The Check-In
The real scoop on the deals, the data and the drama in short-term rentals.
Episodes
15 episodes
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 autom...
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Season 1
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Episode 15
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28:49
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 ar...
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Season 1
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Episode 14
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41:14
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 ...
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Season 1
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Episode 13
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30:04
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 ...
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Season 1
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Episode 12
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13:30
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 y...
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Season 1
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Episode 11
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33:12
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...
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Season 1
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Episode 10
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11:28
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 so...
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Season 1
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Episode 9
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17:07
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...
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Season 1
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Episode 8
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30:01
Why Brand Identity is Killing (or Saving) Your STR Business
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 OV...
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Season 1
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Episode 7
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17:58
The Guest-First Trap: Why Airbnb is Losing Its Best Hosts
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 e...
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Season 1
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Episode 6
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36:03
The Breakup: Why Southern Europe’s Love Affair With Tourism is Coming to an End
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 t...
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Season 1
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Episode 5
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35:47
Has Airbnb Outgrown the Host Community?
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 t...
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Season 1
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Episode 4
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27:20
Does the Airbnb Side-Hustle Still Work? A Host Shares Everything
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 challeng...
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Season 1
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Episode 3
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35:51
Will AI Agents Kill the OTAs? Google Just Made Its Move
In this week's episode of "The Check-In," hosts Sarah Nan DuPre and Leo Walton dive into the transformative impact of Google's new AI travel tools. Joined by Boris Pavlov, founder and CEO of Flataway, they explore how Google's AI is reshaping t...
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Season 1
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Episode 2
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40:39
The Sonder - Marriott Meltdown
In this first episode of "The Check-In," hosts Sarah Nan DuPre and Leo Walton dive into the dramatic collapse of Sonder, exploring its impact on the short-term rental industry in general and Marriott specifically. Joined by expert Ben Painter, ...
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Season 1
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Episode 1
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33:35