
Show Summary
In this episode, Darrell Jackson shares his journey into real estate liquidation, the impact of the silver tsunami, and how building relationships and leveraging technology are key to success in estate planning and real estate investing.
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Investor Fuel Show Transcript:
Darrell Jackson (00:00)
Going forward, how do you split a house? Like a lot of people are just like, Hey, I just want the money, right? Well, it that works out perfectly. Like it sounds horrible and everybody’s like, ⁓ we wanna keep the house in the family, but a lot of times it’s just not practical. And so Jacksons Crossing, we’re backed by a network of real estate investors across ⁓ the country who are looking to buy properties. I mean, I’m I’m primarily focused in the D C Maryland Virginia market.
Joseph Crooms (02:00)
Hey everyone. Welcome to Investor Fuel Real Estate Pros Podcast. And today I’m going to be joined by someone I’ve been looking forward to chatting with. His name is Darrell And I’m not gonna tell you his last name. I’ll let him do that. He’s been ⁓ making some serious moves in a unique way in the real estate industry, but I think he’s positioned on the other side, and he’s going to show us ⁓ how he got into it, and he I’ll let him explain that more. So ⁓ hey Darrell, ⁓ glad you’re here. ⁓ I think our listeners are going to take something away from you ⁓ and how you approach the business, especially the two sum the the tsa mis that you spoke about. So we’re gonna I’m gonna position that question so you can explain because I heard two to some tsa mis that you that you’re you’re addressing. So we’ll we’ll gonna ask you that. So let’s dive in. So for people who may not be familiar with you in your world, give us the short version. What’s your main focus these days and what markets are you operating?
Darrell Jackson (03:11)
Okay, so my name is Darrell Jackson. I’m the founder and CEO of Jacksons Crossing, the premier real estate liquidation solution for estate planners, fiduciaries, and families. so what that means is a lot of times ⁓ people pass away and ⁓ a lot of times they leave behind a house. I think it’s over seventy percent of of estates and probates. ⁓ the largest asset or the only asset is a house.
And a lot of times when people inherit a house, or when people think of inheritance, they think of money. ⁓ but a lot of times what happens is they inherit a house. Now, surely enough, a lot of people in ⁓ sort of Gen X and Baby Boomer ⁓ generation, ⁓ they they had multiple siblings. And ⁓ what happens is it’s very difficult to inherit a house or to share a house amongst three or
multiple ⁓ adult siblings with their own separate lives. A lot of times people just say, you know what? The best thing for us to do would be to just sell the house and split the money evenly and we just sort of move on. We don’t have to worry about it. how I actually started was I was working for an investment company and my great grandma passed away. She had her three sons my grandfather and his two brothers. ⁓ Initially
The thought was, we’re gonna keep the house in the family, ⁓ and we’re gonna fix it up and rent it out. And they had all these ideas. but then there was time when there was there was bills due. There was there was a tax bill that needed to be paid. Then also my great grandma’s funeral costs ⁓ were also bills and the things just kept piling up. And it’s in Harrisburg. We live in Baltimore and I had an uncle in California and an uncle in Philly.
So it really just didn’t make sense for them to just keep it in the family. They’re like, ⁓ so my grandfather, he he said, How about we get a little fella a shot? is what he said. ⁓ so I basically I went in, did my regular process. we got inside, we took pictures, we took inventory, we spoke to some investors in the area, we looked at the the resale comps for both rentals as well as flips.
⁓ and then ⁓ we we were able to get my grandfather an offer. My grandfather’s an estate attorney. ⁓ and this was he had prepared the estate for my my great grandma, his mom, and ⁓ so he prepared that and then ⁓ we got it closed in about a month. they split the money and we I mean obviously we got the things out, but that gave me
⁓ sort of a a vision of how I can take the off market ⁓ or the wholesale and mix it with estate planning. my first ever job was in estate planning because my great grandfather’s an attorney and his father was an attorney. And so the plan was that I would be first generation I would be third generation attorney attorney in my family. ⁓ But when I got to college ⁓ I realized
I wasn’t gonna be able to do seven more years of this. So I was like, I guess I’ll be first generation disappointment. ⁓ so ⁓ no, but ⁓ I was it’s cool ’cause I was able to work with my grandfather on a few different occasions as far as estates that he had. So yeah.
