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The Check-In

The Check-In

De : 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.

© 2026 The Check-In
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  • SCALE Fest 2026 preview with Damian Sheridan
    Oct 2 2026

    With Scale Fest in Barcelona during around the corner Damian jumps on the pod with Leo and Sarah to them all about the event!

    What makes a conference genuinely useful? The gang discuss how SCALE creates space for professional property managers to learn, connect, and share ideas—without the hard sell. They also preview Scale Fest Barcelona’s standout sessions, from a US-versus-Europe debate to a lively round of real-life hosting stories, and explore why human connection still matters in an AI-driven world.



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    21 min
  • Luxury Vacation Rentals: How Hospitality Builds Guest Loyalty
    Sep 30 2026

    How do you build a successful luxury vacation rental business—and deliver an experience guests remember? Rachel Alday, co-founder and co-owner of Abode Luxury Rentals, joins The Check-In to share how she and her husband grew their company to manage around 200 properties across Park City, Jackson Hole, and Sun Valley.

    Rachel explains why they focused on luxury vacation rentals early on, how professional property management is changing the market, and what it takes to earn the trust of high-end homeowners and guests. She also breaks down Abode’s approach to luxury hospitality, including multiple property inspections, in-person guest arrivals, and concierge services that help create a memorable stay.

    The conversation goes beyond operations and revenue to explore Rachel’s idea of the “hospitality gene”: the human care and connection that build guest loyalty and stronger teams. Rachel also discusses her book, Please Do Disturb, and why connection matters in hospitality and leadership.

    If you’re a vacation rental manager, property owner, or hospitality professional, this episode offers insights on luxury vacation rentals, guest experience, concierge service, and building a people-first hospitality business.

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    35 min
  • Stop Being the Cheap Option — Garrett Brown on Experience Led STR
    Sep 11 2026

    Leo and Sarah return after a break for summer, and they're right back in with an episode packed with insights; an interview with Garrett Brown.

    Garrett sold his city condos, moved an hour outside Houston, and built Cameron Ranch Glamping from a single geodesic dome into a 20-unit resort doing $450-500 per night. He now reaches 90% direct bookings and sends every guest a custom AI-generated song before they arrive.

    He joins Leo and Sarah to talk about knowing your guest avatar, why the experience has to justify the price, how AI is making his team more human not less, and what he'd tell anyone looking to invest $500k in STR right now.

    Sharp, practical and genuinely fun — this one's worth your time.

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    36 min
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