← Real Estate Rookie
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- [00:00]
A
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 Kerr.
- [00:14]
B
And I'm Tony J. Robinson. And today we're bringing back one of our favorite guests, Jessie Dillon. If you listen to her first episode, you know, Jessie started investing in 2021 and has scaled her portfolio to over 50 doors in just a few short years.
- [00:28]
A
This time we're digging deeper into exactly how Jesse went from rookie investor to managing long distance 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.
- [00:44]
C
Yeah, thank you guys for having me back. I'm really excited to share everything that's unfolded since my last episode.
- [00:50]
A
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?
- [01:00]
C
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 are 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. 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 units.
- [01:52]
A
Wow, that's incredible. So, so during that time frame, did you switch strategies at all or did you stay on course?
- [01:59]
C
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 have caught neither.
- [02:25]
B
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 is 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?
- [02:46]
C
Well, first, no, buy box is wrong. I mean any, 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 you know, 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 cash flow at some point within the next couple years. And working backwards, well, I knew, okay, I can find a deal that will cash flow dollars 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?
- [04:09]
B
Man, I love that breakdown. And what a just like 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, we hear the word buy box and we feel that maybe it has to be like externally influenced, which I think to a degree it should be, you know, like, because I can have a buy box that works maybe in California, but it's not going to work in Buffalo, you know, and like vice versa, like what actually 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 per month in cash flow and you know, what's the best, most efficient way for me to get there. And I think that's the approach more Ricky should be taking.
- [04:53]
C
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. Like, I know I could get to my cash flow 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.
- [05:17]
A
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?
- [05:29]
C
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 the perfect capital 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 that 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. Like you have to put the work in and then just sort of let it marinate, you know?
- [06:21]
B
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 like, what are those core actions that you feel that you did over that timeframe, to quote, unquote, lay those seeds, you know, lay the foundation for you to be able to scale so quickly.
- [06:35]
C
Yeah. So this is going to be like 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, like, 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's interested in. I spoke at local meetups, I went to all the local meetups. I applied for, you know, 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, 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, you know, 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 xyz. 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 $1 million 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 te. 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 myself out there and tell more people what I'm doing?
- [08:58]
D
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- [10:05]
D
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- [10:43]
A
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- [12:00]
C
Different for everyone I know. For me personally as the person who wants to be doing the work like 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 kind of have been watching what I'm doing. I already sort of 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, you know, 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. I didn't want them to feel like they were investing their last dollar. I also knew I wanted someone who, 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 know, 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 like 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 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. Unfortunately, none of those potential partnerships went on to buy properties. But yeah, you have to have a really good gut feeling about it. And I think you have to both feel like you're getting, you know, the good end of the deal.
- [14:04]
B
You bring up a really good point, Justin. I don't want rookies to overlook this, but we're talking about like 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. You were, you know, reaching out to folks that you were. 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. Right. But it's like, how do you go. 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.
- [15:03]
C
Yeah. And to your point, like, nothing happened for, like, two years. So there was a lot of work that felt like. 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. Like, why is nothing working out? Why is nothing panning out? And it turned out that, you know, 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. 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, you know, 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 like you only see online once everything works out, but you don't see all the crying on the back deck and putting in, you know, two years of work for nothing. So I think it's just important to note that, that, you know, if you really stick it out, it will come together in divine timing.
- [16:42]
A
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.
- [16:52]
C
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, you know, once you're tapped into a market, once you're actively like every week reaching out to the same couple agents or brokerages and saying, you know, as a reminder, here's my buy box. Like, 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, you know, 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 know, 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.
- [18:18]
A
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.
- [18:32]
C
Yeah. 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. 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 or so afterwards if none of those kind of like secret VIP buyers are interested.
- [19:11]
B
So, Jesse, as you continue to scale, right, you're finding deals on market mostly, which I think is a good sign for a lot of rookie investors because, you know, finding good deals is sometimes the hardest part of the job. But I think you're giving them hope that, that we can find good deals on market. But I think one of the questions that might be popping 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, you know, 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?
- [19:45]
C
Yeah, so I mean, I think the best structure is whatever feels right for you, honestly. But what I personally do is a, 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 you know, 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 cash flow 5050 and we go into it expecting to not take a distribution for the first couple of years because we want to make sure we don't have to put more money into it and buying value add, you know, 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. 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're also willing to do the work and you have the knowledge and experience required to do the work as well as bringing the money. Yeah, 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're bringing to the table.
