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

At 20 years old, Jefferson Simmons was kicked out of his frat house. The entire property was getting remodeled, so he and 47 other college kids needed a place to live. Time to rent…right? After being discouraged by the rentals in his area, he switched his Zillow tab from “Rent” to “Buy” and saw a $250K house for sale. He was a sophomore in college. Could he really buy his first house? Thankfully, he had been saving up for tuition since high school, but an academic scholarship now put the entire down payment in his hands. He pitched his parents on cosigning, and next thing you know, he was renovating a basement to fit as many frat friends as possible. Now, just nine years later, Jefferson is financially free, with a rental portfolio generating $20,000/month in cash flow, all before the age of thirty. Today, Jefferson shares why he ditched law school to invest, the one thing that helped him scale his portfolio way faster, and how he’s consistently found underpriced deals that give him stellar returns. In This Episode We Cover How to buy your first rental, even if you’re young, and even if you have little money The partnership every new investor should look for to keep growing An expensive lesson Jefferson learned on his second real estate deal (huge renovation) Is dropping out of school worth it to invest in real estate? Why Jefferson did it Why you should always make a low offer even if it doesn’t get accepted (at first) The secret to scaling faster when you want to buy more than one rental per year And So Much More! Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ⁠⁠⁠h⁠ttps://www⁠.biggerpockets.com/blog/real-estate-1270. Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠[email protected]⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Learn more about your ad choices. Visit megaphone.fm/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Dave Meyer?

  At 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 cosign 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.

• 0:40Dave Meyer?

  And 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. Jefferson, welcome to the BiggerPockets Podcast. Thanks so much for being here.

• 1:20Speaker 01

  Dave, thanks for having me. This has been a longtime dream of mine.

• 1:24Dave Meyer?

  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 did you get involved in real estate in the first place?

• 1:32Speaker 01

  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, but 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.

• 2:03Dave Meyer?

  And let me guess, no landlord wanted to rent to a bunch of frat guys?

• 2:06Speaker 01

  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.

• 2:14Dave Meyer?

  Okay.

• 2:15Speaker 01

  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 to buy. And I found this house that I could see it was being mis marketed. It was listed as a three bed, three bath. But it was like 2,700 square feet.

• 2:35Dave Meyer?

  Yeah.

• 2:36Speaker 01

  I was like, that doesn't really make sense and saw that it had three nonconforming bedrooms in the basement. And it's 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.

• 3:04Dave Meyer?

  Well, the numbers must have been pretty compelling. Like, how much did it say the estimated payment was on this house? And what was the purchase price?

• 3:11Speaker 01

  We ended up going back and forth countering like seven times. And I I put the house under contract at $178,000.

• 3:19Dave Meyer?

  Wow. Had it been sitting for a while?

• 3:22Speaker 01

  Yeah, about 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 motive, highly motivated seller. I 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.

• 3:56Dave Meyer?

  Well, I mean, I was gonna 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.

• 4:16Speaker 01

  I had a a small nest egg, so I had planned. Into 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 4H 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.

• 4:41Dave Meyer?

  Oh, my God. Good for you. That's awesome.

• 4:43Speaker 01

  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.

• 4:58Dave Meyer?

  Yeah, I could imagine that.

• 5:00Speaker 01

  And I went home and I just full disclosure, I pitched it to mom and dad. I was like, hey, you know, I made my Excel spreadsheet and, you know, a little pro forma for the next 10 years. I was like, you know, if I, if I raise rents and it's actually amazing, you know, now nine years later, how accurate that first document has been.

• 5:19Dave Meyer?

  Was it?

• 5:20Speaker 01

  It's been a great, great asset. So.

• 5:23Dave Meyer?

  That's awesome. Good for you. Well, I guess a econ major got you something there. That's great.

• 5:27Speaker 01

  That's right.

• 5:28Dave Meyer?

  What were you planning to charge for rent to your buddies?

• 5:32Speaker 01

  My payment's still the same. So my mortgage every month is about 1,300 bucks.

• 5:36Dave Meyer?

  That's with everything, insurance and taxes too?

• 5:38Speaker 01

  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.

• 5:53Dave Meyer?

  Wow, that's awesome. Man, you must be making serious cash flow there. Do you like, 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?

• 6:04Speaker 01

  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.

• 6:11Dave Meyer?

  Yeah, perfect.

