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