Every real estate entrepreneur reaches a point where the business they built can no longer run through sheer effort alone. In this conversation, I talk with Niyi Adewole, who went from a single house hack in Louisville to a 30-unit rental portfolio, a ground-up self storage development, and a 10-agent investor-focused real estate team spanning three states. Niyi walks through the tasks he held onto for far too long, from invoicing to transaction coordination to guest messaging, and exactly what pushed him to finally hand them off. We also dig into how he evaluates new opportunities, how he manages a business across multiple states without ever setting foot on some of the properties, and why he believes consistency beats big bets every time. If you have ever felt like your growth is capped by your own hours in the day, this one will give you a lot to think about.
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Hello listeners and welcome back. I’m Adrienne Green and today we’re here with Niyi Adewole. Here we focus on how real estate entrepreneurs break free of the grind and create the freedom they wanted at the start, and Niyi is a great example of that. Thanks for being here with me.
Thank you for having me. I’m pumped to be on.
To start off, give us the quick version of your portfolio and business and what they look like today.
My name is Niyi Adewole. I have been investing in real estate for over a decade and built that portfolio well before I got a license. I got licensed in 2021 and have now built out a team. What it looks like today is I have a self-storage unit that’s 225 units that we built from the ground up a few years ago. I used to have 30 long-term rentals, but I traded those in to build that self-storage and buy some other properties. I own eight short-term rentals, five long-term rentals, and I land on flips and then help other investors get started in real estate as well.
I love a lot of your story and we’ll dive into the pieces, but some of the great things I’m hearing is that you’ve adapted and pivoted. You didn’t just stick with what you started with as you learned and grew and different opportunities came, and you weren’t afraid to sell what you started off with to transition into this higher level of real estate investing that you’re doing now.
Absolutely. And it was not all me. This is definitely with partners and help from the outside because I wasn’t the one that came up with that self storage idea. I consistently took action every single year, building that portfolio. And when an opportunity arrived, I looked at it, ran the numbers, said, this makes sense, and I took action.
Love that. So let’s go back a little bit more to the beginning where you went from a three unit house hack straight into a 12 unit as your second deal. That’s a pretty big jump. What made you comfortable scaling that fast? What wisdom can we have for listeners who may be in that same place? And what would you tell somebody who’s maybe a little fearful of a jump like that?
I would say the main thing is taking that first step. Having the courage to go after a 12 unit, it’s not something I would have done for my first deal. Not at all. I had to do the first deal and then sit on the sidelines for about 18 months saving money and looking around for another deal before this opportunity came up. And the reason I felt comfortable taking that one down is because I got that first house hack. Prior to even getting that first triplex house hack where I lived in one unit and rented the other two out, I’d been listening to and reading books, and listening to different podcasts to gather information and understand what I was doing in this space. When I took action on that first one, it gave me the power to take action on the second one. And the second one was literally three houses down from the first one. That 12-unit opportunity was on the adjoining street. I felt very comfortable having walked that neighborhood many, many times, and comfortable in the numbers I could pull in because it had similar unit sizes to that triplex to go after it.
I love how some people might have been too scared to make that jump to that twelve unit but you realize, this is in my neighborhood, this is an area I know, I know these numbers really well, so I’m not going to get scared away arbitrarily just because it’s a lot more doors.
Absolutely. The main thing with it is that the zeros just get bigger. There’s nothing that really changes with the numbers outside of the lending piece. When you go after twelve units versus four or less, you’re looking at more of a commercial loan, which is slightly different. But from checks and balances, renting out units, getting the most that you can from different tenants, renovating units, all that is about the same. Now you’re just bringing it to a higher scale and it depends on what level you’re at, your life, to be able to take that one on.
Now, a lot of your story is about evolution. Let’s talk about asset class. You’ve done small multifamily, ground up self-storage, a lot in the short term rental and midterm rental space. How do you decide which asset class deserves your attention, or how did that evolution happen?
