Buying Real Estate Was My Worst Financial Mistake

Rashad Bilal (0:00)

Put it in chat, but Ish, we gotta have a conversation. Me and you gotta have a conversation.

Troy Millings (0:04)

And Ian, I want you to take on this, too.

Rashad Bilal (0:06)

The time has come, because let's have this, talk about having uncomfortable conversations.

Stocks is a better wealth building generational tool than real estate, and it is by a long shot. Real estate has drained a lot of people financially, and real estate so far has been my biggest mistake as far as this dumbass home that I'm building.

Ian (0:30)

You're going to quit saying that too.

Troy Millings (0:31)

I'm not.

Ian (0:32)

No, no, no, no, no, no, no. I should have made a call in July after.

I know.

Troy Millings (0:37)

No.

Rashad Bilal (0:38)

Listen.

Ian (0:38)

Rashad, Troy, Troy, I'm pouting.

Troy Millings (0:41)

I'm pouting.

Rashad Bilal (0:41)

I'm pouting.

Troy Millings (0:42)

No, no, no.

Ian (0:44)

Not when they get to clipping.

Troy Millings (0:45)

When they get to. Yo, let me ask you. No, you're not. Let me ask you two things. I'm going to ask you two things.

When we say stocks is a better financial vehicle than real estate, are we talking about for the common man?

Rashad Bilal (1:02)

Yes. Yes.

Ian (1:04)

And I don't want to have this conversation. I've avoided this conversation with you for three years. Yes, in terms of return on cost basis, short term, long term.

Troy Millings (1:12)

It's not true.

How? I'm about to tell you why.

Ian (1:16)

How?

Troy Millings (1:17)

I'm about to tell you why.

Ian (1:18)

I'm pouting.

Troy Millings (1:19)

Can you start talking about the common man doing it on their own?

Ian (1:23)

They don't gotta do it on their own. They got me. If I made you money, please put yes in chat. I don't even want to do this.

Troy Millings (1:27)

And that right there is not the common man. And that's my point.

Ian (1:30)

How?

Troy Millings (1:31)

I'm talking about somebody, look, somebody doing this on their own, not somebody that has a financial advisor or somebody that's telling them that reads charts like it's fucking ABCs directing them where to put their money. Index funds. That's not the common man.

Ian (1:45)

The average person can invest in an index fund or ETF.

Rashad Bilal (1:49)

10 years ago, 15 years ago, I would say you're 100% right.

Troy Millings (1:52)

And I was about to say that too. No, you took the words out of my mouth. Lately, these markets have been some...

Ian (2:01)

Some of the highest alpha generated markets of all time.

Troy Millings (2:05)

So now that conversation has shifted. But historically, you can't tell me that the stock market was giving you 9,000,000% returns on your money.

Rashad Bilal (2:18)

Historically, the stock market has outperformed real estate.

Troy Millings (2:21)

If a real estate investor made 15% on their money, they jump off a bridge. Let's be clear.

Ian (2:26)

Then you should come over the indexes.

Troy Millings (2:27)

Let's be clear. If a real estate investor made 15% on their investment, they would jump off a bridge.

Rashad Bilal (2:32)

So how much is a real estate investor making on their investment?

Troy Millings (2:36)

It depends on your region. Number one, it's regional.

Rashad Bilal (2:38)

Okay.

Troy Millings (2:38)

So I don't want to... New Jersey?

Rashad Bilal (2:41)

Yeah, New Jersey. New Jersey.

Troy Millings (2:43)

Couple hundred percent?

Rashad Bilal (2:45)

A couple hundred percent.

Ian (2:46)

Over what time frame?

Rashad Bilal (2:48)

What's the time frame?

Troy Millings (2:48)

A year. Give me a flip.

Rashad Bilal (2:51)

Okay.

Ian (2:51)

Okay. What about Midwest? Let's take Cleveland, Chicago.

Troy Millings (2:56)

Their numbers...

We gon say Cleveland. I'm a little familiar with Cleveland. I can't say Chicago, I can't say these other areas. Today, 2026, you could go buy a two-family house in Cleveland for 15 grand. That's your buy-in.

Rashad Bilal (3:08)

Okay.

Troy Millings (3:09)

You can sell said house for $90,000 in less than a year.

Rashad Bilal (3:13)

Now, let's...

Troy Millings (3:15)

And you could put 15 in it.

Rashad Bilal (3:17)

Let's break this down, because you said something like there's a barrier of entry that's difficult for people to get into the stocks. I would argue that it's way more difficult to get into real estate. Let me finish. All you gotta do is... You don't even gotta watch Market Mondays. You just gotta have a half a brain, and you can easily open up a Robinhood account, or eTrade, or any brokerage account, and you can invest in QQQ, which gives you all the technology companies. You can invest in the S&P 500, and you can put $500, $1,000, and whatever you can put in.