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

[0:00] Welcome to the REI Agent, a holistic approach to life through real estate. I’m Matthias, an agent and investor. And I’m Erica, a licensed therapist. Join us as we interview guests that also strive to live bold and fulfilled lives through business and real estate investing. Tune in every week for interviews with real estate agents and investors. Ready to level up? Let’s do it.

[0:24] Welcome back to the REI Agent. Your host here, Matthias. Erica is enrolling our middle child into preschool, which is crazy. Yeah, our kids are growing up. That daughter gave me this beautiful mug. It’s a rainbow color. I don’t know if you can see it. And it says low-key thriving on it. And I don’t know if she read that, but that is just the sweetest mug ever. I hope this thing never breaks because I love it. Today, we have Jessie Dillon on the podcast. She is a business owner that got really into the FIRE community and just went after Reynolds as a route to becoming financially independent. So FIRE, if you’re not familiar with it, is financially independent. Retire early. And I’ve read different blogs throughout the years and been kind of part of those kind of communities, that kind of mindset.

[1:25] Part of me enjoys enjoying life. And I think living as frugally as possible isn’t always the way I want to live. I think there’s a bit of a balance there. And I also am like a busy person. So I like to get after it a little bit. And I think enjoying some of the fruits of what the business that I’ve created is okay. But living that balanced life is certainly good. 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 behave ultimately. 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.

[2:25] And it was just to have that community because we kind of got ostracized a little bit from some of Erica’s friends. And I couldn’t see many of my friends as much as I like to, you know, whenever they were wanting to go out, we just didn’t for the most part. 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. And I just don’t know if that would have been possible if we didn’t have that kind of like constant input from the podcast, Dave Ramsey podcast. And so I think that’s just kind of a, you can call it brainwashing if you want. 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.

[3:12] I think it played a really good key role in our life. So I’m not a hater. But I certainly, I’m not subscribed to his plan or his baby steps at this time. I’m trying to leverage real estate as much as I can. But all I have to say is, you know, I just think it’s really important to just be intentional about how you are filling your brain with things. And if you are, you know, constantly watching like, you know, the, I don’t know, celebrities or like the real housewives. I’ve actually never seen that show. So I don’t even know what it’s about. But like, you know, if you’re like having this glamorous, inundation of glamorous living in your brain, that’s what you’re going to want. And you’re going to have your lifestyle creep up.

[3:57] And 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 listing appointment in a Porsche and be, you know, wearing a fancy suit with Rolex watches or whatever. You can do that kind of stuff too. But, you know, that’s just going to make your lifestyle a lot more expensive. And if you got to just think through, is that what you want over having more freedom of time, et cetera. So, yeah, just being intentional about what you put in your brain, I think, is just really, really important. And surrounding yourself with the community of people that are like-minded, that are where you want to be, I think is also important for that.

[4:45] So you can do, listen to podcasts. You can read books that will help you get there. 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 where you want to be. I think those are all great ways of kind of just keeping yourself in the right path. And, you know, one of the things that we just talk about all the time is, you know, trying to live intentionally. And if you don’t, you know, life will just happen to you. So pick up a book, find a new podcast that fits kind of the life that you want to be living, that you feel like you should be living, and just start brainwashing yourself. Use it as a trick, you know.

[5:27] Brainwash yourself for the good. Anyway, without further ado, today on the show, we have Jessie Dillon. She’s coming out of Massachusetts. And like I said, she’s into the FIRE movement and wanting to retire early through real estate, mainly as her vehicle of choice. So without further ado, here’s Jessie. Welcome back to the RI Agent Podcast. I’m here with Jessie Dillon. Jessie, thanks so much for joining us. Hey, thank you for having me. Jessie, you are in the Massachusetts area. You’re an investor and a business owner. Can you tell us a little bit about your story and how you got into real estate investing? Yeah, of course. So I’ve always been in the beauty industry since like 2011. And in 2017, I went off on my own, started my own business.

[6:20] And right away, I fell in love with business and social media marketing. And my business really did take off right away. It’s a small permanent makeup studio. So we tattooed brows, lips, and eyeliner and do a couple accessory services. But it took off really, really well, a little too well. And 2020 came and I realized just how burnt out I was getting. I think a lot of small business owners could relate. My business was me. I was my business. I feel like I was working 24-7. I could never stop thinking about it. And it also really was taking a toll on my body physically. It’s a lot of repetitive movements and being hunched over. So I started looking into this whole fire thing. And I think it was a Facebook clickbait article where I first heard that term.

