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.

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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.

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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.

***

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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.

***

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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.

***

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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.

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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.

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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.

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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!

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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.

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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.

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