The Short Term Show

On this week’s episode, Avery is joined by Chad Gallagher, a tech-turned-real-estate entrepreneur who’s built and sold a 5,000-door property management company, owns over 200 long-term rentals, and now focuses on acquiring what he calls "iconic" short-term rental properties. Chad shares the details behind his high-end STR portfolio—including a 9-bedroom Chesapeake Bay estate and a 400-acre working winery—while diving into his unique acquisition strategies through tax sales, distressed assets, and off-market deals. He also explains why branding, adding bedrooms, and leveraging complexity are his keys to long-term success.   How to connect with Chad: RealEstateHackers.com [RealEstateHackers.com] TheBayBreak.com [TheBayBreak.com]   How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ [https://theshorttermshop.com/] www.strquestions.com [http://www.strquestions.com] Follow Avery Carl on Instagram [https://www.instagram.com/theaverycarl] Follow Avery Carl on TikTok [https://www.tiktok.com/@averyacarl] Join the Short Term Shop Facebook group [https://www.facebook.com/groups/1462601024089587] Check out the Short Term Shop on YouTube [https://www.youtube.com/c/TheShortTermShop]   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon [https://www.amazon.com/Short-Term-Rental-Strategy-Out-Hosting-Competition/dp/1960178709] Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon [https://amzn.to/3Adg6PA]

On this week's episode, Avery is joined by Jane Ng, a Bay Area-based investor who pivoted into real estate after her daughter's health challenges made traditional work unsustainable. Jane shares how she grew her portfolio to include long-term rentals in Arkansas, four profitable short-term rentals in California, and ten co-hosted properties—all while raising three kids. She dives into her strategy for selecting overlooked markets, leveraging conventional financing, and using short-term rentals to unlock time freedom for parents. Her story is a powerful reminder of how real estate can transform lives beyond just finances.   How to connect with Jane:  @theinvestingmom on IG   How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ [https://theshorttermshop.com/] www.strquestions.com [http://www.strquestions.com] Follow Avery Carl on Instagram [https://www.instagram.com/theaverycarl] Follow Avery Carl on TikTok [https://www.tiktok.com/@averyacarl] Join the Short Term Shop Facebook group [https://www.facebook.com/groups/1462601024089587] Check out the Short Term Shop on YouTube [https://www.youtube.com/c/TheShortTermShop]   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon [https://www.amazon.com/Short-Term-Rental-Strategy-Out-Hosting-Competition/dp/1960178709] Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon [https://amzn.to/3Adg6PA]

On this week’s episode, Avery is joined by Michael Chang, a seasoned short-term rental investor who manages 38 properties across Philadelphia, the Smoky Mountains, and the Catskills using both ownership and arbitrage strategies. Michael shares how he's scaled efficiently by leveraging technology like HelloHost.ai and VA teams, and why differentiation and guest experience are critical to success in today’s competitive landscape. He dives into the importance of investing in quality properties and intentional amenities, while also discussing how market dynamics are evolving in both metro and vacation markets.   How to connect with Michael:  @michaelchangbnb How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ [https://theshorttermshop.com/] www.strquestions.com [http://www.strquestions.com] Follow Avery Carl on Instagram [https://www.instagram.com/theaverycarl] Follow Avery Carl on TikTok [https://www.tiktok.com/@averyacarl] Join the Short Term Shop Facebook group [https://www.facebook.com/groups/1462601024089587] Check out the Short Term Shop on YouTube [https://www.youtube.com/c/TheShortTermShop]   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon [https://www.amazon.com/Short-Term-Rental-Strategy-Out-Hosting-Competition/dp/1960178709] Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon [https://amzn.to/3Adg6PA]

On this week's episode, Avery is joined by Tammy Gibbons, who shares how she and her husband transformed their 120-acre Wisconsin family farm into a thriving short-term rental business through a 1031 exchange. Tammy discusses how they landed on Panama City Beach as their market, the decision to self-manage while balancing full-time careers and parenting, and why condos—despite the stigma—ended up being the right investment. She also dives into how systems, communication, and intentional habits have helped her stand out and succeed, grossing $200K annually from two beachfront condos.    How to connect with Tammy: www.enjoytheviewstr.com [http://www.enjoytheviewstr.com]    How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ [https://theshorttermshop.com/] www.strquestions.com [http://www.strquestions.com] Follow Avery Carl on Instagram [https://www.instagram.com/theaverycarl] Follow Avery Carl on TikTok [https://www.tiktok.com/@averyacarl] Join the Short Term Shop Facebook group [https://www.facebook.com/groups/1462601024089587] Check out the Short Term Shop on YouTube [https://www.youtube.com/c/TheShortTermShop]   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon [https://www.amazon.com/Short-Term-Rental-Strategy-Out-Hosting-Competition/dp/1960178709] Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon [https://amzn.to/3Adg6PA]

On this week’s episode, Avery is joined by Taylor Jolly, founder of Roam Free Vacation Home Rentals, to discuss how he transitioned from construction project management to profitable real estate investing. Taylor shares how he’s made co-living and large short-term rentals cash flow in expensive markets like Austin, leveraging creative strategies like hard money loans and wholesaler deals. He also explains how his hospitality-focused brand Roam Free helps other investors find, design, and manage standout STRs in the Texas Hill Country. From poker sheds to above-ground pools, Taylor’s story is a great reminder that there’s more than one way to win in real estate.    How to connect with Taylor: https://roamfreevhr.com/ https://www.instagram.com/roamfreevhr/ How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ [https://theshorttermshop.com/] www.strquestions.com [http://www.strquestions.com] Follow Avery Carl on Instagram [https://www.instagram.com/theaverycarl] Follow Avery Carl on TikTok [https://www.tiktok.com/@averyacarl] Join the Short Term Shop Facebook group [https://www.facebook.com/groups/1462601024089587] Check out the Short Term Shop on YouTube [https://www.youtube.com/c/TheShortTermShop]   For more information on how to get into short term rentals, read Avery’s books: Smarter Short Term Rentals - Buy it on Amazon [https://www.amazon.com/Short-Term-Rental-Strategy-Out-Hosting-Competition/dp/1960178709] Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon [https://amzn.to/3Adg6PA]