A Private Brotherhood · Two Chapters · 15 Seats Each
The conversation you've been trying to find — at sea.
Marina del Rey & San Diego.
You've built something. You've sacrificed for it. And somewhere along the way you realized that success at the highest level is lonelier than anyone tells you.
This is the answer to that.
Not a networking event. Not a mastermind. A brotherhood — fifteen high-performing men, once a month, on the water. Adventure that sharpens the mind. Food worth showing up for. Conversation that actually goes somewhere.
We sail. We eat well. We talk business — the hard calls, the pivots, the things you can't say in a board meeting. We talk relationships — the marriage that's carrying more weight than it should, the divorce you're navigating, what it actually costs to be the provider and the protector at the same time. We help each other carry it.
And when the right opportunity surfaces, you'll know fifteen men who can move on it with you.
This works for the man who built a company past $1M or a portfolio past $1M — and who finds himself navigating success and real life at the same time. The business decisions nobody can help you with. The marriage or divorce happening in the background. The weight of being the one everyone else leans on. Married, divorced, single — doesn't matter. What matters is you've been somewhere, you've carried something, and you're tired of doing it without a room full of men who actually get it.
If that's not you yet, that's fine. Come back when it is.
I built Island Boat — the charter company behind the Sunset Trio in Marina del Rey and the Sunset Duo in San Diego — over the last several years along side my 15 year marriage. By most measures, it was working.
During that same stretch, my marriage fell apart.
I won't get into all of it. But I went through the hardest year of my life while running what looked, from the outside, like a thriving life, love and marriage.
That's where this came from.
Not from a business plan. From realizing that the men I most respected — entrepreneurs, business operators, investors, guys who'd actually built things — were mostly carrying it alone too. Good at the surface level. Something heavier underneath.
I wanted a room where that wasn't the case.
I'm on every session. I review every application personally. This isn't a managed program — it's something I built because I needed it too.
If something in this landed for you, that's exactly why I put it here.
— Ryan Kirk
From the marina to the horizon and back. Choose your chapter and your route — every month is a different adventure.
Marina del Rey departs on the Sunset Trio — our 63ft private yacht. Choose your destination:
Pull up to the slip at Marina del Rey. Coffee, morning bites, and the easy energy of men who know they're exactly where they want to be. The captain briefs the route as lines are cast off. No agenda yet. Just arrive.
MDR Harbor DepartureThe marina shrinks behind you. The first 90 minutes are completely open. Find the conversation that matters, get a drink, watch the coastline open up. This is where the first real connections form — no forced introductions, no name tags.
LA Coastline CruiseThe chef serves a full lunch on deck as we cruise toward Malibu. Once everyone has a plate, one casual round — 10 minutes each. Whatever's on your mind — your business, your relationships, what's testing you. Then eat, talk, and let the Pacific do the rest.
The Round · 5 Min EachThe afternoon is yours. The Malibu coastline scrolls by, the bar stays open, and the conversations go wherever they need to go. Deals get discussed. Introductions get made. Friendships form. No clock watching. No agenda.
Malibu / Coastline RouteGolden hour return into Marina del Rey. The bar stays open until docking. Nobody rushes off. You leave with a few people you genuinely want to talk to again. That's a good day.
MDR Return
Get the full details — who we are, what a day looks like, and what membership costs.
Applications are reviewed personally within 48 hours. No payment until approved.
No payment required until approved. Approved applicants will receive a personal call from Ryan before their seat is confirmed.
Questions? hello@theislandclub.co
Ryan reviews every application personally within 48 hours.
If it's a fit, he'll reach out directly — a real conversation, not a form letter.
No payment collected until you're approved and ready to board.
This is the brotherhood. If your seat opens, we'll see you on the water.
The Island Club · See you on the water.