Matt Mullengweg was a high school student looking for a better way to customize his blog when he discovered the open source software community and created the WordPress platform. A few years later, after dropping out of the University of Houston for a brief stint at CNET Networks, he founded Automattic, which he describes as a holding company for products such as WordPress.com, Jetpack, WooCommerce, Simplenote, Longreads and The Atavist. And just like over 40% of the web today, they all run on WordPress. Unlike many of its contemporaries, Automattic, which became a unicorn in 2014, hasn’t gone the IPO route or been acquired. In February of 2021, the company closed a new primary funding round of $288M, and it continues to grow at a rapid pace. The company recently did a $250M share buyback, primarily targeted at current and former employees, at a $7.5B valuation. Matt continues to be energized by the open source community, which keeps him connected to users all over the globe. In fact, even before the pandemic made remote work the norm, Automattic was at the forefront of changing the way we work. A distributed company since day one, Automattic now employs 2000 people across 90 countries. Matt has influenced many leaders with his experiences of running an entirely remote business and keeping people connected, both technically and culturally. He shares more in this episode about what they’ve learned about remote work, and what they’re still figuring out. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com

As Co-Founder and Chairman of Techstars, David Cohen has spent nearly his entire career focused on helping entrepreneurs succeed. Aspiring founders and early-stage entrepreneurs from around the world apply to Techstars’ startup accelerators to get three months of hands-on mentorship, access to a worldwide network and a check for $20,000 in exchange for 6% of the startup. When I spoke with David for this episode back in 2008, the program was just two years old, part of a trend of structured angel investing and mentoring that was started by Paul Graham’s Y Combinator. At that time, two companies founded at Techstars had been acquired: socialthing!, which was sold to AOL, and Intense Debate, which was sold to Automattic (the makers of WordPress). Fast forward more than a decade later, and David is a first-round investor in approximately 2,100 internet startups, including Uber, Twilio, SendGrid and Pillpack. Now running 40-55 accelerators during any given year, Techstars has funded over 2,600 companies that have gone on to raise more than $14.5B and create a market cap of more than $44B. In this episode, David shares his own stories of success and failure as an entrepreneur, how he decided to start Techstars and his advice for anyone thinking about starting up — or investing in — a new venture. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com

Originally from Denmark and now living in the US, Henrik Werdelin has been recognized as one of the “Top 100 Most Creative People In Business” by Fast Company and named to the “Silicon Alley 100” by Business Insider. His path to entrepreneurship took him through the BBC, MTV and Joost before he ended up creating Prehype, a “halfway house” for entrepreneurs like him, who didn’t know what to do next. Not only has Prehype incubated new ventures from scratch and in collaboration with Fortune 500 companies, it’s also where he hatched his own startup, Bark. With a mission to make dogs as happy as they make us, Bark quickly took off, expanding its BarkBox subscription service over the years to include toys, pet food, home and health product lines. In June of 2021, Bark went public via SPAC by merging with Northern Star Acquisition. The newly combined company is valued at approximately $1.6 billion, and Bark is expected to generate around $365 million in revenues and reach a gross profit of $221 million this year. But the coolest part of the job, Henrik says, is getting to make dogs happy. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com Produced by Podcasttech.com

Fabrice Grinda is one of the world’s leading Internet entrepreneurs and investors, with over 150 exits on 500 angel investments. When I first interviewed him for this podcast, way back in 2005, the then-31-year-old French native was in the process of packing up his office at Zingy, the mobile media start-up he’d founded in 2000. After growing Zingy to $200 million in revenue, Fabrice had sold the company for $80 million in 2004. Eighteen months later, he was stepping down as CEO and looking ahead to his next adventure. At the time we spoke, Broadband, iTunes and podcasting were all new, and Fabrice saw it as “the beginning of a hundred year revolution.” He recognized that there were going to be huge opportunities ahead for the entrepreneurs who were willing to take the risks and go all in on a big idea. And as Fabrice’s story shows, you don’t have to be the one who comes up with the groundbreaking product to become a wildly successful entrepreneur. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com

Guy Kawasaki’s name has become almost synonymous with tech entrepreneurship and evangelism. Over the past 25 years, he’s had a hand in advising a generation of tech start-ups and innovators, either directly, through stints at Apple and Google, or through his writings, speaking engagements, podcast and numerous books. Guy has started up a few of his own companies as well, and the venture capital fund he launched, Garage Technology Ventures, has invested in a variety of early-stage technology companies. I first interviewed Guy for this podcast in 2006. Catching up with him nearly 15 years later was a real treat — although we were a little delayed getting started. As Guy explained, the waves were pretty good that day, so he had to get a little extra surfing in. When he’s not riding the waves, Guy is the Chief Evangelist for Canva, bringing the good news of the democratization of design to the world for this Australian startup, which is now valued at A$6 billion. In this episode, he shares what it means to be an evangelist, the role of luck in entrepreneurship, how his work life has evolved and the career achievement he’s most proud of — which also happens to be the one he feels is most underappreciated. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com

