The Short Term Show

Avery is joined by Lindsey Pleasant, founder of Hostie Vacation Rentals, to discuss how she built one of the largest short term rental management companies in rural Texas by focusing on exceptional hospitality and operational excellence. Lindsey shares how she grew from managing a single property to more than 80 luxury vacation rentals across Round Top and the surrounding area, explaining why cleanliness, high standards, and strong owner relationships have been the foundation of her success. They also explore the unique Round Top market, where antique shows, weddings, and city dwellers seeking a peaceful escape create steady demand despite relatively low occupancy rates, as well as why appreciation—not cash flow—is often the primary investment play. Along the way, Lindsey offers practical advice for aspiring property managers, emphasizing the importance of understanding your market, building a great team, and creating memorable guest experiences that keep visitors coming back. Connect with Lindsey: https://hostievacationrentals.com/ Connect with us: Get connected with a Short Term Shop agent: agents@theshorttermshop.com The Short Term Shop: https://theshorttermshop.com/ https://stsplus.com/ Follow Avery Carl on Instagram Follow Avery Carl on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

Avery is joined by Jeremy Udovich, founder of Sheboygan Vacation Rentals, to discuss how he went from a career in golf and software sales to building a thriving short-term rental portfolio and management company in Wisconsin. Jeremy shares how a single property near Lake Michigan grew into a portfolio of owned and managed vacation rentals, why Sheboygan’s beaches, golf courses, racetrack, and outdoor recreation create strong year-round demand, and how access to capital helped him scale quickly. He also explains why he waited years before leaving his W-2 job, the importance of education and preparation before taking on risk, and what he looks for when deciding whether to manage a property for another owner. The conversation offers valuable insight into scaling responsibly, building a management business organically, and finding overlooked opportunities outside of traditional vacation rental hotspots. Connect with Jeremy: www.sheboyganvacationrentals.com Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://stsplus.com/ Follow Avery Carl on Instagram Follow Avery Carl on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week's episode, Avery is joined by Chris McKenna, a former Fortune 500 executive who retired at 49 after building a portfolio of short-term rentals across Alabama, Oklahoma, and Maine. Chris shares how hearing Avery on a BiggerPockets podcast sparked his real estate journey, leading him from a demanding corporate career to owning multiple vacation rental properties that now generate nearly $1 million in annual revenue. He recounts the unforgettable challenges of his first investment property—including a renovation disaster that landed him in the emergency room with Bell’s palsy—and explains why staying focused on long-term goals helped him keep moving forward. Chris also discusses scaling a portfolio across multiple markets, transforming underperforming properties through strategic upgrades, and the lessons he learned from purchasing and revitalizing a lakeside cabin resort in rural Maine. How to connect with Chris: https://lawrenceslakesidecabins.com/https://vandellvacationrentals.com/gulfshores/ Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://stsplus.com/ Follow Avery Carl on Instagram Follow Avery Carl on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week's episode, Avery is joined by Aubrey Carlson, owner of Salt and Sky Lodging Company and a former military helicopter pilot, to talk about building a short-term rental portfolio in both San Diego and Birmingham, Alabama. Aubrey shares how she used a VA loan and a house-hack-style fixer strategy to break into an expensive coastal market, then expanded into Birmingham with BRRRR-friendly properties that could also perform as short-term and midterm rentals. She also breaks down how she partnered with investors early on—using detailed deal presentations at first, then evolving the structure to properly value rehab labor, design, and ongoing management. Finally, Aubrey emphasizes long-term thinking, choosing strong markets, and leveraging education and community to accelerate portfolio growth. How to connect with Aubrey: www.saltandskylodgingco.com https://www.instagram.com/saltandskylodgingco/ How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow Avery Carl on Instagram Follow Avery Carl on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon Production done by Outlier Audio

On this week’s episode, Avery is joined by Kenny Bedwell to break down what the short-term rental data actually says about the past few years and what investors should realistically expect heading into 2026. They discuss why the industry is experiencing stabilization rather than collapse, how average revenue declines are masking strong performance among top operators, and why treating short-term rentals like a professional business matters more than ever. Kenny explains the growing performance gap between average and top-tier properties, shares insights on financing mistakes and overleveraging, and outlines why focusing on being in the top 10% is the key to long-term success. The conversation wraps with Kenny’s outlook for 2026 and details on his upcoming STR Scale Summit for investors looking to thoughtfully scale their portfolios. How to connect with Kenny: strinsights.com How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow Avery Carl on Instagram Follow Avery Carl on TikTok Join the Short Term Shop Facebook group Check out the Short Term Shop on YouTube For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon Production done by Outlier Audio