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

Author: Shawn Moore

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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.

425 Episodes
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Their 1% Property: https://www.airbnb.com/rooms/1608127384681815294?source_impression_id=p3_1794522435_P38yfcv25GQDN9r1 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: [email protected]
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: [email protected] 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
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: [email protected] 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
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: [email protected] 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
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: [email protected] 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
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