The Check-In

The Secret to 100% Direct Bookings? Build a Brand Worth Talking About

What does it actually take to run a vacation rental business at 100% direct bookings — no Airbnb, no OTAs, no exceptions? Francesca and Annie from Unique Homestays join Leo at Scale UK to answer exactly that. Unique Homestays is one of the UK's most quietly exceptional luxury vacation rental brands — a portfolio of around 190 handpicked properties, a sole founder still at the helm after a quarter century, and a waiting list of guests who come back year after year without ever needing a platform to find them. In this conversation they get into what luxury really means (hint: it's often a whitewashed beach shack, not a chandelier), why curation beats scale every time, how the luxury guest is booking further in advance while the rest of the market is dealing with shortening book windows, and why AI is something a brand like theirs should welcome rather than fear. If you've ever wondered whether building a truly independent, brand-led STR business is still possible — this episode is your answer.

The Long Game — What 54 Years in STR Teaches You About Airbnb's Big Moves

Airbnb just announced hotels, car rentals, grocery delivery, airport pickups and a clear signal that flights are coming. But what does all of that look like through the eyes of someone who's been running a family STR business since that's been operating since 1972? Tom Goodwin, CEO of Mountain Laurel Chalets in Gatlinburg, Tennessee, joins Leo and Sarah to react to Airbnb's 2026 summer release — and to offer a perspective most operators can't. MLC is in its 54th year, runs 75-80% direct bookings, and only joined Airbnb two and a half years ago. Tom talks about why repeat guests are the real business model, why Airbnb's expansion into ancillary services should worry operators who've built their revenue around add-ons, and why the operators who came in hot in 2021 are now calling him every week with a problem. He also makes a case that the pendulum is swinging back — that travellers are tired of the plastic fantastic and craving something real. A grounded, honest conversation about what the long game actually looks like in short-term rentals.

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.