On Leading with Imagination ✨
What do the likes of Walt Disney, the Savannah Bananas’ Jesse Cole, and Martin Luther have in common?
They each lead with imagination.
Also…
✨ They each have created movements.
✨ They cared deeply about the people who followed their causes.
✨ They were masters of experience.
The past week for me has been full of imagination.
I went from:
💥 Hosting our first-ever Sustainable Giving Workshop, to
🍌 Attending the sold-out Savannah Bananas game in Seattle, to
🏰 Leading a day at Disney World with a group of 20 charity leaders.
The theme of our time at Disney was “Prototyping Tomorrow: Connecting and creating the world of tomorrow through innovation and imagination.”
Above: 20 leaders investing in connection, inspiration, and learning – dreaming about creating the world of tomorrow through innovation and imagination.
My soul is bursting with what the power of imagination can make possible in the hearts and minds of leaders and the organizations they lead.
I’m guessing that you’ve heard of Walt Disney and Martin Luther… but have you heard of the Savannah Bananas, or Jesse Cole, their founder and owner?
Above: Savannah Bananas’ founder and owner Jesse Cole personally greeting fans as he does for every Bananas game.
Jesse Cole had a dream – what if his beloved game of baseball was accessible, entertaining, and fun? What if he could engage a generation of disinterested or apathetic to the game, and give them a remarkable experience? And what if it was built not to last a year, but for decades to come?
Founded in 2016 as a minor league baseball team, in 2021, Jesse took the team on the road for their first "world" tour called the One City World Tour. When all was said and done, that first tour played in front of 100,000 fans – not bad for a minor league baseball team!
But Jesse and the Bananas were just getting started. The following year, they went on the road again, playing in front of 500k fans.
Last year, 2024, they played in front of over 1 million fans.
But this year? In 2025, as of the time of this writing, they’ve played in front of 2.2 million fans. 🤯
The Bananas were just the start. Now they have three other teams that tour, and trade off playing each other – the Party Animals, the Firefighters, and the Texas Tailgators.
While we’re on the subject of mindblowing stats about the Bananas:
🍌 10.5 million on TikTok alone, more followers than the MLB.
🍌 3.6 million fans on their waitlist.
🍌 94,000 fans in Seattle, Washington this weekend, SELLING OUT the Seattle Mariners’ T-Mobile Park… TWICE.
Including the Raley family.
Above: At the sold-out Savannah Bananas game against the Firefighters in T-Mobile Park, cheering along with 47,000 other fans.
My girls’ school scored tickets to see the Savannah Bananas in one of two first-ever games in Seattle.
Playing two nights to a sold-out crowd of more than 47,000 fans each night, the Bananas play a variation on baseball known as “Banana Ball.” But it’s so much more than that. Imagine the Harlem Globetrotters, Cirque du Soleil, and Disney all combined into one experience.
Innings were played. Runs were scored. But it was anything but a normal night at the ballpark.
On the Savannah Bananas and Being REMARKable
One of the first marketing books I ever read was Seth Godin’s Purple Cow: Transform Your Business by Being Remarkable. In the book, he offers a powerful insight: to be remarkable as a brand means to be worthy of REMARKing on.
“Something remarkable is worth talking about. Worth noticing. Exceptional. New. Interesting. It's a Purple Cow. Boring stuff is invisible. It's a brown cow.” – Seth Godin, Purple Cow
Seth goes on to make a statement that has stood the test of time and is more relevant today than it was 20 years ago when he wrote it.
"The old rule was this: Create safe, ordinary products and combine them with great marketing. The new rule is: Create remarkable products that the right people seek out." – Seth Godin, Purple Cow
Banana Ball is REMARKable.
Jesse Cole is REMARKable… and not least of which because he owns NINE yellow tuxedos! 💛
Today, in honor of Walt Disney, Martin Luther, and Jesse Cole, I would like to share several observations on what it means to lead with imagination.
Three Lessons on Leading with Imagination
Three things stand out when I look at the examples of Walt Disney, the Savannah Bananas’ Jesse Cole, and Martin Luther:
1. Don’t be afraid to be misunderstood.
Leaders who lead with imagination aren’t afraid to be misunderstood.
Sometimes it takes a visionary leader to see something that few others see. There is a reason that when I launched Imago Consulting more than three years ago, I called it “IMAGO” Consulting.
Imago is a Latin word, and is the root of the word IMAGE, or IMAGination. But if you study the word in its original Latin, IMAGO is a word picture of a future that will be, but does not yet exist.
Walt Disney had the imagination to see that cartoons could be more than short, silly “appetizers” before a feature-length film, and on February 4, 1938, Snow White was a REMARKable feat that changed the world forever.
Later, Disney had a preposterous idea…
“As I'd sit there while they rode the merry-go-round, did all these things, sit on a bench, you know, eating peanuts, I felt that there should be something built, some kind of an amusement enterprise built where the parents and the children could have fun together.” – Walt Disney on a Little Amusement Park
The pushback to this “Disneylandia” concept was immediate and constant. Who in their right mind would be willing to drive 30 or 40 miles out to the orange groves of Los Angeles? His own team didn’t really believe him – “I didn’t bother to tell him that I thought he was out of his mind” (Disneyland Handcrafted Official Trailer).
