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United States Real Estate Investor

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United States Real Estate Investor

The Bold FIRE-Movement Journey of Realization to True Financial Freedom with Jessie Dillon

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Jessie Dillon on The REI Agent
Jessie Dillon transformed business burnout into a journey toward FIRE and time freedom. In this REI Agent episode, learn the mindset, methods, and strategies behind her powerful story of reinvention and investing.
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Table of Contents
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Key Takeaways

  • Burnout can be a powerful catalyst for building a life of freedom through intentional investing.
  • Long-distance real estate investing works when you let go of control and build a solid team.
  • The FIRE movement empowers individuals to pursue time wealth, not just financial wealth.
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The REI Agent with Jessie Dillon

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Investor-friendly realtor Mattias Clymer
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Investor-friendly realtor Mattias Clymer
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How One Woman Used Real Estate to Escape Burnout and Build a Life She Loves

On this episode of The REI Agent Podcast, Mattias sits down with powerhouse investor and beauty industry entrepreneur Jessie Dillon, a woman who transformed exhaustion into empowerment.

What started as burnout in her successful permanent makeup business turned into a life-altering journey toward FIRE—Financial Independence, Retire Early.

Jessie’s story is one of raw honesty, grit, and relentless focus. It’s the kind of episode that leaves you inspired to audit your own life and start crafting a future on your terms.

When Burnout Becomes the Breaking Point

Jessie’s journey began not with real estate, but with exhaustion.

After building a booming beauty business, she realized she was completely burnt out, both physically and emotionally. She told Mattias:

“My business was me. I was my business. I feel like I was working twenty-four-seven.”

The nonstop hustle forced Jessie to confront a painful reality: success doesn’t always feel like freedom.

That’s when she stumbled upon a Facebook article about the FIRE movement. It clicked immediately.

“I read it and I actually messaged her on Instagram. She recommended some books and podcasts.”

That message sparked a fire that would change Jessie’s trajectory forever.

How Real Estate Became the Escape Route

While initially focusing on extreme savings and index funds, Jessie soon realized she couldn’t sustain the 70% savings rate needed to retire early through traditional methods alone.

That’s when real estate became the beacon.

“I was like, I’ve already figured out this business thing. I guarantee I can figure this out too.”

She closed on her first rental property in January 2022—and hasn’t looked back. From house hacks to multifamily deals to long-distance investing in Illinois, Jessie has built a portfolio with one goal in mind: becoming work optional.

Her formula?

Strategic partnerships, value-add deals, and laser focus.

“You ultimately get paid to be on this emotional roller coaster.”

Letting Go of Control and Building a Team

One of Jessie’s biggest mental shifts came when she realized she didn’t want to manage everything herself.

“Giving myself permission to hire it out just because I don’t want to do that was huge.”

Even local properties are now under professional management, allowing Jessie to stay emotionally balanced and focused on scaling.

Her philosophy is simple: treat every property like a business, and make decisions that support the life you want, not just the income you earn.

The Freedom to Explore New Frontiers

Jessie hasn’t stopped with rentals. She recently completed a self-storage investing course and has her eyes set on new asset classes for the future.

“I didn’t do it immediately because value-add multifamily is just my comfort area. But I’m looking forward to doing that.”

It’s this blend of discipline and curiosity that makes Jessie’s story so powerful.

She’s not just chasing numbers—she’s building a lifestyle.

The Power of Partnership, Purpose, and Perspective

Throughout the episode, Jessie and Mattias dive deep into the power of surrounding yourself with the right people, whether it’s a CPA, attorney, or a trusted investing partner.

“Only take advice from people who are doing exactly what you want to be doing.”

Jessie’s favorite book, The Millionaire Next Door, shaped her perspective on wealth. Not flashy. Not loud. But intentional, efficient, and strategic.

“I’m so rich with time now.”

She’s even passing the FIRE torch to her daughter, who has committed to investing half of her income in pursuit of retiring at 38.

That’s not just legacy—it’s leadership.

Build a Life You Don’t Need a Vacation From

Jessie Dillon’s story isn’t just about real estate. It’s about self-awareness, courage, and rewriting the script.

Whether you’re a burned-out entrepreneur or an aspiring investor wondering if you have what it takes, this episode reminds you:

“Pick a strategy and laser focus on it. They all work.”

Jessie didn’t just build a portfolio. She built a purpose. And it all started with asking: “Is this the life I want?”

If the answer for you is “not yet,” maybe this episode is your wake-up call.

Because real estate is more than investing—it’s your vehicle to live boldly, fulfilled, and free.

Are you ready to start driving?

Stay tuned for more inspiring stories on The REI Agent podcast, your go-to source for insights, inspiration, and strategies from top agents and investors who are living their best lives through real estate.

For more content and episodes, visit reiagent.com.

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Create healing and connection within yourself, your family, and your community.
Ivy & Sage Therapy - Create healing and connection within yourself, your family, and your community.
Create healing and connection within yourself, your family, and your community.
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Contact Jessie Dillon

