This week, Leo and Sarah are joined by regular contributor Boris Pavlov to dissect the move that just changed the booking game: Ads have arrived on ChatGPT.

Is this a new goldmine for the OTAs, or the ultimate direct booking shortcut for STR hosts? We dive into the "contextualized intent" driving conversion rates 8x higher than traditional Google ads, and the futuristic reality of guests chatting and booking from directly within the AI interface. If you want to know how to optimize your listings for an LLM-driven world where "niche" is the new "global," this is the episode for you.

Is your short-term rental strategy stuck in 2025? In this episode of The Check-In, hosts Sarah and Leo sit down with one of the STR industry's brightest stars, Hailie Maarie, who has built a staggering 70-property empire in just four years. Hailie breaks down her "2026 Host Checklist"—the essential moves that separate surviving hosts from those who scale.

We dive into why "throwing a listing on an OTA" is no longer enough, how to build a brand that attracts both owners and guests, and the secret to balancing high-tech AI with a high-touch human experience. Whether you’re just starting or looking to "cut the fat" from your portfolio, Hailie shares the mindset shifts and systems required to stay relevant in an increasingly competitive market.

Join us as we delve into Kasa's acquisition of Mint House, a strategic move that positions them as one of the largest apartment hotel operator in the US. Discover what this deal could signify for the revenue share model in hospitality, and what it means for the future of urban hospitality specifically.

Join Leo and Damian as they delve into the vibrant world of France's short-term rental industry with Marie Pistinier, at Scale France. Discover how cultural nuances, expectations of international guests, regulatory challenges, and innovative solutions make France a truly unique (and challenging) market to operate in. This episode offers a comprehensive look at what makes France a standout destination for property managers and travelers alike.

In this episode of The Check-In, Leo and Sarah discuss the evolving landscape of property management, emphasizing the importance of the human touch amidst the rise of AI. They explore how property managers can leverage local expertise, maintain strong relationships with cleaning teams, and focus on long-term property health to stand out in a competitive market. The conversation highlights the need for niche specialization and the value of personal connections in enhancing guest experiences.

Join Leo and Damian for this special episode recorded live at Scale France. They're joined on the sofa by Louis Andrews, CEO of OVO Network France, about the unique challenges and opportunities in the short-term rental industry. Discover how OVO Network has carved a niche in the French Alps, the importance of brand identity, and the evolving landscape of direct bookings. Whether you're in the industry or just curious, this episode offers valuable insights into the world of high-end chalet rentals.

Airbnb was built on partnership, but is that era over? 

This week, Sarah and Leo interview Steve Taggert of MyGetaways to dissect the platform’s aggressive pivot toward guest loyalty at the expense of host support. 

We explore the financial impact of commission changes and the growing trend of hosts being sidelined in their own properties. If you’re a host feeling the squeeze, this episode offers vital advice on navigating the new landscape and diversifying your bookings beyond the Airbnb algorithm.

In this episode, Sarah and Leo delve into the complex relationship between southern Europe and its tourism industry. Once a thriving love affair, the region's dependency on tourism is now facing unprecedented challenges. From economic strains to environmental concerns, we explore the factors driving this shift and what it means for the future of these beloved destinations. Join us for the stories behind the statistics as we deep-dive the evolving landscape of tourism in southern Europe.

In the latest episode of The Check-In Sarah and Leo discuss the significant changes happening at Airbnb, including the introduction of hotel inventory and new cancellation policies. They analyze the implications of these changes for hosts and the broader short-term rental industry, emphasizing the need for hosts to adapt to a more competitive landscape. The conversation also touches on Airbnb's Q3 earnings and the strategic shifts that are shaping the future of the platform.

In the latest episode of The Check-In, Sarah and Leo discuss the intricacies of managing short-term rental properties on your own, with Sarah interviewing James Kinnersly, who operates properties in the Canary Islands. They explore the challenges of remote management, the importance of local knowledge, the dynamics of online travel agencies (OTAs), and the impact of regulations on the short-term rental market. The discussion also highlights the role of technology in property management and shares insights from industry events.