My bread and butter is residential, small, multifamily for long-term rentals. That’s what I did the first five years of my investing career. I went from that triplex and was able to build it up to 30 units. That was all I was going to do. This works, no need to do anything else. But I started meeting other investors along the way and they encouraged me, before the pandemic boom, to try out short term rentals. When I got promoted through my W2 at the time, which was medical device sales, and moved to the southeast, I bought a house hack and turned that house hack unit into a short term rental just to try it out. At that time, if I could make fifteen hundred dollars a month, I was going to be golden. I said, let me try this thing out. I know I can get that long term, let me see what we can do short term, just put some furniture down there. I was able to pull in about twenty five hundred a month. That’s when my eyes were opened to the short term rental market.
I went all in on that. Circling back to how I got into the commercial space and building that self-storage from the ground up, that was all by working with an investor-friendly realtor to build up that unit of 30 units. I was buying those in Louisville, Kentucky, all within a mile of each other of where I used to live. I started working with an investor-friendly realtor who owned even more real estate than I did. She was the one who, after working together for six or seven years, said, of all my clients, you’re the one with the most similar mindset and the growth mindset, and I’d love to work with you. I was comfortable working with her because a partnership is almost like a marriage. You really have to know that other person. She brought this opportunity to buy this land, build self-storage, and do a townhome project on that piece. It took about six months of negotiating with the owner, but we were able to close on it and kick that project off. What I did was sell these units to put my portion of the money into that storage as well as to buy some more properties in Atlanta where I reside.
I think there’s a lot of great wisdom and takeaways from that one story. I was an investor-friendly agent actively working for a number of years. I know you are that now. Sometimes investors don’t necessarily value a relationship with an agent. They’re going to go with whoever brings them the deal, they’re kind of agent agnostic. I can see why they’re doing that and yet they’re missing out on opportunities like what you got in Louisville.
I think you’re spot on. I used to be that guy. I still remember that because I’m still an investor. One of the things I used to hate doing was signing a buyer brokerage agreement before we’ve actually done anything. One of the practices we do is you have to sign one before you can show a property now. But the way we work through that piece, especially because we focus on working with investors, is we identify rock star properties and we’ll put offers out there before we even go and see it, just to see if we can get this under contract. And in that we have a buyer brokerage agreement, and then we’ll go check out the property when we have it in due diligence. A lot of investors, at least before they meet our team and have conversations with me and others, tend to not value that real estate professional as much. I would say you’re missing out. Not just on writing offers and contracts, anybody can do that. But when you see that we’ve been through over 180 deals, probably way more than most of the investors we’re working with, and we’ve been able to negotiate a crazy amount of credits, a crazy amount of deals. There was one in particular where we were trying to help a client buy their second short term rental with us up in the mountains. It’s two A frames sitting on ten acres of land. It was listed for one point two million. At that price they didn’t have the funds to come forward and do that and they’d have to finagle and pull from all different places, and they didn’t want to do that. We were able to work out a deal where we’re essentially going to get two hundred thousand in seller credits, to help them furnish the whole place, get it up and running, and only have to come with the down payment. We were able to rework that because we think like an investor and we’ve helped other investors do this. Not to mention, when you look at having an investor friendly realtor, the value is in the list of vendors and the list of contacts, they can help you get to your goal. If you share the goal you’re trying to reach with them and you check in with them constantly and they’re checking in with you, there’s so much help I had along the way. If I need a roofer, if I need a plumber, I’m just going to get the exact person she’s already negotiated with, and they’re going to help me, and we do the same for our clients.
I love that you brought up a lot of good points of what that relationship can offer to investors. And the other thing I loved from that story is how you did the experiment with the short term rental house hack. That’s something I love, how can we just dip our toe in the water, how can we test this out and recognize that this isn’t like before we sell our whole portfolio and pivot to a new strategy. Let’s just see if it’s for us with a little taster. I love how you did that. I’m curious what other wisdom you would have for people along those lines.
