The Check-In

Direct Bookings in the Age of AI — with Mark Simpson, Boostly

Anyone can build a vacation rental website in an hour with AI tools like Lovable or Replit. So what's the catch? Mark Simpson — founder of Boostly and one of the world's leading voices on direct bookings — joins Leo and Sarah to explain why a pretty AI-built site is like a Lamborghini with no engine. They get into what actually drives direct bookings, why the vibe-coded revolution is a challenge to certain third-party tools, and what the rise of AI search means for how guests discover properties. Mark also shares how he thinks about AI across his own team at Boostly, and why he's more optimistic about the direct booking movement than ever — even with Airbnb still in the picture. A wide-ranging, practical conversation for any host or property manager trying to figure out where to start.

STR Investments: Why Some Soared and Others Failed

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.

The manual host tax: why you're leaving money on the table

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.

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 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.

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 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!