Experiment Constantly: Embrace Crazy Ideas & Fail Forward (Fans First Principle #3)

Why Trying Crazy Ideas Might Be the Best Route to Growth

If you walk into the Savannah Bananas’ office, you might see a big wall full of sticky notes with wild ideas – things that sound impossible or ridiculous. That’s because Jesse Cole built his success on a culture of constant experimentation. Experiment Constantly is the third Fans First principle, and it’s all about ideation, innovation, and iteration on steroids. The Bananas try everything. Some of those experiments flop spectacularly (there was a time they tried having players deliver roses to fans during the game – sweet gesture, but it kind of disrupted the play!). But many experiments turn into pure gold that fans love. Cole likes to say, “We’re always just one idea away from a sellout.” In fact, it was a crazy idea – naming the team the “Bananas” and leaning fully into the silliness – that first put them on the map amidst skepticism and laughter. If he hadn’t been willing to try the outrageous, the Bananas would still be just another struggling team.

Jesse’s personal practice is to write down 10 new ideas every day. Think about that: most of us struggle to come up with one fresh idea in a week, and he’s churning out dozens a week! The reality, as he admits, is most of those ideas stink. Out of 3,650 ideas a year, maybe a few dozen are usable, and maybe a handful are hits. But without the hundreds of “bad” ideas, you’d never get the brilliant ones. One of his famous quotes on this: “One idea can change the game for you. If you’re not getting criticized, you’re playing it too safe.” The Bananas got plenty of criticism for their whacky experiments (hey, purist baseball fans were not amused by the tutu-wearing batter or the conga line on the field). But as Jesse says, criticism means you’re doing something different enough to notice. The worst thing is not failure – it’s being ignored into irrelevance. By pushing boundaries, you either win or you learn. Every experiment yields either a victory or a story to tell, and the stories often pave the way to the next win.

So how can you foster a culture of experimentation in an industry as practical and risk-averse as transportation? It starts with mindset. Give yourself and your team permission to try stuff that might not work. For example, maybe you’ve always followed a standard sales approach to land clients. What if you tried the opposite? (Fans First is about the opposite, after all.) What if instead of cold calling with a sales pitch, you started sending prospects a free resource or hosting a no-sales “logistics coaching hour” each week? It might flop – or it might differentiate you as a helpful thought leader. The point is to test it and see.

Here are some concrete ways to Experiment Constantly in your business:

• Brainstorm Like It’s Your Job (Because It Is): Set aside regular time for idea generation. This could be a weekly creative meeting with your team, or a personal daily habit like Jesse’s. And here’s the key – no idea is too crazy to suggest. Encourage off-the-wall thinking. Want to decorate a truck like a giant banana and drive it to a trade show? Throw it out there! Crazy can lead to genius.

• Small Experiments, Fast Feedback: You don’t have to bet the farm on a wild idea. Do small-scale pilot tests. Say you have an idea to offer guaranteed 1-hour pickup for local clients. Instead of rolling it out company-wide, test it with one client or on one route for a month. Gather feedback, see what breaks, what works, adjust, then expand. This way, failures are low stakes and successes can be scaled.

• Use Social Media as a Lab: Cole used TikTok and others as a testing ground. You can do the same. Try posting different types of content – one day a how-to tip, another day a funny behind-the-scenes of your dispatcher dancing (if Jesse’s players can dance, why not your team?). See what resonates. Social media is great because if an experiment flops, it’s gone in a flash; if it hits, you just gained goodwill or even leads.

• Learn from Every Attempt: This is crucial. When an experiment fails – and many will – treat it like R&D data, not a mistake. Gather the team and ask: Why did it flop? What did we learn? Sometimes a failed idea can be tweaked into a successful one. (Maybe customers didn’t love your first “24/7 support by AI bot” idea – but through that, you learned they would love extended hours with a human rep. Boom, new idea.) Create a culture where failure stories are celebrated and shared. Cole celebrates his team’s wild ideas even if they fail, because it means they were pushing limits.

• Keep an “Idea Backlog”: Not every crazy idea can be tried immediately, but don’t let them slip away. Maintain a backlog list of “Fans First Ideas” for your business. This can be an internal Google Doc or a board in your project management tool. It shows your team that ideas matter and will be revisited. Plus, an idea that’s ahead of its time might become feasible later as your company grows or tech changes.

One more thing: share the spirit of experimentation with your customers if possible. People love to be part of something novel. For instance, you could invite a few loyal clients to be beta testers of a new service or a new tracking app you’re developing. Frame it as “We’re always trying to improve – and we value your input.” Clients will appreciate the inclusion, and you get real-world feedback.

Real-World Anecdote: A medium-sized trucking company in the Midwest decided to experiment with a guaranteed on-time delivery or it’s free – a bold promise in an industry rife with unpredictable factors. Everyone thought they were nuts. Sure enough, the first iteration of this guarantee cost them a bit of money in refunds during a winter storm season. But they didn’t kill the idea; they refined it (added some sensible weather exceptions and improved their route planning). The guarantee became a huge marketing differentiator. Within a year, they gained so many new contracts from shippers who were sick of late deliveries that it more than paid for the early refunds. That success wouldn’t have come if they hadn’t dared to try something radical, take a few lumps, and tweak it.

The bottom line: innovation is a numbers game – the more shots on goal, the more chances to score. In a conservative field like transportation, if you’re the one willing to experiment, you immediately stand out. Sure, your competition might laugh when you try something unconventional. But as the Bananas have shown, he who laughs last, laughs best – likely in an all-yellow tux on the way to the bank. So go ahead, try that crazy idea. The worst that happens is you get a good story; the best is you revolutionize your business.