Many rookies get into real estate investing to pursue financial independence, and going from single-family to multifamily investing can be a cheat code for reaching your financial goals even faster. Today’s guest had a goal of 50 rental units that she was able to achieve in just four years, and in this episode, she shares how she built her real estate portfolio so quickly!
Welcome back to the Real Estate Rookie podcast! Today, Jessie Dillon returns to the show to update us on her recent investments. Last time we spoke, Jessie had just closed on her fifth unit, but she has made huge strides since then—buying 33 units in the last year alone. How did she do it? Stay tuned and you’ll learn the keys to her rapid success, from the big pivot that helped her amass units faster to the real estate partnerships that have helped her buy bigger rental properties.
Jessie provides a clear roadmap that can take you from square one to achieving your long-term goals—maybe in as little as a few years. The best part? You can do it without a big bank account or any of the typical landlording headaches!
Ashley:Welcome to the Real Estate Rookie podcast where we break down the steps you need to get your first, second, or maybe even your fifth deal. I’m Ashley Kehr.
Tony:And I’m Tony j Robinson. And today we’re bringing back one of our favorite guests, Jesse Dillon. If you listen to her first episode, Jesse started investing in 2021 and has scaled her portfolio to over 50 doors in just a few short years.
Ashley:This time we’re digging deeper into exactly how Jesse went from rookie investor to managing long distant rentals, partnerships, and creative deals. And we’re going to find out what’s working right now in today’s market. Jesse, welcome to the show. Thank you so much for joining us.
Jessie:Yeah, thank you guys for having me back. I’m really excited to share everything that’s unfolded since my last episode.
Ashley:So last time we talked you were starting to build momentum. What has changed today and has really impacted you most about your investing strategy?
Jessie:Honestly, I think what has changed was really just waiting for divine timing to unfold was huge. I think getting in the rooms with the right people who were doing what I want to be doing is huge. Last time we talked, I think I had just gotten closed on my first larger multifamily, which to me was large. It was 13 units. That was the biggest deal I did so far. And just recently I closed on my 50th unit, which was my big scary goal. Last time we talked, I did take a long break in there. Congratulations. Thank you so much. I did have a long break in there when I was just kind of planting seeds and waiting for everything to come to fruition. But this year everything really kicked into gear and this year alone, I went from 17 to 50
Ashley:Units. Wow, that’s incredible. So during that timeframe, did you switch strategies at all or did you stay on course?
Jessie:I stayed so laser focused, and I feel like that is a mistake a lot of people make. I could not have been more specific about what I wanted to do. I had a really hyper specific buy box. I had really specific plans for how I was going to fund each property, how I was going to find each property, and I didn’t stray from that plan, and I think that’s what made it happen. I think if I got distracted trying to chase two rabbits, I would’ve caught neither.
Tony:Jesse, one follow-up question because I think that a lot of folks understand the idea of having a tight buy box and knowing exactly what it’s they want to go after, but as new investors, sometimes it’s difficult to know what the right buy box is. So how did you land on such a tight laser focused buy box approach for yourself to say like, okay, this is actually what I need to be focusing on?
Jessie:Well, first, no buy box is wrong. I mean, any buying criteria can work. Anything can work if you buy, right? Any strategy works, any property you can make money on if you buy it right and manage the investment properly. But I knew that I wanted to set myself up so that I had $15,000 coming in per month in true net cashflow at some point within the next couple years. And working backwards, well, I knew, okay, I can find a deal that will cashflow $500 per month per unit if I buy value add multifamily, and if I’m buying in partnerships, I’m going to walk away with half of that. So I worked it out to say, okay, I need about 50 units, and I didn’t want to have to do that across 25 duplexes. That just seemed like so much work. So I figured, okay, I want to do it across more like four transactions and I want to work one-on-one with people because that I think would feel the best. So then I figured, well, to buy a 10 to 15 unit property in a one-on-one, 50 50 partnership, I need capital partners who have X amount of startup capital. So I really narrowed down that buy box by figuring out, well, what’s my end game and how do I want to get there? What’s going to be the path of least resistance to get there?
