I Bought 3 Rentals Then Ran Out of Money…Now I Have 50 Units

Retirement seemed wayThis investor acquired 50 units and only put 1% down all since 2021. No tricks, no scams, not even extreme leverage. Just a lot of hustle to find the right deals and the courage to seek out partnerships within her network. Stick around to hear how she went from a demanding job running a makeup salon onto the path towards early retirement. Hey everyone, I’m Dave Meyer. I’ve been investing in rental properties for 15 years now, and I’m the head of real estate investing here at BiggerPockets. Our guest on the show today is Investor Jesse Dylan. Jesse lives in Massachusetts and had a hands-on day job owning a small business in 2021, which she discovered real estate investing. And now less than five years later, she’s completely transformed her financial future with a portfolio of only seven properties. In this episode, Jesse will tell us how sending a few awkward text messages completely changed her investing trajectory, why her partners are excited to bring all the necessary cash to acquire new properties, and why she’s now pivoting back to cashflow after accomplishing her biggest investing goal. This is a truly inspiring story that really emphasizes the power of finding like-minded people you might already know within your own network. Let’s bring on Jesse to hear how she does it. Jesse, welcome to the BiggerPockets podcast. Thank you for being here.Yes, thank you for having me.I’m excited to have this conversation with you. Start by telling us a little bit about yourself and where were you in life when you first started thinking about real estate investing?So I’m Jesse Dillon. I live in Central Massachusetts. Half of my time I spend in real estate and the other half I spend working in and operating my permanent makeup studio. So going back to 2020, when I was forced to close for a couple months in the studio, I realized how burnt out I was, and that sort of sent me down the path of figuring out how do people retire. And a Facebook clickbait article actually led me to an Instagram account of a girl who was set to retire at 26. So I’m like, I got to figure out what she’s doing. And I messaged her and I told her all about my situation and how inspiring her article was. And I was like, if you could recommend one book, what would it be? And she said, the simple path to wealth. So I read that loved it went crazy, investing in index funds.
I was investing 70% of my income. And then I realized that was still going to take me 11 years of going that hard to retire that way. And I was like, there’s no way I can keep this up for 11 years. And one podcast led to the next and someone was talking about real estate and the guy who was talking started off by saying, you don’t have to have family in real estate. You don’t have to already be wealthy, you don’t have to be a certain age. And all of these things were mind blowing to me. I like everyone else, thought that real estate investing was for a specific group of people that I wasn’t a part of because I didn’t have experience, I didn’t really have a whole lot of money, and he actually pointed all the listeners to BiggerPockets. So I just went crazy fall 2021. I did all the bootcamps, I did all the books and the podcasts and the coaching calls, and I just totally became a student of real estate. And that was for a couple months leading up to offering on my first property.So after all the bootcamps, all the books, what did you target for your first deal?So staying close to home just felt safe to me. I didn’t stick with that for very long. I do live in an expensive market, but staying close to home for my first one, felt safe. Multifamily felt safer than single family because having more than one unit, I just felt more diversified If one was vacant, I wasn’t completely underwater. And I looked at how much money I had to get started with. So I started offering on properties Thanksgiving weekend 2021, and I closed on my first one, January of 2022. It was a two family about 20 minutes away from me. It was a great deal. It was listed at four 10 appraised for four 20, but I got it for 3 57.Wow.So I got a pretty good deal.How in 2021 it was pretty hard to get something at a discount. How’d you do that?I think it was just on the market for the perfect amount of time. I think it was kind of a unique property that a lot of owner occupants wouldn’t be interested in, but I also went straight to the listing agent and I think that made a big difference. I do think that was kind of a risky move for my first purchase ever. I was still renting at this time. I had never bought any property, but I went straight to the listing agent. So I got to really get a feel for what creative things I could put in the offer that would appeal to the seller. And we got to really build rapport. I think that made the difference.And were you planning to owner occupy or were you going to keep renting?No, I was going to keep renting. I had a really great deal on rent actually, so it was going to take a lot to get me out of that situation. I did end up house hacking later, but for my first two purchases, I actually continued renting.I like that. I think that’s somewhat of a contrarian view right now. I think a lot of people want to move right into their first investment, which can make sense for most people. But how did you think through that decision?Yeah, for that first deal, I just ran the numbers and I more so ran it for how should this property be performing, not how is it performing today. There was an inherited tenant who was paying well below market rent, but