The Check-In
The real scoop on the deals, the data and the drama in short-term rentals.
The Check-In
Latest Episodes
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 ...
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 w...
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 inv...
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."Jami...