Stranded on a Denver tarmac, Booking.com’s CEO envisions the AI that should have rerouted him to Aspen before takeoff

On his way to Fortune’s Brainstorm Tech conference this week, Booking.com’s CEO Glenn Fogel faced an all-too-familiar travel blunder. 

Fogel had flown from New York to Denver and was set toward Aspen, only to board his connecting flight, push back from the gate, sit on the tarmac, and then be taxied back to the gate. Ryan Serhant, the celebrity real estate broker and CEO of brokerage Serhant who shared the stage with Fogel and Term Sheet editor Allie Garfinkle on Tuesday, had gone through the same ordeal on a separate flight that same day. 

But as Fogel sat on the tarmac, he thought about the type of travel assistant he wanted to build for the future using AI. The assistant he wants, he told the audience at Brainstorm Tech, would have intervened hours before his debacle, warning him the weather in Denver looked bad and would’ve had a menu of backup options waiting for him. That could’ve looked like offering a four-hour drive, a car service, or shuttle to Aspen, the CEO of the $125 billion travel company said.  

“We believe the........

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