- [22:14]
A
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?
- [22:34]
C
Yeah, 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 assistants. My main va, she's really more of like a virtual executive assistant. She's fully remote. She's been with me since, like, 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, like, 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, 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, like, addicted to the Reminders app on my phone. So stuff that's time sensitive, I'll use that.
- [23:33]
A
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 take some of the workload off your plate?
- [23:47]
C
Oh, big ones would be like Instagram engagement. Like, 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 like 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, you know, analyze deals, which is something that really only you can be doing at the beginning.
- [24:48]
A
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 sop, a 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 like 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 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?
- [25:50]
C
Yeah, so I'm in central Massachusetts. My first couple properties were local. One was like two hours away, but I still consider that local in New England. And after that was when I started working with my first capital partner. We wanted to do a bigger deal. We had a specific cash flow 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. There's no need. And I have the flexibility to travel too. So like 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, like 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. So. 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, you know, constantly wanting to drive by and get anxious about this or that. And that also frees me up to really focus scaling.
- [28:09]
B
Jesse, let me. What you said was pretty phenomenal. So you, 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?
- [28:34]
C
I think it was a lot of googling and a lot of calling around. It helps that me and this partner were 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 like 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 bpcon 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 like, when I found a realtor I really loved, you know, he connected me to the first lender I worked with and the, the attorney that I continue to work with, who I love. And, you know, one person, once you get one really good person on your long distance, will connect you to all the other people that you need.
- [29:47]
B
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 we're under contract on, you know, Sunday. But then when you explain it, there is a lot of legwork you had already done to give you that confidence. You had been building your network. You knew folks who are 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 rookies to understand, is that there's 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?
- [30:40]
C
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, like 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 bigger pockets 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 like a very low risk way to start getting traction.
- [31:38]
A
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.
- [31:48]
D
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- [32:22]
E
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- [32:52]
D
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- [33:30]
E
Starting your own business can be intimidating because of all the hats you suddenly have to wear. There's the marketing hat for emails and social posts, the web designer hat for your storefront, the copywriter hat, the logistics hat, and of course, the hat hat just for tracking all the other hats. It's a lot, but the right tool to simplify it all. Total game changer for millions of businesses. That tool is Shopify. Shopify powers millions of businesses worldwide, including 10% of all US E commerce. From brands like Mattel and Gymshark to ones just starting out. Launch your store fast with beautiful templates that match your brand. Shopify's built in AI helps with content too, writing descriptions and headlines and even enhancing photos. Want to market like a pro? Create campaigns wherever your customers scroll. Best of all, Shopify is your expert partner, handling everything from inventory to shipping and returns. If you're ready to sell, you're ready for Shopify. Turn your big ideas into you. Get it. Sign up for your 1 month $1 per month trial period and start selling today at shopify.com bprookie go to shopify.com bprookIe shopify.com.
- [34:31]
D
I always felt I was some kind of superhero watching over my house, ready to jump in if anything went wrong. But one night I heard a noise. I woke up, totally didn't trip over my shoes in the dark, wearing my boxers, and then realized maybe I'm not really the crime fighting vigilante type. I might need something else to keep me safe. Like maybe an alarm system. But here's the thing. Most alarms, they're really reactive. They only go off after someone's already broken into your house. That's like locking the barn door after the horse has already escaped. That's why I switched to SimpliSafe. Their system is different because it's proactive. They have a feature called active guard outdoor protection where AI powered cameras don't just detect motion. They recognize when someone suspicious is lurking. Then real human agents get alerted right away. And they can talk through a speaker. They can flash lights, they can set off a siren, basically scare off the bad guys before anything happens. And if needed, they can even call the police right away. And with Simplisafe, there are no long contracts or hidden fees. Plus you can try it out risk free for 60 days. And one other thing, Simplisafe's been named the best home security system five years running by US News and World Report. Check them out at simplisafe.com pockets Again, that's simplisafe.com pockets there's no safe like Simplisafe.
- [35:44]
A
Okay, welcome back. We are here with Jesse. So Jesse, as you've grown and scaled, you have outsource 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?
- [36:02]
C
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 like 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, like when we first get a new property, we'll be talking, you know, every couple days about something, whether we're texting or emailing or on the phone. And now I'm down to just like a very thorough check in for each property, 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. So we'll kind of work through that together and work together to prioritize it too. So that's kind of what my role looks like. And I actually, you know, I know that self managing, especially when cash flow 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, like 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, you know, what's happening, what's vacant, is it being marketed, you know, have we dropped the price if we need to, stuff like that. So that's kind of my role is basically overseeing everything now.