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Transcript

[Mattias] Welcome to the REI Agent, a holistic approach to life through real estate.
[Mattias] I’m Mattias, an agent and investor.
[Erica] And I’m Erica, a licensed therapist.
[Mattias] Join us as we interview guests that also strive to live bold and fulfilled lives through business and real estate investing.
[Erica] Tune in every week for interviews with real estate agents and investors.
[Mattias] Ready to level up?
[Erica] Let’s do it.
[Mattias] Welcome back to the REI agent.
[Mattias] Your host here, Mattias.
[Mattias] Erica is enrolling our male child into preschool, which is crazy.
[Mattias] Yeah.
[Mattias] Our kids are growing up.
[Mattias] That daughter gave me this beautiful mug.
[Mattias] It’s rainbow colored.
[Mattias] I don’t know if you can see it.
[Mattias] And it says low key thriving on it.
[Mattias] And I don’t know if she read that, but that is just the sweetest mug ever.
[Mattias] I hope this thing never breaks because I love it.
[Mattias] Today, we have, Jesse Dillon on the podcast.
[Mattias] She is a a business owner that wanted got really into the fire community and, just went after rentals as a as a route to, yeah, becoming financial financially independent.
[Mattias] So FIRE, if you’re not familiar with it, is financially independent, retire early.
[Mattias] And I’ve been I’ve I’ve read different blogs throughout the years and been kind of part of those kind of communities, that kind of mindset.
[Mattias] And I, you know, part of me, enjoys enjoying life, and I think living as frugally as possible, isn’t always the way I want to live.
[Mattias] I think there’s a bit of a balance there.
[Mattias] And I also am like a a busy person, so I like to get after it a little bit.
[Mattias] And I think, you know, enjoying some of the fruits of of what, you know, the business that I’ve created, is okay.
[Mattias] But, you know, living that balanced life, is certainly good.
[Mattias] But what I really wanted to talk about with that is just kind of having this intentionality with what you put into your brain makes such a big difference as to how you see the world and how, you you behave ultimately.
[Mattias] You know, when we were in the debt payoff phase, my wife and I, we, you know, I would listen to Dave Ramsey, you know, a lot.
[Mattias] And it was just to have that community, because we we kind of got ostracized a little bit from some of Erica’s friends.
[Mattias] And I couldn’t see many of my friends as much as I like to.
[Mattias] You know, whenever they were wanting to go out, we just didn’t for the most part.
[Mattias] And or we would be, like, trying to do things that would be, you know, a lot cheaper since we were just so focused on that debt payoff.
[Mattias] And I just don’t know if that would have been possible, if we didn’t have that kinda, like, constant input from, from the podcast, Dave Ramsey podcast.
[Mattias] And and so I think that’s that’s just kind of, you call it brainwashing if you want.
[Mattias] And I’ve mentioned before on the show that, you know, I’ve kind of you know, I’m not a huge Dave Ramsey fan necessarily.
[Mattias] I think it played a really good key role in our life, so I’m not a hater.
[Mattias] But I certainly I’m not subscribed to his plan or his baby steps at this time.
[Mattias] I’m I’m trying to leverage real estate as much as I can.
[Mattias] But all that to say is, you know, I just think it’s it’s really important to to just be intentional about how you are filling your brain with with things.
[Mattias] And and if you are, you know, constantly watching, like, you know, the, I don’t know, celebrities or, like, the the Real Housewives.
[Mattias] I actually never seen that show.
[Mattias] I don’t even know what it’s about.
[Mattias] But, like, you know, you’re if you’re if you’re, like, having this glamorous, inundation of glamorous living in your in your brain, that’s what that’s what you’re gonna want.
[Mattias] And you’re gonna have your lifestyle creep up.
[Mattias] And if if, you know, wanting to become a real estate agent is because you are wanting to live a glamorous life, and all you want is the fancy things and to show up, to a a listing appointment in a Porsche and be, you know, wearing the the a fancy suit, with Rolex watches or whatever.
[Mattias] You can do that kind of stuff too, but, you know, that’s just gonna make your lifestyle a lot more expensive.
[Mattias] And if you gotta just think through, is that what you want over having more freedom of time, etcetera?
[Mattias] So, yeah, just being intentional about what you put in your brain, I think, is is just really, really important.
[Mattias] And, surrounding yourself with the community of people that, are like minded, that are where you wanna be, I think is also important for that.
[Mattias] So you can do listen to podcasts.
[Mattias] You can you can read books, that will help you get there.
[Mattias] And just, you know, again, having those friends that are, you know, kind of on the same journey, having maybe a few that are far ahead of you, and and where you wanna be.
[Mattias] I think those are all great ways of kinda just keeping yourself in in the right path.
[Mattias] And, you know, one of the things that we just talk about all the time is, you know, trying to live intentionally.
[Mattias] And if you don’t, you know, life will just happen to you.
[Mattias] So pick up a book, find a new podcast that, fits kind of the life that you wanna be living, that you feel like you should be living, and just start brainwashing yourself.
[Mattias] Use it as a trick.
[Mattias] You know?
[Mattias] Brainwash yourself for good for the good.
[Mattias] Anyway, without further ado, today on the show, we have Jessie Dillon.
[Mattias] She’s coming out of Massachusetts.
[Mattias] And like I said, she’s, into the fire movement and wanting to, retire early, through real estate mainly as her, vehicle of choice.
[Mattias] So without further ado, here’s Jesse.
[Mattias] Welcome back to the REI Agent podcast.
[Mattias] I’m here with Jesse Dillon.
[Mattias] Jesse, thanks so much for joining us.
[Jessie Dillon] Hey.
[Jessie Dillon] Thank you for having me.
[Mattias] Jesse, you are in the Massachusetts area.
[Mattias] You’re, an investor and a business owner.
[Mattias] Can you tell us a little bit about your story and how you got into real estate investing?
[Jessie Dillon] Yeah.
[Jessie Dillon] Of course.
[Jessie Dillon] So I’ve always been in the beauty industry since, like, 2011.
[Jessie Dillon] And in 2017, I went off on my own, started my own business.
[Jessie Dillon] And, right away, I fell in love with business and social media marketing, and my business really did take off right away.
[Jessie Dillon] It’s a small permanent makeup studio, so we tattoo brows, lips, and eyeliner and do a couple accessory services.
[Jessie Dillon] But it took off really, really well, a little too well.
[Jessie Dillon] And 2020 came, and I realized just how burnt out I was getting.
[Jessie Dillon] I think a lot of small business owners could relate.
[Jessie Dillon] My business was me.
[Jessie Dillon] I was my business.
[Jessie Dillon] I feel like I was working twenty four seven.
[Jessie Dillon] I could never stop thinking about it, and it also really was taking a toll on my body physically.
[Jessie Dillon] Mhmm.
[Jessie Dillon] It’s a lot of repetitive movements and being hunched over.
[Jessie Dillon] So I started looking into this whole fire thing and just I think it was a Facebook clickbait article where I first heard that term.
[Jessie Dillon] And it was about a girl in her late twenties who was going to be retiring by the time she was 30.
[Jessie Dillon] And I was like, I have to figure out whatever she’s doing.
[Jessie Dillon] So I read it and I actually messaged her on Instagram, and we talked a bit.
[Jessie Dillon] And she recommended some books and podcasts.
[Jessie Dillon] And first, I went hard with investing the highest percentage of my income I could in index funds.
[Jessie Dillon] And I was fortunate to be able to achieve a 70% savings rate, but I realized I was gonna have to do this for eleven years to actually retire that way, and I just knew I couldn’t keep that pace up for that long.
[Jessie Dillon] So I continued diving into all these fire podcasts, and there was a real estate investor on one of them.
[Jessie Dillon] And he was saying, you know, it’s really more doable to retire in a couple years if you really play it right with real estate investing.
