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Airbnb CEO Brian Chesky says he wishes he were 26 again because the opportunities post-ChatGPT ‘are so much more powerful’

12 0
08.10.2026

Airbnb CEO Brian Chesky says he wishes he were 26 again because the opportunities post-ChatGPT ‘are so much more powerful’

Brian Chesky, the cofounder and CEO of short-term rental giant Airbnb, once thanked his lucky stars for building his business at an opportune moment; When he was a 26-year-old scaling his business back in 2008, Silicon Valley was teeming with opportunity: the first iPhone had just launched, Facebook was taking off, and YouTube was all the rage. 

But in the corner of his mind, he actually wishes he could turn back his biological clock and be a 20-something entrepreneur in the current AI era. 

“Until the launch of generative AI, ChatGPT, I said ‘Thank god I was born the time I did, because now is a tougher time,’” Chesky recently said on the Silicon Valley Girl podcast. “And then post-ChatGPT, part of me said, ‘I wish I was 26 again.’”

“Because actually, as amazing as Airbnb is, if I was 26, I could probably do something just as cool. Because the tools now are so much more powerful.”

Brian Chesky says if he were a new founder today, he’d launch an ‘AI Disney’

The 45-year-old admitted he isn’t sure what he would do in today’s AI era if he were the same age that he was when he cofounded the $95.8 billion rental company. But he threw out a few ideas.

Chesky noted an interest in transforming education and health with........

© Fortune