Wed Jul 16 2025

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 TheBayBreak.com   How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ www.strquestions.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 rental...