Short Term Rental Secrets Podcast

MICHAEL SJOGREN
  • 4.7 (121)
  • Investing
  • Updated Biweekly

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

  1. 14h ago

    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.

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

  2. Jul 13

    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 yearsThe 6 stages of onboarding: Handoff, On-Site Setup, Photography, Listing & Software Setup, Final Touches, and Post LaunchHow Mike's team uses Meta glasses to capture every inch of a home and turn it into checklists automaticallyThe QR code trick that eliminates guest questions about the grill, hot tub, sauna, and game roomThe exact roles to hire: project manager, contractor help, listing team, and data qualityHow one Pinehurst property pulled $30,000 in bookings from mood boards alone, before it was even readyThe 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

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

  3. Jul 6

    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

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

  4. Jun 29

    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.

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

  5. Jun 22

    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

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

  6. Jun 15

    Why "7 Streams of Income" is the Biggest Lie in Entrepreneurship | Dave Menapace

    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

    Why "7 Streams of Income" is the Biggest Lie in Entrepreneurship | Dave Menapace

  7. Jun 8

    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 — and explains exactly why so many operators stay stuck despite doing all the right things. If your results haven't caught up to your effort, this episode is for you. What you'll learn: → Why goals are working against you — and why standards change everything → The thermostat analogy: why your belief system resets your results back to where they've always been → The LOVE framework for breaking old identity patterns (Liberate, Optimize, Velocity, Elevate) → Why external validation from clients is a ceiling on your business → The one question that shows whether your internal story matches your external goals → E's 5 daily affirmations and exactly how to use them morning and night 📘 Free 6-step STR course: level.strsecrets.com/pc-book 💬 Join us: STR Secrets Facebook Group Timestamps: 00:00 - Why E goes to Italy every summer (and what it actually cost to get there) 09:00 - Stop setting goals. Start setting standards 12:00 - The LOVE framework: how to free yourself from old stories 16:00 - The thermostat analogy: why doing the work is not enough 20:00 - Three questions to ask yourself right now 23:00 - The 5 affirmations that reset your identity every single day"

