He Bought His First Rental at 20. Now at 29, He Cash Flows $20K/Month.

0:00At 20 years old, Jefferson Simmons was kicked out of his frat house. The entire property was getting remodeled, and so he and 47 other college kids needed a place to live. After being discouraged by the rentals he saw in his area, he switched his Zillow tab from rent to buy and saw a$250 ,000 house for sale. But he was a sophomore in college. Could he really buy his first house? Thankfully, he had been saving up since high school. He pitched his parents to co-sign, and next thing you know, he was renovating a basement to put as many frat friends in there as possible. Suddenly, he was cash flowing$300 a month as a college kid.

0:40And now, just nine years later, Jefferson is financially free, with a rental portfolio of 17 properties, cash flowing$20 ,000 a month. He even ditched law school to go all in on rentals. He built partnerships on a low salary, and he did everything he could to scale. Today, we're going to get the full story with exact numbers, strategies, and techniques that Jefferson used to become a rental millionaire before 30 years old. And he's not done yet.

1:16Jefferson, welcome to the BiggerPockets podcast. Thanks so much for being here. Dave, thanks for having me. This has been a longtime dream of mine. Well, we're excited to hear about your story. This should be a lot of fun. So start by just telling us a little bit about yourself. How do you get involved in real estate in the first place? Yeah, I'm a 29-year-old Manhattan, Kansas-based real estate investor. I got involved in real estate kind of just by accident in college. When I was 20 years old, I was in a fraternity here, and we had a really generous donor that came in and did a nice renovation through our whole house.

1:52but everyone had to move out while that was being done. And so started looking around town for some places for my buddies and I to live because we had to figure it out for one year. And let me guess, no landlord wanted to rent to a bunch of frat guys. It was slim pickings out there. And then the ones that were excited to rent to us, I'm not a high maintenance guy, but they were not great options. So I don't know what prompted me to do it, but one day I was looking for rentals on Zillow. And for whatever reason, I just switched that little toggle from for rent to buy. And I found this house that I could see it was being mismarketed.

2:31It was listed as a three bed, three bath, but it was like 2 ,700 square feet. And I was like, that doesn't really make sense. And saw that it had three non-conforming bedrooms in the basement. And I was like, well, I could get a lot of guys in there. And the extent of my underwriting at the time was the little Zillow estimated payment versus I knew what landlords were trying to charge us in rent. And I was like, well, I can make a lot of money if I got a bunch of my buddies in here. And so launched into my real estate career with that one, which it was pretty unconventional. Well, the numbers must have been pretty compelling.

3:06Like how much did it say the estimated payment was on this house? And what was the purchase price? We ended up going back and forth, countering like seven times. And I put the house under contract at$178 ,000. Wow. Had it been sitting for a while? Yeah, about 60 days. And the thing is, you know, so many times realtors will tell you way too much information. And the listing agent told me, she was like, yeah, this guy bought this house for his son. They live out of state. The son was on the baseball team here. Now he's gone. They just need to get rid of it. So I knew it was a highly motivated seller.

3:43I negotiated so aggressively, largely out of necessity as well, because I had little to no money. It was, this is literally what I can afford to pay for it. And there's no working me up because there was no more money. Well, I mean, I was going to ask you that because very admirable that you decided to do this in college. But even if I had had that thought, I did not have any money when I was in college. uh you know working for minimum wage like did you have money or was this kind of like i'll find a deal and hopefully figure it out later i had a a small nest egg so i had planned to my deal with my parents was to pay for half my education on my own and so through high school i cut and sold firewood i was heavy into 4-h and ffa i did livestock projects up on the farm and then april right before i graduated high school i got a letter in the mail that i was going to get a full academic scholarship to K-State.

4:41Oh my God. Good for you. That's awesome. And so that was a blessing. And then I ended up going to school with a little bit of money in my pocket and it was enough, you know, to cover a down payment, but I was working at a restaurant in college. And so no bank was going to loan me or give me a mortgage when I was making 200 bucks a week. I can imagine that. And I went home and I just full disclosure, I pitched it to mom and dad. I was like, hey, I made my Excel spreadsheet and a little pro forma for the next 10 years. I was like, if I raise rents, and it's actually amazing now nine years later how accurate that first document has been.

