Short Term Rental Secrets Podcast
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
Midterm Rentals Booming: Demand +30%, Supply +10%. Should You Jump In? Ex-Vrbo President Answers
Airbnb now takes 15.5% from hosts. Furnished Finder charges $199 a year. Jeff Hurst, former President of Vrbo and former COO of Expedia Group, explains why midterm rentals are growing faster than short term rentals, and how hosts can make the switch.
Jeff is the President and CEO of Furnished Finder, the largest furnished monthly rental marketplace in the U.S. He has competed with Airbnb since 2010, including as Chief Strategy Officer at HomeAway and President of Vrbo.
In this episode of the STR Secrets Podcast, Mike Sjogren and Mike Reilly ask Jeff how midterm...
Selling Your Vacation Rental Business? Start 3 Years Before You Want Out | Monarch Collective CEO
Thinking about selling your vacation rental business someday? The work starts about three years before you want out. Here's why, from a CEO whose company has made 23 acquisitions.
Big money is quietly buying up short term rental management companies.
One of Mike's students with about 40 properties had 13 emails in their inbox from groups that wanted to buy the business. The question isn't whether buyers will call. It's whether your business will be ready when they do.
In this episode, Mike Sjogren sits down with Igor Simkin, CEO of Monarch Collective, at...
Airbnb's New Rental Agreement Ban: What Hosts Can Still Do Legally (w/ Katie Johnson, STR Law)
Airbnb's new policy mostly bans rental agreements and limits how hosts collect guest information. Short-term rental attorney Katie Johnson, founder of STR Law, explains what changed, the 4 exceptions that still allow rental agreements, and how hosts can protect themselves legally.
Katie graduated from Michigan Law and has practiced law since 2011. She has hosted since 2015, and today she owns five vacation rentals and manages five more. So she has both drafted the rental agreement and dealt with the guest who ignored it. She joins Mike Sjogren and Mike Reilly to explain Airbnb's latest update in plain English.<...
From Side Gig to 8-Figure Airbnb Business… and Private Equity Is Calling
We're looking for 10 serious Airbnb operators this month who want to scale past the plateau and build a business they could actually sell one day.
If that's you, apply to the STR Secrets Mastermind here 👉
https://api.gostrmarketing.com/widget/form/VxOOgkW3BhQfHjNBpEOd
Matt and Craig (this week's guests) came up through this exact community. They're now at 100 doors with private equity knocking. The right room changes everything.
Spots are limited and we review every application.
Matt Floyd and Craig Gerulski started buy...
He Builds AI for 350,000 Airbnbs. He Says Stop Automating Everything
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...
What the #1 Airbnb Property Manager in America Does That You Don't
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:
From 32 to 70 Airbnb homes in 9 Months: What Actually Broke (and What Worked) | Dave Menapace
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 ne...
The Only AI Masterclass Airbnb Hosts Need: Leads, Revenue, and Ad Spying on Autopilot
🚨 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 Claud...
AirDNA Economist: Why 6-Bedroom Airbnbs Are Winning (Small Homes Are Dying)
🎟️ 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...
Wake Up Before It's Too Late: The STR Mistake That's Sending Hosts to Jail | Justin Ford
🎟️ STR AI SUMMIT — Sept 29–30 | Freedom Factory
40 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
Justin 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...
Inside the STR Empire Managing 700+ Vacation Homes with Michael Elefante
🎟️ STR AI SUMMIT 2.0 — Sept 29–30 | Freedom Factory
50 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
Michael 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 ou...
From 0 to 40+ Properties & a Hotel That Pays for His Life | Alex Steeg
If you want to run your STR business on autopilot by a bunch of Ai Agents then join us for a two day hands on Ai workshop on September 29-30.
Register here: level.strsecrets.com/aisummit2
We are looking for 10 STR operators to find, fund, fix and fill their first hotel, if you want to be one of them, apply here: https://boutiquehotelsecrets.com/
From one duplex to 40+ short-term rentals and a hotel that pays for his whole life — Alex Steeg proves you don't need a real estate background to build real we...
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/aisummit2
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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...
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...
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...
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...
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.
<...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.<...
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.
<...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.
<...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...
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 year...
Working 24/7 But Still Stuck? This is why Your STR Business Isn't Growing
"🔥 LAST CHANCE — STR AI SUMMIT, June 23-24 | Freedom Factory, Beverly, MA
Only 10 seats left
. This is where direct bookings, AI agents, and the next decade of STR get built — live, with the operators leading the charge.
👉 strsecrets.com/aisummit
Most STR operators don't have an information problem.
They have an identity problem.
In this solo episode, mindset coach and STR Secrets co-host Emanuele Pani
breaks down the framework he's been using inside the weekly STR Secrets mindset
calls — an...