CD Baby founder Derek Sivers made two appearances on Venture Voice in the early days of this podcast. In our first conversation, he described the process of growing the company into one of the largest sellers and distributors of independent music online, with $25 million in revenue and 50 employees at the time. This week we’re revisiting our second conversation, which happened three years later. What a difference three years makes. In August 2008, Derek, who owned 100% of the equity, sold the company for $22 million. When we spoke in October of that year, Derek described what drove his decision to sell the company, how he sold it (including a Willy Wonka style plan that never came to fruition) and what he learned along the way. As you’ll hear, Derek wasn’t driven by the money. If anything, it was a deterrent to selling. So his lifestyle didn’t change when he sold CD Baby — and he made sure of that by putting all of the money into a charitable trust that will go toward music education when he dies. If you’ve ever felt disconnected from your own venture or wrestled with the idea of whether you should sell your “baby,” this episode offers some good insight and excellent advice. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com

Born into a family of entrepreneurs, LivePerson founder and CEO Robert LoCascio always had the entrepreneurial spirit, going back to his teens when he and a friend started an auto detailing business. After graduating college, he had a brief stint in a “real” job, but that experience — he ended up getting fired via fax — convinced him that he never wanted to work for someone else again. Determined to control his own destiny, he took out $50,000 on credit cards to fund his first business, IKON. When a customer asked them to build a website, he made a bold decision to shift the business and, in the process, get himself in the mental shape necessary to be the entrepreneur he wanted to be. In this candid conversation, Robert reveals not just the business side but also the psychological and emotional journey involved with being an entrepreneur. His story is one of many ups and downs — from being hounded by credit card companies to taking his company public just before the dot com bubble burst to narrowly avoiding stock delisting and then ultimately steering his company to its current $3.5 billion value. In some uniquely disruptive times, Robert also hasn’t been afraid to disrupt his own businesses. He believes the doubts and the dark days have something important to teach us, and that’s why he says the biggest lesson all entrepreneurs should take away from his story is this: Never quit when you’re down. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com Produced by PodcastTech.com

This week we’re revisiting my 2007 interview with Tom Perkins, who was one of Silicon Valley’s most successful venture capitalists. The firm Tom co-founded, Kleiner Perkins, is responsible for funding some of the most well-known companies of the past four decades, including Google, AOL, Genentech, Sun Microsystems, Compaq and Tandem Computers. With that track record, Tom’s name is now almost synonymous with venture capital. But he actually cut his teeth as an entrepreneur. Educated at MIT and Harvard, Perkins first made his mark by managing the initial growth of Hewlett-Packard’s computer business while simultaneously inventing the first cheap and reliable laser. The company he built around the laser, University Laboratories, made him independently wealthy and allowed for the creation of Kleiner Perkins. But more than just the money, his time at HP gave him the opportunity to learn from a “giant” of business, Dave Packard. Packard, Tom told me, operated like a venture capitalist within HP and gave him a model to emulate when he started his firm. Though Tom wowed the business press for much of his career, later in life he gained national attention for having a key role in a 2006 Hewlett-Packard board scandal, briefly marrying Danielle Steel and building the world’s largest privately owned sailing yacht. When I spoke with Tom, he was busy in “retirement,” serving on a number of corporate boards of directors, including News Corp’s and HP’s. He’d also stepped back into the media spotlight with the publication of his memoir, Valley Boy: The Education of Tom Perkins. This episode offers a fascinating glimpse into the mind of the outspoken and pioneering venture capitalist. Tom died in 2016, but his advice for entrepreneurs remains as relevant as ever. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com

Jon Oringer is not a professional photographer. But when he needed images to market his growing internet business, the traditional stock agencies were still stuck in the world of print, so he took the DIY approach. What started as a way to fill a need for his own company turned into a side business that quickly gained traction. So quickly, in fact, that he turned his attention to it full time. Jon built Shutterstock on a “two-sided marketplace” subscription model that has its roots in Pop-Up Eliminator, a tool he built while he was still in college. While that app was disrupted out of existence when Microsoft built pop-up blocking into Internet Explorer, he’d grown it to a million dollars in revenue by that time. In this episode, Jon shares how he started with a portfolio of app ideas that was eventually whittled down to Shutterstock. You’ll hear about the company’s rapid growth trajectory, Jon’s decision to take secondary funding in 2007 to accelerate the pace even more and what it was like to take the company public in 2012. Although he stepped down as CEO in February 2020, he still owns 37% of the company today and spends half his time working on Shutterstock in his role as Chairman. The other half is spent with his business incubator, Pareto, where he’s looking for the next entrepreneurs and business ideas to invest in. Listen now on Apple Podcasts, Overcast and Spotify. If you love it, please help more people find it by leaving a review! *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com

