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

    1d ago

    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.

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

    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

    41 min
  3. Why "7 Streams of Income" is the Biggest Lie in Entrepreneurship | Dave Menapace

    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

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

    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"

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

    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

    50 min
  6. The AI Comp Tool That's Getting STR Managers 7 Sales Calls a Week

    May 28

    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 demo the AI-powered comp analysis tool that's helping property managers turn more conversations into signed contracts. Ryan went from 1-2 comp requests a week to 10 a week — from realtors and investors who now send him every new listing because he delivers branded, data-backed reports in minutes, not hours. In this episode: → The exact tool Ryan built using Claude that generates a full comp report in 2 to 10 minutes (vs. 20-30 minutes manually) → How to use conservative, base, and optimistic revenue projections to handle any homeowner conversation on the spot → Why realtors are becoming one of the fastest referral pipelines for new management contracts — and how to tap in → The AI rabbit hole warning: why building your own tools can quietly kill your business growth → Mike's financial freedom math: exactly how much you need invested to hit $100K a month in cash flow → Why arbitrage is a dead end — and what the data on the biggest arbitrage companies actually shows This is not theory. Ryan runs live comps during the session on real properties submitted by the audience — you'll see exactly how the tool works in real time. Want the comp tool? DM COMP at mike.sjogren and we'll send it straight to you. Ready to install this and a full AI system for your business live? Timestamps: 00:00 - Intro & Ryan Lefebvre's background 01:42 - From financial crime analyst to AI builder for STR 04:22 - How the comp tool works and what it produces 06:33 - Live demo: running an Airbnb listing in real time 09:26 - Interactive sliders and revenue scenario conversations 11:17 - How to handle bad comps and sparse markets 13:36 - Live demo: running a property address 17:34 - How the tool handles off-market or renovated properties 22:38 - Using comp reports to show homeowners the gap between unmanaged and managed 26:41 - AI Summit: what's being covered and who's speaking 29:04 - Ticket pricing and how to register 32:02 - Alex case study: 2 properties to 35 in one year 35:29 - The AI rabbit hole warning 38:00 - Using AI at any portfolio size 41:06 - Mike's financial freedom math ($8M at 15% = $1.2M/year) 44:46 - Why arbitrage is a dead model 49:27 - Should you replace your channel manager with AI? (No. Here's why) 52:45 - Q&A: summit details, recordings, revenue manager AI tool

    58 min
  7. Why Your STR Business Stopped Growing (And It's Not the Market)

    May 25

    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. In this episode: → The 3 silent causes of business stagnation (and which one is quietly killing your growth right now) → Why split focus will never equal scale — and the one decision Chris made that changed everything → The identity gap: how to stop making decisions from who you've been and start making them from who you're becoming → E's 5 daily affirmations that rewire how you start every single day → Why hiring for today's need is the biggest mistake scaling operators make If the last six months didn't go the way you planned, this episode is your reset. Ready to build the business that funds the life? Apply to work with us: strsecrets.com/apply

    37 min
  8. She Built an AI Agent That Creates 10 Carousels From One Airbnb Link | Dr. Rachel Gainsbrugh

