’s Episode You Will Learn: 1.) How Jeff made his way into the world of startups and angel investing, how that lead to his role as Director of Product and Revenue @ Tinder and a leading early-stage investor with Chapter One? 2.) Jeff has previously said, "apply an investor mindset to every product decision I make". What are the foundational questions involved? What are the inherent challenges of being so deep in product and investing simultaneously? What does Jeff think of VCs giving product advice to founders? What should the founders look for? What advice does Jeff give to the common question of "how do I get into investing and VC"? 3.) Why does Jeff disagree with the platform shift and the downturn in consumer mobile? What core innovations will drive the next wave of consumer mobile? Valuations in the space are often lofty, how does Jeff think about price and evaluate his own price sensitivity? How does Jeff think about scalable customer acquisition today in a world where incumbents dominate and price up the traditional channels? 4.) Jeff has said before that "investors treat crypto teams as if they are superhuman", what makes Jeff think this? How do their interactions differ than towards non-crypto teams? Why are lofty expectations dangerous for valuations? How does that put undue pressure on employees? Why are lofty expectations dangerous for product development? How do they affect the product roadmap negatively? 5.) How does Jeff approach the diligence aspect when it comes to investing? What have been some of his major lessons from making over 35 investments on the right diligence framework? How do shortened fundraising cycles negatively affect investor diligence processes? What can founders and investors do under these constrained time frames? 6.) Having worked with some of the greats from Doug Leone to Bill Gurley, what are some of the common traits in how the very best investors engage with founders? What were Jeff's personal learnings from seeing these greats in action? How did it change the way Jeff thinks about founder interaction and engagement? Items Mentioned In Today’s Show: Jeff’s Fave Book: The Catcher In The Rye, Googled Jeff’s Most Recent Investment: Radar Relay As always you can follow Harry, The Twenty Minute VC and Jeff on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Leo Polovets is a General Partner @ Susa Ventures, one of the valley's leading early-stage seed funds with a portfolio including the likes of Flexport, Robinhood, Lendup, Qadium, Rigetti, the list goes on. As for Leo, prior to joining the world of VC, he started his career as the second non-founding engineer at LinkedIn. After two years at LinkedIn, Leo spent 3 years at Google, largely working on real-time payment fraud detection. Finally, his last stop pre-Susa involved spending 4 years at Factual, a location data platform. In Today’s Episode You Will Learn: 1.) How Leo made his way into the world of VC from being the 2nd non-founding engineer at LinkedIn? 2.) Why does Leo believe that the hailed "warm intro" is actually dumb? What are the biggest drawbacks to this being commonplace in our ecosystem? What does Leo believe the mindset of investors should be instead? How does Leo filter through cold inbound? What are the 4 elements Leo looks for in all inbound? What can founders do to really make them stand out? 3.) Leo has previously heavily emphasised the importance of moats, how does Leo define moats and defensibility? When do founders have to think about moat building? Pre-product? Pre-launch? Pre-scaling? What questions suggest that a founders mindset is heavily oriented to moat building? With the majority of incumbents being usurped by platform shifts, does that not render moats significantly futile in the long term? 4.) What does Leo believe is the right way for investors to pass on an opportunity and communicate that to founders? What is wrong with the current way many do it? How does Leo present his opinion without getting into an argument with the founder on reasoning? What feedback has Leo been given from founders that has changed the way he thinks about being an investor? 5.) Controversial capitals Round: Ownerships is built on first check? Agree or disagree and why? Whether it is a $6m, $8m or $12m, if it is at seed, it is so early that price really does not matter so much? Agree or disagree and why? There is no point VCs spending their time with struggling companies in the portfolio. At best they return cents on the dollar. Only work with the outperformers to drive returns. Agree or disagree and why? Items Mentioned In Today’s Show: Leo’s Fave Book: Elad Gil's High Growth Handbook Leo’s Most Recent Investment: Interviewing.io As always you can follow Harry, The Twenty Minute VC and Leo on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Ooshma Garg is the Founder & CEO @ Gobble, the startup that allows you to cook a fresh homemade dinner in just 15 minutes. To date, Ooshma has raised over $30m in funding for Gobble from some of the best in the business including Initialized Capital, Keith Rabois, Reid Hoffman, Founder Collective, Felicis, Andreesen Horowitz and Thrive just to name a few. As for Ooshma, prior to founding Gobble she founded Anapata, an online site that matches students looking for jobs with potential employers. The company was ultimately acquired by LawWerx. In Today’s Episode You Will Learn: 1.) How Ooshma made her way from Wall St to changing the way America eats with Gobble today? 