From the Helm to the Closing Table

From the Helm to the Closing Table

How did I not see it before? Being a boat captain is a lot like being a Realtor.

Back in my charter days in St. Croix, the day didn’t start when the guests showed up smiling on the dock. It started the night before, me in the dark throwing a cast net for bait, salt air mixed with diesel drifting from the other boats tied up around me. By 4 a.m., the coffee was down, coolers iced, gear laid out, and the boat already humming as I eased out of the slip.

One morning, I had a father and his son onboard. The kid couldn’t have been more than ten, clutching that rod like it was the only thing tethering him to earth. We hooked a tarpon, and when it launched — silver flashing in the first light, the kid’s whole face lit up. I talked him through every run, every pull, while his dad stood there grinning like he was watching something holy.

Another trip, it was a reef shark. Nothing movie-sized, but enough to give a fight that mattered. When I got it alongside, I steadied it so a little girl could lay her hand on it. She was trembling, but her smile said everything. Her parents clicked the photo, and I knew before the shutter even snapped that picture would end up framed back home.

What most people never saw was what it took to make those moments happen. I wasn’t just a captain. I was mechanic, weatherman, safety officer, and quartermaster ordering gear months ahead because shipping to the islands was slow and unforgiving. I carried backups for everything. tools, parts, even lures, because out there, unprepared isn’t an option.

And that’s the overlap I missed at first. Running a boat and running a real estate deal are the same animal. You prep before the client shows up. You read the conditions. back then, moon phases and tides; now, market shifts and interest rates. You anticipate problems, pivot when plans break, keep people safe when storms roll in. And you make damn sure that at the end, they leave with more than they came for, a story, a smile, something they’ll never forget.

When I was a captain, I wanted guests to walk away with fish in the cooler and a memory they’d talk about for years. Now, I want my clients leaving the closing table with keys in hand, a grin on their face, and the same feeling: this was worth it.