Entertain Always: Make Business Fun (Fans First Principle #2)

Turning Everyday Logistics into Memorable, Fan-Worthy Moments

Pop quiz: what business are you really in? If you said trucking or logistics, Jesse Cole might buzz the wrong answer. He’d say you’re in the entertainment business – because every business is, in the sense that you’re trying to give people a positive, enjoyable experience. Now, “entertainment” in our context doesn’t mean you need jugglers in the warehouse (although hey, if that delights your clients, go for it!). It means finding ways to make each interaction enjoyable and memorable instead of dull and transactional. Entertain Always is about adding spark and surprise so that customers actually look forward to engaging with you.

Jesse’s Savannah Bananas provide a masterclass in this. At their games, the entertainment isn’t an afterthought – it’s woven into every inning. We’re talking players doing choreographed dances, spontaneous conga lines in the stands, and fans literally singing and laughing through what would normally be “downtime” in a regular game. They’ve turned the ballpark into a stage. Even off the field, the Bananas keep it fun – their emails, videos, and social media are full of humor and behind-the-scenes antics. By the time a fan arrives at the stadium, they’re already smiling. Cole even considered the very edges of the experience: he put funny signs in bathrooms and had his staff do silly skits during rain delays. The philosophy is clear: no moment should be boring when you’re with the Bananas. If you’re standing in line, they’ll send somebody in a banana costume to dance with you. If you’re on hold on the phone, you’ll hear a joke or a song instead of elevator music. The Bananas want every touch to either raise an eyebrow or crack a grin.

Now, transporting that idea (pun intended) to the world of transportation businesses: how can you entertain always? One way is to look at the bookends of your customer experience – the very first impression and the final send-off. Those are prime opportunities to leave a positive emotional mark. For example, when you sign a new client, don’t just send the standard welcome email full of PDFs and terms. Spice it up! Maybe send a welcome package with your company’s swag and a handwritten note, or a quirky welcome video from the team. One logistics startup we know sends new customers a mini wooden toy truck with their logo on it, packaged inside a box that says “Let’s roll! Welcome to the family.” It’s a small thing, but it’s so much more fun than just a login and an invoice. Guess who proudly displays that toy truck on their desk? The new customer – and it inevitably sparks conversations about your company.

During the journey, find little moments of delight. Did a shipment go exceptionally well? Have your rep shoot a quick celebratory email with a funny GIF (maybe a dancing banana 🍌 GIF as a nod to Jesse, why not). Do you send out a newsletter or operational update? Throw a “trivia corner” at the bottom or a joke relevant to trucking life. If you have clients visiting your office or if you host webinars, incorporate an element of play – maybe a surprise guest, a giveaway, or even a quick game (prize for whoever can guess a funny stat, etc.). These touches may sound trivial, but they add up to an impression that “hey, these folks are different – they make work enjoyable.”

Importantly, entertainment must be intentional. Jesse Cole doesn’t wing it – he scripts out how to handle even negative situations in an entertaining way. So, plan for your tough moments too. For example, if a delivery is running late (stressful moment, right?), what can you do to ease the tension? Perhaps proactively send the customer something uplifting – a coupon for their next shipment, or if it’s a local delivery, maybe a surprise snack delivered to their office with a note: “Truck stuck in traffic? Don’t worry, have a coffee on us while you wait.” It sounds a bit extra, but that’s the point. You turn frustration into appreciation, maybe even a chuckle, because who expects a delay to come with free coffee?

Let’s bullet down a few actionable ideas to “Entertain Always” in your business:

• Craft a Signature Welcome: Make your first interaction special. Could be a creative welcome kit, a personalized welcome video, or a humorous onboarding manual (imagine “The Hitchhiker’s Guide to Shipping with [Your Company]” – fun and informative).

• Use Humor and Surprises in Communication: A little personality goes a long way. Include a fun fact or a light joke in your routine emails. Celebrate Transport Tuesdays on social media with a goofy post or driver highlight. On a customer’s shipment anniversary (one year of doing business, etc.), send them a funny e-card or even a cake.

• Delight in Unexpected Places: Think of the most “boring” touchpoint you have and jazz it up. Invoice time? Put a friendly note or interesting industry cartoon at the bottom of invoices. Phone hold? Use a custom message that makes them smile (“Your call is important… meanwhile, did you know the world’s longest truck was 304 feet? We’ll be right with you!”). Even your email signatures could include a quirky tagline or fun quote.

• Empower Your Team to Have Fun Too: Encourage your employees to show their personality (within professional bounds). A customer service rep with a warm, jokey demeanor can turn a mundane call into a memorable one. Maybe host an internal contest for the team to come up with the most creative way to thank a customer this month – winner gets a gift card. This not only yields great ideas, it also keeps your team entertained and engaged.

• Turn Mistakes into Moments: When something goes wrong, think like an entertainer. How can you flip the script? If a software bug causes a client inconvenience, maybe the team records a lighthearted apology video dressed as firefighters “putting out the tech flames.” If a truck misses a pickup, maybe send a “Rescue Squad” image with superheroes (your team) coming to save the day. Of course, you address the issue seriously, but a dash of humanity and humor can defuse a tense situation and show that you’re not a faceless corporation – you’re people who care.

At the end of the day, people remember experiences, not transactions. By infusing a sense of fun and surprise into your business, you differentiate yourself from competitors who might be larger or cheaper but are utterly forgettable. As Jesse Cole proved, even something as traditional as baseball – or trucking – can be transformed with entertainment. Fans leave Bananas games saying “I’ve never had so much fun at a ballgame”. What if your clients said, “I actually enjoy working on logistics with these guys”? That’s a competitive edge no rate cut can buy. So, get creative and don’t be afraid to entertain.

The noblest art is to make others happy – and happy customers will stick with you through thick and thin, because you make their day a little brighter.