Short Term Rental Secrets Podcast

MICHAEL SJOGREN
  • 4.7 (121)
  • INVESTING
  • UPDATED WEEKLY

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. 37 - The Property Management Sales Playbook (How We Added 6 Owners in Q3 last year)

    1D AGO

    37 - The Property Management Sales Playbook (How We Added 6 Owners in Q3 last year)

    Want the resources mentioned in the training? Instagram ➡️ https://www.instagram.com/mikereillync/ Follow this link for the Free training: https://level.strsecrets.com/pc-book You want to grow a property management business, you will eventually hit the same wall: You become the person slowing things down. In this video, I share the exact playbook we built before hiring our first salesperson. Inside this training you’ll learn: • The perfect type of property we target • The exact type of homeowner we want to work with • The biggest problems Airbnb owners face today • How we show our value to sign new clients • The "UI Method" for finding struggling Airbnb properties • The exact numbers and goals we set for our sales team • The best ways we find and talk to new owners • Our step-by-step sales process and first phone calls • What happens right after an owner signs with us If you want to grow your company to 30, 40, or 50+ properties, you need a sales plan that works every single time. This episode shows you exactly how we built ours. Subscribe for new weekly videos ➡️ https://bit.ly/2Nrn4XO Timestamps: 00:00 – Why You Need a Sales Plan 01:12 – The 4 Steps of Our Sales Playbook 02:10 – Finding the Perfect Property 03:05 – The Perfect Homeowner 04:18 – Problems Airbnb Owners Face 05:45 – Creating a Strong Offer 07:00 – Why You Need a CRM Software 08:50 – Sales Goals and Numbers to Track 10:20 – The Experiment: 120 Calls in 6 Weeks 11:35 – Our Sales Win Rates 12:18 – How to Find Leads: The UI Method 13:30 – Using Referrals and Partners 14:05 – Direct Mail and Ads 15:05 – Running Facebook Ads for Leads 16:10 – Our Sales Process 17:20 – The First Call and Asking Questions 18:15 – Handling Owner Concerns 19:05 – Bringing on a New Owner 20:00 – Weekly Sales Tracking 21:10 – Hiring and Testing a Salesperson Connect with us on other social media platforms: STR Secrets FB group ➡️ https://www.facebook.com/groups/STRentalsecrets Michael Sjogren FB Page ➡️ https://www.facebook.com/theAirbnbGuy Instagram ➡️ https://www.instagram.com/miike.sjogren Linkedin ➡️ https://www.linkedin.com/in/mikesjogren

    22 min
  2. Ep - 283 From Bankruptcy to a $100M Real Estate Vision with Jonathan St.Leger

    4D AGO

    Ep - 283 From Bankruptcy to a $100M Real Estate Vision with Jonathan St.Leger

    He built a “sexy” real estate portfolio in the early 2000s… Then 2008 hit. Reserves drained. Assets liquidated. Eventually — bankruptcy. Most investors never come back from that. In this episode, Jon St. Leger breaks down: • What the 2008 crash really felt like • Why he keeps his portfolio at 33% LTV • How to prepare for the next recession • What “Equity Manifestation” actually means • How he turned a 20-room motel into a 47-key boutique hotel • Why delayed gratification builds real wealth • The blue-collar advantage most people ignore Jon now owns 13+ short-term rentals, long-term rentals, and is breaking ground on a beachfront boutique hotel in the Outer Banks. If you’re serious about building generational wealth in real estate — this one is different. Follow Jon on Instagram: @jon_boy14 Get FREE Access to our Community and Weekly Trainings: https://group.strsecrets.com/ TimeStamps: 00:00 – Equity Manifestation & The $100M Vision 02:00 – Identity, Mindset & Future Self Thinking 05:30 – From Blue Collar Beginnings to Construction Company 09:45 – Building a Portfolio… Then 2008 Hit 12:30 – The Mental Toll of Bankruptcy 14:45 – Lessons From the Crash: Reserves & Exit Strategies 17:00 – Why He Keeps 33% Loan-to-Value 19:00 – Not Overleveraging in Growth Cycles 21:30 – From STR Portfolio to Boutique Hotel Developer 24:00 – Turning a 20-Room Motel into 47 Keys 27:00 – Getting Town Buy-In & Emotional Attachment 30:00 – Leading Teams & Maintaining Morale 32:30 – The Power of Delayed Gratification 35:00 – Return on Sweat Equity (R.O.S.E.) 37:00 – Blue Collar Wealth Strategy 39:00 – The $100M Real Estate Target 41:00 – Where Opportunity Lives & Final Advice

