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Carlton Dennis
Most people will invest with somebody else after they build trust with him. For me, I didn't know Grant Cardone. I had never met him before in my life. Never went to a 10x event? No. But did I download books? Yes. Was I listening to his podcast? Yes. Did I start getting some value out of his sales training? Yes. Was he talking about real estate? Yes. Was he bringing up other wealth teachers that I admired like Robert Kiyosaki and how he bragged about not paying taxes because he was using the tax code in mind? Yes. And I was an aspiring tax professional and to hear somebody that was advocating for the tax code whilst at the same time advocating for real estate, it was in perfect alignment with where I was in my training. I was just learning about the tax code and how you can use real estate as an investment and as a tax write off. And for me, I wanted to make mailbox money as soon as I could. I had that fixation of I'm going to live off of passive income so I might as well start right now. I just didn't know what went into actually earning passive income.
Justin Colby
Yeah.
Carlton Dennis
And so because I did not know what actually went into earning passive income, I thought I might as well partner with somebody who's already done this. I'll go put my money with Grant Cardone as a limited partner, knowing that I won't take on any operational risk and I get to benefit from the upside of him managing the property and him running the operation.
Justin Colby
What is up? The Moore show welcome back. And again, you will not want to miss this episode because my guest sitting right here now, as always, every episode is brought to you by the More Club. This club is for real estate investors that teaches you all the opportunities that are in real estate. The opportunities that we're going to talk about today with Mr. Carlton Dennis, tax strategist as well as real estate investor. What's up, brother?
Carlton Dennis
Dude, I'm doing amazing, man.
Justin Colby
Yeah.
Carlton Dennis
Back in Miami. Come back in the MOVE studio for another podcast. Excited to be here, dude. Thanks for having me.
Justin Colby
So you are well known. If anyone's not following him, go follow this man right now. Carlton Dennis, well known for your tax planning, tax strategizing for all types of industries and for business owners.
Carlton Dennis
All right.
Justin Colby
But you're also a real estate investor. Not a lot of people know this about you.
Carlton Dennis
Yeah, I am a real estate investor. I use the tax code the right way and real estate happens to have the best benefits in the tax code.
Justin Colby
So let's jump right in. What are you focusing on right now, today, 2026, as a great real estate investment?
Carlton Dennis
You know, my real estate portfolio has actually changed over the last couple of years. I used to have tons of single family. Now I've migrated into multifamily and, and since of about, about eight months ago, I've started to pivot into gas stations as a big part of my portfolio. So I'd say like at least 30 to 35% of my investment portfolios now in gas stations.
Justin Colby
So first of all, you'll keep your hair longer cause you got out of a single family, so that's good. And it won't go gray as fast. So that's a good cause I would have suggested that. So gas stations, first of all, I think the challenge to start will be where to find them. Yeah, but what about gas stations create such a great sexy investment strategy for you.
Carlton Dennis
All right, so I gotta let everybody know the, the reason why I would even go into gas stations, because it doesn't sound sexy right away, is because of depreciation schedules in the tax code. Certain things depreciate over certain time periods. A residential Property depreciates over 27 and a half years. A commercial property depreciates over 39 years. Well, guess what? Gas stations depreciate over 15 years. That's much shorter than residential real estate, much shorter than commercial real estate. And so when you are looking at strategies in the tax code like cost segregation, study bonus depreciation, what these strategies are essentially doing is allowing for you to break down components of the property that are non structural components of the property. Think flooring, windows, appliances. The IRS says great, you can write these things off in a quicker amount of time. But there's a five year bucket, a seven year bucket and a 15 year bucket and only the components that are 5, 7 and 15 year can you take bonus depreciation. You can write them all off in one year. But the building structure has to be written off over 27 and a half years or over 39 years. Not with gas stations.
Justin Colby
Wow.
