BiggerPockets Real Estate Podcast - How to Fail at Real Estate Investing in 2026
Episode Date: May 1, 2026If you want to generate passive income with rental properties, reach financial freedom, and make the most money with the least stress, do not do any of these six things. There are six ways to fail at ...real estate investing in 2026, and if you get even a couple of these wrong on your first or next deal, you could be out of the game for years to come. Trust us, we’re now dealing with five-figure emergency costs because we didn't follow the tips we’re sharing today. Both Henry and Dave have reached financial freedom in around a decade by doing real estate the right way. But that doesn’t mean they haven’t made very costly mistakes. Whether it’s tenants, repairs, using the wrong calculations, or waiting to talk to this specific person, there are a few crucial landmines to avoid on your next investment property. So, we’re going through the six ways to fail at real estate investing. If you do the opposite of these six, you’ll make money faster, with way less stress, scale smarter, and probably reach financial freedom even quicker than Henry or Dave. In This Episode We Cover What Dave does every single time before he hires someone to work on his rental The one mistake that led to an $80,000 (that’s right) repair bill The wrong way to calculate “cash flow” that will have you losing money every month Why most new investors waste months or years by not talking to these two people Are home inspections really worth it? This is who should (and shouldn’t) pay for one The one true way to tell if a tenant will be a great renter or a nightmare And So Much More! Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/real-estate-1272. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
Transcript
Discussion (0)
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.
We've all been there, dude.
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 life.
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? 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.
Yeah, that'll be exactly what happens. You'll be the first person.
to ever do that, but maybe at least reduce the amount of mistakes that you make.
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 screwups won't be as
impactful by learning from knuckleheads like Dave and I. 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. 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.
The number one way to fail in real estate is overly trusting other people or random people.
Just trust no one.
It just, yeah, I know it sounds incredibly cynical, but I am not saying that there are some
people 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.
There's 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. 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 skeptical, 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. 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. It is a pain in the butt. Yeah, it is. But it is so worth it. And 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 tradesperson and they show up,
they give you a quote and you're like, oh, 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 in your business. All right. So then what's number two? What is the number
two way to fail in real estate? Man, Dave, I remember as I was getting started in real estate
and I was seeing the things that people were buying and hearing how people were making this calculation.
And I just remember thinking, this is wrong. Why do so many people do this? And that is,
calculate cash flow the easy way.
In other words, they would just take their mortgage, subtract that from the rent they get,
and tell me that's how much cash flow they were making.
The amount of people that were doing this was just mind-boggling to me.
It's crazy.
The conversations I would have with people.
Oh, the agents too, everybody.
This deal cash flows $1,000 a month.
Your mortgage will be $1,000.
the rents 2000 and I'm like, this is wrong.
Yeah.
That is not cash flow.
What you want is net cash flow.
Rent minus mortgage, minus taxes, minus insurance, minus expenses.
All expenses equals net cash flow.
All expenses includes things like vacancy, not just maintenance and repairs.
Calculate vacancy and calculate real vacancy, not calculate, you know, I put 3% for vacancy.
That won't cover one month's rent.
You need to figure out what does two to three months of vacancy look like.
Be realistic with your expense numbers.
Underwrite them so ridiculously conservative that if you're cash flowing on top of your underwriting, it's a bonus.
because you're obviously hopefully going to perform better than that than the other expense.
The other one people love to leave off is property management.
I'm going to self-manage.
Yeah, you may.
You probably are until you get to a certain point or until your job changes or until your
spouse is like no more self-managing.
You don't know how long that's going to last.
Calculate management fees so that when and if you decide not to be your own property manager,
you don't give away all your cash flow because you didn't under.
right properly. You want to ensure the highest probability of success underwrite conservatively. And then
you'll know what could happen and the downside because you're underwriting for that. You're saying,
hey, what if things don't go well? That's why you have a vacancy contingency. What if rents aren't
what I thought they were going to be? You already know what that's going to look like.
