When AI Replaces Google in Travel

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

It is distribution itself.

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

Shaun spent eight years at Expedia building the early supply networks that made online hotel booking possible, two 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, and two and a half years as Chief Business Development Officer at Waymo, the self-driving car company born out of Google X.

He has watched distribution power get created, consolidated and disrupted across multiple industries. Now he is doing it again, this time rebuilding the ticketing infrastructure at StubHub as live events finally start breaking free from a Ticketmaster-era model that looks a lot like the vacation rental industry circa 2008.

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, and why ticketing never got the same memo
• 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, and what Shaun heard in his first 50 meetings trying to make it happen
• 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, and what that means for the operator in South Carolina with 200 units
• How a Boca Raton property manager with a dozen homes built a suite of AI agents to run his books, staffing, and operations, then built a management agent on top of them all
• Why the Uber vs Waymo cost structure is the warning sign for STR operators who have not modernized yet, and the internal bet Shaun lost about whether autonomous vehicles would land as a luxury or a discount product
• 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