You Said My Real Estate Business Was A Mess, Let's Talk About It

Added: 2026-05-30

[00:00:00]Posted a video saying that I had 90 rental units and that I still couldn't quit my job and the internet had a lot to say about it. Some people said I scaled too fast, some people said I had no idea what I was doing, some people said my numbers didn't make sense. And honestly, some of you are right, but some of you are very, very wrong. So, in this video, I'm going to walk through some of the major categories of comments that I got. We're at over 1,000 comments right now. I'm going to talk about some of the critiques that I agree with, and then I'm going to talk about what I'm going to do to move forward and make the business more sustainable and how I'm going to fix this mess. So, the first category of commentary revolved around me scaling chaos. One of the key points people were trying to make was that 90 doors and still working means something is wrong. And I think that for some people that there's a certain level of monthly income that just ends the game for them.

[00:00:56]They can quit, they can do whatever. But my lifestyle's a little bit different and I'm still growing businesses, I'm still involved in many other things. And in order for me to quit my job, that means that I I'm in a position to take my living expenses way down so that they are very predictable and very constant and it's like I have a young young family and I'm just not at a position to slow down and do nothing because I wouldn't want to put my family in a position where, you know, there's an emergency or something comes up that we cannot cover. So, I just don't feel like I'm in a position to coast. I do think though that at the number of properties that I have, depending on your lifestyle, you may be able to quit. I was think I was speaking about my own personal situation. So, some people took my statement to mean that nobody can quit once they get to 90 doors of real estate. I'm absolutely not saying that.

[00:01:51]It just depends on your threshold, your monthly living expenses, and what what you need to feel comfortable, what kind of buffer you need to feel comfortable without having any other recurring revenue coming in. But what I will say that I've seen firsthand is that more doors than not more is that more doors does not mean guaranteed freedom. And so certainly if I had to do it again, I probably would not have scaled as fast and I would have focused on getting consistent revenue and sustained maintenance processes with a smaller number of doors. Hindsight is 20/20.

[00:02:28]Proceed number two, you should have bought fewer higher quality properties.

[00:02:32]I think my properties were middle of the road. Not high quality, not super expensive, but then also not dirt cheap.

[00:02:41]And I think what I'm seeing now is that as properties begin to age, the equation changes. The equation changes, the maintenance load changes, the number of calls that are required on the property changes. And so at some point if you're involved in real estate, your property is going to age and it's going to decline. It doesn't matter high quality, brand new, it doesn't matter. At some point you're going to deal with that. Because I actually have properties that are brand new and we still get calls. I mean it's not as many, but there's still expenses and and you would think that there would be none with a brand new property, but it's not a fail-safe either. But my new take on real estate rental real estate is that and now it makes sense why people are selling off older properties because it's almost like the sweet spot is you get a property in decent shape, you run it into the ground, and then you sell it to somebody. And you let the new person try to get into real estate figure out how to update systems, get everything back up to snuff. There's always somebody who is trying to get in the game and when you're trying to get in the game, usually you're trying to preserve your cash, and you're trying to just get in the game by any means necessary. And so, I think that's what I would do going forward. I think I'm changing my mindset that you buy a property and you hold it forever, because if you want to try to hold something forever, you have to deal with it forever, right? Like, you have to deal with it aging, and you have to bake into your financial plan that I'm going to have to replace this HVAC system. I'm going to have to put a couple of roofs on this building. And so, I think when I first got into real estate, it was a very fantasy world that you buy and hold forever.

[00:04:30]And right now, I'm actually questioning the buy and hold uh philosophy now. Critique number three was that I don't have enough systems.

[00:04:38]And that one was probably true a couple of years ago, but now, I don't really touch much of anything. I have implemented Zapier automations. I have AI sending responses for me. So, now I'm really not touching so many systems.

[00:04:55]About a year ago, about a year and a half ago, someone said to me, they're like, "You have an engineering background. Why are you still allowing so many things to be manually run in your real estate business?" And at the time, I just had not made the connection that like, all this stuff that I'm doing at work, I should be implementing that in my business. And then, I just took off. I was like, "Okay, let's look at every single process and see where we can remove the human." And so, that's the journey we've been on for probably the last 18 months, and I think we're really down to a really good process, and I'm going to do a full video on how AI pretty much saved the business, because I was beyond ready to quit. And I think the the last 18 months, I've really seen a resurgence in my interest in the business, because it really felt like nothing but a drain at one point, and now I can kind of see the light at the end of the tunnel. So, everybody who said that I I didn't have enough systems, they were right to a point, but now I understand that scaling in the way that I did without the intent to automate was probably the initial flaw in my thinking. And it wasn't until my team and all the systems that we had in place really just started to break down, and as we asked everyone to take on more and more and more, everyone was at the wit's end of their patience, including me. So, that was really the light bulb moment that has even allowed us to get to where we are. So, what I actually did was I decided So, I decided that I actually needed to take a step back from running the business, and that hurt a little bit, but I said if I don't take a step back and focus on automating this and and getting things off of and taking things off of people's plate, this whole thing is going to burn out.

