On this week’s episode, Avery is joined by Ari Rastagar. Ari shares how he built a multibillion-dollar real estate firm starting with just $3,500 and explains why real estate is far more operationally complex than most beginners expect. He dives into the importance of risk management, due diligence, and local market expertise, highlighting common mistakes investors make—especially when relying too heavily on spreadsheets instead of real-world context. The conversation also explores why short term rentals require an intense focus on customer experience and operations, and how scaling systems and processes is key to long-term success.

How to connect with Ari:

Website: https://rastegarcapital.com/
LinkedIn: https://www.linkedin.com/in/arirastegar/
Instagram: https://www.instagram.com/rastegar
TikTok: https://www.tiktok.com/@arirastegar

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 Cathy Craig, a top agent and investor in Broken Bow, Oklahoma, who shares an inside look at the current market and why now may be a prime time to buy. She explains how prices have come down significantly from peak levels while demand and occupancy remain strong, pushing back on the idea of “oversaturation” and emphasizing that the market continues to grow with infrastructure and tourism. Cathy also highlights what actually drives success in this market, focusing on guest experience, smart upgrades, and avoiding over-investing in unnecessary amenities. She wraps with real examples of high-performing properties and practical advice on buying right, adding value, and standing out without overspending.

How to connect with Cathy:

www.theshorttermshop.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

Avery is joined by Katie Johnson, a short-term rental attorney and investor who breaks down the most common legal mistakes hosts make and how to avoid them. She explains key risks like missing deed restrictions, improperly handling LLCs, and failing to secure adequate insurance, along with how to protect yourself from lawsuits tied to pools, amenities, and guest incidents. Katie also dives into service animals vs. emotional support animals, the legal realities of raising capital, and why setting up your business structure correctly from the start is critical. The conversation highlights how being proactive with legal strategy can save investors from costly mistakes down the road.

How to connect with Katie:

@katiethereattorney
strlaw.com
katiejohnsonplc.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