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 · 10 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 ReturnEarly call. Coffee, bloody marys, and breakfast bites as we clear the breakwater at Marina del Rey and set course for Two Harbors — the remote, rugged west end of Catalina Island. 30 miles of open Pacific ahead. This is the run that separates the club from every other group you've been in.
MDR Departure · Open OceanDrop the hook at Two Harbors — one of the most spectacular natural anchorages on the California coast. Clear blue water, kelp beds, Garibaldi fish under the hull. The chef begins preparing lunch on deck as you swim off the back or settle into the rhythm of the harbor.
Mooring · Isthmus CoveFull lunch on deck at anchor, Two Harbors as the backdrop. Once everyone has a plate, one quick round — 10 minutes each. Whatever's on your mind — your business, your relationships, what's testing you. Then eat, swim, and talk. The water is 80 feet of visibility and the harbor is yours.
The Round · 10 Min Each · Swim TimeThe shoreboat runs you into the dock. Two Harbors is one of a kind — a tiny village with no cars, world-class snorkeling, and an atmosphere that exists nowhere else in Southern California. Group activities spread out from here.
Shore Excursion BeginsThe afternoon at Two Harbors is unstructured on purpose. Options include:
Shoreboat back to the Sunset Trio. Cast off from the mooring and set course northeast back to Marina del Rey. The sun is dropping toward the mainland horizon. Cold drinks, tired legs, good stories. The run home is the best part of the trip.
Return Passage · Open OceanBack at the Marina del Rey slip at golden hour. The bar stays open until docking. These are the sessions members talk about for months. Long days, full conversations, real adventure — and you did it with 14 other members in your chapter who all showed up.
MDR Return · Sunset Dock8AM departure from Marina del Rey. Breakfast spread, morning drinks, and the open Pacific ahead. The crossing to Avalon takes 2–3 hours depending on conditions. Good conversation territory — the ocean does something to people.
MDR Departure · Open OceanArrive at Avalon — Catalina's main town and one of the most charming harbors in California. The iconic Casino building anchors the hillside. Crystal water in every direction. Moor up and take it in. The chef starts on lunch while you get your bearings.
Mooring · Avalon HarborFull lunch on deck at anchor in Avalon Bay. Once everyone has a plate, one quick round — 10 minutes each, one thing you're building, one thing you need. Then eat, swim off the back, and enjoy the best view in Southern California.
The Round · 10 Min Each · Swim TimeThe shoreboat drops you at Green Pier. Avalon is walkable, charming, and purpose-built for exactly this kind of day. The main strip along Crescent Avenue has everything you need and nothing you don't.
Shore Excursion BeginsAvalon has more options than Two Harbors but the same island pace. Group activities include:
Shoreboat back to the Sunset Trio. Cast off from the Avalon mooring and set course for Marina del Rey. The sun drops behind the island as you head northeast. Stories from the day, cold drinks, open ocean. The best conversations of the trip happen on the run home.
Return Passage · Open OceanSunset arrival back at Marina del Rey. The bar stays open until docking. Nobody wants to leave the boat. These are the sessions that define the club — the ones that make the $1,495/month feel like the best investment you've ever made.
MDR Return · Sunset Dock
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.