[00:06:44]I'm going to burn out, my team is going to burn out, and I can't run this business without any human support. So, I spent a solid month, maybe two, going through everything. What can I automate?

[00:06:56]How do I change this? You know, how do I move away from doing things one way because that's the way they've always been done. And I just kept changing process and changing process, and it was a nightmare for the team because you know, they'd be doing something one way, and then the next week I'd change it.

[00:07:13]And then I may change it again. But, I think now we're kind of leveled out where people understand how the systems work. When something goes wrong, they know where to go, they know how to troubleshoot things. And so, I definitely think having your systems in place is 100% something you need to do, especially if you're scaling. When I started small, I didn't have any systems. I didn't need them. And so, if you're just buying your first rental, like don't get bogged down with that. But, if you decide that you want to scale like I did, then you need to consider it. The next category of major comments that we got were around my people systems being broken. And so I think some people misconstrued what I was saying in that video because I was kind of critiquing property managers and in people's minds that became why are you self-managing 90 doors. When I what what I mean by self-managing is I don't have a third-party company running my business. I'm in charge of everything, but I do have a team. I have a maintenance manager who manages all the maintenance calls, all the unit turnarounds, anything that needs to happen in person or on the ground, I have a person to do that. I have a bookkeeper. I have a person who manages evictions. I have a a person who manages all of my notices. So I have a team of people. So when you say self-managing, I think people thought I'm actually getting calls and I'm actually communicating with tenants. The tenants have no idea who I am. Someone else Someone else said that why are you on the internet talking about this? Your tenants are going to be upset. They don't know me. Like I was smart enough to put a layer in between myself as the owner and who the tenants communicate with. So when I decided to fire my property manager after that crazy experience, I actually created a property management company. So my tenants are dealing with the property management company. They have no idea that I even exist. So in their eyes, you know, they have one point of contact and that person is the property management company. They know that the property management company has like this back office of support and that's where that's where that's where I come in. I'm back office support. So I know about things and I see things happening, but nobody is reaching out to me directly.

[00:09:29]And quite honestly, what I'm implementing now is you can't reach out to anybody directly. I mean, if you think about all these big apartment doctors' offices. I mean, whatever service that you're using, you can't get anybody on the phone. So, I we've also gone through a series of training our tenants that, "No, you have to interact with our system or you have to interact with the phone system or you have to interact with this AI chatbot and and we'll get back with you." You know what I mean? If a if a human needs to contact you, they will. So, I think that that's something else to help with the stress and the strain of the operations is just building in more and more buffer so that by the time things trickle down to me, it's it's usually resolved or, you know, one of the other systems have has caught it and resolved it. Critique number two, my contractors and vendors sound terrible. I don't know if I disagree with that and I have a whole video on why maintenance men and contractors never seem to last. So, I'm not going to go too in-depth here, but I will say it's easier said than done to try to find really good help in that regard.

[00:10:35]But, I do think people underestimate that this is one of the hardest part of the business because there's this people element and you can't control other people and you can't dictate what they're going to do and you can't, you know, people can be unpredictable at times. And so, it just introduces a layer of complexity that I don't think anybody's business is going to get around, even if you got one property or 3,000 properties. The people aspect of it is and always will be the hardest part. Another one in that regard was you need different tenants and a different strategy. I have changed my strategy multiple times with tenants. So, I went through a phase where I said, "I'm going to fix up all of my properties and I'm only going to rent to A+ tenants." Well, what I realized is that depending on where the property is, sometimes the the level of tenant you're going to attract is the level of tenant you're going to attract And you can't always upgrade the property hoping that it will upgrade the tenant. So, I saw I saw that firsthand.

[00:11:39]It It doesn't necessarily work that way.

[00:11:40]So, now instead of trying to force select a certain type of tenant, I'm more aware of what type of tenants is this area attracting. And then I keep my my unit turnarounds and my apartment upgrades, I keep all of that in alignment with that person. Cuz I've definitely spent a lot of money upgrading units that I'm just not going to get the ROI from because you you just may not ever be able to get the the rent that you were anticipating. But in terms of screening my tenants, that system is down. And I did go through a phase where I was using a realtor because my person on the ground, my maintenance manager, who's basically the head of my property management firm, it was too much asking her to try to fill units. It just it was slow. She just had too many other responsibilities. So, then I said, "Well, why don't we bring on a one of the realtors that we know and just completely outsource that?" Well, I still ended up evicting people and like things not working out. And then finally I'm just like, "I can't outsource finding my tenants." Like that's the one thing that I still do. I don't let anybody do that. I look I cross every T and dot every I. And that way if something goes wrong, I really only have myself to blame. But my process right now is keeping scammers at bay. People are staying longer. We I think we it took us several years to really figure out a tenant vetting process so that we could see better results. But one thing that people don't realize is that if you buy a a lot of the properties I bought, I already had tenants in it. So, some of these headaches I just inherited. And then, you know, it's not always feasible to kick everybody out. You buy a property, you bought it because it was already cash-flowing. So, to then kick everybody out and then bear the expense of whatever you have to do to get the apartment ready for your next tenants, it's just not always the reality. So, you're both right and wrong. Some tenants are still problematic. And I've gone through phases where I'm like, "Kick everybody out." And then you have a cash-flow issue. And so, it's really just a give and take up and down. The other major category of comments was that the math ain't mathing. And so, I think when I talk about profit, I have already paid all the expenses. I have already put away money for future expenses. I have paid all debts. And so, I think everybody a lot of people res- presume that there was no savings happening. And no, there is savings happening. But, it if you save $2,000 a month, that's that's 2,000 that you didn't take home. And so, there was a time where I wasn't that saving wasn't as critical in the business. But now, as the properties are aging, I just keep ramping up that's our savings. So, now we're up to 20%. We're saving 20% a month. So, imagine you're running a business 5 years ago and you're saving 5% a month. And now, your take home looks completely different because you've had to adjust some things so that the business can continue to sustain itself. And so, I think, you know, just because your profitability in a business is not where you would like it to be personally, it doesn't mean that the business fundamentally is not working. And so, what I'm focused on now is consistency.