5:19Was it? It's been a great, great asset. That's awesome. Good for you. Well, I guess an econ major got you something there. That's great. That's right. What were you planning to charge for rent to your buddies? My payment's still the same. So my mortgage every month is about$1 ,300. That's with everything? Insurance and taxes too? Yep. It's been a great house. You know, still own it today. And, you know, that first year I rented it for$1 ,600 and just been steadily increasing that rent over the years. And I have it rented right now through July of 2027 at$3 ,100 a month now. Wow. That's awesome.

5:55Man, you must be making serious cash flow there. Do you do it with a master lease or are you doing the co-living model where you're signing a bunch of leases right now? I do one group and they all put their names on the lease and then it's followed by a provision that says jointly and severally liable. Yeah, perfect. If one of them leaves, the roommates are on the hook for the rent. I found that they don't care if they bounce in the middle of the night if I'm mad at them, but if their buddies are irritated at them and saying, we got to cover your rent, they're they're a lot more likely to get current.

6:28Well, that's a great way to do it. And congrats. I love the just hustle spirit, like just figuring it out because you had to, you had nowhere to live. So did you do anything else while you were in college, real estate-wise? Yeah. So I closed on that house in May. I immediately took off and had an internship in Washington, DC that summer. And that's when I stumbled on the BiggerPockets podcast. I was sitting there in my office and everyone was at their desks with headphones in. I was like, what are you guys listening to at work? They were like, oh, you got to listen to podcasts. And I had never listened to anything.

7:03And I was like, well, what are they about? And they're like, anything that you're interested in. I'm like, well, I just bought a house. And so I searched real estate podcasts and I've been listening to the show for a long time. And at that point, were you thinking about wanting to be in real estate full time? or like what were your intentions to do with your econ degree? So I was econ and I was pre-law here at K-State. That's where I was headed. And then I came home and then that junior year, actually the house right next door to the one that I bought, I was over there working on some stuff and I lived on that street as well.

7:38The rental that I was renting was there. And there was a sign that went in the yard and it was a duplex and it was going to go on a bank foreclosure auction. And I got very, very excited when I saw that, but I had no money. I had absolutely nothing at that point. I mean, I was as broke as you could be. And so that's where this uncle comes into play. He had a bunch of C-class homes in a different city, and he was an attorney. He was a big mentor of mine growing up. He was selling his portfolio at the time, really looking at retirement. And so I hit him up. I said, hey, there's this property that's right next door to mine.

8:19It's going to go on an auction. I have no money. What do you think if we partnered on it? And he was really receptive. He was like, hey, I'm trying to get out of the business. But if you need a money partner, we can work something out. Yeah, for sure. He came into town. We looked at it together. We couldn't go in the house, you know. So we're peeking in the window, best we can see. And it was in pretty rough shape. We went to coffee. We sat down. and we were doing as much underwriting as we could. You know, this is what a kitchen's going to cost. It needs a new roof. And he was going to go on an international trip during the time that it was going to sell.

8:55And so he told me, he's like, hey, you're not going to be able to talk to me. I think we can afford to spend up to$140 ,000 on this after we finished our underwriting. He's like, but it's up to you. You know, I'm not going to be reachable. It's a lot of trust. Yeah, so I will not ever forget it. I had a little 125cc motorcycle in college. So I get done with class. I'm riding home on my motorcycle and I open up my laptop and it's time to try to buy a house. And I ran that thing up to about 100 ,000. And the listing agent reached out to me a few days later and said, hey, even though it did not meet the bank's reserve, they wanted to get rid of it.

9:35Really? Yeah. You know, it sounds like both of these deals. First one you did was kind of opportunistic. You just kind of born out of necessity. Second one, you just saw a sign, right? And did that. But you were also listening to the podcast at that point. Did you have a goal of what you were trying to accomplish with real estate? Or at this point, you're just kind of taking things as they came? Yeah. At that point, listening to BiggerPockets, I realized that this could be an avenue to really have a different type of lifestyle. And so, yeah, I was really inspired early on. And then, you know, also at the time, those deals were cash flowing.