[Jessie Dillon] I’m not a % bought into that idea now that I’m, you know, down this path, but that sounded a lot better to me.
[Jessie Dillon] So I was like, I’ve already figured out this business thing.
[Jessie Dillon] I guarantee I can figure this out too.
[Jessie Dillon] And this was fall two thousand twenty one.
[Mattias] Okay.
[Jessie Dillon] I just started listening to every single podcast, reading all the books.
[Jessie Dillon] All day while I was with my clients at the studio, I was listening to a real estate podcast, so my clients are kinda learning alongside me.
[Jessie Dillon] And, the following January 2022 is when I closed on my first rental.
[Jessie Dillon] So for me, real estate is an avenue to eventually become work optional in my salon, which I foresee being maybe a year and a half away now.
[Mattias] Okay.
[Mattias] Wow.
[Mattias] That’s amazing.
[Mattias] And I guess one of the questions I have for you right off the bat is, did did that new goal, that new that new target make the grind less bad?
[Mattias] Like, it had a had a more of a purpose or you had, like, you know, okay.
[Mattias] I’m gonna do this grind in the in the beauty salon.
[Mattias] Even though I was burnout, now I have, like, a renewed sense of purpose.
[Mattias] Did you feel that at all?
[Jessie Dillon] I think it was more so almost like a light at the end of the tunnel that made it more tolerable.
[Jessie Dillon] Like, in the beauty industry, no one has a retirement plan.
[Jessie Dillon] No one has a four zero one k.
[Jessie Dillon] Like, it’s very, very rare to have a job within the beauty world where you have that, and no one’s really talking about it or teaching about it either.
[Jessie Dillon] So this kind of no end in sight.
[Jessie Dillon] And I do really, really enjoy my work in the beauty industry.
[Jessie Dillon] Like, I don’t want to come off as if I don’t enjoy what I do, but I do also really value the concept of working just because you want to and not because you physically have to to pay your bills, and that’s really what I’m chasing.
[Jessie Dillon] I probably honestly will continue doing what I do in the beauty world, but just on a, you know, like, less frequent basis.
[Mattias] Sure.
[Mattias] No.
[Mattias] I think, I mean, that’s very common, I think, with, like, you know, small businesses in general.
[Mattias] You know, there’s, in the in the real estate sales world, there’s often the, like, you know, the people that just simply can’t retire.
[Mattias] They’re still, showing houses into their eighties or whatever and, honestly, are just working until they die.
[Mattias] And it’s some of them just, you know, love it and wanna keep going, and others, know, just had didn’t plan maybe the best and and, are are just kinda stuck having to keep the bills going.
[Mattias] One of the things we, you know, talk about as a lofty goal is to be, like, a % passive.
[Mattias] Sounds like that’s what you’re aiming for, so that you can, you know, build up your rental portfolio as you build up your real estate sales business or whatever other what other what other business you’re in.
[Mattias] And, yeah, just trying to get all your bills covered with a passive income and so you can then choose, you know, how to increase your lifestyle at that point because that’s a big factor.
[Mattias] Right?
[Mattias] Obviously, if you’re, getting new cash flow and you’re spending it right away with a new lease or or whatever, it’s just not really gonna replace your, needed income.
[Mattias] But, yeah, that % goal, it sounds like is you said a year and a half away already.
[Jessie Dillon] Yeah.
[Jessie Dillon] I think I’m about a year and a half away.
[Jessie Dillon] Amazing.
[Jessie Dillon] Right now, I’m closing on two deals that, you know, so long as these make it to the finish line, which I think commercial size multifamily has been kinda difficult to close for everyone lately.
[Jessie Dillon] So long as these two make it to the finish line, that will actually, in theory, complete my portfolio.
[Jessie Dillon] It’ll get me to where I have been wanting to go this whole time.
[Jessie Dillon] And since I really only do value add multifamily, you know, it then takes a little bit of time to ramp up and get to where I want it to be as far as cash flow goes, but that’s why I say about a year and a half out even if I was to close on these two next month.
[Mattias] Well, let’s let’s dive into that a little bit.
[Mattias] So was that the first deal that you did was a multifamily value add?
[Jessie Dillon] It was a two unit.
[Jessie Dillon] It was not value add.
[Jessie Dillon] It actually was I don’t wanna say turnkey.
[Jessie Dillon] So it was two units.
[Jessie Dillon] The unit that was owner occupied was in perfect condition.
[Jessie Dillon] The house was really, really well kept, and then there was, an addition built onto it that was a two level, two bedroom with a bonus room, but the tenant in there had been there for, like, something like thirty years.
[Jessie Dillon] So it hadn’t been touched and needed a lot of love when they moved out, but I do still own that property today.
[Mattias] Yeah.
[Mattias] I was gonna say if you jumped if you jumped fully into, like, a, like, your first deal was, like, a a 30 plex or something.
[Mattias] I was like, what’s
[Jessie Dillon] it was.
[Mattias] You what what podcast did you did you listen to?
[Mattias] Because that’s impressive.
[Mattias] So what have you bought since then?
[Mattias] Did you did you go into bigger, multifamily from there?
[Mattias] Or
[Jessie Dillon] So that first year, I bought the two unit, and then a few months later, I really wanted to try my hand at short term rentals because, you know, coming from beauty, customer service is so huge for me.
[Jessie Dillon] And, I saw how that was gonna translate to being a Airbnb host.
[Jessie Dillon] Sure.
[Jessie Dillon] So I bought a single family home up in New Hampshire.
[Jessie Dillon] I have actually since sold that creatively.
[Jessie Dillon] And then summer twenty twenty two, I bought my two family house hack, and then I also midterm rent my guest room in that property.
[Jessie Dillon] I’m sitting in that property right now.
[Jessie Dillon] And then I had didn’t close on anything for a year, and I sort of felt like I had done something wrong because I was tapped out of down payments.
[Jessie Dillon] And I could I had the time and knowledge to buy faster than I could build up those down payments, especially, you know, I’m in a high, a high ticket area, like, buying in Mass, New Hampshire.
[Jessie Dillon] So that’s when I kind of opened my mind to partnerships.
[Jessie Dillon] And almost a year after I opened my mind to partnerships, which it was actually BPcon that year that made me reconsider partnering.
[Jessie Dillon] I closed on a 13 unit value add multifamily in Illinois with a partner.
[Jessie Dillon] Since then, a few months ago, I closed on another eight unit value add multifamily out there, and the two deals that I’m under contract on right now are also with partners, a 12 unit and a 13 unit also in Illinois.
[Mattias] Okay.
[Mattias] Now how was the Illinois purchases based on the partner you found, or was that based on the market, that you, like, you did research market research and found that that was the best market to be in?
[Jessie Dillon] Market research.
[Jessie Dillon] So, my first partner and I, we were originally looking for something local, but the deals that we were looking at with the amount of capital that we had to play with, nothing was penciling out unless we were going to get it creatively.
[Jessie Dillon] But we really didn’t want to spend the time that it might take to try to find something off market where I feel like you’re more likely to get a creative offer accepted.
[Jessie Dillon] And I was making these creative offers on on market deals anyways, but there was 10 people in line behind me offering with traditional financing who were happy to just get a base hit while I was trying to make everything a home run.
[Jessie Dillon] So that that went on for about six months, and then we decided together, you know, clearly, that is not working.
[Jessie Dillon] But if we’re doing deals around this size, we’re going to have to use a property management company anyways.
[Jessie Dillon] Like, the lender will require it.
[Jessie Dillon] So is there really a purpose in staying local if we could find something that’s just a better ROI long distance?
