Tag: Real Estate Investing

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)

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 evergreen educational resource for investors who want to understand their options well before a liquidity event occurs.

Key takeaways:

  • How Qualified Opportunity Zones work and why they were created
  • What’s changing in Opportunity Zone legislation starting in 2027
  • How Opportunity Zones may help address large capital gains from stocks, businesses, or real estate
  • Why long-term real estate development and coordinated planning are key to using this strategy effectively
  • And more!

Resources:

Connect with Michael O’Shea:

Connect with Robert Curtiss:

 

About Our Guest:

Michael brings more than 18 years of real estate and capital markets expertise to Origin as Director and Head of Private Wealth Solutions. In this role, he leads the firm’s capital raising initiatives, oversees the sales strategy, and develops strategic partnerships with Registered Investment Advisors (RIAs) to expand Origin’s investment platform.

Previously, Michael served as the head of Origin Exchange, the firm’s 1031 Exchange Platform. During his career in the alternative investment sector, Michael has played key roles with various real estate sponsors, facilitating the syndication of more than $10 billion in commercial real estate investments, including over $500 million in 1031 tax-deferred exchanges.

Michael holds an MBA with dual concentrations in Finance and Real Estate Investment from DePaul University, where he graduated summa cum laude. He earned his bachelor’s degree from Purdue University and is a CFA® charterholder.

A resident of Elmhurst, Michael lives with his wife Lauren and their three children Declan, Alice, and Tristan. Outside of work, he enjoys golf, Chicago sports, and spending time with his family.

How to Tap into Private Investments with Bob Long (Ep. 61)

How to Tap into Private Investments with Bob Long (Ep. 61)

Private markets are no longer just for the financial elite—they’re now within reach of individual investors. But how do you make the most of this opportunity without missing out on serious growth?

This week on The Millionaire Next Door, Bob Long, CEO of StepStone Private Wealth, explains how innovative structures like evergreen funds are making it easier to access private equity, credit, real estate, and infrastructure. With features like seamless entry, daily asset valuation, and simplified tax reporting, these investments are transforming how investors build their portfolios.

Find out why diversifying into private markets is more important than ever as public company listings decline while learning how these investments could fuel growth, offer stable income, and protect against inflation.

Key topics discussed include:

  • The growing accessibility of private market investments for individual investors
  • Understanding the distinctions among private equity, credit, real estate, and infrastructure
  • Benefits of StepStone’s evergreen funds for seamless investing
  • Global trends shaping private infrastructure investments
  • Key considerations for accredited investors, including liquidity and advisory collaboration
  • Reasons having a financial advisor in your corner can make all the difference
  • And much more!

Resources:

Connect with Bob Long:

Connect with Robert Curtiss:

About Our Guest:

Bob Long is the CEO of StepStone Private Wealth. Bob has three decades of experience in the private markets and has led investment teams for global firms in both the general partner and limited partner roles. He has served as the CEO of two publicly traded companies focused on expanding private market access for high-net-worth investors.

Prior to joining StepStone, Bob was the CEO of OHA Investment Corporation, a publicly traded specialty finance company. Previously, he co-founded Conversus Capital, the largest publicly traded fund of third-party private equity funds with $3 billion of AUM, and served as its CEO. Previously, Bob led Bank of America’s $7 billion strategic capital division. Early in his career, Bob served as the lead in-house counsel for a large portion of Bank of America’s Investment Banking Division and worked as a securities lawyer for a major law firm.