2.) Everyone has an opinion on the food delivery space with the public nature of Blue Apron, what does Ooshma mean when she says "small and mighty beats loud and weak"? Why did Ooshma not take the path of other competitors in the space of racing big and running fast? What is Ooshma's advice to founders on dilution and raise amounts? 3.) Would Ooshma agree with Alex @ LSVP that marketing portfolios are like venture portfolios, diversified and then double down? Would Ooshma agree with the concern around unfeasible CACs due to incumbents bidding them up on major platforms? Where does Ooshma see blue ocean when it comes to marketing channel success? 4.) What does Ooshma mean when she says "success is survival"? Why is capital efficiency even more important in online/offline businesses? What are some of Ooshma's examples of her "wartime approach" to capital efficiency? How does Ooshma explain this more sustainable growth to the growth-hungry VC community? Who is to blame for the insatiable desire for unreasonable growth; the founders or the VCs? 5.) Ooshma has raised over $30m with Gobble, analysing herself in fundraising, what does Ooshma believe she did particularly well during the raise and advise other founders to do? What elements would she like to improve upon for the next round? What is the story behind how Ooshma sprinted down the 101 to get Keith Rabois as an angel? Items Mentioned In Today’s Show: Ooshma’s Fave Book: The Wind-Up Bird Chronicle  As always you can follow Harry, The Twenty Minute VC and Ooshma on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Avidan Ross is the Founding Partner @ Root Ventures, one of Silicon Valley's most exciting newer generation of funds dedicated to backing bold engineers at seed. To date they have backed some incredible companies such as Nautilus Labs, Dusty Robotics, Tortuga AgTech and Instrumental.ai just to name a few. Prior to founding Root, Avidan was CTO at The CIM Group, with an aggregate of $15Bn AUM, Avidan was responsible for establishing the company’s technical vision and leading all aspects of the company's technology investment. Before that, he built algorithmic trading platforms as Director of Technology at WHW Capital.  In Today’s Episode You Will Learn: 1.) How Avidan went from building algorithmic trading platforms to back the next generation of revolutionary engineers with Root? 2.) What does Avidan mean when he says "the peace dividends of the autonomous car wars will generate more value outside of transportation?" How does the commoditisation of these core components affect subsequent industries? With their commoditisation, does it not become a raise to the bottom on price and margin? 3.) How does Avidan approach the layering on new software products to emerging hardware devices? What does this mean for the margin required both for the hardware and the software? How does Avidan's investor mentality alter when investing in hardware vs software? 4.) Why does Avidan believe "old and boring industries are the most exciting to build software in?" How does Avidan approach the common problem of customer education and selling to a customer base that does not want to talk to you and does not believe in your product? What do founders selling in these industries need to focus on to break through? 5.) How does Avidan assess the current landscape in terms of the quality and quantity of engineer CEOs? Why does Avidan believe the MBA CEO will be replaced by engineers? How has Avidan seen a variance in the background in the entrepreneurs innovating in "old and boring" industries? Items Mentioned In Today’s Show: Avidan’s Fave Book: Drive by Daniel Pink Avidan’s Most Recent Investment: Dusty Robotics As always you can follow Harry, The Twenty Minute VC and Avidan on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ryan Caldbeck is the Founder & CEO @ CircleUp, the startup creating a transparent and efficient market to drive innovation for consumer brands. To date, Ryan has raised over $50m with CircleUp from some friends and prior guests of the show including USV, Collaborative Fund and Canaan Partners just to name a few. Prior to CircleUp, Ryan spent nearly 7 years investing in consumer products with the likes of TSG Consumer Partners and Encore Consumer Capital. As a result of Ryan's success with CircleUp he has been recognised as a "Titan of Retail" by Bloomberg and "40 Under 40" by the San Francisco Business Times. In Today’s Episode You Will Learn: 1.) How Ryan made his way into the world of consumer investing and what the realisation moment was for him that the market needed a solution, CircleUp? 