Why We Regret Buying (So Many) Rental Properties
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Some people regret tattoos, relationships, and haircuts, but we actually regret buying too many rental properties. Now, there are so many factors that can lead to acquiring more units and doing more deals, but sometimes more focus is put on the buy than instead of the hold. Today, we're going to share what we would have done differently so you don't make the same mistakes.

I'm Ashley Kerr. And I'm Tony J. Robinson, and welcome to the Real Estate Rookie Podcast. So Tony, before we get started here, do you have a tattoo and do you regret it? I have a tattoo in a place that I'm not comfortable talking about. I don't have any tattoos yet, but when I do, hopefully it's not one that I regret. Like my real estate portfolio, it was going too fast. I don't have any either, so that must be why we regret scaling our rental portfolios because we have no tattoos to regret.

Tony, starting out with your investing journey, what was kind of your progression of scaling? Did it start out slow? Did you just accumulate properties really, really fast in the beginning? Kind of start there. Yeah, we started off at what I feel was like a decent pace and then just kind of like exponential growth. But we started buying...

long-term rentals in 2019. So I got my first long-term rental October, 2019. And then about a month later, closed on my second long-term rental. And then, I don't know, maybe a

Four or five months later closed on two more that were kind of like burr properties, relatively inexpensive deals that we were planning to rehab. So in that first year, which I guess is pretty good speed, we closed on four long-term rentals.

Then we made the transition to short-term and that's when things kind of started to snowball. So we bought our first short-term rental in the summer of 2020. So kind of like smack dab in the middle of COVID bought the second one, I want to say 60 days later and then bought our third one in December of that year. And then after that 2021 is when things kind of went haywire. We had three short-term rentals when we finished 2020. And by the end of 2021, we had 15, uh,

So that was really the scale that kind of broke the camel's back, if you will. So what about you, Ashley? What did the scaling process kind of look like for you? Yeah, I started out pretty similar as to two properties right away. I think they were within three, four months of each other. And from 2013 to 2017, maybe one to two properties a year during that time period. But then in 2017, I

I found bigger pockets. I found the forums and I was in there all night long learning from other investors, learning about creative finance, how to find deals besides just the MLS.

and like finding like-minded people. I didn't know anybody else that was investing in real estate besides the guy that I worked for. So I was just really motivated, inspired. And after 2017, I just really started to accumulate properties. I also got my first portfolio deal, which had, I think, 10 units included into it, maybe 12 it was. And, um,

So like 12 at once, that was a big deal because I had only bought duplexes prior to that. And so 2017 is really where I started to speed things up. What about you, Tony? What was that point where you... I found bigger pockets and that's what really propelled me. What about you? What was the thing that...

made you move faster and scale faster. Yeah, for me, it was losing my W2 job. So Christmas Eve 2020, I get a call from HR saying that I no longer have employment. And for me, it's like, okay, well, what do I do? Do I go back and try and find another gig somewhere else?

Or do I kind of take this time to double down on scaling up the portfolio? So my wife and I, Sarah, we said like, hey, let's just get ourselves 12 months and let's see how far we can go. And yeah, that 12 months ended up being 2021 where we, you know, what was that five X star portfolio on the short term side from three to 15. Okay. So I think some of the reasons that

I was able to scale so quickly during that time was that I really felt more confident in purchasing deals. I had done several now. I knew how to actually acquire a property. I had the resources. I was starting to understand how to finance the deals. I was getting lines of credit.

We both had partnerships that we were using to, you know, exponentially add to our portfolio. Is there anything else that you would kind of add there as to what attributed to that rapid growth? I think, you know, part of it was hard work, but I also think part of it was luck. You know, like I got lucky that interest rates were near zero, you know, and that the ability to borrow money was a lot easier than it would have been in the past.

I was fortunate that I had a network of people who wanted to partner with us to help us continue to acquire these properties. I was lucky that I had stumbled into these markets before they kind of blew up where we were able to get in at good prices. So a lot of it was hard work, obviously, but I think it was also an element of just like lucky timing with the strategy that we chose and just kind of where the market was at at that time that made it a lot easier to scale at that point.

Let me just ask you, like, I mean, when you look at the scale of your portfolio, like, I guess, how much can you can you attribute that scale to, you know, just like granted out hard work versus maybe a little bit of luck on your end as well? Well, first of all, I would say that I got lucky with an addiction to acquiring properties. But

But yeah, so like even in 2017, 2018, like it was really easy to buy under market value properties. So when I was purchasing properties, I was buying in these small rural areas. There wasn't a ton of other investors. So I really didn't have a ton of competition, the towns that I was investing in. And also like I, there was one property I bought it for, I think,

$32,000 maybe. Maybe it was 37, something around there, whatever. Right after I closed on it, I put a fridge in it and it appraised for like 42,000 or something like that. Appraised for way over what I purchased it for.