Direct Bookings, AI Agents & Why Airbnb Fees Are Going to 20% | Mark Simpson Returns
🔥 LAST CHANCE — STR AI SUMMIT, June 23-24 | Freedom Factory, Beverly, MA
Only 20 seats left. Use code "PODCAST" for a flat $1000 discount:
👉 strsecrets.com/aisummit
The coupon expires Monday
This is where direct bookings, AI agents, and the next decade of STR get built — live, with the operators leading the charge.
Yorkshire, UK — Mark Simpson spent $50,000 on human appointment setters last year. They did almost nothing.
Then he built one AI agent named Icarus. In 7 days, it closed a $5,000 deal. Cost? Less than $20.
Two months...
The AI Comp Tool That's Getting STR Managers 7 Sales Calls a Week
Ryan will be showing how to make this and a custom revenue management tool live at the Ai Summit. Grab your spot at the AI Summit: strsecrets.com/aisummit at just $497. Use the coupon : "PODCAST"
Every homeowner conversation starts the same way.
They want to know what their property can earn.
And if you can't answer that question fast, professionally, and with data behind it —
someone else will.
In this week's training, Mike sits down with STR Secrets coach Ryan Lefebvre to...
Why Your STR Business Stopped Growing (And It's Not the Market)
🔥 Get $500 off at STR AI SUMMIT — June 23-24 | Freedom Factory, Beverly, MA
Use code "MEMORIAL500" while checking out at strsecrets.com/aisummit
You're doing the work. You're managing the properties. You're showing up every day.
So why does it feel like you're spinning your wheels?
In this solo show, Chris Petzy and Emanuele Pani get raw about the real reason STR
operators stall out — and it has nothing to do with the market, your pricing strategy,
or your occupancy rate.
<...She Built an AI Agent That Creates 10 Carousels From One Airbnb Link | Dr. Rachel Gainsbrugh
Get Carrie the AI Carousel Sniper Agent: https://level.strsecrets.com/drrachel
🔥 STR AI SUMMIT — June 23-24 | Freedom Factory, Beverly, MA
Dr. Rachel is flying in to spend 2 full hours building this exact system with you live.
You won't just learn it. You'll leave with it installed. Only 70 seats left.
👉 strsecrets.com/aisummit
Most STR operators know they need to post more. They just don't have the time, the team, or the system to do it.
Dr. Rachel Gainsbrugh does. And in Portfolio Clinic Episode 8, she pulls back the...
$1B STR Company CEO Tells You Exactly How AI Will Eat Your Business (Or Make You Rich) | Marcus Räder, Hostaway
🔥 STR AI Summit — June 23-24 | Freedom Factory, Beverly, MA
Only 100 seats. Built for operators who are serious about what comes next.
👉 strsecrets.com/aisummit
If you're managing 5, 10, or 50+ properties and wondering whether AI is a tool or a threat — Marcus Räder has the answer. And it's not what most people are saying.
Marcus is the co-founder and CEO of Hostaway — the first vacation rental software company to reach unicorn status and the recipient of the largest funding round in vacation rental history: $365 million led by General Atlantic.
He's been i...
The Real Truth About AI for STR Operators — What Works, What Doesn't, and What It Actually Costs
Join use at the STR AI Summit — June 23-24 at the Freedom Factory in Beverly, MA. 100 seats only strsecrets.com/aisummit
Mike Sjogren spent over $5,000 in API credits in two months learning AI the hard way. And he wants to make sure you don't have to.
In this Portfolio Clinic training, Mike breaks down the top 10 AI mistakes that cost him real money — from not understanding context windows to memory file bloat to giving an agent 15 tasks at once and wondering why nothing got done. He then walks through exactly how STR operators shou...
Buying Facilities for $40K a Door: Why Senior Housing is the Next Major Real Estate Wave
🎟️ Join us at the STR AI Summit — June 23-24 at the Freedom Factory in Beverly, MA.
Only 100 seats. Early bird: $1,497.
strsecrets.com/aisummit
Tying your identity to your door count is the fastest way to burn out—or worse. In 2008, Rod Khleif lost $50 million. He calls it an expensive "seminar."
In this episode, E sits down with Rod to discuss how he rebuilt his massive real estate portfolio by fundamentally changing his peer group and his mindset.
Today, Rod's students own over 260,000 units, and he has fed more than 160,000 children...
The Exit Strategy Most STR Operators Don't Have — And Why It's Costing Them Millions
Join us at The STR AI Summit is June 23-24 at the Freedom Factory in Beverly, MA.
100 seats only. Grab your ticket: https://www.strsecrets.com/aisummit
Most STR operators have built a great lifestyle business. But here's the hard truth: only 1 in 10 businesses will ever successfully sell. The rest close and walk away with nothing.
In this Portfolio Clinic training, Mike Sjogren breaks down exactly how STR management companies are valued — and what operators need to start doing right now to build a business with a real exit strategy.
