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

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