[00:15:06]How can we get the business to a place where the monthly revenue is predictable. If you run a rental real estate business and you have figured that out, please leave me a comment down below. But it's it's really hard the bigger the portfolio gets. It's just up and down. And I I have friends in real real estate. And a lot of people I talk to are in the same scenario. You just never know what your profitability is going to be. And so when you think about quitting your job and not having any other sources of revenue, or not knowing what you're going to pull in every month, it really you know, it makes it difficult to plan for your personal life. Other people were saying that I should just sell everything and buy ETFs. Again, not wrong. I've considered it multiple times. And I think what you guys will see throughout the rest of this year, you will see me scale down. You will see me go through different phases of selling properties. What do I do with the proceeds? You know, am I fixing up older properties? Am I just exiting? I have realized that I'm at a point where I don't want to have to run this size of portfolio forever.

[00:16:17]And so that does mean that I have to move money around and do some other things with it. And that's the other thing. It's like if I had to do it again, I would because what people who are not in the real estate market don't understand is the power of appreciation.

[00:16:31]So you buy a property for 100,000 and let's just say 8 years later it's worth 250,000. Well, you would not have been able to come up with that 150,000 within the last 8 years. And so now even if you just take that 150 and maybe you put it in the stock market or maybe you do whatever it is you maybe you buy a franchise. Whatever it is you you're trying to do with it, real estate does allow you to skip steps. So if I was to sell every single property, I probably could have quit my job. I could probably put it all in ETFs and never look back.

[00:17:05]So I'm definitely looking at what are my underperformers, what are my major headaches, and trying to figure out what the next step is because the other consideration with real estate is you need to have a plan before you pull the trigger because that that tax implication is going to happen immediately, right? Now your tax statement looks like you made another $200,000 this year and you don't want to pay it all back. So you it really takes careful consideration.

[00:17:37]It's not as easy as just go have a fire sale and just, you know, exit. But I'm definitely going to be looking to diversify intentionally. I will say that I now know that scaling something and optimizing something are two totally different things. When I first thought about scaling the business, I 100% thought I was going to quit my job. But that was before I knew that real estate was about to become a job. And and then I realized it's like if real estate is still a job, is this the job that I want? And I think that's where I'm at now. Now I'm realizing that it's not that easy, but in it's not passive, it's not as hands-off. And so if I have to work in some regard, I'm now looking at how do I want to work? How do I want to spend my time? What do I really want to be doing? But I think a lot of high achievers make the same mistake that I did, right? You're trying to get from under the thumb of corporate so bad and so urgently that you're like, I have to scale something on my own quick, fast, and in a hurry. And real estate has taught me 100% that everything comes with headache, everything has bumps in the road, everything is going to be a job.

[00:18:52]And but in all of that, you have to consider your capacity, your you know, the level of stress you're willing to accept, the level of complexity you even want to be involved in because I think about like if I sell all the properties, I'm starting I'm at a starting point of investing in the market that I may have never got into without buying property.

[00:19:15]It's one thing to put $1,000 a month into an account and watch it grow. It's another to start with seven figures to begin with. Now you are making a salary.

[00:19:25]Now you are actually making passive income. So a lot of you really hit the nail on the head of where I am now. I am personally moving away from how big can this get?

[00:19:35]It's not about how many properties do you have? It's about how sustainable can you make it? How does it and how does it support your lifestyle? This is probably one of those conversations that I will continue inside the Cash Crew membership cuz there are some things that I don't want to unpack publicly while I'm still trying to figure it out there. My name is Jerry and if you're still here, do me a favor, go ahead and give that like button a smash, keep building that confidence and keep building that cash.

[00:19:59]You can get a behind-the-scenes look at my businesses over on Substack at Confidence is Cash and you can see how I'm using AI to run my real estate business over on the Prop Logic podcast here on YouTube. Thanks so much for watching this week, guys.