Joseph Crooms (06:44)
So Darrell ⁓ you caught my interest ⁓ when you spoke about the Tu Samis, and you spoke about it from a generational ⁓ transferring of power or a transferring of responsibilities or income. Can you ⁓ back up a little bit and share what’s that first stage, what’s that first to Sami that you saw and how did you know and what what did you how did that shape your vision today?
Darrell Jackson (07:58)
Okay. yeah, yeah. So which the what I believe you’re referring to is the silver tsunami, correct? Yeah. ⁓ okay. ⁓ so ⁓ the as we all know, the the great generation or what is it called like the greatest generation was ⁓ the from like the thirties to the those born in the twenties I guess and they were they had kids in the in the forties and fifties and we see all the the things about the economic growth that was
Joseph Crooms (08:03)
Yes, yes.
Darrell Jackson (08:27)
of the the fifties and the baby boomers and the baby boomers experienced the greatest creation of wealth in American history. ⁓ they own I think it’s something like s 70% of the real estate ⁓ like the private owned real estate they they have a lot of the holdings and everything. ⁓ but now as they pass away we are witnessing the greatest
transfer of wealth in American history from the baby boomers to Gen X and the millennials and Gen Z ⁓ as they pass on. ⁓ so more and more you see issues like with my my great grandparents and with my my great grandmother and my grandparents of like people who basically inherit a house and they have no plan to move
Going forward, how do you split a house? Like a lot of people are just like, Hey, I just want the money, right? Well, it that works out perfectly. Like it sounds horrible and everybody’s like, ⁓ we wanna keep the house in the family, but a lot of times it’s just not practical. And so Jacksons Crossing, we’re backed by a network of real estate investors across ⁓ the country who are looking to buy properties. I mean, I’m I’m primarily focused in the D C Maryland Virginia market.
But I’ve done business in Pennsylvania, Michigan, ⁓ Florida, Louisiana, Arizona, California. we’ve done business South Dakota had a r a random deal in South Dakota one time. ⁓ and that was another estate plan. But ⁓ the thing is, I mean, ⁓ we’re just looking to support
estate planners, fiduciaries and families who really I mean they have this house and they could really use the money, or there maybe there’s rental properties and maybe somebody was a a landlord and then they pass away. And then there’s all these in instead of one big house, there’s fifteen ⁓ fifty thousand dollar investment properties ⁓ that just aren’t aren’t practical, right? And so
our network we’re backed by investors that’ll say, hey, I can give you this for this, this for that, this for that and we’ll go through we’ll go through the whole thing and we’ll get you a a a big offer for all of your properties and get you liquidated in thirty to forty five days.
Joseph Crooms (10:58)
So Darrell let me ask you this question. What you’re saying is really a relationship building process. How do you get the the transfer for the younger generation now from the baby boomers? And they may not all be like your grandfather who who you know who was a lawyer. How do you get the lay people, how do you gel those two together?
And is there difficulty trying to ⁓ so when I say gel and get it, how do you explain what you’re doing to both generations? You got the the the the the baby boomer such as myself, I am a baby boomer, who has this this pre perception of this is how we’re gonna do it, and then you have the the the generations that I may be leaving it to. I want to infringe my thoughts on them, but
Darrell Jackson (11:23)
What do you mean?
Joseph Crooms (11:46)
you’re bringing in something I don’t even think about because I never thought about selling the property or someone buying the property. How do you build that relationship, especially in a climate like today?
Darrell Jackson (12:31)
Okay. ⁓ so it sounds like ⁓ sounds like you you want to build a legacy and your idea is to ⁓ pass your real estate down to your kids. Right?
Joseph Crooms (12:44)
And
it’s a question for our listening audience, because we need to know how do you make this happen? Because you got yeah, you got these two different philosophies on you got the older generation that that are the property owners, right? And then you got the inheritance. And they’re they’re they’re fighting, so how do you present how do you offset that that tusami for controlling the conversation so much?
