Vacation Rental Revolution: Building Lifestyle & Financial Freedom With Short-Term Rentals

Hosted by Shawn Moore

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423

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Nov 2026

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About the show

Learn More More 1% short-term rental properties than any other group, 2,000+ STR investors, and 20+ years of real estate investing experience. Shawn Moore, Founder & CEO of Vodyssey, and bestselling author, brings you inside the strategies behind turning vacation homes into profitable Lifestyle Assets. Hear the mistakes, breakthroughs, and strategies most STR investors never talk about, from the people actually doing it at the highest level.

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60 recent

November 11, 20261 hr 1 min

How To Charge 2x More & SELL OUT (Learn From JetBlue)

Want to learn more about Vodyssey or start your STR journey. Book a call here: https://api.leadconnectorhq.com/widget/bookings/vodyssey-strategy-session Check Out Our NEW Properties: 1) https://www.airbnb.com/rooms/1753123973094305646?guests=1&adults=1&s=67&unique_share_id=aea00426-c4bc-48a1-92a1-ee08601b806c&source_impression_id=p3_1794342693_P3Qed0yJagozG3mR 2) https://www.airbnb.ca/rooms/1790852910738764742?adults=6&check_in=2026-12-05&check_out=2026-12-12&children=4&search_mode=regular_search&source_impression_id=p3_e1cf1b0c-af11-4d88-9c4b-4e50fedda98b_11ec94c1-67e5-48ba-b992-d9074d18c883_0_1790852910738764742_1&previous_page_section_name=1000&federated_search_id=e1cf1b0c-af11-4d88-9c4b-4e50fedda98b WEBINAR LINK: https://shawnmoore.clickfunnels.com/optiniyvvg89s FOLLOW US: https://www.instagram.com/vodysseyshawnmoore https://www.facebook.com/vodysseyshawnmoore/ https://www.linkedin.com/company/str-financial-freedom https://www.tiktok.com/@vodysseyshawnmoore CONTACT US: support@vodyssey.com SOURCES: 1) https://news.airbnb.com/airbnb-q3-2026-financial-results 2) https://travel.yahoo.com/news/articles/jetblue-kid-free-flight-already-123055044.html 3) https://finance.yahoo.com/real-estate/article/there-are-more-than-two-condo-sellers-for-every-one-buyer-110000414.html?guccounter=1 4) https://www.ft.com/content/72abed21-6043-4b2b-81b1-f3a2547da5b7?syn-25a6b1a6=1

November 6, 202638 min

He WASTED 2 Years & $30K Before Making This One Change

Jarde’s Property: https://www.airbnb.com/rooms/1043656594301161070?source_impression_id=p3_1786469996_P3RW3y7RoEI7FxEF Want to learn more about Vodyssey or start your STR journey. Book a call here: https://api.leadconnectorhq.com/widget/bookings/vodyssey-strategy-session WEBINAR LINK: https://shawnmoore.clickfunnels.com/optiniyvvg89s FOLLOW US: https://www.instagram.com/vodysseyshawnmoore https://www.facebook.com/vodysseyshawnmoore/ https://www.linkedin.com/company/str-financial-freedom https://www.tiktok.com/@vodysseyshawnmoore CONTACT US: support@vodyssey.com Chapters 00:00 Jared’s path from manufacturing engineer to short-term rentals 03:04 Why the family chose Bloomington over California 09:01 Great guest reviews, but listing photos that failed to stand out 11:48 Why they upgraded property one before buying property two 18:02 Professional photography and the page-five problem 20:47 Pricing and cancellation changes push the listing to page one 26:57 Designing for Bloomington, not just football 32:58 When to judge the redesign and consider property two 35:55 Jared’s advice 39:00 Closing thoughts

November 4, 20261 hr 0 min

Hotels Invaded Airbnb - STR Owners Must Act NOW!!