I was like, if I can just hang on while we bring that person closer to market rent, then this will be a really good investment. It’s not going to be a home run the day that I close, but I’m thinking more one year, two year, three years down the line, that’s when I really need it to be performing well,Which is the right perspective to have. I mean, it’s very difficult even as we’re going into a buyer’s market, super hard to find deals that are both operating the right way as they should and are priced well. Either you’re going to get something that is priced well and you’re going to have to do the work to get it to operate or it’s going to be priced appropriately and you’re going to pay for the fact that the previous operator was doing a good job. So I think what you’ve done and the kind of deal you targeted is perfect for someone on your first deal. It’s a great way to learn and it allows you to buy at a little bit lower price and have more upside on the deal. What other metrics were you targeting? Was there a specific cash on cash return or were you trying to build equity? What attracted you other than price to the specific property?So I still go into all long-term rentals with the attitude of within a couple years, do I think this could cashflow a true net profit of $500 per month per unit?That’s awesome. Yeah.There are a couple other standards that I shoot for in addition to that now, but that continues to kind of be my baseline because my ultimate cashflow goal is 15,000 a month. So I know if I can buy properties that are going to cashflow 500 a month per unit, if I’m buying them now in these 50 50 partnerships, it’s easy to back into how many units I need to buy. I do think unit count can be kind of arbitrary, but that makes it easy for me to know where the finish line is.I on this podcast rail against unit count all the time because I think it’s very silly because I know people who have 10 units who perform better than people who have 80 units all the time. But what you’re doing makes total sense. You’ve set a benchmark for performance, so you’re not growing units just for the sake of it. You’ve set a quality standard for each one of those units. And if you have a unit count goal based on them performing at a high level, then that makes total sense to me. And I guess is your goal then 30 units, 30 suchUnits? Well, my goal was 50 units with most of them being owned in 50 50 partnerships because after I did my first three deals alone, I was tapped out for down payments and that’s when I pivoted into buying and partnerships. So I kind of backed into, if I build the rest of my portfolio in these partnerships, I’ll need about 50 total units to be where I want to be.We’d love to hear about those partnerships, but were the second and third properties you did similar to that first one,Not too far off. So the second one was a single family home a couple hours away that I bought as a vacation rental. Nice. And the third one was my house hack. So it’s a two family. I have a long-term tenant on one side, and then I also midterm rent my guestRoom. Oh, cool. Wow. You’re doing it all. Short-term rental. Midterm rental, long-term rental on three deals. That’s great. Well, it sounds like an amazing start to your investing career, but I want to hear about how you scaled because you mentioned being tapped out, which is a point that all of us get to. I’d love to hear how you navigated through that, but we got to take a quick break. We’ll be right back. All right. Let’s talk about something. We have all dealt with funding that takes forever. You got the property lined up, the numbers make sense, everything is ready to go. But the funding, that’s often where things start falling apart. Either it’s too slow, too rigid, or just way more complicated than it needs to be. But here’s the thing, it doesn’t have to be this way. I want to tell you about Express Capital financing.
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And the first piece of that was figuring out who the right partner is for me. So I worked out in my head like, well, what do I bring to the table and what would this look like in a perfect situation? And I knew I wanted a partner that wasn’t really going to micromanage me, that was going to trust the process and trust that I was doing my share. I wanted to be the person essentially doing all the work, and I needed somebody else to bring in the capital for the deal. So when I got home from VP Con that year, I made a list of 50 people who I thought they would probably know. Someone who understands the wealth building power of real estate, probably knows that their money’s not working hard enough for them in the stock market. They understand investing, they’re aggressive, but they’re too busy to be doing the day-to-day work of real estate investing.
So I made the list of 50 people who I bet they probably know someone. And every day I sat down and I texted five people from the list. First thing before I did anything else, I had a copy paste message. And it was something like, I know we’re connected online, so you’ve probably seen that I’ve been doing X, Y, Z and real estate investing. This is what I’m looking to do next. If you happen to know someone who fits X, Y, Z description, would you just send them my info and we can have a tough conversation, see if it might be a good fit? No worries. If not, hope all is well with you. So I left it in a way where if they didn’t want to respond, it wasn’t awkward. Most people didn’t respond and that’s fine. But one person was sitting at dinner with her friend and her friend was the perfect fit.