2.) Why does Ryan believe that venture capital has a fundamental problem? What is it about the economics of funds that Ryan has a problem with? Who is to blame for this situation; the LPs who fund it or the AUM hungry VCs? Why does Ryan believe the majority of micro VCs are micro as that is all they could raise? Is that really fair or true? 3.) Why does Ryan fundamentally believe the LP ecosystem and mechanism for backing funds is inherently broken? What is so wrong with current LP incentives? What does Ryan believe can be done to encourage more risk-taking and innovation from within the LP class? 4.) Recognising the antiquated nature of much of VC, what does Ryan believe the future of VC looks like? How will we see the use of data impact both sourcing and investment decision-making? Where does Ryan believe it has the most potential? Where is data so sparse that it will be challenging? How does Ryan believe the best managers of the future will use data? 5.) Consumer brands and DNVBs are riding high today, does Ryan believe we are in a consumer bubble? What does Ryan believe is so wrong about how the majority of the current crop of VCs analyse consumer businesses? How should they be analysed? Why does Ryan believe consumer exits will be smaller? Is it fair to say consumer is more capital intensive and largely sells for 1.6-1.8 EBITDA? Items Mentioned In Today’s Show: Ryan’s Fave Book: The Hard Thing About Hard Things As always you can follow Harry, The Twenty Minute VC and Ryan on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Ron Bouganim is the Founding Partner @ Govtech Fund, the first-ever venture capital fund dedicated to government technology startups. To date, he has backed some incredible category leaders including mark43, Neighbourly, MindMixer and SeamlessDocs just to name a few. Prior to GovTech, he was Accelerator Director @ Code for America and was an active angel investor and advisor working with more than twenty startups including ShareThrough, HelloSign, PagerDuty, and Close.io. In Today’s Episode You Will Learn: 1.) How Ron made his way into the world of technology and startups and became angel investing? How that led to the founding of Govtech and the belief in the space today? 2.) There is the notion that there many challenges to investing in Govtech and scaling companies in the space, how does Ron respond to the suggestion the sales cycles when selling to government are too long for startups to navigate successfully? How does Ron respond to the suggestion that the growth rates in the space are to low for venture returns? How does Ron respond to the suggestion that founders in the space are inherently older as only they have experienced the problems of government tech? 3.) Why does Ron believe that a vertically focused fund is the right strategy is creating a massively outperforming fund? How does Ron respond to the possibility of missing moonshots in alternate categories? What does Ron most look for in the co-investors that he invests with? What do they bring to the table? 4.) What does Ron believe are the 2 fundamental roles of a seed investor today? How does that differ from previous generations of seed funds? Why does Ron believe that fundraising and hiring help is now merely table stakes? What else can seed investors do to meaningfully move the needle for their portfolio? 5.) Why does Ron advocate for a highly concentrated portfolio? How does Ron respond to LP concerns around a lack of diversification? Does Ron believe that you can grow ownership of your best companies over subsequent rounds? What is the sign of success for Ron when the founder comes back for re-financing? Items Mentioned In Today’s Show: Ron’s Fave Book: Leonardo Da Vinci by Walter Isaacson Ron’s Most Recent Investment: Sema: Automated Code Maintenance As always you can follow Harry, The Twenty Minute VC and Ron on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Phil Libin is the Co-Founder & CEO @ All Turtles, the startup that believes they have a better way to make technology products, placing products first and companies later. Today they are building AI products in San Francisco, Paris and Tokyo. As for Phil, prior to All Turtles he was a Managing Director @ General Catalyst. Before that he spent 23 years founding different companies including founding Evernote, taking it from idea generation to productivity powerhouse raising over $160m in VC funding in the process, from some of the very best including Sequoia Capital. Phil is also an extremely successful angel with a portfolio including Gusto, TellApart and Binary Thumb just to name a few. In Today’s Episode You Will Learn: 1.) How Phil made his way into the world of tech startups many years ago, how that led to his entering VC with General Catalyst and to now, founding All Turtles? 