Check out the properties: 1) https://www.airbnb.com/rooms/1806048588443177710?source_impression_id=p3_1793745068_P3-fsqsCzXZPdo9n 2) https://www.airbnb.com/rooms/1810452768791819984?source_impression_id=p3_1793745108_P3tpChwU9r-x_qGj Want to learn more about Vodyssey or start your STR journey. Book a call here: https://api.leadconnectorhq.com/widget/bookings/vodyssey-strategy-session FOLLOW US: https://www.instagram.com/vodysseyshawnmoore https://www.facebook.com/vodysseyshawnmoore/ https://www.linkedin.com/company/str-financial-freedom https://www.tiktok.com/@vodysseyshawnmoore CONTACT US: support@vodyssey.com Chapters 00:00 Intro 01:21 Two Shoutouts 07:18 Fed Rate Update 09:09 Holiday bookings RISE 17:44 MIDTERM RESULTS IMPACT 22:28 Hotels vs STRs 42:10 Small Investors .... Buy More? 49:41 VRBO's Negative Updates 54:02 Ski Season Need 2 Knows 57:47 Wrap Up SOURCES: 1) https://news.airbnb.com/introducing-a-new-way-to-book-stays-through-american-express-travel 2) https://www.airdna.co/blog/christmas-new-years 3) https://polymarket.com/finance/fed-rates 4) https://corporate.wyndhamhotels.com/news-releases/wyndham-rewards-opens-the-door-to-extraordinary-escapes-with-debut-of-homes-havens/ 5) https://finance.yahoo.com/real-estate/articles/small-investors-66-investor-home-165349823.html 6) https://www.luxehausstays.com/insights/vrbo-12-percent-commission/ 7) https://www.keydata.co/blog/2026-2027-ski-season-outlook-vacation-rental-pacing-trends

October 30, 202645 min

HORROR Story: How This "Perfect" STR Cost Him Big...

His Property: https://www.airbnb.com/rooms/931988051526866181?source_impression_id=p3_1792602174_P3QremAgIngP53ar Want to learn more about Vodyssey or start your STR journey. Book a call here: https://api.leadconnectorhq.com/widget/bookings/vodyssey-strategy-session WEBINAR LINK: https://shawnmoore.clickfunnels.com/optiniyvvg89s FOLLOW US: https://www.instagram.com/vodysseyshawnmoore https://www.facebook.com/vodysseyshawnmoore/ https://www.linkedin.com/company/str-financial-freedom https://www.tiktok.com/@vodysseyshawnmoore CONTACT US: support@vodyssey.com Chapters 00:00 Meet Jon Price 03:05 Why Bardstown 07:02 Turning a 1790s historic home into a luxury rental 09:33 Permits, parking rules, and setup 13:01 Financing, consultants, and property management 16:54 Five-star guest experience 20:51 Why autopilot pricing went wrong 24:08 Bourbon tourism growth 29:05 The regulation change 35:30 Reassessing pricing 42:12 Lessons from the journey

October 28, 20261 hr 1 min

The Best Way To Stay PROFITABLE During Slow Season - STR Secrets

Want to learn more about Vodyssey or start your STR journey. Book a call here: https://api.leadconnectorhq.com/widget/bookings/vodyssey-strategy-session FOLLOW US: https://www.instagram.com/vodysseyshawnmoore https://www.facebook.com/vodysseyshawnmoore/ https://www.linkedin.com/company/str-financial-freedom https://www.tiktok.com/@vodysseyshawnmoore CONTACT US: support@vodyssey.com SOURCES: 1) https://www.airdna.co/blog/airbnb-shoulder-season-tips 2) https://sites.google.com/vodyssey.com/contrarianstrinvestmentanalysi/full-page-embed 3) https://www.airbnb.com/rooms/1043656594301161070?source_impression_id=p3_1793206349_P3IAfAT3etnRSik_ 4) Chapters 00:00 Intro 03:10 Why Airbnb is limiting checkout chores 16:51 Josh’s response to Airbnb 23:37 Why Airbnb wants to protect its customer relationships 33:15 College-town game-day rentals 51:19 KEEP PROFITS DURING SLOW SEASON 56:15 Design upgrades around projected return on investment 01:00:25 Wrap-up and the hosts’ final challenge

