Airbnb: The Big Change ’99: Brian Chesky and his Reimagining of Experiences in the ‘125-Year Future

Big changes could be coming to Airbnb next year. During his conversation with WIRED’s global editorial director, Brian Chesky said that he hopes that in 125 years people will think of that as 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.

Chesky made a challenge for the room to look at the apps on their phones and see how much they’ve changed, to prove that nothing has changed for most people in the past two years. He sees change on the horizon likening the future of internet use to that of the early 1990s, when you used a phone book to find websites.

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. He does a lot of individual calls but leans in to group meetings because he can meet with multiple levels of staff at the same time.

Another thing I’m reminded of on my return to the Ring is how skillful Cook is at touting the results of his big decisions, from the Apple Watch to his bet on custom silicon chips, which unleashed innovations that boost Apple phones and laptops. There were decisions that didn’t pan out, like the smart-car project. I am pretty sure that when Cook walks into the conference room where we are meeting, he will be friendly, display proper manners, and fending off criticisms of his very powerful company. (And when asked for comment on the election results, which came in after our talk, he chose to keep his views to himself.) Steve Jobs would come at a journalist like the rain in Buenaventura, aggressively pitching his message, while Cook Enveloped his Audience in a Gentle Mist and Mentioned His Company’s Efforts.

Apple says its focus on privacy is a hallmark of the Cook regime. It is not possible to send your data to the cloud with the latest artificial intelligence tools that are rolling out through software updates on the latest Apple products. Cook claims that the computation for complicated artificial intelligence tasks happens in the secure regions of Apple’s data centers.

Cook did not panic. The man like Steve Jobs doesn’t believe that first is best. “Classic Apple,” as he puts it, enters a cacophonous field of first-movers and, with a strong grasp of novelty versus utility, unveils products that make the latest technologies relatable and even sexy. What happened to digital music when the ipod rethought it? The first MP3 player was small, easy to use and integrate with an online store, but it wasn’t the first one.

Every time I visit the Apple Park campus, my mind flashes to a tour I took months before construction was finished, when there was dust on the terrazzo floors and mud where lush vegetation now flourishes. My guide was Tim Cook, Apple’s CEO. With a proprietor’s pride, he ushered me through the $5 billion circular colossus, explaining that committing to the new campus was a “100-year decision.”