


Three travel-industry stories from the Skiff Global Forum: Airbnb’s AI agent plans, Barry Diller’s MGM deal pause, and investor bets on “AI-proof” travel assets.
The episode is a briefing by Sarah Dandeshi. It features statements from Airbnb CEO Brian Chesky (virtual appearance), Barry Diller (People Inc., 27% MGM stake), and investors Steve Case and Greg O’Hara (O’Hara’s firm owns ~14 longevity/wellness resorts; Steve Case is a major travel/tech investor).
Airbnb will launch its own visual AI travel agent in 2027 (not a chatbot); unlike Booking.com/Expedia already in ChatGPT, Airbnb won’t rely on chat. Diller withdrew an ~$18B MGM bid because the deal “mix” wasn’t right, though People remains open to alternatives. Case/O’Hara argue AI commoditizes digital travel, increasing value of physical, scarce experiences.
O’Hara’s resorts grow 30–35% annually; ~€300M investment in France; Amex GBT sold for $6.3B to an AI-focused buyer; “mountain view” as an example AI can’t replicate.
Written by AI. May contain mistakes.
Brian Chesky's announcement about Airbnb's AI travel agent plans for 2027.
“So first up, Brian Chesky took the stage, albeit virtually, at the SCIF Global Forum and said something that you can hold him to.”
Discussion about Barry Diller's decision to withdraw his bid for MGM Resorts.
“Next up, Barry Diller just withdrew his roughly$18 billion bid to take MGM Resorts private.”
Insights from investors on the AI boom and its influence on valuable travel experiences.
“O 'Hara's firm owns about 14 longevity and wellness resorts, growing 30 to 35 percent a year.”

Get the gist, explore an idea or ask about something said.
On Skift Daily Briefing, what are the key points of this episode?
Automatic transcript. May contain errors.
0:10Sarah Dandashy: Well, here we are just wrapping the Skiff Global Forum in New York, and these are three stories that are worth your full attention. Airbnb's CEO just put a date on his AI agent, Barry Diller walked away from an$18 billion MGM deal, and two of travel's biggest investors just told us exactly where the smart money is going. It's Friday, September 25th. I'm Sarah Dandeshi, and this is the SCIF Daily Briefing. So first up, Brian Chesky took the stage, albeit virtually, at the SCIF Global Forum and said something that you can hold him to. Airbnb will launch its own AI travel agent in 2027. Not a chatbot, but something richer, more visual, built for how people actually shop for travel.
0:50Sarah Dandashy: But here's what makes this interesting. Booking.com and Expedia are already inside ChatGPT. Airbnb is not. And Chesky is betting that the chat interface is the wrong format for travel. You browse, you imagine, you compare. But that's not a text conversation. So instead of just joining someone else's platform, he's building his own front door. He also said Airbnb will eventually welcome hotel chains like Marriott and Hilton, and one day, maybe even flights. The company that used to be only about homes is quietly becoming something much bigger. Next up, Barry Diller just withdrew his roughly$18 billion bid to take MGM Resorts private.
1:29Sarah Dandashy: His company, People Inc., holds a 27 % stake in MGM and had been preparing to buy the rest. This week, he said the mix just wasn't coming together, and he walked away. MGM controls 40 % of the Las Vegas Strip's hotel rooms. Strip occupancy was flat last quarter, and average daily rates fell 4%. Value-driven visitors are pulling back. The timing wasn't right, but Dillard didn't close the door. He said People remains open to a range of alternatives and still has total confidence in MGM's management. The story isn't over, it's just paused. And finally, the most interesting conversation of the whole forum, Steve Case and Greg O 'Hara, two of Travel's most active and respected investors, said that the AI boom is actually pushing them towards things AI can't copy, which is land, luxury homes, wellness resorts, high-speed trains.
2:21Sarah Dandashy: O 'Hara's firm owns about 14 longevity and wellness resorts, growing 30 to 35 percent a year. They're putting roughly 300 million euros into France, and they're selling Amex GBT, the world's largest corporate travel company, to an AI-focused buyer for$6.3 billion. Now, the logic here is that the more AI commoditizes digital travel, the more valuable physical, scarce, irreplaceable experiences become. You can't prompt an engineer a mountain view, for example. And that's a mindset worth carrying into whatever comes next in the travel industry. Well, this is it for your Skiff Daily Briefing. For more industry news, head to skiff.com and as always, subscribe at skiff.com backslash daily.
3:04Sarah Dandashy: Thanks so much for listening.
Brian Chesky commits to launching Airbnb's AI travel agent in 2027 and bets the chat interface is the wrong format for travel, Barry Diller walks away from an $18 billion MGM deal but leaves the door open, and two of travel's biggest investors reveal they're putting their money into things AI can't copy.
On today's Skift Daily Briefing, Sarah Dandashy breaks down why Airbnb is building its own front door instead of joining ChatGPT, what Diller's MGM withdrawal says about the timing of big Strip consolidation bets, and why the smartest travel investors are chasing land, wellness, and high-speed trains in an AI-commoditized world.
This episode is brought to you by ZS
Articles Referenced:
Honorable Mention: @AskAConcierge on IGBrian Chesky Commits to Launching an AI Agent in 2027Barry Diller Withdraws MGM Resorts BidRevolution's Steve Case and Certares' Greg O'Hara Are Betting on Scarce Travel Assets
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