• 6:12Speaker 01

  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, uh, they're, they're a lot more likely to, to get current.

• 6:28Dave Meyer?

  Well, that's a great way to do it and congrats. Like 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?

• 6:40Speaker 01

  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're like, oh, you gotta, gotta listen to podcasts. And I had never listened to anything. And 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.

• 7:14Dave Meyer?

  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?

• 7:22Speaker 01

  So I was, 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. The 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, this uncle comes into play.

• 8:00Speaker 01

  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, you know, really looking at retirement. And so I hit him up. I said, hey, there's this, there's this property that's right next door to mine. It'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, I'm trying to get out of the business. But if you need a money partner, we can work something out.

• 8:33Dave Meyer?

  Yeah, for sure.

• 8:33Speaker 01

  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 and we sat down. 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 gonna go on an international trip during the time that it was gonna sell. And so he told me, he's like, hey, you're not gonna be able to to talk to me. I think we can afford to spend up to $140,000 on this after we did finish our underwriting. He's like, but it's up to you, you know, I'm not gonna be reachable.

• 9:08Dave Meyer?

  It's a lot of trust.

• 9:09Speaker 01

  Yeah, so I will not ever forget it. I remember 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.

• 9:34Dave Meyer?

  Oh.

• 9:34Speaker 01

  They wanted to get rid of it.

• 9:35Dave Meyer?

  Really?

• 9:35Speaker 01

  So, yeah.

• 9:37Dave Meyer?

  You know, it sounds like both of these deals, first one you did is kind of opportunistic, like you're 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?

• 9:58Speaker 01

  Yeah, at that point, listening to BiggerPockets, I realized that this could be an avenue, you know, to really have a different type of lifestyle. And so, yeah, I was, I was really inspired early on. And then, you know, also at the time, those deals were cash flowing. And so I was like, okay, what are my bottlenecks? Deals, then money.

• 10:20Speaker 01

  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.

• 10:26Dave Meyer?

  Jefferson, wanna 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. Then I found Baseline and it takes all of that off my plate. It's BiggerPockets' official banking platform that automatically sorts my transactions. Actions, matches receipts and shows me cash flow for every property. My tax prep is done and my weekends are mine again.

• 11:07Dave Meyer?

  Plus, I'm saving a ton of money on banking fees and apps that I don't need anymore. Get $100 bonus when you sign up today at baselane.com/bp. BiggerPockets Pro members also get a free upgrade to Baseline Smart. It's packed with advanced automations and features to save you even more time. Most investors only think about insurance when something goes wrong. A tenant injury, storm damage, loss of rent. Then suddenly, the cheapest policy doesn't feel like the best one anymore. That's why a lot of BiggerPockets investors use steadily for landlord insurance, designed specifically for rental properties. Whether you own one property or a growing portfolio, they make it simple to get covered properly.

• 11:51Dave Meyer?

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• 12:43Henry Washington?

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• 15:01Dave Meyer?

  Welcome 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?

• 15:14Speaker 01

  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 and so went to an auction.

• 15:45Dave Meyer?

  You're like, I want one auction. I'm just gonna keep bidding that stuff.

• 15:48Speaker 01

  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.

• 16:12Dave Meyer?

  Renovating a duplex, probably one of the best ways to make cash flow right now. You know, find something that's not great or add, you know, buy a single family, turn it into a duplex. But 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 have, you'd do differently if you were just doing this for the first time.

• 16:30Speaker 01

  Yeah, we, 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, you know, trying to save money where I could, you know, 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.

• 16:55Dave Meyer?

  Really? Okay.

• 16:56Speaker 01

  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, you know, a handful of different painters. I know everyone by, on a first name basis. And so that was, that was really the, the biggest turning point of that. And allowed me to do large rehabs for a lot better price moving forward.

• 17:19Dave Meyer?

  Absolutely. Yeah. Running your own subs is gonna 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. And I assume it worked. You cash flowed it?

• 17:35Speaker 01

  It cash flowed and same thing on that one. I was, I was renting it for about 2,800 a month. And now it rents for like 35, 3600 a month.

• 17:45Dave Meyer?

  That's awesome.

• 17:46Speaker 01

  Yeah.

• 17:46Dave Meyer?

  So at this point, were you like, screw law school? I'm not going to law school. Like, what were you thinking of that?

