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

On this week’s episode of The Short Term Show, Avery interviews Karlton Dennis. The two dig into how the short-term rental tax strategy actually works today, including what “material participation” really means in an audit. They cover using cost segregation and (current) bonus depreciation to create paper losses, the do’s and don’ts of hour-tracking, and smart Q4 timing for acquisitions. Karlton also shares pitfalls that trigger audits and when condos do (or don't) make sense.

How to connect with Karlton: 

https://taxalchemy.com/
https://www.instagram.com/taxalchemyadvisors/
https://www.instagram.com/karltondennis/

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 Andrew Llewellyn to unpack how he built a thriving short-term rental business in Louisville, KY. He shares the pivot from an almost-bakery to 10–30 guest stays, the data-driven playbook behind tiered calendar openings and last-minute pricing using throughput accounting, and why in-house cleaning and EOS/Traction keep operations tight. Andrew walks through converting an 18,000-sq-ft office into eight 4-bed/2-bath units (projected $800–$900k gross) after a first 10,000-sq-ft building that now grosses ~ $400k, plus the realities of SBA 504 financing (six–eight months and 40 bank conversations). Tech stack highlights include Guesty, PriceLabs (with manual event overrides), RemoteLock, and a heavy weekly metrics cadence. 

How to connect with Andrew: 

https://superstaysstr.com/
https://andrewllewellyn.com/
@iamandrewllewellyn

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 of The Short Term Show, Avery interviews Brenna Carles. They unpack what Powell’s recent signaling means for mortgages, why lenders “pre-price” ahead of Fed meetings, and how the 10-year Treasury, inflation, jobless claims, and non-farm payrolls flow through to rate sheets. Brenna shares where DSCR and conventional rates are landing now, why refis are penciling again (including cash-out options), and tactical ways to use seller credits to buy down rates.

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 Jae Seok An, founder of Airbtics, to dig into smarter market selection and the realities of STR data. They walk through Airbtics’ draw-your-own-market mapping, listing density by bedroom count, and the Market Explorer—tools aimed at helping newer investors compare many locations, budgets, and regulation profiles quickly. Jae shares where the platform is headed (more granular property-level history, clearer “active listing” definitions, and global coverage) and offers practical takes on saturation, accuracy, and why your operations can double or triple revenue on the same property. He closes with advice to start with free analytics, research multiple markets, and then narrow to neighborhood-level decisions.

How to connect with Jae:

airbtics.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 Rashmi Bhat. Rashmi shares how she went from opening a restaurant at 21 to falling in love with Airbnbs, quickly building a multi‑market STR portfolio and scaling management in the Texas Hill Country to dozens of units through systems and a VA team. She and Avery dig into why the Hill Country still has room for standout properties—and the realities (like taxes) investors should underwrite—plus how keeping a W‑2 can be a strategic “fortress” while you grow cash‑flowing assets. 

How to connect with Rashmi:

Toasty Indian on socials

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 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 and make smarter STR decisions.

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