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 industries 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.