Meet Cpt. CLRogerson

Hi, I’m Captain C.L.Rogerson. After decades leading in the healthcare industry, I made the biggest course correction of my life: I stepped away from the boardroom, climbed aboard my boat, and started designing a lifestyle on my terms, one anchored in freedom, travel, and meaningful connection.

Now I help others do the same.

The Journey So Far

The good life isn’t later. It’s now.

I’ve been planning to retire at 50 for most of my life. Call it a family tradition, my father did it, so did his father. But while they followed a well-worn path, I always knew I’d take the scenic route.

I built businesses. Raised a family. Lived the “successful” life. Then, at 29, a brain aneurysm tapped me on the shoulder and whispered something I’ve never forgotten: this doesn’t last forever.

So I made a promise to myself, no more deferring the good stuff.

I got licensed as a captain. Started chasing sunsets instead of schedules. Traded boardrooms for boat decks. And somewhere along the way, I stopped just planning for the next chapter… and started living it.

These days, I travel wide and often. I’ve taken friends and family around the world, or at least a damn good slice of it. I live with my hand on the helm and my calendar wide open. And I help others do the same: people ready to trade obligation for adventure, burnout for beauty, and bucket lists for actual experiences.

Whether it’s a cinematic cruise through the Med, a barefoot charter in the Grenadines, or a trip that finally makes you feel at peace, I’m here to help chart the course.

And if you need a little push? I raised my kids on this:

“One day or day one, you decide”

Life doesn’t wait. Let’s get you living it.

What I Believe

I believe travel isn’t an escape, it’s a catalyst, the best way to gain perspective on our world and ourselves.
I believe it’s never too late to rewrite your story, add another chapter or perhaps write a sequel!
And I believe the best stories happen when you stop waiting for someday and say yes to today.

The Captain’s Approach

I’m not here to sell you a week away from the grind. I’m here to help you trade the clock for a compass.

This isn’t about checking boxes or chasing sunsets on someone else’s schedule. It’s about stepping aboard a yacht and remembering what it feels like to live by the wind, the tide, and your own direction.

Whether you come to the Founders Club to experience life underway, bring me aboard as captain for your own voyage, or invite me to share stories from the helm with your audience, my mission is the same:
to help you reclaim a life that feels authentically yours.

Because the good life isn’t found in a brochure.
It’s found on the water, one horizon at a time.

Quick Facts

  1. 🧭 30+ years of sailing and global travel experience

  2. ⚓ USCG-licensed captain with real sea miles

  3. 💬 Known for straight talk, good stories, and solid coffee

  4. 🎯 Goal: Introduce thousands of people to travel-centered lives

The good life doesn’t schedule itself. Let’s chart your next move.