In this episode, hospitality innovator Chip Conley explains how Airbnb reshaped hospitality by prioritizing dependability over rigid consistency. He shares how reviews, Superhost incentives, and guest psychology helped scale trust while preserving the human side of hospitality.

Luxury short-term rentals have long been seen as the most resilient segment of the STR market — but today’s environment is testing that assumption. In this global roundtable, Simon Lehmann speaks with the CEOs of Emerald Stay, Le Collectionist, The Luxe Nomad, and Nocturne Luxury Villas about shifting demand, pricing discipline, margin pressure, regulation, brand ownership, and what it truly takes to build a scalable luxury STR platform in a more selective and cost-sensitive market.

STR, mid-term, and multifamily housing are converging inside the same assets, forcing new operating and pricing models. Fred Lerche explains why flexible living is becoming a core strategy for institutional real estate, driven by risk management, regulation, and asset protection.

In this solo episode, Simon Lehmann explains why winning in 2026 is less about forecasts and more about disciplined decision-making. He breaks down six critical decisions—from pricing and operations to regulation, risk, and distribution—that will define margins, resilience, and long-term success for professional STR operators.

Institutional capital is reshaping short-term rentals and flexible living. In this episode, Jaja Jackson of ICONIQ Capital shares how investors assess STR, mid-term stays, risk, returns, and operational integration at scale.

This episode explores how capital raising is shifting from traditional, opaque models to more open, ecommerce-like platforms. DealMaker CEO Rebecca Kacaba shares why online, community-driven fundraising is giving founders more control, flexibility, and access to capital—especially in real estate, hospitality, and short-term rentals—while AI helps reduce friction across the process.

Bobby Healy, Founder and CEO of Manna Drone Delivery, joins STR Global Unlocked to explain why last-mile delivery is fundamentally broken and how autonomous drones can transform logistics, urban operations, and the short-term rental guest experience. Drawing on decades of travel and infrastructure expertise, he breaks down the real economics, regulatory realities, and operational limits shaping drone delivery at scale.

A reflective Holiday Special where Simon Lehmann breaks down how 2025 reshaped the STR industry—shifting the focus from rapid growth to margins, execution, regulation, and operational reality. A grounded look at the conversations, tensions, and signals defining where short-term rentals stand today and what lies ahead.

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.

Jeff Hurst and Cami Narino from Furnished Finder join Simon Lehmann to break down why midterm rentals are rising, how independent landlords built more than 300,000 listings, and what operators need to understand as monthly stays reshape housing and hospitality.

Simon Lehmann speaks with Glenn Fogel, President and CEO of Booking Holdings, about how AI, search and short term rentals are shaping Booking.com’s strategy and the next phase of global travel.

The short-term rental industry is entering a decisive moment. Regulation is rising, OTAs are shifting power, and AI is changing the game. Simon Lehmann unpacks the six trends defining STR in 2025, sharing sharp insights from decades in the global market.