I’m always a fan of trying the one that’s going to require the least amount of capital for you to at least test this thing out. If somebody’s willing to delay gratification and they want to get started in real estate, I’m always pushing people toward a house hack. Go get a duplex, triplex, quadplex like I did, live in one unit, rent the others out and have the tenants pay most of your living costs. Now you’re winning on every front. You have to live somewhere. Your living is subsidized and you’re seeing if you actually like this thing. If you don’t, you move out in a year, you don’t have to do it again, you have an investment property. If you do like it, maybe you find a passion and you grow from there. Whereas I have a lot of newer investors who say, for my first property, I’m going to go do a huge flip and a luxury flip. Yes, there are some people who are successful there, and we will help you if you’re adamant, but we always pause for a second and say, why do you want to do this for your first one? It’s going to require a certain amount of money. Even though you’re getting hard money, they’re still going to charge you points. You’ve got to put down twenty percent if it’s your first one. There’s a lot going on and it’s almost like riding a motorcycle without a helmet. Whereas doing a house hack where you’re going to put down five percent, three and a half percent, it’s really hard to mess that up. It’s like riding a bicycle with the tricycle pieces that help you as a kid. It’s a way to get started with a little bit less. We always push people toward doing something like that for their first investment, as opposed to going all in and putting down fifty percent on a property.
I think that’s something also when people work with an investor friendly agent, you get that wisdom, and one thing I know from when I had my team, that resonates, is a good agent isn’t just going to say, yeah, that sounds great, to the thing that’s going to give the biggest commission. If somebody’s wanting to do that luxury flip, that’s going to give the biggest commission, and a good investor-friendly agent’s going to say, let’s set you up for success, even if I’m going to make less on this first one, because my priority is you as the client, as the investor, doing well. If you like the investing, I’m going to make a whole lot more money in the long run because you’re going to keep doing it again and again.
Adrienne, what you just hit on is the key. We share this with our clients. That is literally our model. It’s not the first property, but we want to be there for you through the first 30 units that you build. The same way I did with the other agent who’s now my partner in the self-storage. With her, over a six or seven year period, I bought thirty units and I’ve now sold those thirty units. That’s millions of dollars in revenue for her business that she doesn’t have to keep coming back to the well for. I was coming back because she was excellent. She’s been awesome. She’s been awesome as a partner. My goal is to develop the same thing here. We’ve already had multiple clients who have come back for their second, third, fourth. Right now, under contract, I have a client buying his fourth short-term rental. He moved down from New York, he lives in Metro Atlanta and he’s doing this full time now because they’re killing it. I have another client buying their second property. They bought a four-plex maybe two months ago. Now they want to buy a short-term rental to save on taxes because we connected them to our investor-friendly CPA and they’re talking to them about saving on taxes. When you look at my team of 10 agents, half of that team came from people we helped as clients first, by their first, second, or maybe even third deal. Then they liked the process so much that they went and got licensed, joined the team to help others. We’re thinking more long term. That’s why we wanted to get into this niche of helping investors, because not many realtors can speak the way that you speak and I speak. We’re actually investors trying to help people. Most realtors are kind of out there just showing regular houses, which is fine, but we wanted to purposely target this niche because if we do this well, we’re going to have repeat business for a long time.
Now we’re going to talk a lot about systems, because I know on your investing and management, property management side, and also with this real estate team, there are a lot of systems. Let’s break down some of that for our listeners, both investors and agents, with some wisdom they can walk away with. The first shift I want to talk about that we see a lot in the investor space is you were managing your own units and now you are managing or co-hosting or helping other units in the short-term rental and midterm rental space. I’m sure there were some lessons learned, maybe some the hard way. How did that shift, starting to manage your short-term rentals and midterm rentals, teach you about your own operation and help you improve your systems?
