Short Term Rental Secrets Podcast

How do you grow a short term rental or Airbnb management business without losing the human touch that makes guests book in the first place? In this episode of the STR Secrets Podcast, Breezeway founder and CEO Jeremy Gall breaks down the real role of AI and automation in vacation rental operations, and why automating everything could quietly kill your business. Jeremy has spent 20 years building software for vacation rental operators. He founded FlipKey and grew it into one of the world's largest vacation rental platforms before TripAdvisor acquired it in 2013. Today he runs Breezeway, the AI powered property operations platform behind more than 350,000 short term rentals worldwide. So when the person who builds AI tools for a living tells you not to automate everything, it's worth hearing why. He sits down with Mike Sjogren and Mike Reilly to explain the difference between service and hospitality, how to use AI to remove administrative work without "sterilizing" your guest experience, and why the human to human connection is now the biggest competitive edge a short term rental operator has. What you'll learn in this episode: Why service is black and white but hospitality is in color, and how to deliver the kind guests remember The "sterilizing" trap operators fall into when they over automate their Airbnb business How to use AI and automation to eliminate repetitive operations work (cleaning, inspections, maintenance, scheduling) so your team can focus on five star guest experiences Build vs buy: should you build your own STR software with Claude and AI, or use an existing platform? (plus the real cost of building enterprise grade tools) The simple owner question that builds trust and improves owner retention Why small operators can out hospitality the big national brands and win How Breezeway uses embedded AI agents to automate the workflows behind five star stays. This conversation is for short term rental hosts, Airbnb property managers, vacation rental operators, and co-hosts who want to scale their portfolio while using AI the right way, to protect their edge, not erase it. Connect with Jeremy Gall at "https://www.breezeway.io/ https://www.instagram.com/breezeway.io/ https://www.linkedin.com/in/jeremiahgall" Subscribe to the STR Secrets Podcast for new episodes every Monday. #ShortTermRentals #AirbnbHost #VacationRentals #PropertyManagement #STRSecrets #Breezeway #AIforRealEstate #AirbnbAutomation #CoHosting #HospitalityTech

Most operators hit a wall around 10 or 12 listings. Steve and Kimberly Resnick pushed to 44 with just one hire, and it almost broke them. Today they run 115 listings in Ocean City, New Jersey with a team of 20+, and AirDNA just ranked HeavenlyRez the #1 property management company in the United States. In this episode they share: How a neck surgery that left Steve unable to talk pushed him out of corporate for good Why they hired twice the people they needed, on purpose The training method that turned their SOPs into a team that writes its own How they have earned more than 2,000 five star reviews Why your worst guest moments are your best shot at a five star review How they use AI to help their team instead of replacing it If you feel like you built a job instead of a business, start here. Connect with HeavenlyRez Website: heavenlyrez.com Instagram: @heavenlyrez TikTok: @heavenlyrez

STR Ai Summit Kicks Off tomorrow, grab your ticket from here: https://level.strsecrets.com/aisummit2 Dave Menapace is back — and he's got the receipts. In nine months he grew his co-hosting portfolio from 32 to 70 properties under management, and in this episode he breaks down exactly what that kind of growth actually feels like from the inside. Mike, Rilley, and Dave dig into the wins (hiring early during "peacetime," never asking your team to do something you won't do yourself, staying flexible without whiplash) and the hard lessons (the missing middle-management layer, why new doors carry lower margins, and how fast personalities pile up when you double a portfolio). Dave also shares the four fractional hires that changed his business — HR, CFO, CEO coaching, and legal — plus how he's using AI and the new Cortex dashboard to stand up a Director of Operations in two weeks instead of three and a half years. Plus: a preview of the STR Secrets AI Summit (Sept 29–30). In this episode: Referrals as the #1 growth engine after time in the industry The hidden cost of doubling a portfolio: managing personalities, not just properties Educating owners vs. defending opinions (pricing, minimum-night stays) Why the first 6 months with an owner are the highest-touch — and lowest-margin Task-completers vs. outcome-owners The CASPAR framework for scaling Fractional hires: HR, CFO, fractional CEO, legal counsel Using AI/Cortex to centralize sales, launch, ops & guest comms 🎤 About the Guest Dave Menapace is a short-term rental investor and the President of The 5-Star Co-Host, a co-hosting company specializing in managing high-end luxury vacation rentals across the country. In addition to investing and co-hosting, he is a best-selling author, contributing (with his wife) to Hospitable Host 2, and he is the host of the Hassle Free RE podcast. He and his wife own 2 short-term rentals, several long-term rentals with partners, and co-host 14 properties in New England and various other states across the country. Dave is a husband and father with a passion for public speaking and helping others achieve their goals through real estate. Connect with Dave: 🔗 Linktree: linktr.ee/menapace_realestate 📸 Instagram (personal): instagram.com/menapace_realestate 📸 Instagram (business): instagram.com/5starcohost 📧 Email: [email protected]

