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It’s late—around 10:30 p.m.—when Mark gets a calm call no host ever wants: “We have a little problem…the cabinets just fell off the wall.” In Part 2 of our Halloween Special, operations pro Misty Schmidt walks us through a surreal scene: upper kitchen cabinets ripping off the wall, 24 place settings shattering, and a heroic guest scooping glass with a snow shovel…in flip-flops. Misty shares: How she triaged a true “oh-no” moment with safety-first steps and on-site cleanupWhy installatio...
In this special Halloween episode of the STR Investing Podcast, Mark Lumpkin is joined by four seasoned hosts who have seen it all—ghosts, break-ins, nightmares, and even a guest covered in blood. From haunted houses in Pennsylvania to eerie first stays gone wrong, these are the stories that prove hosting isn’t for the faint of heart. In this episode: A host shares the tale of a haunted Airbnb with guests seeing a mysterious little boy.Another one recalls a California stay gone wrong when gue...
In this episode, Taylor sits down with Katie, marketing leader at Furnish Finder, to unpack how midterm rentals have evolved far beyond the travel-nurse niche. Katie shares her journey from commercial real estate to leading growth at one of the fastest-growing platforms for 30+ day stays, and why MTRs are now a must-have strategy for short-term rental investors. In this episode: The expanding MTR guest base: from medical professionals to relocations, renovations, corporate travel, and insuran...
This week, Mark sits down with Rachel Allday, co-founder of Abode Luxury Rentals, managing nearly 200 high-end properties across Park City, Jackson Hole, and Sun Valley. Rachel shares how she and her husband built their company from scratch 18 years ago—long before Airbnb existed—and what “luxury” really means in today’s short-term rental market. In this episode: How Rachel turned creativity into growth, from her first “wedding invite” mailer campaign to managing $10M+ estatesWhat defines lux...
Four years, 250 episodes, listeners in 60 countries. Annie Holcombe of the “Alex & Annie” podcast shares how a scrappy launch at VRMA turned into one of the most influential shows in short-term rentals. We cover booking hard-to-get guests, the value of cross-pollinating hotel best practices, and the power of sticking with it. Annie also announces her new consultancy, Annie & Co, and her election to the VRMA Board, with a focus on education and member value. In this episode: How a cons...
Pedro returns to unpack Sunny AI, a purpose-built assistant trained on Summer OS’s proprietary data to help investors and operators spot patterns, compare markets, and forecast performance in seconds. In this episode: Why AI fits STRs: fragmented data, shifting markets, and the need for predictive modelingWhat makes Sunny AI different: specialized (not generic) AI trained on Summer OS data to “think” like an operator and investorHow it works: compare cities and submarkets, build comp sets, be...
Andy Newman shares how a backpacker’s curiosity turned into a 140-property, multi-state operation - and why the true moat isn’t software, it’s a team with years of lived hospitality “stories” you’ll never find in a manual. We dig into hiring for heart and skill, right-sizing tech, and building resilient portfolios that survive seasonality, HOAs, and hurricanes. What you’ll learn Why tenure matters: the power of a team averaging 5+ years of on-the-ground scenariosThe tech trap: streamline tool...
Taylor sits down with Alex, co-founder of Whimstay - the OTA built to fill your unsold gap nights inside 30 days. Alex shares his journey from theater to Yelp to startup life, why Whimstay is “HotelTonight for STRs,” and how hosts can add revenue without stealing a single booking from Airbnb or Vrbo. In this episode: Incremental revenue, not cannibalization: Why Whimstay targets 0–30 days to capture mid-week, shoulder-season, and last-minute demand.Host economics: 5% host commission + travele...
This week on the STR Investing Podcast, Mark sits down with Valerie Gangas, CEO of Juniper Holiday + Home, author, meditator, and lifelong hospitality pro. Valerie shares how a childhood split between Chicago restaurants and apartment buildings shaped her “guests-first” operating system, why there’s never a checkout chore list, and how sending a real human (often with a pie!) can turn hiccups into five-star moments. She also opens up about boundaries, meditation, and why taking care of yourse...
In this episode, Taylor sits down with Zach Busekrus, growth marketer and co-founder of Journey, a game-changing loyalty platform designed for STR operators and independent boutique hotels. Zach shares how his winding path from higher ed marketing and podcasting to nomadic Airbnb living during COVID ultimately led to Journey: a mission-driven platform curating “stays with soul” and giving operators a powerful new way to increase repeat bookings, monetize guest loyalty, and gather data, all wi...