She fit the description perfectly and she was like, this is so crazy. So we had a couple phone calls we met for coffee, our goals lined up perfect. And what made me realize this totally is the perfect partnership is that we both felt like we were getting the better end of the deal. We both felt like it was almost unfair to the other person and just such a no-brainer. So about nine months after that, we closed on a 13 unit long distance together. Whoa. Today we have over a million dollars worth of equity in that property.In one property.Yeah.Oh my god.Whoa. And we’re projecting that we will, by the time it’s really optimized, have over 2 million of equity. So when I joked with Amelia and Grace from WireThatThat was a million dollar textLiterally. Right. That’s unbelievable.Isn’t that crazy?I just want to commend you, that is one of the coolest strategies that we’ve heard. I’ve heard on this podcast about how to scale. Because first and foremost, like you said, this is something everyone faces, but no one likes to admit that you run into. But unless you have a trust fund, even if you have a high paying job, most people will run into a point where you can’t scale as quickly as you want to. If you’re as aggressive as Jesse did, and I understand that you may not know someone off the top of your head who wants to do this? It sounds like you didn’t have someone, oh, I know I’m going to go to X person or Y person, but you just did this in a systematic way. You just went about this sort of in a probability way. If you text 50 people, one of them might know.
And that worked out. So I just feel like this is so cool because an approach almost anyone can do and maybe it won’t work, but you can at least try this. This is something anyone can try and you don’t know. Now, tell us a little bit, Jesse, about the initial conversations with this partner. This is a tough thing. A lot of people are out there trying to form partnerships to raise money, and even if they have great deals and all the right credentials, you’re talking to somewhat of a stranger. So how did you build rapport with this person who you were going to ask for presumably a decent amount of money?Our initial conversations were pretty comfortable. We were talking about our goals, not just in real estate, but in life, what we consider a good investment, what we consider a bad investment, what we value in a work environment. But then as we got into our second conversation, it was more what are you most afraid of when it comes to partnerships? What would make you consider this to be a failure of a partnership?Good question.What happens if one of us dies?WhereIs the money coming from? Where’s the money coming from? How involved is your partner going to be? So just more difficult questions and you have to honestly just kind of get over it if get comfortable talking about stuff like that that helped us bake all the right things into our partnership agreement.Yeah, my first deal, I partnered with three other people and fortunately someone gave me the wise advice to hire a lawyer, spend the money upfront, and the lawyer walked me through all these questions that you would never think of yourself. And I knew these people decently well, but it still sort of just forced an intimacy almost that allows you to really assess the person as you’re talking through a little bit awkward things or sort of having to envision some worst case scenarios too. You sort of see how people react. Are they calm? Do they get nervous? Do they get agitated about these things? I found that process to be super helpful. So what was the first deal? You wound up hitting a grand slam on this first deal, it sounds like, but you said you went out of state too.Yeah, so first I was trying to make everything a grand slam in Massachusetts on market. Sounds tough. Yeah, I was really optimistic. But after about six months of making creative offers on market, I realized this just is not going to work. And I think a lot of people pivot too soon. They pivot just maybe when it doesn’t work after one day. But I really put in the reps. I was writing and signing offers every single week for six months. And the issue was I was trying to make all of these deals a home run, but there was 20 people in line behind me offering with traditional financing who were happy to just break even. So I was never going to get an offer accepted. And then we realized, okay, well we’re going for five units and up, so we’re going to have to have a property management agreement anyways to close. So does it really have to be nearby because the numbers in other parts of the country are so much better? So we looked into a couple different cities in the Midwest where other long distance investors often go, and we just had a conversation about how we feel about each of these cities. We landed on Chicago and we decided together to move forward in Chicago on a Friday, and we were under contract on Sunday night.Wow. Oh my God. That’s unbelievable.Yeah.Were there just an abundance of deals or did you get lucky with this one?Well, I will say I think when you are going long distance and you’re from an expensive market, the most picked over deals on LoopNet look amazing to me.Yes, it’s so true. It’s a hundred percent true. Yes.But I’m also not afraid of, I don’t even want to say low balling. I don’t think I’m that offensive with it, but I’m not afraid to offer less.And that worked in a dayPretty much. So I’ve gone on to do four deals around the same size. In Chicago, there are eight to 13 units and none of them we’ve paid asking price. We’ve gotten great seller credits on all of ’em. I think it’s a matter of getting something when it’s been on market for a while and really explaining the reasoning behind the price that you’re offering rather than just seeming you’re casting a wide net and low balling 25 people in