The Short Term Show

On this week’s episode, Avery is joined by Cathy Craig, a top agent and investor in Broken Bow, Oklahoma, who shares an inside look at the current market and why now may be a prime time to buy. She explains how prices have come down significantly from peak levels while demand and occupancy remain strong, pushing back on the idea of “oversaturation” and emphasizing that the market continues to grow with infrastructure and tourism. Cathy also highlights what actually drives success in this market, focusing on guest experience, smart upgrades, and avoiding over-investing in unnecessary amenities. She wraps with real examples of high-performing properties and practical advice on buying right, adding value, and standing out without overspending. How to connect with Cathy: www.theshorttermshop.com How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram Follow us 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 Katie Johnson, a short-term rental attorney and investor who breaks down the most common legal mistakes hosts make and how to avoid them. She explains key risks like missing deed restrictions, improperly handling LLCs, and failing to secure adequate insurance, along with how to protect yourself from lawsuits tied to pools, amenities, and guest incidents. Katie also dives into service animals vs. emotional support animals, the legal realities of raising capital, and why setting up your business structure correctly from the start is critical. The conversation highlights how being proactive with legal strategy can save investors from costly mistakes down the road. How to connect with Katie: @strlaw.with.katiestrlaw.comkatiejohnsonplc.com How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram Follow us 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 Robert Warren, a real estate investor who shares how decades of experience in building, rehabbing, and developing led him to short-term rentals. He breaks down how he transitioned from long-term rentals and flips into STRs, including buying and optimizing properties in Gulf Shores and the Smokies for stronger cash flow and seasonality advantages. Robert also dives into creative deal-making, like using 1031 exchanges and value-add renovations to scale faster, while emphasizing the importance of buying right, avoiding over-leverage, and maximizing guest experience. He wraps with practical advice on investing mindset, building wealth through assets, and using time and skills to create equity early on. How to connect with Robert: detaildesign.biz How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram Follow us 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 John and Christina McNaught. The couple shares how they transitioned from long-term rentals into short-term rentals after realizing a small Airbnb unit on their property could cover their mortgage and generate additional cash flow. They discuss investing in the Bradenton, Florida market, including seasonality patterns, how being within about 15 minutes of the beach still works for guests, and why understanding the typical “family vacation” guest avatar is critical when designing a property. John and Christina also explain how strategic amenity upgrades like a game room, mini golf, playground, and pickleball court helped turn one property from about $95K in annual revenue into more than $217K. Connect with an agent: [email protected] How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram Follow us 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 David Taylor. David shares how he transitioned from construction and home inspecting into short term rental investing, ultimately choosing Branson, Missouri for its affordability and strong 10-month tourism season. He breaks down purchasing a brand-new three-bedroom condo for $225,000 and generating nearly $53,000 in gross revenue within his first partial year, highlighting why condos dominate the Branson market and why that can actually be an advantage for out-of-state investors. The conversation also covers financing non-warrantable condos, navigating vacation rental zoning, and why Branson is an ideal entry point for new investors who want solid returns without jumping into a half-million-dollar property. How to connect with David: www.theshorttermshop.com How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram Follow us 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 Celeste DiRocco and Philip Pane of Parklin Interiors. They share how they went from buying their first short term rental sight unseen in Gatlinburg to building a six property portfolio across Tennessee, North Carolina, Georgia, and Virginia while designing more than 200 short term rentals nationwide. Celeste explains how thoughtful, ROI focused design choices like strategic accent walls, updated lighting, elevated bedding, and strong exterior appeal can dramatically increase bookings without blowing the budget. They also discuss common investor mistakes, including overspending in the wrong areas, over cramming guest capacity, and going too over the top with themes that can hurt long term resale value. The conversation wraps with insights on enhancing the guest experience, building equity through smart renovations, and why focusing on the right doors instead of more doors can transform your investing strategy. How to connect with Celeste and Phillip: https://www.instagram.com/parklin_interiors/https://www.instagram.com/southern_serenity_stays/ https://parklininteriors.com/ How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram Follow us 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 Josh Briner. Josh shares how he transitioned from a background in education and flipping distressed properties into building a short term rental portfolio in upstate New York, including the Finger Lakes and Buffalo area. He dives into why he prefers value-add BRRRR deals over turnkey properties, how amenity stacking like pools and saunas can dramatically impact revenue, and what investors should realistically expect during the first year of launching a luxury rental. The conversation also covers scaling a management company to over 100 doors, navigating snow removal and winter challenges, and the mindset required to succeed long term in the hospitality-driven short term rental business. How to connect with Josh: https://www.facebook.com/share/1Cmpm7krpV/?mibextid=wwXIfr https://www.facebook.com/share/g/19kR6UzmSP/?mibextid=wwXIfr How to connect with Avery: The Short Term Shop - https://theshorttermshop.com/ Short Term Shop Plus - stsplus.com Follow us on Instagram Follow us 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 Matt Holmes of Get Up North Retreats to explore building a short-term rental business rooted in passion, relationships, and outdoor hospitality. Matt shares how his love of fishing, hunting, and family time led him to pivot from land and off-lake cabins into lakefront rentals—and ultimately into owning and operating a historic Minnesota campground. They discuss why understanding what guests actually want (like lake access), embracing seasonality, and betting on yourself can unlock opportunities even without massive capital. This episode is a powerful reminder that investing in places you truly believe in can create both strong returns and meaningful impact. How to connect with Matt: www.getupnorthretreats.com www.troutlakecampground.com https://www.facebook.com/profile.php?id=61566352371201 https://www.facebook.com/profile.php?id=61574524231835 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

