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

    5D AGO

    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
  2. 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
  3. 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
  4. Ep 278 - How Great Leaders Scale Teams Without Losing Control with Ryan Leake

    JAN 26

    Ep 278 - How Great Leaders Scale Teams Without Losing Control with Ryan Leake

    Scaling isn’t a systems problem — it’s a leadership problem. In this episode, we break down what actually changes when you go from being a solo operator to leading a real team. From earning respect instead of demanding it, to building systems that support people (not suffocate them), this conversation unpacks the leadership shifts required to scale without chaos. If you’re growing doors, people, or partnerships — this episode will change how you think about leadership. Inside the episode: • The two ways leaders earn respect (and why only one works) • Why supporting team members’ goals makes you more valuable • How ego quietly slows down growth • Leading teams through systems, not micromanagement • What it really takes to earn buy-in as a leader • Why consistency beats motivation when scaling 00:00 – The Two Ways Leaders Show Up (Title vs Example) 04:10 – Why Supporting Team Growth Makes You More Valuable 08:05 – From Solo Operator to Leading People 12:30 – Letting Go of Ego to Scale Faster 16:05 – Earning Respect Without Authority 20:10 – Using Systems to Reduce Team Burnout 24:05 – Aligning Company Goals With Personal Goals 28:00 – Consistency Over Motivation in Leadership 32:10 – Scaling Teams Without Losing Culture 36:20 – The Leadership Standard That Sustains Long-Term Growth Guest Bio: Ryan Leake, originally from Mill Valley, CA, moved to Austin, TX in 2023, where he left corporate America and founded Host Del Casa, a short-term rental management company. After successfully building the business, Host Del Casa merged with Five Star Vacation Home Rentals (FSVHR), where Ryan now serves as a Managing Partner for the #1 luxury short-term rental management company in Central Texas - managing 60+ luxury short-term rental properties across Austin and San Antonio. In addition to his role at FSVHR, Ryan became a coach and consultant for STR Secrets, the leading short-term rental business coaching program, where he helped operators overcome self-limiting beliefs and build profitable, lifestyle-driven STR businesses. Today, Ryan continues to coach and mentor new short-term rental operators, share insights as a thought leader in the space, and prioritize a life designed around freedom, impact, and balance. Guest Link: www.instagram.com/itsaleake ryan-leake.com fivestarvhr.com Get FREE Access to our Community and Weekly Trainings: https://group.strsecrets.com/

    41 min
  5. Ep 277 - Tech, Teams, and the Emotional Cost of Scaling STR Businesses with Frank Bosi

    JAN 19

    Ep 277 - Tech, Teams, and the Emotional Cost of Scaling STR Businesses with Frank Bosi

    Most operators think better tech will fix their problems. It won’t. In this episode, Frank Bosi (Hostfully) joins the show to unpack the real challenges STR leaders face as they scale—pressure, decision fatigue, emotional weight, and the constant tension between automation and hospitality. Drawing from years inside luxury hotels like Ritz-Carlton and Four Seasons, Frank breaks down what most operators get wrong about tech stacks, leadership, hiring, and guest experience—and how to build systems that create confidence instead of doubt. Inside this episode: Why tech stack decisions are emotional, not logicalHow disconnected tools quietly create leadership stressThe difference between automating tasks vs removing hospitalityWhat luxury hotels get right about training and consistencyWhy leaders must absorb pressure instead of passing it downHow to hire people who protect your brand when you’re not watching This is a must-listen for any STR operator building a team, scaling systems, or feeling the weight of leadership. 00:01 – Why Tech Stack Decisions Are Emotional, Not Logical 03:45 – Automation vs Hospitality: Where Operators Go Too Far 07:10 – The Weight of Leadership Most People Aren’t Ready For 11:00 – Why Disconnected Tools Create Doubt and Stress 15:20 – Lessons STR Operators Can Steal From Luxury Hotels 19:10 – Why Leaders Can’t Have “Bad Days” Publicly 23:30 – Hiring People Who Protect Your Brand When You’re Not There 27:40 – Training, Standards, and Why Consistency Beats Luxury 31:50 – Using Tech to Create Confidence, Not Complexity 36:40 – The Real Role of a Leader in Scaling STR Operations Guest Bio: Frank Bosi is the Senior Director of Partnerships at Hostfully, a leading platform supporting short-term rental operators around the world. He drives strategic relationships across the STR ecosystem; working with technology partners, influencers, coaches & thought leaders to help property managers scale and deliver great guest experiences. Frank also actively contributes to industry conversations through webinars, events and podcasts (such as this) designed to help operators grow smarter, faster, and more profitably. Outside of work, Frank prioritizes faith, fitness, and family; spending his free time with his wife and kids, training CrossFit, and staying focused on overall wellbeing. Guest Link: https://www.instagram.com/frank_bosi/ Get FREE Access to our Community and Weekly Trainings: https://group.strsecrets.com/

