3 Signs You Should Leave Real Estate (And When You Shouldn’t)

Mike DeHaan: [0:00] Times kinda suck right now, but that is what it is. I also know people that are absolutely crushing it that are making boatloads of money, and a big reason is because most of the industry has left. What's going on, guys? Welcome to today's episode of the collecting keys real estate investing podcast. We are, I guess, listening to this after Thanksgiving, but we recorded this during the Thanksgiving week. And so due to scheduling, family, commitments, whatever, we didn't have a chance to record as our normal little group. And so you're stuck with a solo episode with me today. This is your first time here. My name is Mike DeHaan. I'm the typical main host of the show. And Dylan and Dan, they were doing stuff this week. And so got a little, little deep dive into a blast from the past with another sort of, like, Friday focused style of episode with just me. And so you've been listening for a while. I used to do these sort of, like, single solo episodes once a week. Stopped doing this a little while ago. And, yeah. So it's, it's been a little bit. So if I'm rusty, I apologize. But, anyway, I'm gonna dive into a little bit of a topic that has been sort of a recurring theme in people that have asked me questions on Instagram or even just people in sort of my general circle around specifically quitting real estate and quitting your business and kind of, like, why people do that. Is this a good time to do that with how the real estate market is?

Mike DeHaan: [1:17] And I think I've been getting asked this a lot for two main reasons. One, first off, if you are new to the show, Dan and I, we actually sold our wholesaling and flipping business at the beginning of October. And so we have basically left that game to focus primarily on our private money and hard money lending business, Sir Lends a Lot or SLA Capital. And then also too, just because of the economy, we are seeing a pretty big influx of people that are kinda leaving the off market real estate, wholesaling, and flipping industry, both just kind of in a macro level on social media, you're seeing a lot, but also in our small little, scale group, you are seeing people that have been reasonably successful over the past few years that are actually going do other things. And so a reoccurring question has been, you know, should they be considering the same? What are kind of like the things that you consider when doing that? And so I figured for the sake of this episode, it would be just an interesting conversation to have to sort of like dive down to what it looks like to leave the real estate industry and when you should do that. And so what I'm gonna do is I'm gonna basically focus on when you shouldn't quit, like, when you're probably doing a little preemptively, when you should quit, and sort of, like, the sides you can look for. And then if you do decide to quit the real estate industry, kind of, like, how to do that and the ways to approach it so that you're successful in your next endeavor. So kind of the three different phases I talked about today is those who shouldn't quit, those who should, and how exactly to do it if you decide to take the leap.

Mike DeHaan: [2:44] And I'll kind of just point out a few different patterns that I see here and there on people that kind of go one way or the other and give you my opinion on them. And so first off, we'll start with people who shouldn't quit their real estate business, which I would say, honestly, most people fall into this. They just maybe are a little bit impatient with the way that things are going. And so people that shouldn't quit their business, would I say the number one people that are probably considering it that probably shouldn't do it are, like, newbie newbies. Right? So people that have just started dipping their toes in real estate. They're brand new to it, and they're considering quitting because it's hard. They're not getting anywhere as fast as they feel like they should. And to those people, I hate to break it to you, but this is what being a business owner feels like. If you were, like, new in the phases of real estate, you probably shouldn't leave it unless you've been fully committed. And I mean, like, full time, not like you're doing an hour a day or, you know, you listen to podcasts and you're sort of, like, looking for deals, that doesn't count as being a real estate business owner. But if you are full on into it and it's been, two years and you really, really find yourself struggling, then maybe consider it. But otherwise, if you're like a a newbie who's kinda just trying to figure it out, stick with it because you haven't actually developed any skills yet, again, translate to anything else. And if you go and try to go to some other kind of business, you're gonna fail as well. You're gonna struggle.

Mike DeHaan: [3:59] It's gonna be exactly the same. Okay? And so those people shouldn't quit. Also, people who have been running their businesses like amateurs over the last little while. And so I'm talking about people that kind of have, like, bad habits around their business, people that aren't using their CRM correctly, aren't tracking their KPIs, aren't hiring out and delegating the parts of the business that are repetitive and take a lot of their time, people that are spending their Fridays and Wednesday afternoons playing golf instead of working and then are just complaining that I'm making more money. All those kind of people probably shouldn't quit because honestly, dude, you're kind of treating your business like you're, I don't say like a loser, but you're you're doing it poorly. Right? You're not being a professional business owner. Those are like the same kind of people as the ones who complain that they never lose weight, but then they only go to the gym twice a week. You know, they skip their extra sessions with their trainer that they booked, and then they eat a bunch of junk food and stuff on the weekends. Like, yeah, no shit. You're you're only going in like halfway there, so you're not gonna get the results that you want. Same sort of principles apply to business. Right? And then the last sort bucket of people that probably shouldn't quit are people that just generally are looking around and have FOMO of the, quote, unquote, other success they're seeing people having, whether that's, you know, you're down the rabbit hole like the Cody Sanchez and buying other businesses.

Mike DeHaan: [5:12] You hear us kinda hit on that whole fad a lot. Whether it's people that are, like, looking at crypto or trading stocks or just, like, starting up, I don't know, something ecommerce, whatever. If you are looking around and you just feel like other people have it easier than you, you need to look at it from more of a honest perspective. Right? It's like, a, are those people actually successful and, you know, they are doing something that you're not and that you don't know? Or b, do they kind of just have the experience you have in real estate and it just happens to be a slightly better time for that kind of business? Right? And both those options are probably true. But thing is if you're acting out of FOMO, you'll probably switch over there and you'll struggle. And so it kinda just goes like stick with what you know. Right? And ultimately, a big Alex Mosse quote that I like is that business isn't a game of best man wins, last man standing, and that can apply to this scenario. Exactly. Right? And so those are kind of people who shouldn't quit. Newbies, people who aren't running the businesses very well, people with FOMO. Right? So you fall into those camps, kind of just stay where you're at, you know, maybe analyze your business, see what you can do better, and focus on how to sort of grow and expand your business, and then go from there. Now for people who should quit, like Dan and I did, right? We did decide to make a pivot.

Mike DeHaan: [6:25] But we fall pretty firmly into the first sort of category here of people that should consider quitting their businesses. And for us, that was we had a 100% confirmed option that was better aligned with kind of where we wanted to go, and that we already knew had more potential because we had already been growing it, right? And so for us with our lending business, we've been lending for three years and we had started hiring staff and building out systems at the beginning of this year. And that business was growing at a rate that just massively was starting to outpace our real estate business with its current state. And the upside seems so much higher. And not only that, but just because just with us being like a little bit burned out of dealing with crazy sellers, deals going sideways, the buyer struggles, you know, spending the marketing, all that sort of stuff. It just made sense for us to sort of go down this path. Okay? And so when we quote unquote quit, it wasn't like we're quitting and starting over. We're basically just stepping away from something that was reasonably successful and going full force into something that we knew had legs. And so if you are in that same situation, I would definitely consider if you have something lined up. But if you don't really have a confirmed option, maybe, like, wait a little bit. Right? The second sort of people that should look at quitting will be people that are, like, super overleveraged or have had some major losses. Know it sucks to go out when you're behind, but sometimes that is the responsible thing to do.

Mike DeHaan: [7:47] Especially in some of these markets right now, Florida, Texas, some of the markets where people are really far behind. If you are to the point now where you have used your HELOC on your home, you've used up your cash, your family's livelihood is getting a little bit dicey, it probably makes sense to throw in the towel, stop spending money on marketing, stop trying to earn your way back, and just figure out how to deal with the challenges that you're currently facing. Right? Not doing that is kind of the same as if you're at a casino and you're playing blackjack and you lose, you know, you're down a thousand dollars. You keep gambling and trying to win your money back? Like, no. You don't. Like, you have more control in business, sure. But also, you kind of need to be realistic if you look at, like, the big picture of the economy, what situations look like. Like, how much more risk are you willing to take on and try and dig yourself out? And if it's a situation where, like, you're honest with yourself and you are really really far behind, it probably makes sense to either pause, go to something else, go get a job, even though that sucks. That sometimes that is the best option for people. Go go back to a w two and just do anything different. Because especially with real estate, it is a debt heavy, risk heavy business. And sometimes it makes sense just to walk away from that.

Mike DeHaan: [8:48] Okay? The third people are if you look at kind of like the big picture of who you are and where you're at, and let's say you've been doing this business for a while, and honestly, just realize that you aren't as good as you thought you were. And it seems like kind of a weird one, but we've gotten to see quite a few people like this over the past couple of years that absolutely crushed it in, 2020, 2021. They were heavily boosted by the economy and how real estate was that period of time. And now stuff has gotten harder. They found it harder to keep up with the systems, to keep up with the hiring, keep up with everything that they need to learn and maintain that sort of knowledge they need to maintain around transactions, different strategies to keep a competitive advantage. And there are people that just look around and go, you know what? I actually don't think I'm not good at this. I'm not good at like compiling the data or running a sales team or being able to analyze, like, the macro trends to make the best, sort of decision with my business. And if that's you, it might make sense to go and do something different or to just scale down. Right? And just focus on being a business for a little while that maybe does a handful of deals a year, make them bigger deals. Like, don't try to, like, grow a business quite as aggressively. And that's always a hard thing for people to admit. But if you're able to look at your metrics, if you, like, are constantly looking around and trying to figure out what other people are doing and you realize that you were just falling behind, maybe it is time to go and do something else.

Mike DeHaan: [10:08] Okay? And so those are the people that potentially should move away from it. And so like, let's say you fall into that bucket, the next question comes down to how exactly do you go about it. Right? How do you actually pull away from real estate, especially if it's been a big part of your identity? This only honestly was a big thing for us was we have this podcast, we have this brand, we have this whole community that we ran. Dan and I had been doing that real estate business together for six years, 2019. Yeah. So solid six years. Right? It was a very difficult thing for us to do kind of because it was ingrained in who we were. And so if you are going to step away, you kind of want to make sure you're doing it the correct way so you don't, I don't know, suffer an identity crisis or sort of burn all your bridges. Right? Or go into a position where you're just equally as unhappy or equally struggling. And so if you are going to quit, think the first and most important thing is you go into something that actually does like fire you up and that you're excited about. I think one of the biggest mistakes people make is they leave one business to go to another business purely because they think it's a better opportunity when they're not that excited about it. Right? Like if you are a tangible sort of asset guy and you're really into real estate and doing renovations and all sorts of stuff, and you try to go into doing what we're doing, where we're basically just trading paper and generating debt, it's probably not gonna be that fulfilling because you are losing all of the actual tangible nature of real estate is is in the asset. Right? And all of a sudden, if you guys go to like, kinda like digital world, you're probably not gonna like it as much.

Mike DeHaan: [11:39] Same if you were like a real estate sort of like trades guy, and all of a sudden you decide you're gonna go and try and acquire a SaaS business or like run an accounting firm or something just because some friend that you had made a bunch of money doing that, you're probably not gonna make it because you're you likely just won't be as excited. It can be so far removed from what you've already been doing. And so if you are gonna make the leap, make sure you're pumped about it. Right? And if you don't know what that is, let's say you're in the camp of you're leaving because you're cutting your losses, spend some time to find that thing before you go all in on it. Right? And don't just chase an opportunity, but chase something that actually will get you going and get you excited to start working again. Okay? Second thing is when you're going to quit, I always really encourage people, and this is kind of along the same line, but make sure that you leave and go into a business that's like somewhat similar. Right? So like if you are leaving the real estate business and you decide you're gonna go into like ecommerce for, I don't know, Lego, drop shipping, some kind of product, it's going to be a much harder transition. You're gonna be starting from a much earlier phase than you're probably used to, especially if you've been a real estate business owner for a while. And that can be really, really hard. And you'll probably go back to that phase of like, you're losing a lot of money. You have a really major learning curve.

Mike DeHaan: [12:54] You're really kind of on the struggle bus for a while. And unless you crave that, I typically recommend you don't do that. And so things that are very good sort of tangent businesses to real estate, you know, lending, that's why I went to it. Things like title companies, things like contracting companies, different trades. I know people that have left the house flipping game and have gone and just taken their crews and just started doing renovations for people that are like homeowners. Right? Landscaping company, fence building company, stuff like that. Those are very, very good businesses where you have the same general skills. And especially if you've been a direct to seller real estate investor, which was nice, you probably have a lot of those skills around direct mail, around cold calling, around door knocking, around how to analyze opportunities. They're very, very similar in a lot of those home services businesses. Right? And so focusing on some of those, I think can be a good tangent opportunity. But don't go and like try to do something that's completely out of left field just because it, again, it seems like a better opportunity. Right? And if you do something that's kind of along the same lines, it will be a much smoother transition, no doubt be successful.

Mike DeHaan: [13:54] So really make sure you consider that when you're making the leap. And then the last sort of thing I want you to make sure you consider when you're going to quit is whatever you do, you got to make sure you go all in with it and you're prepared to work. Right? I think one of the biggest mistakes people tend to make is they shut down a business, they go into something else, and they treat it like a startup again. They go back to like days when they first started their real estate business where kind of just like clicking around, trying CRMs, you know, they're going to coffee meetings. They kind of like have their chosen. They're afraid to spend any money on anything. That's a giant waste of time. And if you've had any sort of success in your real estate business, you're doing yourself a disservice as a business owner and as an entrepreneur by not going all in and being willing to invest in yourself, invest in your business, hire staff, build systems. You know, you should be able to scale relatively quickly. It's not uncommon for people to you know, that have had some sort of successful business, say they run a million dollars million dollars a year in their real estate business, and it took them two years to do that. You go into a new business, you kinda know what you're doing from the ground up. You can build a more solid base. You can build systems and hire staff earlier. You'll probably get to that same size of business in like a few months, honestly, maybe six months.