You’re going to have to go through the fire. There’s going to be an in-between period where you can’t necessarily pay people a whole lot to join the team, but you’ve got to push through, and you’re going to be working an insane amount of hours during that time period to make it happen. Specifically talking about the short term rentals, I started out just managing that one in the basement, the house hack. It was doing so well that after three months, I bought a full-on house in the same neighborhood and we made that a short term rental. I was connecting with other investors in the city because I was newer here and started managing some of theirs. Very quickly I went from just managing one to like four or five by the end of that year. Then word of mouth started getting around and others started coming on board to help. Initially it was just me. It was me and software. I use a software called Hospitable, which allows you to automate a lot of the guest messaging, which is amazing. It also allows you to automate the cleaner messaging and give them a calendar so they can see where their next clean is. Initially I was just trying to do this through the app, and I missed one or two cleans that were last minute ones, where somebody extended or somebody checked out early and we needed to get the place cleaned. It was terrible. I’d recommend implementing software immediately, like Hospitable or others out there. Then there’s that happy medium point where you start to get to the point where, and my wife will attest, I was still messaging guests at like nine PM, 10 PM. When are you putting the phone down? We got into this so you could have more free time. That’s when I started looking around. There were a couple of people raising their hand and saying, can you teach me this, can you help with this. I brought two of those individuals on and I could not pay them much. It really was selling them on the vision of what this was going to look like a couple years down the road. I was able to do a percentage split of the revenue we brought in from a property management company and they were okay taking that and working together to handle the messaging. That was the first couple hires we made. Fast forward to today, we still have one of those two individuals with us. Now she’s moved into an operations manager role and she’s making a whole lot more, salary plus a couple bonuses. Now we have VAs, we’ve got AI, we’ve got a bunch of different cleaning teams, and all of that has gotten a lot easier. But that messy middle is a time period where you’re going to be working 16, 17 hour days to try to make it happen. Once you get past that and push to that larger level, you’ll have enough income coming in to actually hire people to do all the work. Now I don’t message at all. I don’t do much, I just meet once a week with the team to make sure we’re on track and give guidance on certain things. Then I work with new owners to get them onboarded and I go from there.
I love that. That leads perfectly into the next question. I also love Hospitable, but let’s talk about when you started to get those team members on for property management. When did you start to identify processes you could document and hand off? How did you do that? That’s something a lot of listeners struggle with, they’re like, I know how to do it all, it’s all in my head, how do I hand that off to someone else? How did that work for you?
It took a lot of setting aside time to make it happen. Nowadays it’s easier than ever. I’ll talk about how I did it and how we do it today. How I did it is I read a book called Traction, which I think you’ve probably read and a lot of people should read if you haven’t, as an entrepreneur. One of the things they talk about is elevating and delegating, which is, every single day you should, but every week at least, you should be thinking about, what’s taking up most of my time that’s a repetitive task that can be delegated to somebody else, so I can elevate to another level and bring more business in. I started one at a time taking, this is something I do, like coordinating maintenance. When things come through, how can I shift that over to my guest experience team? When it comes to even the messaging, always look at it in two ways. One, can I automate this? In Hospitable, a question we get all the time is about parking and about Wi-Fi. Can we have an automated message go out? Can we tell people ahead of time and then if they ask, have an automated message? Yes, let’s do that. If it’s something more obscure, what we did is put together a Google sheet. Anytime there was a weird question, I had the team reach out to me, I’d give them a response, and then they added that to the Google Sheet. Now there’s AI within the Hospitable system, and you can just put it directly in there, give it the answer, and it’ll start responding for you. What I’d say for people moving forward when it comes to putting together systems is utilize what we have. Now, when it comes to putting together a system, I don’t even write anything down. It used to be, I’d go into a Word document or Excel sheet. Now I record a voice note, talk through the whole system, copy that, paste it into Claude or OpenAI or whatever AI system you’re using and ask it to create an SOP that’s very simple to follow. That’s what I’ll put in. Taking it a step further, you can also just put that into the Hospitable AI, and it will understand and know the SOP and be able to respond for you and pull from that knowledge portal if a guest has a question. It’s gotten easier over time. I like using Loom too. Anytime I need to show my team, whether it’s the real estate team or the short-term rental team, how to do something, I do a Loom video, two minutes, three minutes, send it their way, and then we keep a repository of that in a Word document that gives you a description of what it’s talking about. If you ever need to find it, you can just search and click it.
I agree with you. I built my team before AI, and yes, we had to actually write SOPs. I made the video and my VA had to type up the SOP, and now you can get a pretty darn good one just by putting the transcript of a call into AI. It’s easier than ever. I love how you saw that. You also made the point that it’s going to take some of your time at first to get those things out of your head and get them transferred. People are reticent to acknowledge that, you almost have to slow down to speed up sometimes.
