Venture Voice – interviews with entrepreneurs

Matt Mullenweg built Automattic into a $7.5B company

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 o...

David Cohen’s Techstars

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 an...

Henrik Werdelin’s Bark fetches $1.6 billion valuation

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 ...

Fabrice Grinda on growing Zingy into a $200 million business

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 a...

Guy Kawasaki’s evangelizing Canva

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 c...

How Derek Sivers decided to sell CD Baby

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 t...

LivePerson’s Robert LoCascio got in mental shape to build a $3.5 billion business

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....

How Tom Perkins pioneered venture capital in 1972

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...

Shutterstock’s Jon Oringer Turned His Amateur Photos Into a $3 Billion Business

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 ...

Curative founder Fred Turner’s fast pivot into COVID-19 testing

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,...

How DRY Soda founder Sharelle Klaus pioneered the culinary soda category

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 fo...

How Amanda Hesser cooked up success with Food52

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 i...

How Mike McDerment grew FreshBooks

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 em...

How Mike McDermott grew FreshBooks

Sometimes, a big mistake can trigger a big idea. In 2003, Mike McDermott 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 em...

How journalist Steve Hindy started Brooklyn Brewery

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 ...

How Mark Wilson built his success by building up others’

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 $8...

How Evan Williams turned side projects like Twitter into huge successes

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 p...

Dan O’Keefe on the founding of Festivus and secrets of HBO’s Silicon Valley

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 ...

Jessica Lessin of The Information turned her journalism beat into a business

How John Bogle started Vanguard Group and invented index funds

Todd McKinnon's journey taking Okta from $0 to a $25+ billion public company

How Reid Hoffman convinced us to put our resumes online

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 ap...

Why Mark Cuban ditched his watch after selling his company

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 freed...

VV Show #60 - Larry Kramer of MarketWatch

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...

VV Show #60 – Larry Kramer of MarketWatch

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 …

VV Show #59 - Barry Silbert of SecondMarket

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 profitabi...

VV Show #59- Barry Silbert of SecondMarket

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. …

VV Show #58 - Siamak Taghaddos and David Hauser of Grasshopper

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 busi...

VV Show #58 – Siamak Taghaddos and David Hauser of Grasshopper

“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. …

What Venture Capitalists Are Really Thinking

I cofounded a company called Sawhorse Media that's making sense of Twitter (Twitter was founded by past Venture Voice guest Ev Williams). We decided to launch a new site called Venture Maven to make it easy to follow what VCs and angels are tweeting about. For example, if you were pitching Spark Capital, you could have checked Venture Maven yesterday to see one partner was at the dentist and a principal just got off painkillers after a knee surgery. Better open the meeting with a good joke....

VV Show #57 - Fabrice Grinda of OLX

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 sou...

VV Show #57 – Fabrice Grinda of OLX

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. …

VV Show #56 – Joel Spolsky of Fog Creek Software

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. …

VV Show #56 - Joel Spolsky of Fog Creek Software

Download the MP3. 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. The ideas came second. Good thing because his big idea, a content management system called City Desk, never took off. Instead it was his small idea, software to track bugs in other software call...

VV Show #55 – Graham Hill of TreeHugger

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. …

VV Show #55 - Graham Hill of TreeHugger

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 PayPa...

VV Show #54 – Tim Westergren of Pandora

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. …

VV Show #54 - Tim Westergren of Pandora

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 ...

VV Show #53 – David Cohen of TechStars

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. …

VV Show #53 - David Cohen of TechStars

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 fo...

VV Show #52 – Sam Wyly of Maverick Capital, Green Mountain Energy, Michaels Stores and Sterling Software

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. …

VV Show #52 - Sam Wyly of Maverick Capital, Green Mountain Energy, Michaels Stores and Sterling Software

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 f...

VV Show #51 – Jeff Stewart of Mimeo, Monitor110 and Urgent Career

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. …

VV Show #51 - Jeff Stewart of Mimeo, Monitor110 and Urgent Career

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 c...

VV Show #50 – Derek Sivers of CD Baby and Muckwork

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. …

VV Show #50 - Derek Sivers of CD Baby and Muckwork

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 ch...

Angel Financing Without Hellish Legal Fees

It's great to hear stories like the one where Andy Bechtolsheim handed the Google founders a $100,000 check before they even set up their bank account. Convince an angel to invest and you're off to the races! However, what many aspiring entrepreneurs don't know is that after the one or two page term sheet there are dozens of pages of documents that go into even an angel financing. Since law firms have templates for these deals you might think it's no harder than copying and pasting. The pr...

VV Show #49 – Rafat Ali of paidContent and contentNext

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 …

VV Show #49 - Rafat Ali of paidContent and contentNext

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 befor...

Uncensored Interview

The folks at Uncensored Interview were nice enough to turn the tables on me by interviewing me on their show. You can watch all the clips here. Here's me talking about what makes a good interview: Please join our new Venture Voice Facebook Page.