Venture Voice

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

Mon, 7 Dec 2020 14:49:45 +0000 venturevoicegalant@gmail.com (Gregory Galant) http://feedproxy.google.com/~r/vv/~3/0SHSrGKnR_o/jessica-lessin-of-the-information-turned-her-journalism-beat-into-a-business-azAJMEbi Jessica Lessin of The Information turned her journalism beat into a business Gregory Galant 00:52:24 Jessica Lessin is founder, CEO, editor-in-chief and sole owner of The Information, the influential subscription-only tech publication that was launched on a simple idea: write deeply reported articles about the technology industry that people won't find elsewhere. As she shares in this episode, like many who work in the news business, she got the journalism bug early on, working on school papers and enjoying the permission it gives you to “be a little bit nosy.” While at Harvard, she covered the faculty beat for The Harvard Crimson, something she likens to covering Congress. Oh, and there was also “the other thing that was going on” — the launch of Facebook. Jessica went on to cover a new emerging tech beat for The Wall Street Journal, writing about startups and “what the kids were doing online.” But she had trouble convincing editors that companies like Facebook were worth writing about. She says they simply didn’t understand the business models that would ultimately propel these companies. Like many entrepreneurs, Jessica saw an opportunity within a disruptive moment. She was convinced that there was a broad audience for a business publication that focused on deep reporting around technology. As publishers tried to chase a business model based on “eyeballs and clicks,” she decided to develop her own model that would build and monetize audiences based on quality information. Jessica Lessin just celebrated the 7th anniversary of The Information, and it’s clear that her business model and her thesis — that you can’t remove business from the context of technology and disruption — are more relevant than ever. Tune in to hear more about what she learned covering tech startups and how it informed the launch of her own tech news startup. *** 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 Jessica Lessin is founder, CEO, editor-in-chief and sole owner of The Information, the influential subscription-only tech publication that was launched on a simple idea: write deeply reported articles about the technology industry that people won't find elsewhere. As she shares in this episode, like many who work in the news business, she got the journalism bug early on, working on school papers and enjoying the permission it gives you to “be a little bit nosy.” While at Harvard, she covered the faculty beat for The Harvard Crimson, something she likens to covering Congress. Oh, and there was also “the other thing that was going on” — the launch of Facebook. Jessica went on to cover a new emerging tech beat for The Wall Street Journal, writing about startups and “what the kids were doing online.” But she had trouble convincing editors that companies like Facebook were worth writing about. She says they simply didn’t understand the business models that would ultimately propel these companies. Like many entrepreneurs, Jessica saw an opportunity within a disruptive moment. She was convinced that there was a broad audience for a business publication that focused on deep reporting around technology. As publishers tried to chase a business model based on “eyeballs and clicks,” she decided to develop her own model that would build and monetize audiences based on quality information. Jessica Lessin just celebrated the 7th anniversary of The Information, and it’s clear that her business model and her thesis — that you can’t remove business from the context of technology and disruption — are more relevant than ever. Tune in to hear more about what she learned covering tech startups and how it informed the launch of her own tech news startup. *** 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 no full 65 entrepreneur,venture,capital,vc,technology,entrepreneurship,start