You are spot on. The best thing I can tell you is use your calendar to control your day. For the elevate and delegate, I still have it on my calendar. I set aside time every Monday and every Friday to think through what’s taking up most of my time, can I delegate this. If I need to put a system in place, it’s during that one hour time frame that I’m recording the Loom video, putting together the SOP with AI now. I make sure I’m checking it twice, checking it three times, because once I get this off my plate, I don’t have to do this again. I’m sure you do the same for things like this podcast. If you were the one who had to record the podcast, find the guests, and do all the edits and all this stuff, which you probably did starting in the beginning days, there would be a lot less guests and a lot less content you could put out. Over time you start to realize you don’t have to be the one doing all this. Even in the realtor business, I did the exact same thing. You can ask my wife, she can attest to this. There used to be times where I’d be working 16 hour days. Now I have a team and we’ve built it in a way where it’s almost like our apprenticeship model. I’m done work every single day by 5 PM. The only time I work a little bit past that is if the due diligence is ending that night and I have to make sure we get something done. I don’t even show most of the properties we’re doing. Some of my more junior agents are out there showing while I work on the biggest priority piece, which is negotiating a deal, making sure the numbers work, making sure it’s in the right area, and setting our clients up for success. All that came from the elevate and delegate and really thinking through how we can move this off my plate so we can serve more. If it depended on me to show every single person, there’s only so many hours in a day. But if I have a team showing all the people, I can help 10, 20 people at one time.
I love all that, it resonates. I’d say for our investor listeners, in my opinion, you get better service when you work with a team than with a solo agent because of what he’s sharing here. If you’re working with a solo agent, your ability to see that house, even if it’s remote and you’re having the agent take pictures for you, is limited by their hours in the day. But if you’ve got a team, they’ve got junior agents who are a lot more available to see that house and do that showing than if you’re working with one agent by themselves. Another thing is, you could speak to more, like you mentioned, you guys do a lot of deals. My team was doing over a hundred deals a year, so we saw everything. Whatever came up, let’s say a low appraisal, I knew a solo agent for whom an appraisal under the purchase price totally threw them for a loop. For us, it was no big deal because we dealt with it several times a year.
You’re a hundred percent spot on and we lean on each other. There are certain things that, as a team leader, I haven’t done before that I’m leaning on my team for. One of my team members is a retired CPA. We helped her buy two properties, one short-term rental, one personal property, before she moved down here from Boston and then got her license to join the team. She moved into a 55 plus community. I’ve been over there to hang out and it’s kind of cool, but it’s a whole different process when you’re buying one of those houses. Fast forward, we had a client two years ago looking to buy in a 55 plus community, and I was able to lean on her for all of her knowledge to help this client. She and I just partnered and she said, this is how it goes, the contract looks completely different, okay, we’re going to do it. It was completely different from a normal process. Because we have that team, we can lean on each other as opposed to trying to figure it out by yourself when you have that client’s trust.
That’s a really good point. Now, let’s say there’s a lesson you learned the hard way. Is there a task you held on to too long before finally delegating, and what pushed you to finally let it go?
One was invoicing. That’s one thing I was a little touchy on, for my short-term rental owners. I needed to make sure I saw each of these to make sure there wasn’t a discrepancy. That invoicing, when you go from four units to now managing over 25, can take up many hours in your day alone. You’ve got all these receipts and things coming in and you’re checking everything. That was one of the ones I was last to let go. When I did and I finally trained somebody on it, the time that opened up and the mental freedom, I didn’t realize, but it was almost making me not want to take on more short-term rental clients when people would raise their hand and ask if I was open to it. I’d try to make up some excuse, well, maybe you should manage it yourself, as opposed to jumping at it and saying yes, let’s do this. That was one of the things keeping me back, knowing this was going to be another headache of sending all these invoices. But now that I’ve moved it off, it’s been incredible. Another piece, I think I held on to doing the transaction coordination for way too long. I did it for the first two years in real estate before moving to a transaction coordinator. That would take up about four hours per deal to put all the documents in and then send all these agreements out and make sure everything’s getting signed. That was a mental weight as well. At that point I could probably only work with three, four clients at a time because I had to make sure all the dates were up and I was reminding people about upcoming dates, and I didn’t want to miss anything. But now adding that transaction coordinator into the team has been a game changer. Now I don’t have to think about any of that. They’re the ones sending all those messages. They put the dates right in our Follow Up Boss so we can see it at any time and it makes it so much easier.