• 17:51Speaker 01

  Yeah, that's this part of the story. So shortly thereafter, I graduate my undergrad and I do take off for law school. And, you know, I was fortunate to graduate with my scholarship. I had no student loan debt coming out. And I remember sitting in, you know, my, 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. And I started thinking, I was like, I am not the smartest guy in this room. And I'm going to leave here with 100,000 plus of student loan debt. I'd much rather have another mortgage that's going to be paying me back.

• 18:31Dave Meyer?

  Yeah, at least it's good debt.

• 18:33Speaker 01

  Yeah, that was a, 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, I left after one semester.

• 18:47Dave Meyer?

  Wow.

• 18:47Speaker 01

  I was pretty confident, you know, I had done two deals. I had the proof of concept. I, I was sure the path that I wanted to go down at that point.

• 18:56Dave Meyer?

  What was your plan for living though? Cause you know, cash flow, great, right? But you're, it 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?

• 19:11Speaker 01

  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.

• 19:30Dave Meyer?

  Nice. Okay.

• 19:31Speaker 01

  And 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.

• 19:49Dave Meyer?

  What kind of deals were you looking for at that point for yourself, for your personal portfolio?

• 19:52Speaker 01

  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, you know, my mentor, my uncle had done at that point. And 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.

• 20:37Speaker 01

  And so she goes, why don't you come over and tell me what you give me for my house? So 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 that we're starting to get more traffic on that street. So I approached her again. And if you think, you know, they've been

• 21:20Speaker 01

  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.

• 21:29Dave Meyer?

  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 the day one. It's just not going to happen. Sometimes a dose of reality is required because it sounds like you were pretty close on with your, your first underwriting of what it's worth. Sellers aren't always going to be there right away and it takes a little time of the things sitting on the market. And so if you make these kinds 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.

• 22:14Dave Meyer?

  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. So how'd that one work out?

• 22:33Speaker 01

  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 cash flow. I was, I remember every single paycheck I got was just going towards funding, you know, the mortgage for an empty house or my rehab because I, I funded that with my own cash. And so looking back, you know, that one is really sweet. Now it rents great. You know, I have 200,000 all into it and it rents for 2,600 a month now.

• 23:10Dave Meyer?

  Amazing.

• 23:11Speaker 01

  So, yeah.

• 23:12Dave Meyer?

  And it sounds like it sort of became a template for you. Is that right? Like something you're like, I, I can do this. I can repeat this model.

• 23:18Speaker 01

  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, you know, just keep saving up for the next down payment, next down payment. Then I realized that's really a limiting belief. I, I ended up finding a private money partner down the road, which really allowed me to exponentially expand my portfolio after that.

• 23:38Dave Meyer?

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• 27:22Dave Meyer?

  Welcome back to the BiggerPockets Podcast, here with Jefferson Simmons, talking about how he went from sort of accidental landlord into someone with big ambitions in the real estate space. So where we left off, Jefferson, you were talking about how you sort of figured out, you know, a model that was working for you and how you might be able to scale up. So tell us how you went from, you know, one deal a year, you know, partnering, doing a lot of things yourself, into scaling a bigger portfolio.

• 27:50Speaker 01

  So I mentioned I was working two jobs, being a Realtor and working at the insurance company, as well as, you know, I was doing these projects on my own and then I started to help my own With some of his portfolio, he in 2019 bought a 12 unit. It was our first venture into multiplexes together and he let me sweat in. I got to sweat in 10%. I helped him renovate the entire thing. We, we went in and did new kitchens and everything, new floors, new paint. And that was a, a big deal and really allowed me to start making a little bit more money without coming up with a lot of my own money. And that was a three year rehab. But at that point, I was starting to make a little bit of money and, you know, get into 2020 COVID.

• 28:34Speaker 01

  The stock market crashed and I was realizing, hey, I love this real estate angle, but there's an opportunity to make some good money in the market right now. And so at that point, changed course for, you know, several months and, and started funneling some cash into the market.

• 28:51Dave Meyer?

  Were you buying individual stocks?

• 28:53Speaker 01

  Yeah, I have a high risk tolerance. So I was buying a lot of individual stocks.

• 28:59Dave Meyer?

  You're trading options?

• 29:00Speaker 01

  Yeah, I was, I was, I was very speculative. So that was actually when Elon was gonna buy Twitter. I think Tesla fell down to like a hundred and five dollars a share. And I thought that was absolutely ridiculous. I bought a, a bunch of Tesla call options.