Tony:Man, I love that breakdown. And what a just simple approach to saying, okay, what are my goals? What kind of property is going to help me get there? And then what do I need to get those types of properties? I think a lot of times we hear the word buy box and we feel that maybe it has to be externally influenced, which I think to a degree it should be because I can have a buy box that works maybe in California, but it’s not going to work in Buffalo and vice versa, what Ashley looks for in Buffalo. I might not get here in California. But I think the idea of making sure your buy box actually supports your goals is the bigger thing to focus on because so many people that talk about the doors, but you talked about, Hey, I want X dollars month in cashflow and what’s the best, most efficient way for me to get there? And I think that’s the approach more Ricky should be taking.
Jessie:Yeah, I feel like beginning with the end in mind is the most important piece because a lot of people I’ve noticed are pursuing these strategies that really aren’t even in line with what they want their life to look like in a couple years. I know I could get to my cashflow goal quicker if I did short-term rentals maybe, but that’s just not the type of work that I envision myself doing, so I’m not going to start there if I don’t want to end there.
Ashley:So that was one decision that you made that kind of had an impact on your growth. Was there anything else that you’ve changed or maybe done differently than other investors trying to grow and scale?
Jessie:I think the biggest thing was just sticking it out even when it seemed like it wasn’t really working. So I had a whole list of things drawn up of here’s what I’m going to do daily, weekly, monthly, quarterly to try to attract to the perfect capital partner. And I was just plugging away for a couple years at doing all those things, putting the work in, even when it kind of seemed like it wasn’t working and things weren’t coming together. I knew I was planting the seeds were going to eventually come to fruition. So I think just sticking it out was probably the biggest thing that I did that I noticed some investors don’t do. I feel like a lot of times if something doesn’t work within maybe two months, you just get fed up and you switch to a different plan, but it often does just take time. You have to put the work in and then just sort of let it marinate.
Tony:And Jesse, as you think about the things that you actually did, you said you had this plan of like, Hey, here are the things I’m going to focus on. What would be your advice to Ricky’s? What are those core actions that you feel that you did over that timeframe to lay those seeds lay the foundation for you to be able to scale so quickly?
Jessie:Yeah, so this is going to be super tangible how to, so if your goal is to find capital partners, which mine was and it no longer is now, so I’m not doing this set of things anymore, but when I was looking for the right capital partner, I got really clear on what the right capital partner is for me because it’s different for everyone. I literally made this character in my head of who would be the perfect person for me personally to work with. And I posted on social media every single week, at least a couple times about what I was doing in real estate. I created an email newsletter that I sent an email to once a month, even if I felt like I didn’t have that much to talk about. I just figured something out, like everything you’re doing is content. Everything is something somebody is interested in.
Jessie:I spoke at local meetups. I went to all the local meetups. I applied for different real estate podcasts. I also did something, the scariest thing was I texted a list of 50 people that I made, and it was a list of people who I thought they are probably friends with or know that ideal capital partner that I made up in my head. So I texted those 50 people. I texted five a day for 10 days and it was super uncomfortable, and I just said, Hey, we follow each other online, so I’m sure you’ve seen what I’ve been doing with real estate. This is what I’m looking to do next. I’m looking for someone who X, Y, Z. If you happen to know anyone or think of anyone that is interested in that, will you just share my info with them? So I wasn’t directly asking them, I was asking them for a referral, and the text was written in a way where if they don’t feel comfortable even responding, they don’t have to. And one of my partners came from those texts, and today we have over a million dollars of equity in our property. So today that was a half a million dollar text that I had sent, and within a couple of years, it’ll easily be a million dollar text for me. And it was uncomfortable. Most people did not text me back, and that’s okay, but I only needed that one response. So yeah, the list is a lot of just like what can I do today to put out there and tell more people what I’m doing?
