The Short Term Show

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

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

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

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

How to connect wit...

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

Ho...

On this week’s episode, Avery is joined by Chad Gallagher, a tech-turned-real-estate entrepreneur who’s built and sold a 5,000-door property management company, owns over 200 long-term rentals, and now focuses on acquiring what he calls "iconic" short-term rental properties. Chad shares the details behind his high-end STR portfolio—including a 9-bedroom Chesapeake Bay estate and a 400-acre working winery—while diving into his unique acquisition strategies through tax sales, distressed assets, and off-market deals. He also explains why branding, adding bedrooms, and leveraging complexity are his keys to long-term success.

How to connect with Chad:

On this week's episode, Avery is joined by Jane Ng, a Bay Area-based investor who pivoted into real estate after her daughter's health challenges made traditional work unsustainable. Jane shares how she grew her portfolio to include long-term rentals in Arkansas, four profitable short-term rentals in California, and ten co-hosted properties—all while raising three kids. She dives into her strategy for selecting overlooked markets, leveraging conventional financing, and using short-term rentals to unlock time freedom for parents. Her story is a powerful reminder of how real estate can transform lives beyond just finances.

How to...

On this week’s episode, Avery is joined by Michael Chang, a seasoned short-term rental investor who manages 38 properties across Philadelphia, the Smoky Mountains, and the Catskills using both ownership and arbitrage strategies. Michael shares how he's scaled efficiently by leveraging technology like HelloHost.ai and VA teams, and why differentiation and guest experience are critical to success in today’s competitive landscape. He dives into the importance of investing in quality properties and intentional amenities, while also discussing how market dynamics are evolving in both metro and vacation markets.

How to connect with Michael: 

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On this week's episode, Avery is joined by Tammy Gibbons, who shares how she and her husband transformed their 120-acre Wisconsin family farm into a thriving short-term rental business through a 1031 exchange. Tammy discusses how they landed on Panama City Beach as their market, the decision to self-manage while balancing full-time careers and parenting, and why condos—despite the stigma—ended up being the right investment. She also dives into how systems, communication, and intentional habits have helped her stand out and succeed, grossing $200K annually from two beachfront condos. 

How to connect with Tammy:

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On this week’s episode, Avery is joined by Taylor Jolly, founder of Roam Free Vacation Home Rentals, to discuss how he transitioned from construction project management to profitable real estate investing. Taylor shares how he’s made co-living and large short-term rentals cash flow in expensive markets like Austin, leveraging creative strategies like hard money loans and wholesaler deals. He also explains how his hospitality-focused brand Roam Free helps other investors find, design, and manage standout STRs in the Texas Hill Country. From poker sheds to above-ground pools, Taylor’s story is a great reminder that there’s more tha...

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

On this week's episode, Avery is joined by Yonah Weiss, an expert on cost segregation and a favorite among real estate investors. They break down what a cost segregation study is, how it allows short-term rental owners to accelerate depreciation and save on taxes, and who qualifies to benefit from this strategy. Yonah explains how to navigate bonus depreciation, recapture tax, and 1031 exchanges, emphasizing the importance of having a real estate-focused CPA. 

How to connect with Yonah:

https://yonahweiss.madisonspecs.com/
https://www.yonahweiss.com/
https://www.instagram.com/yonahweiss/
ht...

On this week's episode, Avery is joined by Heather Meuer, a Missouri-based real estate investor who transitioned from running an auto parts business to building and managing RV parks and glamping resorts. Heather shares how she and her husband turned an abandoned campground into a thriving $7.8M resort in Branson, complete with glamping tents, RV pads, a coffee shop, and pizza kitchen—all designed to elevate the guest experience. She walks through the challenges of securing an SBA loan, tips for working with your spouse, and how creating multiple revenue streams can supercharge a hospitality business. 

 How to c...

On this week's episode, Avery is joined by Melissa and Chris Jones, a dynamic investor duo who share how a simple desire for a second home evolved into a thriving short-term rental business and boutique co-hosting company. They walk through their journey from renovating a “turnkey” townhome in Galveston to scaling up with high-performing properties in Broken Bow and Orange Beach. Along the way, they highlight their design strategies, how they stand out in saturated markets, and how word-of-mouth helped them grow a co-hosting portfolio of 25+ properties. Melissa and Chris also offer heartfelt advice for aspiring hosts and share the...

