The CEO Series

In this episode of The CEO Series, Will sits down with Johnny Hillbrant Partridge, the creator behind PE Guy. Johnny talks about growing up in Winnetka, studying business at the University of Denver, and taking classes at Second City and UCB.
He also looks back on working at The Ellen DeGeneres Show and teaching at SoulCycle before content became his full-time job. He walks through the "guy you get stuck talking to at a wedding" video that started PE Guy, why he gave the character a career in private equity, and how he crowdsources intel from his DMs to write videos. 
He also covers running the business with no staff, his $5,000 first brand deal, the thousands of personalized videos he's made, and how brand deals work. He shares his views on private equity, the wealth gap, and satire's role in American capitalism, and answers audience questions.

In this episode of The CEO Series, Will sits down with Lossdog co-founder and CEO Tom Sosnoff.
Tom talks about starting on Wall Street in 1980, moving to Chicago to trade on the CBOE floor, and meeting Scott Sheridan, his business partner of nearly 40 years. He walks through building and selling thinkorswim and tastytrade, including the three-way trade with the Ricketts family that closed the thinkorswim deal.
He also covers the $3 million investment that turned Zero Hash around, what he's building now at Lossdog, and why he and Scott gave $50 million to their employees after their exits.
He shares his views on CEO pay, the wealth gap, and American capitalism, and gets into his trading philosophy, the biggest mistake people make in the stock market, and why he'd rather follow people who are always wrong.

In this episode of The CEO Series, Will sits down with Spin Master co-founder and chairman Ronnen Harary. Ronnen walks through the early days of the company, including Earth Buddy, Devil Sticks, and Air Hogs.
He also gets into the boom and bust of Bakugan, when sales went from $450 million to a billion and back again. He points to hubris as the real cause and explains how that period led directly to Paw Patrol. He tells the full story of Paw Patrol's inception. He talks about writing his book, No Experience Necessary, and opens up about his dysgraphia, growing up with emotional neglect, and the gifts that came with both.
He also covers why he prefers running a public company to a private one, the decision to step down as co-CEO in 2021, the sabbatical that took him from Cape Town to Nairobi, what tariffs did to the toy industry last year, and why physical toys are growing rather than shrinking in an AI world.
He closes on the perception of wealth and business leaders, why he finds the billionaire framing distasteful, his views on monopolies and free markets, voting with your wallet, and the simplest way to get equity in anything.

In this episode of The CEO Series, Will sits down with Chess.com CEO Erik Allebest.
Erik walks through the early days of Chess.com and the two chess businesses he ran before it. He talks about the company's slow, steady growth for over a decade, the surge that came with COVID and Queen's Gambit, and the playbook they built afterward for getting chess into the cultural conversation.
He also covers the second spike in 2023, driven by the Hans Niemann lawsuit, short form video, and chess taking off in schools.
He talks about his role as CEO, why he still does it after 20 years, and his view on capitalism, the negative perception of CEOs, and how he tries to make that change inside his own company first.
He also gets into the cheating controversy involving Hans Niemann and Magnus Carlsen, the report Chess.com published, and how he feels he was portrayed in the Netflix documentary.

In this episode of The CEO Series, Will travels to Vermont to sit down with Alex Roberts, CEO of WhistlePig Whiskey, at the WhistlePig farm.
Alex explains how he went from working as a 24-year-old investment banking analyst on a potential sale of WhistlePig to being offered the CFO job himself. He talks about entering the company with no operating experience, dealing with imposter syndrome and the blunt feedback from his CEO that forced him to rethink how he was adding value. Eight years later, Alex became CEO.
He walks through the transition from CFO to CEO, why he restructured the company within his first weeks in the role and what he has learned about making difficult decisions, building an executive team and more. Alex also breaks down how WhistlePig grew roughly 5x during his time with the company, what it actually takes to grow a premium whiskey brand and why bartenders have played such an important role in WhistlePig's strategy. 
They get into declining alcohol consumption, Gen Z, marijuana, affordability, AI eliminating jobs, tariffs and why Alex believes being a private company gives WhistlePig an advantage. After the conversation, Will tours the farm and distillery and meets the pigs and Highland cows.