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Jessie:That’s different for everyone. I know for me personally as the person who wants to be doing the work, I want to be the active partner. That’s how I’m earning my half of the deal. I like someone who’s not really going to micromanage what I’m doing on my end. And part of that is I’ve laid out this track record on social media, so people already have been watching what I’m doing. I already built trust with them that way. So that I think helps to set the stage for not being micromanaged, just to reiterate the importance of sharing what you’re doing online. But I knew that I wanted someone who wouldn’t really micromanage me. I knew that I wanted someone who had X amount of capital ready to deploy because that is what we needed to buy a 10 to 15 unit value add multi. And I knew that I needed someone who that wasn’t going to feel like a stretch for them to invest that much.
Jessie:I didn’t want them to feel like they were investing their last dollar. I also knew I wanted someone who they really didn’t need to get that capital back for at least 10 years. So they weren’t on a short timeline. So it’s really important to, you don’t want to jump when someone’s interested in partnering with you. You want to really feel each other out. It takes multiple phone calls or zoom calls or coffee meetings to really figure out if you want to enter this business marriage with someone and it should feel like a win-win for both people. I think that’s the best partnership where you each feel like you’re almost kind of getting too good of a deal. And all of my partnerships have felt that way and I probably just would not enter one that didn’t. I have almost entered partnerships that I sort of had iffy intuitive feelings about, and my intuition was right in the end. And those were really good lessons. And fortunately, none of those potential partnerships went on to buy properties. But you have to have a really good gut feeling about it, and I think you have to both feel like you’re getting the good end of the deal.
Tony:You bring up a really good point, Justin. I don’t want rookies to overlook this, but we’re talking about being able to say no to certain people, but I feel for most rookies, that’s not even the challenge that they’re facing. The bigger challenge is how do I even get people to say yes? And we talked about this right before the breaks, but I don’t want to gloss over it, but you did an insane amount of work to build up the pool of people that you could potentially reach out to. You said you were posting consistently on social media, you were going to local meetups, participating in those meetups, you were having coffee with people, reaching out to folks that you were meeting, you were doing all of the work that I think a lot of folks aren’t willing to do to start building that pool of people because if you’re like most rookie real estate investors, you probably don’t have a lot of folks in your network currently who could just fund your deals. But it’s like how do you go about building that network and adding people to it? And that’s the part that I don’t want Ricky to gloss over because you did a lot of work, a lot of work to build that pool of people.
Jessie:And to your point, nothing happened for two years. So there was a lot of work that felt like there were multiple times that I was sitting on my back deck crying, being like, I’m doing all the things. I know I’m doing the right stuff. Why is nothing working out? Why is nothing panning out? And it turned out that in this time where it felt like nothing was working and it made no sense that I was putting in all the work and just nothing was happening, it turned out that so many changes in my personal life were ahead of me that were going to require my attention. So I feel like it was divine timing that nothing was playing out yet. I was planting all the seeds but nothing panned out. Then I really had to take my foot off the gas and focus on my personal life for a little bit.
Jessie:And then the second I felt like I was ready to really refocus on work, which was fall 2024, immediately everything fell in line. And then I had 17 units. I was really pushing for 50 and February, 2025, I closed on an eight unit. June, 2025, I closed on a 13. July, 2025, I closed on a 12 unit. So everything happened all at once, even though I had been putting in all this thankless work for a couple years to get there. And I feel like you don’t see that part. You only see online once everything works out, but you don’t see all the crying on the back deck and putting in two years of work for nothing. So I think it’s just important to note that if you really stick it out, it will come together in divine timing.
Ashley:So along with getting creative with partners. And what about sourcing the deals? How have you been able to be creative finding these off market deals?
Jessie:So very few of these deals were off market. I feel like everyone says LoopNet is where deals go to die. I do not believe in that. I have found almost all my deals through agents, and once you’re tapped into a market, once you’re actively every week reaching out to the same couple agents or brokerages and saying as a reminder, here’s my buy box, please let me know if you have anything you want to do that weekly when you’re in buying mode because you want them to think of you first. So the last few deals were pocket listings, which is great, but I have done the off market lead generation stuff. I got an amazing wholesale deal that way, but I do kind of feel like a lot of people bend over backwards trying to find an off-market or creative deal when there are tons of on-market deals that are really good that you can get today instead of holding out for a year or two years or three years chasing this unicorn creative, no money down deal. So yeah, I would just encourage people look on and you can offer whatever you want. The asking price is just the asking price. I have not paid the asking price for anything. You can offer anything. You can offer whatever you want. So I’ve actually gotten pretty substantial discounts on properties just by offering less and explaining why with the current rates, that’s really the only number that a bank will agree with.
