$500M CEO: The Simple Mindset Trick for Achieving Your Dreams
Jesse Cole, founder of Banana Ball, shares his journey from sleeping on an air mattress with $268 in a bank account to building a $500M+ entertainment brand by focusing on fan experience over profits. He discusses his philosophy of constantly innovating, maintaining control over the business, and creating shared emotional moments that make people feel alive.
Summary
Jesse Cole recounts his unconventional path to success in professional baseball entertainment. Starting in 2015 with the Savannah Bananas, he and his wife Emily invested over $1 million and lived on an air mattress while building the team from just two ticket sales. Cole's philosophy centers on being 'fans first'—pricing all-inclusive tickets at $15 and avoiding standard revenue extraction methods like ticket fees, sponsorship saturation, and merchandise upselling.
The pivotal moment came in 2018-2020 when Cole began experimenting with what would become Banana Ball, a reinvented version of baseball with non-stop action, trick plays, entertainment, and player engagement. Rather than competing on traditional baseball terms, he studied Walt Disney, PT Barnum, and entertainment pioneers to transform the sport itself. The first official Banana Ball game occurred in 2020 during COVID with just 1,000 fans, but by 2024-2025, the league grew to play in major league stadiums with 40,000-100,000 person crowds, selling 3.4 million tickets annually.
Cole emphasizes several core principles: starting small and dreaming big, constantly iterating and 'plussing the show' like Disney did, working backwards from the feeling he wants to create rather than financial targets, and maintaining complete control to preserve the mission. He refuses all acquisition offers and public investment opportunities because shareholders would inevitably pressure him to prioritize revenue over fan experience. His team now includes 150+ cast members, 160 players across six teams, with full year-round salaries and health insurance—significantly above minor league standards.
Personally, Cole attributes his drive to childhood experiences of isolation and lack of paternal affection, which created a deep fear of irrelevance and need to make people feel 'seen, heard, and that they matter.' His marriage to Emily has evolved as they've taken on foster care and adoption while building the business, requiring constant communication about priorities and shared values. Cole travels extensively but makes deliberate choices to miss games for family time, jumping in pools in full clothes and creating 'moments' with his three young children.
Looking forward, Cole plans the Banana Bowl on Disney platforms as the league's 'WrestleMania moment,' emphasizing that growth will be measured in decades and centuries, not quarters. He refuses to chase arbitrary metrics like 10 million annual tickets if it compromises product quality, instead focusing on international expansion and new seasonal opportunities to reach more fans without diluting the experience. His ultimate vision is creating a billion-person fan base while maintaining the core mission of spreading joy and building something that never gets sold.
Key Insights
- Cole believes that companies which pursue money as the primary objective inevitably lose their mission and drive—citing that once shareholders or private equity are involved, financial extraction replaces fan-centric decision-making, exemplifying this with how other sports leagues add sponsorships, ticket fees, and merchandise upselling that fans resent.
- Cole's fear of boredom and irrelevance stems from childhood isolation as an only child without many friends, which led him to constantly create attention and excitement—a trait he's channeled into building entertainment that obsesses over preventing audience boredom through non-stop content and innovation.
- Cole argues that working backwards from the emotional feeling you want to create (like the shared moment at Clemson where hundreds came together) is more effective than working backwards from financial targets, and this principle guides all his product development decisions.
- Cole contends that obsession is not a character flaw but a fundamental requirement for greatness—noting that every truly great performer or entrepreneur he studies (Michael Jackson, Walt Disney, Taylor Swift) shares an obsessive attention to minute details that others miss or overlook.
- Cole believes that most leagues fail because they compete on the same product (baseball, hockey, football) while chasing sponsors and TV rights, whereas Banana Ball succeeds by creating something entirely new that fans have never experienced before, making traditional competition irrelevant.
Topics
Transcript
[0:00] We thought it was a very good decision [music] for my wife and I to get married and then go into over a million dollars in debt. Sleeping on an airbed, only selling two tickets down to our last [music] dollar was brutal. We ran out of money. Emily turned to me and said, "Jess, we have to sell our house." >> How did you continue to believe in yourself when everyone said no? >> It was chaos. >> He is an entrepreneur, author, and the creator of Banana Ball. >> Transforming traditional baseball into a class-based entertainment experience. Please welcome Jesse Kohl's. [music] >> Almost everyone said you're the craziest person ever. >> I still do. This is…
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