2.) How does Phil assess the state of Silicon Valley today? Why does Phil believe that Silicon Valley has been becoming increasingly redundant over the last 20 years? Why does Phil argue that the VC Silicon Valley model has been primarily effective at serving it's own needs? What needs to occur for this to change? 3.) Why does Phil argue that the balance of power between startups and incumbents is shifting for 5 core reasons? Why does Phil believe that the data incumbency argument with AI startups is largely overstated and a fear tactic? How does Phil believe people's attitude toward working for incumbents has been shifting over the last few years? 4.) Why does Phil believe that the concept of a "company" is fundamentally outdated? What is so broken about this model? What does Phil believe will be the model of the future for the world's best product creators? Why does the idea of a generalist VC in this model largely not make logical sense to Phil? What does Phil believe the future of VC is? 5.) Why does Phil believe that his time in VC has made him a better CEO than even his time in operations? What have been his core learnings? How has his operating mindset fundamentally shifted? Why does Phil argue the core role of the CEO is not management upscaling? Why does Phil argue it is wrong to assume the only mindset is growth? Items Mentioned In Today’s Show: Phil’s Fave Book: Clock of The Long Now As always you can follow Harry, The Twenty Minute VC and Phil on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Linda Xie is a Co-Founder & Managing Director @ Scalar Capital, one of the leading crypto asset funds to have been born over the last few years with Linda becoming one of the most prominent figures in the space. Prior to co-founding Scalar, Linda was a product manager at Coinbase where she worked with regulators and law enforcement. Before Coinbase, she was a portfolio risk analyst at AIG. If that was not enough, Linda is also an advisor to 0x, the critical infrastructure layer in the emerging financial stack built on a foundation of Ethereum token standards. In Today’s Episode You Will Learn: 1.) How Linda made her move into the world of crypto joining Coinbase back in 2014 and how that led to her founding of Scalar? What were her biggest takeaways from seeing the first-hand scaling of Coinbase? 2.) What is a privacy coin and why does it matter? What are some of the dominant legitimate uses for privacy coins? From ZCash to Monero to Dash, there are many players in the space, what are some of the core benefits and tradeoffs of each platform? What is the fundamental problem with privacy coins today? 3.) What is a decentralised exchange, why does Linda believe it is inherently important? How does Linda assess the current exchange environment today? Where does she see it moving over the coming years? What have been some of Linda's biggest learnings advising 0x?  Given the mission and ethos of crypto, does Linda believe that centralised exchanges fundamentally go against the core ethos of the space? 4.) How does Linda perceive the state of ethereum today? What are some of the core challenges facing ethereum today? How does ethereum compare to alternative smart contract platforms? What is their differentiation? Will we see a winner take all/most market within smart contract platforms? Will we see smart contract platforms be regionally fragmented? 5.) How does Linda address the fundamental challenge of valuing tokens today? What has been her preferred model in doing this to date? How does Linda assess the mega raises we have seen over the last year? How does Linda think about preventing projects from raising huge rounds just to stay in step with the mega raises of their competitors? Items Mentioned In Today’s Show: Linda’s Fave Book: Sapiens: A Brief History of Humankind Linda’s Most Recent Investment: Kadena As always you can follow Harry, The Twenty Minute VC and Linda on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Dennis Mortensen is the Founder & CEO @ X.ai, the startup that realises scheduling sucks and provides ridiculously efficient AI software that solves the hassle of meeting scheduling. To date, Dennis has raised over $44m in VC funding from the likes of Firstmark, IA Ventures, Lerer Hippeau, DCM and more fantastic names. As for Dennis, he is an expert in leveraging data to solve