I was able to refinance it, pull all my money back out. And I think we ended up getting like a check for $4,000 too at closing of the refinance because we were able to refinance it for more than we owed on that short-term loan we'd gotten on the property. So yeah,

I think there was definitely some luck in the timing for that too. As far as being able to find deals, it was definitely a lot easier to find deals then than it is now too. But I do still think that you can get in trouble, which we're going to talk about

about more as to scaling too fast and why we actually regret that in some sense. And I want to get into the scaling and the challenges and the regret that comes with that. But I just also want to talk because like, you know, a lot of the people that are listening, you guys are rookies who maybe are working on your first deal and maybe have one or two. So

you hear the scale of me and Ashley and you're like, oh my gosh, like, you know, how could you guys accomplish that? And obviously a lot of it is that Ash and I just worked really hard, but there was also some market factors at play that I think allowed us to do that. And the reason why I asked that question, Ashley, I'm, I'm, I'm reading this book. It's called the psychology of money. Have you read that book before? No, but I've heard about it. I heard about it before too. And I just like never took the time, but I finally got the audio book. I've been listening to it and it told the story of Bill Gates and,

And, you know, everyone knows Bill Gates found at Microsoft, one of the richest guys on the planet, but it talked about how lucky Bill Gates was as a teenager. So, you know, in the teenager and whatever year it was like in the, I don't know, in the seventies or something like that, early eighties, he was one of the only teenagers on the planet that had access to an actual computer. Like there were whatever, 40 million teenagers in the United States, you know, uh,

In his little high school, of all the high schools on the country, they were the only high school that had a computer that students had access to.

Like literally a one in a million chance. And Bill said, like, if my school didn't have the foresight to get this computer and give us access to it, like there would be no Microsoft. So obviously a lot of hard work, a lot of, you know, he's an incredibly brilliant guy, but sometimes that combination of both at least to the scale. So I just, I just want to highlight that because I don't want Ricky's to hear, you know, you guys killed it and, you know, you know, I'll never be able to do that. You guys got to find your own combination of skill and luck as well.

So we're going to take a quick break. And while we do that, make sure to check out the information about the BiggerPockets conference. It will be in fabulous Las Vegas this year. So if you want to find out more information, how you can hang out with Tony and I, you can go to biggerpockets.com slash conference. And just a little hint that if you hurry and get your ticket now, you get a discount so you can save that extra money for your next deal.

So stay tuned to hear from our mistakes and what you can do different when acquiring properties. This show is sponsored by Airbnb. We love hitting the road for conferences, for events and live appearances. But while we're out there making connections, we still want to make the most of our investments back home. Why let your place sit empty when it could be earning you extra cash?

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All right, guys, welcome back from our short break. So Ashley, you know, you scaled quickly. I guess when was that breaking point for you? Like when did you realize that you had actually scaled your portfolio too fast? Yeah. So what I regret is putting too much attention and focus on the acquisition. I worried about how to find the deal. I worried about how to finance the deal. I worried about how to close on the deal.

Then after that, I had this horrible mindset of just set it and forget it. Like I got the deal. Yay. The hard part is done. I have the property now. I can collect my cashflow and go on my happy way to buy another property.

And so I just kind of got into that groove where I was spending no time on the actual operations of the property. So there was also the asset management piece. I didn't put any effort into that as to like quoting out my insurance every year to like make sure I was getting the best rate to actually watching what the expenses were for the property. At that time, if there was a water bill that was like...

super, super high because the toilet was leaking or something, I probably wouldn't have known. I probably would have just paid the bill, paid the bill, paid the bill because I was so rushed and focused and overwhelmed. I probably could have made more money if I would have put more focus on

on the finances of everything, of the operationals, getting them rented faster because I had the time and I had the system to actually get tenants in and out of there. But if I was busy or I was going to look at another property or I had to take care of this or do this, then a property would sit a couple more days until I could actually get out there to make sure it was clean, ready to show. So

That became my breaking point as when I got so overwhelmed that

that I felt like I was not liquid. I felt like I had a lot of equity in the properties, but I was so strapped for actual cash because I was mismanaging the operations of this. And my cashflow was not what it was supposed to be because of almost my laziness on the side of operations. And so it got to the breaking point where I actually ended up selling a duplex. So we sold that property.