Fred Turner was only 16 when he built his first PCR machine, a tool used to amplify small segments of DNA or RNA. He was interested in sequencing his own genome, but he soon discovered there were others who had a need for these kinds of cheaper, faster testing capabilities. When English pedigree farmers came calling, he pivoted his attention to agriculture, but soon found himself in need of funding to be able to scale to meet demand. That led him to the US, where he went through Y Combinator, which ultimately funded his first startup, Shield Diagnostics. Fred’s focus would return to human diagnostics, first with an STD testing business, where he learned, among other things, “The US healthcare system is just a bit of a mess.” What he couldn’t have predicted at age 16 when he first built that PCR machine is that less than a decade later, a global pandemic would bring the world to a halt, and PCR-based testing would play a critical role in getting people tested quickly and helping prevent the spread of COVID-19. Fred had been working on a sepsis testing business when COVID-19 hit. Once again, he pivoted. His company Curative, which now employs 5,000 people across the country, has administered 18 million tests (including one to me) in the past year, which at $100 per test implies $1.8 billion in revenue! In addition, they’re providing vaccinations and other essential health services. It sounds like an overnight success story, but as you’ll hear, there have been plenty of ups and downs, including one seriously low point following an unsuccessful Series B round that effectively shut down the STD testing business. Now that he’s running a business whose mission, he says, is “to put ourselves out of business,” Fred will be looking at the next pivot he can take in healthcare, drawing on the infrastructure and institutional knowledge he’s put in place to provide a better, more integrated patient experience at every touchpoint. It’s going to be fascinating to see where he goes next. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com

How do you start a whole new category of beverage — without any experience in the beverage industry? This week, we dip back into the archives for my 2005 interview with Sharelle Klaus, founder and CEO of DRY Soda. A former dot-com entrepreneur with a passion for food and wine, Sharelle was fed up with the lack of sophisticated beverage options available to her when she went out to eat while pregnant with each of her four children. She channeled that frustration into the launch of a startup focused on crafting culinary sodas, an entirely new category that would fill the gap for a huge untapped market. When we spoke in 2005, DRY Soda had only been in business about a year, but it had already taken the West Coast by storm and was in the process of expanding nationwide. Today, DRY Soda can be found in restaurants and stores across the U.S. as well as internationally and online. Building on the success of their “botanical bubbly” line of eight culinary sodas, Sharelle also recently released her mixology manual, “The Guide to Zero-Proof Cocktails.” This episode takes you back to those heady early days, as Sharelle describes coming up with the recipes for the first four flavors, making her first sales, raising funding and building her team. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com

It was a real treat to interview Food52 CEO and co-founder Amanda Hesser, who’s an old friend going back to my early days in the New York startup community. Listening to her tell the story of her entrepreneurial journey, you get the sense that she’s lived many lives — from studying food history alongside classmates like Corby Kummer and Sheryl Julian to apprenticing in a bakery in Germany (where she was the only woman in the kitchen) to sharpening her cooking and writing skills at a Chateau in Burgundy and ultimately landing at The New York Times, where she served as food editor of The New York Times Magazine. One common theme that emerges from all of these experiences is Amanda’s all-in approach. She follows her gut, immerses herself in the adventure and soaks up everything she can from it. You can also see how all of those lives became part of the DNA of Food52. Although Amanda told me they’ve often felt out of sync with what’s popular or cool at the moment, the truth is, they’ve always been ahead of the trends. Since its launch in 2010 as a place for people to talk about food and share recipes, Food52 has grown to 100 employees, won a prestigious James Beard Award for Publication of the Year and launched a thriving online shop, including its own line of products. In 2019 The Chernin Group acquired a majority stake in the company for $83 million. As one of the few women in the New York startup scene back when I first met her, today Amanda is a role model for a new generation of entrepreneurs. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com

