How to Fail at Real Estate Investing in 2026

**Henry Washington** (0:00)
This is how you fail at real estate in 2026
Dave and I have more than two decades of combined real estate experience, and let me tell you, that means a lot. A lot of failures. I have a deal right now that I'm going to lose at least $10,000 on.

**Dave Meyer** (0:16)
We've all been there, dude.

**Henry Washington** (0:17)
But the good news is, we've learned enough to create an entire blueprint of real estate investing failures. Now, all you need to do is the exact opposite of these mistakes. The crazy part is, I still achieve financial freedom in less than 10 years, even with all those errors along the way. So imagine how quickly you could do it if you learn from these failures first.
What's going on, everybody? I'm Henry Washington, and I am joined by my co-host, none other than Dave Meyer. What's up, buddy?

**Dave Meyer** (0:49)
Not much, man. I'm excited to talk about this, because hopefully everyone listening to this could just do the opposite of all the things we've done wrong and just coast through real estate investing with no issues.

**Henry Washington** (1:00)
Yeah, that'll be exactly what happens.

**Dave Meyer** (1:02)
You'll be the first person to ever do that. But maybe at least reduce the amount of mistakes that you make.

**Henry Washington** (1:08)
If anybody tells you they've never lost money in real estate, either they're not doing deals or they're lying to you. What we want to do is be transparent, share with you the mistakes that we've made, so you don't have to make them, and hopefully that makes your journey a little bit easier. Are you still going to screw up? Yeah, yeah, you will. But hopefully those screw ups won't be as impactful by learning from knuckleheads like Dave and I.

**Dave Meyer** (1:32)
Losing a little bit of money on one deal or not being perfectly optimized is part of the game. The goal in real estate is just don't have a catastrophic error, and that is definitely possible.

**Henry Washington** (1:42)
Well, with that, let's jump right in. And Dave, I'm curious to hear what you think the number one way of how to fail in real estate is.

**Dave Meyer** (1:51)
The number one way to fail in real estate is overly trusting other people or random people.

**Henry Washington** (1:58)
Yeah, just trust no one.

**Dave Meyer** (2:02)
It just, yeah, I know it sounds incredibly cynical, but I am not saying that there are some people who are trustworthy. It is me just like not doing my due diligence on the people that I am going to be working with is probably the thing that has led to the most difficulties and losses in my real estate investing career.

**Henry Washington** (2:23)
There is some truth to this one. There is some, I hear you. And you know what I like about this one for real?
Is that when you're new, you depend heavily sometimes on other people's analysis and perspectives and opinions. And I think you do need to weigh those things out. But I also think you've got to get yourself to a place where you can do enough analysis on your own and feel confident in doing a deal based on you and not what someone else is telling you.

**Dave Meyer** (2:53)
I see this all the time. I work with new real estate agents now when I'm looking at new markets. And they'll send me deals. And probably earlier in my career, I would have just taken their word for what the rent comps were going to be or what the ARV of the project was going to be or what vacancy was in that particular area.
Now, I am much more sceptical. Not that they're always wrong, but I'll talk to several agents and really do my due diligence almost more on them than the deal. Especially if you're building a permanent team, like an agent or a lender. Like these are people you're going to work with a long time. You should be learning about them, calling references, calling other people who have worked with them and gotten their experience. Like, I know it sounds like a pain in the butt and it is a little bit.

**Henry Washington** (3:41)
It is a pain in the butt.

**Dave Meyer** (3:42)
Yeah, it is. But it is so worth it. I want to be very clear here that I am not trying to blame other people for my failures. It's my fault. I did not do enough due diligence. Or just as like the simplest possible example, if you were to go out and just use the first quote you got on any deal, like you call a contractor, you call a trades person and they show up, they give you a quote and you're like, well, that seemed reasonable, I'll take that quote. As we all know, quotes can vary by tens of thousands of dollars. So like those are like the basic kinds of things you need to do and not just trust that the first person that you interact with is the right person for you and your business. All right. So then what's number two? What is the number two way to fail in real estate?