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.