Carlton Dennis
That structure has 15 year depreciable life. So what does that mean? It means you can do a cost segregation study with bonus depreciation and write off the entire purchase price of the building in year one. There's no depreciation left in year two, year three, year four, you are taking a hundred percent of your depreciation. For a lot of my clients, especially myself last year it was a very leveraged strategy. You put a hundred thousand dollars into a gas station fund, for example, you might get a 350, $400,000 depreciation deduction. For someone like myself who put dollars in, I got a 4 million dollar write off.
Justin Colby
That's insane. So first of all to, to rewind quickly. Normal depreciation in a multi family is what are the things that we are depreciating?
Carlton Dennis
Yeah, when you're depreciating multifamily, you're depreciating structure and non structural components. Structure is what you think of when you're driving down a road and you're seeing a house being built. The wood, the load bearing walls, the steel, the concrete. That stuff's going to last 50, almost 100 years. We have some homes that have been here for well over 50 to 100 years. But all the things that go inside of the property, all the cosmetic stuff, the paint, the flooring, all that stuff is actually considered non structural components. And if you hire an engineering firm that's partnered with a CPA or a tax professional, you can perform a cost segregation study. You're performing a study to segregate the structural from the non structural. And the IRS says you can depreciate the non structural faster. The only issue is, is that when you do this study, you're going to identify some stuff that goes into a five year depreciation schedule, which is great, like appliances and things like that. But then a lot of the rest of the stuff, like H Vacs and a lot of the piping that goes into 15 year. And even though you're writing it off faster, I mean, geez, it's still 15 years it's still five years. So we like to use the cost segregation study plus bonus depreciation. The bonus depreciation law says any real property that has useful life of 20 years or less, you could take 100% write off on it. Well, this is great, especially with the one big beautiful bill. We can now write off 100% of non structural components. And if you're a gas station, your structure is actually on a 15 year depreciation structure depreciation schedule. So you could take 100% of that as well.
Justin Colby
And so the next layer of the non structural, which means, for example, in these apartments you have 27 and a half years still.
Carlton Dennis
Yes.
Justin Colby
So you took everything that you could for the first 15, but you still have the remaining balance of those 12 years to have small deductions on the actual structure, which can be nice, I mean, but it's not as sexy as being able to take a hundred percent in year one because the entire building and the non structural are all in year one.
Carlton Dennis
Yeah, well, I wouldn't say it's not as sexy. I'm just finding the sexiest strategies in the. For sure. Let's just be real. I. I'm gonna, I'm gonna go find it and I'm gonna figure out a way to make it work for myself after I've. But most of my clients do start off in residential real estate or commercial if they have the means for it and they're qualifying their spouses as real estate professionals, or they're running the short term rental strategy, or maybe they're just operating real estate passively. But the real goal is, is if I'm going to accelerate depreciation, I want to make sure I can use that to offset my active forms of income if I have the means to. And for a lot of my clients, they may jump into real estate, even though they're only breaking even on investment real estate, just for the ability to offset their active forms of income. Because some of these people are in the 37% tax bracket. $100,000 deductions, $37,000 in their pocket, $200,000 deduction. Well, that doubles. Right. So that's what's pretty awesome about real estate is somebody else is paying down your mortgage while you're getting a massive tax deduction against your active forms of income.
Justin Colby
And so for you specifically, how do you get to write off your active income? Through this gas station model.
Carlton Dennis
Okay, for me specifically, I'm a gp, so when I went through this fund structure, I made sure that I est relationship with the operators. One of the reasons why I like the private sector space is because if you have the right type of relationships, you can get access to deal flow. And more importantly, depending on your level of being an investor, will determine on which side of the table you sit on. I remember early on we were talking about this on my podcast, that my very first investment was only a $6,000 investment into a syndication with Grant Cardon as a non accredited Investor. I had $11,000 to my name, Justin. I could only put $6,000 in while still being able to, you know, pay my rent and feed myself. But fast forward to today. I'm more of a sophisticated investor. I'm an accredited investor and I'm sitting on multiple investment properties. Plus I have capital to deploy. So I could be treated like a limited partner when I approach this deal and just be passive. But I made sure that when I established this relationship that they knew what my intention was. My intention is to be an active investor. I want active losses on the tax return. I don't want to sit on the LP side. I want to be a gp. So I negotiated what it would look like for me to make a larger contribution, to sit at the table with the GPS and make investment decisions like GPs do. And I got to benefit like GP's do when that K1 comes over on my tax return. It's not a passive K1, it's an active K1. Where does it go, Carlton? It goes to flow through to offset my active S corporation income where all my profit sits. For most entrepreneurs out there right now, those are the type of deductions that you want on your tax returns.