Ashley:And can you explain what a pocket listing is? Because I feel like that’s kind of like the gray area of off market, but not technically on market yet what a pocket listing is for everyone because that is a creative way to get deals.
Jessie:So a pocket listing is like if I was a seller and I approached my agent and I was like, I do want to sell this property. I’m ready to go. Here’s all the financials. And the agent will start to get the info packet ready or the offering memorandum with all the information, but they won’t post it online anywhere yet. They might just kind of share it with a couple qualified buyers that they already know would be interested in it, but it’s not really public knowledge yet that it’s for sale. So that would be a pocket listing. It would likely get posted in maybe a month or so afterwards if none of those kind of secret VIP buyers are interested.
Tony:So Jesse, as you continue to scale, you are finding deals on market mostly, which I think is a good sign for a lot of rookie investors because finding good deals is sometimes the hardest part of the job, but I think you’re giving ’em hope that we can find good deals on market. But I think one of the questions that might be popping in the minds of our listeners is you’re finding the deals, you’re finding the money partners, but how are you actually structuring these partnerships in a way that’s enticing for both you? Because you’re doing all the work of finding the deal, I’m assuming managing it all the day to day, but also for the folks that are bringing the capital. What structure have you found to be best?
Jessie:Yeah, so I mean I think the best structure is whatever feels right for you honestly. But what I personally do is we create a trust together and we are equal beneficiaries of that trust. And my partner’s role is to bring the startup costs, so the down payment, closing costs and reserves. Normally we get closing costs covered by the seller, so that cuts down on that. And they also have to approve expenses over $5,000. And my job is pretty much everything else. Find the deal, vet the deal, negotiate, get under contract, manage closing, and then I’m managing the property manager. So because it’s five units and up, the commercial lender is going to require that we have a property manager anyway. So even if I wanted to manage long distance, I can’t. We need to have a management company and I’m grateful that mine is amazing, but it’s really important that I’m the asset manager. I still have to know what’s going on. So I have a really close relationship with my property manager. So we split equity and cashflow 50 50, and we go into it expecting to not take a distribution for the first couple years because we want to make sure we don’t have to put more money into it and buying value add. We’re walking into something where maybe there’s non-payment issues, maybe there’s vacancy or deferred maintenance or really, really low rents. So it’s kind of a rocky road to just get it started.
Jessie:And I will say I have presented that setup to tons of potential partners who were like, that sounds like an awful deal for me. And I’m like, yeah, if you are also willing to do the work and you have the knowledge and experience required to do the work as well as bringing the money, of course it wouldn’t seem like a great deal to you. But for my ideal capital partner, it’s someone who has the capital, but they don’t even want to have to learn all of this. They don’t want to ever be on the phone with a property manager. They don’t want to do the work, they don’t want to learn how to do it. Or I actually have a couple partners who they do have time, but they haven’t done a deal this size before and they want to partner up just because it’s less scary to not be the only one in it. So yeah, no matter how you set it up, I think there will be people who don’t feel like it’s a great deal if they don’t need what you are bringing to the table.
Ashley:Now that you’ve grown and scaled to these different partners and more and more properties to your portfolios, how have you needed to get creative with your systems to be able to scale and grow without feeling that burnout or that you’re overwhelmed, especially going from 17 to 50 units in one year?
