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Mike Preshman didn’t start out planning to build a 220-unit multifamily portfolio. With a background in computer science and tech entrepreneurship, his entry into real estate began almost accidentally—with a vacation home on Cape Cod.

That first property opened his eyes to the income potential of real estate. He added more vacation rentals before realizing that the model was difficult to scale. Over the next decade, Mike shifted toward multifamily properties throughout Greater Boston and the Northeast, ultimately building his portfolio without bringing in outside equity investors.

In this episode of Weiss Advice, Mike explains why his strategy has centered on cash flow, downside protection, and owning assets that can be held for the long term rather than relying on appreciation and a future sale.

He also shares the contrarian philosophy behind his investing: “Be a cat when everybody’s a dog.” When investors pile into the hottest markets and strategies, Mike would rather look for opportunities others are overlooking.

The conversation goes beyond real estate into decision-making, masterminds, poker, asymmetric risk, and why successful investing requires being comfortable making decisions when the outcome is uncertain. Mike also explains how his definition of success has evolved—and why building wealth today is increasingly tied to a much bigger mission.

Timestamps

00:52 – Mike’s journey from tech entrepreneur to real estate investor
01:56 – The accidental vacation rental that started everything
07:15 – Why Mike wants “generational assets” instead of playing real estate “hot potato”
12:19 – “Be a cat when everybody’s a dog”: Mike’s contrarian investing philosophy
15:00 – Masterminds, surrounding yourself with growth-minded people, and avoiding shiny objects
19:51 – What poker taught Mike about investing and decision-making under uncertainty
21:55 – Avoiding paralysis by analysis and taking risks that won’t wipe you out
27:17 – Asymmetric risk: protecting the downside while preserving the upside
30:45 – What success means to Mike today
32:49 – The ambitious lifetime giving goal that became Mike’s North Star

Mike’s story is a reminder that building wealth doesn’t necessarily require following the hottest market, raising large amounts of outside capital, or constantly selling assets. Sometimes the bigger opportunity comes from thinking independently, protecting the downside, and building something you’re comfortable owning for decades.

Connect with Mike:

https://www.linkedin.com/in/mike-preshman-4347a31/

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