Artificial Intelligence Can Change Everything: Brian Chesky, CEO, and Project Manager at WIRED, in San Francisco, April 17 – 2025
The company could be changing 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. Chesky thinks that the value of physical experiences and community trump most digital Experiences in the age of Artificial Intelligence.
Chesky said that in the past, people thought self-driving cars would be all over America. We may underestimate how much technology will change in the long term, but we overestimate how little it will change in the short 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.”
Chesky has been talked about in Silicon Valley because of phrases such as “founder mode” and his decision to no longer take one-on-one meetings.
He said that when he lost 80 percent of his business in eight weeks, he was much more involved in day-to-day details of what his staff was doing. Chesky has between 75 and 80 projects he monitors at a time and dedicates half his day 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.
Cook also contends that Apple has been preparing for the AI revolution all along. For the past year, he has made a point of courting John Giannandrea, a senior vice president of the company, for an expansion of his ranks. He pulled the plug on the smart-car program and put the machine-learned talent of the company to work on its software products.
Apple revealed in June a layer of artificial intelligence for its entire product line. Cook brokered a deal with the gold standard of Openai that would let his users have access to the chat room. I’d gotten a few demos of what they were planning to reveal, including a tool to create custom emoji with verbal prompts and an easy-to-use AI picture generator called Image Playground. (I hadn’t yet tested the revivification of Siri, Apple’s lackluster AI agent.)
Cook didn’t panic. Like Steve Jobs, he doesn’t believe in the first being the best. With a strong grasp of novelty versus utility,Classic Apple picks products that make the latest technologies relevant and even sexy. Think back to how the iPod rethought digital music. It wasn’t the first mp3 player, but its easy to use, compactness, and integration with an online store made it appealing to people.
I often think about a tour I took months before construction began, when there was dust on the floors and mud where the plants were growing. Tim Cook was the CEO of Apple. The proprietor told me that I had to commit to the new campus in 100 years.