Jessie:And by the way, I still have my salon business. I’m here right now and I still work in that business two or three days a week. So I think my life sounds a lot more hectic than it is because I’ve always had one if not more really great assistance. My main va, she’s really more of a virtual executive assistant. She’s fully remote. She’s been with me since 2018, but we’ve worked together long before that. She, I think, makes most of it possible. And right now I also have one other assistant who does slightly simpler work and sort of works under her. And I also use monday.com just to track all of my tasks and keep everything organized for us. So every Monday morning I go into monday.com and I make my list of what I have to do that week. I star what’s most important, and I’m also addicted to the Reminders app on my phone, so stuff that’s time sensitive, I’ll use that.
Ashley:So Jesse, if somebody is looking to maybe get their own help or to hire someone for the first time in their real estate business, what are some of the tasks that you have your assistant do for you that kind of takes some of the workload off your plate?
Jessie:Oh, big ones would be Instagram engagement. There’s a lot of social media stuff that they help with. And Instagram engagement refers to seeking out your ideal, for example, capital partner or whomever, whoever you’re trying to connect with, seeking out those accounts and engaging with their content. So I’ll have my assistants do 30 minutes a day doing that also with bookkeeping. So there’s a lot of reoccurring bookkeeping tasks that I can easily explain in a 15 minute loom video how to do it, and then just pass that off. Anything that’s repeatable, like anything that you’re doing every day, week, month that doesn’t require your face or your voice can usually be offloaded. And it does take time upfront to teach someone how to do those things, but not as much as you would think. And it also frees up mental space that you can use to instead analyze deals, which is something that really only you can be doing at the beginning.
Ashley:And one thing rookies could be doing now is actually creating the Loom video, or there’s like tango. There’s other different ways to kind of capture what you’re doing, capture the process and turn it into an SOPA standard operating procedure. So even if you’re not ready to hire someone now down the road, you already have it documented. One of the mistakes that I made was waiting until I was overwhelmed hiring someone to help me, and then I had to stop pause to actually document everything I needed them to do and train them. So if you have your first property, document everything you’re doing, including paying the water bill, how you communicate with your tenants, every little thing so that it’s so much easier when you are ready to actually hire someone and to have them help you. Now I want to transition here to your long distance investing. So Jesse, you have bought some properties that are local to you, but you also started investing long distance. What made you decide to make this pivot and what markets have you landed on?
Jessie:Yeah, I’m in central Massachusetts. My first couple properties were local, one was two hours away, but I still consider that local in New England. After that was when I started working with my first capital partner. We wanted to do a bigger deal. We had a specific cashflow goal, and locally, the only way that on market deals were going to make sense was if we got them with partial or full creative financing. And there was a million people in line behind me offering who were perfectly happy to use conventional financing and just get a first base hit where I was trying to make everything a home run. So we were making offers on stuff like that for probably six months. And finally I was like, you know what? If we have to have a management company anyways because of the size of these deals, there’s really no need for it to be in our backyards.
Jessie:There’s no need and I have the flexibility to travel to, so we don’t really have to do something around here. And we already know that the numbers around us are not as good as the numbers would be in say, the Midwest. So we looked at a couple different cities in the Midwest. One of them was Chicago, and we were just looking at job diversity, money being reinvested in the community. We looked at the price to rent ratio. A lot of people wouldn’t think to go to Illinois because it is a tenant friendly state, but that’s where we were offering anyways. Massachusetts is very much a tenant friendly state, so there was nothing different for us there. But we were looking at the price of properties and we’re like, the numbers are just so much better. Even the crappiest most looked over on market deal looks so much better than the stuff that we were looking at in Massachusetts. So it was on a Friday that together we decided we’re going to pursue properties in Chicago, and we were under contract by the end of the weekend after six months of just banging my head against the wall offering around here. And yeah, I’ve never looked back. I actually love owning long distance because I think of the properties more so like a business and I don’t get caught up constantly wanting to drive by and get anxious about this or that. And that also frees me up to really focus on scaling.
Tony:Jesse, let me, what you said was pretty phenomenal. So you guys made the decision to invest in an entirely new market on Friday and had a property under contract by the end of the weekend. So we’re talking in the span of 72 hours. You went from decision to property found to under contract, which is insane. What allowed you guys to move so quickly and with so much confidence in a market you had never invested in before?
