Brian Chesky built one of the defining companies of the mobile era. Now the Airbnb CEO looks at the tools available to founders today and feels a pang of regret. Or opportunity.

“Part of me wishes I can be 26,” Chesky said. “Because actually, as amazing as Airbnb is, if I was 26, I could probably do something just as cool.” The tools now are so much more powerful.

He made the comment in a wide-ranging October interview with Silicon Valley Girl host Marina Mogilko. The Fortune article captured the moment. It struck a chord. Chesky, who co-founded Airbnb in 2008 at age 26, once believed he had timed the market perfectly. The iPhone had just launched. Cloud computing removed the need for servers. The App Store offered instant distribution.

But ChatGPT changed his calculus. A company that once required dozens of people can now launch with one, two or three. That possibility was inconceivable before. Smaller founding teams handle work once reserved for larger staffs. The economics of starting a business have shifted.

Chesky’s Internal AI Transformation

Airbnb itself shows what this shift looks like at scale. The company shipped more than 600 features this year, nearly double the previous pace. AI now resolves close to half of customer service requests without human help. Support costs per booking fell 16% year over year. Executives run on AI tutors. Chesky built his own “brain,” an intelligence layer trained on 18,000 Keynote slides and 50,000 Google documents. It cut his meetings in half.

“Most of us CEOs of big companies don’t really know what the hell’s going on in our companies,” he told Business Insider. The AI system gives him total information. No more endless syncs to stay informed.

Yet Chesky draws a firm line. Airbnb will not develop frontier models. It will apply them. The company rolled out AI-powered search in its fall update. Users describe trips in natural language. The system generates filters, highlights features, and creates custom summaries. Voice agents arrive soon for search and support.

But chatbots alone won’t cut it. Chesky has said so repeatedly. A chatbot delivers a few options at a time. Travel demands comparison, visuals, and multi-step decisions. “I think that a chatbot isn’t the right interface for e-commerce,” he explained in the TechCrunch interview published October 1. The current AI search is not the endgame either. Something richer lies ahead. Visual. Multimodal. Agentic.

He envisions the Airbnb app evolving into an agent. Individual agents for explore, customer service, and other areas. Eventually a macro agent that interoperates with others. Apps must become agents. All must connect. The interface must mirror how humans actually experience the world. Text windows won’t suffice. Strapping a jet engine to a bicycle gets you only so far.

And the gap grows. Top performers pull further ahead. Everyone has access to the same models. The difference lies in taste, judgment, and speed of execution. Chesky generates thousands of ideas a year. He picks the ones worth pursuing with discipline. Put on blinders. Stop doomscrolling. The phone kills focus. The computer saves it.

His friendship with Sam Altman shapes his thinking. Altman once told him hiring should consume 50% of a CEO’s time. Chesky took the advice. He now spends three hours a day on recruitment. He reviews candidates his executives want to hire. Pushback is not tolerated. The approach, borrowed from the OpenAI leader, reshaped Airbnb’s talent process. (Yahoo Finance detailed the shift in late September.)

Chesky sits on Y Combinator’s board. He sees the numbers. Most recent batches tilt heavily toward enterprise AI. Consumer applications lag. “There’s been very little progress on consumer AI,” he said in an August interview. ChatGPT remains the high-water mark. A renaissance should arrive in two to three years. Personalized education, visual storytelling, on-demand healthcare. These areas excite him.

He predicts tens of millions of smaller businesses will emerge alongside a handful of new AI giants. One-person companies could reach billion-dollar scale. Building feels easier now than 20 years ago. Experiment. Start small. Don’t let intimidation win.

So what would Chesky build if he were 26 today? He’s coding again, using tools like Claude. He points to education and rich visual content. An AI-powered Disney built on storytelling holds appeal. Avoid pure conversational interfaces. Focus on multimodal experiences that feel natural.

The sentiment echoes across his recent appearances. In the Silicon Valley Girl podcast he stressed that AI accelerates getting ideas into the world. It does not guarantee better ideas. Taste still matters. Judgment still rules.

Airbnb grows faster than its competitors because it embraced this reality early. The executive team became AI-native. The entire organization followed. Chesky calls AI the best development his company has seen. The results speak. More output. Lower costs. Faster iteration.

But he remains restless. The founder who once felt perfectly timed now sees even greater possibility. The tools have grown stronger. Barriers have fallen. New interfaces wait to be invented. New categories remain undefined.

Founders listening to Chesky hear a clear message. The moment favors builders who move fast and think visually. Those who treat AI as power placed in their hands rather than a force that happens to them. Those willing to experiment before the models mature further.

Part of him wishes he could step back into that 26-year-old shoes. The rest of him is busy steering Airbnb toward an agent-driven future. Richer interfaces. Interoperable systems. A company that feels less like an app and more like an intelligent companion for travel.

The rest of the industry watches closely. If Chesky’s track record holds, the changes coming to travel will reshape expectations far beyond lodging. Smaller teams. Bigger ambitions. And interfaces we have not yet imagined.