enterprise use cases and prior to X.ai he was the Founder & CEO of 3 companies, 2 of which were acquired and one which went bust or as he describes a rather expensive MBA. Dennis is also the author of Data Driven Insights, on collecting and analyzing digital data. In Today’s Episode You Will Learn: 1.) How Dennis made his way from Copenhagen to New York, the world of startups and came to found one of the hottest AI companies of our day in X.ai? 2.) What were Dennis' biggest lessons from enjoying 3 successful exits prior to X.ai? What were Dennis' learnings from his one failed startup? What would he do differently if he were to start another company? How does Dennis navigate the balance of between pursuing a vision and miss vs when something is just not working? 3.) Does Dennis believe that there really is such a thing as an AI first company? What is the right mentality to approach a company solving a problem through AI with? How does Dennis view the standardisation of AI tools today (Tensor Flow, libraries etc etc)? Does this remove barriers and defensibility for AI companies? What is the key to success for all AI companies? 4.) What does a truly differentiated data acquisition strategy look like? How can one determine the different utility value between different sizes of data? At what point does Dennis believe utility value of data diminishes due to the sheer size of existing data? 5.) Does Dennis believe that conversational UI is truly a paradigm shift in the way we interact with our devices or an iterative improvement? What have been some of the biggest lessons for Dennis in designing conversational UI products? What have been some of the fundamental challenges? Items Mentioned In Today’s Show: Dennis’ Fave Book: The Narrow Road: A Brief Guide to the Getting of Money, Shoe Dog: A Memoir by the Creator of NIKE, Mike Tyson: Undisputed Truth As always you can follow Harry, The Twenty Minute VC and Dennis on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.  

Phin Barnes is a Partner @ First Round Capital, one of the most prestigious and successful early-stage funds of the last decade with a portfolio including the likes of Uber, Square, Warby Parker, HotelTonight, GOAT, PatientPing, Atrium and more incredible companies. As for Phin, in his own words, he learned the business of startups helping grow AND1 from $15M to $225M in revenue as Creative Director for Footwear, and started his own fitness video-game company, producing Yourself!Fitness, the first game of its kind for Xbox and PlayStation 2 where he built partnerships with the likes of Procter & Gamble and McDonald’s. Phin also writes the most fantastic blog, sneakerheadVC, that really is a must read. In Today’s Episode You Will Learn: 1.) How Phin came to be a Partner @ First Round by working for free, with no plans to be a Partner? 2.) What were Phin's biggest lessons from learning from and observing Josh Kopelman? How does Phin define true success as a VC today? Why is the model of determining success according to returns fundamentally flawed? How does Phin approach the need for VCs to be both curious and competitive? What is the nuance there? 3.) Why does Phin believe that the commonly discussed "pattern recognition" is another term for intellectual laziness? What does Phin do to prevent his forming assumptions on the founders he meets? Why does Phin fundamentally disagree with the common VC habit of looking for weaknesses in founders? 4.) Does Phin agree that we have an oversupply of capital in market today? How does Phin determine when a stretch on price is a stretch too far? Why does Phin think that more emphasis should be placed on the business model that VCs have? What does Phin mean when he says that he is on the "sell side"? 5.) What does Phin mean when he says that "VCs should focus on a founders ability to optimise for learning per dollar spent"? Is cash ever a defensible moat in it's own right? What does Phin believe is the right way for founders to use capital as a weapon? 6.) How does Phin and First Round think about the right way to allocate reserves effectively? What does that look like in reality? What does the decision-making process look like on re-investments? Why does Phin believe that the framework of "pro-rata is largely lazy? Items Mentioned In Today’s Show: Phin’s Fave Book: Writing Down the Bones: Freeing the Writer Within, Boyd: The Fighter Pilot Who Changed the Art of War Phin’s Most Recent Investment: Ubiquity6 As always you can follow Harry, The Twenty Minute VC and Phin on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Patrick Morley is the President and CEO @ Carbon Black, the company that combines unfiltered data collection, predictive analytics, and cloud-based delivery to provide superior endpoint protection. Prior to their IPO in April 2018, Carbon Black had raised over $150m in VC funding from the likes of Sequoia Capital, Accomplice, Kleiner Perkins and Highland Venture Partners just to name a few. As for Patrick, under his leadership, he has taken Carbon Black from startup to market leader with over 800 employees. Before Carbon Black, he was CEO of Imprivata Corporation and held senior leadership positions with six venture-backed software companies, including three that had successful IPOs. In Today’s Episode You Will Learn: 1.) How Patrick made his way into the world of startups and came to be CEO @ Carbon Black where he turned a startup into a public company and market leader with 800 employees? 