Venture Voice – interviews with entrepreneurs

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.

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For show notes, past guests and transcripts, visit venturevoice.com

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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.

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If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from.

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.

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If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from.

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.

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If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from.

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.

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If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from.

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.

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If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from.

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!

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If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from.

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.

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If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from.

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.

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If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than a minute and helps us continue to attract the entrepreneurs you want to hear and learn from.

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

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.”