Zen and the Art of Real Estate Investing with Jonathan Greene

How to Make Your Real Estate Investing Journey Take Off with Shawn DiMartile


Shawn DiMartile transitioned from a high-stress air traffic control job to a real estate investing career in a bold career move. On this episode of Zen and the Art of Real Estate Investing, Jonathan delves into Shawn’s journey, where Shawn shares his rapid ascent in real estate, boasting over 300 rental units since he began in 2018. As the co-founder of Takeoff Capital, host of The Real Estate Takeoff podcast, and a Navy veteran, Shawn’s primary investing focus is on apartments.

Jonathan and Shawn explore his initial exposure to real estate investing, including his parents’ advice using Dave Ramsey’s principles and eventually books and podcasts on real estate investing. The conversation reveals why Shawn, despite his flourishing air traffic control career, wishes he had delayed his full-time plunge into real estate. He shares some of the challenges of raising funds for real estate syndication, why he thinks it’s harder than air traffic control, and details his first investment, including the strategic partnership that made it possible.

The discussion also highlights Shawn’s deliberate choice to buy property in Indiana over his California residence, his ventures into San Diego’s accessory dwelling units (ADUs), and his advice for novice investors. While real estate syndication and ADUs might not have been on your investment horizon, Shawn articulates compelling reasons to consider them.


You’ll also hear:

  • Shawn has one regret about leaving his air traffic control career. He wishes he’d delayed quitting a bit longer because he could have doubled his investing potential.

  • Investing in B+ neighborhoods has been better for him than investing in D neighborhoods. They’re less risky than bad neighborhoods and appreciate faster.

  • The barrier to entry for investing was much lower in Indiana than in California, and that’s the primary reason he and his business partners opted to buy property in Indiana.

  • Accessory dwelling units (ADUs) have been an excellent investing choice for Shawn. ADUs in San Diego are essentially apartment buildings built on land where a single or multifamily property once existed.


Shawn’s insights on his investing career after a stint as an air traffic controller could be the push you need to help your investing journey take off.

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