The Short Term Show

Margot Schmorak, CEO and co-founder of Hostfully, joins the show to discuss how property management software is evolving and what hosts should look for when choosing a PMS. She covers Hostfully's latest developments in home automation, damage protection, accounting, and AI-powered guest communication, including AI that can handle routine guest questions and flag issues that require a host's attention. Margot also shares why proper onboarding, configuration, and ongoing management are essential to getting the most out of any software platform, along with her advice for creating a better guest experience and growing a short-term rental business. Connect with Margot: Hostfully.com Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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 Christian Walston, an engineer and real estate investor who turned an accidental introduction to short term rentals into a successful investment in the Orlando market. Christian shares how he went from buying his first long term rental for just $33,000 to purchasing a seven-bedroom vacation rental near Disney, which has already exceeded its conservative first-year revenue projections. He breaks down the property's $700,000 purchase price, $75,000 in theming and game-room upgrades, and why he believes Orlando's reputation for oversaturation is overlooking the market's massive tourism demand. Christian also shares the wild story of a guest discovering a disconnected camera hidden in a bedroom, which temporarily led Airbnb to suspend his listing, and discusses what the experience taught him about documenting issues and having a strong support network. Connect with Christian: https://walstonwindsorhills.directstays.com/ Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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

Avery is joined by Ben Levy, co-founder and CEO of Localbird, to discuss how short term rental hosts can turn local experiences into an additional revenue stream. Ben shares how a frustrating vacation in Hawaii inspired him to build a concierge platform that makes everything from private chefs and massages to tours, transportation, and rentals easier for guests to discover and book. He explains how Local Bird partners with hosts through revenue sharing, integrates with property management software, and uses personalized, timely recommendations to help hosts capture more of their guests' spending while providing a better hospitality experience. Avery and Ben also discuss why premium properties have an especially strong opportunity to monetize experiences, how AI is making personalized concierge service scalable, and why responding quickly to guest requests can make a major difference in conversions. Connect with Ben: https://www.localbird.com/ https://www.localbird.com/pages/STR-experiences-2026  Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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

Avery is joined by Melissa Nash, founder of Passively Rich with Rentals, to discuss how she built a portfolio of 20 rental properties after starting with just a $15,000 investment. Melissa shares how she uses short-term rentals to make markets like Southern California work, including buying properties that need some attention, turning them into profitable vacation rentals, and even selling them as turnkey businesses. She also explains her “lazy investor” method, why she prioritizes systems and time freedom, and how knowing your target guest can be more valuable than simply trying to maximize the number of people a property sleeps. Avery and Melissa also dive into realistic investment expectations, the importance of understanding your goals, and why consistent “base hits” can build a stronger portfolio than chasing one huge deal. Connect with Melissa: https://www.passivelyrichwithrentals.com/ Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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

Avery is joined by Leslie Carbajal to explore three Arizona short-term rental markets: Sedona, Flagstaff, and Scottsdale. Leslie breaks down what makes Sedona such a compelling luxury market, including its iconic red rocks, strong tourism, limited pool inventory, and potential for higher revenue, while also explaining why Flagstaff offers a more affordable entry point with demand driven by skiing, hiking, and outdoor recreation. They compare the three markets based on price point, property type, amenities, regulations, and traveler demand, with Leslie emphasizing that there is an investment opportunity for nearly every budget. Leslie also shares her personal journey from Short Term Shop client to agent and how Avery's book completely changed her perspective on real estate investing. Connect with Leslie: leslie@theshorttermshop.com Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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

Avery is joined by Gian Pazzia, one of the founders of KBKG and a longtime expert in cost segregation, to break down how short term rental investors can use tax strategies to maximize depreciation deductions. Gian explains the difference between traditional depreciation and cost segregation, how the short term rental tax strategy can allow qualifying investors to use deductions against active income, and why properly tracking material participation hours is so important. They also discuss the limitations of real estate professional status, what investors should look for when choosing a CPA or cost segregation provider, and how tools like Track750Tax and CostSegregation.com can simplify the process Connect with Gian: kBKG.com https://www.costsegregation.com/  use code: track750STR at track750.tax Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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