Justin Colby
So talk to us about LP versus gp. What is, what is the difference when it comes to taxes, but also just the concept of what is a GP versus an LP in these syndications?
Carlton Dennis
Yeah, absolutely. So a general partner is somebody that is operating. They're going to go ahead and raise the capital, find the deal, negotiate the loan terms, make sure the property's up in good standing, they play an active role. And if they're playing an active role, they're going to get active deductions that the limited partner might not be able to experience against active forms of income. So when the tax return gets filed for that LLC that everybody sits underneath the the GPS, when they get their portion of their K1, their portion of their K1 either comes out as a positive income or a negative amount. But that negative amount is considered an active negative amount, meaning it can go to offset active W2 or active to 99 income. Now, on the other side of the table, I can invest as an LP limited partner, which means I am limited in my role in how I make this property go. I don't have management decisions over the property. I'm not determining when to refinance it. I'm not building the business plan on how we're going to improve the property. I'm saying I want to put a little capital up, I want a little bit of skin in the game, but I don't want him to make any of the investment decisions that is going to allow for this business to be extremely profitable. That is awesome. Because you have less overhead, risk of you having to, you know, put your energy into the property, but it also comes with less benefits as well. When you go to file a tax return for that LLC different than the general partner, your K1 is going to report either positive income or a negative amount. But that negative amount is considered a passive loss, not what the IRS would say is non passive. And because it's a passive loss, guess what? It can only offset other forms of passive income. Not a bad thing. Not the end of the world. You just have to be aware of it. And many taxpayers who are going into real estate for the very first time through a fund or syndication structure are most likely going in as an lp, not a gp.
Justin Colby
Now, when you're a gp, do you have to sign and be responsible for the debt?
Carlton Dennis
Depending on the circumstances, you might have to be. Absolutely. You take on a lot more risk when you're a gp.
Justin Colby
And that's, that's the distinguishing factor on why to me, a lot of people don't even, they don't know what they don't know. Yeah, oh, I want gp, I want to get it off. Yeah, but now you're on the hook for the debt. A lot of times you can negotiate for sure. But at the end of the day, you also have to understand the risk you're going to start to play with. Right. Because if something goes wrong, you're also on the hook.
Carlton Dennis
That's true.
Justin Colby
Right. And so those are like, listen, there's a lot of opportunities in real estate. There's a lot of ways to negotiate those opportunities. You just have to go in with your eyes wide open about what is the upside, what is the downside and what are you really trying to achieve in Carlton's world? High income earner. I need to get some tax write offs on my income.
Carlton Dennis
Yes.
Justin Colby
I want to negotiate the GP model.
Carlton Dennis
Yes, you're absolutely right.
Justin Colby
Did you specifically get any leniency on the debt or are you a part of the debt as well?
Carlton Dennis
I'm a part of the debt as well. Totally okay with that. But here's the thing. I've been an operator of my own syndication before. So now I have experience of what it's like to talk to investors, to be a part of these investment decisions that are going on. I didn't go at this blind. And so I'm super grateful that I started early and I invested often, because when I was 24 years old and I got into that first syndication, I now knew what it felt like to earn mailbox money every single month without me having to do anything. But I envied the operator, the general partner that was running this deal, because I knew he was really making the big cheese. He was managing something that was so awesome. This opportunity for all of us investors who. Who really couldn't have access to an opportunity like this without him. Right. And so I knew one day I was going to be in that situation where if I did things right, I can turn around and create an opportunity for other people to get into real estate, build passive income, and do it in a way that makes my investors proud. And I was able to do that back in 2022 when I raised capital for the first time.