[Jessie Dillon] And I’m happy that I have the flexibility to travel a lot.
[Jessie Dillon] And my partner, she actually also visited Chicago a lot for work, and that was one of the cities that we had started looking into.
[Jessie Dillon] It seems like just basically the farther away from the coast you get, the more the numbers work as a very, very broad rule of thumb.
[Jessie Dillon] But the more we looked into it, we loved Chicago, and I think a lot of long distance investors would not pick Illinois because it is a tenant friendly state and that comes with challenges.
[Jessie Dillon] But we were gonna buy in MAS anyways, which also is.
[Jessie Dillon] So that’s kind of the lens that I’m used to operating through anyways.
[Mattias] Okay.
[Mattias] Yeah.
[Mattias] It can be really hard if you are in an area that is, just, you know, an appreciation heavy market.
[Mattias] That’s where we are as well.
[Mattias] We’re we’re Virginia, so we’re also, East Coast.
[Mattias] I think there’s just people that, you know, they’re maybe they’re ten thirty wanting, money into something else, and they’re just happy to park it.
[Mattias] And it’s just like, this doesn’t pencil out.
[Mattias] Like, how is the the cap rates worse than the interest rate that we’re paying?
[Mattias] I guess this isn’t gonna
[Jessie Dillon] Mhmm.
[Mattias] This isn’t gonna work.
[Mattias] So, yeah, that that’s awesome.
[Mattias] I mean, did did it did it take, was it nerve wracking at all to start going into a a market that you weren’t as familiar with, that you maybe weren’t able to just drive by the property you’re looking to buy?
[Mattias] Did did, you know, investing in a in a different market, did that pose any kind of mental challenge that you had to overcome?
[Jessie Dillon] Not really, honestly.
[Jessie Dillon] But I hear so many people say, you know, I would never buy an investment property that I can’t drive by on a Saturday.
[Jessie Dillon] And it’s interesting to play that through in your mind.
[Jessie Dillon] Like, well, why do you need to drive by it?
[Jessie Dillon] Does it matter if you drive by it or if someone else drives drives by and sends you a video?
[Jessie Dillon] And I think it’s just you you know, you don’t wanna, like, let go of control of your investment.
[Jessie Dillon] But, I mean, with business in general, I have learned to delegate and let go of control a bit and understand that if I wanna save my time doing something, I have to be okay with someone else doing it at, like, maybe 90%, like, accuracy versus me having to do it the exact way that I would wanna do it.
[Jessie Dillon] So I feel like coming from an entrepreneurial background really helped me be okay with investing long distance.
[Mattias] Yeah.
[Mattias] Yeah.
[Mattias] That makes sense.
[Mattias] And and to your point, I mean, like, if it’s kinda forces your hand to get the the professionals in in place, you said you might have needed it anyway with a loan, but I think that’s another challenge some people might have is that they they feel like they’re gonna do a better job, running it out themselves and they won’t have that control.
[Mattias] And, you know, when you think about it, can kinda comparing it to, like, stocks, if you will.
[Mattias] Like, I mean, that’s one of the benefits of real estate, that can be an argument can be made for is that you, yeah, you can you can go see it.
[Mattias] You can go, like, you know, feel it.
[Mattias] You you know the market.
[Mattias] You you have much more understanding of the actual fit product that you have, the business you have, as opposed to if you invest in the index 500, you don’t know crap probably about what you’re invested in really other than it historically has done well.
[Mattias] So so, you know, in that sense, you know, I can see why some people have a little bit, you know, more comfort with, having something around them.
[Mattias] But, to your point, like, if if you are chasing freedom, you know, delegating that stuff out, and and growing in that way so you can get the the numbers to work better, in a in a better market for rentals makes a ton of sense.
[Jessie Dillon] Mhmm.
[Jessie Dillon] And I will also say, you know, even if you do have all the right people in place and you’re delegating and you have a property management company, you do still have to be the asset manager.
[Jessie Dillon] You can’t be completely hands off and never think about it or worry about it or ask about it at that point.
[Jessie Dillon] I have heard of a lot of people having a really bad experience in real estate investing because they ultimately expected their property manager to care about the performance as much as they do.
[Jessie Dillon] And you can’t really completely take your hand off the pulse.
[Jessie Dillon] You know?
[Jessie Dillon] Like, you still have to be overseeing and tapped into, like, what’s going on.
[Mattias] I mean, can you describe that a little bit, in more detail?
[Mattias] Are you looking at, like, you know, comparable property rents?
[Mattias] Like, what are what how do you do that to kind of help make sure it performs well?
[Jessie Dillon] Yeah.
[Jessie Dillon] So for example, like, with my properties in Chicago, once everything is once the dust kind of settles after closing, I’ll go to monthly check ins.
[Jessie Dillon] But my property manager has a really good pulse on, like, what I want to be involved in or included in.
[Jessie Dillon] So we’ll often end up talking a couple times in between those check ins.
[Jessie Dillon] But every month, I’ll send an email kind of, like, touching base on different things that we were talking about the previous month.
[Jessie Dillon] So what’s going on with lease renewals?
[Jessie Dillon] Like, for each one, what are we asking for?
[Jessie Dillon] Did they sign yet?
[Jessie Dillon] What are the what are the comps that we were basing that on for vacant units?
[Jessie Dillon] Where are they at, for certain repairs or maintenance or CapEx items that we kind of had on the back burner, like, where are we at with getting those done?
[Jessie Dillon] They helped me along with appealing the new assessed value recently.
[Jessie Dillon] So I’ll touch base every month, and I have a pretty good pulse of what’s going on in these buildings.
[Mattias] Sure.
[Mattias] No.
[Mattias] That makes sense.
[Mattias] Do you have it set up so that that if there’s a maintenance item, below a certain dollar amount that they’ll just take care of it, that kind of thing as well?
[Mattias] Or
[Jessie Dillon] Mhmm.
[Jessie Dillon] Yep.
[Jessie Dillon] Absolutely.
[Jessie Dillon] And then they also loop me in on anything bigger.
[Jessie Dillon] So for example, there was, a toilet had leaked and it caused, like, a, a lot of water damage in the unit below it.
[Jessie Dillon] Mhmm.
[Jessie Dillon] And there was, like, a 4AM emergency call about it.
[Jessie Dillon] So once everything was completely taken care of and resolved and fixed, they forwarded me the emergency call email and just let me know what happened, how they fixed it, and that it’s all good.
[Mattias] Okay.
[Mattias] That’s nice.
[Mattias] I was, you know, recently camping last year, and I didn’t when I went camping, I didn’t know if I would had service or not.
[Mattias] I did.
[Mattias] But I got, like, three calls from a tenant at at, like, 4AM in the morning.
[Mattias] Like, why why are you bothering me?
[Mattias] And it was a hot water heater had leaked, above and and was pouring water down, in his unit.
[Mattias] So it was good he called me, but it could have been nicer if that was the property manager handling that Mhmm.
[Mattias] Well, I’m keeping.
[Jessie Dillon] Yeah.
[Jessie Dillon] And, honestly, I worry about my long distance properties less than I worry about my local properties because I’m not a professional property manager.
[Jessie Dillon] And now I actually did hire out management for even my local properties because that just is not a task that I enjoy doing, and I don’t picture that to be part of my ultimate goal where I’m still the person taking calls.
[Jessie Dillon] And I did have to kind of get over mental blocks around that, like hiring property management for local properties.
[Jessie Dillon] Like, I could easily be doing that, but I just don’t want to.
[Jessie Dillon] And giving myself permission to hire it out just because I don’t want to do that was huge.
[Jessie Dillon] I did that this past December, and I joked that it was, like, my best Christmas gift to myself to just take that off my plate.