one day.So you got to tell me about the details of this deal. How did you go from an on market deal to building a million dollars in equity?So we paid, I have the notes in front of me. I’m so excited about this deal. I try and replicate this deal with every other one.Yeah, IWould think so. So we closed August of 2023. It was listed for 1.08. We paid 1.06. We got a $45,000 credit. It appraised for 1.1 when we bought it, but today it’s worth just over 2 million.Oh my God.And really the value today is only about 75% of what it would be if everyone was paying market rent, because similarly to just everyone’s real estate investing journey in general, the finish line just keeps getting pushed out because market rents keep going up. So we’re always going to be chasing this true full potential of the building. But when we bought it, we were maybe cash flowing like $800 a month, but it was irrelevant. We were planning to reinvest any cashflow for a couple years anyways. But today at Cashflow is on paper around 5,000 a month. That’s still only 70% of what it could be cashflowing if everyone was at market rent. And we are still in a phase where we’re reinvesting, we’re turning over some units that haven’t been touched in a long time. But yeah, we’ve had that for just over two years and it’s come a really long way.Congratulations. I mean, that’s a career changing kind of deal.Thank you.Did you do a heavy value add to boost the equity or is it just rent growth?Mostly just rent growth. I mean, I usually target buildings that are nowhere near falling down. They’re at least 80% occupied. They’re fine. There’s just like a tired landlord situation is my favorite situation. There’s just a lot of deferred maintenance. Rents are really far behind. An up and coming neighborhood is great. I love when it would meet the 2% rule if the rents were where they were supposed to be. I like the projected rents or market rents to meet the 2% rule. That’s a good deal for me.And did you have to put a lot of money in to drive up the rents or was it just gradually working with the tenants and your property manager to move it?More so just gradually bringing the rents to where they should be. I think our initial renovation budget was something like 40, 45,000.Okay.That was just to be in our back pocket, just in case we expected some of the turnovers to be pretty heavy as they came. And then I believe in this time we’ve probably added another 20,000.I mean, compared to the purchase price though and the total value that you’re getting. Very good ROI on that additional spend for sure. So what was it like for you moving from investing in your own neighborhood to trusting a property manager to work with halfway across the country?Honestly, I highly prefer it because I feel like when it’s long distance, I’m thinking of it more like a business. I don’t know. It’s less stressful to me. I think obviously you do really have to have a management company that you love. So when we first got under contract on this one, I interviewed 30 different property management companies over the phone, and it ended up that I really loved the very first one that I talked to. So that’s who I still work with now and they’re amazing. And I actually finally just went out and met everyone in person and saw all the properties in person for the first time a few days ago.Oh wow. How did they stack up to your expectations?Oh my God, everything was great. Everything was exactly as expected, which I think is a testament to how well the management company communicates and how good of a system we’ve worked out.Well, congratulations again. I am with you a hundred percent. I don’t regret anything, but in retrospect, I invested in Denver for eight, 10 years and I moved to Europe. I was forced to start investing long distance. It was all long distance, kind of a similar idea to you. I was like, I might as well invest in the Midwest. The numbers are better. And I was like, man, I would’ve grown faster if I had just done this sooner. Not because of just the purchase prices are lower, but because my own hangups about, oh, if I buy another three unit, I’m going to have to manage three more units. Even if it’s in the back of your mind, kind of makes you go a little bit slower. Whereas if you do a long distance investing, it really is more of an operations in a math problem and it’s less emotional.AndI think it does have a lot of benefits, especially once you’ve sort of learned the industry and been hands-on enough how to vet a property manager, how to screen a deal. I think it could be a really beneficial thing. I know it sounds intimidating, but it’s not as bad as people think. I want to hear how you’ve scaled up from here. But we do got to take one more quick break. We’ll be right back. Welcome back to the BiggerPockets podcast here with investor Jesse Dillon. Jesse, incredible story so far. You bought this incredible deal in Chicago. You said you’ve been trying to replicate that one first grand slam deal. Have you been able to?I couldn’t for a while. So we closed on that deal summer 2023, and then I built out my process of how I was going to find my next partner. I had a list of 15 things that I was going to do daily, weekly, monthly, quarterly to get in front of the right person. And it was working. I was planting seeds, but nothing really panned out for a year and a half. But I kept plugging away at my 15 step process of how to find the right partner. And about a year ago now, so fall 2024, I went to one of the many wire retreats that I’ve gone to and it just totally reinvigorated me. And when I got home, all of a sudden, all these seeds that I had been planting that whole time all started to come together. So I had one partner reach out to me and say she was ready to go. She completed a refi that she was waiting on. And then in February we closed on an eight