    Working 24/7 But Still Stuck? This is why Your STR Business Isn't Growing

  8. Jun 1

    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 later, Mark has 18 AI agents running inside Boostly. They've generated $54,000 in revenue. And he says he's never hiring a human setter again. Mark Simpson is the founder of Boostly — the company helping STR operators escape over-reliance on Airbnb and own their direct bookings. He grew up on a farm in North Yorkshire, where his family ran a BNB. Over the last decade, he's refined the most complete direct bookings playbook in the vacation rental industry. Now on his 7th appearance on the show, he's back with the rawest, most honest take on AI agents we've had to date. This is his blueprint for direct bookings, AI agents, and what's about to happen to operators who don't adapt. What you'll learn: → Why Mark predicts Airbnb's commission is going from 15.5% to 20% — and what the data shows → The 65% direct booking goal — and why going 100% direct is just as dangerous as 100% Airbnb → The 3 things every direct booking website needs that 90% of operators still get wrong → The exact story of Icarus: how Mark built his first AI agent in 2 days and made his money back in 7 → How Boostly went from a team of 20 to a team of 150 without hiring a single human → Why 0.05% of people pay for AI Pro — and how $18 a month puts you in the top 99.5% globally → The "18 minutes a day" rule that quietly turns operators into AI power users → How Mark trained his entire 22-person team on AI without overwhelming a single person → The honest answer to "are you teaching your team to replace themselves?" → Why "the cream rises to the top" — and which roles are about to disappear 🎙️ Guest: Mark Simpson | Founder, Boostly 🔗 Website: https://www.boostly.co.uk 🔗 Boostly Connect: https://boostlyconnect.com 🔗 LinkedIn: Mark Simpson 🔗 Instagram: https://www.instagram.com/boostlyuk 🔗 Facebook: https://www.facebook.com/mrmarksimpson 🔗 Book recommendation link: http://bit.ly/2WEOm1v ───────────────────────────── ⏱️ TIMECODES ───────────────────────────── 00:00 - The $50K wasted on human setters and the AI agent that changed everything 01:32 - Mark Simpson returns for his record-breaking 7th episode 02:15 - Life update: 4 kids, World Cup tickets, and the UK trip this summer 03:29 - "Don't build your home on someone else's land" — Mark's signature line 04:00 - Airbnb's fee hike from 3% to 15.5% — and why he saw it coming in 2022 04:30 - The next prediction: why Airbnb is going to 20% commission 06:38 - Top 3 things every operator needs to start direct bookings TODAY 07:02 - Why WordPress still wins in 2026 (and why your PMS landing page isn't a real website) 08:54 - When to flip from "this is a hobby" to "this is a business" (around property 6-7) 09:30 - Why exit-ready businesses always have strong direct booking revenue 11:51 - What does "good" look like? The 65% direct booking benchmark 13:49 - The two-part myth: high-converting website AND content/SEO effort 14:27 - Why hospitality operators are spoiled — and why that's a problem 16:40 - The fundamentals of business that STR operators keep ignoring 17:26 - The "do you know anyone" referral mindset most operators are too scared to use 19:55 - The mirror moment: who do you actually blame for missing your goals? 20:36 - AI agents — Mark's full breakdown starts here 20:57 - Why The Matrix in 1999 still defines how Mark thinks about AI 22:00 - The OpenClaude story: how one weekend GitHub project broke the industry open 24:50 - The breaking point: firing the $50K setter and going all in 25:30 - Meet Icarus — Mark's first AI agent (and the Greek myth behind the name) 26:00 - Real result: $5,000 booking closed in 7 days for under $20 in AI costs 26:30 - 18 agents, $54,000 in revenue, 2 months later 27:19 - Reality check for the shiny object chasers 29:00 - "I'm an idiot" — Mark on why anyone can do this 30:00 - All 22 Boostly employees now have their own AI agent 31:30 - The Google Chrome extension a non-technical team member built in one week 33:00 - The $18 Pro plan stat: why 99.5% of the world isn't paying yet (and what that means for you) 34:00 - The 18 minutes a day rule that compounds into mastery 35:00 - How Mark rolled AI out to his team without overwhelming anyone 36:30 - Comet by Perplexity: the agentic browser changing how teams work 38:04 - "Aren't you teaching them to replace themselves?" The hard question 38:55 - Mark's brutally honest answer (it's not what you think) 41:27 - Why AI Agent Manager is the #1 role being hired for right now 41:51 - The danger of going 100% AI (same risk as going 100% direct) 43:21 - Life on the human side: paddle, books, and saying goodbye to soccer 44:43 - 6 hours back in his day — what Mark plans to do with it 46:55 - The two killers of every operator: lack of attention and poverty of imagination 47:41 - Boostly Connect — the free tool that pulls your PMS data anywhere 49:04 - Mark's #1 secret to AI agent success: just start ───────────────────────────── 🎁 FREE RESOURCES ───────────────────────────── Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets Boostly Direct Booking Playbook (Mark's book): http://bit.ly/2WEOm1v Boostly Connect (free up to 10 listings): https://boostlyconnect.com ───────────────────────────── 🔥 STR AI SUMMIT — June 23-24 | Freedom Factory, Beverly, MA The exact AI systems Mark talks about in this episode? They get built with you LIVE at the summit. Don't just listen to the playbook. Leave with it installed. Only 100 seats. 👉 strsecrets.com/aisummit ───────────────────────────── #ShortTermRental #DirectBookings #AIforSTR #Boostly #STRSecrets #VacationRental #PropertyManagement #AirbnbInvesting #AIAgents #STRScaling

    Direct Bookings, AI Agents & Why Airbnb Fees Are Going to 20% | Mark Simpson Returns
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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

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