Jacob Winn: From Managing a Hedge Fund to Investing in Apartments

Jacob Winn: From Managing a Hedge Fund to Investing in Apartments

April 16, 2026 · 41 min · Season 3 · Episode 29

About this episode

Jacob Winn discusses his transition from hedge funds to real estate investing and the insights he gained along the way.

Today, I welcome Jacob Winn to The Investing Secrets Podcast. Jacob is part of the team at Rex and today he shares how his background in hedge funds, derivatives, and quantitative risk management shaped the way he evaluates real estate opportunities in today’s market. He breaks down why he believes many investors misunderstand alternative investing, how real estate can offer meaningful diversification and tax advantages beyond traditional public market strategies, and why clarity around cash ...

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Host: Danny Gould

Guest: Jacob Winn

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Organizations: Rex

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