Avery is joined by Mary Mueller, a first-time short term rental investor who shares how she and her husband went from feeling priced out of vacation rentals to purchasing and renovating an affordable cabin in the Smoky Mountains. Mary explains how balancing homeschooling, raising three young children, and navigating family health challenges didn't stop them from finding a value-add property, completing a major renovation, and launching a successful rental that has exceeded their early expectations. She discusses the importance of continuous learning, leaning on experienced mentors, and embracing the beginner mindset, while offering an honest look at the challenges of getting a property rent-ready, managing guests, and building confidence as a new investor. The conversation is an encouraging reminder that ordinary families can build long-term wealth through short term rentals with patience, education, and consistent action. Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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 Luke and Laura Hintermeister to share how their family's passion for renovation, hospitality, and outdoor adventure led them to purchase and transform a vacation rental overlooking Lake Superior. The couple explains how years of researching the North Shore market, finding an overlooked value-add property with incredible views, and completing a major renovation themselves helped turn a dated two-bedroom home into a high-performing short term rental. They discuss why buying in a market you know can create a competitive advantage, the importance of focusing on irreplaceable features like location and views, and how involving their children in the renovation has laid the foundation for a family business. Luke and Laura also offer advice for new investors on overcoming the fear of getting started, continually learning the business, and building long-term wealth through thoughtful investing and hospitality. Connect with Luke and Laura: https://lagomescapes.hospitable.rentals Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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

Avery is joined by Courtney Petrovich, founder of Denori Designs, to explore how thoughtful design can dramatically improve the performance of short term rentals and boutique hotels. Courtney shares how she transitioned from long-term rental investing into hospitality design after doubling the annual revenue of her own North Myrtle Beach vacation rental, and explains why successful design starts with market research, guest psychology, and return on investment rather than personal taste. They discuss the importance of creating a strong sense of place, choosing amenities and furnishings that maximize revenue, and avoiding costly design mistakes that don't add long-term value. Courtney also offers practical advice on hiring the right designer, budgeting for renovations, and treating every design decision as an investment rather than an expense Connect with Courtney: Instagram: https://www.instagram.com/denoridesigns/ Website: https://www.denoridesigns.com/ Facebook: https://www.facebook.com/denoridesigns/ Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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

Avery is joined by Lucas Papageorgiou, a manufacturing consultant and real estate investor who shares how careful analysis, patience, and disciplined decision-making helped him build a portfolio of both long-term and short-term rentals. Lucas explains how purchasing a four-unit property at age 24 allowed him to live nearly rent-free while building equity, before expanding into the Smoky Mountains vacation rental market through methodical research and conservative financing. He also discusses why he refuses to chase rapid growth, emphasizing the importance of saving for down payments, resisting overleveraging, and viewing real estate as a long-term investment rather than a get-rich-quick strategy. Throughout the conversation, Lucas offers practical advice on avoiding analysis paralysis, trusting your own due diligence, and building wealth through consistency instead of shortcuts. Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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

Avery Carl is joined by Tim Grillot, real estate investor and former Short Term Shop agent who has built a successful vacation rental photography business. Tim shares how his passion for photography evolved into a full-time career, explains why professional photography is one of the highest-return investments a host can make, and offers practical advice for choosing a photographer who understands the unique goal of selling a vacation experience rather than simply documenting a property. He also discusses the importance of telling a property's story through photos, avoiding common listing mistakes, and building a business around work you genuinely enjoy. Connect with Tim: timgrillot.comscrollstopperphotography.comtim grillot photgraphy on FB and Instagram Connect with us: Get connected with a Short Term Shop agent: agents@theshorttermshop.com The Short Term Shop: https://theshorttermshop.com/ https://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

Avery is joined by Lindsey Pleasant, founder of Hostie Vacation Rentals, to discuss how she built one of the largest short term rental management companies in rural Texas by focusing on exceptional hospitality and operational excellence. Lindsey shares how she grew from managing a single property to more than 80 luxury vacation rentals across Round Top and the surrounding area, explaining why cleanliness, high standards, and strong owner relationships have been the foundation of her success. They also explore the unique Round Top market, where antique shows, weddings, and city dwellers seeking a peaceful escape create steady demand despite relatively low occupancy rates, as well as why appreciation—not cash flow—is often the primary investment play. Along the way, Lindsey offers practical advice for aspiring property managers, emphasizing the importance of understanding your market, building a great team, and creating memorable guest experiences that keep visitors coming back. Connect with Lindsey: https://hostievacationrentals.com/  Connect with us: Get connected with a Short Term Shop agent: agents@theshorttermshop.com The Short Term Shop: https://theshorttermshop.com/ https://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