unit together. Also in Chicago, also value add. And right around the time that we closed on that, I had two other partnerships that came to the point of being ready to go, ready to make offers, create our entity, fund the account start to offer. So in those, I closed on a 13 unit in June and a 12 unit in July.Oh my God.Yeah. So very divinely. It ended up being exactly 50 units, the number that I had set out to. That’s amazing. Wow. And yeah, just in retrospect, the timing was perfect. Everything worked out exactly how and when it was supposed to. And I had said all along, this was my finish line, this was where I was going to stop buying and just let all of the value add properties, marinate for a couple years. Now that I’m here, I probably did take a break for a week, and then I was very long to tired. Now I just figure out. So then I was like, all right, I got to figure out what the next plan is. I feel like the portfolio I’ve built so far is very equity heavy, which is so great. And my 40-year-old self is going to be really thrilled about that. But today I was like, I need to balance it out with stuff that’s going to cash flow a little bit sooner. So my plans for this year are very different than what I’ve been doing so far.I want to just take a step back though, and just thank you for sharing some of the challenges that you went through, because again, these are things that everyone goes through. No one puts it on social media, but there are definitely times in any entrepreneurial journey where it sucks. It’s just nothing is working. It’s super frustrating. I don’t know if you feel this way, but I find it very lonely. There’s no one to talk to about it, and it can be hard. So I was just curious, how did you persevere through that? I think that’s a common challenge that folks in the BiggerPockets community do encounter, even though it’s not talked about so much.I think it helped that the people very close to me never had any doubt in their mind that I was going to make this happen and that it was going to work out for me. But it helped a lot to be more active in communities like the wire community that Amelia and Grace host that has actually been so pivotal. I think just being around other people at those retreats who are similar to me and doing what I want to be doing and making moves. Every time I’ve gone to a wire retreat, I’ve come home and something has shifted exponentially in my business. And then another thing is I don’t take advice from people who are not doing what I want to be doing. Everyone has a horror story about real estate, and unless you are Barbara Corcoran, I don’t hear it. I don’t care about the story’sA very high bar for what advice you’re willing to accept, but I appreciate that. So you were hitting on a lot of the deep secrets of real estate investors right now that it’s hard that people run out of money. And you touched on the moving the goalpost thing, which I think is another common challenge people face. I’ve been talking about this a lot recently on the show, but people always say, oh, don’t have lifestyle creep. But we all kind of get into this. To have a little bit of lifestyle creep isn’t part of the desire to sort of not just retire early, but to have the kind of lifestyle that you desire. I’m not saying be a tycoon, but live the life that you want to comfortably. So how is that evolving for you? Are you wanting to keep going past 50 because of money because you like doing this? Or what’s driving the next phase of your portfolio growth?Honestly, part of it is just for the love of the game. Even with all of the challenges, I do think it’s kind of addicting to keep going. But the bigger piece is, while all my value add multifamily ramps up, I want to be doing something in the meantime that will cashflow sooner because I do want to be location independent. I want to be able to take a few months off from the salon at aTime.So that’s the big motivator to keep going for me. Right now, I don’t foresee myself completely stepping away from the salon world, but I want to have that option. I actually feel like I’m the opposite of lifestyle creep because my ultimate vision of success is living in a camper. And I live in a beautiful home right now, but I want to be time independent, location independent, financially independent in my camper. So I actually want to simplify and downsize. So that’s kind of what I’m working towards.What will that look like, do you think, similar kinds of deals that you’ve been doing the last few years?Well, I’m transitioning, now, I’m going back to short-term rentals. So me and one or more of my partners are going to be doing a couple of vacation rentals within the next year. And I also am finally getting my real estate license over the winter.Nice.It’s been very daunting. I haven’t done any formal schooling in a while, so I’m a little nervous. But I’m going to do that because I plan on doing another house hack next summer. So I want to be able to offset my down payment. Nice. And additionally, my daughter turns 18 and graduates in the spring.Oh, cool.So I want to be able to help her with a house hack as well, and offset that down payment too. So those are my plans, congrat for the next 12 months. Thank you.Jesse, thank you so much. This has been a fascinating story. Congratulations on all your success. I think you have a really cool approach and perspective on real estate. Thank you for sharing it with us.Yeah, thank you so much for having me.And thank you all so much for listening to this episode of the BiggerPockets podcast. If you think I do that, a lot of people who are thinking about getting into real estate would benefit from hearing Jesse’s story, please share it with them. I’m sure they would appreciate hearing such a cool, relatable story. We’ll see you next time for another episode of the BiggerPockets podcast.