How Jessie Dillon Built 50 Units in 4 Years with Value-Add Multifamily & Partnerships

Jessie Dillon (00:00)

Yeah, so one of my first few deals was a single family home that I bought as a vacation rental. And my rookie mistakes with that deal were

I did not buy something that would at least break even as a long-term rental. In retrospect, I wish I did. And I also bought in a market that’s highly seasonal, which I don’t particularly love for vacation rentals. But that property was just a little too far from the winter activities. It did amazing in the summer, but it wasn’t enough to support it through the winter. So.

that property I held onto for a year and then I actually sold it creatively. So I sold it sub to hybrid seller financing. And that turned what would have been a break even deal into a $75,000 profit deal, holding it for one year. So yeah.

Michelle Kesil (02:27)

Hey everybody, welcome to the Investor Fuel Podcast. I’m your host, Michelle Kesil. And today I’m joined by someone that I’m looking forward to chatting with, Jessie Dillon, who’s been making serious moves as a buy and hold investor since 2022. So excited to have you on the show today, Jessie.

Jessie Dillon (02:45)

Yes, thank you so much for having me.

Michelle Kesil (02:47)

Absolutely, think our listeners are really going to take something away from how you’re structuring your operations and how you scaled to 50 units in under four years. So let’s dive in. First off, for those not familiar with you and your world yet, can you give the short version of what your main focus is?

Jessie Dillon (03:05)

Yeah, so I focus mostly on value add multifamily. I’m a long distance investor and I actually primarily now buy in partnerships. So I’m huge on partnering. I am pivoting a little bit right now, but everything I have focused on until now is value add multifamily.

Michelle Kesil (03:24)

Awesome, and what markets are you operating in?

Jessie Dillon (03:26)

I live in central Mass and I do own a couple of properties out here, but I mostly invest in Chicago.

Michelle Kesil (03:32)

So I got you into this.

Jessie Dillon (03:33)

So in 2021, I was feeling a little burnt out in my day job, which is owning and operating a salon. So I worked behind the chair with clients and I was just putting in a lot of hours. And I think having to step back during COVID when we closed for three months really made me realize how much I was working.

So first I went down the fire path through really aggressively investing in index funds. And I just knew that was still going to take too long. And I wanted to be work optional faster. And just one podcast led to the next. And I started hearing about real estate investing on all of these financial independence podcasts. And this was summer 2021. So that fall, I just dove into all the books and the podcasts and the coaching calls and boot camps.

And everything started to kind of sound the same around Thanksgiving. And that weekend is when I started making offers and got under contract on my first property that I then closed January of 22. So it was really born out of burnout and wanting a path to wealth building that was faster than index fund investing.

Michelle Kesil (04:43)

Awesome, I love that story. That’s so cool that you were able to get started and really pivot into a way that can give you success.

So I know that you mentioned that you scaled from zero to 50 units under four years. Can you expand and share how you were able to do that and what that journey looked like for you?

Jessie Dillon (05:04)

Yeah, so my first three deals were smaller properties, but in an expensive market. So this was 2022 and I used my own money to get into those. had put down 10%, 10 % and 8 % and

just using like different loan products. And even so I was tapped out after that. So I would have had the time and knowledge to keep buying faster than I had the time to build up more down payments, buying in an expensive area. And I had really done so much homework on real estate investing. So I felt pretty confident that after doing those first three deals, I was confident enough that I could use someone else’s money to keep buying. And

That’s when I kind of opened my mind to partnerships. I was resistant to them up until then, but I went to a conference and it really opened my mind to partnerships. And I realized I just needed to find the right one, the right person who really complimented me. And we each brought what the other person was lacking. And it just felt right. So I set out to find the right partner. I found my first one. And the following summer,

of 2023, we closed on a 13 unit together. And then, you know, I just kept the ball rolling. was looking for my next ideal capital partner. I was planting a lot of seeds and nothing actually worked out for like a year and a half. So I was putting in the work, I was doing the reps, but I didn’t buy anything in 2024. And then towards the end of 2024, though,

things started to come together, like the seeds that I had been planting to find these aligned partnerships started to come to fruition. And this year, in January or March, I closed on an eight unit with a partner. In June, I closed on a 13 unit with a partner. And in July, I closed on a 12 unit with a partner. So this year alone, I went from 17 to 50 units.

my net ownership percentage of all of these 50 units is just a little over half. But that once all of these properties really start functioning how they should, since their value added will take a couple years, that is enough to make me work optional.

Michelle Kesil (08:07)

Amazing. I love that. That’s such a cool way that you were able to scale so quickly. When it comes to your partnerships, like how did you find the right partner? Was it through networking or connections that you already had?

