#236: Flipping, Failing, and Figuring It Out: The Real Investor Life of Jackson Udy

In Episode 236 of REIA Radio, we dive into the investing journey of Jackson Udy, a full-time chemical engineer who’s been quietly building a real estate portfolio across state lines. Jackson shares how he got started by buying a duplex in Omaha while living in California, the ups and downs of managing from afar, and why partnering with family—especially through self-directed IRAs—isn’t always as smooth as it sounds.

He opens up about the reality of failed flips, like the one that ended with a surprise $22,000 plumbing bill, and a more recent deal that looked great on paper but burned him and his brother for a $15,000 loss each. Through it all, Jackson talks candidly about learning to trust his gut, the importance of actually managing your team, and how his W-2 career is still a key part of his long-term strategy.

He’s flipped houses, navigated eviction moratoriums, dealt with homeless encampments on the news, and still somehow finds time for his wife, kids, and crazy real estate ideas like turning a side yard into taco truck parking.

If you’ve ever thought about investing out of state, managing rentals remotely, or scaling without quitting your day job, Jackson’s stories and lessons will hit home.

🎧 Listen now and learn how to avoid turning someone else’s failed flip into your financial nightmare.

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