[7:11] And it was about a girl in her late 20s who was going to be retiring by the time she was 30. And I was like, I have to figure out whatever she’s doing. So I read it. And I actually messaged her on Instagram. And we talked a bit. And she recommended some books and podcasts. And first, I went hard with investing the highest percentage of my income I could in index funds. And I was fortunate to be able to achieve a 70% savings rate. But I realized I was going to have to do this for 11 years to actually retire that way. And I just knew I couldn’t keep that pace up for that long. So I continued diving into all these fire podcasts. And there was a real estate investor on one of them. 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.

[8:00] I’m not 100% bought into that idea now that I’m, you know, down this path. But that sounded a lot better to me. So I was like, I’ve already figured out this business thing. I guarantee I can figure this out too. And this was fall 2021. I just started listening to every single podcast, reading all the books. All day while I was with my clients at the studio, I was listening to a real estate podcast. So my clients were kind of learning alongside me. And the following January 2022 is when I closed on my first rental. 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. Okay. Wow. That’s amazing. And I guess one of the questions I have for you right off the bat is, did that new goal, that new target make the grind less bad?

[8:56] Like it had more of a purpose or you had like, you know, okay, I’m going to do this grind in the beauty salon. Even though I was burnout, now I have like a renewed sense of purpose. Did you feel that at all? I think it was more so almost like a light at the end of the tunnel that made it more tolerable. Like in the beauty industry, no one has a retirement plan. No one has a 401k. 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. So this kind of no end in sight. And I do really, really enjoy my work in the beauty industry. 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.

[9:45] And that’s really what I’m chasing. I probably honestly will continue doing what I do in the beauty world, but just on a, you know, like less frequent basis. Sure. No, I think, I mean, that’s very common. I think with like, you know, small businesses in general, 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. They’re still showing houses into their eighties or whatever. And honestly are just working until they die. And it’s some of them just, you know, love it and want to keep going. And others, you know, just had, didn’t plan maybe the best and, and are just kind of stuck having to keep the bills going. One of the things we, you know, talk about as a lofty goal is to be like a hundred percent passive.

[10:31] 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, whatever, whatever, what other business you’re in. 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. Cause that’s a big factor, right? Obviously if you’re getting new cashflow and you’re spending it right away with a new lease or whatever, it’s just not really going to replace your needed income. But yeah, that a hundred percent goal, it sounds like is you’re said a year and a half away already. Yeah. I think I’m about a year and a half away.

[11:09] Um, 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 kind of difficult to close for everyone lately. Um, so long as these two make it to the finish line, that will actually in theory, complete my portfolio. Um, it’ll get me to where I have been wanting to go this whole time. 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 cashflow 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. Well, let’s, let’s dive into that a little bit. So was that the first deal that you did was a multifamily value add?

[11:54] It was a two unit. It was not value add. It actually was, I don’t want to say turnkey. So it was two units. Um, the unit that was owner occupied was in perfect condition. Um, the house was really, really well kept. And then there was, um, 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 30 years. So it hadn’t been touched and needed a lot of love when they moved out. But I do still own that property today. Yeah. I was going to say, if you jumped, if you jumped fully into like a, like your first deal was like a 30 plex or something else, you look, what, what podcast did you listen to? Cause that’s impressive.

[12:35] Um, so what have you bought and since then, did you, did you go into bigger, um, multifamily from there or. So that first year I bought the two unit. And then a few months later, um, I really wanted to try my hand at short-term rentals because, you know, coming from beauty customer service is so huge for me. And, um, I saw how that was going to translate to being a Airbnb host. Um, so I bought a single family home up in New Hampshire. Um, I have actually since sold that creatively and then summer 2022, I bought my two family house hack. Um, and then I also midterm rent my guest room and that property, um, I’m sitting in that property right now. And then I had, didn’t close on anything for a year.

[13:21] And I sort of felt like I had done something wrong because I was tapped out of down payments 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, um, a high ticket area, like buying in mass New Hampshire. Um, so that’s when I kind of opened my mind to partnerships and almost a year after I opened my mind to partnerships, which it was actually BP con that year that made me reconsider partnering. Um, I closed on a 13 unit value add multifamily in Illinois with a partner. Um, 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, um, a 12 unit and a 13 unit also in Illinois.