10:13And so I was like, okay, what are my bottlenecks? Deals, then money. So I was just, I was really trying to learn as much as I could and then grow as fast as I could after that. Jefferson, want to hear about the second deal and how you've grown since then, but we do have to take a quick break. We'll be right back. As a host, the last thing I want to do or have time for is play accountant and banker. But that's what I was doing every weekend, flipping between a bunch of apps, bank statements, and receipts, trying to sort it all out by property and figuring out if I was actually making any money.

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14:54Welcome back to the BiggerPockets podcast. I'm Dave Meyer here with investor Jefferson Simmons talking about how he fell into his first property, started to scale with a partnership. How'd that second deal go for you? It went well. We did a full renovation on this duplex and it turned out beautiful. We scraped it down to the studs and really had a blank canvas to put this thing back together. And it was a real learning experience for me because I did a light rehab on my first one. But to go all in and do a full scale renovation on my second deal just grew me up really quickly. I found there was a building materials liquidation auction.

15:36And so went to an auction. You're like, I want one auction. I'm just going to keep bending stuff. Well, you know, a new set of cabinets at Home Depot was 15 grand. And so I went to this place and, you know, it was, you know, a whole set. It wasn't custom cabinets, but they were brand new, never used. And so I bought two sets of cabinets there for three grand each and little things like that, just always trying to find an edge to save some money. And that property turned out beautifully. Renovating a duplex, probably one of the best ways to make cashflow right now, you know, Find something that's not great or buy a single family, turn it into a duplex.

16:13But it can be intimidating, especially if you've never done this before. So maybe share with us some things you learned or some things you would do differently if you were just doing this for the first time. Yeah, we hired a general contractor for this project. And it was good that he was there because I did not know what I was doing. But I was there every day, trying to save money where I could, putting door handles on or if I could paint something. but I got to know a lot of the subcontractors through that project. And that was a turning point. I've done several rehabs since then and never used a general contractor since.

16:49Really? Okay. Yeah. So I just GC all my own projects, but Manhattan's a town of 50 ,000 people. There's three different companies that do tile. There's a handful of different painters. I know everyone on a first name basis. And so that was really the biggest turning point of that and allowed me to, do large rehabs for a lot better price moving forward. Absolutely. Yeah. Running your own subs is going to save you money if you're good at it. There's like a big caveat there. Like if you're not, just pay the GC. But yeah, if you're going to commit yourself to this and know how to do it, it's a great way to save some money on a rehab.

17:26And I assume it worked. You cash flowed it? It cash flowed. And same thing on that one. I was renting it for about$2 ,800 a month. and now it rents for like$3 ,500,$3 ,600 a month. That's awesome. Yeah. So at this point, were you like, screw law school, I'm not going to law school? Or like, what were you thinking about? Yeah, that's this part of the story. So shortly thereafter, I graduate my undergrad and I do take off for law school. And I was fortunate to graduate with my scholarship. I had no student loan debt coming out. And I remember sitting in my first class down there in law school, and they were talking about the bell curve of law school graduates, you know, where you graduated would determine what you're making.

18:11And I started thinking, I was like, I am not the smartest guy in this room and I'm going to leave here with a hundred thousand plus of student loan debt. I'd much rather have another mortgage that's going to be paying me back. Yeah. At least it's good debt. Yeah. That was a big decision and a big pride pill to swallow because a lot of everyone in my orbit thought I flunked out, but I was like, I'm going to go home and chase this real estate dream. And so I left after one semester. I was pretty confident. I had done two deals. I had the proof of concept. I was sure the path that I wanted to go down at that point.

18:49What was your plan for living though? Cause you know, cashflow great, right? But you're, sounds like you're making a couple hundred bucks at most, right? Probably not enough to cover your living expenses. So how, you know, were you going to wholesale or flip or how did you plan to survive? I did graduate my undergrad. So I had a bachelor's degree. And so I was like, you know what, now I'm done with school. It's time to go get a job. So I worked as an underwriter at an insurance company for a couple of years. But when I was doing that though, I was always looking at deals and decided to go ahead and get my real estate license at the same time.