Sometimes, a big mistake can trigger a big idea. In 2003, Mike McDerment was running a small web design agency when he accidentally saved over an old invoice. Frustrated and looking for a better way to bill clients, he decided to build the better way himself. The solution he came up with would become the foundation for FreshBooks, a cloud-based accounting software for freelancers and service-business owners, which is now the #2 small business accounting software in America, with around 500 employees and customers in more than 100 countries. In true startup fashion, Mike ran FreshBooks out of his parents’ basement for the first 3 ½ years. His mother was even an early investor, securing a line of credit for the co-founders since they couldn’t get a loan themselves. In 2014, after a decade of incremental growth, FreshBooks raised $30 million in venture capital funding. A second round in 2017 raised another $43 million, fueling the company’s growth and dominance in the booming self-employed and small business market. Mike shares how he made the tough decision to pursue VC funding, the innovative approach they took to replatforming, how his role has evolved over time and what he’s doing to keep his entrepreneurial chops fresh. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com

We’re heading back to the archives, this time revisiting my 2006 interview with Steve Hindy, co-founder of Brooklyn Brewery. Steve’s career journey, both as a foreign correspondent before he took the entrepreneurial leap, and as a brewery owner, is the stuff of blockbuster movie fare. After all, being robbed at gunpoint and being threatened by the mob are not problems the average entrepreneur encounters (thankfully!). Steve and his co-founder Tom Potter forged ahead through the ups and downs of the early years, even staring down bankruptcy at one point. But as Steve told me, building a business is like climbing a mountain. You put one foot in front of the other, you do the work everyday, and eventually you get there. In 2003, Steve and Tom sold their beer distributorship for $10 million to focus on the brewery. Since we spoke, Brooklyn Brewery has grown from $12 million to over $50 million in revenue, and it’s become a local institution, committed to investing in and giving back to the community. At the end of 2020, 36 years after convincing his neighbor and homebrew partner to quit his steady job at a bank and join him in starting a brewery, Steve announced his retirement. His story is proof that with grit, determination and a bit of fearlessness, you can turn your passion into a thriving — and thrilling — venture. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com

Like most successful entrepreneurs, Mark Wilson, CEO of Chime Solutions, is an ambitious and savvy business person who’s driven by a strong work ethic and desire to make an impact. But when Mark founded his first company, Ryla, he was inspired by more than just the opportunity to build a business. Throughout his life, he had seen how talented people from minority communities often didn’t get the same chances as others who had more advantages. First with Ryla, which he ultimately sold for $80 million, and now with Chime Solutions, where he has a goal of creating 10,000 jobs around the U.S., Mark is aiming to level the playing field. In the process, he’s showing other CEOs that there’s a wealth of untapped talent out there, and that investing in people is good for business. Mark’s story is an inspiring reminder of what it means to be mission-driven and how much more powerful and fulfilling work is when you’re guided by meaning and purpose. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com

Today, Evan Williams is most well-known for being the billionaire co-founder of Twitter, as well as Blogger and Medium. But back in 2005 when this episode was recorded, Twitter hadn’t even been conceived of yet. When we spoke, Ev had just raised about $2 million in venture capital money for a hot new podcasting company he was about to launch called Odeo. Spoiler alert: Odeo didn’t make it. But a little side project had promise, and about a year after this interview was conducted, he and his partners decided to shift their focus to it. That side project was Twitter. This episode takes us back to Ev’s mindset as he was gearing up for the launch of Odeo. It’s also a good reminder that failure is part of the entrepreneurial path. On a personal note, I have to say, this interview changed my life. Getting to know Ev and becoming one of the first users of Twitter ultimately gave me the idea for my first big success as an entrepreneur, The Shorty Awards. And that led me to start up my software company, Muck Rack. You never know where your journey is going to take you. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com

It’s a special holiday edition of Venture Voice, and the holiday we’re celebrating is Festivus. You may know it from the hit TV series Seinfeld, where the holiday “for the rest of us” is featured in the episode “The Strike” as an invention of George’s dad, Frank. Festivus was, in fact, invented by someone’s dad, but as you’ll hear in this episode, it wasn’t George Costanza’s; it was Seinfeld writer Dan O’Keefe’s. Dan shares how he reluctantly turned a family holiday memory he’d long tried to repress into one of Seinfeld’s most iconic episodes. At the time, he wasn’t convinced it would be well received. “It was embarrassing to me and seemed insane and not in a good, quirky TV way but in, like, a sad creepy dysfunctional way,” he shares. And yet, not only was that episode a hit with audiences, decades later, the holiday lives on. In preparing for the interview, I looked up media mentions for Festivus in our Muck Rack software and found over 3,000 articles have mentioned it in the past 12 months alone. Also in this episode, Dan shares some insider details from his time writing for HBO’s Silicon Valley, where he interviewed start-up founders and entrepreneurs as part of his research. The year the show premiered, HBO sponsored The Shorty Awards, which I co-founded and run, and they invited us to watch the pilot. I remember watching it and thinking, this is so good — it’s so accurate and incisive. After talking with Dan about their research process, I now understand just why it was so realistic. To nail down the Silicon Valley culture, the writers piled into vans and visited various tech companies, where they hit up founders, executives, engineers and VCs for stories. Coincidentally, among those Dan talked with were a couple of past Venture Voice guests, LinkedIn’s Reid Hoffman and my first guest on the podcast, the very funny Dick Costolo, then CEO of FeedBurner. According to Dan, a large percentage of the original Festivus was spent on airing grievances. I’m sure that’s something we can all get into as 2020 comes to a close. But you could probably also use a break about now, so tune in — I think you’re going to have a lot of fun with this one. Happy Festivus! *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com