We took that capital as our breathing room and we went ahead and built out, you know, how it should have been, the systems and processes and didn't acquire any properties for a while and just use that time to kind of gain focus. But that was already at,

20 something properties I was at. So that was a long time before that moment came for me. Yeah. And Ashley, you touch on so many things that I think echo our journey as well. We were just so focused on the next property and how do we get this next one? And I think part of it was the

you know, was this kind of like ticking time bomb that I had in the back of my mind of like, hey, we gave ourselves 12 months. We got to make sure that we make the most out of that time. But I think there is something to be said about scaling at the right pace and making sure that you've got the bandwidth because you said the word overwhelm.

And I think that's almost exactly how Sarah and I, my wife were feeling as we were scaling our portfolio as well. And I think like the, the breaking moment for us when we realized that we needed to like slow down a little bit as well was Sarah's sister was getting married and it was a, it was a joint like bachelor, bachelorette weekend. And we were there and Sarah and I both were just a little distracted throughout that weekend because we were responding to this guest, checking in with this cleaner, doing this thing. And we just couldn't be present and,

And we're like, well, this isn't what we signed up for. This isn't the reason that we wanted to be investing in real estate was to have this full-time job where we are now just employees to our portfolio. And that was kind of the moment for us to say, okay, we need to slow down, put some better systems and people in place to help us really take this portfolio to the next level. Yeah. And I think to kind of point out, we were both self-managing at that point. And that definitely played a big role.

big piece in it, especially for me, where maybe if I would have had property management from the start, it wouldn't have been as overwhelming. But, um...

I don't regret self-managing. I regret not building out an actual system and process for how to manage the property and how it's going to work. And we both ended up using virtual assistants and building out team members, but there's so much automation and so many templates and checklists and so many things you can do as a rookie investor who doesn't want to hire anyone yet. It's not to that point that you can do to make your life

so much easier. And that's kind of like our big regret is that we waited until accumulating 20 properties because now you have all these properties, you have to pause. You have to stop your main operation, which is acquisition mode,

And you have to basically go back and implement these systems into these 20 different properties. And it is so time consuming. You have so much information in your brain that you know what to do, but it's not written down for anyone else to help you with it.

Okay. Something as simple as opening the mail, even like nobody could have done that for me. Nobody would know what this LLC before with this property was for. Nobody would have known how to handle that except for me. And that was a, a huge breaking point. Like you said, Ashley, I think we, we followed a lot of the same steps. I,

I hired a personal assistant, which has been a game changer. And then we hired several virtual assistants to help in the Airbnb side of thing. And like the combination of those team members has made the biggest difference. But I guess what was like the first step for you? So you sold the duplex, I gave you some breathing room. Like when you sat down and just kind of looked at, okay, here's everything that's in front of me. What did you actually focus on first? Yeah. So the first thing was like learning what's an SOP.

standard operating procedure. So I started as little as possible. I had heard this other investor talk on Instagram about how just take paying a water bill. So just as you're paying the water bill, write out the steps that it takes to do that. And then creating this master list of all of the different things that you're doing in your business.

This was awful for me to start because I was just rush, rush, rush, rush, rush. I was so overwhelmed to actually take the time to document what I was doing. And, you know, there's a lot of resources I've learned about like loom where you screen record and you can talk while you're doing something. You know, there's,

Tango, where you can create SOPs based off of screen grabs, things like that. So definitely a lot of chat GPT can help you now build out SOPs, but

That was my starting point as to like, okay, I need to actually write out some things that I'm doing so that I can get some help or so I'm not using so much brain power to basically recreate something. Yeah, 100%. And like you talk about SOPs and I think that was one of the best things that we did. And it was the first place that we started as well because it's,

as you're scaling up your portfolio, a lot of it is tribal knowledge, right? Where it's in your head. But a lot of these things you need to get down on paper so that even for yourself, like even if you don't have anyone on your team yet, say you don't go out and hire a virtual assistant,

Sometimes just having these things documented for yourself can be beneficial because maybe something doesn't pop up on a daily basis. Maybe it's something that you have to do monthly or quarterly. And every time you sit down and do it, you're like, okay, how do I actually do this again? Or what was my process for doing this? And when you document something, it provides clarity for you and for anyone else that may need to do it. So much like you, Ashley, we lean into the SOPPs. And our SOPs have evolved a little bit since we first started. But like when we first, first started, it was like,

It was just like a big 70 page Google doc with a bunch of different headings. And that's kind of how we started to build our SOPs. And now, like you said, we use a combination of Loom and Checklist to kind of break it up a little bit. But that was really the first step that we focused on as well. And it gave us a lot of confidence in what we were doing. And it gave us clarity in what we were doing.