    43 min
  3. The 4-Step Airbnb Photography System That Wins in 2026

    FEB 26

    The 4-Step Airbnb Photography System That Wins in 2026

    2026 is going to separate serious operators from everyone else. Supply is rising. Middle-class travel is tightening. Occupancy is projected to decline. Rates are compressing. If your Airbnb still looks like 2024… you're in trouble. In this training, I break down my full 4-step photography system: – What to upgrade BEFORE hiring a photographer – How to properly interview lifestyle photographers – What to do on photo day to maximize impact – How we use AI to write captions and enhance photos – How we organize everything inside our operating system If you’re scaling a property management or co-hosting business, this is not optional anymore. Timestamps: 00:00 – Why 2026 Will Be Harder for STR Operators 02:12 – Supply Is Rising, Occupancy Is Falling (The Reality Check) 03:30 – Step 1: Refresh Before You Photograph 06:10 – Using ROI Analysis to Justify Property Upgrades 09:20 – Real Estate vs Lifestyle Photography (Huge Difference) 12:05 – What Elite STR Photos Actually Look Like 16:00 – How to Properly Interview a Photographer 19:10 – Photo Day Execution: Staging That Converts 22:15 – Organizing Photos for Scalable Operations 25:00 – Using AI to Write Captions for Every Photo 27:00 – Editing & Enhancing Photos with AI 29:15 – The Freedom Operating System Explained 32:00 – How to Scale Photography Across Multiple Listings 34:15 – Mastermind, CRM, and 2026 Growth Strategy 36:50 – Final Advice: Upgrade or Get Left Behind Get FREE Access to our Community and Weekly Trainings: https://group.strsecrets.com/

    37 min
  4. Ep - 282 What’s Actually Holding Your STR Business Back

    FEB 23

    Ep - 282 What’s Actually Holding Your STR Business Back

    Most entrepreneurs think they need better strategy. They don’t. In this Boardroom recap from the Freedom Factory, we unpack the real reasons businesses stall — and it’s not systems. It’s people, identity, and the state you operate from. Inside this episode: • Why most business bottlenecks are solved by the right “who” • The difference between hiring people and developing talent • W2 vs 1099 mistakes operators make • Why State → Story → Strategy is the real order of success • The 4 archetypes running your decisions (Warrior, Magician, Lover, Sovereign) • Why high performers get stuck in Warrior mode • How seasonality applies to your business and your life • Why kindness to yourself is a competitive advantage If you feel like something is holding you back… this episode will hit. Timestamps: 00:00 – Boardroom at the Freedom Factory Recap 02:15 – From Cooked Books to 80,000 Meals a Week 04:10 – Visionaries Get Small When Stuck in Operations 05:45 – The “Right Who” Solves Most Bottlenecks 07:50 – Building Talent Structure (Not Just Hiring) 10:40 – W2 vs 1099: What Operators Must Understand 12:20 – The 3 S’s of Breakthrough: State > Story > Strategy 15:05 – The 4 Archetypes Running Your Life 18:30 – Warrior Mode & The Seasonality of Growth 21:10 – Kindness, Presence & The Power of Awareness Get FREE Access to our Community and Weekly Trainings: https://group.strsecrets.com/

    26 min
  5. Ep - 281 Why Midterm Rentals Are the Smarter STR Strategy with Vivian Yip

