#274

In this episode, we sit down with Jason Woodward and unpack a real-life investing journey that starts with flipping boats (yes, boats) and turns into building a real estate portfolio while still working a full-time W-2. Jason shares how learning the basics through coaching and community gave him the confidence to finally take action—and why the “right room” can speed up your timeline by years.

Jason walks through the early deals—including a first flip that turned into a brutal (but useful) education: old houses, plaster and lath surprises, scope creep, hard money pressure, and the reality of paying for mistakes. He breaks down how he funded projects (including hard money and a 401k loan), what he’d do differently now, and how his strategy evolved from heavy DIY to “do less, hire more.”

We also get into what it looks like investing in today’s market—when properties don’t fly off the shelf in a weekend anymore. Jason explains why multiple exit strategies matter (flip, rental, midterm rental, etc.), how he handled a property that sat longer than expected, and what features can quietly kill demand even after a good rehab. And then there’s the townhome curveball: a deal that should’ve closed… until an HOA insurance problem nuked the finish line.

Along the way, there are some classic REIA Radio moments—like randomly getting a call from the very coach being credited for the entire journey… while recording live. Because apparently the universe has a sense of humor.

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