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

This 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 15 years now and I am the head of real estate investing here at BiggerPockets. Our guest on the show today is investor Jesse Dillon. Jesse lives in Massachusetts and had a hands on day job owning a small business in 2021 when 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 cash flow 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 gotta 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 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 because I, like everyone else, thought that, you know, 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 bigger pockets. So I just went crazy. Fall 2021, I did all the boot camps, I did all the books and the podcasts and the coaching calls, and I just totally became a student real estate. And that was for a couple months leading up to offering on my first property.

So after all the boot camps, 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 because 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, you know, having more than one unit, I just felt more diversified. Like 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 410, appraised for 420, but I got it for 357.

Wow.

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 like my first purchase ever. Like 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 yeah, 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 because 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 that 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. Like 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 cash flow. A true net profit of $500 per month per unit.

It'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 cash flow goal is 15,000amonth. So I know if I can buy properties that are going to cash flow 500amonth per unit if I'm buying them now in these 5050 partnerships, it's easy to back into how many units I need to buy. I do think unit count can be, you know, kind of arbitrary, but that makes it easy for me to know, you know, where the finish line is.

I, on this podcast, rail against unit count all the time. I think it's very silly because I know people who have 10 units who perform better than people of 80 units all the time. But what you're doing makes total sense. Like 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 such units?

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 in partnerships. So I kind of backed into, you know, if I build the rest of 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, 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 guest room.

Oh, cool. Wow. You're just 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. They understand how investors operate, and they've built a system that works for us. Quick approvals, flexible terms, and none of the endless paperwork that slows things down. Whether you're working on a flip, buying a rental, or tackling a big commercial project, they give you the speed and flexibility you need to make it happen. Great deals don't wait, and neither should you. Get your funding locked in by going to expresscapitalfinancing.com or click the link in the description. Trust me on this one, it'll save you a ton of headaches. Visit expresscapitalfinancing.com biggerpockets for more information. Want to invest in real estate but don't have the time or know the best local markets? Rent to Retirement has got you covered. Here's the deal. They've helped thousands of investors just like you find turnkey homes across the best US Markets. And best of all, they do all the heavy lifting for you. With over 255 star ratings on bigger pockets, Rent to Retirement experts help you build strategies to retire early through real estate. And right now, Rent to Retirement offers some amazing incentives on turnkey new construction properties. Just for example, you can get up to 30% off new build prices or you can get 0% down loan options or interest rates available as low as 3.99%. So don't miss out. These deals will not last. Text REI to 33777 or visit biggerpockets.com retirement to start investing in top cash flow markets today.

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Welcome Back to the BiggerPockets podcast. I'm here with investor Jesse Dillon talking about how she started close to home, bought three properties using a bunch of different strategies, using her own money, but then at a point realized she was tapped out on her own cash and looked to a new strategy. So Jesse, tell us a little bit about that transition. What was it like? How did you work through this challenge that every investor faces where they run out of capital to use as down payments?

Well, first of all, I didn't have anyone telling me that everyone faces this, so I felt like a huge failure. Like, I felt like I screwed up somewhere tragically along the way because like, everyone, everything I saw on Instagram was people scaling in a way that, like, didn't even make sense to me. And I'm like, how is everyone doing this? And no one's failing at anything. It seems like everything goes perfect.

Yes.

And then that year, so fall 2022, it was the first BPCON that I went to and I was sitting in Ashley and Tony's presentation about partnerships and I just had this like, aha moment where I was like, wow, like, I am. I've reached this threshold that actually I should be really proud to have reached. If it's this rite of passage for everybody and it just has to become a team sport and I don't have to be afraid of partnerships like I had been. I realized I just have to find the right partner. And the first piece of that was figuring out who the right partner is for me. So I worked out in my head like, you know, well, what do I bring to the table and what would this look like in a perfect situation? And I knew, you know, 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 VPCON that year, I made a list of like 50 people who I thought they would probably know someone who understands, 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, you know, the day to day work of real estate investing. So I made a 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 like a copy paste message. And it was something like, you know, I know we're connected online. So you've probably seen that I've been doing XYZ and real estate investing. This is what I'm looking to do next. If you happen to know someone who fits XYZ description, would you just send them my info and we can have a 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.

Yeah.

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 goal 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. Like we both felt like it was almost unfair to the other person and just like such a no brainer. So about nine months after that, we closed on a 13 unit long distance together. 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 Wire, that was a million dollar text, literally.

Right?

Like, that's unbelievable. 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, like, 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. Like, it sounds like you didn't have someone. You're like, 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. Right. Like if you text 50 people, one of them might know. And that worked out. So I just feel like this is so cool because it's a, it's 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, because 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, you know, 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?

That's a good question.

What happens if one of us dies?

Where is the money coming from?