[14:12] Okay. Yeah. Now, how was the Illinois purchases based on the partner you found, or was that based on the market, uh, that you, like you did research market research and found that that was the best market to be in? Market research. So, um, 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. 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. 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.

[15:00] Right. So that was, that went on for about six months and then we decided together, you know, clearly that is not working, but if we’re doing deals around this size, we’re going to have to use a property management company anyways, like the lender will require it. So is there really a purpose in staying local if we could find something that’s just a better ROI long distance? Um, and I’m happy that I have the flexibility to travel a lot. 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. 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.

[15:44] Um, but the more we looked into it, we love 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, but we were going to buy in mass anyways, which also is. So that’s kind of the lens that I’m used to operating through anyways. Okay. Yeah. It can be really hard if you are in an area that is, uh, just, you know, an appreciation heavy market. That’s where we are as well. We’re, we’re Virginia. So we’re also, um, East coast. Uh, I think there’s just people that, you know, they’re, maybe they’re 1030 wanting, uh, money into something else and they’re just happy to park it. And it’s just like, this isn’t pencil out.

[16:23] Like how is the cap rates worse than the interest rate that we’re paying? Like, this isn’t gonna, this just isn’t gonna work. So, um, yeah, that, that’s awesome. I mean, did it, did it take, uh, was it nerve wracking at all to start going into a market that you weren’t as familiar with that? You maybe weren’t able to just drive by the property or looking to buy, uh, did, did, you know, investing in a different market that pose any kind of mental challenge that you had overcome? Not really. Honestly. Um, 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. And it’s interesting to play that through in your mind. Like, well, why do you need to drive by it?

[17:06] Does it matter if you drive by it or if someone else drives, drives by and sends you a video? And I think it’s just, you know, you don’t want to like, let go of control of your investment. But I mean, with business in general, I have learned to delegate and let go of control a bit and understand that if I want to 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 want to do it. So I feel like coming from an entrepreneurial background really helped me be okay with investing long distance. Yeah, that makes sense. And to your point, I mean, like if it’s kind of forces your hand to get the professionals in place, you said you might have needed it anyway with a loan.

[17:56] But I think that’s another challenge some people might have is that they feel like they’re going to do a better job running it out themselves and they won’t have that control. And, you know, when you think about it, kind of comparing it to like stocks, if you will, like, I mean, that’s one of the benefits of real estate that can be an argument can be made for is that you get you can go see it, you can go like, you know, feel it, you know, the market, you have much more understanding of the actual 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 has started well. 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.

[18:39] But to your point, like if you are chasing freedom, you know, delegating that stuff out and growing in that way so you can get the numbers to work better and a better market for rentals makes a ton of sense. 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. You can’t be completely hands off and never think about it or worry about it or ask about it at that point. 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. And you can’t really completely take your hand off the pulse, you know, like you still have to be overseeing and tapped into like what’s going on.

[19:31] I mean, can you describe that a little bit in more detail? Are you looking at like, you know, comparable property rents? Like what, how do you do that to kind of help make sure it performs well? Yeah. 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, but my property manager has a really good pulse on like what I want to be involved in or included in. So we’ll often end up talking a couple of times in between those check-ins. But every month I’ll send an email kind of like touching base on different things that we were talking about the previous month. So what’s going on with lease renewals? Like for each one, what are we asking for? Did they sign yet?

[20:17] What are the, what are the comps that we were basing that on for vacant units? 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? They helped me along with appealing the new assessed value recently. So I’ll touch base every month and I have a pretty good pulse of what’s going on in these buildings. Sure. No, that makes sense. 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, or? Yep, absolutely. And then they also loop me in on anything bigger. So for example, there was a toilet had leaked and it caused like a lot of water damage in the unit below it. And there was like a 4am emergency call about it. 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. Okay. That’s nice. I was recently camping last year and I didn’t, when I went camping, I didn’t know if I’d had service or not. I did. But I got like three calls

[21:31] from a tenant at like 4am in the morning. Like, why, why are you bothering me? And it was a hot water heater had leaked above and was pouring water down in his unit. So it was good. He called me, but it could have been nicer if that was a property manager handling that while I was camping. Yeah. 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. 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. Um, and I did have to kind of get over mental blocks around that, like hiring property management for local properties. Like I could easily be doing that, but I just don’t want to. And giving myself permission to hire it out just because I don’t want to do that was huge. 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.

