Short Term Rental Secrets Podcast

Hosted by MICHAEL SJOGREN

Business Education

Website RSS feed

Episodes

383

Latest episode

Aug 2026

Language

About the show

The Short Term Rental Secrets Podcast is dedicated to providing actionable content to help new and seasoned real estate investors launch, automate and scale their Airbnb business and fast track their journey to financial freedom. You can enjoy the podcast and other free resources at www.STRsecrets.com

Listen to episodes

60 recent

August 17, 202637 min

The AI Tools Actually Making STR Operators Money in 2026 | Ryan Lefebvre

🎟️ STR AI SUMMIT — Sept 29–30 | Freedom Factory 100 spots only (sold out in 4 weeks last time). 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/aisummit ━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Everyone is telling you to build AI tools. Ryan Lefebvre, the AI expert behind the tools at STR Secrets, is telling you to stop. In this episode, Ryan sits down with Mike Sjogren and Mike Reilly to explain why building your own AI is the new shiny object, and why it's quietly killing operators who should be focused on their business instead. Ryan is a former fraud analyst turned pilot turned STR operator who now builds AI systems for management companies. He shares which AI wins actually move the needle, and which ones are a total waste of your time. From cleaning up messy books, to a revenue manager that found thousands in missed bookings, to the listing fixes most owners never catch, this is the real playbook for using AI without falling down the rabbit hole. ⏱️ CHAPTERS 0:00 Intro 1:02 From ditching school to fraud investigator to pilot 3:51 The one question: is AI making you money or costing you? 8:54 Why everyone's books are a disaster (and how Claude fixes it) 11:27 Building a revenue manager agent that finds hidden bookings 14:37 The listing optimizer + ALE framework 21:18 How to motivate your team to think Ai first 27:41 Treat AI like an employee — SOPs are the fuel 31:11 STR AI Summit: what you'll build Sept 29–30 ━━━━━━━━━━━━━━━━━━━━━━━━━━━━ 🎟️ Ready to build? strsecrets.com/aisummit — Sept 29–30

August 10, 202648 min

The Man Who Sold Off Vacasa: Sell Your Airbnb Business NOW — Before The Window Closes! | Jacobie Olin

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. TIMESTAMPS 00:00 Meet the man who brokers STR company sales 00:25 What C2G does and the size of deals they run 02:25 Inside the Vacasa and Casago deal 09:10 Why big money is moving into a fragmented industry 10:32 The state of the market and why the next few years favor sellers 13:30 How companies are valued by size (the multiple ladder) 16:00 Why smaller deals pay you less cash up front 17:56 Turning a lifestyle business into a sellable asset 21:00 The magic number that opens the door to real buyers 24:35 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 valuation 41:12 The fee trick that quietly raises your take rate 42:45 Where the whole industry is headed next Want the KPI scorecard from this episode? DM @strsecrets on Instagram. Learn more about C2G Advisors: https://c2gadvisors.com Connect with Jacobie: jacobie@c2gadvisors.com Subscribe for new episodes every Monday. #ShortTermRentals #PropertyManagement #AirbnbHost #VacationRentals #STRSecrets #RealEstateInvesting #BusinessExit #MergersAndAcquisitions

August 3, 202638 min

How he left the media business to Build a 53-Unit Rental Business in One Town | Jason Muth