October 23, 202642 min

At 65, She Vacations At Her STR & Revenue Rose 25% — Retirement Strategy

Her Property: https://www.airbnb.com/rooms/1629771906853968738?source_impression_id=p3_1785277620_P3p6Vg4WVc2ac0wG Want to learn more about Vodyssey or start your STR journey. Book a call here: https://api.leadconnectorhq.com/widget/bookings/vodyssey-strategy-session WEBINAR LINK: https://shawnmoore.clickfunnels.com/optiniyvvg89s FOLLOW US: https://www.instagram.com/vodysseyshawnmoore https://www.facebook.com/vodysseyshawnmoore/ https://www.linkedin.com/company/str-financial-freedom https://www.tiktok.com/@vodysseyshawnmoore CONTACT US: support@vodyssey.com Chapters: 00:00 — Meet Lisa: From CPA to STR Owner 08:20 — Buying Her First Vacation Rental 12:40 — Why She Chose a Smaller Property 14:15 — Designing the Property From Scratch 20:40 — Why She Hired a Co-Host 24:55 — Going Live… Then Hurricane Helene Hit 28:00 — How She Vacations at Her STR 31:00 — The Pet Strategy That Changed Her Bookings 33:35 — Her Revenue Is Up 25% 34:20 — Future Plans 36:10 — What She’d Tell Her Younger Self 38:00 — Wrap Up

October 21, 202659 min

The Revolt Started - People Are Done Getting F***** Over...

October 17, 202638 min

1st-Time Investors: 0 Debt, 0 Marketing, $26k Profit In 6 Months

Their Property: https://www.airbnb.com/rooms/1629771906853968738?source_impression_id=p3_1785277620_P3p6Vg4WVc2ac0wG Want to learn more about Vodyssey or start your STR journey. Book a call here: https://api.leadconnectorhq.com/widget/bookings/vodyssey-strategy-session WEBINAR LINK: https://shawnmoore.clickfunnels.com/optiniyvvg89s FOLLOW US: https://www.instagram.com/vodysseyshawnmoore https://www.facebook.com/vodysseyshawnmoore/ https://www.linkedin.com/company/str-financial-freedom https://www.tiktok.com/@vodysseyshawnmoore CONTACT US: support@vodyssey.com Chapters 00:00 Introduction and Guest Background 02:00 Deciding to Enter Short-Term Rental Market 03:59 Selecting the Location and Property Criteria 07:04 The Acquisition and Renovation Process 10:00 Design and Thematic Elements of the Property 13:03 Financials, Expenses, and Tax Benefits 18:00 Launching and Managing the Property 22:01 Performance, Bookings, and Revenue 27:59 Management, Guest Experience, and Future Plans 35:02 Lessons Learned and Advice for Investors