[22:36] Cause I get really anxious about like emergency issues and, um, you know, getting calls at all hours and stuff. Like I actually feel too emotionally up and down about properties that are local to me and properties that are long distance. I really see them more as like a business. So I just think about it differently. And I, I enjoy how I think about the long distance properties a lot more. I mean, that’s what it is. They, they are their businesses. Um, and each, each property you consider a different business that you own. And I think that’s a really good lens to have. And at the end of the day, again, if you are, if your goal is to free up your time, um, and to, to have more freedom, like learning to, to pass on the buck, I I’m kind of talking to myself right now. I haven’t done it yet. Um, I am a real estate agent. So like I kind of am on call anyway, all the time. Um, so it hasn’t been too different. Um, but it is a different type of, and there’s liability involved too, especially as a licensee, like you, um, you know, if somebody were to find you liable for, uh, you know, fair housing, that could, that a violation there that you could, you know, lose

[23:48] your license and, and that would impact your, your whole livelihood. 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. And, um, cause you know, if I lose my license, that’s, uh, that’s a big deal. Yeah, definitely. Have you had, um, the, have you ever, have you had like any like falls or accidents in your property too? That’s another thing that just came to mind with liability is I had somebody slip on some ice, uh, this past year, um, this past winter. And, you know, again, another headache that disrupted my day that I, you know, would have need to have. I, if I had that, you know, property managed. I have not had that. The only thing that comes to mind, um, which I feel like a lot of investors probably would also be as scared as I was when this happened. Um, I did have a tenant who had a couple of young kids and, um, she had told me once that one of her kids tested positive for lead and yeah. And the unit was certified lead compliant, um, in mass, if there’s a child living in the unit under a certain age, it has to be. And it was so, but still I was immediately

[25:05] panicked 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. 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. Like it’s so rare to find an attorney who, you know, when I have a quick question, I can text him, I can email him, I can call him and he’ll get on the phone and explain the answer to me for 20 minutes. And I now get a bill afterwards, but I refer a lot of business to him and I always go to him for my local transactions. And, um, you know, he explained to me how all of that works, um, where I can learn more about it on mass.gov.

[25:52] Um, 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. I wrote a whole note in my phone about it. And I regularly share that with other investors. Um, and you know, it ended up being completely unrelated to the house, but, um, it was a great learning experience. Yeah. Yeah. And I think it’s just different when it’s your property, right. Versus, uh, so I think like, you know, problems can cause you, you know, headaches and anxiety and, and all that stuff. If you’re a property management manager, you probably get a little bit numb to, to dealing with things, but it’s just different too. And it’s not yours. Um, and it’s, it’s kind of like you’re, you’re helping people through it. It’s just a little bit more removed. So, um, yeah, there’s, there’s definitely benefits to that. When you, um, as you go forward, um, once you hit that, you know, a hundred percent, uh, do you think you’ll continue to invest, uh, in real estate or do you think you’re just going to retire on a beach and drink, uh, mojitos all day? I’ve been thinking about that

[27:00] a lot lately because it feels like something that’s getting closer. Um, 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. Um, I have four partners and I’d be totally happy to do another deal with someone I’m already established with. Um, and then also I’d like to do another house hack probably next year. Um, I don’t really see myself wanting to completely stop trying with real estate because I actually do enjoy it. And I think once I’m past my finish line, it’s going to become even more enjoyable because I won’t feel like I’m chasing after something. I’ll feel like I’m doing it just cause I, I love the game of it. Like it’s like fitting these puzzles pieces together. You know what I mean? Like I, I do really like it and I have this skillset with like finding and analyzing deals and then operating these deals. So, um, yeah, I think I’ll probably still be open to it, but I won’t be chasing after new deals, new partnerships, you know, um, similarly to with permanent makeup, like I’ll probably continue doing it, but it’ll most likely

[28:16] be more of my returning clients. I’m not going to put as much into trying to attract those new clients all the time. Um, but it’ll just be so nice to have the flexibility to say, you know what, I’m going to take three months off or I’m going to take the whole summer off and travel or do whatever. Like that’s really what I’m going for, but I’ll still probably work by choice. Totally. No, that’s, that’s, yeah, that’s the dream. I mean, I think it’s, you can, uh, take different risks too. Like, I think there’s, uh, something to be said for, uh, having the freedom to explore something new that you may not have had the courage to, or felt like you could, uh, because you’re financially strapped before. Um, and like, you know, so yeah, I, right now I’m building a sales team, uh, to free up some of my time, um, ideally cause I also want to take my family to, uh, Spain for a year. Um, and you know, without investing, without building that team, um, I don’t know. Yeah. 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. So it’s just cool how you can kind of