Everyone in short-term rentals is chasing the next tool. The next software. The next tech company. The next shiny object. Jason Muth did the opposite. And it built him a 53-unit business in about two years. In this episode, Jason joins the show to break down how he grew Prideaway Stays from his first client in April 2024 to 53 properties under management, with zero acquisitions and 100 percent organic growth. No buying other companies. No chasing every new tactic. Just one market, one avatar, and a relentless focus most operators are too distracted to hold. In this episode: → Why Jason picked one town, went all in, and refused to look at a single other market → The organic growth engine behind 53 units, from handwritten direct mail to referrals from cleaners and owners → How he walked away from a career at some of the biggest media companies in the country and became the go-to short-term rental expert in his market → The delegation moment on a cruise that finally forced him to stop doing everything himself → How he educates owners with simple monthly videos and real data, and why that consistency builds trust that closes deals → Why the market has shifted, how property values doubled while revenue did not, and what that means for owners today → His number one secret to success: make big decisions fast, and stop chasing shiny objects If you feel overwhelmed by every new tool and tactic in this space, this episode is the reset you need. About Jason: Jason Muth left W-2 life in 2022, after his real estate side hustle became more profitable than his corporate career at companies like Comcast, NBCUniversal, and iHeartMedia. He is the founder of Prideaway Stays, a boutique, gay-owned, tech-driven co-hosting business in Provincetown, MA, and the owner of Straightforward Short-Term Rentals in Massachusetts and New Hampshire. He also hosts the SmartStay Show. Connect with Jason: Instagram: @prideawaystays Podcast: SmartStay Show, on YouTube, Spotify, and Apple Podcasts Free 6-step course to start your day right: level.strsecrets.com/pc-book

July 27, 202632 min

How He Went From 18 to 140 Airbnb Units by Buying a 40 Year Old Company

Most operators grow their rental business one contract at a time. Cameron Masters skipped the line and bought his way from 18 units to over 140 in a single deal. In this episode, we sat down with Cam to walk through the whole acquisition, start to finish. He bought a 40 year old management company, one started by a founder of Vrbo, and he shares the exact moves that got it done. Inside this episode: How Cam went from 18 units to 140 plus by buying one company Why he skipped the bank and used seller financing plus a friends and family raise How he and his partner put in just 30 percent and got the seller to carry the rest The 10,000 dollar move that can save you from a 1 million dollar mistake The 35,000 dollar cost he forgot to check, and how it bit him after closing The room full of bigger operators that made him stop thinking small If you have ever felt like real growth is out of reach, this one will change how you think about what is possible. Want to be in the room with operators doing deals like this? Check out the STR Secrets Mastermind: strsecrets.com/apply Connect with Cameron Masters on Instagram: @cameron.masters_ New episodes every Monday.

July 20, 202619 min

The COHOST Funnel: How to Sign New Homeowners Before Fall Renewals

Want to scale your property management or co-hosting business past 10, 20, 50 listings? Book a call here: https://strsecrets.com/apply Connect with Mike Reilly : https://www.instagram.com/mikereillync/ Most operators think busy season is the worst time to look for new properties. Mike Reilly just signed 7 new contracts that prove them wrong. Last quarter his team at NC Stays reached out to 1,000 homeowners. They opened 68 real conversations. They signed 7 new properties, and 19 more deals are still on the table. And all of it started in the middle of peak season. Why? Because of one thing most operators never check: the 90 day notice window. Most management contracts renew in the fall. If a homeowner wants to leave their property manager, they have to say so 90 days before the contract renews. So if you wait until September to start talking to owners, they're already stuck for another year. In this 18 minute training, Mike walks through his COHOST funnel step by step: C: Create awareness. A simple website, social posts, and a list of homes you want. O: Open the conversation. Send a free 5 minute video showing the owner what they're missing. Don't ask for a meeting. H: Hold the discovery call. This is where deals are really won, and where you filter out bad-fit owners. O: Offer your solution. S: Sign the contract. Including the $2,500 upgrade rule Mike puts in every contract. T: Take over and onboard. This pairs with last week's onboarding episode. Plus the story of a beach house owner losing $30,000 to $40,000 a year because his best photo was buried at spot #68 in his listing. And why it takes about 4.5 calls before an owner signs. If you have no new leads right now, this episode shows you why. Save it. Want the owner contact lists, the CRM, and a community of operators growing past 50 listings? Check out the STR Secrets Mastermind: [LINK] New episodes every Monday.

