JF 3906: Deferred Gains, Development Risk, and Diversified Portfolios ft. Michael O’Shea

The Best Ever CRE Show

Best Ever CRE

Realestatepodcast, Entrepreneurship, Business, Realestate, Investing, Realestateinvesting, Realestateinvestingpodcast

4.8 • 983 Ratings

🗓️ 15 May 2025

⏱️ 62 minutes

🔗️ Recording | iTunes | RSS

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Summary

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 Get a 4-week trial, free postage, and a digital scale at ⁠https://www.stamps.com/cre⁠. Thanks to Stamps.com for sponsoring the show! Post your job for free at https://www.linkedin.com/BRE. Terms and conditions apply. Try Huel with 15% OFF + Free Gift for New Customers today using my code bestever at https://huel.com/bestever. Fuel your best performance with Huel today! Join the Best Ever Community The Best Ever Community is live and growing - and we want serious commercial real estate investors like you inside. It’s free to join, but you must apply and meet the criteria. Connect with top operators, LPs, GPs, and more, get real insights, and be part of a curated network built to help you grow. Apply now at ⁠www.bestevercommunity.com⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	Ready to launch your business? Get started with the commerce platform made for entrepreneurs.
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0:12.4	marketing tools that get your products out there. Integrated shipping solutions that actually save you time.
0:17.4	From startups to scaleups, online, in person and on the go shopify is made for entrepreneurs
0:23.3	like you sign up for your one dollar a month trial at shopify dot com slash setup have you ever felt
0:31.5	overwhelmed trying to compare investment funds or figure out whether a tax advantage strategy
0:36.9	like a dST or opportunity zone
0:39.2	fund is actually worth investing in. In this episode of the Passive Income Playbook on the Best
0:44.6	Ever CRE show, we are unpacking the complexity with one of the most experienced groups in the
0:51.5	space. I'm your host, Pascal Wagner, and today we're joined by Michael
0:55.2	O'Shea, head of private wealth at origin investments, a firm with over $3.3 billion in assets
1:01.7	under management, 44 realized deals, and a reputation for delivering institutional quality investments
1:07.9	to individual LPs. We dive into their performance across multiple
1:12.7	fund vintages, including a 27.7 realized IRA on their 2011 growth fund, as well as what
1:19.6	it's actually like to be an investor in their DSTs and Opportunity Zone products. If you've ever
1:24.5	wondered how seasoned investors think about tax strategy, risk, and long-term
1:29.5	planning, or how to partner with a firm that's executed over $4.3 billion in transactions,
1:35.5	this one is for you.
1:37.3	So let's get into it.
1:38.6	Welcome, Michael.
1:39.6	Hey, Pascal.
1:40.3	Thanks for having me on today.
	...

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