The Short Term Show

Join Joe DelGrosso, a former TV producer turned short-term rental mogul and owner of Southern Sons Hospitality, as he shares his groundbreaking insights on property refreshes that can double revenue. He reveals how a modest Smokies cabin outperformed luxury options and discusses his unique boutique management approach. Joe emphasizes the importance of meticulous revenue management, the need for stunning design upgrades, and strategic growth. Plus, he offers invaluable advice for aspiring rental operators on staying focused and financially savvy.

In this engaging discussion, Thibault Masson, Head of Product Marketing at PriceLabs and former Booking.com product lead, shares his insights into the vacation rental industry. He unpacks the contrasting success of Booking.com in Europe versus the U.S. and introduces fantastic PriceLabs features like Dynamic Minimum Stay and the Listing Optimizer. Thibault also highlights the value of Market Dashboards for competitive analysis and a free revenue-management course for hosts. He wraps up with practical tips for new investors to thrive in the market.

On this week’s episode, Avery is joined by Toni Boer. Toni shares how she and her husband turned a $200k family getaway into a cash-flowing STR, eventually building an eight-property portfolio along Kentucky’s Bourbon Trail plus a new Florida beach house. She opens up about losing a riverfront property to a historic flood, the hard lessons she learned about insurance, and how she used those setbacks to strengthen her investing strategy. Toni also discusses deal-finding in emerging markets, using the “enemy method” to outshine competition, and why patience and persistence still uncover strong STR opportunities.     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

On this week’s episode, Avery is joined by Tamara Brown. Tamara shares how she stumbled into real estate while caring for her grandparents, turning multiple family homes into rentals before purchasing her first STR in Destin, Florida. She explains how she analyzed her numbers, leaned on mentorship, and embraced the “enemy method” to size up competition. Tamara also talks through condo ownership fears, financing through a family sale, and why fear should never stop you from pursuing real estate opportunities.   How to connect with Tamara:  HELLOSUNSHINE.BIZ 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

On this week’s episode, Avery is joined by Amy Morehead. Amy shares how turning a family chalet in the Smokies into an STR during her mother’s Alzheimer’s caregiving season sparked a value-add strategy focused on “hot-mess” properties, smart renovations, and self-management. She explains why high-impact finishes beat flashy amenities for appraisal value and how she hunts deals with high days-on-market near the Smokies and along Kentucky’s Bourbon Trail. Amy also talks numbers, the refi-later mindset, and the education-plus-mentorship approach that helped her triple revenue after taking management in-house.   How to connect with Amy:  https://mapleleafpromise.com/https://strfixitpros.com/https://www.facebook.com/Strfixitpros/@STRFIXITPROS 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

In this conversation, Annie Lee, co-founder of Hello Host and a seasoned short-term rental operator, explains how their AI platform automates guest communications seamlessly. She shares insights on how the AI learns from past interactions, makes judgment calls on guest issues, and emphasizes the importance of maintaining a human touch in hosting. Annie also discusses the future of AI in the industry, practical tips for evaluating AI vendors, and her journey in the tech startup world, providing valuable advice for hosts looking to enhance their guest experience.

Karlton Dennis, a licensed enrolled agent and founder of Tax Alchemy, shares his expertise on real estate tax strategies for investors, focusing on short-term rentals. He explains material participation rules and how they impact audits. The discussion includes leveraging cost segregation and bonus depreciation to generate paper losses, misconceptions about hour-tracking, and the timing of acquisitions. Karlton also highlights common audit pitfalls and when investing in condos makes sense, providing valuable insights for savvy property owners.

On this week’s episode, Avery is joined by Andrew Llewellyn to unpack how he built a thriving short-term rental business in Louisville, KY. He shares the pivot from an almost-bakery to 10–30 guest stays, the data-driven playbook behind tiered calendar openings and last-minute pricing using throughput accounting, and why in-house cleaning and EOS/Traction keep operations tight. Andrew walks through converting an 18,000-sq-ft office into eight 4-bed/2-bath units (projected $800–$900k gross) after a first 10,000-sq-ft building that now grosses ~ $400k, plus the realities of SBA 504 financing (six–eight months and 40 bank conversations). Tech stack highlights include Guesty, PriceLabs (with manual event overrides), RemoteLock, and a heavy weekly metrics cadence.    How to connect with Andrew:  https://superstaysstr.com/https://andrewllewellyn.com/@iamandrewllewellyn 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 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

Brenna Carles, an expert in mortgage rates and the real estate market, shares her insights from leading Mortgage Shop. She discusses the impact of Powell's recent messaging on mortgage rates and what it means for investors. Brenna explains why lenders pre-price ahead of Fed meetings, and how economic indicators like the 10-year Treasury and inflation flow into rate sheets. She also highlights strategies for refinancing and using seller credits to create better financing options in today's market.

On this week's episode, Avery is joined by Jae Seok An, founder of Airbtics, to dig into smarter market selection and the realities of STR data. They walk through Airbtics’ draw-your-own-market mapping, listing density by bedroom count, and the Market Explorer—tools aimed at helping newer investors compare many locations, budgets, and regulation profiles quickly. Jae shares where the platform is headed (more granular property-level history, clearer “active listing” definitions, and global coverage) and offers practical takes on saturation, accuracy, and why your operations can double or triple revenue on the same property. He closes with advice to start with free analytics, research multiple markets, and then narrow to neighborhood-level decisions. How to connect with Jae: airbtics.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 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