Short Term Rental Secrets Podcast

Jeremy Gall, Breezeway founder and CEO, previously built FlipKey before its acquisition by TripAdvisor. He explores why hospitality goes beyond basic service, how AI can streamline turnovers, maintenance, scheduling, and inspections, and the danger of over-automating the guest experience. He also discusses empowering field teams, retaining owners through consistency, and when to buy software instead of building it.

Kimberly and Steve Resnick, founders of HeavenlyRez, grew a beach rental operation into America’s top-ranked property management company. They reveal how hiring ahead, hospitality-first training, and employee-created SOPs fueled growth. Hear how thoughtful problem-solving earned 2,000+ five-star reviews, why operations moved in-house, and how AI supports teams without replacing personal service.

Dave Menapace, short-term rental investor and president of The 5-Star Co-Host, shares what happened when his portfolio jumped from 32 to 70 homes in nine months. They explore referral-driven growth, hiring early, owner education, shrinking margins on new properties, and the missing middle-management layer. Dave also discusses fractional executives, leadership challenges, and using AI and Cortex to centralize operations.

Discover three powerful AI systems for short-term rental operators: automated lead generation that finds and contacts owners, one-prompt revenue reporting through Price Labs and Claude, and competitive Meta ad spying. The discussion also explores building reliable AI workflows, testing content, improving pricing, and freeing teams to focus on exceptional hospitality.

🎟️ STR AI SUMMIT — Sept 29–30 | Freedom Factory35 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/aisummit2Jamie 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 countryHow 6+ bedroom "experience" properties are growing in both supply AND demandThe real reason guests are choosing STRs over hotels for group and family travelWhat 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 buyJamie's 2027 forecast and the one macro risk that keeps him up at nightIf 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/

🎟️ STR AI SUMMIT — Sept 29–30 | Freedom Factory40 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/aisummit2Justin is the most trusted safety expert in the short term rental world. He served in the Coast Guard, spent 15 years as a firefighter, and once ran one of the largest vacation rental companies in the country before a safety incident nearly cost him everything. Now he helps operators protect their guests, their businesses, and themselves. In this episode he sits down with Mike Sjogren and Mike Reilly to walk through the dangers hiding in almost every rental, and the simple fixes that keep you out of court.Inside this episode:Why bunk beds send nearly 70,000 people to the ER every year, and the federal law most hosts don't know they're breakingThe lithium battery threat that's quietly burning down propertiesWhy pools, dryers, and grills are among the top causes of serious injuries and firesThe insurance trap that leaves hosts uncovered right when they need it mostThe simple documentation habit that turns a lawsuit into a defensible accidentJustin's roughly $400 safety setup that protects an entire propertyThis is the episode that makes you stop, look around your rental, and fix the things you never knew were dangerous. It's not about fear. It's about protecting the business you worked so hard to build.Justin is also sharing his full safety checklist with our listeners. Details on how to grab it are in the episode.

🎟️ STR AI SUMMIT 2.0 — Sept 29–30 | Freedom Factory50 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/aisummit2Michael Elefante didn't set out to build an empire. There was no whiteboard and no master plan, just one short term rental he bought in 2019 and a willingness to jump before he felt ready.Before real estate, Michael went from working at Dunkin' Donuts after college to climbing the corporate ladder at Google and in outside sales. The income was high, but the travel and the hours weren't the life he wanted for his future family. So he bought his first rental, hit financial freedom fast, and even spent a year traveling the country in a camper van with his wife Jill, running the business remotely the whole time.Today he's the President and Co-Founder of The RISE Collective, a vertically integrated ecosystem serving the short term rental industry. It spans BNB Investor Academy, BNB Turnkey & Construction, Home Team Luxury Rentals (a nationwide property management firm), Summerlet Designs, and in-house lending, CPA, legal, and referral divisions. A best-selling author and investor who has helped thousands of people optimize high performing properties, Michael scaled not by chasing shiny objects but by pulling referral services in-house, building a multi-million-dollar portfolio now aimed at a nine-figure exit.In this episode, Michael sits down with Mike Sjogren and Mike Reilly to break down how it actually happened, and the mindset that made it possible.Inside this episode:The "do it before you're ready" philosophy, and why confidence comes after the jump, not beforeThe "who, not how" mentality: hiring strong operators so you can work limited hours and take Fridays offHow to build experience-driven properties that price out your competitionThe simple migration-pattern strategy Michael uses to pick winning marketsWhy giving away his exact playbook has only made him more successfulHow vertical integration turned one business into an entire ecosystem, almost by accidentWhy he's moving into boutique hotels now, and who it's really forSaying no: how his goals shifted from cash flow to building real enterprise valueWhether you're buying your first rental or scaling a portfolio, this is a masterclass in taking action, staying in your lane, and building a business that supports a family-first life instead of one that dictates it.Connect with Michael: @melefante6 on Instagram, or learn more at rise-collective.com/about-us/michael-elefantePodcast Chapters:Chapters00:00:00 Intro: Traveling the World & Experience-Driven Rentals00:05:37 How Michael Picks Winning Markets (Migration Strategy)00:12:43 Building the RISE Collective & Vertical Integration00:19:18 The Mindset Shift: Buy the Ticket00:22:32 Scaling Home Team + Moving Into Boutique Hotels00:31:00 Long-Term Vision & His #1 Secret to Success

Alex Steeg, co-founder of Shore Way Management who scaled from one duplex to 40+ short-term rentals and owns a 10-room hotel. He explains how they found and flipped an underperforming inn, why hotels differ from short-term rentals, and how a small, smart team and Google referrals drove growth. Also covers hiring mindset, using rental cash flow to buy hotels, and running a hotel in minimal weekly time.

Ryan Lefebvre, former fraud analyst turned pilot and STR operator who now builds AI systems for management companies. He warns against chasing shiny AI and highlights practical wins like AI bookkeeping with Claude, a revenue manager that uncovers missed bookings, and a listing optimizer using the ALE framework. Short, tactical takes on when AI helps and when it distracts.

What is your short term rental management company actually worth? Jacobie Olin sells these companies for a living, around 20 deals a year worth close to 200 million dollars, and in this episode he breaks down exactly how buyers value your business, what multiples they pay, and why most operators are sitting on a lifestyle business instead of a sellable asset.Jacobie is the founder of C2G Advisors and brokered the landmark Vacasa and Casago deal. He walks through EBITDA, multiples, take rate, churn, and the real steps to turn a small management business into something worth millions. If you have ever thought about selling your rental business one day, this is the playbook for what to build toward now.TIMESTAMPS00:00 Meet the man who brokers STR company sales00:25 What C2G does and the size of deals they run02:25 Inside the Vacasa and Casago deal09:10 Why big money is moving into a fragmented industry10:32 The state of the market and why the next few years favor sellers13:30 How companies are valued by size (the multiple ladder)16:00 Why smaller deals pay you less cash up front17:56 Turning a lifestyle business into a sellable asset21:00 The magic number that opens the door to real buyers24:35 Can you sell on co-host contracts instead of full management?26:35 Mike Reilly asks: how do I acquire another company?32:45 The KPIs that actually drive your valuation41:12 The fee trick that quietly raises your take rate42:45 Where the whole industry is headed nextWant the KPI scorecard from this episode? DM @strsecrets on Instagram.Learn more about C2G Advisors: https://c2gadvisors.comConnect with Jacobie: [email protected] for new episodes every Monday.#ShortTermRentals #PropertyManagement #AirbnbHost #VacationRentals #STRSecrets #RealEstateInvesting #BusinessExit #MergersAndAcquisitions