LinkedIn founder Reid Hoffman was one of my first guests on Venture Voice, back in 2006. Even though LinkedIn had 7.2 million users by then, it was still very much a niche platform and had only 56 employees. Putting your resumé online for all the world to see was pretty uncommon at that time. But Reid was driven by a simple goal: to change the world. Revisiting this interview now, you can pick up on some of the clues as to why he would become so successful. He takes an almost philosophical approach to business, putting himself in the user’s shoes and focusing on creating valuable media objects that would have a transformative effect on society. He also discusses the value of PR, something that stuck with me as I later launched Muck Rack. And he talks a lot about his peers — Mark Pincus, Peter Thiel, Stewart Butterfield — fellow entrepreneurs who hadn’t yet made it big but went on to do big things and continue to support each other. I was a fledgling entrepreneur when I spoke with Reid back in 2006, and these conversations were hugely instructive to me as I was growing my businesses. Between my companies Muck Rack and The Shorty Awards, we’ve now grown to about 100 employees — more than LinkedIn had at that time. I’ve found that I’ve discovered new insights by revisiting this conversation about what a mammoth company like LinkedIn was thinking about when they were first getting started. Listen now for an inside view of LinkedIn on the cusp. *** Thank you to our sponsor SteadyMD. Find out more about them here: steadymd.com/venturevoice If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from. For show notes, past guests and transcripts, visit venturevoice.com Sign up for the Venture Voice email newsletter at venturevoice.substack.com/welcome Follow and connect on social: On Twitter: twitter.com/gregory On Instagram: instagram.com/gregory On YouTube: youtube.com/c/GregoryGalant On LinkedIn: linkedin.com/in/galant/ Learn more about Muck Rack at muckrack.com and The Shorty Awards at shortyawards.com

Mark Cuban has built and sold more than one company and invested in plenty of others, but you might be surprised to learn that what he values most is something a lot of entrepreneurs find much more elusive: time. It’s a lesson this natural-born businessman learned from his father and took to heart at an early age. This episode begins with a trip back to Mark’s early years and explores how he made his first million (and then billion) — and why he continues to be driven by the pursuit of freedom that comes with having control over your own schedule. He also talks about some of his productivity habits, including why 40 unread emails is his limit, and how he uses Muck Rack Alerts to keep track of his press mentions. As someone who’s not shy about talking to the press but who also knows how valuable time is, Mark offers this advice for CEOs: “Some of the best time that you can spend is getting to know people that cover and write about your industry.” Listen in to hear Mark’s journey from a self-described “lousy employee” to billionaire Shark who’s accumulated significant wealth in both time and money.Thank you to our sponsor SteadyMD. Find out more about them here: steadymd.com/venturevoiceIf you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from.For show notes, past guests and transcripts, visit venturevoice.comSign up for the Venture Voice email newsletter at venturevoice.substack.com/welcomeFollow and connect on social:On Twitter: https://twitter.com/gregoryOn Instagram: https://instagram.com/gregoryOn YouTube: https://www.youtube.com/c/GregoryGalant?sub_confirmation=1 On LinkedIn: https://www.linkedin.com/in/galant/ 

Today’s media executives plotting to charge for their content would do well to hear how Larry Kramer beat Jim Cramer’s TheStreet.com by resisting pressure to put most content behind a pay wall while not relying entirely on advertising. To the average consumer, MarketWatch.com…

Any shareholder in a startup can tell you there’s a big difference between paper wealth and cash. Short of an IPO or outright acquisition, there are few options to cash out for the shareholders of even the most thriving private companies.…

“Dial 1 for sales, dial 2 for support…” Ten years ago it cost over $10,000 to get a phone system with the advanced options we’re used to hearing when we call big companies. Having a professional-sounding phone system was a surprisingly big challenge for small businesses short on cash.…

Craigslist seems unbeatable. It’s often blamed (or celebrated) for destroying the classifieds business that helped keep American newspapers afloat. Now second-time Venture Voice guest Fabrice Grinda is seeking to dominate online classifieds with OLX, his latest venture. Unlike Craigslist, OLX is translated into many languages and has a global focus.…