[Jessie Dillon] Because I get really anxious about, like, emergency issues and, Yeah.
[Jessie Dillon] You know, getting calls at all hours and stuff.
[Jessie Dillon] Like, I actually feel too emotionally up and down about properties that are local to me and properties that are long distance.
[Jessie Dillon] I really see them more as, like, a business.
[Jessie Dillon] So I just think about it differently, and I I enjoy how I think about the long distance properties a lot more.
[Mattias] I mean, that’s what it is.
[Mattias] They they are their businesses, and each each property you consider a a different business that you own, and I think that’s a really good lens to have.
[Mattias] And at the end of the day, again, if you are if your goal is to free up your time, and to to have more freedom, like, learning to to pass on the buck.
[Mattias] I I’m kinda talking to myself right now.
[Mattias] I’m not I
[Jessie Dillon] haven’t done
[Mattias] it yet.
[Mattias] I am a real estate agent, so, like, I kind of am on call anyway all the time.
[Mattias] So it hasn’t been too different, but it is a different type of and there’s liability involved too, especially as a licensee.
[Mattias] Like, you, you know, if somebody were to find you liable for, you know, fair housing that could that a violation there that you could, you know, lose your license and and that would impact your your whole livelihood.
[Mattias] So there’s there’s definitely a reason to and that’s probably honestly the biggest reason for me to get it off my plate would be just the liability end, because, you know, if I lose my license, that’s, that’s a big deal.
[Jessie Dillon] Yeah.
[Jessie Dillon] Definitely.
[Mattias] Have you had, the have you ever have you had, like, any, like, falls or accidents in your property too?
[Mattias] That’s another thing that just came to mind with liability is I had somebody slip on some ice, this past year, this past winter.
[Mattias] And, you know, again, another headache that disrupted my day that I, you know, would have need to have if if I had that, you know, property managed?
[Jessie Dillon] I have not had that.
[Jessie Dillon] The only thing that comes to mind, which I feel like a lot of investors probably would also be as scared as I was when this happened.
[Jessie Dillon] I did have a tenant who had a couple young kids, and, she had told me once that one of her kids tested positive for lead.
[Jessie Dillon] Wow.
[Jessie Dillon] And, yeah, and the unit was certified lead compliant.
[Jessie Dillon] In mass, if there’s a child living in the unit under a certain age, it has to be, and it it was.
[Jessie Dillon] So but still, I was immediately panicked.
[Jessie Dillon] And I may be panicked about it more than I had to, and that’s just an example of why, like, maybe I’m not the best property manager because I just, you know, go straight to panicking about things like this.
[Jessie Dillon] But my first call was the attorney that I used to close on that property because he’s been such an amazing resource for me.
[Jessie Dillon] Like, it’s so rare to find an attorney who, you know, when I have a quick question, I can text him.
[Jessie Dillon] I can email him.
[Jessie Dillon] I can call him, and he’ll get on the phone and explain the answer to me for twenty minutes, and I now get a bill afterwards.
[Jessie Dillon] But I refer a lot of business to him, and I always go to him for my local transactions.
[Jessie Dillon] And, you know, he explained to me how all of that works, where I can learn more about it on mass.gov.
[Jessie Dillon] I actually ended up getting on a call too with a woman who works for the state of mass who that’s all she handles, and I learned so much on that call.
[Jessie Dillon] I wrote a whole note in my phone about it, and I regularly share that with other investors.
[Jessie Dillon] And, you know, it ended up being completely unrelated to the house, but, it was a great learning experience.
[Mattias] Yeah.
[Mattias] Yeah.
[Mattias] And I think it’s just different when it’s your property, right, versus, like so I think, like, you know, problems can cause you, you know, headaches and anxiety and and all that stuff.
[Mattias] If you’re a property management manager, you probably get a little bit numb to to dealing with these things, but it’s just different too when it’s not yours.
[Mattias] And it’s it’s kind of like you’re you’re helping people through it.
[Mattias] It’s just a little bit more removed.
[Mattias] So, yeah, there’s there’s definitely benefits to that.
[Jessie Dillon] Mhmm.
[Mattias] When you, as you go forward, once you hit that, you know, %, do you think you’ll continue to invest, in real estate?
[Mattias] Or you do you think you’re just gonna retire on a beach and drink, mojitos all day?
[Jessie Dillon] I’ve been thinking about that a lot lately because it feels like something that’s getting closer.
[Jessie Dillon] And I do think that, you know, regardless of how these two deals in progress go, I would be open to doing another deal in the future with an existing partnership.
[Jessie Dillon] I have four partners, and I’d be totally happy to do another deal with someone I’m already established with.
[Jessie Dillon] And then also I’d like to do another house hack probably next year.
[Jessie Dillon] I don’t really see myself wanting to completely stop trying with real estate because I actually do enjoy it.
[Jessie Dillon] And I think once I’m past my finish line, it it’s gonna become even more enjoyable because I won’t feel like I’m chasing after something.
[Jessie Dillon] I’ll feel like I’m doing it just because I I love the game of it.
[Jessie Dillon] Like, it’s like fitting these puzzle pieces together.
[Jessie Dillon] You know what I mean?
[Jessie Dillon] Like, I I do really like it, and I have this skill set with, like, finding and analyzing deals and then operating these deals.
[Jessie Dillon] So, Yeah.
[Jessie Dillon] I think I’ll probably still be open to it, but I won’t be chasing after new deals, new partnerships.
[Jessie Dillon] You know?
[Jessie Dillon] Similarly to with permanent makeup, like, I’ll probably continue doing it, but it’ll most likely be more of my returning clients.
[Jessie Dillon] I’m not gonna put as much into trying to attract those new clients all the time.
[Jessie Dillon] But it’ll just be so nice to have the flexibility to say, you know what?
[Jessie Dillon] I’m gonna take three months off, or I’m gonna take the whole summer off and travel or do whatever.
[Jessie Dillon] Like, that’s really what I’m going for, but I’ll still probably work by choice.
[Mattias] Totally.
[Mattias] No.
[Mattias] That’s that’s, yeah, that’s the dream.
[Mattias] I mean, I think it’s you can, take different risks too.
[Mattias] Like, I I think there’s, something to be said for, having the freedom to explore something new that you may not have had the courage to or felt like you could, because you’re financially strapped before.
[Mattias] And, like, you know so yeah.
[Mattias] I I right now, I’m building a sales team, to free up some of my time, ideally, because I also want to take my family to, Spain for a year.
[Mattias] And, you know, without investing, without building that team, I don’t know.
[Mattias] Yeah.
[Mattias] All those things wouldn’t have happened if if I wasn’t building this stuff, you know, if I wasn’t taking these risks and chances.
[Mattias] So it’s just cool how you can kind of open more doors with, by by grinding through these deals.
[Jessie Dillon] For sure.
[Jessie Dillon] And to your point about being able to take on just projects or the different risks, I actually this past fall, I took a course on self storage.
[Jessie Dillon] And I actually really loved it.
[Jessie Dillon] Like, if anyone listening is interested, the course was with Bree the investor on Instagram.
[Jessie Dillon] I loved the course.
[Jessie Dillon] I really feel totally prepared to go look for a self storage facility, but I didn’t do it immediately because I was like, value add multifamily is just my comfort area.
[Jessie Dillon] I know I can find a great deal quickly for these two partners that I have who want to find something now.
[Jessie Dillon] So I was like, I’ll kinda circle back to self storage once I accomplish what I wanted to accomplish.
[Jessie Dillon] So I’m looking forward to doing that.
[Mattias] Yeah.
[Mattias] Yeah.
[Mattias] Totally.
[Mattias] I mean, that’s there’s some some beauty in in that for sure, that that model.