Mon, 23 Nov 2020 18:13:07 +0000 venturevoicegalant@gmail.com (Gregory Galant) http://feedproxy.google.com/~r/vv/~3/i2TiFa3InXM/how-john-bogle-started-vanguard-group-and-invented-index-funds-xgVHNy9T How John Bogle started Vanguard Group and invented index funds Gregory Galant 00:55:10 To an entrepreneur, a corrupt industry with a lot of inefficiencies means one thing: There’s a huge opportunity to innovate. When he founded The Vanguard Group in 1975, John Clifton “Jack” Bogle created the first index mutual fund, an idea that was innovative in its simplicity. By keeping management costs low, he was able to pass the savings on to investors. It sounds like common sense, but it goes against the grain of how most mutual fund managers think and operate. In fact, at the time, his idea was ridiculed as “un-American” and “a sure path to mediocrity.” But Jack was undeterred. If anything, he was even more motivated by the naysayers. This interview was recorded in 2006 when Jack was 75, and what stands out is that his idealism and interest in “having the good fight” hadn’t wavered in the slightest. He’d just released his fifth book, “The Battle for the Soul of Capitalism,” and was still relentlessly focused on taking on corruption and abuse in the industry. He wasn’t in it for the fancy perks or the money. He was in it to fight the good fight and to build a better world. Jack passed away in 2019, but his legacy is stronger and more relevant than ever. I feel fortunate to have been able to spend this time with him, both on the mic and off. I think you’ll see why. *** 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 To an entrepreneur, a corrupt industry with a lot of inefficiencies means one thing: There’s a huge opportunity to innovate. When he founded The Vanguard Group in 1975, John Clifton “Jack” Bogle created the first index mutual fund, an idea that was innovative in its simplicity. By keeping management costs low, he was able to pass the savings on to investors. It sounds like common sense, but it goes against the grain of how most mutual fund managers think and operate. In fact, at the time, his idea was ridiculed as “un-American” and “a sure path to mediocrity.” But Jack was undeterred. If anything, he was even more motivated by the naysayers. This interview was recorded in 2006 when Jack was 75, and what stands out is that his idealism and interest in “having the good fight” hadn’t wavered in the slightest. He’d just released his fifth book, “The Battle for the Soul of Capitalism,” and was still relentlessly focused on taking on corruption and abuse in the industry. He wasn’t in it for the fancy perks or the money. He was in it to fight the good fight and to build a better world. Jack passed away in 2019, but his legacy is stronger and more relevant than ever. I feel fortunate to have been able to spend this time with him, both on the mic and off. I think you’ll see why. *** 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 no full 64 entrepreneur,venture,capital,vc,technology,entrepreneurship,start

