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Real Business Owners

Building a $200M Portfolio with Justin Brennan | Episode 341

Real Business Owners

Trevor Cowley

Business

5704 Ratings

🗓️ 9 December 2025

⏱️ 96 minutes

🧾️ Download transcript

Summary

In this episode, Justin Brennan breaks down how he went from watching his family lose everything in a $60M bankruptcy to rebuilding a $200M multifamily portfolio. Trevor and Justin dive into the mechanics of commercial real estate, how to protect yourself in volatile markets, and the deeper psychological work required to level up in business.

This isn’t just a real estate episode. It’s about breaking generational patterns, rewiring the subconscious, and understanding how big players build, and keep, wealth.

If you are ready to level up personally and professionally, go to joinrbo.com

Transcript

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0:00.0

Being an entrepreneur sounds cool, but the reality of building a business is very, very difficult.

0:07.0

Every level that you hit, there's a lot of things that suck that you just won't want to do.

0:11.6

What you're capable of is on the other side I don't feel like it.

0:15.5

And if you're committed to what it is that you're trying to do, nothing is going to stop you from getting there.

0:24.1

Welcome back to another episode of Real Business Owners with myself, Trevor Cowley.

0:28.1

Today we have a special guest, Justin Brennan.

0:30.9

This individual has gone through a $60 million bankruptcy to building back a $200 million portfolio. He's the author

0:40.4

of the multifamily playbook. And we do have some mutual friends down there in the San Diego

0:46.3

area. Shout out to Rich Summers. And so I'm excited to get into this episode. I have a lot of

0:52.9

questions in regards to, you know,

0:55.0

the temperature that we're at in terms of the marketplace, right? Like some people are going to be like, hey, I'm going to stand on the sidelines, you know, wait for the market to cool off. Is that like your guys' approach right now? Or you just keep moving, keep moving no matter what. the record. So it was my dad's bankruptcy.

1:11.3

Okay. Not mine.

1:12.1

Okay. But I got to walk through it. He didn't make the bad decisions. He pulled them out of the bad decisions, I guess. Yeah, and it was during the financial crisis. I mean, I, I mean, there's some cool stories I can tell you about it. Just over leverage. Is it uh what it was yeah so i mean my um

1:28.0

come from a real estate family a bit you know my my grandmother god bless her soul a little

1:33.0

italian woman you know she was 91 but still driving around her little s10 Chevy truck

1:37.4

collecting rent from her tenants yeah and um you know she passed that on to my dad a little bit

1:43.7

um but my dad a little bit.

1:48.1

But my dad didn't grow up in, I guess, a good household.

1:53.4

I mean, I learned some things after he passed that I didn't know.

1:57.0

But so I knew that his dad died when he was three.

1:57.5

Yeah.

1:58.6

I just didn't know why.

...

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