[Mattias] You don’t have toilets.
[Mattias] You don’t have a different kind of, tenant, that you can, you know and I I would imagine there’s some pretty good, write offs as well.
[Mattias] Have you gotten, into the rep status now with your investing, and you now are you doing accelerated appreciation with your, properties you you are buying?
[Jessie Dillon] I am in rep status.
[Jessie Dillon] I honestly don’t drive myself insane trying to understand all the different things when it comes to taxes.
[Jessie Dillon] Like, that’s something that I have tried to learn a lot about, and I just have maybe a mental block around it.
[Jessie Dillon] Like, I can’t retain too much of it, but I work really closely with my CPA.
[Jessie Dillon] Maybe, like, two or three times a year, we’ll have strategy calls.
[Jessie Dillon] And she works with all investors, and she herself is an investor, which is why I feel like she’s so good.
[Jessie Dillon] So, honestly, like, I live and die by whatever she tells me to do, and I don’t drive myself crazy trying to understand the why.
[Jessie Dillon] Yeah.
[Jessie Dillon] But that has also made a huge difference for me, like, working with someone who specializes in real estate.
[Jessie Dillon] I had previously worked with a CPA who, specialized in small business, and that’s why I was with him because when the salon was, like, my main thing.
[Jessie Dillon] Mhmm.
[Jessie Dillon] And I had learned enough to know that I felt like the projections that he had for my taxes that year were off.
[Jessie Dillon] And when I had consulted, my now CPA on it, she was like, yeah.
[Jessie Dillon] It’s like a $40,000 difference.
[Jessie Dillon] So
[Mattias] I’m surprised.
[Jessie Dillon] That was huge.
[Jessie Dillon] So it’s like, well, good thing I listened to enough podcast to know that something was off, like, to know to look into it.
[Jessie Dillon] You know?
[Mattias] Yeah.
[Mattias] Yeah.
[Mattias] That’s I mean, you’re you’re you’re talking about your team.
[Mattias] And I think it’s just there’s it’s so valuable.
[Mattias] It’s so valuable to have.
[Mattias] And I have, an attorney like you described as well that I can text, that I can call.
[Mattias] It’s been so huge, and and that was, you know, the reason I could, with that that fall on the ice, I I could kinda resume normal activities and not just be focused on this, possible problem, because he was like, yeah.
[Mattias] You’re you’re fine.
[Mattias] He’s not gonna be able to do anything.
[Mattias] It’s just it’s just nice to have those people.
[Mattias] And, obviously, like, one of the best ways you can give yourself a pay raise is is, you know, maximizing your taxes, from what you already earn.
[Mattias] So having a really good CPA is great.
[Mattias] Sounds like you maybe get some strategy from the CPA as well.
[Jessie Dillon] Yeah.
[Jessie Dillon] So I’m not sure that she would call herself a tax strategist, but, it seems like CPAs often don’t want to use that term.
[Jessie Dillon] Mhmm.
[Jessie Dillon] But, you know, it’s helpful that she can just say, you know, based on her experience as an investor, this is something I might wanna look into doing.
[Jessie Dillon] And yeah.
[Jessie Dillon] So she does give me some guidance.
[Jessie Dillon] And it has been really, really helpful for me and also just alleviated some of the stress around taxes to have those, like, meetings with her throughout the year to kind of make sure I know what’s coming the next tax season.
[Mattias] Sure.
[Mattias] Another question for you is as you, like, think about maybe some new opportunities and exploring some new, ventures, has the thought of syndications at all come up come to you, like, as far as leading them or even just investing them?
[Mattias] I think that you would obviously have a pretty good, ability to analyze a deal even just as a limited partner to, you know, see if it’s it makes sense, etcetera.
[Mattias] Is that been something you’ve considered at all?
[Jessie Dillon] I’ve thought a lot about syndications.
[Jessie Dillon] I think down the line, I would probably passively invest in the syndication, depending on the operator, like, if it was someone I really knew well and trusted.
[Mattias] Yeah.
[Jessie Dillon] I don’t really foresee myself being, you know, part of a group that runs a syndication.
[Jessie Dillon] I honestly kind of have, and this might be controversial, but I have always kind of had, like, a bad taste in my mouth about syndications because I just feel like there’s been this boom of a lot of people running syndications who really don’t have as much experience as I would want them to have if I was passively investing in it.
[Jessie Dillon] Yeah.
[Jessie Dillon] So it’s kinda put a bad taste in my mouth about it.
[Jessie Dillon] But there are also people who what’s that?
[Mattias] Sorry.
[Mattias] Keep keep going.
[Mattias] I I didn’t mean to interrupt.
[Jessie Dillon] Yeah.
[Jessie Dillon] There are also people who I know, like, my mentors who, you know, debate on starting a syndication, and I would absolutely invest in theirs.
[Mattias] Yeah.
[Mattias] It’s all I mean, the operator is huge, for sure.
[Mattias] And, there I was just gonna say to your point too, like, there’s been some messy ones, as of late with, you know, short term debt and project not projecting it that the interest rates would go as high as they did, cause a lot of problems, especially in the multifamily space.
[Mattias] So it’s, yeah, it’s, it’s not something to do lightly, but, talk about passive.
[Mattias] Talk about, being able to kind of not stress about the day to day.
[Mattias] It’s a pretty limited, worry kind of thing.
[Mattias] If you if you get a good deal, get a good operator.
[Jessie Dillon] Mhmm.
[Jessie Dillon] I think I’d be more likely to be a private lender than to passively invest in a syndication.
[Jessie Dillon] But, I think down the line, I could see myself doing, you know, a mix of both.
[Mattias] Well, you know, you probably would not get the tax benefits from the private lending.
[Mattias] I’m just thinking out loud that would be the one downside.
[Mattias] Yeah.
[Mattias] Because we’re we’re actually I’m projecting it to have a pretty good sales year this year.
[Mattias] And so, therefore, we are committing to another syndication, simply to get the tax benefits from it.
[Mattias] The the last one we did was, did did extremely well.
[Mattias] So we we invested $50,000.
[Mattias] The first year, we got $66,000 off of our our taxable income, and then the second year was another 23.
[Mattias] So, like, you know, year three will have doubled the amount we invested in in in write offs.
[Mattias] So we’re thinking, you know, that would be maybe another great, opportunity for, you know, a high volume sales year, to to get into something like that again.
[Mattias] And it’s Got it.
[Mattias] The return, was, like, 10 or 10 or 11%, so it was pretty good as well.
[Mattias] And then the exit strategy would they would refinance the money back, and we would, re retain, like, a, like, a 1% interest, ownership of the park until they ever sold if they ever sold.
[Mattias] So for us, it was yeah.
[Mattias] Doing it again now is mainly a play for, the tax benefits of it.
[Mattias] And then the thought of, you know, having that either sale or or cash out refinance, having that money come back, being able to recycle that into another deal, is also kind of exciting, if that were to ever happen.
[Mattias] So, it’s a it’s a interesting space though because there I’ve I’ve heard some horror stories and some pretty big names even that, people have invested in and and hasn’t gone quite right.
[Mattias] And there’s been capital calls and there’s, you know, that’s that’s definitely something to to tread lightly on.
[Mattias] Be careful.
[Jessie Dillon] And I would think that maybe this is totally wrong, but I would think that most people who passively invest in a syndication are doing it because they don’t really have the time or interest in learning how to DIY as an investor.
[Jessie Dillon] So it’s like if you don’t really have enough knowledge to invest on your own, do you have enough knowledge to bet the operator?
[Jessie Dillon] And that’s where I worry, like, is it you know, are a lot of people getting in trouble investing in syndications?
[Jessie Dillon] And that could be totally off.
[Jessie Dillon] It could be just the lens that I’m looking at it through, but I can’t imagine that that’s, like, a super rare occurrence.
