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Financial Freedom with Real Estate Investing

MB499: Swap Till You Drop: Building Wealth with Tax-Advantaged Real Estate – With Louis Rogers

Financial Freedom with Real Estate Investing

Michael Blank

Business, Investing, Entrepreneurship

4.7577 Ratings

🗓️ 24 November 2025

⏱️ 40 minutes

🧾️ Download transcript

Summary

What if you could build wealth through real estate… without paying taxes along the way? In this episode, Michael Blank welcomes Louis Rogers, founder of Capital Square and pioneer of the tenants-in-common model still widely referenced today. Lewis breaks down the simplicity of 1031 exchanges, why DSTs have replaced TICs, and how investors can eventually move into a REIT structure to enjoy completely passive investing — while still deferring taxes. If you want to learn how the wealthy use the tax code to accelerate their net worth, this episode is a must-listen.

Key Takeaways:

  • 1031 exchanges are simpler than most people think — and typically cost about $1,000 using a qualified intermediary.
  • The old tenants-in-common (TIC) structure is obsoleteDSTs are now the preferred option for 1031 investors.
  • Investors can move from active ownership → DSTs → UPREIT, getting more passive over time.
  • Tax deferral can continue for life — with a step-up in basis eliminating capital gains upon inheritance.
  • The U.S. tax code is uniquely favorable to real estate — wealthy families use it strategically.
  • Paying taxes is a choice: learn the rules and keep more of your money working for you.

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For full episode show notes visit: https://themichaelblank.com/podcasts/session499/

Transcript

Click on a timestamp to play from that location

0:00.0

Hey Dealmakers, welcome to the show where it's all by Financial Freedom with Real Estate.

0:04.1

Let's do this.

0:09.6

Stop paying taxes that you don't have to pay.

0:13.0

And what we're talking about here in the episode today is how smart investors swap till they drop to build wealth faster.

0:19.5

And today I'm hanging out with Lewis Rogers, founder of Capital

0:21.7

Square and author of Section 1031 exchanges, how to swap till you drop. Now, Lewis has been in this

0:27.1

tax advantage investment base for four decades. In fact, his company, he and his company,

0:32.1

invented the term tenants in common that we use today and take for granted. And it's helped thousands of investors

0:38.9

defer millions in capital gains. And we get into why 1031 exchanges are simple than most people think.

0:45.1

And one of the things that surprised me that I learned is that 1030 exchange, as we mostly know

0:49.4

today, using the tenant in common or the tick approachach is actually outdated in favor of something called a

0:55.2

dst. Well, what is that? You're going to have to listen to find out what that is because according to

1:00.1

Lewis, no one does a tick anymore. And this is surprising because that's exactly what we do. So very

1:05.2

interesting knowledge. I never heard that before. Also, he describes how you can go from a simple rental

1:10.2

to eventually exchanging into a

1:12.8

reet by changing the different ways to exchange. Absolutely fascinating. And so I never heard that

1:19.1

before either. And then he talks about some of the two biggest mistakes that he sees investors make

1:23.6

with taxes, plus what you can do if you've already kind of blown in exchange.

1:31.7

So if you want to understand how to use the tax code to your advantage at a very sophisticated high level in a way that's simple to understand so that you can build wealth faster,

1:36.3

then you're going to love this episode.

1:38.0

Let's get into it with Lewis Rogers.

1:40.7

Lewis, welcome to the show today.

...

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