The Check-In

Leo Walton and Sarah Nan Dupre
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The real scoop on the deals, the data and the drama in short-term rentals. 

  1. 6D AGO

    Why Guests Don’t Come Back (And How to Fix It)

    Discover how to turn one-time guests into loyal advocates with a simple, scalable loyalty loop. In this episode, Steve Haase shares insights on why traditional loyalty programs fall short in the short-term rental world and how to leverage automation and personal touches to boost guest retention. Learn practical tactics like using SMS over emails and personalizing experiences effortlessly. Perfect for hosts and property managers looking to increase repeat bookings and revenue. Tune in to transform your guest experience and bottom line.

    29 min

  2. FEB 11

    Blackpool’s Blueprint: Revitalising the British Seaside with Chris Webb MP

    Is the Great British seaside back? Chris Webb, MP for Blackpool South, joins us to discuss how his iconic hometown is spearheading a national tourism comeback. While many see coastal towns through a lens of nostalgia, Chris argues they are the key to unlocking millions in UK growth. In this episode, we explore: The Infrastructure Gap: Why broken transport links are the biggest hurdle to local economies.Beyond the Weather: Moving away from seasonal reliance through innovative hospitality.Devolution & Power: Why local autonomy is essential for coastal regeneration.The Blackpool Model: How the UK’s most famous resort could provide a blueprint for seaside towns nationwide.From personal stories of Blackpool’s "Golden Era" to the hard truths of modern government support, this is a deep dive into the future of UK tourism.

    41 min

  3. JAN 30

    Is your Airbnb business actually just a job?

    In this episode of The Check-In, Charles Mullany, CEO of Host Genius, discusses the critical transition from viewing property management as a job to recognizing it as a business. He emphasizes the importance of outsourcing, particularly hiring an executive assistant, to reclaim time and focus on growth. The conversation explores the challenges of owner retention, operational scaling, and the necessity of trust in delegation. Charles shares insights on effective strategies for growth, the significance of understanding business identity, and the operational hurdles faced when scaling beyond a certain number of properties.

    30 min

  4. JAN 23

    ChatGPT Ads: a Game-Changer for STR Hosts?

    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.

    14 min

  5. JAN 20

    Adapt or Fade: The 2026 Checklist for High-Performance STR Hosting

    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.

    33 min

  6. JAN 15

    The Asset-Light Advantage: Why Kasa is Scaling While Others Are Crashing

    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.

    11 min

  7. JAN 13

    Why France is the Hardest Place to Run an STR business Right Now

    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.

    17 min

  8. JAN 9

    The Human Moat: How to Prove Your Value When AI Wants to Replace You

    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.

    30 min
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About

The real scoop on the deals, the data and the drama in short-term rentals. 

Information

  • Creator
    Leo Walton and Sarah Nan Dupre
  • Years Active
    2025 - 2026
  • Episodes
    15
  • Rating
    Clean
  • Copyright
    © 2026 The Check-In
  • Show Website
    The Check-In