That it destroys it. Can you s tell us how do you keep this
Darrell Jackson (13:14)
So
is listen, as long as as long as Jacksons Cross is around, then there needs to be no fighting between ⁓ between ⁓ inherit in ⁓ inherited heirs. ⁓ so I mean essentially you can split liquid money way easier than you can split a house or whatever. So ⁓ I mean if you work with us what we’ll do
basically I can tell you a bit about ⁓ my process or our process is we get in ⁓ we have a short survey ⁓ that I have people fill out to the best of their ability ⁓ from there we’re able to we get the information I’m able to talk it over with my team we can either send people out or have you take your own pictures of the property you get us the the pictures we can then run comps
And look at what we can offer or what our investors can offer. ⁓ from there we formulate an offer and we extend the offer to the the the personal rep, the attorney, the whoever. ⁓ and they say, ⁓ well, maybe I I I was looking for a little more. And then the conversation becomes, well, how much more are you looking for?
And is there is is does timing play a role at all? ⁓ because a lot of times people like I said earlier, a lot of times people want more money and that’s fine. If you’re willing to wait longer, then you might be able to get more money. If you let’s say we’ll take the property as is, ’cause we plan on fixing it anyway. But if you wanna quote unquote maximize, what you can do is you can put your own money into it, ⁓ and then you can
Do all the renovations and everything, but you take on all the risk, right? So a lot so Jacksons Crossing de-risks this process ⁓ for the inheritee or the heirs. ⁓ because we take that off of your hands. We get you ⁓ a cash out price that you can walk away with in thirty to forty five days, so you don’t have to worry about it. And ⁓ and our team we take it over and we
We do all the flips and everything. We and I’ve even I’m working with somebody right the case I was telling you about earlier. ⁓ we work you we help you work through the estate planning ⁓ or the probate process with the attorney. I’ve matched people up with attorneys, ⁓ to even get the process initiated. ⁓ I’ve worked with I’ve come in at the end when
The attorney has already done it and they just don’t know what to do with the property. I’ve I’ve been in every different scenario. and I mean look, we just want to get it done quick ⁓ for all of our people. And like I said, we work in all different markets. We have and there’s no there’s no limit as far as how many properties, or there’s no limit as far as how much. Like I had this one property.
that basically the the two brothers had the two brothers had inherited the property from the mom who had passed away but they didn’t go through the proper estate planning ⁓ process. All she did was quick claim deed the property to the two boys. So when they as soon as they got it, they were incurring capital gains tax every day. By the time he got to me, they had a a tax bill
I believe from the federal government that said they owed ten thousand dollars that they just didn’t have. Right. So they came to me and they’re like, Hey, can you do anything? I said, Of course. We were able to get them ⁓ close to a quarter million dollars. we made a sizable fee on top of that as well. And the property ended this was in north this was in Northern Virginia. The property ended up selling
a few months after us, like after we sold it to the investor, ⁓ it ended up selling for eight hundred thousand dollars. so that was my largest deal to date. and I’m actually I’m working on a development deal right now for or an acquisition. ⁓ I can’t really talk about it. I’m on under NDA, but ⁓ there’s an expansion coming
to our business we’re expanding ⁓ through family offices and private equity.
Joseph Crooms (17:47)
Now every operator I know has a moment when things get real. Can you share with our audience, Darrell ⁓ maybe a deal that went sideways or a time that you had to pivot fast?
Darrell Jackson (18:39)
Okay. That’s a good one. ⁓ so my biggest the time when something got real was ⁓ basically I had a deal. I was still I was I was just coming off the that large eight hundred thousand dollar deal. ⁓ and my my my grandmother, the my great grandmother and the eight hundred thousand dollar deal, those were those happened in the same month. ⁓ I believe that next month I got this one.
where this lady passed away. She had ten she had like ten rent rental properties and they were all like she had like the fifty thousand dollar properties, the twenty thousand dollar property with the Section Eight tenants. She had they weren’t in great neighborhoods and they were all like sort of scattered, right? And so basically ⁓ we were working with them and ⁓ I was working with an attorney that I didn’t know
that I didn’t I mean I was I just sort of was thrust into the situation through a referral. and like it seemed like and for one, the the management company, so they’re selling the properties, right? But the the property management company, they actually lose if the person sells so they were ⁓ we were under constraints with the attorney and then the
the property management, they keep dragging their feet ’cause they don’t want to sell ’cause they don’t want to lose their money. So they keep dragging it out and they keep they’re being a obstructionist and everything and so then I had to deal with that. And then like there were little things like there weren’t proper disclosures on one of the properties. ⁓ so they didn’t disclose that it actually wasn’t a legal two unit. It was a a ⁓ one unit
That like and so it was just things that were falling apart and it and so basically what happened was it was ten properties, it was a sizable payday. Again, this is right on the heels of these two large deals that I did. And this is right on the heels of that, and this is my first partner deal. and I’m de I’m working with the attorney and I’m doing all the things, I’m really willing and dealing.