    May 21

    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 curtain on the exact AI content engine she built to generate weeks of social content without living on her phone. Dr. Rachel is a former full-time physician turned full-time real estate investor, entrepreneur, AI strategist, and founder of Short Term Gems. She built her entire content system out of necessity — and now it runs largely without her. In this episode, Mike Sjogren sits down with Dr. Rachel to walk through the full system live: from raw meeting notes to scheduled carousels, with AI agents doing most of the heavy lifting. What you'll learn: → The 7-11-4 rule: why buyers need 7 hours of content across 11 touchpoints on 4 platforms before they trust you enough to write you a check → Meet Vega — the AI agent that processes all your meeting notes every night and sorts them into content, SOPs, and coaching opportunities before you wake up → Meet Carrie — the carousel sniper that takes one Airbnb link and delivers 10 ready-to-post carousels including captions and CTAs → Meet Contesta — the content queen that formats everything for each platform and sends it to scheduling automatically → How a property manager with 80 doors sent 60 personalized owner emails in 2 hours (he used to spend his whole weekend on it) → How to train your AI like an employee using SOPs — and why that one step changes everything → The AI data privacy protocol that keeps your sensitive files in a sandbox and out of reach → Why posting once or twice a week means you are already losing to operators using this system 🎙️ Guest: Dr. Rachel Gainsbrugh | Founder, Short Term Gems 🔗 Get Carrie the Carousel Sniper Agent: https://level.strsecrets.com/drrachel ───────────────────────────── ⏱️ TIMECODES 00:00 - Cold open: Carrie the carousel sniper demo — one Airbnb link, ten carousels 00:57 - Mike and Dr. Rachel intro — why she's the go-to AI person in the space 01:34 - Dr. Rachel's background: from full-time doctor to AI-powered STR investor 02:13 - The 7-11-4 rule: the Modern Trust Formula every operator needs to understand 03:04 - Two content angles for STR operators: repeat guests and new client acquisition 03:39 - Why Dr. Rachel built this system (she hates being on camera) 05:24 - The note taker habit that turns every meeting into a content asset 05:48 - The Plaud Note Pin: the wearable AI recorder Mike and Rachel swear by 07:09 - Meet Vega: the AI night agent that sorts all your meetings while you sleep 07:53 - How Vega triages every meeting into four buckets before you wake up 08:15 - Real demo: Vega identifies a coaching frame used 14 times across calls and flags it 09:23 - 425 meetings reviewed by AI that no human ever had time to touch 09:56 - How Vega processes data directly from Fireflies, Otter, and Plaud using schema 13:22 - Step two: turning the content database into actual social posts with Contesta 13:58 - Real proof: 80-door property manager sends 60 personalized owner emails in 2 hours 14:22 - How Contesta routes content to Phoebe (Facebook) and schedules it automatically 15:15 - How Mike applies this to property walkthroughs and hotel renovation updates 16:14 - Why guest reviews are an untapped content goldmine most operators ignore 17:20 - The one thing Dr. Rachel warns against: asking AI to write posts with no context 18:05 - How to sell through your real stories: the three-part owner acquisition framework 19:15 - Mike's local events agent: scraping tourism data to feed newsletters and social 20:18 - Why showing your journey (not the polish) is what builds trust and drives bookings 21:46 - Meet Carrie: the carousel sniper — live demo walkthrough 23:11 - Carrie in action: pulling property photos from Airbnb, building 8-10 slide carousels 24:50 - Guest reviews as carousel slides: 122 reviews turned into content automatically 25:29 - Carrie delivers: full carousel batch plus caption, CTA, and downloads folder 26:00 - Is all of this through Claude? Yes — Claude Co-Work and Claude Code 27:04 - How long it took to build Carrie (two months) and how fast it runs now (one command) 28:44 - Train AI like an employee: the SOP-first method for consistent results 29:49 - Real world result: executive assistant elevated from admin to EA after AI frees her up 31:47 - Dr. Rachel is speaking at the AI Summit — two full hours of live building with you 33:43 - How to train Claude with SOPs, PDFs, and audit loops 35:26 - AI quality is only as good as your SOP — garbage in, garbage out 36:31 - Who owns your property photos? What every operator needs in their photographer contract 37:19 - The Night Janitor: the AI agent that organized 16,000 photos and files in minutes 39:15 - How to talk to Claude about your messy photo library and get a real solution 41:05 - Claude Code vs. Claude Co-Work: when to use which for scheduling and automation 41:35 - Should you have separate social accounts for owner acquisition vs. guest direct bookings? 43:49 - Training AI vs. training humans: why right now is the best time to be an operator 47:02 - AI Summit preview: June 23-24, Freedom Factory, Beverly MA — build it live with Rachel 48:19 - The volume reality: someone using this system is posting 3x a day while you post twice a week ───────────────────────────── 🎁 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 #ShortTermRental #AIforSTR #STRSecrets #VacationRental #PropertyManagement #ContentStrategy #AirbnbInvesting #AIAgents #DirectBookings #STRScaling

    49 min
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4.7
out of 5
121 Ratings

About

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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