A Tuesday morning. Coffee. Email from a client we’ll call Yogi — to protect his identity, but mostly because it amuses me, and if you know Wyoming’s geography you’ll understand why.

Yogi wanted Jackson Hole. Skiing, hard-packed snow, serious runs. None of those resorts where tourists take selfies on the chairlift and then cruise down a blue. Yogi wanted Corbet’s Couloir.

For those who don’t know: Corbet’s Couloir is the steepest inbounds run in the United States. 4,139 feet of vertical drop at Jackson Hole Mountain Resort. 2,500 skiable acres, 133 runs, and 50% of the terrain rated expert. This is not a place you go to break in your new jacket. This is a place you go if your knees are still on speaking terms with you.

Yogi’s, apparently, were still taking his calls.

Two Minutes

I opened Claude. Gave it the data: four people, one week, flights from Madrid, advanced level. Claude did what Claude does: think. And in under two minutes I had a complete proposal.

Flights: Madrid–Dallas on Iberia, the IB8632 red-eye. Dallas–Jackson Hole on American, AA2028. Landing at 12:36 local time, just in time for lunch and acclimatisation. Return via Chicago and London on British Airways, because direct flights to Jackson Hole from Europe don’t exist and anyone who tells you otherwise is selling something.

Hotel: Elk Country Inn. Jackson, Wyoming. Seven nights, two rooms with Queen beds, American breakfast included, free shuttle to the slopes. A hotel that doesn’t pretend to be boutique or Instagrammable — it pretends to be comfortable, well-located, and with parking for the truck you’re probably going to rent.

Lift pass: five days on the mountain plus one day with a local guide so someone can point out where NOT to drop in if you want to keep skiing the next day.

All of this in two minutes. Real data. Flights that exist. A hotel you can actually book. I verified it. It worked.

And then Claude decided to add local color.

The Guy at the Cowboy Bar

In the proposal, Claude included a section about the town of Jackson. Useful stuff: the Town Square with its famous elk antler arches, Snake River Brewing, the free START Bus shuttle. Things I already knew, but that looked good in a proposal.

And among the recommendations was the Million Dollar Cowboy Bar. If you’ve never been, picture this: a bar where the stools are literally horse saddles. Live country music. Walls lined with wood and relics from another century. It’s the kind of place where you order a bourbon and they serve it without asking which brand, because in Jackson there’s only one right answer.

So far, so good. But Claude, with that tendency of its to be thorough, generated three traveler profiles to contextualize the proposal. One of them was an experienced skier who charged down Corbet’s Couloir “without thinking twice.” That same guy, according to the proposal, after a day on the mountain, headed to the Million Dollar Cowboy Bar, sat on his saddle stool, ordered three bourbons, and somewhere between the second and third decided that the dollar bills people stick to the bar — a tradition, everybody leaves a signed dollar — were a business opportunity. He tried to peel off a few. The bartender called the sheriff. The sheriff, who in Jackson Hole is a real man with a real badge and very little patience for creative tourists, hauled him off to jail.

End of ski day.

I read that and stared at the screen. Then read it again. Then asked myself what you’re asking right now.

Did This Actually Happen?

Because here’s the trap. Corbet’s Couloir exists. The Million Dollar Cowboy Bar exists. The dollar bill tradition exists. The Teton County sheriff exists. The entire scenario is perfectly believable. The details click together like pieces of a puzzle someone assembled with care.

But did it happen? Is there some guy in a Wyoming courthouse with a record for stealing decorative tips?

I don’t know. And that’s exactly the problem.

I’ve been selling travel for 42 years. I’ve been to Jackson Hole. I know the Cowboy Bar. I’ve seen the bills on the bar. And yet, when an AI tells me this story with the same confidence it uses to list Iberia flight numbers, I struggle to tell where fact ends and fiction begins.

If it’s hard for me, with four decades of experience, imagine what it’s like for Yogi when he receives the proposal.

The Tool and the Judgement

Claude built me a flawless trip in two minutes. Real flights, a verifiable hotel, exact resort data. That’s extraordinary. A year ago, that proposal would have taken me an entire morning of comparing flights, calling the American ground handler, and reviewing my notes from the last time I was in Wyoming.

But Claude also dropped in an anecdote that could be real or could be a hallucination wearing cowboy boots. And it presented it with the same confidence it uses for flight schedules.

AI is fast. AI is useful. AI doesn’t distinguish between a fact and a well-constructed story. That’s my job. That’s what they’ve been paying me for over 42 years.

Yogi got his proposal. Without the criminal. The flights, the hotel, the lift pass, the verified restaurant recommendations. The part Claude got right. The part I verified.

And if you want to see how it turned out, the full proposal is here: Jackson Hole - Group February 2026.

The guy from the Cowboy Bar stayed in my personal files. As a reminder that the fastest tool in the world doesn’t replace the person who knows which questions to ask.

And that in Jackson Hole, as in AI, you shouldn’t believe everything they tell you at the bar.

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Next post: “How I assembled a team of 3 AI agents that fought each other” — the Niseko proposal story.

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Giora Gilead · CICMA 2283 · Marbella · Pedalling since 1954