Mike DeHaan: [15:03] Right? And even like faster than that, you'll start to find that the ceiling is much higher because you're not constantly, like, patting things on to a business that was already kind of fractured, and you're bringing that experience from that first business that you're leaving into something else. You're able to scale it a little bit more soundly, right, with a little more strategy. And so if you are making the leap, leave real estate altogether. Right? I still get people asking me all the times like, well, would you still flip a house if one came across and you liked it? And no, I wouldn't because that's gonna distract me from the lending business that I'm fully focused on. Right? I'm not buying rentals anymore. I'm not flipping houses. I'm not wholesaling anything. Even these different opportunities pop up and they actually have over the last few months, I just don't care because I'm all in on the lending business. Right? And I think if you wanna be successful, you kinda have to do the same thing. And if you are kind of trying to hold on to that real estate identity, you'll never really do anything with it. K? You'll never, like, quite be able to grow out of it and move on to the next thing. Like, if you're gonna do that, just stay in real estate. Yeah. Times kind of suck right now, but that is what it is.

Mike DeHaan: [16:03] I also know people that are absolutely crushing it that are making boatloads of money. And a big reason is because most of the industry has left. K? And that's okay. You just gotta, you know, compete with those people or be okay just kinda being a little bit smaller for the next little while and wait for the next wave to come. But and it's kinda like my view on if you should leave, what it should look like, the sort of things that I considered, I guess, as I as we were starting to make the leap. Ultimately for Dan and I, like, the biggest thing I see Dan and I, we put us on a bot. The biggest thing for me with walking away is I've said from the very beginning that wholesaling and flipping houses and buying rentals was a means to an end. And so when I started in that business, you know, honestly, before I started working with Dan back in 2018, my goal was to be able to make enough money so that I could kinda do what I wanted. And wholesaling and flipping houses is an awesome business for that. Like, as a very lean operation, you can make several $100,000 a year. You can buy discounted assets that build wealth. You can do all kinds of different things. Yes. It has downside risk, but it also has a lot of upside that is asymmetrical for the amount of effort that it takes, honestly, compared to other businesses.

Mike DeHaan: [17:11] And so that was my goal was to be able to make enough money, build enough of a knowledge base, we'll do something else. And that's what I did. And so when I got into 2025, I mean, honestly, the beginning of the year, Dan and I, we shut down our national wholesaling company. And we kept doing it local primarily because we had a couple other partners that wanted to run it with us. And so our plan the entire time was to basically provide them the back end. They would do a lot of the front end. Turned out that we weren't very good culture fits together. And so Dan and I decided to end that relationship. But on the side, we've been building the lending business because I had identified that as something that I was excited about. I liked the opportunity that was there. I liked the ability to have cash flow plus major upside potential, plus the industry is huge. So there is a huge huge ceiling. Right? And there's a ton of different people around it. And so that was what I decided to take the one that I made in real estate and apply it towards. You know, wouldn't you know it, we have grown extremely rapidly this year. We're already churning out regular months that are larger than a lot of our regular months have been in the real estate business over the years in terms of revenue. And we haven't even started to like feel like we've reached the ceiling yet. And so because we're able to come in, apply this money right away, apply the skill set right away, we've been able to identify an opportunity that much more better aligns what we wanna do. And so when it came to the real estate stuff, I was so honestly removed from that anyway, that it was a relief to be able to finally pull the plug.

Mike DeHaan: [18:33] And I would say the reason I kinda kept with it for most of 2025 was because I didn't really have proof of concept for lending yet. We hadn't really scaled it, and also it was a big part of my identity with having the show and everything else that I'd done. K? So, anyways, guys, hope you found it interesting. If you are considering leaving the industry, love to hear about your reasons why. You can message me on Instagram at Mike underscore invests. Shoot me a note there. I always like chatting with people. And, thanks for listening, guys, and I hope you had a great holiday. And we'll talk to you guys next week. This episode is sponsored by Sir Lenzelot LLC, also known as SLA Capital, which, if you didn't know, is Dan and I's private lending company. So, yes, we are sponsoring our own show, but what you're do about it? It is our private lending company that offers hard money and DSCR loans to real estate investors of all types. So you can be a new investor, an experienced investor. You can be buying flips. You can be buying rentals, whatever. We can do everything. And not only that, but the rates that we offer are just as competitive, if not cheaper, than pretty much every other company out there. So whatever big company you've been working with, bring us their term sheets, I guarantee that we can probably beat it. We have the same connections they do.

Mike DeHaan: [19:37] We just don't have all the overhead and middlemen. So if you wanna come and check us out, go to slacapital.com/keys, and I will know that you came from the show. And by seeing that you came from here, when you get the closing, you will save $500 on your first loan with us. So slacapital.com/keys, we would love to fund your next deal. Thanks for listening, everyone. If you want more from us, you can shoot us a follow on Instagram. I am at Mike underscore Invest. Dan is at Investor Man. Dan and Dylan is at Dylan underscore does underscore deals. Choose to follow and send us a DM to let us know what you think of the show.