JF 3906: Deferred Gains, Development Risk, and Diversified Portfolios ft. Michael O’Shea

On this episode of the Passive Income Playbook, Pascal Wagner interviews Michael O’Shea, Head of Private Wealth at Origin Investments. Michael shares how his firm has built a $3.3B portfolio offering institutional-quality investments to high-net-worth individuals, particularly through tax-advantaged vehicles like DSTs and Opportunity Zone funds. The episode dives deep into the mechanics, benefits, and misconceptions around both strategies—highlighting when each is appropriate, how they support estate planning, and their roles in diversifying and deferring or eliminating taxes. Michael also addresses regulatory expectations and why Origin’s vertically integrated model gives investors access to highly curated, risk-managed real estate opportunities. Michael O’Shea Current Role: Head of Private Wealth, Origin Investments Based in: Chicago, IL Say hi to them at: origininvestments.com → Book a call via team page Get a 4-week trial, free postage, and a digital scale at ⁠https://www.stamps.com/cre⁠. Thanks to Stamps.com for sponsoring the show! Post your job for free at https://www.linkedin.com/BRE. Terms and conditions apply. Try Huel with 15% OFF + Free Gift for New Customers today using my code bestever at https://huel.com/bestever. Fuel your best performance with Huel today! Join the Best Ever Community The Best Ever Community is live and growing - and we want serious commercial real estate investors like you inside. It’s free to join, but you must apply and meet the criteria. Connect with top operators, LPs, GPs, and more, get real insights, and be part of a curated network built to help you grow. Apply now at ⁠www.bestevercommunity.com⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices