Overview of Always be the challenger, with Savannah Bananas founder Jesse Cole
This episode of Masters of Scale features Jesse Cole, founder of the Savannah Bananas and Fans First Entertainment, on how he built one of the most unusual and beloved sports brands in the world. Cole explains how a lifelong love of baseball, an obsession with fan delight, and a willingness to break the “rules” helped him transform a struggling college summer team into a national phenomenon. The core lesson: stay a challenger, keep experimenting, and build every decision around the customer experience.
Key Takeaways
- Fan-first beats traditional business logic when the mission is to create unforgettable experiences.
- Experimentation is a system, not a one-off tactic. The Bananas treat idea generation like a creative production pipeline.
- Challenger mindset matters even after success. Cole says the fear of becoming complacent keeps the organization sharp.
- Joy is a business strategy. The emotional response of fans and staff is central to the brand’s growth.
- Scale comes from making the product remarkable enough that people want to share it. The Bananas spend little on traditional marketing and instead invest heavily in the show itself.
Jesse Cole’s Origin Story
A childhood moment that changed everything
Cole describes being a shy, introverted kid who went to a Red Sox game and had a memorable interaction with pitcher Luis Tiant. Tiant spent time with him in the dugout, and that simple act of attention made baseball feel magical. Cole says it planted the seed for everything he would later build.
From player to front-office innovator
An injury ended his playing career, but it led him into baseball operations, where he realized the front office could shape the fan experience. That insight eventually became the foundation for the Savannah Bananas and the broader Fans First philosophy.
How the Savannah Bananas Were Built
Start small, dream big
Cole says the Bananas began with almost no money, a tiny bank balance, and significant debt. Early on, they sold only a couple tickets and had to fight for survival. But they kept testing ideas and improving the experience.
Turning baseball into a show
Instead of treating baseball as a rigid sport with fixed expectations, Cole reimagined it as entertainment:
- shorter, faster-paced games
- music, dancing, and on-field antics
- themed promotions and unusual events
- a constant sense that “something unexpected” might happen
He credits this willingness to invent with creating Banana Ball, a version of baseball designed to keep fans engaged every second.
A model inspired by creators, not just sports teams
Cole draws inspiration from:
- P.T. Barnum — promotion and showmanship
- Walt Disney — experience design
- The Grateful Dead — direct connection with fans
- WWE/Vince McMahon — spectacle and entertainment
Core Business Philosophy
“Fans First” is non-negotiable
Cole says the organization’s mission is simple: create fans, not just maximize short-term revenue. That means:
- keeping ticket prices accessible
- avoiding hidden fees
- prioritizing the experience over extracting every possible dollar
- keeping games free to watch on YouTube globally
He argues that if you drift away from fan-first values, you may win financially in the short term but lose trust over time.
Don’t market the product — make the product worth sharing
The Bananas spend very little on traditional marketing. Instead, they invest in:
- the live experience
- broadcast quality
- social-friendly moments
- original music and recurring bits
The idea is that remarkable experiences generate their own word-of-mouth and social amplification.
Create a repeatable experimentation engine
Cole says they use a deliberate creative process:
- idea sessions
- table reads
- rehearsals
- constant testing and iteration
The goal is to create a fresh show every week while learning quickly from what works and what doesn’t.
Growth, Pricing, and Expansion
Growth by proving demand
Rather than starting with big capital raises or sponsor dependency, the Bananas built traction by selling tickets directly. Cole says that if people will pay to attend, you know you’ve created real value.
Scaling without losing the magic
As the company expanded into multiple teams and stadium tours, Cole worried about diluting the brand. His solution was to make each team and each show distinct while preserving the same fan-first DNA.
Low prices, high value
Cole says the Bananas intentionally keep ticket prices below what the secondary market would support. They want fans to feel good about the price and the experience, even if that means leaving money on the table.
Leadership and Team Culture
Creative and operational roles must be distinct
Cole describes a division of labor similar to Walt and Roy Disney:
- Cole focuses on creative vision, show design, music, and new ideas
- Jared Orton, the company president, handles operations and execution
This allows the organization to dream big without losing operational discipline.
Joy is the fuel
A major theme of the episode is the emotional atmosphere inside the company. Cole says the staff, not just the players, get excited to be part of the show because the work itself feels meaningful and fun.
Advice for Founders and Young People
Do what gives you energy
Cole tells students and young professionals to identify the activities that make time fly. For him, those are:
- creating
- sharing
- growing
He believes people do their best work when they’re energized, not just motivated by obligation.
Be a challenger forever
One of Cole’s central ideas is that even when you’re winning, you should still think like the underdog. Staying slightly scared, slightly hungry, and constantly improving helps prevent complacency.
Notable Quotes
- “Fans first always.”
- “You should always be a challenger.”
- “It’s about the amazing moments that you get to create every day.”
- “Joy is contagious.”
- “Do what gives you energy.”
Main Lesson
Jesse Cole’s story is really about rethinking what a business is for. The Savannah Bananas didn’t succeed by acting like a traditional sports team; they succeeded by obsessing over delight, designing for emotion, and building a culture that treats every game like a live show. The big takeaway for leaders: if you make people feel something extraordinary, they will come back, bring others, and help spread the word for you.