How to Exit Active Ownership: 1031, DST, 721 Strategy with Michael O’Shea

Update: 2025-11-17

Description

Ready to stop managing headaches and keep more of your gains? In this episode, Michael O’Shea breaks down how seasoned investors pair 1031 exchanges with Delaware Statutory Trusts and then use a 721 roll-up to diversify, generate income, and add optional liquidity. He also exposes where DST fees hide and how data tools helped time the multifamily cycle. Press play to learn the smarter path from hands-on landlord to truly passive investor.

Key takeaways to listen for

[05:05 ] The two tax-code words that can change everything: “permanent exclusion”
[10:14 ] The simple move that lets you “exchange out” of management but keep the income
[14:56 ] How a 721 roll-up turns an illiquid asset into one with quarterly liquidity
[16:17 ] The hidden DST fees most investors overlook and how Origin stripped them out
[19:04 ] How machine learning helps predict rent growth with 95% accuracy

Resources mentioned in this episode

[36:02 ] Traction by Gino Wickman | Kindle, Paperback, and Hardcover
[37:00 ] The AI Edge by Jeb Blount and Anthony Iannarino | Kindle and Hardcover

About Michael O’Shea, CFA

Michael is the Director and Head of Private Wealth Solutions at Origin Investments, where he leads capital-raising initiatives, oversees sales strategy, and builds partnerships with Registered Investment Advisors to expand Origin’s investment platform. With more than 18 years of experience in real estate and capital markets, he has helped syndicate over $10 billion in commercial real estate investments, including $500 million in 1031 exchanges. Michael holds an MBA in Finance and Real Estate Investment from DePaul University, graduating summa cum laude, and is a CFA® charterholder. He lives in Elmhurst, Illinois, with his wife Lauren and their three children.

Connect with Michael