19:24And so during my second year there, I was showing houses on nights and weekends as well. And so, you know, at my insurance job, I was only making$42 ,000 a year. So two sides of that coin wasn't a lot of money to deploy into real estate. But at the same time, it didn't take that many deals to replace my income. What kind of deals were you looking for at that point for yourself, for your personal portfolio? You know, I had big dreams. I would see apartment complexes that were, you know, sixplex or 12plex come up for sale. And that was bigger than anything even my mentor, my uncle had done at that point.

19:59And so I really didn't have anyone to lean on for something like that. So really just drilled into the single family homes. And that's what I did for several years and got to be really good at that. I had been walking up and down that street all the time doing that second rehab. And one day the woman that lived across the street from me just knocked on my door and said, hey, my husband and I are moving to California to be closer to our kids. Do you fix up houses? And I was like, yeah, I do. I do. I'm a real estate investor now. And so she goes, why don't you come over and tell me what you give me for my house?

20:36So I walked over there. I looked at it and I offered her 150. And she said, I have a friend that's a realtor. And they told me it's worth at least 200. So they listed it for, I think, 210. And it sat there for six months. They dropped the price, dropped the price. And I remember I would come home from work and I would sit in my living room. I had big windows right there. And I would just pull the curtains and look to see if people were coming to do showings. And finally, they lowered the price down to like$168. And I could see we were starting to get more traffic on that street. Okay. So I approached her again.

21:12And if you think, they've been sitting on it for six months, still paying the property taxes. they weren't there anymore. So I reached out to her. I just said, hey, my offer of 150 is still good as is. And they took that. Nice. That's great. Well, I think this is a really good example and lesson about how to operate in the market today, because we're going to see more and more of this. They might not take that deal right away. No one who thinks their house is worth 210 is going to accept the 150 day one. It's just not going to happen. Sometimes a dose reality is required because it sounds like you were pretty close on with your your first underwriting of what it's worth.

21:50Sellers aren't always going to be there right away. And it takes a little time of things sitting on the market. And so if you make these kind of offers and you feel confident that you're not trying to, you know, take advantage of someone, but you're offering a fair price for what you need to buy it for, you're going to have to be patient. But things will come around like that's the benefit of making these offers now because you might not get one for three months or four months, but six months from now, you might get a call. And then nine months from now, you might get another call. And I just think that this is a really important skill for everyone who wants to be buying right now in 2026 to be working on.

22:25So how'd that one work out? That one, when I look back, everyone likes to romanticize, you know, how hard they worked and everything. But that one, I was doing a lot of it myself. And the rehab took me a little over six months. And so at that point, when I was still early in my career, it wasn't like I was rolling in cashflow. I remember every single paycheck I got was just going towards funding the mortgage for an empty house or my rehab because I funded that with my own cash. And so looking back, that one is really sweet. Now it rents great. I have$200 ,000 all into it and it rents for$2 ,600 a month now.

23:04Amazing. So yeah. And it sounds like it sort of became a template for you. Is that right? Like something you're like, I can do this. I can repeat this model. I fell into what I think a lot of investors do, which is I was like, I'm going to buy one house every single year and just keep saving up for the next down payment, next down payment. Then I realized that's really a limiting belief. I ended up finding a private money partner down the road, which really allowed me to exponentially expand my portfolio after that. Well, good for you, Jefferson. Sounds like you positioned yourself where you can start to scale and really start to go after your bigger real estate goals.

23:39We're going to hear about that right after this quick break. Stick with us. Quick gut check. If your investments are generating income, how much of that are you actually keeping? Because a lot of people, they focus on yield and ignore tax impact completely. Multifamily real estate, though, tends to solve for both. You get cash flow, and with depreciation, you may be able to reduce your taxable income at the same time. That's the approach BAM Capital takes. They're not chasing flashy deals. BAM focuses on the long game, prioritizing steady execution and the potential for tax efficiency over time.

24:15For accredited investors who want real estate exposure without the day-to-day work, it's a model worth looking at. Learn more at biggerpockets.com slash BAM. Only for accredited investors, past performance is not indicative of future results. If my house had a resume, it would probably say great at structure and not much else. I'm the one paying the mortgage. My house mostly just stands there looking supportive. When you're away, it doesn't actually have to sit empty though. You can list your space on Airbnb. And now Airbnb has something called the co-host network, which makes it a lot easier to do.