What Ryan Trahan Reminded Me About Wealth, Wonder, and the Power of Shared Adventure

Over the past few weeks, I’ve found myself pulled into an unexpected adventure—not my own, but one unfolding daily on YouTube.

It started with driving through Wisconsin and hearing my two youngest kids talk all about the adventure they were watching with Ryan Trahan. They wanted to ensure that they could see the latest post when he released his video at 11:00 a.m. ET.

They explained, Ryan Trahan, the creator my youngest son introduced me to, is currently on a mission to visit all 50 states in 50 days with his wife, Haley. But this isn’t just a travel vlog. It’s a surprisingly entertaining, deeply human fundraising campaign for St. Jude that—at the time of this writing—has raised over $5 million.

We don’t watch a ton of YouTube as a family, but lately, we’ve made time to follow Ryan’s journey together. Each new stop, each quirky challenge in a new state, each act of generosity—it’s become a fun shared moment between me and my kids. And, honestly, it’s sparked something more.

I’ve even encouraged members of my team at Milemarker with kids around the same age to tune in, so we can all share in these little adventures together. It’s become a wholesome touchpoint—something we all look forward to, something that reminds us how simple and powerful storytelling can be.

Watching Ryan traverse the country, you see his life unfold—not just the road trips, but his values, his joy, his business (like his candy brand Joyride, which my kids now insist we track down when we do occasionally walk to 7-Eleven).

It’s brilliant. But more than that—it’s real. And that’s the lesson.

What Ryan Trahan reminded me:

It’s not enough to run a good business. You’ve got to live a good story.

As someone who spends their life thinking about how to help wealth management firms communicate better, I can’t help but notice how different this is from what we typically see.

Most RIAs show up like a suit in a brochure. Polished, sure—but forgettable. The personality is gone. The mission is generic. The brand has no pulse.

But what if we let our businesses be more human? What if we created something people actually want to follow? Something our clients’ kids might want to watch?

Because at the end of the day, wealth isn’t the goal. It’s a tool. And tools are meant to build something bigger than ourselves.

Ryan’s adventure is a masterclass in how to make your platform matter. He’s turning joy into generosity, business into meaning, and entertainment into action.

That’s something every founder, advisor, and leader can learn from.

So here’s the invitation:

Let your business tell a story worth watching. Infuse it with adventure, heart, and purpose. Speak to something bigger than money. Because when you do, people don’t just listen—they join in.

That’s how movements start.

That’s how impact scales.