Mon, 9 Nov 2020 12:58:09 +0000 venturevoicegalant@gmail.com (Gregory Galant) http://feedproxy.google.com/~r/vv/~3/6qhgxw-H_Fk/todd-mckinnons-journey-taking-okta-from-0-to-a-25-billion-public-company-IvQUnasV Todd McKinnon's journey taking Okta from $0 to a $25+ billion public company Gregory Galant 01:06:24 I can still remember logging in to PeopleSoft at my first job to see what deductions had come out of my paycheck. Now, all these years later, I’m interviewing the man who wrote that very code. Todd McKinnon, my guest on this episode of Venture Voice, began his career at PeopleSoft before moving on to Salesforce and ultimately founding Okta. Todd’s company is now worth over $25 billion. This episode takes you on Todd’s entrepreneurial journey, from the Powerpoint deck he presented to his wife (subtitle: “Why I’m not crazy” for quitting my job at Salesforce) to the initial product idea (with a name that sounded “like a French perfume”) to successfully completing an IPO. Listen now on Apple Podcasts. “You had to be able to have enough confidence that you’d be able to build this iconic tech company around this initial idea. A lot of initial ideas — people will pay for them but they don’t have that long-term staying power. They become a feature.” Todd McKinnon is the founder and CEO of Okta, a $25 billion publicly traded software company that you may never have heard of, but it solves one of the most annoying 21st century problems: having to remember all of your various log-ins and passwords. Thousands of companies use Okta Identity Cloud to manage access and authentication for their employees. I can relate to Todd’s experiences as a scrappy entrepreneur and the challenges of founding and growing a business. My job as CEO has changed tremendously as my own companies, Muck Rack and The Shorty Awards, have grown from just a few employees to about a hundred today. I wanted to learn how Todd scaled to thousands of employees. “I think I try to combine the best parts of Salesforce and the best parts of PeopleSoft and throw in a little bit of my personality on the side, and let the chips fall where they fall.” As you’ll hear in this episode, Todd got his first taste of what technology can do for customers while working at PeopleSoft. From there, he moved on to Salesforce, where he had a front-row seat to the early days of SaaS — as well as the opportunity to work for Mark Benioff before he became a multi-billionaire. Todd was the first person to lead the Salesforce engineering team, scaling it from just over a dozen people to hundreds. Those professional experiences and the cultures of the two companies would stick with him and inspire many of the decisions he made as he embarked on his own start-up journey. “There was part of me that wanted to be the boss, and part of me that wanted to attack the challenge of creating a company from scratch, knowing that the odds are very long… I couldn’t be the person who didn’t take a shot.” Todd points out that whenever there’s a big disruptive technical shift — like the transition to the cloud — there’s an opening to build a new business. And young companies, which don’t have all the baggage of the bigger, more established players, are often better positioned to take advantage of that opportunity. Still, the odds are long. So when he sat down to sell his wife on the idea of quitting his very good job at Salesforce to start his own company, he says he “did what anyone would do, you know. I wrote her a PowerPoint deck presentation.” The deck included nine slides that explained how, when it didn’t work out, he could just get another job. Fortunately, though, he didn’t end up having to fall back on Plan B. “As a CEO, my decision-making process really slowed down…you have to make sure that you get involved in the right decisions, you don’t overly involve yourself in all of them. And you have to be ready to make them.” Now matter how much experience and insight you have from working as a leader in a big company, you’re going to encounter a steep learning curve once you start scaling your own business as its CEO. I was interested to hear how Todd adjusted to that role and how he grew into the job. As he shares, he had some good advisers on his side, but he also had to face the reality that he didn’t have all the answers — and that not having all the answers was ultimately a good thing. It helped him build the kind of collaborative culture he wanted, where employees have a stake in the decisions. “It was very important that the company, while we celebrated [going public], that the company didn’t use it as a reason to stop pushing or a reason to be satisfied.” Todd likes to compare the experience of going through an IPO to high school graduation. It’s a rite of passage, but you don’t want it to be the best day of your life. Like many entrepreneurs, Todd is motivated by challenge, and he is always on the lookout for the next big wave on the horizon. While it was challenging to build a successful business, he’s energized by the thought that the biggest challenges are still ahead of him — and so is the opportunity to build “an iconic technology company that will be remembered for decades in the future.” I can still remember logging in to PeopleSoft at my first job to see what deductions had come out of my paycheck. Now, all these years later, I’m interviewing the man who wrote that very code. Todd McKinnon, my guest on this episode of Venture Voice, began his career at PeopleSoft before moving on to Salesforce and ultimately founding Okta. Todd’s company is now worth over $25 billion. This episode takes you on Todd’s entrepreneurial journey, from the Powerpoint deck he presented to his wife (subtitle: “Why I’m not crazy” for quitting my job at Salesforce) to the initial product idea (with a name that sounded “like a French perfume”) to successfully completing an IPO. Listen now on Apple Podcasts. “You had to be able to have enough confidence that you’d be able to build this iconic tech company around this initial idea. A lot of initial ideas — people will pay for them but they don’t have that long-term staying power. They become a feature.” Todd McKinnon is the founder and CEO of Okta, a $25 billion publicly traded software company that you may never have heard of, but it solves one of the most annoying 21st century problems: having to remember all of your various log-ins and passwords. Thousands of companies use Okta Identity Cloud to manage access and authentication for their employees. I can relate to Todd’s experiences as a scrappy entrepreneur and the challenges of founding and growing a business. My job as CEO has changed tremendously as my own companies, Muck Rack and The Shorty Awards, have grown from just a few employees to about a hundred today. I wanted to learn how Todd scaled to thousands of employees. “I think I try to combine the best parts of Salesforce and the best parts of PeopleSoft and throw in a little bit of my personality on the side, and let the chips fall where they fall.” As you’ll hear in this episode, Todd got his first taste of what technology can do for customers while working at PeopleSoft. From there, he moved on to Salesforce, where he had a front-row seat to the early days of SaaS — as well as the opportunity to work for Mark Benioff before he became a multi-billionaire. Todd was the first person to lead the Salesforce engineering team, scaling it from just over a dozen people to hundreds. Those professional experiences and the cultures of the two companies would stick with him and inspire many of the decisions he made as he embarked on his own start-up journey. “There was part of me that wanted to be the boss, and part of me that wanted to attack the challenge of creating a company from scratch, knowing that the odds are very long… I couldn’t be the person who didn’t take a shot.” Todd points out that whenever there’s a big disruptive technical shift — like the transition to the cloud — there’s an opening to build a new business. And young companies, which don’t have all the baggage of the bigger, more established players, are often better positioned to take advantage of that opportunity. Still, the odds are long. So when he sat down to sell his wife on the idea of quitting his very good job at Salesforce to start his own company, he says he “did what anyone would do, you know. I wrote her a PowerPoint deck presentation.” The deck included nine slides that explained how, when it didn’t work out, he could just get another job. Fortunately, though, he didn’t end up having to fall back on Plan B. “As a CEO, my decision-making process really slowed down…you have to make sure that you get involved in the right decisions, you don’t overly involve yourself in all of them. And you have to be ready to make them.” Now matter how much experience and insight you have from working as a leader in a big company, you’re going to encounter a steep learning curve once you start scaling your own business as its CEO. I was interested to hear how Todd adjusted to that role and how he grew into the job. As he shares, he had some good advisers on his side, but he also had to face the reality that he didn’t have all the answers — and that not having all the answers was ultimately a good thing. It helped him build the kind of collaborative culture he wanted, where employees have a stake in the decisions. “It was very important that the company, while we celebrated [going public], that the company didn’t use it as a reason to stop pushing or a reason to be satisfied.” Todd likes to compare the experience of going through an IPO to high school graduation. It’s a rite of passage, but you don’t want it to be the best day of your life. Like many entrepreneurs, Todd is motivated by challenge, and he is always on the lookout for the next big wave on the horizon. While it was challenging to build a successful business, he’s energized by the thought that the biggest challenges are still ahead of him — and so is the opportunity to build “an iconic technology company that will be remembered for decades in the future.” no full 63 entrepreneur,venture,capital,vc,technology,entrepreneurship,s

