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Weiss AdviceAuthor: Yonah Weiss
Learning from the Best in Real Estate Business and Beyond. I love talking to successful people, and asking them for advice and tips on business and life. I'm very blessed to have an amazing network. They say your Network is your Net Worth, and it's true. If you want to learn more from these successful people, listen in. Learn more at www.yonahweiss.com Language: en-us Genres: Business, Entrepreneurship, Investing Contact email: Get it Feed URL: Get it iTunes ID: Get it |
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“Be a Cat When Everybody’s a Dog”: How Mike Preshman Built a 220-Unit Portfolio
Thursday, 10 September, 2026
Send us Fan MailMike 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.Timestamps00:52 – 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 StarMike’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/LEAVE A 5-STAR REVIEW by clicking this link.WHERE CAN I LEARN MORE?Be sure to follow me on the below platforms:Subscribe to the podcast on Apple, Spotify, Google, or Stitcher.LinkedInYoutubeExclusive Facebook Groupwww.yonahweiss.comNone of this could be possible without the awesome team at Buzzsprout. They make it easy to get your show listed on every major podcast platform.Support the showSupport the show