[29:20] open more doors with, um, by, by grinding through these deals for sure. Yeah. 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. Um, and I actually really loved it. Like if anyone listening is interested, the course was a breathy investor on Instagram. Um, I loved the course. 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. I know I can find a great deal quickly for these two partners that I have who want to find something now. So I was like, I’ll kind of circle back to self-storage once I accomplished what I wanted to accomplish. So I’m looking forward to doing that. Yeah, yeah, totally. Um, I mean, that’s, there’s some beauty in that for sure.

[30:14] Uh, that, that model, um, you don’t have toilets, you know, different kind of a tenant, uh, that you can, you know, and I, I would imagine there’s some pretty good, uh, write-offs as well. Um, have you gotten, um, into the rep status now with your investing? Um, and you now, are you doing accelerated appreciation with your, uh, properties you, you are buying? I am in rep status. Um, I honestly don’t drive myself insane trying to understand all the different things when it comes to taxes. Like that’s something that I have tried to learn a lot about and I just have maybe a mental block around it. Like I can’t retain too much of it, but I work really closely with my CPA, maybe like two or three times a year. We’ll have strategy calls and she works with all investors and she herself is an investor, which is why I feel like she’s so good.

[31:11] Um, 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. Um, that has also made a huge difference for me, like working with someone who specializes in real estate. I had previously worked with a CPA who, um, specialized in small business and that’s why I was with him because when the salon was like my main thing. Um, and I had learned enough to know that I felt like the projections that he had for my taxes that year were off. And when I had consulted, um, my now CPA on it, she was like, yeah, it’s like a $40,000 difference. So that was huge. So it’s like, well, good thing. I listened to enough podcasts to know that something was off, like to know, to look into it, you know? Yeah. Yeah. That’s, I mean, you’re, you’re, you’re talking about your team. Um, and I think it’s just, there’s, it’s so valuable.

[32:08] It’s so valuable to have. And I have an attorney like you described as well that I can text that I can call. Um, it’s been so huge. And that was, you know, the reason I could, uh, with that, that fall on the ice, I could kind of resume normal activities and not just be focused on this, uh, possible problem. Uh, because he was like, yeah, you’re, you’re fine. He’s not going to be able to do anything. Um, it’s just, it’s just nice to have those people. And obviously like one of the best ways you can give yourself a pay raise is, is, uh, you know, maximizing your taxes, um, uh, from what you already earned. So having a really good CPA is great. Um, it sounds like you maybe get some strategy from the CPA as well. Yeah. So I’m not sure that she would call herself a tax strategist, but, um, it seems like CPAs often don’t want to use that term, 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 want to look into doing. And yeah, so she does give me some guidance. Um, and it has been really, really helpful for me and also just alleviated some of the stress around taxes to have those like,

[33:17] um, meetings with her throughout the year to kind of make sure I know what’s coming the next tax season. Sure. Um, another question for you is as you like, think about maybe some new opportunities and exploring some new, um, ventures, uh, has the thought of syndications at all come up, come to you, like as far as leading them or even just investing them, I think that you would obviously have a pretty good, uh, ability to analyze a deal, even just as a limited partner to, you know, see if it’s, it makes sense. Um, et cetera. Is that been something you’ve considered at all? I’ve thought a lot about syndications. Um, I think down the line, I would probably passively invest in a syndication, um, depending on the operator. Like if it was someone I really knew well and trusted, um, I don’t really foresee myself being, you know, part of a group that runs a syndication. Um, 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

[34:29] want them to have if I was passively investing in it. Um, so it’s kind of put a bad taste in my mouth about it. Um, but there are also people who, what’s that? Sorry, keep going. I didn’t mean to interrupt. Yeah. 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. Yeah. It’s all, I mean, the operator is huge, um, for sure. And, uh, there, I was just going to say to your point too, like there’s been some messy ones, uh, as of late with, uh, you know, short-term debt and project, not projecting it, that the interest rates would go as high as they did, uh, cause a lot of problems, especially in the multifamily space. So it’s, yeah, it’s, uh, it’s not something to do lightly, but, um, talk about passive, uh, talk about, uh, being able to kind of not stress about the day to day. It’s a pretty limited, uh, worry kind of thing. If you, if you get a good deal, get a good operator.