To me, the only times I've ever really gotten like upset about a real estate deal is when I didn't
see the risks coming or didn't account for them. I personally, I don't know about you, I don't
get upset. Like, if I'm like, oh, you know, there's a vacancy for a month, it's like, yeah,
I plan for that. That's fine. It's frustrating. I'd rather not have it. But, you know, I planned
for it. Or maybe, you know, the rent comps were $1,500. I got $1,400. It's like, okay, I plan for
that too. I underwrote for that. And I actually put all of the line items in my underwriting
like, and reset, vacancy, capax and all of these things drives me absolutely. It drives me absolutely.
insane to say people say they're getting 10, 12 percent cash on cash return when they're just not
counting half of the expenses. I think what makes it challenging is when you do underwrite
conservatively and you start making offers based on those conservative numbers, obviously the
offers that you're making are lower than what maybe some other people are offering. And then you
start to get beat out on deals that you really wanted. And that's when people make the mistake.
That's when they start going, oh, well, I can come up 10 grand on my offer. Oh, well, I can
come up 20 grand. I'm tired of losing out on these deals. It's not the initial underwriting. It's the
monotony of making several offers, not getting a yes so that you're like, well, these other
investors seem to be doing it. They're paying a little more. So maybe I'm missing something.
I'm going to pay a little more because I feel like I'm missing out on deals.
Totally. You're not missing out on deals. What you just signed up for is losing sleep.
This is a hard balance to strike because we also say on the show all the time.
We're like, go out and get your first deal.
Just like go do a deal.
That is true.
You should go do that and not expect a home run.
I think like that's kind of the point.
Like you can't analyze your way out of any risk.
You can't analyze your way out of uncertainty.
But you need to analyze your way out of the big risks, the known risks, the known things.
that you have some control over, which are things like doing your numbers right and your rents
and your vacancies. When you find a deal that works with all of those things, that's when you go
execute. Don't just go out and buy anything, but also don't expect to find some perfect deal
that's going to have every number perfectly lined up for you and you're never going to have
any chance of failure. That's also not going to happen. All right. Obviously, I think these are great
points. But I'm curious to know what you think the third best way to fail in real estate is, and we'll jump
into that right after the break.
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All right. We are back on the Bigger Pockets podcast and Dave and I are talking about how you fail
in real estate in 2026. We've already covered Dave's number one way to fail, which is don't
trust anyone. And my number one way to fail, which was the second item on our list, was to stop
calculating cash flow the easy way and just subtracting your mortgage from the rent.
calling it cash flow. So Dave, what is the next way people fail in real estate?
The number three way to fail in real estate is not talking to a lender or agent until you're
quote unquote ready to buy. I get it. I know people want to think about the end in mind.
They want to create these businesses and have a perfect business plan. But you need to go
in a logical order of operations to get to your first deal and talking to a lender and talking to
an agent, even if those conversations go poorly, is an absolutely essential, I don't know if you call it
first step, but it's in the first two or three steps to being a successful investor.
And if you don't do this, you will fail, right?
Like, you're not going to get a deal if you're unwilling to talk to agents and lenders.
What I would add to this is talk to more than one.
every lender is a little bit different, especially if you're talking to local community bank lenders.
And also, I think people just have a lack of understanding of exactly how many different types of loan products there are.
So, yes, go talk to a lender and find out how much you're qualified for, but be specific and ask them, hey, are there any types of loan products that are specifically for the kinds of deals that I'm doing?
Or are there any kinds of loan products that are new or that are coming out soon that I need to be aware of?
What about asking them for down payment assistance programs or grants that are available in your area?
Because that might mean you're eligible or can borrow more or have down payment assistance that you never knew about.
Absolutely.
And lenders will talk to you as if they speak for every lender.
So don't take what they say as the holy grail of getting a loan.
Take it, write it down, take the notes, and then go talk to another one.
You'll learn something different.
But the more lenders that you talk to, A, the more you can prepare yourself, and B, the more
information you'll have about what types of loan products are out there.
And then the other key with this, guys, is it will help you figure out what it is that you need
to go fix if you're not getting the answer you want.
Yep, exactly.
Don't just get a no or get a, hey, we can't pre-qualify you or, hey, we don't think you're
ready, ask them why. What is it that I need to fix? What would give you more comfort to lend to me?
So that now you at least have a plan for what to go fix to make you more bankable.
All right. Well, that was the number three way to fail in real estate. Henry, what is the number four way?
This is especially if you're new, not getting an inspection.
Oh. And I know that's a lot for me to say because I do not get inspections when I buy
probably is now. Really? I've always gotten an inspection. Yeah. Well, you buy mostly on the market, right?
