Zero to 50 Units in 4 Years (Financial Independence Cheat Code)

0:00Ashley Kehr: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.

0:13Ashley Kehr:I'm Ashley Kehr.

0:14Tony J. Robinson:And I'm Tony J. Robinson. And today we're bringing back one of our favorite guests, Jessie Dillon. If you listened 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.

0:27Ashley Kehr: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. Yeah, thank you guys for having me back. I'm really excited to share everything that's unfolded since my last episode. 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? Honestly, I think what has changed was really just waiting for divine timing to unfold was huge.

1:08I 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 um 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

1:51Ashley Kehr:Wow, that's incredible. So during that timeframe, did you switch strategies at all or did you stay on course? 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.

2:25Tony J. Robinson: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? 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.

3:00But 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$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.

3:47So 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?

4:09Tony J. Robinson: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 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 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 a month in cashflow.

4:48Tony J. Robinson: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. 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 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.

5:16Ashley Kehr: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? 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 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.

5:55I 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. You have to put the work in and then just sort of let it marinate.

6:20Tony J. Robinson: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 rookies? 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? Yeah, so this is gonna 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.

6:57I 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. 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 different real estate podcasts. I also did something. The scariest thing was I texted a list of 50 people that I made.

7:42And 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, 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.

8:18And 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 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 myself out there and tell more people what I'm doing?

8:57Tony J. Robinson:Do you ever notice how every passive investment somehow turns into a very active lifestyle, active spreadsheets, active phone calls, active stress? Here's a better question. What if you could buy brand new construction homes, 10 % below market value in the best markets across the country without making real estate your second job. That's exactly what Rent to Retirement does. They're a full-service, turnkey investment company handling everything for you. In some cases, investors get 50 % to 75 % of their down payment back at closing, plus interest rates as low as 3.75%. They've partnered with BiggerPockets for over a decade, helping thousands invest smarter.

9:34Tony J. Robinson:If you want to do the same, visit biggerpockets.com slash retirement to learn more. Most banks will give you a line on your primary residence and stop there. Avon looks to underwrite the equity in your investment property, the second home you have, the property you hold in your own name, and put a line of credit against it on a Visa card. Same asset, same logic. Think about what this unlocks. Earnest money, the day a deal hits the MLS. A contractor, paid on Friday instead of next month. High rate balances you are already carrying refinanced onto a line secured by equity you own, all at a fraction of the cost.

10:12Tony J. Robinson:With AVEN, you can check your offer at no cost with no impact to your credit score. There are no hidden fees, and because you own a home, you qualify for a rate that credit cards simply cannot offer. AVEN has a 4.9-star Trustpilot rating from over 8 ,000 verified customers. If you own property and you're financing your next move on an unsecured card or expensive short-term debt, you are overpaying for capital. Avon fixes that. Go to avon.com to discover your offer. Stop overpaying for capital. Avon accounts are arranged by Avon Financial, Inc., NMLS number 204-2345. Avon accounts are issued and held by Coastal Community Bank, member FDIC, equal housing lender, and MLS number 462-289.

10:59Tony J. Robinson:Avon cards are issued pursuant to a license from Visa USA, Inc. terms and conditions apply, subject to credit and property approval, eligibility and availability vary by state and property type. Here's why savvy real estate investors are obsessed with bonus depreciation. It lets you take that rental property or commercial building you own and depreciate most of the cost against your income, legally 100 % IRS compliant. That's instant cash flow improvement. Cost segregation, guys, is the number one firm nationwide, specializing in identifying these faster depreciating assets in your property. They've completed tens of thousands of studies across all 50 states from remote cabins to apartment complexes.

11:40Tony J. Robinson:So if you own investment property, this is a no brainer. So visit costsegregationguys.com slash BP for your free proposal and find out how much you could save this tax season.

11:51Ashley Kehr:Today's show is sponsored by Baseline. They say real estate investing is passive, but let's get real. Chasing rents, drowning in receipts, and getting buried in spreadsheets feels anything but passive. If you're tired of losing valuable hours on financial busy work, I've found a solution that will transform your business. It's Baseline, a trusted BP Pro partner. Baseline is an all-in-one platform that can help you automate the day-to-day. It automates your rent collection and uses AI-powered bookkeeping to auto-tag transactions for instant cash flow, visibility, and reporting. Plus, they have tons of other features like recurring payments, multi-user access, and free wires to save you more time and money.

12:33Ashley Kehr:Spend less managing your money and more time growing your portfolio. Ready to automate the busy work and get back to investing? Baseline is giving BiggerPockets listeners an exclusive$100 bonus when you sign up at baseline.com slash biggerpockets. So one thing we've learned about you is that you've successfully used JV partnerships on multiple deals, what advice would you give rookies about finding the right partner? You mentioned sending out the text, but just because somebody responds and says, yes, I'm up for it, what actually makes a good partner? 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.

13:15That'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.

13:55And 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 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 business marriage with someone.

14:32And 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 yeah, 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.

15:12Tony J. Robinson: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 break, 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 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.

15:52Because if you're like most rookie real estate investors, you probably don't have a lot

15:57Tony J. Robinson:of folks in your network currently who could just fund your deals, right? 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 with people. Yeah. 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 and then the second I felt like I was ready to really refocus on work which was fall 2024, immediately everything fell in line.

17:09And 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.

17:49Ashley Kehr:So along with good and creative with partners and what about sourcing the deals? How have you been able to be creative finding these off market deals? 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.

18:29So 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.

19:12You 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.

19:26Ashley Kehr: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. 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 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.

20:08So that would be a pocket listing. It would likely get posted in maybe a month or so afterwards, if none of those kind of like secret VIP buyers are interested.

20:19Tony J. Robinson: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 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, 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.

20:51Tony J. Robinson:What structure have you found to be best? 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.

21:29So 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 cash flow 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, 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.

22:18So 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.