United Airlines CEO Scott Kirby loves gambling, and now he’s using AI as an ace up his sleeve.
Speaking on the “Cheeky Pint” podcast, Kirby said that over the past eight months, he’s had an “AI epiphany” about the tech’s best uses, which was triggered by one of his favorite pastimes — sports betting.
“Summarizing documents and all that crap, I think it’s ridiculous,” Kirby said. “I can read my calendar. I don’t need to summarize my day.”
Instead, he has found vibe coding far more valuable.
Kirby told “Cheeky Pint” host and Stripe cofounder John Collison that he hired a tutor for three hourlong sessions, then used AI to make a webpage for sports gambling.
“I’ve always been into gambling. For better or worse,” Kirby said.
Between sets in a two-and-a-half-hour gym session, he typed prompts on his iPad to vibe-code a page with “four or five” drop-down menus for different sports, dates, and bets. Kirby said it links to four sportsbooks and pulls up the best odds; then he can enter a dollar amount, and it places the bet for him.
“I could do it with three hours of tutoring on my own, could write a program to do that, was an epiphany for me,” Kirby said. “I think I called them on that Saturday, our team, and like, ‘We’re all in on this.'”
His appetite for risk has helped Kirby make bets on airline strategy that have paid off. For example, when carriers around the world retired their airplanes during the pandemic, United instead ordered hundreds of new jets — buoying the airline when travel demand boomed after lockdowns ended.
The United CEO previously spoke about his love for gambling in an April interview with The Wall Street Journal, where he described being kicked out of casinos for counting cards before he started in the airline industry.
He told “Cheeky Pint” that he went back to Las Vegas when the Super Bowl was held there in 2024.
After setting up a credit line to play poker, he had to hand over his ID.
“It was like 15 years ago that I got barred at the Bellagio last time,” he said. “The manager comes over, and he’s like, ‘Mr. Kirby, you’re welcome to play any game in the casino, but just so you know, still no blackjack.'”
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