[35:29] Hmm. I think I’d be more likely to be a private lender than to passively invest in a syndication. But, um, I think down the line, I could see myself doing, you know, a mix of both. Well, you know, you probably would not get the tax benefits from the private lending. I’m just thinking out loud. That would be the one downside. Um, yeah, cause we’re, we’re actually, I’m projecting it to have a pretty good sales year this year. Um, and so therefore we are committing to, another syndication, uh, simply to get the tax benefits from it. Uh, the, the last one we did was, um, did, did extremely well. So we, we invested $50,000. Uh, the first year we got $66,000 off of our, our taxable income. And then the second year was another 23. So like, you know, year three, we’ll have doubled the amount we invested in, in, in write-offs. Um, so we were thinking, you know, that would be maybe another great, uh, opportunity for, you know, a high volume sales year, uh, to, to get into something like that again.

[36:31] Mm. And it’s, and the return, um, was like 10 or 10 or 11%. So it was pretty good as well. Um, and then the exit strategy would, they would refinance the money back and we would, uh, re retain like a, like a 1% interest, uh, uh, ownership of the park until they ever sold, if they ever sold. Um, so for us, it was, yeah, doing it again now is mainly a play for, uh, the tax benefits of it. Um, and then the thought of, you know, having that, uh, either sale or, or cash out refinance, uh, having that money come back, being able to recycle that into another deal, um, is also kind of exciting, um, if that were to ever happen. So, uh, it’s a, it’s an interesting space though, cause there I’ve, I’ve heard some horror stories and some pretty big names even that, um, people have invested in and then hasn’t gone quite right.

[37:27] And there’s been capital calls and there’s, you know, that’s, it’s definitely something to tread lightly on. Be careful. Yeah. 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. So it’s like, if you don’t really have enough knowledge to invest on your own, do you have enough knowledge to vet the operator? And that’s where I worry, like, is it, you know, are a lot of people getting in trouble investing in syndications? And that could be totally off. 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.

[38:10] Yeah. I think there, you know, and I think there’s also a lot of like, um, marketing to get, attract people and that, you know, you might feel like you’re comfortable with this person, but do you really know them? Um, are they, they’re doing so much, um, marketing for these things that are they even aware of what’s going on in these deals? Yeah. For example, um, where are they spending their time? But, uh, in, in our circumstance, it was a really good friend, uh, and business partner in different investments that, uh, has been in a mobile home, uh, space for a while that, uh, started joining up with other people. And, and in this circumstance, uh, they, uh, put an incredible amount of energy, money and, uh, resources. They have VAs, et cetera, uh, finding off market, uh, mobile home park deals that I don’t think I would, I mean, I, you know, it’s possible I could, I could do it myself as well, but, uh, the deals are good enough, um, that it just, it’s, it’s, it’s easy. And it’s like, it’s a total win-win. I mean, they’re going to, you know, make out great too. At the end, when they do the capital event, you know, they’re going to have 50%

[39:17] ownership of this park. And I, you know, I understand that I understand the benefits of being on the other side of that deal. Um, but I also see how much work and that, that they, they put into it and the whole team. And, and, and at the end of the day, again, do I want freedom if it’s a really good deal to invest in on, on the passive side, do I want to build the whole team, uh, to, to go out and be on the GP side? So yeah, it’s, it’s not for everybody. It’s, it’s a something that we’ve gotten into more recently, but I was hesitant at first for sure when I was, uh, exploring those. And isn’t it funny to say like, even you’d like, you have so much knowledge on real estate investing and even you’re a little hesitant. So, yeah. And I don’t know if I would have, um, the first one was partly just, I wanted experience in the space and I was like, I’m going to, the numbers all look good, but I know there’s risk. I’m going to throw in $50,000 partly because I want experience in the space and I want to feel what it feels like. Um, and so, yeah, yeah, no, totally. I mean, it’s, it’s, uh, nothing’s without risk and, uh, you again are putting your,

[40:30] all the money into other people’s hands, um, that they could, you know, they could operate it poorly and they could be totally wrong. They could be straight lying about their projections, et cetera. So it’s, you know, there’s definitely risk involved, but yeah. Yeah. Um, I have to ask if you have any, uh, golden nuggets you wanted to share, uh, with listeners about, you know, if they’re looking to get into investing, um, or yeah, if you have anything you want to share. I do. 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 and I’m going to list them off. And then if you want to like dig into one of them. So number one is only take advice from people who are doing exactly what you want to be doing. And then number two is to pick a strategy and laser focus on it.

