025: Guests Aren't Googling Anymore: AI, OTAs & the Future of STR Distribution | Shaun Stewart

The biggest disruption coming to short-term rentals is not regulation, supply growth, or capital compression. It is distribution itself.

In this episode of STR Global Unlocked, Simon Lehmann sits down with Shaun Stewart, VP of Open Distribution at StubHub and one of the most consequential behind-the-scenes figures in the history of modern travel infrastructure. 

Shaun spent 8 years at Expedia building the early supply networks that made online hotel booking possible, 2 years as Global Head of Vacation Rentals at Airbnb where he helped make instant booking a reality in a category that had never transacted live.

He has watched distribution power get created, consolidated and disrupted across multiple industries.  This is not just a conversation about tactics. It is also a structural argument for why everything STR operators assumed about distribution is about to be renegotiated.

In this conversation, we discuss:

• How a chance encounter on a flight in the 1960s between two executives named Smith gave birth to Sabre, the GDS, and the entire modern travel distribution infrastructure.
• Why the moment Airbnb pushed vacation rentals into live inventory transactions was the most important and most resisted shift in the history of the category.
• How AI is replacing Google as the top of funnel and what happens when ChatGPT and Gemini start taking commercial deals from OTAs to influence what they recommend
• Why owning and controlling your own inventory source of truth is more strategically important today than it has ever been.
• How a Boca Raton property manager with a dozen homes built a suite of AI agents to run his books, staffing, and operations.
• Why the Uber vs Waymo cost structure is the warning sign for STR operators who have not modernized yet.
• Why Shaun admits he would have bailed on Airbnb long before it became Airbnb, what the Sonder S1 got wrong about direct booking, and which single infrastructure layer he would own if he could only pick one

Explore more:

Connect with Shaun Stewart on LinkedIn [https://www.linkedin.com/in/shaun-stewart-07b47b1/] and learn more about StubHub [https://www.stubhub.com]

Podcast supported by Pricelabs

PriceLabs brings automated pricing and market intelligence together in one platform trusted by property managers at scale. 👉 Get started with Pricelabs here: https://shorturl.at/wvKTa 

Resources

• AJL Atelier – Global STR Consulting [https://www.ajlatelier.com]. Led by our host Simon Lehmann, AJL Atelier is a boutique advisory firm helping professional hosts, property managers, and investors succeed in the short-term rental industry.
• Connect with Simon Lehmann on LinkedIn [https://www.linkedin.com/in/simon-lehmann-8375753b/] 

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