On this week's episode, Avery is joined by Ross Alcorn, founder of Itinerary Boss, to break down how real estate investors can use credit card strategy to turn everyday spend into serious travel rewards or bottom-line value. Ross shares how his background in sales, real estate investing, and trip planning led him to uncover powerful points strategies—from welcome bonuses to transferable currencies—that most investors completely overlook. They dive into common mistakes like underutilizing Amex points, paying vendors via ACH without earning rewards, and leaving massive value on the table when furnishing or renovating properties. This episode is a practical crash course on leveraging credit cards smarter to fund travel freedom without increasing spending. How to connect with Ross: https://www.instagram.com/itineraryboss https://www.linkedin.com/in/rossalcornru/ https://open.spotify.com/show/1mmMJ6z3JdEOUJKUjLh8bD?si=a0e79b04f3084e68 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 Stacey St. John to dig into what’s really happening in today’s short-term rental market, with a particular focus on Myrtle Beach. They discuss how travel behavior has shifted toward more last-minute bookings, why pricing and revenue management matter more than ever, and how investors should think about buying opportunities in slower, more negotiable vacation markets. Stacey also shares her approach to scaling a property management portfolio, the importance of early bookings, and why tools like PriceLabs still require hands-on strategy. The conversation wraps with insights on growth goals, market seasonality, and opportunities for women looking to deepen their short-term rental education. How to connect with Stacey: https://staceystjohn.com/https://www.instagram.com/stacey_st.john/ https://www.linkedin.com/in/staceystjohn/ 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 Kira D’Annunzio to share how she built a highly successful Poconos short-term rental by leaning into branding, storytelling, and knowing her exact guest avatar. Kira walks through her journey from repeated career layoffs to financial independence through real estate, explaining how she used equity, off-market deals, and flexible rental strategies to scale her portfolio. They dive deep into why experience-driven properties outperform generic “luxury” listings, how her Bigfoot-themed cabin consistently earns five-star reviews without expensive amenities, and why targeting families and kids has been a massive competitive advantage. How to connect with Kira: airbnb.com/h/bigfootsnook 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 her husband Luke for a candid end-of-year wrap-up on what actually happened in short-term rentals and real estate in 2025—and what fundamentals will matter most going into 2026. They dig into why the market finally feels “boring” again (and why that’s a good thing), how low transaction volume means we’ve effectively been in a housing downturn for years, and why vacation markets feel cycles more intensely than primary-home markets. Avery and Luke also break down declining travel demand, the over-obsession with expensive amenities, and why long-term thinking, pricing discipline, and solid systems—not gimmicks—will win in the next phase of the cycle. How to connect with Avery and Luke: 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 Chuck Kramer to break down what it could mean if the Fed is truly winding down quantitative tightening and moving toward quantitative easing. They explain (in plain English) how increasing bank reserves and buying Treasuries/mortgage-backed securities can loosen credit conditions and potentially help bring borrowing costs down—without assuming we’ll ever see 3% mortgages again. Avery and Chuck also talk about why a “price crash” may already be reflected in low transaction volume since 2022, why vacation markets can feel the pain more than primary-home markets, and how a weaker dollar/stimulus chatter could impact discretionary travel demand going into 2026. 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 Joe Young, an Austin-based luxury short-term rental operator and co-founder of SPRKhost. Joe shares how he and his wife began with a Lake Travis vacation home in 2017 and ultimately turned their primary residence into a single property grossing nearly $500,000 a year. He breaks down how they expanded to managing 20+ high-end listings, the power of combining neighboring properties into mega-listings, and why Austin’s STR “crash” is really a market correction shaped by permitting, density rules, and growing competition. Joe also reveals his new venture, ExperiHaus, a TV-based guest-experience and revenue platform designed to help hosts elevate their brand and earn additional income. How to connect with Joe: https://sprkhost.com/https://experihaus.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