2.) Patrick has previously said "there are 7 key themes to building a great company", what are those themes? From taking 4 companies public what are the patterns in building a business the right way? How does Patrick look to create a culture of accountability but also with a risk-taking mentality? How does one retain startup culture with scale? 3.) How does Patrick view his role as CEO today? What 3 characteristics do all great CEOs need to embody and then act on? Would Patrick agree that some people are destined for certain stages of a company's life? How does Patrick determine between a stretch and a stretch too far in a VP? What does that subsequent communication look like? 4.) Mike Dauber @ Amplify previously said on the show "timing kills more startups than dollars", would Patrick agree with this? How does he view market timing? What advice would Patrick give to founders who are 3-4 years ahead in market? What are the challenges? What are the right ways to communicate the path to timing it right? 5.) Why did Patrick choose this year to take Carbon Black public? What are the fundamental pros and cons of being a public company today? How does Patrick assess the role that VCs played in the building of Carbon Black to IPO? What must investors always remember in their interactions with founders? What must founders be cognizant of when selecting their investors and board members? Items Mentioned In Today’s Show: Patrick’s Fave Book: Built To Last: Successful Habits of Visionary Companies As always you can follow Harry and The Twenty Minute VC on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Woody Marshall is a General Partner @ TCV, one of the most successful growth funds of the last decade with a portfolio including the likes of Facebook, AirBnB, Spotify, LinkedIn and many more incredible companies. Woody joined TCV in 1995 and has since led investments in Spotify, Netflix, AirBnB, Peloton, Groupon and the list goes on. Due to this phenomenal success, Woody has been named numerous times to the Midas List by Forbes as one of the industry’s top technology investors. Prior to joining TCV, Woody spent 12 years at Trident Capital, where he focused on the payments, internet, and mobile markets. In Today’s Episode You Will Learn: 1.) How Woody made his way into the world of VC over 23 years ago and came to invest in products of a generation such as AirBnb, Spotify and Netflix? 2.) What have been the foundational changes Woody has seen over his last 23 years in venture? How did witnessing the boom and bust affect his operating and investing mentality? How does Woody approach price sensitivity? When is stretching on price a stretch too far? 3.) How does Woody analyse and assess the extended period of privatisation for companies today? How does the mega raises of funds from Softbank, Sequoia, GC, Lightspeed etc change the competitive landscape for Woody? Is there a surplus of capital in market today? Why does Woody believe the pie is larger than it has ever been? 4.) Does Woody agree that the dominant role of CEO is management upscaling? From Woody's portfolio, on hearing this, who is the first CEO that comes to mind and what is the story behind it? What are the mistakes that CEOs tend to make most often when scaling into hypergrowth? What are the 2-3 things that all companies need to focus on when product market fit is apparent and they need to scale? 5.) Woody has spent over 3,500 hours in the board seat, how has he seen himself evolve and develop over time as a board member? What were the biggest learning curves and points of development for Woody? How do the best founders manage and operate their board? Who exemplifies this best from recent memory? What do they do? Items Mentioned In Today’s Show: Woody’s Fave Book: The Boys in the Boat Woody’s Most Recent Investment: Peloton As always you can follow Harry, The Twenty Minute VC and Woody on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Afton Vechery is the Co-Founder & CEO @ Modern Fertility, the startup that guides you through your fertility hormones now so you have options later. To date they have raised over 7m in funding from some of the leading players in venture including USV, First Round Capital, Maveron, SV Angel and Y Combinator. As for Afton, prior to Modern Fertility, Afton was a Product Manager @ 23andMe where she was the sole product manager responsible for all consumer-facing genetic tools. Before 23andMe, Afton was a Strategy and Finance Consultant @ Willow Pump where she participated in fundraising that led to successful $15M fundraise. In Today’s Episode You Will Learn: 1.) How Afton made her way into the world of startups with 23andMe and then came to change the way we think about fertility with Modern Fertility? 