Yeah, like, where's the money coming from? You know, how involved is your partner going to be? So just more difficult questions and you have to honestly just kind of get over it and like, 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 up front. And the lawyer walked me through all these questions that you would never think of yourself. And I knew these people decently well. But like, it's still sort of just forced an intimacy almost that allows you to really assess the person like as you're talking through like 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. Like 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 are 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, you know, how we feel about each of these cities. We landed on Chicago and we decided, 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're 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 100% true. Yeah.

But I'm also not afraid of, I don't even want to say lowballing because I don't think I'm that offensive with it, but I'm not afraid to offer less.

And that worked in a day?

Yeah, pretty much. We We've gotten. So I've gone on to do four deals around the same size in Chicago. They're eight to 13 units and none of them we've paid asking price. We've gotten great seller credits on all of them. I think it's a matter of getting something, you know, 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 like 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 $1 million in equity?

So we paid. I have the notes in front of me because I'm so like excited about this deal. I try and replicate this deal with every other one. 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, you know, everyone's real estate investing journey in general, the finish line just keeps getting pushed out because, you know, 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 because we were planning to reinvest any cash flow for a couple of years anyways. But today it cash flows on paper around 5,000amonth. That's still only 70% of what it could be cash flowing 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 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. Like 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 like the 2% rule, if the rents were where they were supposed to be, like I like the projected rents or market rents to meet the 2% rule. That's like 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.

Like 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 kind of to be like in our back pocket, just in case because 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, on the total value that you're getting very good ROI on that additional spend for sure.

Yeah.

So what was it like for you moving from investing in your own neighborhood to trusting a property manager to work with, you know, 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. Like everything was exactly as expected. Which I think is a testament to how well the management company communicates and like how good of a system we've worked out.

Well, congratulations again that I, I'm with you 100%. You know, I don't regret anything. But in retrospect, I invested in Denver for 8, 10 years self managed and I moved to Europe. I was forced to start investing long distance because 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 have grown faster if I had just done this sooner. Not because of just the purchase prices are lower, but because my own hang ups 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 and a math problem and it's less emotional. And I think it does have a lot of benefits, especially once you've sort of learned the industry and been hands on. You know 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 it is. 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. Do you want to invest in cash flowing rentals but don't have the time to manage the properties? Is your local market too competitive or expensive to invest in? Rent to Retirement offers new construction turnkey investment properties that you can buy with as little as 5% down and rates as low as 3.99%. Their team handles everything from financing, management, insurance and more so you can live where you want and invest in the markets that offer the best returns. Rent to Retirement has the best reputation in the industry with more five star reviews than any other company on the BiggerPockets website. To learn more, visit biggerpockets.com retirement or just text REI 233777 to start investing in the best markets today.

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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 up my process of how I was going to find my next partner. I had a list of like 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 like a year and a half. But you know, I kept plugging away at my 15 step process of like how to find the right partner, you know. 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, like 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 of. I set out to. I was trying to. That's amazing.

Wow.

And yeah, just in retrospect, like, 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 like a week. And then I was like, very long.

Yeah. 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, you know, 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, 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. Like there's no one to talk to about it and it can be hard. So I was just curious, like, how. How did you persevere through that? Because I think that's a common challenge that, 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 gonna work out for me. But it helped a lot to be more active in communities like the wire community that Amelia and Grace host. Like, that has actually been so pivotal. I think just being around other people at those retreats who are, you know, similar to me and doing what I want to be doing and making moves. Like, 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, like, I don't take advice from people who are not doing what I want to be doing because everyone has a horror story about real estate, and unless you're, you know, Barbara Corcoran, I don't care, and I don't care about the story.

Yeah, it's a very high bar for me for. For what. What advice you're willing to accept. But I appreciate that. So you were hitting on a lot of the. 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 goalposts thing, which I think is another common challenge people face. I been talking about this a lot recently on the show, but people always say, like, oh, don't have lifestyle creep, but, like, don't we all kind of get into this to have a little bit of lifestyle creep? Like. Like, isn't part of the desire to sort of not just retire early, but to, you know, have the kind of lifestyle that you desire? I'm not saying, like, be a tycoon, but, you know, live the life that you want to comfortably. So, like, how. How is that evolving for you? Like, are you wanting to keep going past 50 because of money because you like doing this, or what's driving sort of the next phase of your portfolio growth?

Honestly, part of it is just like, for the love of the game, like, there's. Even with all of the challeng, I do think it's kind of addicting to keep going. But the bigger piece is, you know, while all my value add multifamily ramps up, I want to be doing something in the meantime that will cash flow sooner because I do want to be location independent. I want to be able to take a few months off from the salon at a time.

Yeah.

So that's like 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. 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 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 because 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 payment and additionally my daughter turns 18 and graduates in the spring, 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 for like 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 Bigger Pockets podcast. If you think like 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 Bigger Pockets podcast.

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