Jessie Dillon (08:14)

Thank you.

I found each partner in a different way. So my first partner I found from, I actually created a list of 50 people who I thought would maybe know someone who fit my ideal partner description, which I had to come up with first. And I just said, every day for 10 days, I’m going to text five of these people. So I reached out and just said something like, you know, I know we’re connected online.

I hope you’re doing well. If you have been following what I’m doing online, this is what I’m looking to do next. I’m looking for someone who XYZ, if this makes you think of anyone in your network, would you just share my information with them and they can reach out if they’re interested. And someone that I had texted was actually sitting at dinner with her friend who kind of fit my ideal partner description. So she set us up and that’s how I met my first partner.

My second partner we met because she attended a workshop that I hosted through a local chamber of commerce on how to buy your first rental property. My third partner we met because we’re in the same online community for female investors. And she also heard me on the podcast of the creators of that community. And my last partner I met because I actually used to work for his colleagues.

son. So if you can follow that one. And that just kind of shows the importance of telling everybody that you know what you’re doing, what you’re looking to do, and just keeping the conversations going.

Michelle Kesil (09:49)

Amazing! That’s so cool! I love that it worked out in such a flow for you that all those connections were able to find you.

Jessie Dillon (09:57)

Mm-hmm.

Michelle Kesil (10:34)

So what are some of the main keys that have allowed your business to run smoothly and successfully?

Jessie Dillon (10:42)

I think the biggest thing is just being super organized. like not only do I run my real estate business, but I also run my salon business still and work in it part-time. So between those two, there’s really not a lot of space for error.

⁓ so I use monday.com as a task tracking software. also have two virtual assistants. One is more like a high level executive assistant. so between the two of them, I can offload a lot of just the repetitive tasks or things that really don’t require my voice or my face. I think generally anything that you can record a loom video on telling someone else how to do it should be off of your plate as a

business owner, think you should really be doing the tasks that are, you know, bigger picture, higher level, that are really going to ultimately make you more money.

Michelle Kesil (11:33)

Yeah, that makes a lot of sense to offload those heavy tasks and create more space to do what you are passionate and good at for your business. think that team effort is so important.

So what are some of the things that you are focusing on solving or scaling to next in your business?

Jessie Dillon (11:53)

So I honestly have done what I set out to do with Value Add Multifamily. Like my goal from the beginning was 50 units with most of them being bought in these partnerships.

So it was kind of time to pivot this past summer. And one of my business partners and I, we were looking into doing self storage. We were offering on storage and it just really didn’t feel aligned. I think part of that was because it’s really hard to find a great deal unless you’re doing a lot of off-market lead generation, which I don’t do. I think there’s just so much competition in the storage space and there’s a lot of people who are happy to get a breakeven deal.

and we are not. So we’re considering pivoting again into short-term rentals, which I actually have experience operating short-term rentals. So that is one big opportunity that lies ahead. Another is I’m actually working on doing my first flip, which I think it’s so funny that I have not done one so far, but I’ve just been really laser focused on buying multifamily.

for the long term and now it’s time to kind of reel it back in and balance that out with more short-term projects. And I also plan on getting my real estate license this year because that will help me with the plans that I have for next year.

Michelle Kesil (13:06)

Amazing. I love that you’re laser focused on what’s next for you. What is the real estate license going to support you with?

Jessie Dillon (13:15)

So next summer I would like to get into a new house hack. So I’m a big advocate of house hacking. think everyone should be house hacking. I would like to do another one next summer. And if I have my real estate license and I’m my own buyer’s agent, I can offset my down payment. But also my daughter turns 18. So she would like to do a house hack. So same thing if I’m the buyer’s agent that will.

offset our family’s down payment. So I’m not sure that I see myself doing much beyond that with my real estate license, but you never know. I think after I put the time and effort into getting it, I might create some kind of system around just making referrals and getting some residual cash from that.

Michelle Kesil (13:58)

Amazing. That’s such a cool way to support yourself and yeah, get creative with ways that you can grow your investments and save some money.

Jessie Dillon (14:08)

Thank

Michelle Kesil (14:52)

So let me ask you this, every business owner has those moments where things get real, maybe a deal that goes sideways, or you have to pivot fast. Would you mind sharing one of those moments that you’ve experienced and how you overcame it?

