The Check-In

 What’s the real difference between a multi-billion dollar "SPAC" failure like Vacasa and a scaling success like Hostaway? VC partner and industry expert Eugenia Dunaeva joins Sarah and Leo to pull back the curtain on short-term rental investments. We dive into "sticky" tech stacks, the shift from overvaluation to realism, and what operators need to show investors in 2026 to get funded. 

In this episode of The Check-In, Leo and Sarah sit down with two industry heavyweights, Jamie Lane, Chief Economist at AirDNA and PC Hamana CEO of Founder of Hospitable, to break down the data behind "Single-Channel Syndrome."Jamie reveals exclusive AirDNA research showing that a surprising amount of hosts aren't using a Property Management Software (PMS), and are listed on only one platform. PC Hamana explains how automation isn't just about saving time; it's about "technological dividends" that protect your business from platform volatility.In this episode, we cover:The Data Drop: Why being on Airbnb alone could be costing you 50% of your potential revenue.The "Manual Tax": The hidden costs of refusing to automate your messaging and operations.Market Disparities: How different markets perform on each channel, with surprising insights. 

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 Sheridan to discuss why New York City is missing out on a massive tourism windfall, and why New Jersey is the one cheering from the sidelines.The trio dives into the "boring" trajectory of Airbnb’s latest updates, the risk of "corporate homogenization" in hospitality, and a fascinating look at the future of guest communication. Steve shares how he is using a conversational AI layer to handle 92% of guest inquiries via WhatsApp and voice, proving that technology can actually make hospitality feel more human, not less.And with Scale with AI and Scale UK just around the corner, Damian and Steve discuss what we will be treated to, at the events this June. 

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 now at Hostfully, to see what can be learned from the rigorous systems of the world’s leading hotel brands. Frank breaks down the five core pillars of hotel management that every STR owner should implement to increase ADR, owner and guest retention and more! 

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 share why he is feeling so energised by this year’s show and why the "one-day energy" and the buzz of a London show floor is unbeatable.Andrew provides an exclusive look at what the team has been building at Guesty, from advanced automation to the latest tools designed to help property managers scale with confidence in 2026. He explains why meeting clients face-to-face at Old Billingsgate is the highlight of his calendar. Plus, find out what Guesty has in store for the event and how their latest innovations are simplifying the day-to-day for hosts globally.

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 feeling the squeeze from algorithm tweaks, rising fees, or a flood of competition, this episode reveals how to future-proof your bookings and turn guests into loyal direct bookers. Time to stop renting demand and start owning it.

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 the power of AI-driven forecasting and explains how demand data—driven by massive events like the US World Cup—can be a game-changer for growth. Plus, hear what’s new at AirDNA and why the London Short Stay Summit is a 'must-attend' on their calendar.

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.

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.

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.

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 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.

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.

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.

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.

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 OVO Network has carved a niche in the French Alps, the importance of brand identity, and the evolving landscape of direct bookings. Whether you're in the industry or just curious, this episode offers valuable insights into the world of high-end chalet rentals.

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 explore the financial impact of commission changes and the growing trend of hosts being sidelined in their own properties. If you’re a host feeling the squeeze, this episode offers vital advice on navigating the new landscape and diversifying your bookings beyond the Airbnb algorithm.

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 to environmental concerns, we explore the factors driving this shift and what it means for the future of these beloved destinations. Join us for the stories behind the statistics as we deep-dive the evolving landscape of tourism in southern Europe.

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 the broader short-term rental industry, emphasizing the need for hosts to adapt to a more competitive landscape. The conversation also touches on Airbnb's Q3 earnings and the strategic shifts that are shaping the future of the platform.

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 challenges of remote management, the importance of local knowledge, the dynamics of online travel agencies (OTAs), and the impact of regulations on the short-term rental market. The discussion also highlights the role of technology in property management and shares insights from industry events.

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 the travel booking landscape, potentially sidelining traditional OTAs. Discover what this means for hosts, operators, and the future of travel as Google positions itself as the ultimate travel gatekeeper. Tune in to understand the shifts in the booking funnel and how an agentic AI booking funnel could give a boost to direct bookings in the short-term rental space.

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, they unravel the timeline of events, discuss the implications for operators and investors, and ponder the future of hybrid hotel models. Tune in for insights, industry analysis, and the lessons learned from one of the most significant hospitality failures in recent years.