[41:23] They all work. And when you chase, you know, all these different rabbits, you catch none. Number three, it won’t go exactly according to the spreadsheet. And number four, you ultimately get paid to be on this emotional rollercoaster. Those are great. Those are great. And, and yeah, investing, there are so many different angles and strategies, uh, that you can go down. 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, um, and have different exit strategies, but like, you know, at the same time, like really getting into a niche, um, and understanding it, maximizing it is, is huge for sure. Yeah. Like right now I co-host the beginner cohort in the wire community and what me and my co-host Jamie see so often is so many people will say like, you know, I, I think I want to do like, um, long-term rental multifamily, but I also kind of want to try a vacation rental. And I’m seeing so much about midterm rentals and I’m thinking about this market, but I’m also thinking about that market and just having your attention spread out so much. I can almost guarantee that you’re not going

[42:37] to buy anything. Like you’re not going to take action on any of it. Whereas if you just laser focus on one market, one strategy, one buy box, you’re so much more likely to take action now. And you don’t have to have FOMO about all the other things that you’re thinking of trying. You can do those later, but one thing at a time. Yeah. I love it. And I think, you know, just house hacking to start. Um, like that’s just such a, you know, easy way to just get some property, get some equity. Um, and not that you have to be a starter beginning investor to do it. You’re saying you’re doing it as well, looking at it to, to do it again. Um, but yeah, just to like start, start that process off. And like, you know, it’s, it’s different. You’re going to like be emotionally invested as well, which may be good or bad, but you’ll probably be more likely to pull the trigger. I would imagine like, okay, I can live here. I can make this work. Um, yeah. And especially if you don’t have a lot of money, right? Yeah. I honestly think that everyone should be house hacking. Like whether you were intending to be a real estate investor or not, I feel like everyone should be house hacking

[43:44] at the very least to just subsidize your personal cost of living or maybe reduce it to nothing. Um, and even, you know, I, I definitely plan on making sure I’m always capitalizing on FHA loans. Like, am I as often as possible buying property with as little money down as possible investments that really make sense? Um, and yeah, like you said, I, I plan on doing another house hack. I just feel like it’s such a wasted opportunity to not. Yeah, no, seriously. I mean, yeah. Where else can you, um, you know, buy, like, I mean, can you buy a portfolio of stocks, uh, for three and a half percent down? Right. Exactly. Um, cool. I love that. Uh, those are really great tips. Um, what about a book? Do you have any fundamental books that you think everybody should read or maybe just a current favorite one? Um, current favorite is actually the millionaire next door. I love a book with just like really impactful facts in it, like facts that you read and you’re like, Whoa, that’s insane. And you want to like share them with everyone around you. I mean, unfortunately no one around me cares about any of the facts in this book, but I share them anyways, but I thought that book really shifted

[45:02] how I thought about wealth and millionaire status, which sadly, I think, you know, when I was in maybe high school, I thought that that was worth so much more. And now just with what inflation has done, I’m like, is being a millionaire really as impactful as it once was the answer is obviously no, but, um, yeah, that book really shifted how I thought about entrepreneurship wealth. Um, yeah, it was really good. Yeah, it is good. I actually, uh, used to work, I was doing behavior management kind of stuff in a high school, um, kind of actually when I got my license and started selling as well. And, uh, that, I think I read that book around that time and, uh, we, I would, I would talk to the kids there, you know, they’re all like want to be flashy and stuff. And like, so talking about, you know, what, what do you think a millionaire looks like? What, what, what, and you know, they would go through all these different things like, you know, they’d be driving a Lamborghini and all this kind of stuff. And then just kind of explained how, no, most of them are going to be driving the oldest car in the lot or whatever. And they’re not, you know, spending money on Rolexes and stuff like

[46:10] that because their, their money is working for them. Um, so it’s a great resource. Have you, have you heard of, um, Mr. Money Mustache? I was, you seem like a kind of person that’s all about that, the efficiency of life as well as like the building up the investments to, I mean, to get to that number faster, like obviously the less you spend, the easier it is to be a hundred percent passive. Yeah. So him and a few members of his community were in this documentary that I love playing with fire, which is on Amazon prime. Um, it’s so good. It’s, um, 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. And it follows this couple who is discovering fire and on the path towards fire. And, um, 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. Um, am I perfect at it?