Avery is joined by Yok to revisit the Blue Ridge, Georgia market and explain why it's one of the most overlooked opportunities for short-term rental investors. They discuss what continues to drive demand from Atlanta, Florida, and other nearby metro areas, why Blue Ridge offers less competition than the Smoky Mountains, and the types of cabins that perform best in today's market. Yok shares what buyers should prioritize—including mountain views, modernized interiors, and proximity to downtown Blue Ridge—while explaining why investors don't need over-the-top amenities to be successful. The episode also covers current pricing, the growing demand for waterfront properties, and why Blue Ridge remains an attractive option for both first-time and experienced STR investors. Connect with us: Get connected with a Short Term Shop agent: agents@theshorttermshop.com The Short Term Shop: https://theshorttermshop.com/ https://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

Avery is joined by Jeremy Udovich, founder of Sheboygan Vacation Rentals, to discuss how he went from a career in golf and software sales to building a thriving short-term rental portfolio and management company in Wisconsin. Jeremy shares how a single property near Lake Michigan grew into a portfolio of owned and managed vacation rentals, why Sheboygan's beaches, golf courses, racetrack, and outdoor recreation create strong year-round demand, and how access to capital helped him scale quickly. He also explains why he waited years before leaving his W-2 job, the importance of education and preparation before taking on risk, and what he looks for when deciding whether to manage a property for another owner. The conversation offers valuable insight into scaling responsibly, building a management business organically, and finding overlooked opportunities outside of traditional vacation rental hotspots. Connect with Jeremy: www.sheboyganvacationrentals.com Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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 Kelsey Ardoin to break down what's working right now in the Galveston and Crystal Beach short-term rental market. Using one of her own properties as a case study, Kelsey shares how investors can dramatically improve bookings without spending tens of thousands on major renovations, focusing instead on guest experience, outdoor entertainment spaces, hot tubs, and highly photographable amenities. She explains why large-group properties continue to perform well in this drive-to market, how to design beach houses that stand out from the competition, and why maximizing comfortable sleeping arrangements is critical to success. Avery and Kelsey also discuss current market conditions, why Crystal Beach remains one of the more affordable beach investment markets in the country, and how today's buyer-friendly environment compares to the frenzy of the COVID-era boom. Connect with Kelsey: agents@theshorttermshop.com Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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 Chris McKenna, a former Fortune 500 executive who retired at 49 after building a portfolio of short-term rentals across Alabama, Oklahoma, and Maine. Chris shares how hearing Avery on a BiggerPockets podcast sparked his real estate journey, leading him from a demanding corporate career to owning multiple vacation rental properties that now generate nearly $1 million in annual revenue. He recounts the unforgettable challenges of his first investment property—including a renovation disaster that landed him in the emergency room with Bell's palsy—and explains why staying focused on long-term goals helped him keep moving forward. Chris also discusses scaling a portfolio across multiple markets, transforming underperforming properties through strategic upgrades, and the lessons he learned from purchasing and revitalizing a lakeside cabin resort in rural Maine. How to connect with Chris: https://lawrenceslakesidecabins.com/https://vandellvacationrentals.com/gulfshores/ Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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 Lance Lalanne, a Louisiana-based business executive and real estate investor who transformed his family's dream of owning a beach condo into a successful short-term rental business. Lance shares how a conversation with a friend, Avery's audiobook, and guidance from the Short Term Shop team helped him confidently purchase a condo in Orange Beach, Alabama, negotiate a significant discount, and build a thriving rental from the ground up. They discuss the importance of buying based on numbers rather than emotion, leveraging coaching and community support, and creating a long-term wealth-building plan through strategic real estate investing. Along the way, Lance shares lessons from his first year as an STR owner and why he's already planning property number two. Connect with Lance: LeiLani321.com Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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

Avery Carl sits down with Erica and Jon Larson, a former teacher and a VP of sales who turned a career shake-up into a thriving short‑term rental business. They share the real, often messy process of leaving their W‑2 jobs—starting with a tight budget, learning the hard way why you never skip a home inspection, and the nightmare of trusting a realtor who wasn't an STR expert. From teaching kindergarteners to managing guest messages mid‑class, Erica and Jon walk through the grit, risk, and persistence it took to buy their first Smoky Mountains property in 2022 and eventually replace one full‑time income. This conversation is packed with candid lessons for anyone dreaming of trading a traditional job for property‑based freedom. Connect with Erica and Jon:  Website: CYLPrentals.com Instagram: https://www.instagram.com/changeyourlatitudeproperties/ Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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

Avery is joined by Short Term Shop agent Stacey Lancaster to explore the current state of short-term rental investing across Texas Hill Country and the Austin area. Stacey explains why the market currently favors investors who are willing to negotiate, create memorable guest experiences, and look beyond turnkey properties to add value through design and management. They also discuss how continued population growth in Texas, future developments like Fredericksburg's incoming Waldorf Astoria, and shifting market conditions could shape demand in the years ahead. Connect with an agent: agents@theshorttermshop.com Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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