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…

Download the MP3. 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 seemed to have come out of nowhere during the late 1990s to quickly establish itself as one of the leading sources of online financial information. For MarketWatch founder Larry Kramer, it represented the last chapter of his 15 year journey as a first-time entrepreneur. Larry started his career as a journalist, going from reporter to the top editor of the San Francisco Examiner in just 10 years with stops at the Washington Post and Trenton Times along the way. Larry founded DataSport Inc. (the company that would eventually morph into MarketWatch though a series of mergers and partnerships) with $500,000 from friends and family. He almost ran out of money early on. After a wild ride on the public market, Larry sold MarketWatch to Dow Jones for over $500 million in 2004 and went on to become the president of CBS Digital Media until 2006. Hear how Larry lived though two different careers and what he's planning next.

Download the MP3. 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. Barry Silbert is determined to change that with his company SecondMarket -- an exchange like the NASDAQ for private stock and other illiquid assets. He founded the company in 2004 focused on restricted stock, and quickly reached profitability with only $350,000 in angel funding. The road to this point was not without challenges; Barry's business partner was diagnosed with cancer and passed away as they were establishing the company. In 2008, SecondMarket made $20 million in revenue. Barry's success has not tempered his ambition as he's spent 2009 aggressively moving into new asset classes such as private companies (Facebook stock is already being traded on his platform), limited partner interest in venture capital firms and even California IOUs. Hear how this former bankruptcy banker did it and why he believes "The sky's the limit" for his business.

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.…

Download the MP3. "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. Enter Siamak Taghaddos and David Hauser who launched GotVMail to offer that service at rates starting at only $10 per month in 2003 as they were graduating college. They launched their business with under $200,000 in capital and never raised any more money. They bootstrapped their way to profitability quickly, and are now driving over $10 million in annual revenue. Despite their success, Siamak and David don't believe what's gotten them this far will take them to the next level. So they've just rebranded their company Grasshopper and are getting ready to launch some new products. Show sponsor: FreshBooks - an easy online invoicing provider used by Venture Voice

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.…

Download the MP3. 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. OLX is completely ad supported so there are no fees for job or real estate listings as there are on Craigslist. Still, it sounds crazy to compete with Craigslist. If anyone can do it, it may be Fabrice. When we interviewed him in December, 2005, it was on his last day working as CEO at Zingy, a ring tone provider that he founded and sold for $80 million against all odds. OLX already has 125 employees and 60 million unique visitors per month, but with $28.5 million is venture capital it has a lot of growth ahead of it before it's a success. Hear how Fabrice plans on getting there. Show sponsor: FreshBooks - an easy online invoicing provider used by Venture Voice

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.…

Download the MP3. 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. Graham lived in different cities from New York to Barcelona while working many hours to grow his company. His team of writers, ad sales people and developers chatted over Skype, got paid through PayPal and used Google documents to collaborate. Simultaneously, Graham launched a ceramic version of the iconic New York paper coffee cup (video below). Listen to how Graham built his businesses without an office or home town. Show sponsor: FreshBooks - an easy online invoicing provider used by Venture Voice

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.…

Download the MP3. 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. For over two of those years the company was completely broke. While Tim convinced employees to defer over $1 million in salaries, Pandora underwent several changes in name, product and revenue models. Now Pandora is a leading online radio destination that’s starting to bring in sizable ad revenue. Tim is still battling with the record industry for its survival. Show sponsor: FreshBooks - an easy online invoicing provider used by Venture Voice

