393. The Truth About Buying a Short-Term Rental for Tax Benefits: Joey Linn’s First Deal, a Flood & What He Learned
About this episode
Joey Linn discusses his transition from sports media to real estate investing, focusing on his first short-term rental experience and the associated tax benefits.
Joey Linn went from covering NBA stars for Sports Illustrated to buying and remotely managing his first short-term rental in Michigan City, Indiana. The original motivation? A growing business had created a significant tax problem, and Joey saw short-term rental real estate as an opportunity to combine potential tax benefits with an appreciating, cash-flowing asset. But his first deal quickly became a real-world education in real estate investing. In this episode, Joey joins Thomas Castelli, CPA, and Nate Sosa to explain why he invested in the Midwest instead of Southern California, how he bought his first property without seeing it in person, and how he built a local team to manage the property remotely. Plus, Joey shares his journey from sports media to entrepreneurship, how AI is changing the sports-writing business, and what could be next for his real estate portfolio. Request a consultation from Hall CPA at go.therealestatecpa.com/taxsmart Register for FREE access to the 2026 Hall CPA Tax Strategy Summit: www.taxandlegalsummit.com/2026signup Join the Hall CPA Team: go.therealestatecpa.com/team Submit your question for Tom & Nathan: go.therealestatecpa.com/question The Tax…
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