Jessie:I think it was a lot of Googling and a lot of calling around. It helps that me and this partner we’re both equally aggressive and just confident in the overall plan and confident in each other. I think an issue a lot of people run into is if you’re working with a partner and you ideally want to go at different speeds or you have different risk tolerance, that can be kind of like a point of friction. But we didn’t have this issue. We were rearing to go and I just called around to a bunch of different brokerages. I talked to as many people as I could just about the overall market and what my plan was. And from going to events like BP Con and just being in online networking groups, I did actually already meet a couple people who are investors who live in that area. So I talked to them as well. And yeah, we just felt really good about it. One person connects you to the next, so when I found a realtor I really loved, he connected me to the first lender I worked with and the attorney that I continue to work with who I love. And one person, once you get one really good person on your long distance team, they will connect you to all the other people that you need.
Tony:I think it goes back to the point you made earlier about laying the foundation and then being able to move quickly when the opportunity presents itself. It’s like it sounds crazy to say like, Hey, we decided on Friday and then we’re under contract on Sunday. But then when you explain it, there is a lot of legwork you’d already done to give you that confidence. You had been building your network, you knew folks who were already investing in that market who could be a sounding board for you. You did all the work of calling the brokers and doing your due diligence and understanding the tenant landlord laws of that state. So I think we sensationalized the speed at which you were able to move, but we under sensationalized the work that allowed you to move at that speed. And I think that’s the part that I want Ricks to understand is that there was a lot of legwork that went into getting you ready to move that quickly. For a lot of rookies that are maybe nervous, Jesse about long distance deals, what’s one thing they can do this week to start getting comfortable with that idea of investing outside of their own backyard?
Jessie:I think I would list out all the worst case scenarios and then for each one, map out what you would do in that case because there’s always a way to fix every problem, and the worst case scenario really is never that bad. And it’s truthfully stuff that could happen even if you invested in your own backyard too. And also just start making calls. Just start having phone calls with property management companies in the area that you’re considering working in. Start having phone calls with agents who have a lot of properties listed what you would go for and just start talking to people, even if you’re not comfortable yet with actually offering on something, just start having three conversations a day with people who would potentially be on your team. You can even go on BiggerPockets and just find other investors in that market who live and invest there and just message them, message five people a day. Just having conversations is a very low risk way to start getting direction.
Ashley:Well, Jesse, we have to take our last ad break, but when we come back, I want to talk about the asset management piece of your properties and what your future plans are. We’ll be our back. Okay. Welcome back. We are here with Jesse. So Jesse, as you’ve grown and scaled, you have outsourced the property management to property management companies and you have become the asset manager. Can you kind of break down what is different between those two roles?
Jessie:Yeah, so as an asset manager, you’re not really ever going to have conversations with tenants. You probably will have very limited contact with contractors. The property manager is kind of a layer between you and all of the day to day, a layer between you and most of the people you would ever have to talk to if you’re self-managing. So my role essentially is to meet with the property manager. Generally, I feel like at the very beginning when we first get a new property, we’ll be talking every couple days about something, whether we’re texting or emailing or on the phone. And now I’m down to just a very thorough check-in for each property via email once a month. So those check-ins will be about vacancies, any large balances like of overdue rent, tenants who are on payment plans, repairs and maintenance. So we have a whole spreadsheet for each property on everything that came up in the inspection and we mark off what’s an urgent safety issue or what can maybe wait.
Jessie:So we’ll work through that together and work together to prioritize it too. So that’s what my role looks like and I actually, I know that especially when cashflow is important to you is usually the best move. But I know that I just do not want self-management to be part of my ultimate plan. So I’m not going to start now and then have to make that transition later. I’d rather have my time be spent scaling my portfolio rather than managing the day-to-day stuff. And I do think that a lot of times when you hire a property manager, you really take your foot off the gas, you don’t have a pulse of what’s going on, and that’s where a lot of people make the mistake. You really have to also know everything going on in your properties and keep a close eye on what’s happening, what’s vacant, is it being marketed? Have we dropped the price if we need to, stuff like that. So that’s kind of my role is basically overseeing everything now.