On this week’s episode, Avery is joined by Nathan St. Cyr, a hospitality innovator who’s redefining budget travel through upscale hostels. Nathan shares how he stumbled into the hostel space in Maui and turned a $821K property into a $5.2M valuation in just 18 months—all while achieving over $824K in annual NOI. He breaks down the operational and financial advantages of hostel investing, how he optimized guest experience for Gen Z travelers, and why U.S. hostel development is a wide-open market opportunity. Nathan also shares insights on zoning, daily guest programming, and his strategy for scaling across...

On this week’s episode, Avery is joined by Isaac French, a creative powerhouse who went from bookkeeper to hospitality developer and Instagram sensation. Isaac shares the remarkable journey behind Live Oak Lake, a Nordic-inspired micro resort he designed and built from scratch in Texas—achieving 95% occupancy in year one and ultimately selling to an institutional buyer for $1 million per key. He discusses the challenges of construction, overcoming an Airbnb suspension, and the science behind direct bookings and social media growth. Isaac also dives deep into experience-driven design, micro resort feasibility, and the power of storytelling in creating unforgettable gues...

On this week's episode, Avery is joined by Matt Krueger. Matt shares his journey from working dead-end jobs to becoming a full-time real estate investor with a portfolio of 11 properties across Iowa. He dives into his strategies for blending long-term and short-term rentals, financing deals creatively with home equity lines of credit, and how local market knowledge has been the key to his short-term rental success—despite data platforms showing low market scores. Matt also emphasizes the importance of sacrifice, perseverance, and strategic risk-taking in building long-term wealth through real estate.

How to connect with Mat...

On this week's episode, Avery is joined by Portia Louder, a former real estate investor who served five years in federal prison for mortgage fraud. Portia shares the gripping story of how she transitioned from a hardworking photographer and mom to being deeply involved in high-risk real estate deals that spiraled into illegal territory. She offers powerful insight into how easily these “gray area” deals can turn into life-altering legal troubles, and emphasizes the importance of integrity and doing business the right way. Her journey of redemption serves as both a cautionary tale and an inspiring reminder that it’s neve...

On this week's episode, Avery is joined by commercial real estate attorney Carrie Risatti to dissect some of the most common real estate “hacks” that could land investors in serious legal trouble. Carrie breaks down what qualifies as mortgage fraud, how easily it can happen, and the federal consequences that follow. The two dive into gray and red area tactics like occupancy fraud, subject-to financing, multiple vacation loans, and cash-back side agreements—giving listeners clarity on what’s legal and what could trigger a visit from the FBI.

How to connect with Avery:

The Short...

On this week's episode, Avery is joined by Jeff Brown of IntelliHost, who shares his journey from corporate data analytics to launching a cutting-edge short-term rental software. Jeff explains how his experience with specializing in ultra-themed properties led to the creation of IntelliHost—a tool designed to help Airbnb hosts optimize their listings and maximize revenue. He discusses the power of data-driven decision-making in STR investments, the challenges of ultra-themed rentals, and how pricing strategies influence Airbnb rankings. Jeff also gives valuable advice for new investors on how to strategically launch a listing for long-term success.

H...

On this week's episode, Avery is joined by Paul Graham, an experienced investor with a background in commercial real estate who has transitioned into short-term rentals. Paul shares insights on the importance of bringing joy into real estate investments, discussing how his properties not only generate cash flow but also create memorable experiences for both guests and his own family. He breaks down the financial and emotional benefits of his short-term rental in Canyon Lake, Texas, explaining how he partnered with his parents to finance the deal. Paul also dives into the key differences between underwriting commercial and short-term...

On this week's episode, Avery is joined by muralist Dave Blanche, the founder of BlestDesign, to discuss the impact of murals on short term rental properties. Dave shares his journey from graffiti and canvas work to large-scale murals, detailing how he broke into the Airbnb market. He explains how murals enhance guest experiences, improve booking rates, and even influence resale value. Avery and Dave also discuss the importance of hiring skilled artists, avoiding cheap work, and how the right mural can serve as a unique marketing tool for short-term rentals.