I agree. Everything you’re saying is so wise. A lot of people hold on to finance and accounting stuff. People don’t want to let that go. The truth is that’s something other people can usually do pretty well, and they can’t actually move money, they’re just doing the paperwork associated with it. It doesn’t give them access to move money out of your bank or anything.
Hundred percent. There are so many controls now that you can put in place because we use QuickBooks for that. We pay our cleaners on the first and the fifteenth, and I used to be the one to look at all the notes and figure out how much, then send the payment. I thought on one of those elevate and delegate days, if this is taking a lot of time, how can I cut that whole time? Now I have my executive assistant. She puts all that together because she can see everything, all the cleanings, all of it. She puts it all together and sends an email to the cleaner with me CC’d to say, this is the amount we’re sending, does this look right to you? They tell her any discrepancies. Now I know the exact amount, and it only takes me five minutes to send payments to everybody on a Friday, which is amazing.
Love that. Now the last thing I want us to discuss is how you operate across multiple different states with your real estate team, Georgia, Florida, and Texas. Both for investors and agents, they often feel they’ve got to be able to touch the real estate. People have a lot of challenges with doing anything long distance. I’d love for you to share some wisdom on how you manage a business long distance.
I think this comes back to a little bit of my past. I was in medical device sales for seven years. During that time period I got promoted four times. The first promotion moved me from Philly to Chicago. Then I moved to Louisville, Kentucky, which is why I started investing there. Then I moved to Boston, and the last promotion moved me to Atlanta. In that whole time period I could have made the excuse that I was going to pause on investing because I couldn’t do it in my backyard in Boston, it was too expensive. But I just kept investing. When I was in Boston for three and a half years, I was able to build that portfolio from the three units I started out with to thirty through long distance investing. That got me comfortable with not having to be boots on the ground to see every single one of these properties. I just need to know that the numbers work, that there are checks and balances where I can send in an inspector to check out everything, and they’re going to give me a much more detailed report than I’d be able to see anyway, and I can use that to negotiate. When it comes to the real estate business, it’s very similar, especially in this niche. If we’re in a niche of more retail, where somebody’s going to make this their forever family home, it’d be a little different, where you have to go see every single one of these before you get it under contract. But we’re in the investment niche. What we focus on is making sure we’re really good at running the numbers, making sure we have a good idea of different neighborhoods, or have a specialist in that state who knows about the different neighborhoods they’re looking for. Once we find the deal, we put it under contract with enough days of due diligence that we can get out and see it once it’s under contract and make sure everything checks out. That’s kind of how we work it, and it’s been a joy. The first expansion wasn’t me saying we’re going to go take over the world. The first expansion happened because we had ten or eleven agents in Georgia, and one of them was moving back to Florida because her husband was going to pursue a PhD. I asked if she was still trying to practice real estate, and she said yes. Then some of the clients we helped in Georgia, once we mentioned we were now in Florida, reached out and said they actually wanted to buy a vacation home in Florida. We helped them, helped some others, and just kept growing from there. Then Texas was an agent who reached out specifically to join our team and expand us out there. Now we’re in Georgia, Florida, and Texas. It’s been amazing so far.
That is awesome. I love it. I can just hear throughout all your different experiences that you’re sharing, a few themes: team, leveraging other people, their skills, their wisdom, their experience, and not having fear, coming back to the numbers and not being afraid just because something is different or you haven’t done it before or it’s not how other people do it.
That’s the key. I think now more than ever, with the technology we have, especially being able to do a video walkthrough, being able to research even more detail than we ever could with some of these AI tools, there’s less excuse for investing far away or taking on something new. You’ve got more tools than anybody before us who built these amazing companies and businesses.
Very good point. So thank you so much for everything you’ve shared. If somebody would like to reach out to you because they’re looking to buy an investment property in these areas or looking for somebody to help manage theirs, what’s the best way for them to connect with you?
You can check us out at Ekabo Home dot com, which is EKABO Home dot com. It’s the same name on Instagram. You can Google me. We’d be happy to help you.
Love that. Of course, if you’re driving or anything, it’s all in the show notes or the caption below. Thank you so much. And for our listeners, thanks for joining us on another episode. Catch us again next week with another amazing guest.