Short Term Rental Secrets Podcast

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 buying vacation rentals in 2018 to build side income while working their W-2 jobs. In 2020 they launched Stay Classy Homes to manage their own properties and a few arbitrage units in San Diego, and they ran it as a side gig for 3 years.

Then a trip to STR Wealth in Nashville changed everything. They quit their jobs in 2023, went two years without paying themselves, and have since grown Stay Classy into an 8-figure business with 100+ properties under management across San Diego, Kauai, Nashville and Phoenix.

Now private equity groups are calling.

Fresh off VRMA, Matt and Craig sit down with Mike Sjogren to break down exactly how they rebuilt the business at every stage of growth, and how they're thinking about a potential exit.

In this episode:

• Hiring breakpoints: VAs at 20–40 properties, local staff at 60–80, and leadership after that
• Their full team structure at 100+ properties
• How many properties each property manager should oversee (and how to bundle them)
• The $3,000/month VA fear that almost kept them stuck
• How they're vetting private equity offers: fit, incentives, tuck-ins and rolling equity
• "Everybody exits": the 5 D's and why you should build to sell even if you never will
• The real risks in STR: economic swings, regulation, and the OTAs owning your guest
• Why your team problem is usually a leadership problem
• How to recruit executives by selling your vision, not just the pay
  

Mentioned: VRMA, Steve Schwab (Casago), The Happiness Advantage, Igor Simkin (Monarch), Jason Cisneros, Coach Michael Burt, Breezeway, Guesty

🤝 Connect with Stay Classy Homes: 📸 Instagram: @stayclassyairbnbguys 💼 Partner with Stay Classy: [email protected] 📧 Reach Matt directly: [email protected]

⭐ If this episode helped, leave a rating on Apple Podcasts. It's the #1 way new hosts find the show. 📬

New episodes every Monday.

#ShortTermRentals #AirbnbHost #VacationRentals #PropertyManagement #STRSecrets #PrivateEquity #AirbnbBusiness #CoHosting #VRMA #StayClassyHomes

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/

🎟️ 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. 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 breaking

The lithium battery threat that's quietly burning down properties

Why pools, dryers, and grills are among the top causes of serious injuries and fires

The insurance trap that leaves hosts uncovered right when they need it most

The simple documentation habit that turns a lawsuit into a defensible accident

Justin's roughly $400 safety setup that protects an entire property

This 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 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 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 before
The "who, not how" mentality: hiring strong operators so you can work limited hours and take Fridays off
How to build experience-driven properties that price out your competition
The simple migration-pattern strategy Michael uses to pick winning markets
Why giving away his exact playbook has only made him more successful
How vertical integration turned one business into an entire ecosystem, almost by accident
Why he's moving into boutique hotels now, and who it's really for
Saying no: how his goals shifted from cash flow to building real enterprise value


Whether 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-elefante

Podcast Chapters:

• 00:00:00 Intro: Traveling the World & Experience-Driven Rentals
• 00:05:37 How Michael Picks Winning Markets (Migration Strategy)
• 00:12:43 Building the RISE Collective & Vertical Integration
• 00:19:18 The Mindset Shift: Buy the Ticket
• 00:22:32 Scaling Home Team + Moving Into Boutique Hotels
• 00:31:00 Long-Term Vision & His #1 Secret to Success

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 wealth.

In this episode, Mike and Mike sits down with Alex Steeg, co-founder of Shore Way Management. Alex and his wife Rachel started in 2018 with one property, zero experience, and a simple plan to "buy a duplex a year." A random Craigslist job post pulled them into the short-term rental world. Just 10 months later, Alex quit his day job for good.

Fast forward to today: they manage 40+ short-term rentals and own a 10-room hotel. Alex runs the hotel in just two hours a week, and the profits alone cover all of his family's living expenses.

In this conversation, we cover:

• How Rachel landed 2-3 clients in her first week using simple cold outreach
• The mental shift that made them hire their first VA (and why they waited too long)
• Taking a hotel from losing $70K a year to making huge profits
• The true differences between managing short-term rentals versus a hotel
• Why hotels build wealth while rentals build cash flow (and the simple math behind it)
• Growing revenue by 40% in a year without adding new listings
• Building a winning team: VAs, inspectors, a concierge, and hiring family
• How referrals and a Google Business page became their top growth engines
• Alex's #1 secret to success: stewardship and working with absolute integrity

Whether you run a few short-term rentals or want to buy your first hotel, this episode gives you the exact steps to turn active income into lasting wealth.

Connect with Alex Steeg:

🌐 Website: https://shorewaymgmt.com

📧 Email: [email protected]

📸 Instagram: https://www.instagram.com/alexsteeg

🏨 Stay at the hotel: Ipswichinn.com

🎟️ 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
━━━━━━━━━━━━━━━━━━━━━━━━━━━━
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
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🎟️ Ready to build? strsecrets.com/aisummit2 — Sept 29–30