Building Travel Marketplaces That Actually Endure

Some platforms optimize for growth. Others optimize for survival. Very few manage both.

In this episode of STR Global Unlocked, Simon Lehmann sits down with Jon Gray, CEO of RVshare and former executive at HomeAway (now VRBO), for a grounded conversation on what actually makes marketplaces last.

Jon has seen multiple cycles from the early days of short-term rentals, through the $3.9B sale of HomeAway to Expedia, to scaling the largest RV rental marketplace in the world. This is not a discussion about categories, labels, or hype. It is about discipline, tradeoffs, and building platforms that hold up when demand shifts.

Throughout the conversation, Jon returns to one core idea. Marketplaces exist to remove friction and expand real choice. Everything else follows from that.

In this conversation, we discuss:

• Why the true job of a marketplace is removing friction and delivering meaningful consumer choice, regardless of category.
  
  
• What felt uncertain in the early HomeAway days but later proved obvious, including instant booking and inventory neutrality.
  
  
• Why guests prioritize experience quality over who manages the inventory, and what that means for professional operators.
  
  
• How RVshare translated STR marketplace fundamentals into a higher-friction, mobile asset class.
  
  
• Why pushing supply sophistication faster than feels comfortable protects long-term experience and reputation.
  
  
• Why resilience, unit economics, and survivability matter more than valuation narratives during growth cycles.

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