About this episode

Chris McKenna shares his journey from a Fortune 500 executive to retiring at 49 by building a successful short-term rental portfolio.

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 Follow Avery Carl on TikTok Join the Short Term Shop…

People in this episode

Host: Avery Carl

Guest: Chris McKenna

Topics covered

• short-term rentals
• real estate investing
• portfolio building
• retirement
• property management

Keywords

• short-term rental
• real estate
• retirement
• property portfolio
• vacation rentals
• investment strategy

Mentioned in this episode

Organizations: BiggerPockets, Short Term Shop, Amazon

Places: Alabama, Oklahoma, Maine

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