How Chris McKenna Built a 10-Property STR Portfolio and Retired in Just a Few Years

On this week's episode, Avery is joined by Chris McKenna, a former Fortune 500 executive who retired at 49 after building a portfolio of short-term rentals across Alabama, Oklahoma, and Maine. Chris shares how hearing Avery on a BiggerPockets podcast sparked his real estate journey, leading him from a demanding corporate career to owning multiple vacation rental properties that now generate nearly $1 million in annual revenue. He recounts the unforgettable challenges of his first investment property—including a renovation disaster that landed him in the emergency room with Bell’s palsy—and explains why staying focused on long-term goals helped him keep moving forward. Chris also discusses scaling a portfolio across multiple markets, transforming underperforming properties through strategic upgrades, and the lessons he learned from purchasing and revitalizing a lakeside cabin resort in rural Maine.

How to connect with Chris:

https://lawrenceslakesidecabins.com/
https://vandellvacationrentals.com/gulfshores/

Connect with us:

The Short Term Shop - https://theshorttermshop.com/
https://stsplus.com/
Follow Avery Carl on Instagram
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Join the Short Term Shop Facebook group
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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