Um, so I guess let me, let me ask Ashley, did you, cause I know what our process was, but did you build out your SOPs before you started hiring in virtual assistants or did you do it the other way where you hired the virtual assistants and then built out your SOPs? So I started with, because I,

I had this mental block that like I had to have something to have somebody else do. So the first assistant that I actually hired started to do payables and receivables. So it was like, okay, it's just a very small part-time task of doing that. And then it went on to adding on to tenant communication. Then I got to doing the mail. So I would start with

creating at least some tasks ahead of time as to like, this is how you do this to get somebody started. But then as time develops and you realize there's more things they could take on, they'll actually, if you hire the right people, they'll actually take initiative to start doing things. So Tony, you gave me this advice, you know, years ago where when you hired someone, you would have them recreate the SOP.

So instead of you doing all of it, you would have them go in and maybe change it or update it as to how they would see fit doing it since they were the ones that were actually doing it. And I always thought that was such great advice.

And, you know, it saves you a lot of work from having to constantly update it too. And like the other cool hack on top of this is that as you, like, say you build something out for the first time, Ash and I both talked about loom. We got to get them to sponsor the podcast. We've been talking about them for a long time, but, uh,

Loom is like a screen recording tool where it records your screen, records your voice. You can actually take the transcript of your Loom, drop it into an AI tool like ChatGPT. I was literally doing this right now as we were talking. I pulled one of my checklist videos, dropped it in the ChatGPT and said, hey, create a direction and checklist off of this transcript. And it broke it out for me and gave me a really cool checklist at the bottom.

So such an easy way to start documenting your processes where you literally just open up your computer, do the thing, and then give it to an AI tool like ChatGPT to build out that system for you. And it becomes even easier to keep those things updated. And especially managing properties, being a landlord, you want to be consistent.

too, with what you're saying and what you're doing. Because you can actually get into trouble with fair housing laws. So if you have everything already implemented, then it's a lot easier to stay on task and to stay on point and to be consistent too. I think the main takeaway that you should get from what Ashley and I are sharing here is that it is so much easier to build out your systems and your processes when you have one property.

than it is to do it when you have 15 or 20. And I, you know, I made the mistake in my business of, you know, we onboarded three virtual assistants all at the same time with 15 Airbnbs. And it was a complete, you know, what type of show, you know, like nothing, nothing was documented. There was no systems for them to jump into. And we're like building the plane as we're flying it. But had we maybe hired one VA with one property, even if it was part time,

Now we can really take the time to build out those systems and processes. So we're not even necessarily saying that you need to scale slower, but your rate of optimization, your pace of optimization has to match your pace of acquisition.

So if I wanted to scale by 5X in one year, well, then I also need to scale my operations and my processes by 5X that year as well. And we didn't do that. We're going to take our last ad break. But when we come back, we're going to actually talk about the financial impact this had on us and why we regret it. ♪

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This definitely cost us money and it, you know, could be money we actually paid money we lost out on. So what's one example of ways that this was detrimental to your business by not building out these systems ahead of time? Yeah, I think even, even just beyond like not building out the systems, but just like scaling for the sake of scaling, I think is where we kind of bit ourselves in the butt and we knew that

Like Joshua Tree is where we have quite a few of our properties. And we kept telling ourselves, okay, we should probably diversify somewhere else because we're putting too many of our eggs into one basket. But we had already built out a really good pipeline of deals in that market. We had already built out the team. It was just easy for us to kind of keep pounding the pavement in that same market. And at the time, the underlying economics of that city were strong. Like everything still looked really great in that market. So we're like, ah,

It's going well, everything looks good, no sweat. Now at the time I hadn't taught myself how to look at some of the underlying data where maybe there would have been some problems that would have bubbled up. But because we kept like moving fast in that market, we bought a property, gosh, when we buy that property, it was like the tail end of 2022, I believe.

And we wanted to flip it like we were flipping homes out in that market as well. And during the time between when we purchased that property and when the rehab was finished, the market, like the resale market, has shifted completely. And we had two options. Either we were going to sell that property at a loss or

to be able to pay off our private money lenders, or we would have to refinance, like do a bird and still come out of pocket, almost the exact same amount. So either way, we're writing a check, you know, to, to exit this deal. And, you know, gosh, I want to say, Ashley was probably $200,000 that we had to put into that property, uh,

because of this failed flip that we had. Talk about a lesson learned. And we've been telling ourselves like, hey, should we keep scaling in this one market? But again, just the desire to keep growing led us to that decision. So that's probably the most apparent challenge that we had with this focus on scaling just for the sake of scaling. Yeah, I think one of the biggest things was the opportunity cost.

of what I missed out on because I was so overwhelmed and I couldn't take on more and I had to stop and pause. Like there was a full year that I didn't purchase anything because I was so focused on building out these systems and processes. Guess what year that was? 2021, the year of the best ever interest rates. Okay. I did not buy a single property. Okay. Yeah.