How to connect with Dave:

On this week's episode of The Short Term Show, Avery is joined by Ashley Freeman, a former tennis pro turned short-term rental powerhouse. Ashley shares how she transitioned from teaching tennis to managing over 100 properties in a college town, leveraging local knowledge and relationships for success. She dives into the pros and cons of investing in college town rentals, how her athletic background shaped her business mindset, and why adaptability and competitive edge are key in the short-term rental industry. 

How to connect with Ashley:

@Velvet_ditch_villas on Instagram

H...

On this week's episode of The Short Term Show, Avery is joined by Kate Almeda, a seasoned Airbnb host and short-term rental expert. Kate shares her journey from managing concerts and working on the Vans Warped Tour to building a career in short-term rentals, including her experience with home-sharing, managing unique stays like surf shacks, and working as a host advisor at Airbnb. She also discusses best practices for new hosts, the evolution of the short-term rental industry, and how regulations have shaped her business strategy. 

How to connect with Kate: 

hostwithkate.com

In this episode of The Short Term Show, Avery welcomes Cynthia and Chris Hanson, a couple based in Mesa, Arizona, who currently own and manage three properties. Cynthia shares her background in hospitality management and how that has helped make the transition into STRs more seamless. They also share the story of how they chose their properties in each market and where they're looking to expand next. 

How to connect with Cynthia and Chris:

https://pictureperfect.staydirectly.com/

How to connect with Avery:

The Short Term Shop - h...

In this episode of The Short Term Show, Avery is welcoming back Rich Somers! Rich highlighted the unique opportunities available in 2025, particularly due to the current supply and demand dynamics in the housing market. He pointed out that while many are waiting for interest rates to drop, experienced investors are still actively buying properties, recognizing the potential for future appreciation. Rich also shared his thoughts on the significance of patience in real estate and the importance of surrounding oneself with the right people.

Check out our previous episodes with Rich!: 

Marrying Multifamily and STR...

In today's episode, Avery and Chuck dive into some current events in the short term rental space and discuss how the second Trump administration could impact the real estate industry. We also touched on how international travel patterns and population migration within the country could impact various markets. We both stress that while there are challenges ahead, there are also opportunities for those who can navigate the current market conditions.

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/

www.strquestions.com

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In this episode of The Short Term Show, we dive into the recent policy changes from Vrbo regarding the sale of vacation rental properties. As we discuss the implications of these new rules, Avery is joined by experienced agents from The Short Term Shop: Natalie Walthour, Jay Lawrence, and Stacey Lancaster. We start by highlighting the key points of Vrbo's new policy, which requires sellers to block their calendars and notify travelers of upcoming reservations when listing their properties for sale. We touch on the complexities of transferring future bookings to new owners, including the legal obligations that may a...

In this episode of the Short Term Show, Avery welcomes Jefferson Calloway. Jefferson shares his journey into real estate, starting from his time as a helicopter pilot in the military stationed in Alabama, where he purchased his first rental property. He discusses his transition back to the East Coast and his focus on home remodeling, highlighting the synergy between real estate and home improvement. Avery and Jefferson also discuss why being likeable and easy to work with are important qualities to have in real estate, and how househacking and creative financing can significantly contribute to the growth of your p...

In this episode of The Short Term Show, Avery introduces Gil Chan, a real estate investor who has recently launched an innovative platform for direct bookings called Crafted Stays. Gil explains the importance of having a direct booking presence and how Crafted Stays offers a user-friendly, affordable solution for hosts. We also discuss the potential impact of Google Vacation Rentals and the benefits of starting direct bookings early. Gil shares insights into his own direct booking success, emphasizing the value of email marketing and nurturing past guests.

How to connect with Gil: 

https://www...

In this episode of the Short Term Show, Avery and her guest, experienced vacation rental investor, Chuck Kramer, dove into the latest lists of best places to invest in vacation rentals, released by various data and management companies. They aimed provided insight on various lists while providing clarity on how to interpret the markets included in the lists. Throughout the episode, they stressed the importance of market knowledge, understanding guest demographics, and doing thorough research beyond just the data provided in these lists. They also discussed the potential impact of social media and new developments on vacation rental markets.