Yeah, and I don't flip. I buy off market and I typically don't get inspections because I'm
experienced enough now to walk a property and feel comfortable on whether that thing is going to cost
me a ton of money to fix. You're your own inspector. I'm my own inspector at this point.
But it takes a lot of looking at houses, a lot of buying houses, a lot of renovating houses, and a lot of
dispositioning those houses before you can feel as comfortable as I am doing that. So if you are not in
that boat, you better be getting an inspection. You just don't know what to look for. And there are
things that you can miss with the naked newbie I that can literally price your deal out of being
profitable and put you in a very tough financial position. It's a few hundred.
$500. Spend the $3 to $600 and sleep better at night. It is well worth it. Even if you get that
inspection report back and there is nothing wrong, good. That's what you wanted. I will pay
$3 to $600 for peace of mind all day long. There's no reason to do this anymore. Like during COVID,
I guess you could have made the argument that, you know, things were so competitive. And if you knew
you had a great deal, like maybe you waive the inspection. That has totally changed. Like,
Honestly, not only inspections help protect you, right now, they're one of the best ways to save money.
Like, most people are getting leverage during the inspection period and negotiating concessions
or discounts off of the sale price during the inspection.
So for most people, this is not going to be true for everyone, but you're actually going to
probably make money by having an inspection because it's going to cost you 500 bucks, but you're
going to have five grand back in concessions from the seller or they're going to fix something
that you would have had to come out of pocket for.
So I just like, there's no reason to do it.
The one thing I will say that I have done that has been pretty effective when I'm
trying to be aggressive about a bid is doing like a pass fail inspection where you basically
say, I'm not going to nickel and dime you on the inspection.
I'm going to get one.
And then I'm going to tell you if I'm buying the property or not.
But I'm not going to ask you for money.
Yeah.
No, we have done that in the past where we said, look, I just need someone to get eyes on this
property with a little deeper look.
I'm not going to ask you for anything.
I just need to know what's going on.
And I will give you a decision, buy or no buy right after I look at that inspection report.
Because you're right, a lot of the fear that sellers have with buyers doing inspections,
it's just that most people understand that inspectors are paid to find things,
and they're going to give you a list of things that they think is wrong with the property.
And then the buyer's going to want you to fix those things.
And that's going to cost them time and money.
But at the end of the day, if you're new in this business and you want to do an inspection
and you're dealing with a seller who does not want you to do it, walk away.
There's more deals.
Yep, totally.
Even if you think it's a great deal, don't take that risk because there's probably some reason.
And if they're not going to tell you what that reason is and they're not going to allow you
to at least get a professional's eyes on it, just move on.
There's other deals.
100%.
All right.
So there's my number four.
Make sure you get those inspections.
Dave, I'm curious to know what you think the fifth way to fail in real estate is.
But again, we'll find out after the break.
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All right. We are back on the Bigger Pockets podcast. Dave and I are breaking down our list of
ways to fail in real estate. We are working on number five. Number one, don't trust anyone.
Number two, stop calculating rent the easy way.
Three, don't wait to talk to lenders.
Talk to lenders as soon as you can.
Number four is not getting inspections.
That'll kick you in the teeth every time if you're new.
Number five is what, Dave?
All right.
This is a mistake I've made in the past.
I see it all the time.
But the number five way to fail in real estate is to not repair things properly and allow deferred maintenance.
to accrue on a rental property.
Are you talking directly to me right now?
I feel personally attacked right now.
My wallet is feeling personally attacked recently for some bad decisions I made about this.
People love buying, right?
It's fun.
You know, you feel good.
You get to tell your neighbor that you got more doors.
But man, the way you make money in real estate or you fail in real estate is how you
operate your business over time.
Acquisitions are important.
You got to do the underwriting, but a surefire way to screw something up is to ignore
what's going on at your property each and every day because these things compound. A problem that
cost $200 to fix, a year later will probably cost $2,000 to fix. I know this because I'm replumbing
a house that just cost me $80,000 to fix. Yeah, just pay the money up front. One of the reasons
you need to underwrite and have cash reserves is to pay for this stuff up front. There is no point.
If you're in your first or fifth or your 10th year of investing in real estate and saying,
you know what, I'm going to save 300 bucks and not do it right now.
