From Mistake to Mission: How a Juggler Accidentally Became a Team Building Guru

Do money breakthroughs come from learning how to budget better, charge more, or hustle harder?

If it were just about spreadsheets and strategy, we’d all be rolling in it by now.

The truth is, your relationship with money has very little to do with your bank account—and everything to do with the story you’ve been told (and keep telling yourself) about what’s possible.

The Rewrite Your Money Story program is for people who are done repeating old patterns. It's where visionaries, misfits, and heart-led entrepreneurs come to drop the guilt, rewrite the rules, and finally build something that feels free, aligned, and unshakably theirs. Not someday. Now.

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And speaking of rewriting stories…

Today’s feature is about a man whose whole life changed because of a simple mistake—and how he turned distraction into a superpower, stagecraft into strategy, and outdoor adventures into insight for high-performing teams.

Let me introduce you to Greg Bennick.

At 12 years old, Greg Bennick just wanted to collect coins. Nerdy, wholesome, focused. He was ready to nerd out after school, cataloging Liberty Head nickels or whatever 12-year-old coin collectors do.

But fate—or, more precisely, a tired school secretary—had other plans. She signed him up for juggling.

He was furious.

Until he saw a kid in class juggling three baseballs like some kind of magician. It wasn’t just the trick—it was the focus. And Greg, a kid with undiagnosed ADHD, saw something that lit up his whole brain.

“I want that,” he thought.

He’s been chasing it ever since.

The Accidental Performer

By 13, he was juggling at professional gigs. By 15, he was doing corporate events and making executives laugh—like, really laugh.

Case in point: He once made a legendary businessman—the kind of guy with an army of handlers—crack up at his own famous catchphrase. The kid had guts. More importantly, he had timing.

That mix of performance, presence, and precision led Greg to discover something big: People don’t remember a PowerPoint. They remember a feeling. A moment. A metaphor that sticks.

Which is why Greg never just talks at people. He gets in it with them—juggling, joking, reflecting, and yes, occasionally jumping out of airplanes.

But more on that in a sec.

Why Focus Matters More Than Ever

Here’s the kicker: Greg isn’t just some former stage guy trying to stay relevant in corporate America. He’s not teaching parlor tricks.

He’s teaching focus—because it’s the one thing he’s had to fight for his entire life.

“There are 101,000 things every second that could pull us away from what matters,” he says. And no, that’s not an exaggeration. It’s science. (And if you’ve ever opened Instagram just to check one message and resurfaced an hour later with three new tabs open, you already know.)

But focus isn’t about staring harder at your to-do list.

It’s about presence. It's about what Greg saw in that 12-year-old juggler years ago—someone fully here. Not scattered. Not rushing. Just… present.

And when you bring that energy to a team? That’s when things click.

Juggling As a Team Sport (Really)

Yes, Greg teaches people to juggle. No, it's not about balls in the air. (Okay, it is. But not really.)

Juggling, he says, is a fast track to building self-trust, motivation, and team dynamics. It’s physical proof that we can learn new things—even when our brains are screaming otherwise.

It’s a metaphor you can feel in your hands. (Or drop. And pick up again.)

Plus, it breaks the ice fast. And let's be honest—your team probably needs that.

Leadership Isn’t a One-Way Mic

Greg’s not here to drop some TED Talk, take a bow, and peace out. He sticks around. Not because he has to—but because he cares.

He checks in. Follows up. Helps teams implement the ideas so it’s not just a one-time “rah-rah” moment. Because leadership isn’t shouting louder. It’s listening. It's creating a space where people feel their work matters. That they matter.

“When we reverberate together as a team,” Greg says, “we create a transformational dynamic that inspires people.”

Yes. He said reverberate. And somehow made it sound cool.

The Skydive Moment

Greg’s all about those moments where your stomach drops and your brain screams, “Are we really doing this?”

For him, that’s hanging out the door of an airplane at 12,500 feet before a skydive.

For you? It might be launching your first product. Hiring someone new. Saying no to that “sure thing” that doesn't feel right.

Whatever it is, he says the lesson’s the same: Trust your team. Trust the process. Let go.

Oh—and enjoy the free fall.

Offstage and Underwater

You want to know when Greg gets his best ideas? Swimming. Scuba diving. Hiking a remote mountain in Scotland.

Because stepping away from the screen does something no productivity app can.

His advice: encourage your team to do the same. Walk, swim, breathe. You’ll be amazed what comes up when you stop trying so hard.

Sometimes your best ideas arrive soaking wet or out of breath.

A Book, a Video, and a Guy Who Actually Gets It

Greg's not selling snake oil. He’s not going to tell your team to manifest their way to synergy.

He will help them connect, focus, and actually enjoy working together again.

If you want a taste of how he works, go watch his brand-new promo video. It’s packed with real talk, no fluff—and it’s actually fun to watch. Which, let’s be real, is a rare trait in corporate anything.

👉 Watch it now and connect with Greg at gregbennick.com

Seriously. Go see what juggling, scuba diving, and leadership have in common. It’s more than you think.

Hey friends,

I’m opening up 2 spots this month for a fast-turnaround content strategy sprint—designed to help you say what you do clearly, reach the right people, and stop feeling stuck or scattered with your marketing.

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Only 2 available this month.

If you’re interested, just reply and we’ll chat to see if it’s a fit.

If it’s not for you right now, I totally get it—but feel free to share this with someone who’s got a great offer and could use a little help making it land.

Thanks for being here. 🧡

– Sue