ChatGPT Checkout Retreat, Expedia Reset & UAE STR Cancellations
Good Morning Hospitality
03/09/26
•32m
About
Comments
Featured In
On this week's Good Morning Hospitality, A Skift Podcast, Wil Slickers, Brandreth Canaley, and Jamie Lane break down the latest headlines shaping travel and short-term rentals.
They start with OpenAI walking back plans for in-chat checkout in ChatGPT, a move that shifts the platform back toward discovery rather than transactions and eases pressure on OTAs like Expedia Group and Booking Holdings (NASDAQ: BKNG).
They also unpack comments from Expedia Group’s CFO about how the company has “radically changed the direction” of the business with new performance metrics and strategic priorities.
The team then looks at cancellation trends hitting vacation rentals in the United Arab Emirates, where regional instability is beginning to ripple through bookings, before diving into analysis on whether Airbnb may need acquisitions if it truly wants to “own the entire trip.”
They also highlight Breezeway’s recent funding news following the bonus interview with Jeremy Gall released earlier last week.
Previous Episode
Breezeway just announced a new strategic investment led by Resurgens Technology Partners, and in this GMH Exclusive, Wil Slickers sits down with founder Jeremy Gall to break down what it actually means.
Jeremy shares why Breezeway chose Resurgens, how the partnership changes the company’s next chapter, and what they’re prioritizing in product development. They also get real about AI in hospitality, where it’s delivering value today, where it’s overhyped, and what operators actually need from their tech stack right now.
Connect with Skift
Subscribe to @SkiftNews and never miss an update from the travel industry.
Next Episode
In this special GMH Bonus episode, Brandy Canaley sits down with Roami co-founders Andreas King-Geovanis and Iskander Karimov following the official sale of the Roami brand to CozySuites.
After nearly a decade building one of the largest apart-hotel operators in South Florida and New Orleans, the founders reflect on the journey from startup to exit. The conversation explores how Roami scaled quickly, navigated major industry shifts like COVID, and grew the portfolio through opportunistic expansion and operational hustle.
Brandy, Andreas, and Iskander also share behind-the-scenes stories from the early days of the company, the culture and core values that shaped the team, and the emotional reality of stepping away from a business they spent years building. They discuss why CozySuites stood out as the right buyer, what it means that the Roami brand and employees will continue on, and where each founder is heading next.
It’s a candid look at the highs, challenges, and lessons from building and selling a hospitality company.
Connect with Skift LinkedIn: https://www.linkedin.com/company/skift/ WhatsApp: https://whatsapp.com/channel/0029VaAL375LikgIXmNPYQ0L/ Facebook: https://facebook.com/skiftnews Instagram: https://www.instagram.com/skiftnews/ Threads: https://www.threads.net/@skiftnews Bluesky: https://bsky.app/profile/skiftnews.bsky.social X: https://twitter.com/skift Subscribe to @SkiftNews and never miss an update from the travel industry.
If you like this episode you’ll love
Promoted