Brian Chesky Says Big Things Are Coming for Airbnb in 2025

Big changes could be coming to Airbnb next year. In a conversation at WIRED’s Big Interview even in San Francisco on Tuesday, the company’s cofounder and CEO Brian Chesky told global editorial director Katie Drummond that he hopes that, in 2025, “people say ‘that was one of the biggest reinventions of a company in recent memory.’”

Though Chesky kept details scant, he did say that the company hopes to reimagine its Experiences section, which he says consumers really like but that he doesn’t think has caught on as much as it could. The move seems to be an extension of Chesky’s belief in the value of physical experiences and physical community, which he still thinks trump most digital experiences, even in the age of AI.

In an effort to prove that, even two years into the AI revolution, fundamentally very little has been changed for most people, Chesky challenged the room to look at the apps on their phone home screens and think how much any of them have been substantially changed by generative AI. He posits that it’s very few, including Airbnb, but he also sees change on the horizon, likening the AI adolescence we’re in to the “internet of 1993, before search engines” when you’d use what he called ”a phone book” to find websites.

“AI is beginning to change our digital world, but it has not yet changed the most important part of our lives, which is the physical world,” Chesky said. At Airbnb, where the product isn’t the company’s app but its connected homes and experiences, that’s still what’s valued most. When AI will truly start to change the physical world, Chesky posits, is “when the apps on your phone are totally different.”

“Ten years ago, everyone thought we’d all be in self-driving cars right now,” Chesky said, noting that while there are a lot on his street, they haven’t permeated the rest of America. “We overestimate how much technology can change in the short term, but we probably underestimate how much it will change in the long term. AI is going to take some time to permeate the physical world but once it does, I think it’s going to change everything.”

Drummond also questioned Chesky about his leadership style, which has become much talked about in Silicon Valley because of phrases like “founder mode” (which he noted he didn’t actually coin) and the much-publicized notion that he doesn’t take one-on-one meetings anymore.

He said that since the pandemic, when Airbnb lost 80 percent of its business within eight weeks and was forced to lay off about a third of the company, he’s been much more involved in the day-to-day details of what his staff is doing, telling Drummond that he thinks it’s important to mentor people through work. Chesky says he monitors between 75 and 80 projects at a time, dedicating half of his 60-plus-hour work week to project reviews each week. While he might not do recurring, scheduled one-on-ones anymore, he says he does a lot of individual phone calls and leans in to group meetings, where he can meet with multiple levels of staff at once.