🚨 The AI Summit is almost sold out — grab your ticket before it's gone: 👉 https://level.strsecrets.com/aisummit2 Sep 29 & 30 | Salem, MA | $497 | Less than 20 Seats Remaining Download the Ad Spying Skill and other resources mentioned in the training from here: https://www.strsecrets.com/Autopilotresources In this AI masterclass, Ryan and Mike break down the 3 AI systems every short-term rental operator needs to grow their portfolio and maximize revenue — no VAs, no guesswork, just automation. What you'll learn: 🏠 AI Revenue Manager Connect Price Labs to Claude with one click and get a full portfolio revenue report in minutes. See your ADR, occupancy, forward bookings and year-over-year performance — all from a single prompt. Stop guessing and start acting on real data. 🎯 Automated Lead Gen & Outreach (The AI-Powered UI Method) We built an AI system that finds underperforming Airbnbs, identifies the property address via Google Maps & satellite view, skip traces the owner, and drops their name, phone & email directly into your CRM — fully automated. No VAs needed. Students are opening 8 new opportunities per week and closing $300K+ in contracts. 🕵️ AI Ad Spy for STR Operators Connect Claude to your Meta account and instantly pull every ad your competitors are running in your market. Analyze hooks, impressions and creative formats so you know exactly what's working before you spend a single dollar on ads. Results from the STR Secrets community: - Seth ran the AI revenue manager and got $14,000 in bookings the next day - Alex Cope added 40 properties in a year using the UI Method - Mike's team opened 92 new opportunities from 1,500 contacts since May - Ryan's ADR increased 20-25% in 6 months using AI revenue management

🎟️ STR AI SUMMIT — Sept 29–30 | Freedom Factory 35 spots left! Two days building real AI tools WITH us — revenue manager, listing optimizer, bookkeeping + lead gen — installed in your business before you leave. 👉 Grab tickets: strsecrets.com/aisummit2 Jamie Lane, Chief Economist and SVP of Research at AirDNA, sees more short-term rental data than almost anyone on the planet. And right now the data is telling a very clear story: the era of the small, basic Airbnb is over. In this episode Jamie sits down with Mike Sjogren and Mike Reilly to break down exactly where supply, demand, and investor dollars are flowing in 2026 — and why 6-bedroom, high-amenity, experience-driven properties are pulling away from the competition while sub-2-bedroom listings go flat or negative. Inside this episode: Why homes under 2 bedrooms are flat to negative across most of the country How 6+ bedroom "experience" properties are growing in both supply AND demand The real reason guests are choosing STRs over hotels for group and family travel What the best property managers are doing differently (hint: it's not the property) Why AirDNA's new Rentalizer AI can now tell you zoning laws before you buy Jamie's 2027 forecast and the one macro risk that keeps him up at night If you're deciding what to buy next — or wondering why your small listing isn't performing — this episode will change how you think about your portfolio. 🎙️ About Jamie Lane Jamie Lane is the Chief Economist and SVP of Research at AirDNA, the go-to source for short-term rental data and insights. With 15+ years of experience as an economist in the hospitality industry, Jamie is a leading voice of authority on the health and outlook of the STR industry. He is a regular contributor to the Wall Street Journal, New York Times, and Bloomberg, and co-hosts AirDNA's own podcast, the STR Data Lab. Before AirDNA, Jamie spent 10 years at CBRE leading research, forecasting, and data intelligence teams. He holds a BS in Economics from the University of Georgia and an MS in Business Economics from Georgia State University. 📧 [email protected] 💼 LinkedIn: https://www.linkedin.com/in/jamiehlane/ 🐦 X: https://x.com/Jamie_Lane 📸 Instagram: https://www.instagram.com/str_economist/