Brian Chesky
CEO of Airbnb
The Airbnb co-founder and CEO calls an AI travel agent the industry’s “Holy Grail” and is rebuilding the app around AI search and what he says is the best AI customer-service agent in travel — while advising Sam Altman through OpenAI’s stormiest moments.
In his words
The Holy Grail is becoming more like an AI travel agent that’s the ultimate agent that can learn about you, and understand you.
We’re not going to be a leader in AI research. And we’re not going to be developing large language models. But where we can be a leader is “applied AI.”
Biography
Brian Chesky (born 1981), a Rhode Island School of Design graduate, co-founded Airbnb in 2008 by renting air mattresses in his San Francisco apartment and grew it into the defining marketplace for travel lodging. Design-obsessed and famously hands-on, he has made AI the organizing idea of Airbnb’s next act.
From search box to concierge
Chesky told Fortune in November 2023 that the “Holy Grail” for Airbnb is an AI travel agent that learns and understands each guest, positioning the company as a leader in “applied AI” rather than model-building. The rebuild began shipping in 2025: an AI customer-service agent — which Chesky says is the best in all of travel, trained on hundreds of millions of stay-related data points — rolled out to U.S. users, with AI search and messaging planned to merge into a single concierge that handles the trip end to end. In October 2025 he explained that Airbnb had held off integrating ChatGPT because the SDK “wasn’t quite robust enough,” while predicting that specialization will win in travel.
Chesky is also personally wired into the AI world’s power center: a close friend of Sam Altman, he was widely reported to be among Altman’s key informal advisers during OpenAI’s November 2023 board crisis, and he remains one of the consumer-tech CEOs most publicly invested in the agentic-AI future — betting that AI agents will book travel through platforms like his rather than around them.
Where they stand in the war
Who backs them up
Sources & further reading
Canonical record: https://battlelines.ai/topic/brian-chesky