STR Global Unlocked with Simon Lehmann: Unfiltered knowledge for the short term rental industry
The short-term rental industry is evolving fast, and Simon Lehmann isn’t afraid to say what others won’t.
STR Global Unlocked is where property managers, STR tech founders, vacation rental investors, and hospitality leaders get real about the business. Each episode breaks down what’s working, what’s broken, and what’s coming next: property management operations, direct bookings, vacation rental software, pricing strategies, mergers and acquisitions in real estate, professional host challenges, and the future of automation, AI, and tech stacks.
Hosted by Simon Lehmann, CEO of AJL Atelier and one of the most trusted voices in the global STR space, the show delivers unfiltered conversations with the people shaping the industry. Simon has decades of experience in vacation rentals, travel tech, and hospitality, including leadership roles at Vacasa Europe, PhocusWright and HomeAway.
If you’re scaling a property management company, building short-term rental technology, investing in vacation rentals, or entering this fast-moving market, this podcast is your seat at the table.
STR Global Unlocked with Simon Lehmann: Unfiltered knowledge for the short term rental industry
019: Travel Marketplaces That Endure: Lessons from HomeAway to RVshare with Jon Gray
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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.
Resources and links:
Connect with Jon Gray on LinkedIn [https://www.linkedin.com/in/jonathangray/] to learn more about RVshare [https://rvshare.com/]
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/]
Stay connected:
- Apple Podcasts: https://podcasts.apple.com/us/podcast/str-global-unlocked-with-simon-lehmann-unfiltered/id1842946960
- Spotify: https://open.spotify.com/show/3kke4wOx0tNv0duq9MMWtO
- Youtube: https://www.youtube.com/playlist?list=PLWVkmUOkmhSHcFjzi28AhaQNR98vaG65O
- Website: https://www.ajlatelier.com/podcasts
- Newsletter: https://str-global-unlocked.beehiiv.com/