The Short Term Show

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...

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...

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...

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...

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...

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...

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 de...

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,...

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...

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, th...

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 op...

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...

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-te...

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”...

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 finan...

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 dow...

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 D...

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 backgrou...

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 discuss...

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 ne...

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...

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 th...

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 bloc...

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 improvemen...

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 benefi...