Joel Spolsky first came on Venture Voice over three years ago to discuss his company which he launched in a very different way from most entrepreneurs. Rather than start with the big idea and pay lip service to building a great team, Joel focused on getting great programmers first.…

Graham Hill started the blog TreeHugger to cover green issues in 2003. After a steady climb in traffic and advertising, Graham sold the company to Discovery Communications in 2007 for $10 million. Since launch and even after the acquisition, Graham ran his business virtually.…

It takes only a few seconds to customize a radio station on Pandora. Its founder Tim Westergren has been struggling for almost a decade to make it that way. Pandora was five years in the making before it streamed a single song to a user.…

The title financier conjures images of mahogany desks and million dollar checks for most. But for anyone pitching to David Cohen’s TechStars, the outcome is getting accepted to what’s essentially a summer camp for entrepreneurs in Colorado and being offered a check of $18,000 or less in exchange for 6% of the startup.…

Not to be called a one trick pony, Sam Wyly’s turned himself into a billionaire by starting and growing companies in technology, oil, retail and even in the restaurant industry. Coming from a modest upbringing, Sam worked in sales at IBM and Honeywell before founding University Computing in 1963 at age 29 with just “$1,000 and an idea” as he puts it in his book of that title.…

Jeff Stewart needed that done yesterday. Jeff became an entrepreneur when he founded the web consultancy Square Earth in 1995. Only three years later he became a serial entrepreneur by starting Mimeo, a service that lets you send a file directly from your computer to be printed, bound and shipped overnight.…

Last time Derek Sivers was on Venture Voice three years ago he told us he had to “whack ’em [investors] off with a stick”. Now we know why. Derek announces on our show for the first time the amount he sold his company for this past summer: $22 million.…

Attention entrepreneurs dealing with the current economic downturn: This interview is for you. After working as a journalist for Jason Calacanis at Silicon Alley Reporter, Rafat Ali ended up broke in a market with a dearth of employment opportunities. To try to find a new job, Rafat created paidContent.org…

Whether working with market trends or against them, Frank Addante has found entrepreneurial success. Before he was 29 years old, one of Frank’s companies went public and two were acquired. At his worse, he returned capital to investors. Suffering from serial entrepreneurship, Frank left the Illinois Institute of Technology just four classes shy of his degree.…

The name Tom Perkins is now almost synonymous with venture capital, but it’s clear that he cut his teeth as an entrepreneur. Educated at MIT and Harvard, Perkins first made his mark by managing the initial growth of Hewlett-Packard’s computer business while simultaneously inventing the first cheap and reliable laser.…

Jeremy Stoppelman is the co-founder and CEO of Yelp, a site where users can write and share reviews of local businesses. Everyone’s now a restaurant critic. However, local reviews were not the original focus, but just one of several features in the earlier versions of the site.…

Not many entrepreneurs have a motor like Kevin Ryan’s. Kevin is best known for his work as CEO at the on-line advertising firm DoubleClick, which he grew from a 20 person start-up to the largest Internet company in New York at the height of the dot-com boom.…

Marketing a startup is tricky business. Every entrepreneur faces the dilemma between allocating time to improving the product and marketing the product. If the two can be mixed just right, then perhaps sterile marketing can go viral. We tackle that issue in part 2 of 3 of our very own Venture Voice Startup Workshop coverage in New York City.…

Before the rise of the Internet, cable TV was the new form of distribution remaking the entertainment business. Life-long entrepreneur and former jazz producer Fred Seibert pioneered that field, and is known in the industry for branding MTV (remember their ever-changing animated logo) and Nickelodeon (remember Nick-at-Nite).…

The battery is an afterthought for most inventors. All the fun seems to be in developing a device, not in powering it. But when was the last time you cursed your phone, camera or podcast player because it ran out of batteries?…

Premal Shah believes your last name doesn’t need to be Gates or Rockefeller in order to make a real dent in global poverty. After leaving his job as a Principal Product Manager at PayPal, it has taken Premal less then a year to make good on Kiva’s pledge that all it takes to become a micro lender is a credit card and access to a computer.…

Real business networking takes place in the country club, at the chamber of commerce and on the golf course. After all, the Internet is just for friending strangers on MySpace and poking friends on Facebook. If you said all that to Reid Hoffman, he might think twice about adding you as a contact in LinkedIn, the business networking site he started that connects over seven million professionals.…

If technology entrepreneurs have a guru, it surely must be Guy Kawasaki. For about two decades, Guy’s been advising entrepreneurs in one way or another. First as an evangelist for Apple, he courted software entrepreneurs and developers to write code for the Macintosh.…