You're investing for 10 or 20 years from now, 30 years from now.
Pay the money up front.
It is worth it every single time.
You know, meet with a lot of contractors, find the best person to do the job and just do the job.
There's two ways that this has bit me in the butt.
The first way is buying something that does need work that I planned on working on,
but there was tenants in the property.
Right? Oh, yeah. Oh, yeah. Yeah. So what that means is I bought it, but I didn't put the tenants out because they're paying decent enough rents. They've been living there. They want to keep living there. That's cool. They do. What is supposed to happen is when they move out, then you do the renovation. But what happens, guys, is you forget. By the time they move out, I'm flipping three houses and I'm renovating two other rental units. And you just forget. And it just gets.
It's re-rented.
And so now I didn't do the renovation, and it's lingered, and it's lingered, and the maintenance
bill start coming in, and this property is costing me a ton of money.
And I'm like, oh, yeah, I was supposed to spend $40,000 renovating that unit.
And I just didn't, right?
Bad operator problems.
I wasn't organized enough to be ready to jump on that renovation when it happened, and it
ended up costing me more money and maintenance along the way.
and I've sold properties because of that
because I just didn't get to the renovation in time
and now I'm at a place where I don't have the bandwidth to do it
and I'll sell that property and is that the right thing to do?
Probably wasn't.
I should have jumped on it right when I needed to.
But it requires you to be a good operator.
So that's one way it's bit me in the butt.
The other way is maybe you did renovate the property
when you were supposed to,
but it just got super maintenance heavy.
And when you have a bigger portfolio,
you get maintenance requests all the time.
And sometimes you're just approving things or you're not approving things.
And you don't realize like, hey, this is the sixth time I fixed something at this unit.
When you have 60 units, right, it's hard to sometimes remember that like, oh, I fix this thing at this place several times or I've spent money at this place several times.
And you realize that maybe this is a property that I should have stopped taking a holistic look at and figured out.
how much money do I need to spend to stabilize this thing or do I need to sell this thing?
Exactly.
I am guilty of these things.
So I am speaking from experience.
You've got to stay on top of your maintenance.
You've got to be able to look holistically at your properties and see how much you're spending on maintenance and do it more than once a year.
So you can recognize these trends before you get that $7,000 bill and make informed decisions.
But this is real.
This is real right here.
All right.
So that was number five.
But Henry, let's finish it up.
What's the last way to fail in real estate?
Number six on our list.
And one of the ways that can absolutely cause you to fail in real estate is not screening
your tenants.
Dave, it blows my mind when I talk to people who self-managed and I asked them, did you
call your tenants references?
Did you call your tenants past landlords?
Not just the one they just moved out of, but two landlords ago.
And they say, oh, no, we didn't do.
Like, I just, it blows my mind.
And I think it's because it's a tedious thing to do and calling random people sometimes
is uncomfortable.
Maybe that's why they avoid it.
But the amount of landlords that I talk to that don't call tenant references, that don't
call tenant employers and that don't call past tenants beyond just the one they just left,
it is mind boggling to me.
But our job as landlords is not to rent properties.
I mean, it is, but our job is to get really good at tenant selection.
If you want to make money in real estate investing as a landlord, tenant selection is the way you do it.
Because what kills you as a landlord isn't just bad tenants who hurt your properties,
but what really kills you is vacancies.
And so finding good tenants with a good history who want to be in your properties, like it's a skill set that you have to develop.
And part of that is due diligence.
And part of that due diligence is uncomfortable.
But it will literally put money in your pocket or keep you from bleeding money out.
Like it just mind boggling to me that people don't do this consistently.
Like you said, it's not just about limiting vacancies.
But when you have a good tenant, they're going to let you know about.
the problems. Like the stuff we were just talking about, like the repairs, like when you have a good
tenant, they're going to come to you and be like, hey, this problem is the issue. I really think we need
to fix this and this and this. And you trust that because you know them. You've screen them.
You have a good rapport with them. It saves on so many different things. I've had units where I've had
tenants move in for four or five years. You know, I'm not even talking about families. I'm talking
about young professionals. Stay for a long time. They take responsibility for the property. They
meet with contractors for me regularly because they're people that I've built a rapport with.
Like, this is a business. These are your customers. It is your job to be a good service provider to
them and find people who you feel like you can work with. It is a mutually beneficial thing.
