Podcast Episodes
Back to SearchThe Guest Experience That Drives 5-Star Reviews with Frank Napolitano
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…
Published on 8 hours ago
Stop the Scroll: $20–60k Makeovers That Double Revenue ft. Joe DelGrosso
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 refr…
Published on 1 week ago
The New PriceLabs Features Every STR Owner Should Try with Thibault Masson
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 res…
Published on 2 weeks ago
Insurance Lessons Every STR Investor Must Hear with Toni Boer
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 …
Published on 3 weeks ago
From Caregiver to Condo Investor with Tamara Brown
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 purchasin…
Published on 4 weeks ago
The Truth About Buying “Ugly” Cabins That Cash Flow with Amy Morehead
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 strate…
Published on 1 month ago
How HelloHost AI Levels Up Your Hosting with Annie Li
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 h…
Published on 1 month, 1 week ago
The Truth About Material Participation Rules with Karlton Dennis
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” r…
Published on 1 month, 2 weeks ago
Why Hosting 30 Guests at Once Can Be Easier Than Hosting 2 with Andrew Llewellyn
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 st…
Published on 1 month, 3 weeks ago
What Falling Rates Mean for Real Estate Investors with Brenna Carles
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 t…
Published on 2 months ago