There are not many entrepreneurs who have spent their entire 10-year careers starting new ventures in online media, but Jason Calacanis just can’t help himself. Jason rode the dot com wave in New York by starting Silicon Alley Reporter. His publishing company Rising Tide Media grew to $12 million in sales.…

Digg, the news website that uses its own readers rather than editors to decide what stories are most important, has been growing with a fury. While founder Kevin Rose has gotten a lot of attention including a recent cover of BusinessWeek, CEO Jay Adelson has been guiding Digg toward business success.…

If there are best practices in entrepreneurship, you’ll hear the secrets to them in this coverage of the first half of the recent Venture Voice Startup Workshop in New York City. If there are in fact no best practices for entrepreneurs, then you’ll at least enjoy the heated discussion about how entrepreneurs should navigate the startup seas.…

While many restaurants offer dozens of wines, beers and mixed drinks, there are few non-alcoholic options on the menu. Former dot-com entrepreneur and self-described foodie Sharelle Klaus was fed up with her lack of beverage options during the time she was pregnant with her four children.…

What do you do after building and selling a business for $1.5 billion in the course of only a few years? That’s the question David O. Sacks, one of the co-founders of PayPal, faced after eBay bought his company. It didn’t take him long to find the answer: Go to Hollywood and make movies.…

Venture Voice has been illuminating entrepreneurship through the podcast for just short of a year. Now, at the Venture Voice Startup Workshop on June 26 in New York, you can interact with top entrepreneurs and venture capitalists to find out how to start and grow innovative businesses.…

Starting a service aimed at the blogging community is like jumping into a pressure cooker – all of the users are critics and have bullhorns. Good thing David Sifry, the founder of Technorati, has a thick skin he’s built after founding four businesses.…

Being robbed at gun point and being threatened by the mob are not problems the average entrepreneur encounters. Steve Hindy faced these problems and more, but what concerned him most was the fate of his brewery. Steve started the Brooklyn Brewery with Tom Potter.…

Scott Johnson is a long-time entrepreneur on the bleeding edge of technology. He started his first business in 1987 and successfully sold it. Then he rode the dot com wave up and down with Mascot Network, a company that was trying to do what Facebook does now by providing online communities for college students.…

Shoba Purushothaman’s career has shifted dramatically since she started her first job as a business journalist in Malaysia. After spending several years working for the Wall Street Journal and Dow Jones Newswires, she grew restless just covering how the world was changing.…

If you’re making lots of money in a fat industry for doing relatively little, then the last thing you want is a competitor like John C. Bogle. He founded The Vanguard Group in 1975 and revolutionized the mutual fund industry by slashing management fees.…

When a startup launches its first product, should it expect a lot of fanfare? It should if it launches at DEMO before an audience of hundreds that includes some of the nation’s top journalists and venture capitalists (not to mention Venture Voice).…

Kelly Perdew may have won The Apprentice 2, but the listeners of Venture Voice have given him a new recognition for his entrepreneurial work since then. Kelly got the most votes for the Venture Voice 2005 Entrepreneur of the Year Award.…

The listeners have spoken. Jason Fried of 37signals and Joel Spolsky of Fog Creek Software have won Venture Voice Entrepreneurial Achievement Awards. They came in second and third place out of a pack of over 20 world-class entrepreneurs we’ve interviewed on the show (we’ll announce the Venture Voice Entrepreneur of the Year Award winner next week).…

“Stock lockup” is a term remembered with horror by many entrepreneurs who weren’t allowed to sell their dot com shares before the bubble burst. Bo Peabody founded Tripod, which was sold to Lycos for $58 million in stock. The terms of the sale forced him to hold onto his stock for two years — while its value happened to increase ten-fold.…

It’s not easy to stand out at Kleiner Perkins, one of the most prestigious venture capital shops in Silicon Valley that counts Google in its portfolio. Though Randy Komisar joined the firm just this year, it’s clear he’s not a typical venture capitalist.…

We’ve interviewed some of the most accomplished and most hungry entrepreneurs on this show, but now the year’s almost over and it’s time to choose the Entrepreneur of the Year. We have no distinguished panel of judges or wise editorial board to make this decision.…

If you think the ringtone business is for kids, then Fabrice Grinda has a $130 million lesson to teach you. After starting the eBays of Europe and Latin America, Fabrice brought the ringtone business concept to America by starting Zingy. We caught up with Fabrice, now 31 and a millionaire several times over, just a couple of hours before he finished his last day at the helm of Zingy.…

While some entrepreneurs fret over new business ideas, Joel Spolsky of Fog Creek Software focuses on hiring the best and brightest for his New York City-based software company, and then figures out how to make a profit with the products they create.…