July 13, 202622 min

How to Onboard Airbnb Properties So Owners Never Leave (Full System)

Want to scale your property management or co-hosting business past 10, 20, 50 listings? Book a call here: https://strsecrets.com/apply Connect with Mike Reilly : https://www.instagram.com/mikereillync/ How do you onboard 7 vacation rental properties in one month without burning out your team? Mike Reilly breaks down the exact 6 stage onboarding system NC Stays uses for every new property, from the first homeowner call to the post launch celebration. Homeowner trust in property managers is at an all time low. Nearly every owner has been burned before. The managers who onboard properties with a real system are locking in 5 to 10 year relationships and standing out in a market flooded with new co-hosts. In this training you'll learn the full checklist: Why the first 30 days with a homeowner decides the next 10 years The 6 stages of onboarding: Handoff, On-Site Setup, Photography, Listing & Software Setup, Final Touches, and Post Launch How Mike's team uses Meta glasses to capture every inch of a home and turn it into checklists automatically The QR code trick that eliminates guest questions about the grill, hot tub, sauna, and game room The exact roles to hire: project manager, contractor help, listing team, and data quality How one Pinehurst property pulled $30,000 in bookings from mood boards alone, before it was even ready The review stay strategy that gets Airbnb pushing your listing to page one in week one TIMESTAMPS 00:00 Trailer 00:37 Welcome back + what's coming for the podcast 02:02 Onboarding 7 properties in one month (all 4,000+ sq ft) 03:59 The trust crisis and why onboarding is your biggest advantage 05:00 The system and the 6 roles you need on your team 07:58 The 6 stages of onboarding explained 08:01 Stage 1: The Handoff (welcome email, onboarding form, group text) 09:55 Stage 2: On-Site Setup with Meta glasses 11:12 QR codes, inventory counts, and the house manual 14:30 Stage 3: Photography (lifestyle shots, staging, shot lists) 15:35 Stage 4: Listing & Software Setup (custom GPT listings, PriceLabs) 16:55 $30,000 in bookings from mood boards before launch 17:36 Stage 5: Final Touches (data quality, review stays, financials) 19:07 Stage 6: Post Launch (social posts, email list, owner shareables) 20:02 Why you can't scale without this process 20:41 Inside the STR Secrets Mastermind

July 6, 202632 min

Why the Next Few Years Are the Best Time to Build and Sell Your STR Business

Something big is happening in short-term rentals, and most operators have no idea. In this episode, Mike Sjogren returns to the show with Mike Reilly. And they open with a trend that changes everything. In 2022, most short-term rentals in the US were run by hosts with fewer than 20 units. By 2025, that share had dropped hard. The reason is not that hosts quit. It is that private equity quietly started buying up management companies, because the margins are good and the industry is wide open. Mike breaks down what that means for you, and reveals the project STR Secrets has spent 16 months building to help members cash in on it. In this episode: → The data behind the great short-term rental consolidation, and why the big money is moving in now → Freedom Collective: the new vehicle built to help operators sell their management company for a 6 to 8X exit instead of a 3 to 5X → How 22 members generated over $3 million in new management commissions in about 7 weeks, including one who acquired a company and added 122 doors in a single quarter → The full AI Summit recap → Why the most important hire of the next few years is an AI mplementation specialist, and why the CEO's job is to cast the vision, not tinker in the tools until 3am → Mike's own Q2 numbers from the new AI-powered CRM: 1,000 leads, 68 opportunities, 7 new clients, and $211,000 in new commissions, while taking only 10 percent of the sales calls himself Whether you have your first property or your fiftieth, this episode will change how you think about where this industry is headed. Ready to scale and exit the right way? Apply to work with us: strsecrets.com/apply

June 29, 202618 min

E's Last Episode: 300 Shows, 6 Years, 5 Lessons

Six years ago, E said yes to something he had no idea would change his life. 300 episodes later, this is his last one. In this final solo show, recorded from his grandparents' house in Sardinia, Emanuele Pani answers the same question this podcast has asked every guest for six years. What is your number one secret to success? Only this time, he answers it for himself. E shares the 5 lessons that changed his life more than anything else. The lessons that took him from chasing more information, more courses, and more outside validation, to the most peace, health, and happiness he has ever felt. In this episode: → Why your identity, not your strategy, decides how far you go → The difference between goals and standards, and why standards are the ones that actually shape your future → How the story you tell about yourself becomes the life you live → Why every level of growth costs you the person you used to be → The inside-out truth about success that no system or strategy can replace This is not a goodbye. It is a thank you to a community that has spent six years in E's ears. In your cars. In your kitchens. On your morning walks. And it is a torch being passed. Thank you for everything, E. Free 6-step course to start your day right: level.strsecrets.com/pc-book Join the community: STR Secrets Facebook Group You can follow E's next chapter on his new show, CEO Mindset, available now on Spotify and Apple Podcasts.