Ashley:And Jesse, that’s a mistake I made when I outsourced the property management. I was like, this weight is off my shoulders. I feel so much relief, set it and forget it. And that was the wrong attitude to have so many things started to come up and then all of a sudden I was backtracking for three months and it’s like, oh my gosh, this happened that happened. You need to be on top of it. And there was an instance where an apartment didn’t even get rented. They moved someone out and then it just sat vacant. It was just like, oh, sorry. There was a miscommunication between the maintenance team and the leasing team and it never got listed. And that was like three months this property sat vacant. So just things like that. There’s a lot of things. Nobody’s going to care for your property as much as you do, and there are ways to outsource, but I think always having that oversight and just making sure everything is done because people do make mistakes or systems aren’t run as effectively as you would like them to be. So asset management is such a key role to being a real estate investor or even having somebody in that position who is the asset manager looking over all of these moving pieces.
Tony:I was just to add onto that the only ways to invest in real estate that I think are truly, truly passive are being a limited partner into syndication. Because once you do your due diligence upfront on the deal and the operator now you legally literally have no control over what they do and how they operate. You’re handing your money over to them, letting the Mexican execute and everything. That’s a truly passive investment. Or if you’re doing something like your note investing where you are giving private money to other individuals who are then using it to go out there and flip or buy properties and bur and you’re just collecting interests on your money. So the way to kind of passively invest in those deals, but aside from LPs or being a node investor, every other type of investing involves some sort of active involvement to make sure that things are going according to plan. And I think that’s a piece that sometimes rookies underestimate is that even if you have a pm, you still got to jump in and hold that PM accountable.
Ashley:Jesse, before we wrap up here, looking forward into the end of this year and into 2026, is there any opportunity out there that you think maybe rookie investors are missing or need to start doing the research on and looking into going forward?
Jessie:Oh God, I don’t know. I mean, I feel like there are definitely, there’s a lot of buzz online about moving away from this strategy, maybe getting into this strategy. And I don’t know that riding the waves of that is the most productive thing. I feel like especially if you’re at the beginning of your journey, that can just be so distracting and keep you from ever actually moving forward. I think it’s really best for each person to focus on what strategies truly align with what they want their life to look like in a couple years. And that’s going to be totally irrelevant to whatever market shifts are happening or whatever strategy’s trending or what people on Instagram are doing. So I got to say, I honestly kind of block all that stuff out because it definitely very quickly takes me away from my laser focus if I start to watch what other people are doing and read the emails about that stuff.
Jessie:But that said, as much as I’ve been laser focused on my value add multifamily, I accomplished what I wanted to with that, the 50 units was my big thing. So I know that now in a couple of years, once everything starts ramping up, I’ll be at that cashflow goal that I wanted to be at. But that said, my portfolio is very delayed gratification heavy right now. It’s very equity heavy. And I want to now shift into a little more short-term cashflow. So me and one of my business partners who I closed on my most recent deal with, we actually are offering on self-storage right now, which is also in line with both of our small business experience. And we’ll be able to just get it cash flowing a little sooner than we could value add multi. So I actually am in the middle of a pivot right now.
Ashley:Cool. Well, we’re going to have to have you back again to talk about self storage in a couple more years. Well, Jesse, thank you so much for taking the time to join us today. Can you let everyone know where they can reach out to you and find out more information?
Jessie:Yes. On Instagram, I’m Jesse Dillon with an underscore at the end.
Ashley:Okay, great. Thank you so much. Well, everyone, I hope enjoyed today’s episode. If you’re not already, make sure you’re subscribed to our YouTube channel at BiggerPockets or is it that one at realestate Rookie? Yeah. Okay. Make sure you are subscribed to our YouTube channel at realestate Rookie, and you can also find us on Instagram at BiggerPockets rookie. I’m Ashley at Wealth from Rentals, and he’s Tony at Tony j Robinson on Instagram. And we’ll see you guys next time. Thanks so much for joining us.
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