Many would-be tech titans dream day and night about how their hot new idea will change the world. Derek Sivers just wanted to have his independent band’s CDs sold over the Web. No one would do it, so he built his own music store.…

At age 28, Mena Trott is a veteran blogger and an accomplished company founder. Six Apart, the business she started four years ago with her husband Ben, now has over 100 employees. Its stable of popular blogging products (including Movable Type, TypePad and LiveJournal) are used by writers of all types — from the most influential bloggers to children who communicate after school.…

The business world seems to keep getting more complicated, but Jason Fried is all about keeping things simple. When founding 37signals, Jason and his two partners staked their careers on simplicity. They wrote a manifesto to convince others of their philosophy of keeping design on the Web simple.…

Dropping out of college to start a technology company is almost a cliché. But is technology the only industry that can seduce an ambitious student into entrepreneurship? Tom Szaky dropped out of Princeton because he saw an opportunity in trash. At 19, he started developing an alternative to Miracle-Gro by using the excrement of worms that eat compost.…

You might expect that if you launched your pride and joy — your startup company — at a conference, it would automatically be the center of attention. At DEMO, the leading technology product launch conference, you’re hatching your business alongside 64 other companies with cool new technologies.…

New businesses usually start small and work slowly and steadily to build their reputation. But that’s not true of startups that choose to launch their product at DEMO, the most prestigious conference dedicated to launching new technologies. Presenters have to agree to be radio silent about the cool technology they’ve been working on night and day for the past several months, if not years, of their lives.…

Entrepreneurs who were doing business in the eighties might still remember IBM for its suits and corporate ways. Now Drew Clark, the co-founder of the IBM Venture Capital Group, has shed his tie and is changing that image. His group is opening up IBM’s vast resources to startups.…

Statistically speaking, Starvest Partners shouldn’t be in business: Few venture capital funds raised in 1998 survived the dot com bust, first-time partners are a huge bet, and no other venture capital firms are run by women. But don’t tell that to Deborah Farrington, the founder and co-chairman of Starvest.…

If you thought you’re an entrepreneur just because you started a software company in Silicon Valley, you’re dead wrong, according to Scott Rafer. It’s just too easy. Scott’s the CEO of San Francisco-based Feedster, an RSS search engine and ad network that allows people to find blogs, jobs and more.…

Some venture capitalists keep a low profile, preciously guard their e-mail addresses from needy entrepreneurs and put on a jacket for publicity photos. Not Brad Feld. Brad started his career building his own technology consulting company with nothing but $10 and a 19-year-old’s ambition.…

While some people still wonder if the fax machine has been rendered obsolete, Jeremy Hague is ready to write e-mail’s obituary. Jeremy’s brand new company, Netralia, recently released a product to rave reviews called Skylook. Many people use Microsoft Outlook to manage their contacts and send e-mail.…

If someone told us to listen to business insights from a former game show contestant back in the day when The Price is Right was the closest thing to a televised business competition, we would have laughed in their face. Since then The Apprentice has attracted many ambitious young professionals to do battle for a spot in the Trump Organization.…

A quick glance at Evan’s bio might make it seem as though he just stumbles into all the newest, hottest trends. However, the only thing Ev stumbled into was traffic (the kind you get on the non-information highway — where he discovered the value of listening to podcasts) on his commute.…

Entrepreneurs need community. This entrepreneur makes communities. An Illinois native, Scott Heiferman came to New York while working for Sony in 1994. He quickly joined the avant-garde of the Silicon Alley community while growing his new media ad agency, i-traffic.…

We covered the past with Joe in our previous show, but it’s clear he spends a lot of time thinking about the future. Many people muse about how they would do things differently if they had only the chance to do it all over again.…

Conventional wisdom tells us to go get a job out of college to learn the ropes, not to take on friends as business partners, and to accept defeat gracefully. Joe Kraus’s business war stories are anything but conventional. Before graduating college, he convinced five of his friends to pass on blue chip job offers to start a business of their own.…

This Internet bad boy doesn’t think he’s so bad, and one of the top venture capital firms agrees to the tune of $4 million. Don’t know who Philip Kaplan of AdBrite is? Well if you were doing anything remotely dot com related in the late 90’s you probably know who Philip Kaplan of F___edCompany.com…

Sick of potential investors not taking your phone calls? Pitch a venture capitalist on his iPod. Dick Costolo of FeedBurner tells us how his CTO did just that in the second and final part of our conversation. (Be sure to check out the first half too if you haven’t already).…

Dick Costolo of FeedBurner joins us for our first show. FeedBurner provides services for publishers of RSS (Really Simple Syndication). RSS is an interface that allows users to access data from blogs, traditional media, podcasts and other sources in the way they want to view it.…