And then ⁓ at the last minute, basically the deal dies because we couldn’t because because of the disclosure, we couldn’t sell one of the properties out of the ten. We had we had everything except for one because there wasn’t a pop proper disclosure. So it wasn’t even our fault. And then the attorney, what she basically does is goes behind us and finds the person who was gonna buy it, and it
And goes behind this and does it ⁓ after basically we were being obstructed. so that was that was a huge loss. It was is very upsetting. ⁓ and I I I took a bit of a break ⁓ from at that point and I went to go ⁓ I I went to go study ⁓ well I I went to go teach English in Costa Rica for a bit to get my head back. so I taught English in Costa Rica, had a wonderful experience.
Then came back and s got started completely on my own, not as a subcontractor. And ⁓ I got a deal right out of the gate, ⁓ a referral. we were able to close it. And this was actually something that I had been working on from four years earlier, and I got it closed and ⁓ I was able to start and I’ve just been on the journey ever since.
Joseph Crooms (22:15)
Now this sort of leads me into my next question and thank you for being transparent and showing how key perseverance is. That’s the kind of stuff people don’t talk about enough. And honestly, it’s what separates the folks who are just dabblers or from the ones who stay in the the the long term. Let me ask you this. What are you focused on solving or scaling next? What’s your next real goal for you?
Darrell Jackson (22:39)
⁓ I I mean I it’s in the works right now. I can’t really say, but ⁓ or I can say, but build to rent. build to rent is definitely my dream. ⁓ like development ⁓ and build to rent is the next thing that I want to do and bring to my area. And where are you located, by the way?
Joseph Crooms (23:02)
So I I’m located in New Jersey, so we do the we’re we’re independent podcasters for Investor View. So we’re going to also give you ⁓ this this ⁓ tape so that you can have for yourself and ⁓ for every category that you may have connections with. So this will be given to you as well. So ⁓ that’s big, especially when you’ve already shared your experience, talked about perseverance.
And the uniqueness of what you’re doing is is is in place. ⁓ that next move can either compound things or create chaos depending on how you play it. Now I know a lot of people listening are either early in their journey or looking to level up, and hopefully this introduction will get more people interested in your side of the real estate. So that’s very important. So I think that their benefit from hearing this when it comes to building relationships.
And drawing a network. What’s made the biggest difference for you?
Darrell Jackson (24:00)
⁓ truthfully technology LinkedIn, ⁓ I love it. ⁓ because I love I just love it because ⁓ it really it gives you like I’m connected with people I would never meet. Like I would never I would never naturally meet these people, but LinkedIn everybody is every like I met with this guy and ⁓
He’s an old guy in Southern California. And we’re just we ended up on a call together. I think he used one of those services that books cost. And I’m I’m like talking to this guy. And I’m like, l like if if things were ten, fifteen years ago, we would never like we wouldn’t ever set this conversation up. But it’s really cool that like I’m a part like we’re a part of this conversation. We’re talking about like
Where we come from and our experiences. I just think it’s so cool how literally you can talk to anybody like through like LinkedIn or whatever sort of platforms you have. You can be in the room with Zoom, ⁓ with any sort of person. Don’t be afraid to ask. Don’t be afraid to introduce yourself. ⁓ and I mean, like don’t be af afraid to to fail or to fall.
Like a lot of people they get so caught up in they w they’ve seen so many star entrepreneurship stories or journeys like ⁓ to where somebody came in and everything worked out for but like truthfully, the people who you think every like I’m I’m thirty two and I’m blessed and people are like, a thirty two year old entrepreneur, ⁓ that like I mean things things have been wonderful, things have been horrible.
