Rising From Ruin to Real Estate Tycoon: Jesse Trujillo’s $100 Million Journey #freedominvesting

Foreign. Hello there. Jenny Bolling here with Pivot to Prosperity brought to you by Pivotal Real Estate Investments where we helped investors build wealth and income through commercial real estate that also improves communities. And today we have Jesse to Hillio. Did I say that right?

Yes. That's close. Yep. And close.

I should practice first. I, I say this all the time. Thank you for coming though, Jesse. I would like to read your bio. You have quite the story and I think this will help to make things a little more concise as we talk through here. Jesse is a paradigm of resilience and determination. As a motivational speaker, real estate investor and the founder, CEO of all the Ajax. AJ AJ I want to say Ajax, Ajax companies. Jesse embodies the spirit of transforming his pain from profound adversity into profitable venture. His journey from bankruptcy and wrongful imprisonment to establishing an eight figure real estate investment empire within five years is not just inspiring, it's a treatment to the power of a testament. I'm sorry, to the power of unwavering perseverance and self belief. Speaking to crowds nationally, he shares insights on flipping pain to profit, embracing risks and the importance of determination and persistence in overcoming life's hurdles. As a residential, real estate and apartment investor, he has amassed over 788 doors in his rental portfolio with five within five years worth over $100 million in market value and has been instrumental in purchasing close to 1,000 flips and rental properties since 2010. His journey from a net worth of zero to over 15 million in a span of five years is nothing short of remarkable. True, true. Jesse's expertise isn't just in building wealth, it's in sharing it. Through AJX Capital, he aids busy professionals in creating passive income via recession resistant real estate investments. His approach is grounded in integrity, transparency and a deep commitment to delivering value with every investment. His knowledge in funding, structuring deals and project management makes him an invaluable partner. That's a great write up there, Jesse. So what were you thinking about as I was reading that? What would you like to say beyond this here?

You know, it just, it just, it's, it's about sharing my story and, and helping everyone realize that, you know, it's, it's. You just got to push yourself. Persevere. Right? Perseverance is, is, is huge and I hear that in my life and that's what's gotten me to where I'm at. Right. It's about not giving up and really pushing forward, you know, to make sure you just hit your goals and so.

You have Kids, I've. I've had the privilege of meeting your son. We were at an event here in, in Orlando.

So.

Yeah, tell us about your family and how that all worked. Worked the imprisonment part and all that is crazy. To come back from that so fast and to 0 to 15 million. Talk a little about that, would you?

Yeah, I mean, just really, I mean, overall, it was a long journey and it was something that kind of came unexpectedly. Right. We had sold some properties in 2008 and 2012. They're knocking on my door, arresting me and pretty much letting us know that we had two properties that we had sold, a lender had, that had bought them. He said he had some clients for them and ended up being stolen identities and we had no clue. But, you know, he had asked me for help on renting them without me knowing because they were going to do property management on them and that's how they included me.

Kind of guilty by association, pretty much.

100% and that's what it was, you know, and I was hopeful to kind of prove. Approved that obviously we had no connection in there because they were doing it in other counties in California. And then later we find out, you know, I hired an attorney, it was a friend of mine, and he was there to, you know, hopefully help me out. And he said he was, he could prove my innocence, no problem. That, don't worry, just keep working. Long story short, kind of comes back and, you know, he kind of pushes me into signing a plea because he said they were threatening to bring in some family members that were on, you know, that owned the properties with me at the time before we sold them, and, you know, said, but don't worry, well, you know, I'll prove your innocence. Long story short, get to the arraignment. And the judge, as much as he was questioning my decision to signing this plea, you know, looked at my attorney and he pretty much said, he nodded his head, that, yes, just keep moving forward. And I ended up. He ended up sentencing me at that moment to five years in prison. Kind of caught us off guard. Didn't. Didn't say goodbye to my kids, didn't say goodbye to my wife, didn't put any personal things in order. And we ended up finding out a couple months later that. That this attorney was. Was actually money laundering for the Mexican Mafia. And he got arrested and he ended up going to federal prison for five years. This is all during the time that he was supposed to be working on my case. So put a lot of trust in him and we ended up getting Duped, so kind of ended up going to prison for, for, for not the right reasons, you know, kind of scared me into it. And he never proved my innocence to anyone. So you know, I came out and, and pushed and I, and I guess my story is, is kind of like how we mentioned, right? I came back and I pushed myself to make sure that my kids and my family and my wife would never be in a situation that we were in, like just of un. Unexpected, you know, not having any, any money. Right. So I, I went all out and I persevered and I just came back with a vengeance. And I worked really hard and within five years I took us from pretty much broke to 15 million dollar net worth. And a lot of it was, was, was buying rentals, right? Buying things that, that I can, that I really just believe in, focused in. And my goal right now is showing my kids. So my kids actually go with me to events and they're actually learning the business. Whether they end up doing it, not sure. But at least they know how to do it, right? That's, it's. I believe in passive income, how important it is and if I can teach them that, that's kind of my goal. I mean they're 14 and 15 years old and, and they're, they're learning how to underwrite apartments. So I'm a, I'm a proud dad. For sure.