June 22, 202641 min

From the ICU to 70 Rentals: How a Full-Time Nurse Built His Way Out with Jeremy Rosen

He was working 80 hours every two weeks in a hospital ICU. Open heart surgery patients. Life or death. No room for error. And in the gaps between shifts, sometimes still in his scrubs, he was quietly building a short-term rental business that would set him free. In this episode, E sits down with Jeremy Rosen for one of the most honest W2-escape stories this show has ever told. Jeremy joined STR Secrets with 4 properties and a full-time nursing job he loved but knew he had to leave. He went from 4 to 8 to 12 to 20 properties, all while clocking 12-hour shifts at the VA. Then he merged his own company into Five Star Vacation Home Rentals, where he now owns the San Antonio division, part of a portfolio of 70 properties across Central Texas. And he finally walked away from nursing for good. Today, based in San Antonio, Texas, Jeremy focuses on revenue optimization, guest experience, property operations, and scaling high performing vacation rental portfolios. In this episode: → The exact mindset shift that took Jeremy from sick patients to happy guests, and the nurse's instinct that makes him a better host than most operators will ever be → How he used his days off, while everyone else scrolled, to prospect, sell, and grow → The "who not how" decision that broke him out of doing everything himself, and the one hire that changed his entire business → Why he refused to build in secret, and how speaking his goals out loud actually made them happen → The honest truth about quitting your W2 that almost nobody talks about, including the strange struggle of suddenly owning all of your own time → Why "everything is figureoutable" is the only belief you need to finally make the leap If you have a good job you're scared to leave, this is the episode you need to hear. Connect with Jeremy: Instagram and Facebook: @fivestarvhr Email: jeremy@fivestarvacationhomerentals.com Website: fivestarvhr.com Free 6-step course to start your day right: level.strsecrets.com/pc-book Join the community: STR Secrets Facebook Group

June 15, 202655 min

He Was Running 6 Businesses, Managing 30 Properties, and Losing His Family | Dave Menapce

His wife said something to him that he'll never forget. "I would let every business burn to the ground if it meant that when it's nighttime and on weekends, we could spend it as a family." Dave Menapace didn't argue. Didn't defend himself. He sat with it. And then he changed everything. In this episode, E sits down with STR Secrets coach and Five Star Co-Host founder Dave Menapace — on his birthday — for a raw, unfiltered look at four years of building, burning down, and rebuilding a short-term rental management company the right way. Dave left corporate healthcare in April 2022 with two STRs and a vision. Four years later, he's managing 58 properties. He signed number 58 this morning. But the path there? It looked nothing like what he planned. In this episode: → The "seven streams vs. seven jobs" mistake that keeps most operators broke and burned out — and how Dave finally broke the cycle → How he started Five Star Co-Host over from scratch after realizing he'd built it wrong the first time → The $100K IRA withdrawal that gave him the team he needed to grow → Why he went from 30 properties to 58 in just 5 months — and the three obsessions that made it possible → The $80,000 trust account crisis that hit in September 2025 — and why his response to it doubled the business → What it actually takes to build a management company worth $100M (and why Dave believes it's just a choice) This is not a highlight reel. It's the version of the story most people are too scared to tell. Want to connect with Dave? Find him on Instagram: @dave_menapace Join the community: STR Secrets Facebook Group Free 6-step course: level.strsecrets.com/pc-book Timestamps: 00:00 - "Seven streams of income is not seven jobs" 08:07 - Leaving corporate, WealthCon, and the birth of Five Star Co-Host 15:48 - The Miami pool moment Kim told E: "my husband is doing a million things" 32:21 - The most important thing Kim ever said to Dave 35:45 - The three obsessions that unlocked 30 to 58 properties in 5 months 48:17 - The $80,000 crisis and what focus does under pressure