Leadership pressure is reshaping short-term rental growth. In this episode, CEO coach Gary Cohen shares why STR founders crack under complexity, how ego and unclear decision rights weaken execution, and what leaders must change to scale sustainably in an AI-driven landscape.

In this episode, Jon Gray reflects on the real work behind enduring travel marketplaces—from instant booking and inventory neutrality to pushing supply standards that protect trust. A grounded discussion on discipline, resilience, and building platforms that hold up over time.

Europe’s STR market isn’t one-size-fits-all. This panel unpacks how leading operators scale across fragmented European markets—balancing regulation, trust, and hyper-local execution with centralized systems—while showing why technology only works when grounded in strong on-the-ground operations.

Woody Marshall is a General Partner at TCV, where he has invested since 2008 across fintech, mobile, and digital media. He currently serves on the boards of companies such as Spotify, GoFundMe, Payeroneer, and Newsela, and has backed category leaders including Airbnb, Netflix, and Nubank. With nearly three decades in venture capital, he brings deep experience in scaling global technology businesses.

Cliff Johnson, Co Founder of Vacasa and President of PadSplit, reflects on rapid growth, operational pressure, and the decisions that shaped Vacasa’s journey.

Amiad Soto, co-founder and CEO of Guesty, shares how he turned a side project in Tel Aviv into one of the world’s leading property management platforms. He opens up about scaling globally, adapting to fragmented markets, and building tech that empowers real-world operators.

Graham Donoghue (Forge Group), Steve Schwab (Casago), and Quirin Schwaighofer (MadeComfy) join Simon Lehmann to explain why no one has built a truly global STR operator and what it really takes to scale across markets.

Brian Egan, Co-Founder and CEO of Evolve, reveals how he turned a small vacation rental startup into a $5B business with 35,000+ properties. He shares lessons on scaling trust, balancing tech with hospitality, and the future of short-term rentals.