[47:12] Absolutely not. And I feel like living in new England, you know, my cost of living kind of is what it is, but I do think it’s just this really like exciting concept to lower your cost of living as much as you can. 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. I mean, I think I’m someone who’s always going to worry about money to a degree. I feel like I’m just conditioned that way, but, um, I’m always looking at my personal cost of living and trying to figure out where there’s room for improvement. Yeah. I mean, Mr. Money Mustache is like just such a, um, he’s, I don’t know what the word is. He’s obsessive with it. Um, I remember reading, um, 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.

[48:08] Um, he would like figure out exactly like how to like at the best possible fuel, uh, 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. It’s just, he’s, uh, uh, obsessive on, on the efficiency of everything. And I, I, I don’t think I could be quite that way. Um, and I, I do enjoy, um, working as well. So, um, but it’s, it’s really good to have those kinds of, uh, voices in your head, if you will, like to have, to have that community, uh, in your head instead of the, you know, the, I don’t know, like trying to look and press to the neighbors, uh, kind of voices that, uh, make, make the opposite problem. You, you have that lifestyle creep. Yeah. 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. Like, I’m probably not going to be that passionate about that in particular. Um, you know, I, it’s hard to say that I’m so committed to fire because I get like Botox and filler and stuff. So obviously I’m not that passionate about it, but, um, and to your point too, it’s so funny to think like what kids

[49:17] think of as like, you know, what does a wealthy person look like? Like while you were saying that, I was thinking about my daughter, cause we have like a candy dish now, like on the coffee table and there’s a bowl with like always candy in it. And when I first put it out, she was like, Oh, this is like a rich person thing, having a candy bowl. And previously, like there was a time where she went over a new friend’s house and she was like, they have a pool, like they’re rich, rich. Cause they have a pool. And I was like, do you have any idea how much it costs to have a pool? Like just the utility bills are crazy. Like it’s such a money sucker. And I’m like, I’m thinking in my head, like your, your mother, like barely goes to work. Shouldn’t that give you some indication that like, we’re doing okay too. Like we don’t have a pool, but, but yeah, it’s just so funny.

[50:06] Like the pool, the candy dish. But to me, I’m like, you know, most days I’m home and I’m not punching a clock. I’m not really working remotely. So to me, that’s like, I’m so rich with time now. What an awesome lesson to give to your, to your kids too. I mean, I think that that stuff, whether or not, I mean, you probably talk about now too, you said your daughter’s 17. So, but I think even if you don’t, I think they just, they will soak up that they’ll, they’ll think back and they’ll realize where your priorities were and kind of where your choices were to, it’s a really great lesson. And I look forward to her being a work optional early in life too, because we’ve already kind of instilled the, you know, we’ve made the agreement that she invests 50% of her income.

[50:57] So she already has more in her retirement account than I think a lot of adults do. 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? And she chose 38. So she committed to investing half of her paycheck until that time. And then we can go retire together. That’s awesome. That’s so cool. I had a friend that he, his dad 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. 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, max it out. And then when he got out of college, he used that as a down payment to buy a house. He house hacked that for, through grad school, through, you know, for a long time and never had a mortgage. And it’s just, what a, what a gift.

[51:52] Um, so that’s really cool that your daughter’s doing stuff like that too.

[51:57] Um, Jesse, where could people find you if they wanted to follow you on Instagram or, you know, where, where, where are you at or where people reach out? Instagram’s definitely best. So I’m Jesse Dillon with an underscore at the end. And in my bio, there’s a link to join my email newsletter. That’s where I mostly talk about all my real estate ventures. Cool. Well, thanks so much for being on the show. It’s been a great conversation. Yeah. Thank you for having me. I’m motivated now to stop spending money. Good.

[52:27] Thanks for listening to the REI agent. If you enjoyed this episode, hit subscribe to catch new shows every week, visit REI agent.com for more content until next time. Keep building the life you want. All content in the show is not investment advice or mental health therapy. It is intended for entertainment purposes only.