The Short Term Show

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

On this week’s episode, Avery is joined by Annie Lee to dig into Hello Host, an AI “autopilot” for guest communications that plugs into PMS tools like Guesty, Hostaway, and Hospitable. They discuss how it learns from past conversations and listing data, makes judgment calls on escalations, and pings hosts when a human decision’s needed. Annie shares where AI is headed next, plus practical tips for choosing serious AI vendors and focusing your time on high-touch guest experience. They wrap with Annie’s founder journey, favorite resources, and why AI should augment—not replace—the human side of hosting.   How to connect with Annie: Hellohostai.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

On this week’s episode of The Short Term Show, Avery interviews Karlton Dennis. The two dig into how the short-term rental tax strategy actually works today, including what “material participation” really means in an audit. They cover using cost segregation and (current) bonus depreciation to create paper losses, the do’s and don’ts of hour-tracking, and smart Q4 timing for acquisitions. Karlton also shares pitfalls that trigger audits and when condos do (or don't) make sense.     How to connect with Karlton:  https://taxalchemy.com/https://www.instagram.com/taxalchemyadvisors/https://www.instagram.com/karltondennis/ 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

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

On this week’s episode of The Short Term Show, Avery interviews Brenna Carles. They unpack what Powell’s recent signaling means for mortgages, why lenders “pre-price” ahead of Fed meetings, and how the 10-year Treasury, inflation, jobless claims, and non-farm payrolls flow through to rate sheets. Brenna shares where DSCR and conventional rates are landing now, why refis are penciling again (including cash-out options), and tactical ways to use seller credits to buy down rates.   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

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

On this week’s episode, Avery is joined by Rashmi Bhat. Rashmi shares how she went from opening a restaurant at 21 to falling in love with Airbnbs, quickly building a multi‑market STR portfolio and scaling management in the Texas Hill Country to dozens of units through systems and a VA team. She and Avery dig into why the Hill Country still has room for standout properties—and the realities (like taxes) investors should underwrite—plus how keeping a W‑2 can be a strategic “fortress” while you grow cash‑flowing assets.    How to connect with Rashmi: Toasty Indian on socials   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

On this week's episode, Avery is joined by Wayde Hall from the Short Term Shop for a hands-on walkthrough of how he uses Price Labs Market Dashboards to analyze properties in detail. Wayde demonstrates step-by-step how to filter for specific property types, review counts, and amenities, then sort by revenue to identify top performers and pinpoint areas for improvement. He shows how to spot seasonality trends, set realistic pricing expectations, and understand which amenities or policies impact booking rates. The episode is packed with actionable tips for both beginner and seasoned investors who want to get beyond surface-level data and make smarter STR decisions.   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

On this week's episode, Avery is joined by Wayde Hall, a Short Term Shop agent in the Smoky Mountains, to dive into how he uses Price Labs Market Dashboards for short-term rental analysis. Wayde explains how this tool offers highly granular data—like occupancy rates, cleaning fees, and guest capacity—allowing investors to spot performance patterns rather than relying on broad averages. They discuss strategies for comparing neighborhoods, filtering for top-performing properties, and avoiding costly mistakes caused by misleading data from other platforms. Wayde also shares his top tips for new users to avoid overwhelm and focus on the most impactful filters for smarter investment decisions. How to connect with Wayde: www.theshorttermshop.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

On this week’s episode, Avery is joined by Bobby Birch, a new investor who’s crushing it with his very first short-term rental in the Smoky Mountains. Bobby shares how he and his wife bought a one-bedroom cabin in late 2023—at the peak of interest rates—and still grossed $98K in their first ten and a half months. He breaks down how thoughtful amenities, great hospitality, and proactive guest service helped them earn 127 five-star reviews. Bobby also dives into how they used a 5/1 ARM refinance to slash their mortgage payment and offers advice for staying hands-on and scaling the right way.   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

On this week’s episode, Avery is joined by Adrienne Green, a real estate investor, former teacher, and full-time world traveler who built a self-sufficient short-term rental business with the help of virtual assistants and great systems. Adrienne shares how she went from house hacking her basement to building a portfolio of long- and short-term rentals in Myrtle Beach, including a seller-financed deal. She explains how strong SOPs, tech tools like Monday.com, and smart delegation allow her to manage properties remotely while slow-traveling the world with her husband and three kids.   How to connect with Adrienne:  https://adriennegreen.com/ https://www.instagram.com/arealgreen/ http://youtube.adriennegreen.com/ https://www.linkedin.com/in/adrienne-green-real-estate/ https://www.facebook.com/ARealGreen123   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

On this week’s episode, Avery is joined by Barbara Schreihans, founder of Your Tax Coach, to dive into the powerful intersection of real estate investing and tax strategy. Barbara shares her insights on how short-term and mid-term rentals can be leveraged strategically depending on your income year, explaining how to maximize the short-term rental loophole and when to pivot to mid-term rentals for efficiency. She also offers real-world audit-proofing tips, outlines common mistakes investors make with tax prep, and explains why choosing the right tax professional is just as important as picking the right property.    How to connect with Barbara: www.yourtaxcoach.com @yourtaxcoach on IG   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

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 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 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/ 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

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/ 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

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    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

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/ 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

On this week’s episode, Avery is joined by Brandon Hall and Nathan Sosa of Hall CPA to dive deep into the short-term rental tax loophole and how investors can legitimately use it to offset W2 and business income. They discuss the origins of the loophole, how to qualify through material participation tests, and what documentation is necessary to survive an IRS audit. The conversation also covers depreciation recapture, bonus depreciation updates, and common traps tax influencers don’t warn you about. Whether you’re an investor with one STR or 100, this is a must-listen for anyone trying to minimize taxes the right way.    How to connect with Brandon: https://www.linkedin.com/in/brandonhallcpa/https://www.facebook.com/realestatecpahttps://x.com/TheRECPAwww.therealestatecpa.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

On this week's episode, Avery is joined by Yonah Weiss, an expert on cost segregation and a favorite among real estate investors. They break down what a cost segregation study is, how it allows short-term rental owners to accelerate depreciation and save on taxes, and who qualifies to benefit from this strategy. Yonah explains how to navigate bonus depreciation, recapture tax, and 1031 exchanges, emphasizing the importance of having a real estate-focused CPA.    How to connect with Yonah: https://yonahweiss.madisonspecs.com/https://www.yonahweiss.com/https://www.instagram.com/yonahweiss/https://www.linkedin.com/in/cost-segregation-yonah-weiss/https://twitter.com/YonahWeiss   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