In this episode of the Short Term Show, Avery welcomed Austin, Texas based real estate investor Vivian Yip. Vivian shared her story of feeling trapped in the corporate rat race, which caused her to explore house flipping alongside her husband but soon realized it was akin to another job. Inspired by the book "Tax-Free Wealth," Vivian pivoted her strategy towards owning real estate for long term wealth building. Avery and Vivian delved into the strategies for managing midterm rentals, and the importance of having a good property management system. Vivian also shared insights on attracting a diverse range of g...

In this episode of the Short Term Show, Avery welcomed Chris and Jena Hartman, a dynamic duo who are both pilots and successful real estate investors. Chris and Jena shared their backgrounds, explaining how they both grew up in military households and eventually met at the Air Force Academy. They discussed their initial entry into real estate, which began with a piece of advice from a mentor: buy a house at every base and turn it into a rental property when you move. This strategy laid the foundation for their real estate journey. Chris and Jena detailed their first p...

In this episode of The Short Term Show, Avery welcomed Laura Sides, a former middle school biology teacher who transitioned into real estate investing. Laura shared her journey from teaching to becoming a stay-at-home mom to discovering her passion for real estate and the challenges she has faced along the way. Laura explained her strategy of using HELOCs for short-term flips and paying them off quickly, rather than using them for long-term investments. She also touched on her experience transitioning to property manager for their short term rentals and they discussed the difficult task of firing property managers. 

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On this week's episode Avery had the pleasure of chatting with Rick Sharga, CEO and founder of the C.J. Patrick Company. Rick explained that the current market dynamics are driven by a significant number of young adults reaching the prime age for first-time home buying, coupled with a shortage of available homes. They also touched on the potential for relief in the market. Rick is optimistic that by the end of 2025, we might see mortgage rates drop to around 6%, with home prices stabilizing and wage growth continuing. They also explored how media reports influence consumer behavior more than a...

This week's episode is a deep dive into the challenging real estate landscape of 2024, which has been marked as the worst market in the past 65 years in terms of homes sold. Avery welcomes four top real estate agents; January Johnson, Pete Apposato, Wayde Hall and Jonathan Lazzarino to discuss the implications for short term rental investors. Their conversation covers buying and selling insights from the year, advice for navigating the current market conditions and what opportunities await buyers in 2025.

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/

In this episode of The Short Term Show, Avery dives into the critical aspects of real estate investing beyond the most commonly emphasized metrics of cash flow and cash on cash return. Throughout the episode Avery outlines three alternative wealth generating strategies that investors should keep in mind when calculating their return on investment. Avery acknowledges the importance of cash flow in achieving financial freedom while also encouraging listeners to broaden their perspective and consider additional ways to build wealth through real estate ownership.

Check out our previous episodes with licensed CPAs:

Amanda H...

On this week's episode Avery, Luke and Tim went over some of the essential strategies for navigating the holiday season and preparing for 2025. They discussed the importance of pricing and booking strategies as we approach Christmas and New Year's, especially with the holidays taking place on Wednesdays this year. Luke shared his approach to packaging holiday bookings, emphasizing the need to adjust prices for less desirable dates. He also touched on the significance of maintaining high base rates for the upcoming summer months while being proactive in filling in gaps during the slower winter season. They also discussed the d...

In this episode of The Short Term Show, host discusses cash flow management and investment strategies with guest M.C. Laubscher, a seasoned investor with nearly 25 years of experience. M.C. shared his unique background, growing up in South Africa during a time of significant change, which shaped his understanding of business and investing during uncertain times. Throughout the episode, he emphasized the importance of cash flow management, especially for business owners and real estate investors. He introduced the concept of the "four seasons of cash flow," highlighting the need to prepare for both high and low revenue months. H...

In this episode of the Short Term Show, Avery welcomes Jay Ulrich, CEO of HostBuddy AI, to discuss their innovative AI messaging software designed to enhance the STR experience for guests and hosts. Jay explains how HostBuddy aims to save hosts' time and money by improving response times and ensuring guests receive timely, human-like assistance. The software integrates seamlessly with property management systems and offers features beyond messaging, making it an essential tool for hosts managing multiple properties. Jay highlighted several advanced features, including upselling gap nights, inquiry winbacks, and smart templates that analyze guest sentiment to optimize communication.