He wa...
The Stay-at-Home Mom Who Built 4 STRs, 11 Co-Hosted Properties, and a Coaching Business — While Raising 3 Kids
She thought it had to be one or the other.
Career or kids. No middle ground.
Then her daughter was diagnosed with leukemia at three years old.
And everything changed.
Jane Ng left corporate America to care for her daughter full time. Her daughter survived — but was left with a brain injury that means she will never be fully independent. Jane will care for her for the rest of her life.
So going back to a W2 was never an option.
Instead she found real estate. Then sh...
The 4-Year Warning: Why AI is About to Replace Average Operators | David VanWert
📲 Connect with STR Secrets:
Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book
STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets
Apply to work with us: https://strsecrets.com/apply
STR Secrets Podcast: https://strsecrets.com/podcast
Most luxury STR owners write that electric bill every month without ever knowing what's causing it. David VanWert did the same thing — until he built a platform to fix it.
In this episode, E and Chris sit down with David VanWert, found...
The Split Fee Is Not Back: What Airbnb's 15.5% Host-Only Fee Actually Means for Your Payout
As of April 15th, Airbnb moved every host to a 15.5% host-only fee.
If you haven't updated your pricing yet — your next booking will pay you less than you expect.
Btw you can grab the spreadsheet from here : https://www.strsecrets.com/airbnbfee
Also, if you want to talk to us directly: http://strsecrets.com/implement
In this training Mike covers:
- What the Airbnb fee change actually means: 15.5% host-only fee applies to nightly rate, cleaning fee, resort fee, pet fee — everything
- Why the split fee showing back...
What the #1 Restaurant in the World Taught Me About Running a Better STR Business
Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book
STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets
E just got back from the Unreasonable Hospitality Summit in Nashville — and this solo episode is his full recap.
Will Guidara wrote Unreasonable Hospitality during COVID. He took Eleven Madison Park from a nice restaurant to the #1 restaurant in the world — the only restaurant to ever go from one Michelin star to three in a single year.
His philosophy: service is what you do for people. Hospitality is how you...
The STR Tax Loophole That Could Save Your Homeowners $100,000 — And Win You More Clients
If you want to increase your revenue, automate your day to day operations and spend more time with your kids: http://strsecrets.com/implement
If you want to join our weekly free training:
https://www.facebook.com/groups/STRentalsecrets
Most property managers and co-hosts pitch homeowners on management fees.
Mike Reilly pitches them on $100,000 in tax savings. And it closes more deals than anything else.
In this Portfolio Clinic training, Mike breaks down the STR tax loophole — why it works, who qualifies, and ex...
From Tragedy to 65 Units: How Cara and Mark Truckey Built a Life and Business on Their Own Terms
In 2016, Cara and Mark Truckey lost their 14-month-old son. He never woke up at daycare.
Most couples don't survive a loss like that. Instead, it became the moment that changed everything.
In this episode, E and Chris sit down with Cara and Mark Truckey — two STR Secrets boardroom alumni who have built a real estate portfolio of 65+ units across Wisconsin and Florida while raising three kids and running multiple businesses.
This is one of the most honest and human conversations we have had on this show.
In this episode Cara and Ma...
Airbnb Makes $1 Billion From Your Repeat Guests. Here's How to Take That Back | Portfolio Clinic #3
If you want to increase your revenue, automate your day to day operations and spend more time with your kids: http://strsecrets.com/apply
If you want to join our weekly free training:
https://www.facebook.com/groups/STRentalsecrets
Every time a past guest books your property again through Airbnb — Airbnb takes the fee. Again. Repeat guests generate over $1 billion in revenue for Airbnb annually. And most STR operators are doing nothing to capture that themselves.
In this Portfolio Clinic session, Mike Reilly breaks down the direct bo...
Your STR Could Be Banned Tomorrow and Here's What You're Not Doing About It | ft. Julie Marks
If you want to increase your revenue, automate your day to day operations and spend more time with your kids: http://strsecrets.com/apply
If you want to join our weekly free training:
https://www.facebook.com/groups/STRentalsecrets
Most STR operators don't think about regulation until it's already too late.
Julie pulls back the curtain on what’s really happening in short-term rental regulation and why hosts can’t afford to stay invisible. From local politics to nationwide advocacy, this episode is a wake-up call for operators who think regulation is s...
Every Objection That's Costing You Clients — Handled Live on Stage at Our Acquisitions Event
If you want to increase your revenue, automate your day to day operations and spend more time with your kids: http://strsecrets.com/apply
If you want to join our weekly free training:
https://www.facebook.com/groups/STRentalsecrets
This one is different.
At our last STR acquisitions event at the Freedom Factory in Beverly, MA, we did something we'd never done before.
We filled a hat with real homeowner objections — things operators hear every day — and had four coaches handle them live on stage in f...
