285: In this episode, I sit down with Jeremiah Boucher, founder and CEO of Patriot Holdings, to unpack how he went from losing everything in the 2008 real estate crash to building a commercial real estate portfolio of roughly 100 properties.

(Show Notes: REtipster.com/285)

Jeremiah has spent more than two decades investing in alternative real estate assets, with a major focus on self-storage, manufactured housing communities, and small bay industrial properties.

What I found especially interesting is how his strategy has evolved.

He started in single-family real estate, got wiped out in 2008, rebuilt through mobile home park investing, expanded into self-storage, and eventually found another opportunity hiding in plain sight: small bay industrial or flex industrial space.

We talk about why these seemingly different asset classes have more in common than you might think, why diversified streams of tenant income matter, and why “boring” real estate can sometimes provide a much stronger competitive edge.

Jeremiah also explains how greed and FOMO influenced his decisions before 2008, and what he looks at differently today when deciding whether an opportunity is actually worth pursuing.

We also cover owner financing, raising private capital, real estate funds, value-add investing, property management, manufactured housing development, and the challenges of scaling a real estate portfolio across multiple markets.

If you're interested in self-storage investing, mobile home parks, small-bay industrial, commercial real estate, land development, or finding a real estate strategy with sustainable cash flow, there’s a lot to unpack here.

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