Tag: Real Estate Investing
How Opportunity Zones 2.0 Could Change Capital Gains Planning with Nick Rosenthal (Ep. 105)

How Opportunity Zones 2.0 Could Change Capital Gains Planning with Nick Rosenthal (Ep. 105)

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If you’re sitting on a large capital gain from appreciated stock, real estate, or the sale of a business, deciding what to do next can have tax and investment implications that extend well beyond the year of the sale. Timing, liquidity, investment structure, and your long-term plan all matter.

In this episode, Robert Curtiss talks with Nick Rosenthal, Co-Chief Executive Officer of Griffin Capital Company, LLC, about Qualified Opportunity Zones and the 2.0 rules beginning in 2027. They explain the five-year deferral period, 10% gain reduction, and potential tax treatment after a 10-year hold. Nick also covers eligible gains, 180-day investment windows, real estate development timelines, income expectations, portfolio diversification, and why manager selection and investment discipline should come before tax benefits. They also look at appreciated stock, real estate, and business-sale gains.

Nick discusses:

  • How Opportunity Zones 2.0 create five years of tax deferral and a 10% reduction on deferred gains for investors
  • Which capital gains may qualify, including appreciated stock, real estate, and business-sale proceeds
  • How the 180-day investment window changes for individual gains, pass-through entities, and K-1 income
  • Why development, stabilization, and income phases shape the return profile of opportunity zone funds
  • Why manager selection, portfolio quality, and investment discipline should come before the tax benefits
  • And more!

Resources:

Connect with Nick Rosenthal:

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About Our Guest:

Mr. Rosenthal serves as Co-Chief Executive Officer at Griffin Capital Company, LLC, where he is responsible for working directly with the firm’s executives across Acquisitions, Asset Management, Due Diligence, Product Development, Accounting, Investor Relations, Marketing, and Equity Sales. In this capacity, Mr. Rosenthal is responsible for directing the firm’s strategic vision and advancing key initiatives across the organization. With extensive experience and expertise in both the financial services and real estate industries, Mr. Rosenthal has authored whitepapers on real estate investing and associated financial planning strategies. He is highly regarded for his thought leadership and is often featured in industry publications and events, offering insight into the current investment dynamics in the property markets. Mr. Rosenthal has been involved in the underwriting and acquisition of multifamily and industrial real estate investments and has been directly responsible for raising over $2 billion of investor capital across various real estate strategies and investment structures.

Mr. Rosenthal is a registered Series 7 licensed representative. He is a Graduate of George Washington University and a resident of Newport Beach, California, where he resides with his wife and two sons.
Private Commercial Real Estate After the Market Reset with PGIM’s Andrew Garten (Ep. 104)

Private Commercial Real Estate After the Market Reset with PGIM’s Andrew Garten (Ep. 104)

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Commercial real estate has repriced, but the opportunity isn’t the same across every property type or market. 

What should investors weigh before adding it to a long-term portfolio?

In this episode, Robert Curtiss speaks with Andrew Garten, Alternative Investment Specialist at PGIM, about the case for private commercial real estate after the 2022 to 2024 market reset. They cover where PGIM sees demand across housing, senior living, medical offices, logistics, and necessity-based retail.

Andrew explains how core real estate may combine income, growth, tax deferral, and lower correlation with stocks and bonds. They also address liquidity, allocation ranges, manager selection, and why local supply and demand can shape results.

Andrew discusses:

  • Why the 2022 to 2024 market reset may have improved pricing across selected commercial real estate sectors
  • How senior housing, student housing, medical offices, and logistics reflect essential demand and limited supply
  • How core real estate may combine income and growth while behaving differently from public stocks and bonds
  • Why depreciation may defer part of private REIT income and affect an investor’s cost basis over time
  • How liquidity needs, retirement timing, and portfolio goals can influence an appropriate real estate allocation
  • And more!

Resources:

Connect with PGIM :

Connect with Robert Curtiss:

About Our Guest:

Andrew Garten is an Alternative Investment Specialist at PGIM, the asset management business of Prudential Financial. With more than 20 years of experience, he focuses on helping investors understand opportunities across private markets, including commercial real estate. In his role, Andrew draws on PGIM’s global real estate platform and long operating history to explain how property type, location, income potential, tax treatment, and liquidity can affect an investment. He holds a Bachelor of Science in International Business Technology, International Studies, and French from the Pamplin College of Business.
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)

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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.

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

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

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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.

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