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PODCAST

The Short Term Show

8 Figure Airbnb and Short Term Rental Real Estate Investor Avery Carl

The Short Term Show is your home for all things short term rental (Airbnb) investing and management. Host Avery Carl interviews successful real estate investors and CEOs of Airbnb related startups to bring inspirational and actionable content to listeners. Whether you are an experienced Airbnb investor or co-host, or you’re just getting started, The Short Term Show is your home for all things short term rental content. About the host: Avery Carl bought her first Airbnb in 2015, and has since built

business investing

All Episodes

00:30:58

Other People’s Everything: Scaling Your STR Empire...

The Short Term Show ·

2025/11/12

On this week's episode, Avery is joined by Bethany LaFlam, a “recovering attorney,” community architect, and author of The Power of OPE. Bethany and Avery dive into what it really means to stay in your lane, leveraging “other people’s everything” (money, time, assets, skills) so you can scale without burning out. They break down how to safely and legally use other people’s money in syndications, why true operators—not just capital raisers—are the ones

en-US

00:30:58

Other People’s Everything: Scaling Your STR Empire...

The Short Term Show ·

2025/11/12

On this week's episode, Avery is joined by Bethany LaFlam, a “recovering attorney,” community architect, and author of The Power of OPE. Bethany and Avery dive into what it really means to stay in your lane, leveraging “other people’s everything” (money, time, assets, skills) so you can scale without burning out. They break down how to safely and legally use other people’s money in syndications, why true operators—not just capital raisers—are the ones

en-US

00:29:07

The Guest Experience That Drives 5-Star Reviews with...

The Short Term Show ·

2025/11/05

On this week's episode, Avery is joined by Frank Napolitano. Frank shares how he and his family transitioned into short-term rentals in the Smokies, leveraging bonus depreciation and cost segregation to maximize tax advantages. He discusses what makes their property stand out—like a pool, tiki bar, and ADA accessibility—and how small touches such as holiday decorations and guest amenities have led to rave reviews. Frank also talks about navigating market

en-US

00:29:07

The Guest Experience That Drives 5-Star Reviews with...

The Short Term Show ·

2025/11/05

On this week's episode, Avery is joined by Frank Napolitano. Frank shares how he and his family transitioned into short-term rentals in the Smokies, leveraging bonus depreciation and cost segregation to maximize tax advantages. He discusses what makes their property stand out—like a pool, tiki bar, and ADA accessibility—and how small touches such as holiday decorations and guest amenities have led to rave reviews. Frank also talks about navigating market

en-US

00:43:14

Stop the Scroll: $20–60k Makeovers That Double...

The Short Term Show ·

2025/10/29

On this week's episode, Avery is joined by Joe DelGrosso. Joe shares his journey from working in TV production to owning short-term rentals and why his first Smokies cabin proved that thoughtful refreshes can outperform flashy, high-cost amenities. He explains his boutique management approach at Southern Sons Hospitality, focusing on capped inventory, strong revenue management, and design upgrades that truly make properties stand out. Joe also offers

en-US

00:43:14

Stop the Scroll: $20–60k Makeovers That Double...

The Short Term Show ·

2025/10/29

On this week's episode, Avery is joined by Joe DelGrosso. Joe shares his journey from working in TV production to owning short-term rentals and why his first Smokies cabin proved that thoughtful refreshes can outperform flashy, high-cost amenities. He explains his boutique management approach at Southern Sons Hospitality, focusing on capped inventory, strong revenue management, and design upgrades that truly make properties stand out. Joe also offers

en-US

00:34:29

The New PriceLabs Features Every STR Owner Should Try...

The Short Term Show ·

2025/10/22

On this week’s episode, Avery is joined by Thibault Masson, Head of Product Marketing at PriceLabs. They unpack Booking.com’s challenges in the U.S. versus Europe and how Airbnb’s fee changes are reshaping the playing field, before diving into PriceLabs updates like Dynamic Minimum Stay, the new Listing Optimizer, and a free revenue-management course. Avery also spotlights Market Dashboards for comp sets, cleaning-fee benchmarking, and smarter buy-box

en-US

00:34:29

The New PriceLabs Features Every STR Owner Should Try...

The Short Term Show ·

2025/10/22

On this week’s episode, Avery is joined by Thibault Masson, Head of Product Marketing at PriceLabs. They unpack Booking.com’s challenges in the U.S. versus Europe and how Airbnb’s fee changes are reshaping the playing field, before diving into PriceLabs updates like Dynamic Minimum Stay, the new Listing Optimizer, and a free revenue-management course. Avery also spotlights Market Dashboards for comp sets, cleaning-fee benchmarking, and smarter buy-box

en-US

00:43:51

Insurance Lessons Every STR Investor Must Hear with...

The Short Term Show ·

2025/10/15

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

en-US

00:43:51

Insurance Lessons Every STR Investor Must Hear with...

The Short Term Show ·

2025/10/15

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

en-US

00:31:13

From Caregiver to Condo Investor with Tamara Brown

The Short Term Show ·

2025/10/08

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

en-US

00:31:13

From Caregiver to Condo Investor with Tamara Brown

The Short Term Show ·

2025/10/08

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

en-US

00:39:50

The Truth About Buying “Ugly” Cabins That Cash Flow...

The Short Term Show ·

2025/10/01

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

en-US

00:39:50

The Truth About Buying “Ugly” Cabins That Cash Flow...

The Short Term Show ·

2025/10/01

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

en-US

00:33:21

How HelloHost AI Levels Up Your Hosting with Annie Li

The Short Term Show ·

2025/09/24

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

en-US

00:33:21

How HelloHost AI Levels Up Your Hosting with Annie Li

The Short Term Show ·

2025/09/24

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

en-US

00:39:18

The Truth About Material Participation Rules with...

The Short Term Show ·

2025/09/17

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

en-US

00:39:18

The Truth About Material Participation Rules with...

The Short Term Show ·

2025/09/17

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

en-US

00:34:15

Why Hosting 30 Guests at Once Can Be Easier Than...

The Short Term Show ·

2025/09/10

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

en-US

00:34:15

Why Hosting 30 Guests at Once Can Be Easier Than...

The Short Term Show ·

2025/09/10

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

en-US

459 results

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