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 the tech, as well as the potential of building an “AI Disney.” 

Beyond building chatbots, he foresees AI transforming the storytelling industry. And the tools are already hitting movie theaters and streaming sites; Netflix used generative AI for a scene in sci-fi show El Eternauta, and for the first time ever the Cannes Film Festival featured a full-length AI-generated feature film Hell Grind in May of this year. Chesky sees the presence of AI in visual mediums only continuing to grow. 

The Airbnb cofounder also predicted that hundreds of giant companies like Anthropic will emerge in the future, but there will also be “tens of millions” of small businesses that spring up thanks to AI. 

Now, all it takes is a handful of people to start a company—something that “was inconceivable before,” Chesky said. 

Airbnb did not have further comment to share with Fortune.

Chesky says it hasn’t been easier to build a business in 20 years

While Chesky sees AI as a powerful new tool for entrepreneurs, he acknowledged that many workers see the technology as an unmovable force thrust upon their careers. But he argues that workers don’t have to be passive participants in the AI revolution—they can use the same technology to build something of their own.

“People outside of Silicon Valley feel like AI is happening to them…and it’s changing their job. It’s displacing them,” Chesky said during the podcast. 

“Some of that may be true, and I’m not defending it,” he continued. “But I am saying that everyone has the power now. And that if you have an idea, you can now make something. And it is so much easier to build a company now than it was 20 years ago.”

The barriers to starting an AI-powered company are falling fast, with generative AI making it possible for much smaller teams to build products that once would have required significantly more people and resources. But for many, the technology still appears as a threat; half of U.S. adults say increased use of AI makes them feel more concerned than excited, according to a 2025 Pew Research survey.

And a majority of U.S. workers have yet to get on board. Around 65% say that they don’t use AI much or at all while on the job, according to 2026 Pew data. Aside from existential concerns about their careers and livelihoods, trying out the tools can be daunting. Chesky admitted that he was “intimidated” to experiment with Claude Code and had no clue where to start. So when he spotted an Airbnb employee who was really good at it, he asked to get tutored in the tech. 

Not everyone will have a staffer who can teach them the ropes, the entrepreneur stipulated, but professionals are bound to have a friend with some experience. Plus, YouTube tutorials are always readily available—there’s a low bar of entry to start tinkering with the tools. The most important thing is that professionals get their feet wet with AI, the millennial founder advised. 

“Jump in the pool,” Chesky said. “The water is not cold, it just looks cold. For those that are already in the pool, just don’t get out.”