Jessie Dillon (15:07)

Yeah, so one of my first few deals was a single family home that I bought as a vacation rental. And my rookie mistakes with that deal were

I did not buy something that would at least break even as a long-term rental. In retrospect, I wish I did. And I also bought in a market that’s highly seasonal, which I don’t particularly love for vacation rentals. But that property was just a little too far from the winter activities. It did amazing in the summer, but it wasn’t enough to support it through the winter. So.

that property I held onto for a year and then I actually sold it creatively. So I sold it sub to hybrid seller financing. And that turned what would have been a break even deal into a $75,000 profit deal, holding it for one year. So yeah.

I feel good about that. I I learned great lessons about short-term rentals and I took away some great experience and I did ultimately turn that profit, which is great. But if I hadn’t known about creative financing, I would have just sold it on market and it would have been a breakeven experience.

Michelle Kesil (16:18)

Yeah, absolutely, that makes a lot of sense. Thank you for sharing that. Yeah, I feel like these types of examples are what allow people to really get their mind into that long-term vision and keep moving forward.

Jessie Dillon (16:33)

Okay.

Michelle Kesil (16:35)

So when it comes to growing your business, whether that’s through networking or relationship building,

what are some things that have made the biggest difference for you?

Jessie Dillon (16:46)

I think what’s made the biggest difference for me is probably using social media to make sure everyone knows what I am doing and what I’m working on. And that’s not really limited to

you know, Instagram and Facebook, it’s also getting on podcasts like this and sharing my experience and being a part of online communities for real estate investors, providing value in there, connecting with people through those. I mentor in an online program called The Wire Community, Women Invest in Real Estate. I co-host the beginner cohort. So a lot of partnership and private lending opportunities have come from there.

⁓ So I think like, you know, if you’re someone who’s really shy about putting yourself out there in person and going to those in-person networking events, you can be just as successful networking online and just sharing at least a couple times a week about what’s going on in your real estate journey, even if you don’t think there’s that much going on yet.

Michelle Kesil (17:42)

Yeah, absolutely. That relationship building skill is so important in this phase, no matter if it’s online or in person.

Awesome. So if someone is maybe newer to investing and they’re wanting to get started, but aren’t sure what that path looks like, what are some of those tips that you have for beginners looking to get involved?

if someone is newer to real estate investing and they’re wanting to get started but aren’t sure what those first steps to that path looks like, what are some tips for people looking to get started on their journey?

Jessie Dillon (18:18)

I think my number one tip is always to only take advice from people who are doing what you want to be doing. Even if you’re not exactly sure what area of the real estate space you want to be in, I think it’s still, you know, you can still identify people who are in the space, who are at meetups or who you’re seeing in those groups online or who you’re finding on Instagram. You can still identify people who, you know, give you something to be envious of.

And you can reach out to those people and try and connect with them and try to offer value or pay for a consultant call with them. I would also say to at least do something every day that is helping you learn more about real estate. So maybe you’re meeting for coffee with someone. Maybe you’re going to a meetup, maybe you’re listening to a podcast or listening to an audio book.

I loved all of the bigger pockets books like on the BP bookstore online. So many of them have been pivotal for me. So I think do something every single day, check the box every day. If this is something you’re serious about and yeah, don’t be afraid to reach out to people and just ask for advice or input.

Michelle Kesil (19:34)

Absolutely, think that mentorship, support, educational platforms are so important for beginners to get their feet wet.

Jessie Dillon (19:44)

And there’s no shortage of free information online, but I do think that when you invest in education, like if you join a group or a community or a program online that is paid, or you pay to go to a conference or you pay for coaching calls, I think you are more likely to use that information, even though you could have learned the same thing for free online. I know not everyone has the resources to be paying for stuff like that, but if you do, and you can

Michelle Kesil (19:45)

Awesome.

Thank you.

Jessie Dillon (20:11)

push yourself to invest in it, I do think you’re more likely to take action.

Michelle Kesil (20:15)

Totally, yeah, putting some skin in the game definitely gets you more laser focused on that goal.

Jessie Dillon (20:21)

Mm-hmm.

Michelle Kesil (20:21)

Awesome. So before we wrap up here, if someone wants to reach out, connect, collaborate with you, where can people find you and connect with you?

Jessie Dillon (20:30)

I am mostly on Instagram, so I’m jessiedillon with an underscore at the end.

Michelle Kesil (20:34)

Perfect. Well, listen, I appreciate your time, your story, and your perspective. Thank you for being here.

Jessie Dillon (20:39)

Yeah, thank you so much for having me.

Michelle Kesil (20:41)

Of course. And for the listeners tuning in, if you’ve got value from this, make sure you’ve subscribed. We’ve got more conversations with operators just like Jessie who are building real businesses. We’ll see you on our next episode.