Booking Holdings’s CEO weathered the dotcom bubble. He says the AI boom is different

Hello and welcome to Modern CEO! I’m Stephanie Mehta, CEO and chief content officer of Mansueto Ventures. Each week this newsletter explores inclusive approaches to leadership drawn from conversations with executives and entrepreneurs, and from the pages of Inc. and Fast Company. If you received this newsletter from a friend, you can sign up to get it yourself every Monday morning.

Glenn Fogel joined dot-com darling Priceline in early 2000, a year after the “name your price” travel site’s blockbuster initial public offering (IPO). “I joined one week before the Nasdaq peaked,” Fogel recalls. Within a year of his arrival, the stock had cratered to $6 a share. By March 2002, the Nasdaq, a proxy for the burgeoning e-commerce and tech infrastructure companies that went public, plunged 77% from its March 2020 highs. Quips Fogel: “At the time, my mother was wondering whether I still had a job.”

Today, Fogel is CEO and president of Booking Holdings—parent of Priceline, KAYAK, Booking.com, OpenTable, and other brands. His experience navigating the dotcom bubble (more on that in a moment) affords a compelling perch from which to observe the current generative artificial intelligence (gen AI) boom. He sees parallels in the gold-rush mentality of both booms: “There’s lots of investments, lots of new companies,” he says. “Many of them will not make it. Many investors will lose money.” Corporate investment in AI reached $252.3 billion, and private investment in gen AI reached $33.9 billion in 2024, according to data compiled by the Stanford Institute for Human-Centered artificial intelligence.

The key difference between the dotcom bubble and now? “I would say in terms of the possibility for human society, I think the possible transformations from gen AI are so much greater than what was possible from the [startups of] the nineties,” he says.

Fogel points to breakthroughs like Google’s AlphaFold model, which decoded protein folding and could accelerate drug discovery. “Every area really of our society can be greatly improved by using gen AI,” he says. “That’s the thing that’s so exciting.”

Happy travelers

In travel, the stakes may not be as high, but the impact on daily life could be profound. “Maybe we’re not going to save a lot of lives the way that the healthcare industry is going to be able to do, but maybe we’ll make the experience much happier,” he says.

Indeed, the company is already deploying AI to reduce customer-service wait times, using gen AI chatbots that can solve problems instantly. When a human agent does handle a call, the bots generate conversation summaries and next steps—work that previously consumed significant amounts of agent time.

Embracing emerging technology has been key to Booking Holdings’s longevity. When predecessor company Priceline Group bought Booking.com in 2005, it acquired Booking’s prowess in leveraging Google’s paid search and platforms that enabled the business to rapidly test messaging to optimize conversion rates. The company subsequently bought travel search engine KAYAK in 2013 and restaurant reservation platform OpenTable in 2014. Priceline Group changed its name to Booking Holdings in 2018.

The long view

Travel itself is currently experiencing a boom. Despite economic uncertainty, U.S. consumers, especially those at the high-end of the market, are prioritizing travel, with airlines and hotels indicating strong demand for premium products. Indeed, at the end of October, Booking Holdings reported better-than-expected third-quarter earnings and said it continues to see “steady travel demand trends” in the current quarter.

Having led Booking Holdings through the dotcom boom and bust—as well as the COVID-19 pandemic, which led to a near complete shutdown of travel—Fogel acknowledges that nothing goes up forever.

“I don’t know when those bad times are going to come, but they’re going to come sometimes,” he says. Still, he takes the long view: “I do know, in the long run, travel is always going to increase. It is human nature . . . people wanting to travel.”

This time it’s different?

Do you agree that the societal benefits of gen AI companies and technologies dwarf the contributions of the dotcoms? If so, what breakthroughs excite you most? Send your examples to me at stephaniemehta@mansueto.com. I’d love to share your scenarios in a future newsletter.

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