October 14, 20261 hr 0 min

High Earners BEWARE: You’re About to Feel the Squeeze…

Want to learn more about Vodyssey or start your STR journey. Book a call here: https://meetings.hubspot.com/vodysseystrategysession/booknow?utm_source=vodysseycom&uuid=80fb7859-b8f4-40d1-a31d-15a5caa687b7 WEBINAR LINK: https://shawnmoore.clickfunnels.com/optiniyvvg89s FOLLOW US: https://www.instagram.com/vodysseyshawnmoore https://www.facebook.com/vodysseyshawnmoore/ https://www.linkedin.com/company/str-financial-freedom https://www.tiktok.com/@vodysseyshawnmoore CONTACT US: support@vodyssey.com Sources: 1) https://finance.yahoo.com/economy/article/3-charts-sum-up-why-many-us-households-are-struggling-right-now-153911897.html 2) https://finance.yahoo.com/economy/article/even-high-earners-are-living-paycheck-to-paycheck-this-year-goldman-sachs-survey-100000235.html 3) https://finance.yahoo.com/news/top-10-earners-drive-nearly-191500198.html 4) https://www.airdna.co/blog/u.s.-review-september-2026 5) https://hello.pricelabs.co/athena/ 6) https://www.bookwithhaven.com/blog/vrbo-12-percent-commission Chapters 00:00 Intro 02:04 Current Economic Reports and Market Impact 03:55 Weather Events and Market Disruptions 05:49 Inflation Data and Federal Reserve Outlook 08:05 Real Estate Market Conditions and Opportunities 09:47 Platform Policy Changes and Parity Clauses 11:54 Verbo's New Rate Increases and Fee Structures 13:52 The Importance of Understanding Platform Terms of Service 16:01 The Role of AI in Revenue Management and Pricing 18:12 Risks of Over-Reliance on AI Tools 20:00 The Value of Regular Property Audits 22:04 Market Trends and Consumer Spending Patterns 23:57 Strategies for Property Optimization and Demand Capture 25:49 The Significance of Business Fundamentals and Financial Literacy 28:10 Insights from the September Air DNA Report 29:58 Supply, Demand, and Market Dynamics 32:08 The Impact of Interest Rates and Market Cycles 34:03 Adjusting Strategies in a K-Shaped Economy 35:57 The Risks of Blindly Following AI Recommendations 37:52 The Importance of Human Oversight in Revenue Management 40:07 The Need for Continuous Education and Market Awareness 42:06 High Income Earners and Financial Habits 44:09 Consumer Spending and Market Resilience 45:58 Opportunities in a Low Demand Market 47:50 The Power of Differentiation and Premium Offerings 49:47 The Role of Data and Market Analysis 52:07 Final Tips for Property Optimization 53:52 Conclusion and Key Takeaways

October 9, 202638 min

His Airbnb BEAT 4,000 Competitors - Uncovering His Strategy...

His Property: 1) https://www.airbnb.com/rooms/893594064461333412?source_impression_id=p3_1690219945_8pbrGEJ6b5Ox2ok0 Want to learn more about Vodyssey or start your STR journey. Book a call here: https://api.leadconnectorhq.com/widget/bookings/vodyssey-strategy-session WEBINAR LINK: https://shawnmoore.clickfunnels.com/optiniyvvg89s FOLLOW US: https://www.instagram.com/vodysseyshawnmoore https://www.facebook.com/vodysseyshawnmoore/ https://www.linkedin.com/company/str-financial-freedom https://www.tiktok.com/@vodysseyshawnmoore CONTACT US: support@vodyssey.com Chapters: 00:00:00 Intro 00:01:45 Family, Wyoming, and the Story Behind the Investor 00:04:45 From Life-Changing Challenges to Real Estate 00:05:50 Their First Rental Property—and Lessons Learned 00:07:45 Discovering Short-Term Rentals and the Scottsdale Market 00:10:00 Why They Chose Arizona 00:11:30 Cash Flow vs. Appreciation: What Matters Most? 00:13:00 The Mindset Shift Behind Their Investment Strategy 00:15:45 From Market Saturation to Opportunity 00:16:35 How Jordan Improved His Property’s Performance 00:18:00 Why Appealing to Everyone Can Hurt Your STR 00:19:30 The Power of Niche Positioning and Guest Experience 00:20:30 How to Stand Out and Win in a Crowded Market 00:22:00 Family Life and Building a Lifestyle Asset 00:24:00 Exploring Accessible Short-Term Rentals 00:27:00 What They Would Do Differently on Their First Deal 00:29:00 Balancing Investment Returns With Lifestyle Benefits 00:31:00 Building Wealth—and Creating Something for Your Family 00:33:00 Why Community and Mentorship Matter 00:36:00 Learning From Others and Continuing to Improve 00:37:00 Final Takeaways and Closing

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