2.) Afton has previously emphasised the importance of having "frameworks for success". What does that mean? How do those frameworks break down? How does Afton think about the decision-making process around prioritisation? How does Afton think about the difference between being customer informed and customer driven? 3.) Why does Afton believe that there are times when you should not test the MVP? Why is this? What would Afton do differently in the MVP process if she had her time again? How does Afton think about and respond to the statement "move fast and break things"? 4.) Why does Afton believe it is important to let everyone "rip apart your business"? What are the fundamental benefits of this? From the ripping aparts, Afton has experienced, what have been the biggest takeaways? What was their argument? How did Afton respond? How did her thinking and mentality change as a result? 5.) Why does Phin Barnes @ First Round say Afton is "hard as nails"?  What were some of Afton's biggest learnings from her early engineering role? How does Afton think about entrepreneurial resilience today? What advice does Afton give to emerging entrepreneurs and first-time founders? Items Mentioned In Today’s Show: Afton’s Fave Book: Motherhood Rescheduled As always you can follow Harry, The Twenty Minute VC and Afton on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Rebecca Kaden is a General Partner @ Union Square Ventures, one of the most successful funds of the last decade with a portfolio including the likes of Twitter, Twilio, Zynga, Soundcloud, Tumblr, Lending Club and many more. As for Rebecca, prior to USV, Sarah was a General Partner @ Maveron, a consumer-only seed and series A fund where she invested in the likes of Allbirds, Dia & Co, Periscope, Earnest and Eargo just to name a few. Before Maveron, Rebecca took the route of many great VCs and was a journalist, working as Special Projects Editor @ Narrative Magazine. In Today’s Episode You Will Learn: 1.) How Rebecca made her way into the world of VC from journalism? How her journey with Maveron led to her becoming a General Partner with the prestigious USV? 2.) Having mastered the craft of VC in the world of consumer, how does Rebecca respond to Peter Fenton and Jeremy Levine's statement, "we are in a consumer downturn"? How does Rebecca think about the lack of free and open distribution today? How can startups compete with incumbents for cost-efficient customer acquisition? 3.) How does Rebecca evaluate the role of Amazon today? How does Rebecca look to get comfortable that Amazon is not moving into the space of a portfolio company? Does Rebecca agree, "if you are not a top 3 priority", you have a couple of years on them? How can startups learn from the execution advantage shown by Amazon over the last decade? 4.) With several recent consumer acquisitions under $200m, does Rebecca still believe that venture returns can be made at scale in consumer? How does Rebecca analyse how to think about multiple on revenue when evaluating consumer companies? Why Does Rebecca believe we are in a moment of fragmentation, not consolidation? 5.) How does Rebecca compare the partnerships of US and Maveron having been a GP now at both firms? What are the similarities? What are the differences? What does Rebecca believe are the core advantages of small partnerships and controlled fund sizes? How does the addition of the thesis-driven investing style effect Rebecca's thinking? Items Mentioned In Today’s Show: Rebecca’s Fave Book: Pale Fire  Rebecca’s Most Recent Investment: Modern Fertility As always you can follow Harry, The Twenty Minute VC and Rebecca on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Maynard Webb is truly unique, he has worn 3 different hats and excelled in all of them. First, he is the Founder of The Webb Investment Network, the institutionalisation of his personal investing where he has invested in the likes of Zuora, GOAT, WePay, Okta, PagerDuty and many more incredible companies. He is also a Co-Founder and Board Member at Everwise, the startup that helps companies tailor, scale and run training at enterprise scale. Everwise has raised over $26m in funding from the likes of Sequoia Capital and Canvas