    FEB 16

    Ep - 281 Why Midterm Rentals Are the Smarter STR Strategy with Vivian Yip

    Vivian Yip went from corporate burnout at Apple to building a thriving midterm rental portfolio and property management company. In this episode, she breaks down how she pivoted during the pandemic, why most investors don’t have enough grit, and how mastering calendar discipline can completely transform your rental income. We dive into: • Why community changes everything in real estate • The biggest mistake STR hosts make when pivoting to midterm rentals • Calendar discipline and how to control guest behavior • How to use data tools like PriceLabs the right way • Building multiple income streams without burning out • Protecting your time while scaling a real estate business If you’ve been feeling stuck, burned out, or uncertain about the next step in your rental business — this episode will challenge you to think differently. Timecodes: 00:00 – Intro 03:12 – Why Community Is a Competitive Advantage 05:00 – The Power of Grit in Business 07:02 – Vivian’s Real Estate Journey (2004–2018 Gap Explained) 09:56 – Corporate Burnout at Apple & Transferable Skills 13:05 – Why Most Investors Pivot Too Fast 16:48 – Why Midterm Rentals Make More Strategic Sense 21:41 – The Calendar Discipline Most Hosts Ignore 25:31 – Transitioning from STR to MTR the Smart Way 30:29 – Why Vivian Built Her Own Platform 35:07 – Building Teams Without Burning Out 38:10 – Setting Boundaries & Protecting Your Time 42:05 – The 80% Confidence Rule (Just Do It) Guest Bio: Vivian Yip started investing in 2004 but took her journey more seriously after being inspired by a hotel owner she met at a random airport encounter in Chicago. She and her husband started to flip houses in 2018 and ended up making enough to afford to keep the real estate. She always dreamed of leaving the corporate world, so she used her steady paycheck at Apple to support their real estate goals. In 2019, she started her first short-term rental and was forced to pivot in 2020 with the pandemic. Now she runs multiple businesses focused on short-term rentals, mid-term rentals, and corporate housing, and she coaches others on the strategy behind securing profitable leases from Airbnb and beyond. Guest Link: Instagram.com/vivianyip_official vivian@vivianyip.com Get FREE Access to our Community and Weekly Trainings: https://group.strsecrets.com/

    42 min
  6. Ep - 280 - How Influencer Marketing Really Works for STRs (And Why Most Hosts Get It Wrong) with Madison Rifkin

    FEB 9

    Ep - 280 - How Influencer Marketing Really Works for STRs (And Why Most Hosts Get It Wrong) with Madison Rifkin

    Most STR hosts misunderstand influencer marketing — and it’s costing them bookings. In this episode, Madison Rifkin breaks down what actually works when partnering with content creators, why follower count is a useless metric, and how STR operators should think about social media as a long-term control channel — not a quick ROI play. We also go deeper into founder identity, building brands that can be sold, and the mistakes operators make when they tie everything to themselves. If you want more direct bookings, stronger brand trust, and a business that isn’t dependent on Airbnb alone, this episode is required listening. Inside the episode: • Why follower count doesn’t matter anymore • How to vet influencers the right way • The real way to think about ROI from content creators • Why social media is your only true control channel • Content ideas that work even without a “viral” property • Founder identity mistakes that kill exits • How to build a brand that survives without you Timestamps: 00:00 – Why Influencer Marketing Is Broken for Most STR Hosts 03:20 – Madison’s Journey Building Mount and Entering STRs 06:40 – Why Follower Count Is a Terrible Metric 10:10 – How to Vet Influencers Based on Brand Alignment 13:30 – The Truth About ROI in Influencer Marketing 17:10 – Why Social Media Is a Control Channel, Not an Ad 20:00 – Content That Works Without a “Viral” Property 23:10 – Founder Identity and Why It Hurts Exits 26:30 – Building a Brand That Isn’t Tied to You 30:45 – Lessons From Selling a Company and Starting the Next Chapter Guest Bio: Madison Rifkin is the Founder and CEO of Mount where she finds the world's best hidden gems. She connects STR hosts and local businesses to local influencers and travel content creators so travelers can discover these hidden gems. She’s rooted in the Short Term Rental Industry where she’s won the Rising Star Award in 2022 and 2023. Guest links: https://www.linkedin.com/in/madison-rifkin-23037712a/ Get FREE Access to our Community and Weekly Trainings: https://group.strsecrets.com/

    38 min
  7. Ep 279 - Why Conviction Beats Experience in Building a Real STR Business with Hailie Anderson

