Opportunity Zones Explained: What’s Changing in 2027 and Why It Matters with Michael O’Shea (Ep. 91)

Opportunity Zones Explained: What’s Changing in 2027 and Why It Matters with Michael O’Shea (Ep. 91)

From The Millionaire Next Door by Robert Curtiss

February 17, 2026 · 32 min

About this episode

This episode explores Opportunity Zones and their implications for investors, particularly with upcoming changes in 2027.

For investors facing concentrated wealth or future liquidity events, understanding tax-aware planning options matters long before decisions are required. Opportunity Zones are one of the most talked-about and least understood tools in that conversation. In this episode of The Millionaire Next Door Podcast, Robert Curtiss sits down with Michael O’Shea, CFA, Head of Private Wealth at Origin Investments, to unpack one of the most misunderstood and potentially powerful tax planning tools available today: Qualified Opportunity Zones. Together, they walk through how Opportunity Zones work, why the original structure created a temporary pause in interest, and why upcoming changes beginning in 2027 may reopen the door for investors facing large capital gains. The conversation focuses on real-world planning scenarios, including concentrated stock positions, private business exits, and highly appreciated real estate. Michael explains how Opportunity Zones differ from 1031 exchanges, what the long-term benefits may look like when paired with professionally managed real estate development, and why advanced coordination with tax and legal advisors matters. This episode is designed as an…

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