The CEO Series

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.

In this episode of The CEO Series, William Salvi sits down with Jake Karls, co-founder and Chief Rainmaker of Mid-Day Squares. Jake walks through the early version of the business which was three people making 50 to 100 bars a day in a condo kitchen and hand delivering samples with a Polaroid and a handwritten note. He explains how they raised money and built their own manufacturer. Jake talks about why he doesn't believe he is a good manager, his burnout, pitching to Wall Street in shorts and a buttoned down shirt and why after 8 years he still does therapy with his co-founders. He also gets into what it actually takes to get a CPG product into stores, from showing up to trade shows and road shows to using storytelling and social media to drive sales.

In this episode of The CEO Series, William Salvi sits down with Danny Winer, co-founder and CEO of HexClad. Danny traces his path from studying theater and film at NYU and moving to Los Angeles with $2,000 and three suitcases, to a car accident at 28 that broke his back, shattered his right leg, and left him six figures in debt with no ability to work. He rebuilt by selling cookware at trade shows, then lost his first company, Juicepresso, in September 2016 at age 50.

What became HexClad started in the basement hallway of a trade show in Guangzhou, where Danny spotted hexagons lasered onto a Korean barbecue plate and found the rare thing nobody finds at those shows: the actual inventor, holding a book of 13 patents. They talk about the handshake deal that gave an unknown American company US exclusivity, why every investor turned him down for refusing to sell into retail, the emptied retirement accounts and rolling stack of credit cards, and the single Costco test store that saved the company when it was months from going out of business.

They also get into celebrity partnerships. Gordon Ramsay found HexClad by following them on Instagram, and Danny explains what his business manager meant by "you're going to get more than you bargained for," why Gordon is on weekly calls looking at numbers rather than just filming ads, and what happens when he does not like a product. Plus becoming the official cookware of the New York Yankees, the F1 work, and how a conversation with Jimmy Iovine turned a martini shaker into a collaboration with Dr. Dre and Snoop Dogg.

In this episode of The CEO Series, William Salvi sits down with Kevin Hartz and Julia Hartz, Co-Founders of Eventbrite. Kevin traces his path from the early days of Silicon Valley to co-founding Xoom, a money remittance company that became one of the first developers on the PayPal API and was ultimately acquired by PayPal in 2015 for $1.1 billion.

Julia shares how she left a career in television development at MTV and FX to co-found Eventbrite with Kevin. Together they built Eventbrite into one of the world's leading live events platforms, took it public in 2018, and sold it in April 2026 for $500 million.

In this conversation they talk about what it actually takes to build a company with the person you are married to, how they handled investors who told them flat out they would not back a husband and wife team, and what happened when COVID turned Eventbrite from a $5 billion GMV company to negative revenue in 14 days.

They also get into the real overhead cost of running a publicly traded company, why Kevin believes selling Xoom when he did was a $10 to $20 billion mistake in hindsight, what Julia honestly does not know about what comes next, and their unfiltered takes on AI, the current investment cycle, and whether we are heading into a bubble.

In this episode of The CEO Series, William Salvi sits down with Nigel Morris, Co-Founder and Managing Partner of QED Investors and Co-Founder of Capital One. Nigel traces the origins of Capital One, from a working class childhood in England with a military father who moved the family 11 times, to building one of the most disruptive financial services companies in history. He recounts how he and Rich Fairbank identified that the biggest banks in America were making billion dollar decisions by gut instinct rather than data, and how being rejected by 25 banks only strengthened their conviction to prove them wrong. He discusses the regulatory crisis of 2002 that caused Capital One's stock to drop 40% overnight, what it felt like to carry his net worth statement in his briefcase for a year before leaving the company he built, and why the only sustainable advantage in any business is culture. Nigel also shares his philosophy on venture capital at QED, why fintech is a force for social good, and why he believes artificial intelligence will kill jobs while simultaneously creating opportunities we cannot yet conceive of.

In this episode of The CEO Series, William Salvi sits down with Nigel Morris, Co-Founder and Managing Partner of QED Investors and Co-Founder of Capital One.

Nigel traces the origins of Capital One, from a working class childhood in England with a military father who moved the family 11 times, to building one of the most disruptive financial services companies in history. He recounts how he and Rich Fairbank identified that the biggest banks in America were making billion dollar decisions by gut instinct rather than data, and how being rejected by 25 banks only strengthened their conviction to prove them wrong.

He discusses the regulatory crisis of 2002 that caused Capital One's stock to drop 40% overnight, what it felt like to carry his net worth statement in his briefcase for a year before leaving the company he built, and why the only sustainable advantage in any business is culture.

Nigel also shares his philosophy on venture capital at QED, why fintech is a force for social good, and why he believes artificial intelligence will kill jobs while simultaneously creating opportunities we cannot yet conceive of.

In this episode of The CEO Series, William Salvi sits down with Jim Hagedorn, CEO of ScottsMiracle-Gro.

Hagedorn opens up about the most turbulent chapter of his career: a $2 billion gamble on the cannabis industry that nearly ran the company into the ground. He discusses the intense pressure of "burning money," the isolation of leadership during a crisis, and the difficult reality of cutting hundreds of millions in operating expenses to keep the business afloat.

Hagedorn also shares insights into his unconventional path to CEO, from running away from home at 15 to join a commune to flying F-16s in the Air Force. He reflects on the "ruthless" but influential relationship with his father, Horace Hagedorn, and how he eventually spearheaded the massive deal between Scotts and Miracle-Gro.