• 29:15Dave Meyer?

  Yeah.

• 29:15Speaker 01

  And it, the stock like doubled in the next six weeks. But I had ridden that wave a little bit at that point. And I was like, you know, this is, those numbers on the screen can just disappear. And so right after that trade, I took all my profits out on that and I bought two single family houses cash.

• 29:32Dave Meyer?

  I love it.

• 29:32Speaker 01

  With those proceeds, yeah.

• 29:34Dave Meyer?

  Yeah, I invested in the stock market. It's great, but you're right. Like it's just so volatile. I love the idea of just taking profit when you know you had a big win and then putting it into something a little bit more stable. And were you still working at that time?

• 29:46Speaker 01

  I left the insurance company and I was all in on building my real estate portfolio there for a little while because I was doing a couple of active rehabs. I was trying to still source deals and it was a lot at once. And I took, oh, maybe about a 10 month hiatus. And then I ended up going back to work at the university. I was raising money for the local university here for a few years.

• 30:10Dave Meyer?

  Cool. Nice. I know you're still doing that.

• 30:12Speaker 01

  No, I just, I just left that at the end of last year and now I'm running my portfolio again full time.

• 30:17Dave Meyer?

  Back full time. Calls you back.

• 30:19Speaker 01

  That's right. Yeah.

• 30:20Dave Meyer?

  So what does your portfolio look like today?

• 30:23Speaker 01

  Yeah, I have now 17 different properties or 17 parcels. That's $39. I own 100% of that except for I'm a minority partner on a 15 unit with a few buddies. And all in all, it's around $20,000 a month in cash flow.

• 30:40Dave Meyer?

  That's amazing. So when you got a goal and you started thinking, you know, I want to live this life of abundance, like, how close are you to reaching that? Are you just going to keep scaling?

• 30:50Speaker 01

  Well, I'm a, I'm a single guy. I, I have enough, you know, for myself right now. I, I hope that my life situation will change at some point. But I'm also, I'm an ambitious person. I, I don't want to just sit around and lay on the couch all day either. I, I love being out in the community, meeting neighbors, potential future deals, talking to people about maybe funding future deals. I just, I'm a very social person. I'm an ambitious person and I, I see no reason to stop.

• 31:17Dave Meyer?

  Yeah. Good for you. That's great. I mean, you just seem to love it. Like, I think that's, everyone has different goals. That's what we talk about on the show all the time. You want to do real estate, to, you know, buy two properties to supplement your income? Great. You want to go into it full time because you really enjoy it? Awesome. Like you, that's what's so cool about it is that there's just so much flexibility. What are the deals that get you excited right now? Like, what are you really looking forward to doing in the next year?

• 31:40Speaker 01

  One thing that I ought to mention really helped me accelerate after that one summer that I bought a lot. I just had a lot more confidence as an investor.

• 31:49Dave Meyer?

  Yeah.

• 31:49Speaker 01

  I was, I had done several rehabs. I was managing a lot of tenants and I really got the confidence where I was like, I feel like I can ask people for money now.

• 31:59Dave Meyer?

  Yeah, right.

• 32:00Speaker 01

  I, I, so I was an agent. I was helping a client in Texas that he wanted a house for football games here in the fall. And it was when the market was so hot, I remember opening Zillow, thinking Zillow was broken because every single listing you'd click on said pending.

• 32:17Dave Meyer?

  It's already gone. Yeah.

• 32:18Speaker 01

  Yeah, it was, things were selling over. Market, same day. It was, it was absolute craziness. And this client, he wanted me to basically walk a property that might come up and vet it for him. And then he wanted to get on a plane and come see it if it was a good option. And things were just moving way too fast for, for that to work. And so we went through this for a few months and I could sense he was getting frustrated. And just the way things ended up, I had a house that I had just purchased 10 months before. Uh, with, with those stock proceeds that I felt like I had gotten a great deal on. And I had a young couple that I had put in there and they reached out to me and they said, hey, we just found our forever home. Is there any chance you'd let us out of our lease early?