    43 min
  6. Ep 276 - Your Calendar Is Exposing Why You’re Not Hitting Your Goals

    JAN 12

    Ep 276 - Your Calendar Is Exposing Why You’re Not Hitting Your Goals

    Your goals aren’t failing — your calendar is. In this episode, E and Chris break down why most people start the year motivated… then quietly drift back into old patterns. The problem isn’t strategy, tools, or ambition — it’s misalignment between who you say you want to become and how you actually spend your time. This conversation dives deep into identity, courage, time audits, consistency, and the hidden habits that either compound your growth or quietly sabotage it. Inside this episode: Why your calendar tells the truth about your real prioritiesThe “perfect week” exercise that exposes misalignment fastWhy every new level requires letting go of your old identityHow fear, comfort, and ego silently slow your progressThe power of small, consistent actions over big intentionsWhy courage often means saying “no,” not “yes” If you’ve ever felt busy but stuck — this episode will hit home. 00:00 – Why New Year Motivation Dies Faster Than You Expect 02:05 – The Reality Check: When Goals Collide With Real Life 04:20 – The Calendar Test: Do Your Actions Match Your Goals? 07:40 – Designing Your “Perfect Week” (And What It Exposes) 10:55 – Your Dreams Are Expensive — Here’s the True Cost 14:30 – Killing the Old Version of Yourself to Level Up 17:55 – Faith vs Fear: Making Decisions Without Freezing 21:30 – Small Habits That Quietly Compound Massive Change 25:10 – Letting Go of Ego to Create Space for Growth 29:05 – Enjoyment, Consistency, and Becoming Your Best Self Get FREE Access to our Community and Weekly Trainings: https://group.strsecrets.com/

    30 min
  7. Ep 275 - The New Standard for STRs: Design, Ops, and Discipline with Shane O'Connor

    JAN 5

    Ep 275 - The New Standard for STRs: Design, Ops, and Discipline with Shane O'Connor

    The STR game has changed—and most operators haven’t caught up. In this episode, we break down what actually separates top-performing short-term rentals from the ones stuck in the middle. From design and amenities to operations, leadership, and systems—this is a real look at how elite STR businesses are built and sustained in hyper-competitive markets. This isn’t theory. It’s what’s working right now. Inside this episode: - Why “good enough” STRs are getting crushed - The amenity arms race (and how to win without wasting money) - What guests notice that most hosts completely miss - How ops and hospitality matter more than design long-term - Why disciplined systems protect profit—even in down years - The leadership mindset required to scale without chaos If you want longevity in this industry, this episode is required listening. 00:06:15 – Becoming “The Guy” in a Hyper-Competitive STR Market 07:45 – Why Copying Competitors Is a Losing Strategy 09:15 – The New Minimum Standard for STR Design & Amenities 11:40 – Why Half-Upgraded Properties Always Underperform 18:50 – The Amenity Arms Race: What Actually Moves Revenue 20:00 – When Design Stops Mattering and Ops Take Over 26:10 – Building Teams and Systems That Don’t Break Under Stress 30:45 – Leadership Lessons from Military and STR Operations 34:05 – How Efficiency Protects Profit in Down Revenue Years 39:35 – The Long-Term STR Play: Scale, Discipline, and Longevity Guest Bio: Shane O’Connor is the CEO & Founder of Alchemy Real Estate & Alchemy Hosting. Alchemy is based in Tampa, FL, building a portfolio of Short-Term Rental assets primarily focused in Central Florida. By delivering vertically integrated, top-tier service from beginning to end in the investment process, Alchemy has grown from a single property (and single employee) to 11 properties & a team of four in less than a year. In that same time, Alchemy will have also delivered more than $3M in closed real estate deals for its clients. By the end of 2022, it is Shane’s goal to have a blended Direct Ownership & Co Hosting portfolio of 30 properties centered in Florida, to then begin expanding to other markets. Shane is a graduate of the United States Naval Academy and served as an Officer in the U.S. Navy for 9 years. He received an M.S. Degree in Real Estate from the University of Florida. He runs the company with his brother, Captain Devin O’Connor, who is an active duty Marine Corps helicopter pilot in addition to being the Director of Operations for Alchemy. Guest Link: https://www.instagram.com/oc_dreams19/ Get FREE Access to our Community and Weekly Trainings: https://group.strsecrets.com/

    43 min
  8. Ep 274 - Stop Setting Goals. Start Becoming This Person

    12/29/2025

    Ep 274 - Stop Setting Goals. Start Becoming This Person

    Most people don’t fail because they lack discipline — they fail because they’re trying to grow without changing who they are. In this episode, Chris and E break down why goals alone don’t create change, how identity drives momentum, and the real reason most people stall out by February. This is a deep, practical conversation on discipline, accountability, emotionalized goals, and how to build habits that actually stick. If you’ve ever felt stuck despite “doing all the right things,” this episode will reframe how you think about growth — personally and professionally. Inside this episode: • Why identity matters more than motivation • How emotionalized goals create automatic discipline • The “never two days in a row” rule that builds momentum • Why most people sabotage themselves without realizing it • How to design accountability that actually works • Turning small daily actions into long-term transformation 👉 If this episode resonated, share it with someone who’s setting big goals this year — and subscribe for more real conversations on growth, leadership, and execution. 00:00 – Why the Point of a Goal Is Growth, Not the Outcome 02:05 – Identity vs Outcomes: The Real Way to Set Goals 04:20 – Emotionalizing Goals to Create Immediate Action 06:10 – Going Deeper on “Why” Using the Seven Layers Exercise 08:35 – Shifting from “I Have To” to “I Get To” 10:15 – Building Momentum with Small, Non-Sexy Wins 12:40 – Vision First: Thinking Big Enough for the Next Level 15:05 – Quarterly Sprints and the Power of the 12-Week Year 17:40 – Time Blocking Life, Family, and Business (In That Order) 20:30 – Accountability, Never Missing Twice, and Staying in Motion Get FREE Access to our Community and Weekly Trainings: https://group.strsecrets.com/

    33 min
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4.7
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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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