Airbnb’s Brian Chesky is putting together — and seeking funding for — an AI Lab that would be separate from Airbnb. Is he building it to enhance Airbnb’s AI capabilities, or is it that he can’t resist immersing himself, like his buddy Sam Altman at OpenAI, in the next big thing?
In 2017, then-Expedia CEO Dara Khosrowshahi became CEO of Uber, drawn by what was seen at the time as a once-in-a-lifetime opportunity in the gig economy. Was building an AI Lab just too much for Chesky to resist? Chesky is keeping his day job at Airbnb, of course, but where will his passion be?
ZS + SKIFT
The premium play with the highest return potential will likely come through customers brands already serve. Start with the one or two of these personas who already move through the business in volume, and build from there.
EDITOR’S PICKS
Amadeus’ New AI Tools Are Part of a Bigger Hotel Booking Plan — Exclusive
June 16, 2026
Amadeus will publicly introduce two hotel AI tools at HITEC, but its bigger play is infrastructure. As AI agents move closer to travel booking, the GDS wants to help define how hotels are found, priced, changed, and paid for.
Expedia Names Ex-Pinterest Exec to Lead Ads. The Pitch: Real Bookings, Not Intent.
June 1, 2026
Expedia's advertising program has one thing that Google and Meta can't offer — confirmed bookers. As such, advertisers can target travelers with set plans and try to entice them to book additional products.
SKIFT PODCAST NETWORK
In this clip, Vipul Hingne explains Booking’s core principle for AI (and any tech at scale): shipping is not enough. If you deploy something without the ability to operate it, it won’t work.
SKIFT TRAVEL 200
How are public travel tech companies performing around the world? The Skift Travel 200 pulls the data you need to know to understand the market. Paid subscribers get full access here.
