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

Brian Chesky thinks the best startup timing may be now, not 2008. That’s a sharp turn from the Airbnb cofounder’s older view of the world, when the first iPhone had just launched, Facebook was climbing fast and YouTube was everywhere. Back then, he was 26 and building Airbnb. Today, he says the post-ChatGPT era looks even more open to young founders.

On the Silicon Valley Girl podcast, Chesky said he once felt grateful to have been born when he was, because the AI era seemed harder for new entrepreneurs. Then generative AI arrived, and his view flipped. “I wish I was 26 again,” he said, adding that he could probably build something just as cool as Airbnb because the tools are now much more powerful.

He’s not pretending the answer is obvious. Chesky, now 45, said he isn’t sure what he would build today, but he floated a few directions: education, health, and an “AI Disney.” He also thinks AI will move far beyond chatbots and into storytelling, where it’s already showing up in public. Netflix used generative AI for a scene in El Eternauta, and the Cannes Film Festival featured a full-length AI-generated feature film, Hell Grind, in May.

That’s the bigger point in Chesky’s telling: AI won’t just create a few giant winners. He predicts hundreds of companies like Anthropic will emerge, along with “tens of millions” of small businesses that can get started with just a handful of people. What used to take large teams and more money, he argues, is now within reach for far fewer people.

He also knows plenty of workers see AI as a threat rather than a tool. But he pushed back on the idea that people have to just take it. He said he was intimidated when he first tried Claude Code and needed help from an Airbnb employee. His advice was simple: use the tools, learn them, and don’t stand outside the pool complaining about the temperature.