The Check-In
The real scoop on the deals, the data and the drama in short-term rentals.
Podcasting since 2025 • 20 episodes
The Check-In
Latest Episodes
STR News Round Up
New York's 'own goal', the AI voice revolution and a preview of the latest Scale events: What happens when a global event like the World Cup meets hyper-restrictive rental regulations? Leo is joined by Steve Taggert and Damian Sher...
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Season 1
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Episode 20
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30:24
Using the Best Hotel Systems for STR Success
The short-term rental industry is professionalizing at lightning speed. To stay ahead, operators must move beyond "heads in beds". In this episode, we sit down with Frank Bosi, a luxury hospitality veteran from The Ritz-Carlton and Four Seasons...
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Season 1
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Episode 19
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31:33
Short Stay Summit Operator Spotlight - Guesty
Leo and Sarah continue the Short Stay Summit mini-series with special guest Andrew Evans, Director of Customer Success (EMEA) at Guesty.With the Short Stay Summit now only weeks away, the countdown is officially on! Andrew joins us to sh...
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Season 1
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Episode 18
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31:46
Direct Bookings: The Radical Shift That Will Transform Your Business
Sarah and Leo are joined by Jessica Singer of BookingsCloud to discuss the secret to owning your demand in the STR industry with a strategy so powerful, it can cut your reliance on unpredictable OTAs and boost your margins. If you're feel...
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Season 1
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Episode 17
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40:47
Short Stay Summit Operator Spotlight - AirDNA
Leo and Sarah kick off the Short Stay Summit mini-series with special guest Martha Wilson from AirDNA. Discover how industry leaders leverage AirDNA’s advanced tools to sharpen decision-making and optimize revenue. Martha dives into...
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Season 1
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Episode 16
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30:31