Avery Carl is joined by Short Term Shop agent Cody Roberts to break down why Southern Utah has become an increasingly attractive short-term rental market. They discuss the tourism demand driven by Zion National Park and the surrounding outdoor attractions, the strict permit regulations that help prevent oversaturation, and the types of properties that perform best in the market. The conversation also covers the benefits of condos and townhomes with resort-style amenities, the appeal of purpose-built short term rental communities, and why investors need to understand local regulations before buying in areas like St. George and Hurricane. Connect with an agent: agents@theshorttermshop.com Connect with us: The Short Term Shop - https://theshorttermshop.com/ https://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 Ana Klein, CEO of Tax Boss, to break down how short term rental tax law can help high income earners significantly reduce their taxable income. Ana explains how strategies like cost segregation and bonus depreciation can create large paper losses that offset W2 income, while emphasizing that these benefits only work when paired with strong investments and long term planning. The conversation dives into common misconceptions, including year-one benefits, depreciation recapture, and why trying to game real estate professional status can backfire. They also highlight the importance of proper bookkeeping, time tracking for material participation, and working with qualified professionals to avoid costly IRS audits and mistakes. How to connect with Ana: https://www.instagram.com/taxbossana/ 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 Dohn Thornton, a seasoned real estate investor and short sale expert who has flipped over 3,000 properties and now focuses on advanced asset protection strategies. Dohn breaks down the concept of a spendthrift trust, explaining how it differs from traditional LLCs and trusts by offering greater privacy, lawsuit protection, and potential tax advantages through a contract law structure. The conversation dives into how these trusts can shield assets from discovery, avoid triggering taxable events, and fundamentally change how investors think about income, expenses, and wealth management. Dohn also shares real world examples from his own business, including how switching to this structure deterred lawsuits entirely and reshaped his approach to investing and long-term wealth building. How to connect with Dohn: https://bensonfinancial.us  Instagram: @dohnthornton 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 Emily Tunggala. Emily shares how Hospitable is expanding beyond traditional property management software by launching a marketplace that connects property managers with owners looking for help. She explains how the platform uses performance data and insights to match the right managers with the right properties, while also giving newer managers tools to onboard clients professionally. The conversation highlights how this could change the way managers find clients, reduce time spent chasing leads, and create more opportunity based on results rather than connections. How to connect with Emily:  https://hospitable.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 Brian Boyd. Brian, a tax attorney and real estate investor, breaks down how the short term rental tax strategy works, explaining how investors can use cost segregation and bonus depreciation to offset active income while building wealth. He emphasizes the importance of self-managing properties, tracking time accurately, and understanding the rules to properly qualify for these tax benefits. The conversation also dives into common mistakes investors make, like overspending on furnishings or prioritizing tax savings over cash flow, and highlights how real estate can be a powerful long-term wealth-building tool when approached strategically. How to connect with Brian: YouTube: @yourtaxlawyerInstagram: briantboydTikTok: @briantboydFacebook: Brian T Boyd 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 Kim Fitzpatrick. Kim shares how she went from being a PE teacher and single mom to launching her first Airbnb with an air mattress, eventually scaling into multiple investment properties across markets like the Smokies and Montana. She breaks down how her hands-on experience renovating and setting up properties led to founding Launched Host, a service that helps investors go from empty to guest-ready in just seven days. The conversation also highlights the realities of launching short term rentals, the importance of systems and guest experience, and how simplifying setups can reduce stress and improve long-term success. How to connect with Kim: Launchedhost.com https://www.instagram.com/launchedhost?igsh=dnNhYXpjbGZsbHBm&utm_source=qr https://www.facebook.com/share/1K5wTTDLjP/?mibextid=LQQJ4d 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 Ari Rastagar. Ari shares how he built a multibillion-dollar real estate firm starting with just $3,500 and explains why real estate is far more operationally complex than most beginners expect. He dives into the importance of risk management, due diligence, and local market expertise, highlighting common mistakes investors make—especially when relying too heavily on spreadsheets instead of real-world context. The conversation also explores why short term rentals require an intense focus on customer experience and operations, and how scaling systems and processes is key to long-term success. How to connect with Ari: Website: https://rastegarcapital.com/ LinkedIn: https://www.linkedin.com/in/arirastegar/ Instagram: https://www.instagram.com/rastegar TikTok: https://www.tiktok.com/@arirastegar 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 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: agents@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 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 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