Avery Carl sits down with Erica and Jon Larson, a former teacher and a VP of sales who turned a career shake-up into a thriving short‑term rental business. They share the real, often messy process of leaving their W‑2 jobs—starting with a tight budget, learning the hard way why you never skip a home inspection, and the nightmare of trusting a realtor who wasn’t an STR expert. From teaching kindergarteners to managing guest messages mid‑class, Erica and Jon walk through the grit, risk, and persistence it took to buy their first Smoky Mountains property in 2022 and eventually replace one full‑time income. This conversation is packed with candid lessons for anyone dreaming of trading a traditional job for property‑based freedom.

Connect with Erica and Jon:

Website: CYLPrentals.com
Instagram: https://www.instagram.com/changeyourlatitudeproperties/

Connect with us:

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

Avery is joined by Short Term Shop agent Stacey Lancaster to explore the current state of short-term rental investing across Texas Hill Country and the Austin area. Stacey explains why the market currently favors investors who are willing to negotiate, create memorable guest experiences, and look beyond turnkey properties to add value through design and management. They also discuss how continued population growth in Texas, future developments like Fredericksburg’s incoming Waldorf Astoria, and shifting market conditions could shape demand in the years ahead.

Connect with an agent: agents@theshorttermshop.com

Connect with us:

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

Avery Carl is joined by Short Term Shop agent Cody Roberts to break down why Southern Utah has become an increasingly attractive short-term rental market. They discuss the tourism demand driven by Zion National Park and the surrounding outdoor attractions, the strict permit regulations that help prevent oversaturation, and the types of properties that perform best in the market. The conversation also covers the benefits of condos and townhomes with resort-style amenities, the appeal of purpose-built short term rental communities, and why investors need to understand local regulations before buying in areas like St. George and Hurricane.

Connect with an agent: agents@theshorttermshop.com

Connect with us:

The Short Term Shop - https://theshorttermshop.com/
https://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 Ana Klein, CEO of Tax Boss, to break down how short term rental tax law can help high income earners significantly reduce their taxable income. Ana explains how strategies like cost segregation and bonus depreciation can create large paper losses that offset W2 income, while emphasizing that these benefits only work when paired with strong investments and long term planning. The conversation dives into common misconceptions, including year-one benefits, depreciation recapture, and why trying to game real estate professional status can backfire. They also highlight the importance of proper bookkeeping, time tracking for material participation, and working with qualified professionals to avoid costly IRS audits and mistakes.

How to connect with Ana:

https://www.instagram.com/taxbossana/

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 Dohn Thornton, a seasoned real estate investor and short sale expert who has flipped over 3,000 properties and now focuses on advanced asset protection strategies. Dohn breaks down the concept of a spendthrift trust, explaining how it differs from traditional LLCs and trusts by offering greater privacy, lawsuit protection, and potential tax advantages through a contract law structure. The conversation dives into how these trusts can shield assets from discovery, avoid triggering taxable events, and fundamentally change how investors think about income, expenses, and wealth management. Dohn also shares real world examples from his own business, including how switching to this structure deterred lawsuits entirely and reshaped his approach to investing and long-term wealth building.

How to connect with Dohn:

https://bensonfinancial.us

Instagram: @dohnthornton

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 Emily Tunggala. Emily shares how Hospitable is expanding beyond traditional property management software by launching a marketplace that connects property managers with owners looking for help. She explains how the platform uses performance data and insights to match the right managers with the right properties, while also giving newer managers tools to onboard clients professionally. The conversation highlights how this could change the way managers find clients, reduce time spent chasing leads, and create more opportunity based on results rather than connections.

How to connect with Emily:

https://hospitable.com/

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 Brian Boyd. Brian, a tax attorney and real estate investor, breaks down how the short term rental tax strategy works, explaining how investors can use cost segregation and bonus depreciation to offset active income while building wealth. He emphasizes the importance of self-managing properties, tracking time accurately, and understanding the rules to properly qualify for these tax benefits. The conversation also dives into common mistakes investors make, like overspending on furnishings or prioritizing tax savings over cash flow, and highlights how real estate can be a powerful long-term wealth-building tool when approached strategically.

How to connect with Brian:

YouTube: @yourtaxlawyer
Instagram: briantboyd
TikTok: @briantboyd
Facebook: Brian T Boyd

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 Kim Fitzpatrick. Kim shares how she went from being a PE teacher and single mom to launching her first Airbnb with an air mattress, eventually scaling into multiple investment properties across markets like the Smokies and Montana. She breaks down how her hands-on experience renovating and setting up properties led to founding Launched Host, a service that helps investors go from empty to guest-ready in just seven days. The conversation also highlights the realities of launching short term rentals, the importance of systems and guest experience, and how simplifying setups can reduce stress and improve long-term success.

How to connect with Kim:

Launchedhost.com
https://www.instagram.com/launchedhost?igsh=dnNhYXpjbGZsbHBm&utm_source=qr
https://www.facebook.com/share/1K5wTTDLjP/?mibextid=LQQJ4d

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