393. The Truth About Buying a Short-Term Rental for Tax Benefits: Joey Linn’s First Deal, a Flood & What He Learned

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.

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