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

How to connect with Taylor:

https://roamfreevhr.com/
https://www.instagram.com/roamfreevhr/

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/
www.strquestions.com
Follow Avery Carl on Instagram
Follow Avery Carl on TikTok
Join the Short Term Shop Facebook group
Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

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

 How to connect with Brandon:

https://www.linkedin.com/in/brandonhallcpa/
https://www.facebook.com/realestatecpa
https://x.com/TheRECPA
www.therealestatecpa.com

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/
www.strquestions.com
Follow Avery Carl on Instagram
Follow Avery Carl on TikTok
Join the Short Term Shop Facebook group
Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

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

How to connect with Yonah:

https://yonahweiss.madisonspecs.com/
https://www.yonahweiss.com/
https://www.instagram.com/yonahweiss/
https://www.linkedin.com/in/cost-segregation-yonah-weiss/
https://twitter.com/YonahWeiss

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/
www.strquestions.com
Follow Avery Carl on Instagram
Follow Avery Carl on TikTok
Join the Short Term Shop Facebook group
Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

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 connect with Heather:

@roaminghomeheather

theembersbranson.com

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/
www.strquestions.com
Follow Avery Carl on Instagram
Follow Avery Carl on TikTok
Join the Short Term Shop Facebook group
Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week's episode, Avery is joined by 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 mindset shifts that helped them go from accidental investors to full-time entrepreneurs.

How to connect with Melissa and Chris:

https://bestvacationrentalsever.com

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/
www.strquestions.com
Follow Avery Carl on Instagram
Follow Avery Carl on TikTok
Join the Short Term Shop Facebook group
Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode, Avery is joined by 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 markets.

How to connect with Nathan:

Instagram: nathan_stcyr 

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/
www.strquestions.com
Follow Avery Carl on Instagram
Follow Avery Carl on TikTok
Join the Short Term Shop Facebook group
Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week’s episode, Avery is joined by 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 guest experiences.

How to connect with Isaac:

isaacjfrench.com 
Instagram.com/isaacfrench_
X.com/isaacfrench_
https://www.linkedin.com/in/isaacjfrench/

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/
www.strquestions.com
Follow Avery Carl on Instagram
Follow Avery Carl on TikTok
Join the Short Term Shop Facebook group
Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week's episode, Avery is joined by 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 Matt:

Instagram

TikTok

Youtube

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/
www.strquestions.com
Follow Avery Carl on Instagram
Follow Avery Carl on TikTok
Join the Short Term Shop Facebook group
Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week's episode, Avery is joined by 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 never too late to turn things around.

How to connect with Portia:

portialouder.com

How to connect with Avery:

The Short Term Shop - https://theshorttermshop.com/
www.strquestions.com
Follow Avery Carl on Instagram
Follow Avery Carl on TikTok
Join the Short Term Shop Facebook group
Check out the Short Term Shop on YouTube

For more information on how to get into short term rentals, read Avery’s books:

Smarter Short Term Rentals - Buy it on Amazon
Short-Term Rental, Long-Term Wealth: Your Guide to Analyzing, Buying, and Managing Vacation Properties – Buy it on Amazon

On this week's episode, Avery is joined by 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 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