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