Ventures. Finally, Maynard sits on the board of some of the biggest companies of our time including Salesforce and Visa. Previously Maynard was Chairman of the Board of Yahoo!, CEO of LiveOps, and COO of eBay. In Today’s Episode You Will Learn: 1.) How Maynard made his way into the world of startups and came to invest in his first company, founded by Sequoia's Jim Goetz and how that led to eBay, LiveOps and more? 2.) Does Maynard believe we have an excess supply of capital in the market today? What does Maynard think of the mega $Bn+ funds being raised on a frequent basis? How does this distort pricing in the market? How does Maynard think about his own price sensitivity? What does this mean for his available reserve allocation? 3.) Does Maynard believe that the dominant role of CEO is management upscaling? How does Maynard advise on the transition from manager to inspirational leader? How do the vest best CEOs hire the very best execs? How does Maynard know when a stretch VP is a stretch too far? How should founders determine and approach "bet the company" decisions? 4.) When should a founder start installing their board? What does Maynard believe is the optimal board construction, both in characters and profiles? How has Maynard seen his own style of board membership changed over the years? What are the best board members talk to listen ratios? How can founders create alignment among their board? 5.) What is the right way for founders to deal with "s*** hit the fan moments"? What is the framework to approach this with? Where do many go wrong in their approach? How does one communicate this to the wider team, investors and board? What have been Maynard's biggest personal learnings here from eBay? Items Mentioned In Today’s Show: Maynard’s Fave Book: The Better Angels of Our Nature As always you can follow Harry, The Twenty Minute VC and Maynard on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Sarah Tavel is a General Partner at Benchmark, one of the world’s leading VC funds with a portfolio including the likes of Twitter, Uber, Snapchat, eBay, WeWork, Yelp and many more revolutionary companies of the last decade. As for Sarah, Sarah has led Benchmark's investments in and currently sits on the boards of Chainalysis and Hipcamp. Prior to Benchmark, Sarah was a Partner at Greylock Partners, where she led Greylock's investment in Sonder and another (unannounced) company. Before Greylock, Sarah was one of the first 35 employees at Pinterest where she led the company's international expansion and aided in the closing of the Series C financing. Sarah was also the product lead for search, recommendations, machine vision, and pin quality and led three acquisitions as she helped the company scale through a period of hyper-growth. In Today’s Episode You Will Learn: 1.) How Sarah made her first foray into the world of venture with Bessemer over 10 years ago? How that led to Pinterest and how she came to be a GP at Benchmark today? 2.) Speaking of Sarah's operating career with Pinterest, Pat Grady said on the show "never has the rate of decay on operating experience been greater". How does Sarah think about and respond to this? How has operating made Sarah a strong investor? What are the drawbacks that this operating experience can present for investors? 3.) Moving to evaluation, Andy Rachleff, Founder @ Benchmark said on the show, "good team poor market, market wins; good market, poor team, market wins. How does Sarah think about the balance between founder vs market? Why is going after big markets so hard? What should investors look for in a market with that in mind? How does Sarah determine the right time to open up adjacent markets? 4.) There has never been a greater supply of capital in the market than today, does Sarah believe we have an excess supply today? Does Sarah agree with her Partner, Peter Fenton, "no good deal is too expensive in hindsight"? How does Sarah assess her own price sensitivity? How does it depend on the opportunity? How has it changed over time? 5.) Having 2,5000 hours on boards, how has Sarah seen herself develop and change as a board member? What have been some of the biggest learning curves? What are the commonalities in the very best board members Sarah works with? how doe the best entrepreneurs manage and use their boards effectively? 6.) Why does Sarah think that crypto today is very much like the world of adtech in the early days? How does Sarah think about the requirement for specialisation in the space? WIll this be a game for the specialised crypto funds or can generalist VC funds compete? Items Mentioned In Today’s Show: Sarah’s Fave Book: Creating the Kingdom of Ends Sarah’s Most Recent Investment: Hipcamp As always you can follow Harry, The Twenty Minute VC and Sarah on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.