- [38:08]
A
And Jesse, that's a mistake I made when I outsourced to property management. I was like, like oh, this weight is off my shoulders. I feel so much relief, like set it and forget it. And that was the wrong attitude to have. I, you know, like 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. Like you need to be on top of it. And like 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 an 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 is going to care for your property as much as you do. And there are ways to outsource, but I think like always having that oversight and just making sure everything is done because people do make. Make mistakes or systems aren't run the, you know, 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 as just.
- [39:18]
B
To add on to that, like, 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. Right? Like you're handing over there, you're handing your money over to them, them letting them execute on everything. Like that's a truly passive investment. Or if you're doing something like your note investing, where you're giving private money to other individuals who are then using it to go out there and flip or buy properties and burn and you're just collecting interest on your money. So the way that 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 planning. 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.
- [40:13]
A
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 their research on and looking into going forward?
- [40:30]
C
Oh, God, I don't know. I mean, I feel like there are. I feel like there are definitely a lot of. There's a lot of buzz online about, you know, moving away from this strategy, maybe getting into this strategy. And I don't know that like 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 strategy is truly aligned with what they want their life to look like in a couple years. And that's going to be totally irrelevant to like whatever market shifts are happening or like whatever strategy's trending or, you know, what people on Instagram are doing. So I gotta say, I honestly kind of like block all that stuff out because it definitely very quickly takes me away from, you know, my laser focus if I start to watch what other people are doing and, you know, read the emails about that stuff. But that said, as much as I've been laser focused on my value add multifamily, I accomplished what I wanted to with that. That was, you know, the 50 units was my big thing. So I know that now in a couple of years, like once everything starts ramping up, I'll be at that cash flow goal that I wanted to be at. But that said, my portfolio is very like delayed gratification heavy right now. It's like very equity heavy. And I want to now shift into a little more like short term cash flow. 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, you know, value add multi. So I actually am in the middle of a pivot right now.
- [42:22]
A
Cool. Well, we're going to have to have you back again to talk about self storage in a couple more years, so. 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?
- [42:35]
C
Yes. On Instagram. I'm Jesse Dylan with an underscore at the end.
- [42:39]
A
Okay, great. Thank you so much. Well, everyone, I hope enjoyed today's episode. If you're not already, make sure you subscribe to our YouTube channel at bigger Pockets or. Or is it that one at Real Estate Rookie. Yeah. Okay. Make sure you are subscribed to our YouTube channel at Real Estate Rookie. And you can also find us on Instagram at Bigger Pockets Rookie. I'm Ashley at Wealth from Rentals and He's Tony @TonyJRobinson on Instagram. And we'll see you guys next time. Thanks so much for joining us.
- [43:08]
D
Hey everyone, Dave here, host of the Bigger Pockets podcast. And my favorite event of the year is almost here, the Bigger Pockets conference. And I'm here with some exciting news that we just added two new sessions that you do not want to miss. First, we have Doug Bryan, super bowl champion turned real estate strategist who's going to share his playbook that he used after 2008 to scale to 17,000 single family units. And we have Andy Gill, full time investor and tech pro who's going to share the exact AI prompts he uses to save hours on contracts, deal analysis and operations. Said it before, but it's worth repeating. The next wave of opportunity in real estate is already forming and I believe that the investors who get ahead won't be the luckiest. They're going to be the ones who are the most prepared. That's why I want to see you at bpcon. With over 40 sessions packed with real tactics for today's market, you'll leave ready to act. But the real magic, it happens in the hallways. Connecting with other investors, swapping ideas and building relationships that last long after. Vegas. October 5th is right around the corner. So if you've been on the fence, now is the time to get your ticket. You can grab it@biggerpockets.com Vegas that's biggerpockets.com.
- [44:18]
F
Vegas yo, this is important, man. My favorite Lululemon shorts, the ones you got me back in the day. I think they're called pace breakers. The ones with all the pockets. I just got back from vacation and I left them in my hotel room. And dude, I need to replace these shorts. I wear them like three times a week. Could you send me the link to where you got them? Oh, also, my birthday is coming up soon, so. Anyways, thanks, bro.
- [44:39]
C
Talk soon.
- [44:40]
A
Looking for your newest? Go to's Lululemon what's New Gear drops on Tuesdays. Every Tuesday, head to lululemon.com to shop what's New Gear.