Turns out that Disneyland was a pretty good investment. BUT, and this is key, if it were up to conventional wisdom and leadership, we would neither have animated feature films that move the heart, or the very theme parks that bring so much joy into the world.
But Walt Disney wasn’t a conventional leader. Walt led with imagination.
💡 Takeaway: Leading with imagination means that sometimes you will be misunderstood. While this isn’t a guarantee you are on the right track, successfully innovating often requires the willingness to sit in the discomfort of others’ misunderstanding.
2. Leverage the mediums of the day.
Martin Luther’s imagination changed the world as Western Europe knew it in the 1500s. Luther was driven by a passion to challenge the conventions of his day – particularly the practices of the Church that he grew to believe were counter to its very first founding principles.
Luther led with imagination as well. He was one of the first leaders to recognize the potential of the printing press, not just to mass-produce entertainment, but to shape the thinking of his day. Before Luther, the Bible was typically read in Latin or published in the original languages of Hebrew and Greek. The clergy had access because they were educated in those languages and could afford expensive volumes.
Common people didn’t speak the academic language of Latin, and they certainly didn’t have access to books of any kind.
But Luther was convinced that the people should be able to read the Bible for themselves. And so he set to work translating the Bible into the language of his people, common German. That was revolutionary.
It turns out that when you give people direct, unfiltered access to information to read and interpret for themselves, amazing things can happen! (In some ways, a modern example is the Arab Spring uprisings of the 2010s. Social media platforms gave whole people groups access to information that had previously been filtered or unavailable.)
Luther recognized the potential of the printing press to disseminate ideas to the general public, and that insight has changed the world we live in today.
Disney entered the television market in the 1950s, a medium that every other major movie studio viewed as a threat and as irrelevant (who would want to have a television in their home when they could go to the movies?). Instead, Disney saw it as complementary to movies and as a means to tap into a huge and growing audience.
Starting in 1954, one year before the opening of Disneyland, “Walt Disney’s Disneyland” began airing and captured an entire generation’s imagination. (Including, by the way, my mother, who has told me stories of how the experience enraptured kids and families).
Jesse Cole is still in the midst of his story, but he clearly leads from imagination. In addition to inventing a new form of baseball focused on removing the friction from the game, he’s also invented new ways of thinking about entertainment, and Cole’s use of social media fuels Banana Ball’s explosive growth.
📃 Luther leveraged the printing press.
📺 Disney leveraged television.
📱 Cole is leveraging social media.
💡 Takeaway: Leading with imagination and creating an outsized impact requires leveraging the mediums and natural resources around you. Imagining new ways to harness the power of today’s mediums is central to the task of scaling innovation.
3. Learn from outside your sector.
Jesse Cole is reimagining a new form of entertainment with Banana Ball. To build this remarkable experience that is taking stadiums by storm, Jesse didn’t look to his own industry of baseball.
Instead, Jesse shares where he draws inspiration from in a video interview with the Wall Street Journal:
“The greatest leaders and the greatest organizations learn from outside their industry. I haven’t learned from the baseball industry. I learned from Saturday Night Live, I’ve learned from the Grateful Dead, I’ve learned from Cirque du Soleil, I’ve learned from WWE, I’ve learned from Taylor Swift, I’ve learned from Mr. Beast, Jeff Bezos and Amazon, from Apple.” - Jesse Cole
To lead with imagination, it’s helpful to look outside the confines of your own sector or industry. It helps to cultivate what I call an Outside Mindset.
An Outside Mindset enables us to deliberately counter the temptation of narrow expertise by cultivating a broader perspective.
What does an Outside Mindset look like? From observing leaders, I’ve noticed a number of behaviors and ways of thinking that they share in common.
An Outside Mindset…
⚡ Leads with curiosity.
⚡ Is open to new ideas.
⚡ Pays attention to the outside world.
⚡ Cultivates diverse relationships.
⚡ Seeks outside perspectives.
⚡ Attends events outside one’s sector.
For nonprofit leaders, I suggest attending an event or conference outside of your typical space. You can always go to your industry association conference to connect with peers, but you are much more likely to learn new things when you stretch yourself and get outside of your space.
💡 Takeaway: If one is to lead with imagination, then it’s important to be exposed to things that spark the imagination. That’s why it’s so important to learn from outside your sector.
That’s what our Imago Day was this week for 20 senior charity leaders – a way to get outside of our typical surroundings, to connect, and imagine what the world of tomorrow might look like through innovation and imagination.
I’d say it was a pretty good week. ✨
Until next week… Surf’s Up! 🌊
- Dave
About the Author | Dave Raley
Consultant, speaker, and author Dave Raley is the founder of Imago Consulting, a firm that helps nonprofits and businesses who serve nonprofits create profitable growth through sustainable innovation. He’s the author of the book The Rise of Sustainable Giving: How the Subscription Economy is Transforming Recurring Giving, and What Nonprofits Can Do to Benefit. Dave also writes a weekly innovation and leadership column called The Wave Report, and the co-founder of the Purpose & Profit Podcast — a show about the ideas at the intersection of nonprofit causes and for-profit brands. Connect with Dave on LinkedIn.
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