For sure. Yes. Yes. Your son is a good kid. I can vouch for that for sure. Thank you. So, and another thing is you didn't let an injustice define you. You rose above you. You were able to not only find power when you were down, but you didn't let it define you. So that's, that's huge. And surely it's a lesson for your kids as well. So as you got started, I, I believe that was with flips and whatnot. Were you, were you, when you say with vengeance, were you working with wholesalers? Were you finding these deals yourself or, or what, what were you just super good at flipping and making money on the, on the investment part of it there?

Yeah. When we, I mean all the above, we, we, we worked with wholesalers, work with real estate agents. I mean I made sure, you know, there's, I don't believe it or not, I didn't use any marketing money. Like my only marketing was my time. That's, it's, it's really about your time and your, your relationships and your word. Like I would go out there and I just started meeting with wholesalers and agents. I would be upfront with them where we're at in the beginning. And we went from, you know, from zero properties to almost 80 flips here in San Diego alone within, within, almost within two years. So we were, we were going pretty fast again. I was so hungry and determined to succeed that I kind of, I say the saying right about determination. Determination doesn't ask for permission, you just gotta go do it. So it's not asking permission or anyone of how to get there. Right. It's just getting it done and realizing your goal and making sure you get.

There and you're in San Diego.

I am in San Diego based out of San Diego, but we're actually in five markets for flipping and then buying sunbelt states throughout the United States.

That's great. Yeah. But now San Diego is not a cheap place to be playing. That's where you started though, right?

That's correct.

So what, what's the typical price you were paying when you got started? Do you know roughly, do you remember?

Oh, I remember. I remember back in the day, high end homes before the crash were 6 to 800,000. Now that's entry level pricing in San Diego. So you know, kind of interesting to see the growth.

I do have a brother and nieces there. I love San Diego. Anyway. Very good. Well so. And now you said you are scaling into apartments as well or you are not scaling, you already have, you're into several apartments. Go ahead and talk about your first apartment purchase.

Yeah, well, the first one actually here was here in San Diego. I kind of wanted to get my feet wet and it was a 23 unit, but if about, just, just right around 2.6 million I believe is what we paid for it. And you know, we worked it, we had, we, we owned it for about gosh, probably close to about five years. We just sold it this last year actually and, and definitely went full cycle on it and I loved it. I mean it was, it was just showed me the, the power, how powerful it is to have all units in one spot and you know, building the teams around it and having great property management to help you kind of get to your goal on that side. So that was the first one and then we just kept growing into more and more and we have about 580 at the moment.

That's terrific. Now that first one, did you do syndication or was that just a joint venture? I heard you say you brought in a team, you made it created.

Yeah, no, and more team. Like just of, of. When I say team it could be just obviously from the contractors to the property management Everything. Right, everything that, that, that it takes to get it to, to the stabilized moment. No, but we bought that. We bought that by ourselves. We bought that just with me and maybe, I think it was, it could kind of consider it a joint venture with me and one other, a money partner that we bought it together.

Nice, nice. Okay, and so now you have. Did you say five apartment projects?

No, we have a total of 11. It's about 580 rental apartment units.

Gotcha. Okay, and so what, what age bracket are you aiming for in your buy box?

You know, in the beginning, I was just kind of seeing what's out there. Right. Getting to know. But now that we've really focused, I think we're focusing on really 19, 1980s and newer is kind of our buy box currently on most of our properties.

I see. And San Diego, I'm trying to remember, do you have air conditioning there that much? Right?