[Mattias] Yeah.
[Mattias] I think they’re you know, and I think there’s also a lot of, like, marketing to get attract people that, you know, you might feel like you’re comfortable with this person, but do you really know them?
[Mattias] Are they they’re doing so much marketing for these things that are they even aware of what’s going on in these deals?
[Mattias] Yeah.
[Mattias] For example, where are they spending their time?
[Mattias] But, in in our circumstance, it was a really good friend, and and business partner in different investments that, has been in a mobile home, space for a while that, started joining up with other people.
[Mattias] And and in this circumstance, they, put an incredible amount of energy, money, and resources.
[Mattias] They have VAs, etcetera, finding off market, mobile home park deals that I don’t think I would I mean, you know, it’s possible I could I could do it myself as well, but, the deals are are good enough, that it just it’s it’s just easy, and it’s, like, it’s a it’s a total win win.
[Mattias] I mean, they’re gonna, you know, make out great too at the end when they do the capital event.
[Mattias] You know, they’re gonna have 50% ownership of this park, and I you know, I understand that.
[Mattias] I understand the benefits of being on the other side of that deal, but I also see how much work and that that they they put into it and the the whole team.
[Mattias] And and and at the end of the day, again, do I want freedom?
[Mattias] If it’s a really good deal to invest in on on the passive side, do I wanna build the whole team, to to go out and be on the GP side?
[Mattias] So, yeah, it’s Right.
[Mattias] It’s not for everybody.
[Mattias] It’s it’s something that we’ve gotten into more recently, but I was hesitant at first for sure when I was, exploring those.
[Jessie Dillon] Mhmm.
[Jessie Dillon] And isn’t it funny to say, like, even you, like, you have so much knowledge on real estate investing, and even you’re a little hesitant.
[Jessie Dillon] So
[Mattias] Yeah.
[Mattias] And I don’t know if I would have.
[Mattias] The first one was partly just I wanted experience in the space.
[Mattias] And I was like, I’m gonna the numbers all look good, but I know there’s risk.
[Mattias] I’m gonna throw in $50,000 partly because I want experience in the space, and I wanna feel what it feels like.
[Mattias] And so yeah.
[Mattias] Yeah.
[Mattias] No.
[Mattias] Totally.
[Mattias] I mean, it’s it’s, nothing’s without risk.
[Mattias] And, you again are putting your all the money into other people’s hands, that they could, you know, they could operate poorly, and they could be totally wrong, and they could be straight lying about their projections, etcetera.
[Mattias] So it’s you know, there’s definitely risk involved.
[Mattias] But Yeah.
[Mattias] Yeah.
[Mattias] I have to ask if you have any, golden nuggets you wanted to share, with listeners about, you know, if they’re looking to get into investing, or yeah.
[Mattias] If you have anything you wanna share.
[Jessie Dillon] I do.
[Jessie Dillon] So there’s a couple that I always try and work into every interview, every podcast that have been so impactful to me, and I wrote them down.
[Jessie Dillon] And I’m gonna list them off, and then if you wanna, like, dig into one of them.
[Jessie Dillon] So number one is only take advice from people who are doing exactly what you wanna be doing.
[Jessie Dillon] And then number two is to pick a strategy and laser focus on it.
[Jessie Dillon] They all work.
[Jessie Dillon] And when you chase, you know, all these different rabbits, you catch none.
[Jessie Dillon] Number three, it won’t go exactly according to the spreadsheet.
[Jessie Dillon] And number four, you ultimately get paid to be on this emotional roller coaster.
[Mattias] Those are great.
[Mattias] Those are great.
[Mattias] And and, yeah, investing, there are so many different angles and strategies, that you can go down.
[Mattias] And, I think it’s it’s good and if creative financing sense to have, like, an understanding of all the different ways you could make a deal work, and have different exit strategies.
[Mattias] But, like, you know, at the same time, like, really getting into a niche, and understanding it, maximizing it is is huge for sure.
[Jessie Dillon] Mhmm.
[Jessie Dillon] Yeah.
[Jessie Dillon] Like, right now, I co host the beginner cohort in the wire community.
[Jessie Dillon] And what me and my cohost, Jamie, see so often is so many people will say, like, you know, I I think I wanna do, like, long term rental multifamily, but I I also kind of wanna try a vacation rental.
[Jessie Dillon] And I’m seeing so much about midterm rentals.
[Jessie Dillon] And I’m thinking about this market, but I’m also thinking about that market.
[Jessie Dillon] And just having your attention spread out so much, I can almost guarantee that you’re not gonna buy anything.
[Jessie Dillon] Like, you’re not gonna take action on any of it.
[Jessie Dillon] Whereas if you just laser focus on one market, one strategy, one buy box, you’re so much more likely to take action now.
[Jessie Dillon] And you don’t have to have FOMO about all the other things that you’re thinking of trying.
[Jessie Dillon] You can do those later, but one thing at a time.
[Mattias] Yeah.
[Mattias] I love it.
[Mattias] And I I think, you know, just house hacking to start.
[Mattias] Like, that’s just such a, you know, easy way to just get some property, get some equity, and not that you have to be a starter beginning investor to do it.
[Mattias] You’re you’re saying you’re doing it as well, looking at it to to do it again.
[Mattias] But, yeah, just to, like, start start that process off and, like, you know, it’s it’s different.
[Mattias] You’re gonna, like, be emotionally invested as well, which may be good or bad, but you’ll probably be more likely to pull the trigger.
[Mattias] I would imagine, like, okay.
[Mattias] I can live here.
[Mattias] I can make this work.
[Mattias] Yeah.
[Mattias] And especially if you don’t have a lot of money.
[Mattias] Right?
[Jessie Dillon] Yeah.
[Jessie Dillon] I honestly think that everyone should be house hacking.
[Jessie Dillon] Like, whether you were intending to be a real estate investor or not, I feel like everyone should be house hacking at the very least to just subsidize your personal cost of living or maybe reduce it to nothing.
[Jessie Dillon] And even, you know, I I definitely plan on making sure I’m always capitalizing on FHA loans.
[Jessie Dillon] Like, am I, as often as possible, buying property with as little money down as possible, investments that really make sense?
[Jessie Dillon] And, yeah, like you said, I I plan on doing another house hack.
[Jessie Dillon] I just feel like it’s such a wasted opportunity to not
[Mattias] Yeah.
[Mattias] No.
[Mattias] Seriously.
[Mattias] I mean, yeah, where else can you, you know, buy like, I mean, can you buy a portfolio of stocks, for three and a half percent down?
[Jessie Dillon] Right.
[Jessie Dillon] Right.
[Jessie Dillon] Exactly.
[Mattias] Cool.
[Mattias] I I love that.
[Mattias] Those are really great tips.
[Mattias] What about a book?
[Mattias] Do you have any, fundamental books that you think everybody should read or maybe just a current favorite one?
[Jessie Dillon] Current favorite is actually The Millionaire Next Door.
[Jessie Dillon] I love a book with just, like, really impactful facts in it.
[Jessie Dillon] Like, facts that you read and you’re, like, like, woah, that’s insane, and you wanna, like, share them with everyone around you.
[Jessie Dillon] I mean, unfortunately, no one around me cares about any of the facts in this book, but I share them anyways.
[Jessie Dillon] But I thought that book really shifted how I thought about wealth and millionaire status, which
[Mattias] Mhmm.
[Jessie Dillon] Sadly, I think, you know, when I was in maybe high school, I thought that that was worth so much more.
[Jessie Dillon] And now just with what inflation has done, I’m like, is being a millionaire really as impactful as it once was?
[Jessie Dillon] The answer is obviously no.
[Jessie Dillon] But, yeah, that book really shifted how I thought about entrepreneurship, wealth.
[Jessie Dillon] Yeah.
[Jessie Dillon] It was really good.
[Mattias] Yeah.
[Mattias] It is good.
[Mattias] I actually, used to work.
[Mattias] I was doing behavior management kinda stuff in a high school.
[Mattias] Kinda actually when I got my license and started selling as well.