On this week's episode, Avery is joined by Naomi Brown, a commercial real estate agent and owner of the iconic Hanes Shoe House in York, Pennsylvania. She shares the wild backstory of the three-bedroom, shoe-shaped home that was originally built in 1950 as a marketing stunt for a local shoe store and how she transformed it from an ice cream shop into a short term rental grossing around $100,000 a year. Naomi and Avery dig into how to price truly one-of-a-kind properties, manage heavy maintenance on quirky builds, and use history, nostalgia, and souvenirs to create memorable guest experiences that drive five-star reviews. How to connect with Naomi: https://www.hainesshoehouse.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

On this week’s episode, Avery is joined by Jake Cohen, hospitality veteran and founder of Step by Step BNB. Jake grew up running a family bed and breakfast in Lake Tahoe, learned the art of pricing while managing boutique hotels, and eventually built a portfolio of short term rentals before launching his own revenue management company. He and Avery dig into why most investors overprice, how to shift your mindset from nightly rates to total revenue, and the biggest mistakes new hosts make with restrictions and minimum stays. Jake also walks through real data-driven pricing strategies using PriceLabs dashboards and shares his top lessons from nearly a decade in the industry. How to connect with Jake: https://www.stepbystepbnb.com/https://www.facebook.com/groups/priceyourstr 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 Brittany Magsig, the social worker turned short-term rental investor and content creator behind Mountain Mama Cabins. Brittany shares how motherhood, a pandemic trip to the Smoky Mountains, and a desire for freedom inspired her to pivot from education into real estate investing. She opens up about buying her first cabin in Wears Valley, navigating management challenges, and building a viral social media presence that now drives over 70% of her bookings directly. Avery and Brittany also discuss the myth of the “Airbnb bust,” staying adaptable in a saturated market, and how authenticity fuels both business and personal growth. How to connect with Brittany: mamacabins.com@mountainmamacabins - TikTok@mountainmamascabins - IGMountain Mama's Cabins - Facebook 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 Sandeep Nanda, one of the highest-volume Short Term Shop clients. Sandeep shares how he went from corporate revenue management to buying his first condo in downtown Austin, identifying the early opportunity in short term rentals, and scaling from one property to over thirty. He breaks down how data analysis, conviction, and a few bold power moves with lawyers and lenders led to multi-million-dollar exits—along with lessons about timing, asymmetric bets, and why “time kills deals.” Sandeep also discusses how he’s now applying those analytical skills to artificial intelligence through his new company, AI MySTR, helping hosts automate and optimize their businesses. How to connect with Sandeep: deepnanda.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

On this week's episode, Avery is joined by Bethany LaFlam, a “recovering attorney,” community architect, and author of The Power of OPE. Bethany and Avery dive into what it really means to stay in your lane, leveraging “other people’s everything” (money, time, assets, skills) so you can scale without burning out. They break down how to safely and legally use other people’s money in syndications, why true operators—not just capital raisers—are the ones who last, and the dangers of growing too fast without experience or infrastructure. Bethany also shares how transparent communication with investors during tough seasons can build trust, and how offloading work outside her lane transformed both her business and her life. How to connect with Bethany: http://bethanylaflam.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

On this week's episode, Avery is joined by Frank Napolitano. Frank shares how he and his family transitioned into short-term rentals in the Smokies, leveraging bonus depreciation and cost segregation to maximize tax advantages. He discusses what makes their property stand out—like a pool, tiki bar, and ADA accessibility—and how small touches such as holiday decorations and guest amenities have led to rave reviews. Frank also talks about navigating market saturation, negotiating during high-interest rate cycles, and his long-term goal of building a small portfolio, along with the lessons he’d give his younger self about money and investing early. How to connect with Frank: https://smokymountaincozycottage.com/https://www.facebook.com/p/Smoky-Mountain-Cozy-Cottage-61563198517049/ 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 Joe DelGrosso. Joe shares his journey from working in TV production to owning short-term rentals and why his first Smokies cabin proved that thoughtful refreshes can outperform flashy, high-cost amenities. He explains his boutique management approach at Southern Sons Hospitality, focusing on capped inventory, strong revenue management, and design upgrades that truly make properties stand out. Joe also offers advice for new operators, emphasizing the importance of running the numbers, staying focused, and building slowly with intention. How to connect with Joe: https://www.facebook.com/people/Southern-Sons-Hospitality/ 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 Thibault Masson, Head of Product Marketing at PriceLabs. They unpack Booking.com’s challenges in the U.S. versus Europe and how Airbnb’s fee changes are reshaping the playing field, before diving into PriceLabs updates like Dynamic Minimum Stay, the new Listing Optimizer, and a free revenue-management course. Avery also spotlights Market Dashboards for comp sets, cleaning-fee benchmarking, and smarter buy-box analysis, while Thibaut closes with data-driven advice for new investors. How to connect with Thibault: pricelabs.co 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 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

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