• 33:03Speaker 01

  And we can go buy this house. And I mean, this is a small town, you know, your reputation's worth a lot. I didn't want to hold them hostage in a house they didn't want to be in. So I just told them like, I'm like, yeah, hey, you guys cover the utilities till I find a new tenant. Absolutely. That's, that's fine. So I have this now vacant house and I knew my client was going to be a cash buyer. And so I just had this idea and asked him, I said, hey, when's next time you're coming to town? We set up a meeting when he was there and I took him to dinner. I said, hey, I want to pitch you on something kind of unconventional. I have this house that I feel like I got a great deal on 10 months ago. I think it would fit basically exactly what you're looking for in your price point.

• 33:47Speaker 01

  I'm trying to be in growth mode right now, not sell mode. But I have this idea. I will either sell it to you for $25,000 more than I bought it for. And say that's a great 10 months, the rent I collected for that. But this is also less than a year. I'm going to have short-term capital gains on that. Or I said, I'll sell it to you for exactly what I bought it for and not make any money on you. But would you consider, uh, writing me a $200,000 line of credit?

• 34:16Dave Meyer?

  Whoa, I like that.

• 34:18Speaker 01

  Yeah. So he, uh, he kind of chuckled. He goes, he goes, wow, you're very direct. And he said, he said, why don't we get coffee in the morning and go look at the house and I'll call my wife. We went and got coffee. He FaceTimed his wife. They walked. Through the house and I just waited outside on the driveway and he came outside and he shook my hand. He's like, hey, we'll do it. And so that was great.

• 34:38Dave Meyer?

  I love that.

• 34:39Speaker 01

  That was incredible.

• 34:40Dave Meyer?

  That's such a creative, awesome way of creating, again, a win-win situation, right?

• 34:45Speaker 01

  Exactly.

• 34:46Dave Meyer?

  Didn't try and get both. You weren't trying to get a profit and the line of credit. You figured out something that your client wanted, asked for something you wanted in return and it works for both of you.

• 34:55Speaker 01

  It's been a great partnership. So, you know, three months later, I found this little house for $171,000 and he wired the entire balance.

• 35:04Dave Meyer?

  Amazing.

• 35:05Speaker 01

  The day of closing. So no appraisals, you know, no, all those bank fees and things like that. And I do pay him seven and a quarter. But that's great. You know, it's more than he's getting on T bills. It's less than I probably be paying at the bank. And, you know, at that point I was like, okay, you know, I bought $171,000 house. I had the $200,000 line of credit. Is that done? And, you know, about a year went by and he called me one day and he said, hey, you seen anything in Manhattan? I'm like, yeah, I got two houses that I'm looking at right now. He said, if you need, need any help on those, holler at me. And so we've done a few more deals together since then.

• 35:41Dave Meyer?

  That's awesome.

• 35:42Speaker 01

  Yeah, that's been a great partnership and we're, we're friends as well.

• 35:46Dave Meyer?

  I love the way that you're approaching partnerships and just trying to find these win-win things. Not only does it get you what you want, but it's fun. It's fun working with people, I, I think, and just figuring out these ways to get creative and help not just yourself, but someone else reach their financial goals at the same time. Like that's just a, one of the more rewarding things that you can do in this industry.

• 36:06Speaker 01

  Right.

• 36:07Dave Meyer?

  Well, thank you so much for being here, Jefferson. This has been a lot of fun. Last question for you. How would you say BiggerPockets has contributed to your growth, if it has at all?

• 36:16Speaker 01

  It's, it's been extremely instrumental. I, I was so oblivious when I first started out. I remember, you know, as I had a few houses, I was writing leases for full 365 days. And so I was, you know, at nine o'clock on July 31st, I had to go in there, clean, you know, do paint touch-ups for my August 1st move-ins the very next day. And so just little Things like, you know, knowing to get tenants out three days in advance or making sure that they hire professional cleaning company. So that way I don't have to be in there recruiting my mom and my cousins and little things like that. I was using a cozy at the time was bought by apartments.com do all my rent collection online now. No more arguing back and forth with

• 37:01Speaker 01

  tenants. Hey, the check was in the mail. I don't have to pay the late fee. It's it either was or wasn't there on the online portal on the fourth. So yeah, those just little tips and tricks there have been incredible. And yeah.

• 37:16Dave Meyer?

  Awesome. Well, thank you so much for Jefferson for being here. Congratulations on all your success and best of luck to you. We really appreciate your time.

• 37:24Speaker 01

  Thanks, Dave. Appreciate it.

• 37:25Dave Meyer?

  And thank you all so much for watching this episode of the BiggerPockets Podcast. We'll see y'all next time.