This is someone's home. This is where they live. It matters to them. Find someone who's going
to treat it and think about it in the same way that you can. And you're both going to be so much better off.
The best screening technique that I have found for tenants, the thing that's usually worked out well for me, is calling tenants current and past employers and asking them what kind of employee were they?
Did they show up on time?
They'll tell you.
They're like, oh, man, this guy, they were always late.
They never did what they said they were going to do.
That feedback has always translated well for me.
And then one question I always asked them, as I say, if it was your house, would you let them,
live in your house. And if they've said no to that and I've let them live in my property,
I've regretted it. And if they've said yes to that and I've let them live in my property,
it's usually worked out pretty well. Yeah, I think this is just a no-brainer. It's honestly crazy
to me that people wouldn't do this. This is someone who's moving into your house. Like I dropped
my car off to get a tire repaired and I was like interviewing the person to make sure they were going
to do it. Maybe this is just me that I'm skeptical of everyone. Well, your number one rule was
don't trust people. So it is not a surprise.
This is said, I grew up in New York. This is such a good New York. Oh, that's so true.
That's not, I forgot about that. Yeah, that is very New York. New Yorkers don't talk to anyone.
They don't trust anyone. Yeah, it's just like, oh, you're talking to me? What do you want for me?
It's so New York. You're right about that.
No, but I really mean that. I just like, I think I approach it like in a friendly way, but I just want to make sure I know who these people are. Like, this is the, this is the challenge of real estate.
is you were working with so many people.
Yes.
Work with great people.
I am not saying don't trust people because most people aren't trustworthy.
I actually find that most people are trustworthy and most people do a good job.
But it is your job as the investor to make sure you screen out the people who are the exception to that rule.
And you make a good point that like typically once you get to the point of calling references,
you already have a pretty good idea if you want to rent to this person and you're doing some confirming.
So it's not like you've got to go do this for every applicant.
That is not what we're saying.
Once you've gone through your normal application process and you've narrowed it down to a couple of people, even if you've got that good feel, even if they've given you the good vibes, confirm those vibes.
If you've got the good vibes, somebody else should have the good vibes about them too.
And if what you're hearing doesn't fit the good vibes, well, you've got a hard decision to make.
But I'm telling you, when I have talked to past employers,
that is where I've got the best feedback.
All right.
Well, we've given you six ways to fail.
Any other last thoughts, Henry?
The last thoughts for me is a lot of these just seem like trust, but verify.
Verify these things.
You've got to do due diligence, not just due diligence about the purchase process,
but due diligence about the renovation process and inspection process and do diligence
about the tenant screening and tenant process.
These are the places that are going to make or break you.
These are the places that are going to either put money.
in your pocket or take money out of your pocket. And what can really hinder people, especially when
they're first getting started, is taking a big loss on your first deal. It can set you back years.
If you've saved up a bunch of money to finally buy a deal and you stumble on one of these six items,
it could set you back to where you've got to save up a whole lot of money again or just put a bad
taste in your mouth so that you don't end up investing and setting yourself up for a future of financial
freedom. So trust us. We're saying these things, not because they're trendy things to say,
but we've made these mistakes on some level. Dave and I have made all these mistakes.
Don't do it. Take that one extra little step when you want to quit and you're tired and you don't
want to make that extra phone call. That's the way to not fail. Like if you have to summarize it,
is just take that one extra step and you can be successful. Your chance of failure,
if you're willing to put in that little tiny bit of extra work is pretty low. So that I think is
is super encouraging. And I know it's going to be hard when you're staring at a deal that you think
could be profitable. And one of these things that we talked about just isn't computing. And you're like,
man, do I really want to walk away? Yeah. Yes, you do. Live to fight another day. There are more deals
to buy. Just don't bend on these six things. And it will keep you safe. It will keep you in the game.
And it will keep you on the path to financial freedom. Well said. All right, guys. Thank you so much for
joining us on this episode of The Bigger Pockets podcast.
Hopefully you have learned from Dave and I's mistakes or you will learn from Dave and
I's mistakes and it will keep you safe.
It's been great talking to you.
We'll see you on the next episode.
Thank you all for listening to the Bigger Pockets Real Estate podcast.
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I'm going to be the next.
