I was standing at the bar of the Royal Bermuda Yacht Club when the offer came in. It was a classic “teak and steel” moment—one of those high-stakes pivots that remind me why I traded the air-conditioned boardrooms of Microsoft for the salt-sprayed unpredictability of the Atlantic.
The best systems aren’t just built on code—they’re forged in grit and tradition.
A navigator for a prominent crew had gone down with a fever, and they needed someone who could manage a complex system under pressure.
“Joe, we need your eyes on the charts,” the skipper said. I looked at the dark and stormy in my hand, then out at the reef-lined turquoise water. My background in building high-performing systems had taught me that whether you’re a fractional COO or a sailor, the fundamentals are the same: you mitigate risk, you optimize for speed, and you never underestimate the environment.
The race was a grueling sprint, a shorter but more intense version of the endurance tests I usually write about, like the Vendée Globe or the Sydney to Hobart. As we hit the open sea, the corporate logic faded, replaced by the primal pull of a hull slicing through waves.
We weren’t just racing other boats; we were managing the relentless pressure of the sea. By the time we crossed the finish line back in Hamilton, I realized that the best systems aren’t just built on code—they’re forged in grit and tradition.
Joe the Writer 
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