So I had started to, that was like the year it really hit me. Before that, I was still buying a couple of properties slowly as I was trying to build out things. But then I decided like after COVID, I had acquired a liquor store. We had gotten a four unit. We had done our, a rental, huge full gut rehab that we ended up flipping like all these different things. And so 2021 was the year I did not acquire anything. And that was probably the best year

interest rate I ever could have gotten. So I'm probably one of the very few investors. I didn't even refinance anything because I was so deep into fixing my bookkeeping and everything like that, that to actually go to the bank and get a loan, I'd have to give them all my tax returns, give them my bookkeeping, my profit and loss statements. And I was working so hard at correcting all that. I didn't even take the time to finance anything, refinance anything to get those lower rates. So I'm one of those

investors that I may have got lucky when I was purchasing, but I did not take advantage of those low interest rates. And I do not have a, my lowest loan, I think is like 4%. I don't have anything under that because I missed that huge opportunity to get those low rate loans because I was fixing my business because I'd spent so much time acquiring. I had this goal of

30 by 30. I mean, 20 by 20, because I'm only 29, but...

But that was like so important to me because I just thought the more units I had, the more cash flow I would have. And you can have way less properties. And if you are operating efficiently, you can make more money than somebody. And I think one thing that's taken me a long time to learn is the long-term play of being a buy and hold investor. Yeah.

As to properties I bought 10 years ago are cash flowing so much more because of the increase in rents. My mortgage payment, 30-year fixed rate mortgage payment has stayed the same. And I'm seeing a lot of cash flow. And I also have a ton of equity. A property that I put, you know, I think it was like $25,000 down to buy. And that was like, you know, 20% down, I think.

And then, you know, I've had that property since 2017. I have over $100,000 in equity in that property right now. And it's cash flowing like $900 per month. And it definitely wasn't that when I purchased the property. It was not that much equity and it was also not that much cash flow. But rents have increased so much in that area. So like if I would have not bought as much property,

I could have maybe paid off more debt on the properties. So not to be over leveraged for that period of time where I needed to sell something. And now it's definitely become way more important to have things paid off and have them free and clear or have lots of equity.

or that like security. So I definitely have pivoted and changed as to what's important to me. And like that realization of more units, more cashflow doesn't always equal that. Yeah. I think, you know, you bring up an amazing point, Ash. And I think just, you know, the, the age of social media, we sensationalize unit count, door count, how many properties do you have? But to your point in an ideal situation, the question that we should be asking is how can I generate the most amount of revenue with the least amount of work?

And sometimes that is getting more units and it's scaling faster, but oftentimes it's less units and just being more efficient with the units that you have and getting more profitability out of the units that you have. So for all of our rookies that are listening,

take heed on the story that Ashton Ladd just shared of don't scale just for the sake of scaling. Don't pick an arbitrary unit number and say, let me get to this unit number. Focus on your net worth. Focus on your cash flow. And then, like Ashley said, understand that real estate is a longer game to be played. And

10 years from now is when you'll really know if that deal was a killer deal or not. 20 years from now, you'll know if that deal was really a killer deal or not. In those first couple of years, maybe the cash flow isn't all that great. But if you're playing for the long game, that's how you can really make sure you're making the right decisions for your portfolio. Okay. Well, Tony, this has been our regrets episode. And if you're a fan of the movie, We're the Millers, you can just picture your tattoo, no regrets.

That actually is a music that I've seen. We talked about Tommy Boy. I hadn't seen that. Finally. We just rewatched that movie like last month, like during Christmas time. We're just like looking for good, funny movies to watch. So for our rookie audience, if you haven't seen We're the Millers, starring Jason Sudeikis and Jennifer Aniston, it's a great, great movie. You even know the actors that are in it. Wow, Tony. Yeah.

Well, thank you guys so much for joining us for this episode of Real Estate Rookie. I'm Ashley and he's Tony. Make sure to check us out on our Instagram page at BiggerPocketsRookie and also to subscribe to our YouTube channel at Real Estate Rookie. Thanks so much for joining us. We'll see you guys on the next episode.