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.…

Download the MP3. 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. This two year old program is part of a new trend in structured angel investing and mentoring that was started by Paul Graham's Y Combinator. Two companies founded at TechStars have already been acquired: socialthing! was sold to AOL and Intense Debate was sold to Automattic (the makers of WordPress). David tells his own stories of success and failure as an entrepreneur, and his transiton to becoming an angel investor. Show sponsor: FreshBooks - an easy online invoicing provider used by Venture Voice

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.…

Download the MP3. 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. The company IPOed and grew to over 5,000 people. Sam hired CEOs and stayed an entrepreneur. He's founded and acquired numerous companies including Bonanza Steakhouse (grew to 600 restaurants), Earth Resources Company, Sterling Software (sold for $3.3 billion), Sterling Commerce (sold for $4 billion), arts-and-crafts chain Michaels (sold for $6 billion), Maverick Capital (a hedge fund with over $10 billion under management) and clean-energy producer Green Mountain Energy. Despite being soft-spoken, Sam's fought and won several high profile proxy fights. Sam's been undeterred as several of his ventures have had visible failures over the years and he's lost audacious bids to take over Western Union and Computer Associates. On the whole, Sam's created a huge amount of value that's put him on the Forbes list of the 400 richest people. Hear how he does it. Show sponsor: FreshBooks - an easy online invoicing provider used by Venture Voice

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.…

Download the MP3. 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. Mimeo struggled in the dot com crash of 2000-2001 just as it was getting off the ground. Jeff was able to pull Mimeo though the downturn despite almost running out of cash, which has allowed the company to flourish and make $55.4 million in 2007 revenues. Ironically, Jeff didn't have the same success in good economic times with ample cash after he raised $20 million for Monitor110. He discusses the company's shutdown and lessons learned. Now Jeff's focused on allowing businesses to hire good salespeople faster with Urgent Career. He announces on this show for the first time that he's just raised a six-figure angel round to speed up Urgent Career's success.

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.…

Download the MP3. 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. Derek owned 100% of the equity. Though he might have made more money than most of his fellow music entrepreneurs, Derek's no Gordon Gekko. In this interview, Derek tells us how he put all of his money from the sale into a charitable trust, that he didn't even visit CD Baby's office once during the last year he owned it, and what he's up to next. Want more Venture Voice? Become a Venture Voice member or contact us about sponsoring the show.

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…

Download the MP3. 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 as an "interactive resume." Luckily, no one hired him. From these humble beginnings, Rafat bootstrapped his blog holding company, ContentNext Media, for four years before taking a small investment from famed media investor Alan Patricof in June 2006. From its inception paidContent has doubled revenues each year and was recently acquired by UK-based Guardian Media Group for a rumored $30 million. Listen in as Rafat outlines the past, present, and future of online media, while sharing his war stories from another uncertain economic time.

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.…

Download the MP3. 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. His companies range from an early search engine to a Sequoia Capital-backed enterprise email solution. Now Frank aspires to be a web publisher’s best friend with his new ad network optimization service that he says is boosting their clients' revenues by 30-300%. Listen in as Frank details his ongoing entrepreneurial journey.

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.…

Download the MP3. 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. The company he built around the laser, University Laboratories, made him independently wealthy and allowed for the creation of Kleiner Perkins, one of the most successful venture capital firms in existence. Kleiner Perkins (now Kleiner Perkins Caufield & Byers) has funded a wide range of well known and wildly successful companies including Google, AOL, Genentech, Sun Microsystems, Compaq, and Tandem Computers. Though Tom's wowed the business press for much of his career, later in life he's gained national attention for having a key role in 2006 Hewlett-Packard board controversy, briefly marrying Danielle Steel, and building the world's largest privately owned sailing yacht. Tom has recently stepped back into the media spotlight by publishing a memoir called Valley Boy: The Education of Tom Perkins. Listen in as he discusses his journey from New York to Boston to Silicon Valley, the creation of Kleiner Perkins, and his advice for the entrepreneurs of the future.

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.…

Download the MP3. 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. Noticing the growth of this buried feature, Yelp re-tooled the site around reviews and hasn't looked back since. Does this story sound familiar? Jeremy's the former VP of Engineering at PayPal, which also had to drastically alter its business early in its life. Listen in to hear Jeremy's thoughts on growing a local enterprise, giving users and identity, and how to recognize and act upon the need for change.