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The Day the Jetski Won
Offshore Sep 12, 2026 · Gulf of Mexico · 4 min read

The Day the Jetski Won

The jetski after it flipped, 10 miles offshore in the Gulf

The picture is AI generated this time because I was more concerned with getting it flipped back over than I was trying to remember to turn on the camera lol

I lost three fishing poles, my wallet, and every piece of trolling gear I own to the Gulf of Mexico. On the bright side, I now have material.

Let me walk you through the decision tree, because in hindsight it's less a decision tree and more a series of doors I opened myself.

/ Bad Decision #1: Inviting a Friend

My buddy's jetski was in the shop. So I said the thing you say: "just ride with me."

This meant two grown men, one jetski, and a combined center of gravity that we would later describe to each other as "aspirational."

/ Bad Decision #2: Stopping at 10 Miles

We were headed offshore — 33 miles was the plan. At about 10 miles out, we decided to stop and troll for a bit. This is the part where, if you've been on the water, you already know what's coming.

Here's the sequence:

The jetski flipped. (Oops.)

Normally that's a minor thing. You flip it back, you laugh, you go home. But normally you don't have: a guy who has never been that far offshore, fishing gear everywhere, and an open front box full of everything I own.

We got it flipped back over. That part went fine.

The part that didn't: three poles, my wallet, and all the trolling gear are now permanent residents of the Gulf floor at 10 miles out. None of it was cheap. All of it was my fault.

/ Bad Decision #3: The One I'm Still Annoyed About

Here's the lesson that actually stings, because it wasn't the flip — that was physics. It was the tie-downs.

Nothing was secured. Not the box, not the gear, not the loose stuff. I've run this jetski offshore plenty of times and never once lost anything, so I'd quietly filed "tie everything down" under things that matter when things go wrong — and things go wrong about never, right up until they go wrong all at once.

The flip cost me nothing that mattered. The unsecured gear cost me three poles and a wallet.

Those are different failures. One is bad luck. The other is a plan that only worked because I hadn't tested it.

/ What I'd Do Differently

/ The Actual Upside

We're alive. We're fine. We're a little sore and we're laughing about it, which is the correct response and also the only one available.

And if you want the real takeaway: I've spent years talking about margin — about building systems that still work when conditions change. I went out on the water with zero margin, and the water collected.

The tank story is a metaphor. This one's just a bill.

/ Stay Tuned

I may have more pictures to add later today. We're going back with scuba gear in about 45 minutes.

Stay tuned.

Until the next run out — work hard, play hard.