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Lewis HowesLewis Howes

$500M CEO: The Simple Mindset Trick for Achieving Your Dreams | Jesse Cole

He slept in his socks on a garage floor because it was too filthy to touch. That was Jesse Cole eight years ago, broke, sleeping on an air mattress, betting everything on a wooden bat baseball team nobody wanted.

Jesse ColeguestLewis Howeshost
Aug 5, 20261h 47mWatch on YouTube ↗

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At a glance

WHAT IT’S REALLY ABOUT

Jesse Cole on building Banana Ball through fans-first obsession and iteration

  1. Jesse Cole explains how his boredom with traditional baseball and obsession with nonstop entertainment led him to experiment for years before reshaping the game into Banana Ball.
  2. He describes early financial hardship—selling only two tickets, running out of money, selling his house, and going over $1 million into debt—while staying committed to building a fan-first experience.
  3. He outlines how Banana Ball emerged through testing new rules in low-stakes settings, escalating to COVID-era experiments, road tours, and continuous iteration as the show scaled.
  4. He details the organization’s focus on “winning the upper deck” and making the pre-show a major part of the fan experience through early arrival programming, player interaction, and stadium-wide activations.
  5. He shares how foster care and adoption became central to his family and mission, and why he believes staying private and refusing to sell protects the company’s ability to prioritize fans over financial extraction.

IDEAS WORTH REMEMBERING

5 ideas

Long-term experimentation built the foundation for Banana Ball.

He describes spending a decade running a small team in North Carolina with little media attention, using it as a “laboratory” to test promotions and fan engagement until attendance grew significantly.

Improving the main product mattered more than adding extra “condiments.”

He says that while the surrounding entertainment improved the experience, the core “product” (the game itself) still caused fans to leave early, which pushed him to redesign the rules and pace.

Iteration—through public imperfection—was the path to a better show.

He explains that early Banana Ball tests were confusing and messy (including rule chaos during COVID), but the key signal was that fans stayed until the end, and the team kept iterating year after year.

The pre-show is treated as the main event, not an add-on.

He describes designing the day so fans arrive hours early for rope drop, player autographs, stage shows, and a march through the crowd, because he believes the experience before the game sets the tone for everything that follows.

Belief came from commitment to a vision he personally wanted to experience.

He recounts going more than $1 million into debt after buying the team, running out of money, selling their house, and living on an air bed, while continuing to bet on creating joy and a different kind of entertainment experience.

WORDS WORTH SAVING

5 quotes

We thought it was a very good decision for my wife and I to get married and then go into over a million dollars in debt.

— Jesse Cole

No one leaves a great movie in the middle.

— Jesse Cole

No one gets excited about normal.

— Jesse Cole

I will never doubt anything.

— Jesse Cole

The day I come home and they don't run out.

— Jesse Cole

Read the available transcript
Early financial hardship and debtTesting and iterating Banana Ball rulesEliminating “boring” parts of baseballFans-first business philosophyPre-show programming and stadium activationsScaling teams and maintaining quality controlFoster care, adoption, and family purpose

SPEAKERS

  • Jesse Cole

    guest

    Founder of the Savannah Bananas and creator of Banana Ball, known for his yellow tux and fan-first entertainment approach.

  • Lewis Howes

    host

    Host of The School of Greatness and interviewer who leads conversations with entrepreneurs, athletes, and authors.

High quality AI-generated summary created from speaker-labeled transcript.

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