And ⁓ so like I mean you don’t get there from from from just just playing it safe. I say you go for it all. ⁓ and once you go for it all and then you fall, then you can sort of correct things and you can do things differently and you can redeploy or you can regroup or you can meet new people and you can build a team of like like minded ⁓ individuals. Like I’ve had so many different
quote unquote failures that have only informed my direction to success.
Joseph Crooms (26:19)
So Darrell you’re saying data from the failures, how you capitalize on it. How would you word that in your own sentence for your for the audience?
Darrell Jackson (26:27)
I
mean d you you can’t like a lot of people they love the idea of just doing the safe thing. And if you always play it safe like I made a bunch of money when I came right back in and I I did that deal. I made a bunch of money. I could have played it safe and I could have been very incrementalist. But no, I said you know what, I made this lump sum of cash. What I’m gonna do is I’m gonna I mean I’m in a ⁓
My situation is is fine. I’m gonna put all this money back in onto the table. I’m gonna I’m gonna pay for ads. I’m gonna ⁓ I’m gonna fly across I flew across the country to Anaheim, California for the national estate planning council meeting. I joined the Baltimore State Planning Council meeting. I ended up meeting the president and he the president of the national organization and he was my sponsor into the
Baltimore ⁓ organization. So it’s like I’ve like I put it all on the table. I’ve made mistakes. I’ve done things wrong. I do things differently. But like I don’t view the things that I’ve done wrong or that I or that I would do differently now as mistakes. Because they just inform what I know to do next time. So the people who are sitting on the sidelines like who maybe have seen me fall
quote unquote fall on my face because the the return wasn’t outside outsized. like I mean all you’re doing is sitting watching me. You’re not you’re not out like doing it. You’re not out making it happen. And so when as soon as you do decide to get in, like you’re you’re gonna be so far behind and no one knows your name. Like everybody knows me. Like if you say
If you type in ⁓ real estate liquidation solution, I’m almost certain Jacksons Crossing comes up at some ⁓ yeah, and I I have an estate planning talk ⁓ newsletter on LinkedIn that I’d love to plug ⁓
Joseph Crooms (28:31)
Yeah, so so but see see Darrell he you see how he he’s a winner because he just he got a little head of the broadcast. So let me do this. First of all, you can’t fake relationships and we’ve seen that right here with Darrell. So let me get this. Alright, before we wrap up, if someone wanted to reach out to you, maybe collaborate or learn more, you see where I’m going now? and what you’re doing, what’s the best way to reach you and Darrell?
Repeat it twice, because somebody may be fumbling for papers. So I want to make sure ⁓ the first group get it and the second group. You’re on the show. Tell us how we can get in touch with you.
Darrell Jackson (29:06)
Okay. ⁓ you can get in touch with me on LinkedIn. My name is Darrell Jackson, D-A-R-R-E-L-L, J A C K S O N. ⁓ and if you wanna you can follow me. And then you can also, ⁓ Estate Planning Talks newsletter ⁓ is my newsletter. Can I drop a link or something?
Joseph Crooms (29:29)
Sure, yes you can. You can w won’t you share the link? ‘Cause this is this is pretty much verbal. They may not see that. So can you spell it can you sort of sh share it spell it out for us? Take your time, we good.
Darrell Jackson (29:39)
Yes, estate E S T A T E Space Planning P L A N N I N G T A L K
Joseph Crooms (29:53)
One more time.
Darrell Jackson (29:54)
Estate planning talk E S T A T E Space Planning P L A N N N I N G Space T A L K on LinkedIn ⁓ Estate Planning Talk on LinkedIn
Joseph Crooms (30:15)
So perfect. Well listen, I appreciate your time, your story, your perspective. We need more people in this space who’s doing the right thing. Thanks again for being here. ⁓ it is our pleasure. As ⁓ as for those tuning in, if you got some value from this, make sure you subscribe. We got more conversations coming from more operators like Darrell. And and did I pronounce your name Darrell? It’s Darrell. Darrell.
Darrell Jackson (30:26)
Thank you for having me.
Is the
Joseph Crooms (30:43)
Alright, so from Darrell ⁓ and ⁓ and who is just out there ⁓ building real business. We’ll see ya in our next episode of Investor Fuel Real Estate Pros Podcast.