We do, but not, I mean, not really. I mean, it's kind of a commodity. It's not really been needed. Depending on where you're at in San Diego with the coastal breezes.

Right, right. Well, yeah, and it's. That's such a regional thing. I'm in Florida, where everybody really wants air conditioning. So as far as. Well, so if you're buying in the 80s, then you're not having to deal with flat roofs much or some of those nuances that most people are really back and forth about. Right?

Yeah. I mean, we've had a mix, you know, especially with everything we've done. We've had a mix of, of different types. But I think we're trying to. We've. We've learned which ones are more. A little more of a headache and a little more work, and we're trying to kind of focus on the ones that we know we could just really get in and out or get it stabilized a lot faster.

True, true. That's right. You have the, the. Yeah, you probably do have a lot of flat roofs there because of the Spanish influence. Right, Correct. Yeah. But you don't have the water. We do here in Florida.

Oh, very true.

Yeah. So it's a problem here. So, so when you're doing your Renault, your renovations usually. Are you getting into windows and the heavy duty type renovation, or are you trying to buy something that's more quick to turn around?

On our apartments, we're trying to do, you know, quick renovations. We will do windows if needed, but we typically won't if they're in good condition. You know, very, very different than our fix and flips. Right. Our fix and flips, we will change out the windows almost 90% of the time with apartments, it just really goes to see what, you know, what's, what's typical in the area. Right. What's, what's other apartments, where they at? I mean, is it, are they functional? Are they working? Is it standard? So just kind of every, every apartment building is case by case, and we're looking at everything to make our decision.

And so with you being in five markets, you said that you do before we came on the recording, have boots on the ground in all those places too. Want to touch on building teams, your approach and how you, how you've been able to do that.

Yeah, well, we, you know, we expanded during COVID We started going to other markets. I went from San Diego to Jacksonville, you know, almost across the country. And, and it really, it was a learning lesson and it's really about building teams. So we have, we're currently in five markets in Jacksonville, Tampa, Nashville, and San Antonio and San Diego. And we have boots on the ground every single market, you know, and it's, and it's something that we've noticed. It's needed for it to work and, and really just, you know, you're hiring people, getting to know people, and it's, it's not easy. Right. So, you know, sometimes you're, you're hiring and firing, but when you find those right people that you end up keeping, oh, man, it's, it's just amazing. It's day, night. It's almost. You become unstoppable of what you can do with the right team. So it's some, you know, it's not easy. I can't make it seem like you're going to hire the first person. It's going to be perfect. Maybe it is, maybe it's not. But know that the good people are out there and, and, and once you find them, it's just so valuable to, to keep them happy and, and grow with them. Right. And it's, and that's what, that's what's allowed us to grow so quickly and, and throughout these markets that we're in.

So how are you finding the people you want to actually do the renovations when you are in like a place across the country?

Yeah. I mean, for our, you know, for our fix and flips in the markets that we're in, I mean, that's us. That's us. Literally. Are my boots on the ground? Are meeting contractors left and right, you know, doing their due diligence, even just trying to find them. Right. You know, asking around and, and. And once we find them, you know, give them a shot on the property and see how they do. And, and if they work out, great, we keep using. If they don't, we move on to the next one.

So you don't have a method when you're dealing across the country?

Yeah, well, I mean, that's. That. I mean, when we're. I mean, that's. For our. In our other markets across. Across the. But like, we do apartments, we work a lot with the right property management companies. I can tell you that has been the biggest. Aha. For us is making sure you have the right property management company. And a lot of these property management companies, they already have crews for you. So we don't actually have to go look for many, many crews ourselves because they already have them. So, you know, finding that right property management that already has those crews in the areas that you're in, you know, and just confirming pricing, that has made it really easy for us.

Yeah, that's the secret sauce there, right?

Oh, yeah, for sure.

Right. I'm pretty entrenched with the local apartment association here in Orlando. And then on a statewide level, and that carries into the national level right now is when a lot of legislative issues are going on. And last year I was involved going up to Tallahassee and campaigning. They were trying to do rent controls here. I don't know if you were aware of that, but. So we were meeting with legislators and talking about how bad that would be.

Right.