[Mattias] And, that I think I read that book around that time.
[Mattias] And, we I would I would talk to the kids there.
[Mattias] You know, they’re all, like, wanna be flashy and stuff and, like, talking about, you know, what what do you think a millionaire looks like?
[Mattias] What what what and, you know, they would go through all these different things.
[Mattias] Like, you know, they’d be driving a Lamborghini and all this kind of stuff, and then just kind of explained how, no.
[Mattias] Most of them are gonna be driving the the oldest car in the lot or whatever, and and they’re not, you know, spending money on Rolexes and stuff like that because, their their money is working for them.
[Mattias] So it’s a great resource.
[Mattias] Have you have you heard of, Mr.
[Mattias] Money Mustache?
[Jessie Dillon] Mhmm.
[Mattias] I was you seem like a kind of person that’s all about that, the efficiency of life as well as, like, the building of the the investments to I mean, to get to that number faster, like, obviously, the less you spend, the the easier it is to be a % passive.
[Jessie Dillon] Yeah.
[Jessie Dillon] So him and a few members of his community were in this documentary that I love playing with fire, which is on Amazon Prime.
[Jessie Dillon] It’s so good.
[Jessie Dillon] It’s, you know, all about the fire community, and there’s a lot of, like, heavy hitters in the fire community, like influencer type people who are in it.
[Jessie Dillon] And it follows this couple who is discovering fire and on the path towards fire.
[Jessie Dillon] And, yeah, I’m very much about lowering your personal cost of living as much as you can so that you can become work optional or find financial freedom faster.
[Jessie Dillon] Am I perfect at it?
[Jessie Dillon] Absolutely not.
[Jessie Dillon] And I feel like living in New England, you know, my cost of living kind of is what it is.
[Jessie Dillon] But I do think it’s just this really, like, exciting concept to lower your cost of living as much as you can.
[Jessie Dillon] And then, you know, ultimately, from whatever investment vehicle you have, be bringing in one and a half to two times that so you truly can just not work and not worry about it.
[Jessie Dillon] I mean, I think I’m someone who’s always gonna worry about money to a degree.
[Jessie Dillon] I feel like I’m just conditioned that way, but, I’m always looking at my personal cost of living and trying to figure out where there’s room for improvement.
[Mattias] Yeah.
[Mattias] I mean, mister Money Mustache is, like, just such a he’s I don’t know what the word is.
[Mattias] He’s obsessive with it.
[Mattias] I remember reading, he got, like, a special, like, fuel gauge monitor or something like that so that when he was driving you know, the rare times that he was not just biking, he was driving and spending money on gas.
[Mattias] He would, like, figure out exactly, like, how to, like, get the best possible fuel, economy that he could to, like, you know, not speeding up, obviously, all these things, but he he was able to really maximize that as well.
[Mattias] It’s just he’s, obsessive on on the efficiency of everything, and I I I don’t think I could be quite that way.
[Mattias] And I I do enjoy, working as well.
[Mattias] So, but it’s it’s really good to have those kind of, voices in your head, if you will, like, to have to have that community, in your head instead of the, you know, the I don’t know.
[Mattias] Like, trying to look and press the neighbors, kind of voices that, make make the opposite problem.
[Mattias] You you have that lifestyle creep.
[Jessie Dillon] Yeah.
[Jessie Dillon] And, like, of course, you know, like you said, he’s pretty extreme, but I think it’s so cool to just be that passionate about something.
[Jessie Dillon] Like, I’m probably not gonna be that passionate about that in particular.
[Jessie Dillon] You know, it’s hard to say that I’m so committed to fire because I get, like, Botox and filler and stuff.
[Jessie Dillon] So, obviously, I’m not that passionate about it.
[Jessie Dillon] But, and to your point too, it’s so funny to think, like, what kids think of as, like, you know, what does a wealthy person look like?
[Jessie Dillon] Like, while you were saying that I was thinking about my daughter because we, have, like, a candy dish now, like, on the coffee table, and there’s a bowl with, like, always candy in it.
[Jessie Dillon] And when I first put it out, she was like, oh, this is like a rich person thing having a candy bowl.
[Jessie Dillon] And previously, like, there was a time where she went over a new friend’s house and she was like, they have a pool.
[Jessie Dillon] Like, they’re rich, rich because they have a pool.
[Jessie Dillon] And I was like, do you have any idea how much it costs to have a pool?
[Jessie Dillon] Like, just the utility bills are crazy.
[Jessie Dillon] Like, it’s such a money sucker.
[Jessie Dillon] And I’m like, I’m thinking in my head, like your, your mother, like, barely goes to work.
[Jessie Dillon] Shouldn’t that give you some indication that, like, we’re doing okay too.
[Jessie Dillon] Like, we don’t have a pool, but, but, yeah, it was just so funny, like the pool of the candy dish, but to me, I’m like, you know, most days I’m home, and I’m not punching a clock.
[Jessie Dillon] I’m not really working remotely.
[Jessie Dillon] Mhmm.
[Jessie Dillon] So to me, that’s like, I’m so rich with time now.
[Mattias] What an awesome lesson So funny.
[Mattias] To give to your to your kids too.
[Mattias] I mean, I think that that stuff, whether or not I mean, you probably talk about now too.
[Mattias] You said your daughter is 17.
[Mattias] So, but I I think even if you don’t, I think they just they will soak up that.
[Mattias] They’ll they’ll think back and they’ll they’ll realize where your priorities were and and kind of where your choices were, to it’s it’s a really great lesson.
[Jessie Dillon] Mhmm.
[Jessie Dillon] And I look forward to her being work optional early in life too because we’ve already kind of instilled the
[Mattias] Oh, that’s cool.
[Jessie Dillon] You know, we’ve made the agreement that she invests 50% of her income.
[Jessie Dillon] So she already has more in her retirement account than I think a lot of adults do.
[Jessie Dillon] I showed her a timeline of the average lifespan and different milestones, and I was like, when on this timeline do you want to not have to work anymore?
[Jessie Dillon] And she chose 38.
[Jessie Dillon] So she committed to investing half of her paycheck until that time, and then we can go retire together.
[Mattias] That’s awesome.
[Mattias] That’s so cool.
[Mattias] I had a a friend that, he his dad, Nick, made him max out a Roth IRA as soon as he could, as soon as he I guess, he had to I guess, he had to work to be able to do that.
[Mattias] But I think he, you know, he helped subsidize it or whatever, but they he did all the way through, his college and, whatever he could in high school, maxed it out.
[Mattias] And then when he got out of college, he used that as a down payment to, buy a house.
[Mattias] He house hacked that for, through grad school, through, you know, for a long time and and never had a mortgage.
[Mattias] And it’s just That’s awesome.
[Mattias] What a what a gift.
[Mattias] So that’s really cool that your daughter’s doing stuff like that too.
[Mattias] Jesse, where could people find you if they wanted to follow you on Instagram or, you know, where where where are you at?
[Mattias] Where where people reach out?
[Jessie Dillon] Instagram’s definitely best.
[Jessie Dillon] So I’m @jessedylan_ with an underscore at the end.
[Jessie Dillon] And in my bio, there’s a link to join my email newsletter.
[Jessie Dillon] That’s where I mostly talk about all my real estate ventures.
[Mattias] Cool.
[Mattias] Well, thanks so much for being on the show.
[Mattias] It’s been a great conversation.
[Jessie Dillon] Yeah.
[Jessie Dillon] Thank you for having me.
[Mattias] I’m motivated now to stop spending money.
[Mattias] Good.
[Erica] Thanks for listening to the REI agent.
[Mattias] If you enjoyed this episode, hit subscribe to catch new shows every week.
[Erica] Visit REIagent.com for more content.
[Mattias] Until next time, keep building the life you want.
[Erica] All content in the show is not investment advice or mental health therapy.
[Erica] It is intended for entertainment purposes only.

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