Justin Colby
So you are definitely the unicorn when talking about, like, your ability to go in with, like, you really know the rules, you really know the laws. You understand the risk. There's a lot of people that just want it because they want it. Oh, well, Carlton did I want it. They just don't know.
Carlton Dennis
Yeah.
Justin Colby
So I think the disclosure on that or disclaimer is just like, get educated. Call Carlton, understand, get a part of his program. Right. Because the reality is you just need to know what you need to know to make those decisions. I would argue it's not for everyone to go for the GP model 100 because they don't understand or know what Carlton knows.
Carlton Dennis
Yes. And one of the unfair advantages that I have that most people need to understand this is go sit down and talk with a tax professional. We get to see where the money goes. You cannot lie on your tax returns. And if you do, trust me, there's a whole department waiting for you.
Justin Colby
That's right.
Carlton Dennis
So I get to know the real, real when. When somebody brags about making a million or 2 million bucks online, I go look at the tax return and realize, no, they didn't. They didn't. 2 million bucks. They actually made 400,000 in profit. The top line says 2 million. You heard 2 million. The bottom line says 400,000. Their take home is 400,000. Please don't get caught up in everything that you're seeing online. When you talk to a tax professional, they can tell you what are the professions that are really making the money, who are the operators that are really doing it at the right scale and the right level? Because everything flows on that tax return.
Justin Colby
Now, I want to bring you all the way back to when you invested with Grant Cardone, your 6K.
Carlton Dennis
Yeah.
Justin Colby
I think there's a lot of people that would not have taken that risk. Why did you say, I got 11 grand in my name, I need to get in the game. I'm throwing 6k at this unaccredited fund. Why did you do that?
Carlton Dennis
Most people will invest with somebody else after they build trust with him. For me, I didn't know Grant Cardone. I had never met him before in my life. Never went to a 10x event? No. But did I download books? Yes. Was I listening to his podcast? Yes. Did I start getting some value out of his sales training? Yes. Was he talking about real estate? Yes. Was he bringing up other wealth teachers that I admired, like Robert Kiyosaki and how he bragged about not paying taxes because he was using the tax code in mind? Yes. And I was an aspiring tax professional. And to hear somebody that was advocating for the tax code whilst at the same time advocating for real estate, it was in perfect alignment with where I was in my training. I was just learning about the tax code and how you can use real estate as an investment and as a tax write off. And for me, I wanted to make mailbox money as soon as I could. I had that fixation of I'm going to live off of passive income, so I might as well start right now. I just didn't know what went into actually earning passive income.
Justin Colby
Yeah.
Carlton Dennis
And so because I did not know what actually went into earning passive income, I thought, well, I might as well partner with somebody who's already done this. I'll go put my money with Grant Cardone as a limited partner, knowing that I won't take on any operational risk and I get to benefit from the upside of him managing the property and him running the operation.
Justin Colby
Now, what was your mindset about the longevity play? You and I have talked about this on your podcast. My other podcast. Like, you didn't go in that for I'm gonna go get rich on a six thousand dollar investment?
Carlton Dennis
No, absolutely not.
Justin Colby
You went in with what? What was the mindset, the mo. Because what I want to get out of this is I want people to understand the young Carlton Dennis, who is not the man I'm in front of today, but was the young kid that's like, I deserve to create something amazing. And it's going to take some time.
Carlton Dennis
Yes.
Justin Colby
What was going through your head?