So. And then that. So that was on the statewide level. And then after that, the national one will be it. It's again next month on the D.C. trips. But anyway. Yeah, no, that's a. That's a. That's a really great thing. And not enough people really think about these property management companies that are syndicators, in my opinion. I think that the management companies can be a lot of help. So as far as the whole family mix, do you have your kids involved with doing some renovations too?

You know, not necessarily. Right. I mean, they're. They're both in high school and. And it's tough. Right. They still got their teenage, you know, things they do. They play sports. They're, you know, with their friends. So I, I kind of. I try to balance it. I'm trying to do. As much as if it were up to me, they'd be all in with the business. But, you know, I want them to be kids. And my son still plays video games and then he's running deals sometimes in the afternoon. So it's so cool to see the little bit of mix right now. I have them really focused on looking for the deals, understanding the deals, understanding why they're good, understanding why we want to pass on certain deals. I think that's huge. Right? Because sometimes people get excited and they'll buy something with the advice of someone else and not knowing, you know, that person is just trying to make a commission, sadly sometimes. And can you end up buying something that's, that's not a good fit, that's not actually a money maker? So I'm trying to teach them that first and then kind of the power of teams, you know, having, having the same, same, same thing what I just said. Right. Like, even for them, are they really going to be. Go hitting the hammer across the United States on, on the rental? No, they're going to hire the right people. But you know, how, how do they find them? Right. Working with that. Right. Property management company, checking what your insurances are like, you make sure you're getting different quotes. I think I'm, that's my main focus with them right now. And then as we get the deals. When they were kids, they would go to the, to see these properties all the time. Here in San Diego, we literally go on Sundays and drive around and look at all our properties, whether fixed up or in the middle of it, and go through the construction site and make them understand. So they've had a lot of history of it and I think now they're getting to see, well, why do we even buy it? Right? What's, what's, why is this a good deal? And I think that's kind of their next path right now.

That's great. Yeah. Yeah. Well, so anything else you would like to add?

No, I mean, I just think, you know, I share my story of, you know, kind of again, pushing through. I just, if there's one person on here that is thinking about quitting, you know, in the middle of a bad spot, maybe about a bad deal or, or being involved in, in some type of project that they're not happy with. Like just, I just tell them just keep pushing through. Real estate's an amazing avenue for, for especially for passive income and for building your wealth. So it just, it's, it's hard sometimes know that I've gone through it. Even though, yes, we hit some great milestones, but it's, it's never easy. Right. You just got to keep pushing through and align yourself with the right people.

To get there right now, I forgot to tell you, I always ask whoever I'm interviewing if there was a personal, a pivotal person or event that happened to put you where you are today or where you're going. And so I ask you, is there a pivotal person or event that you would, you would identify?

Yes. And I. And first person that comes to mind is one of my investors. His name is Mike, and I've known him for years and we've become friends over the years. He's invested with us on hundreds of flips, and I just saw the way he invests in passive income and how he enjoys life. And I think when I really got to meet him and we ended up becoming friends, hearing him tell me, enjoy to enjoy life, not to forget to enjoy life, we could work really hard. And I think a lot of us are go getters and we work hard, but don't forget to enjoy life. And I think that's what's changed my projection. He also gives back a lot. And so we've started giving back to two foundations over the last couple years, too. So the joy that that brings me and bringing my family into that, like, we've gone to build some homes in Mexico for some foundations and mission trips, and I think that's just changed the way we think. Right. We're working hard to, to live a great life, but we're also giving back. And I think that's, that's, that was a pivotal moment for me, him sharing that with me and getting in my head of what, what was my reasoning on really doing this and where's, where's my end goal? Because, you know, I feel sometimes how much, how much is enough is enough and money making money, you know, it's, it's, it's kind of a, everyone has that, their own answer for that. But for me, like, I'm a frugal guy. Like, we live in a great spot and, and why not give back if we can, if we, if we can. Right. Help some other people because we're so privileged and, and share it with others. So.

Well, that's great. That's great. Okay, well, Jesse, why don't you tell people how they can get in touch with you?

Yeah, that'd be great. If anyone wants to reach out to us, they can, you know, want to talk about what they can invest with us with and, or bring us deals for our flips and, or apartments. You just go to investwithjesse.com set up a time with me or my team, and we'd love to talk to you and go over what we have available.

Great. Okay. Well, thank you again. And we'll put all that in the show notes, too. I appreciate you coming on the show.

Thank you, Jeanne. Appreciate it.