Inside VC Thinking on STR

Woody Marshall is a General Partner at TCV, one of the most influential investment firms in global technology and a long-standing backer of travel companies including Expedia, Airbnb, HomeAway and TripAdvisor. With more than two decades of experience investing in category-defining platforms, Woody brings a unique view of how technology evolves and what it takes for a company to break through in fragmented markets.

In this episode, Simon Lehmann speaks with Woody about the state of short-term rental technology, why investor appetite has shifted and how AI, consolidation and new competitive pressures are reshaping the landscape. Woody explains how TCV evaluates opportunity, why STR technology has different valuation dynamics than traditional SaaS and what founders should understand as they build in an increasingly crowded space.

This conversation offers an unfiltered look at how top-tier investors see the market and what it will take for the next generation of STR technology companies to stand out.

In this conversation, we discuss:

● How TCV approaches travel technology and why STR platforms require a distinct investment lens.

● Why fragmentation across PMS, operations, revenue tools and distribution makes scale difficult to achieve.

● How AI is reshaping search, personalization and product experience and what this means for STR platforms.

● Why consolidation is likely and where the market may converge as the tech stack evolves.

● How competitive dynamics with incumbents and AI-first entrants affect valuation, defensibility and long-term strategy.

● What founders must demonstrate today to compete, differentiate and attract institutional investment.

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