    FEB 2

    Ep 279 - Why Conviction Beats Experience in Building a Real STR Business with Hailie Anderson

    Success in STR isn’t about age, capital, or the model you choose — it’s about conviction. In this episode, we sit down with Hayley Anderson, a 22-year-old operator already on her second business, to unpack the mindset, discipline, and leadership traits that actually drive growth. From failing early to building confidence through reps, this conversation goes far beyond arbitrage or co-hosting. If you want to scale your business — or your life — this episode will challenge how you think about comfort, confidence, and commitment. Inside the episode: • Why conviction matters more than experience • How confidence is built through reps and failure • The leadership habit that quietly builds culture • Why comfort is the enemy of growth • Learning to bet on yourself before results show up • Applying mindset across business, relationships, and life Timestamps: 00:00 – Intro 04:20 – Hayley’s Early Hustle and Second Business at 22 08:10 – Confidence Is Built Through Reps, Not Motivation 12:30 – Failing Early Without Letting It Define You 16:40 – Comfort vs Growth: The Tradeoff Most Avoid 20:15 – Leadership Starts With Small Cultural Habits 24:35 – Betting on Yourself Before Results Show Up 29:00 – Applying Mindset Across Business and Life 33:40 – Why Age, Model, and Capital Matter Less Than Belief 38:10 – The One Trait That Predicts Long-Term Success Guest Bio: Hailie Maarie Anderson is a 22 year old short term rental host operating over 70 rentals across three markets, all run 100% remotely through a blend of technology and teams. While scaling her own portfolio, she has taken the stage at industry events to share her systems and insights, and has successfully coached over 1,300 individuals to start and scale their own short term rental businesses. Hailie’s mission is to be a leading voice for those who want to build and live an unconventional life, one without limits! Guest Link: https://www.instagram.com/hailiemaarie/?hl=en https://www.tiktok.com/@hailiemaarie https://youtube.com/@hailiemaarie?si=3qCgG6OPXqwZTgU2 https://www.linkedin.com/in/hailie-maarie-4b20a5276/ Get FREE Access to our Community and Weekly Trainings: https://group.strsecrets.com/

    42 min
  8. 2026 Is a Reset Year for STRs — Here’s How to Win Before Others Fall Behind | The STR Scale Show with Mike Reilly | Ep 35

    JAN 29

    2026 Is a Reset Year for STRs — Here’s How to Win Before Others Fall Behind | The STR Scale Show with Mike Reilly | Ep 35

    The STR market isn’t crashing — it’s recalibrating. In this episode, we break down AirDNA’s 2026 outlook and translate the data into real, tactical decisions for hosts and property managers. Demand is softening, supply is shifting, and average properties are losing ground — but operators who adapt will win. This is a data-backed walkthrough of what’s changing, why it matters, and exactly what to do next. If you want the Training on how you should look at increasing your pricing so that you are not making 15 to 18% less than you were a year over year just click the link and DM "FEE". https://ig.me/m/mike.sjogren?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T035&utm_content=FEE Inside this episode: • What AirDNA’s 2026 data actually says about demand and supply • Why average properties will lose occupancy and revenue • The markets and property types positioned to outperform • How to talk homeowners into smart upgrades (with ROI) • Why property managers are pulling ahead of solo hosts • Using AI and systems to protect reviews and prevent burnout 00:00 – What the 2026 STR Outlook Means for Hosts & Property Managers 03:30 – Why STR Supply Has Flattened (And Why That Matters) 06:10 – Demand Is Softening: The Economic Reality Hosts Must Accept 09:15 – Average Properties Will Lose Occupancy in 2026 12:00 – Why Larger, Luxury Properties Are Winning Again 15:00 – Shedding Low-Performing Properties to Refocus Growth 18:20 – Coastal & Urban Markets: Where Smart Money Is Moving 21:00 – How to Sell Homeowners on Strategic Property Upgrades 24:30 – Property Managers vs Solo Hosts: The Performance Gap 27:40 – AI, Systems, and the Only Way to Scale Without Burning Out Get FREE Access to our Community and Weekly Trainings: https://group.strsecrets.com/

    32 min
See All (349)

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

Information

You Might Also Like