Carlton Dennis
Sacrifice, Sacrifice. Sacrifice, sacrifice. It took me so long to get on the playing field when I was a full scholarship cornerback at Cal Poly, St. Louis Obispo. And I worked and I worked and I worked and I felt like, you know, when you sacrifice, you get the benefits of it. Everything that I've ever really achieved in my life came on the other side of sacrifice and discipline. And for me, when I started learning about wealth, all the wealth, teachers, I mean, John C. Maxwell, Grant Cardone, Robert Kiyosaki, all of them were talking about patience. And it reminded me a lot of sports. It's like, dude, I can go into the gym and I can work my ass off. The muscle is not going to show up on my bicep that same day. It's going to take a month, two months, three months. It takes time to build a body, just like it takes time to build an investment portfolio. The issue we have right now, Justin, today, is that we're in a culture of I want money right now because of everything we see on social media. You have to realize back in 2015, 16, when young Carlton was just trying to invest, you didn't have all these people on the Internet, you know, jumping out of G wagons, running away from cars and splashing themselves with Saratoga. You know what I mean? Like, there was no great, There was no life like that for me to admire. There was no one that was making showing you that you log into this app, you're going to day trade this stock and make this much money. Nobody was talking like that like they're doing right now. People are talking about, go get a career, go all in on it. By the time you look up, you're 45, you're 50, and you're sitting on a mound full of wealth because you were disciplined. I was raised on old principles and those old principles is what got me here. Hard work, dedication, and having a long term vision of how you wish to build your wealth.
Justin Colby
If people could just understand, even when you have 11 grand, you just gave away like 56% of your net worth.
Carlton Dennis
Yeah.
Justin Colby
On maybe not risky, but on the point of I want to build something for the long term.
Carlton Dennis
Yeah.
Justin Colby
If you just Fast forward these 11 years or 10 years, whenever that was, to where now look what you're doing. You're putting a million dollars into a gas fund. People need to hear that story. They need to understand Carlton, young man, broke 11 grand to his name, still put in 56. Almost 60% of his neck. Is that right?
Carlton Dennis
Yeah.
Justin Colby
Yeah. About 60 of his net worth.
Carlton Dennis
Yeah.
Justin Colby
Net worth into this because he understood the long game is where it's at.
Maintain X Announcer
Yeah.
Justin Colby
Anything change about your mindset today when you invest today?
Carlton Dennis
Yes.
Justin Colby
What do you think? What do you go through? Why do you make the decisions you make in your investment strategies?
Carlton Dennis
The things that I do now is thinking about my daughter. Because now I'm a father. Everything that I was doing was about how do I. How do I invest money that's going to serve Carlton's lifestyle? Because I have a very, you know, lovely lifestyle. I like a lot of nice things. And no, I'm not going to change who I am. I'm very disciplined in how I approach wealth and how I approach my investments. But I also have expensive taste. I will order the wagyu on the menu. If they ask me what champagne, I'm going to ask them which one came from France. I'm just that type of person.
Justin Colby
Yeah.
Carlton Dennis
That being said, I got more and more focused about who am I really building this wealth for. And I'm not saying that I'm building this wealth just to give it to my daughter. I want to have options. And what most people don't do is they don't think with the end in mind. Like we talked about earlier, If I know that I'm not going to live on this earth forever, my options are going to become less important to me, and it's going to really shuffle to my daughter and to my wife. I want them to have options. I don't know if tomorrow I get into a car, God forbid, knock on wood, then I'm going to get hit by a bus. But I want there to be things set up so that my wife has options in the event that Carlton's not here anymore, that she knows what to do, how she's being taken care of. Everything that I was doing was really serving Carlton early on as an investor. How is Carlton going to make this type of money? So Carlton can make this type of money? And it was partly because over time, I started receiving information from the Internet, and the Internet started telling me what success was. And instead of looking internally for what my answer of success was, I started letting the Internet tell me what success was, which was, oh, you just need to go accumulate more assets. You just need more stuff. And So I started playing this stuff game until my wife got pregnant and everything changed. Bro, I tell people this all the time. You know, you think you love somebody when you have found your person. Me, my wife, we love each other to death. She's my best friend. You think that's the most you can love somebody outside your mother or your brothers? I kid you not. The moment I laid my eyes on my daughter, bro, I swear it was like a river, like the Amazon river flooded into my heart. And you have a special place in your heart that is literally only reserved for kids. You cannot even unlock that place in your heart until you have a child. Yeah, once that happens, it's like the genome inside your body changes. Man, I stopped seeing the entire world the way that I was seeing it.
Justin Colby
Yep.
Carlton Dennis
I had newfound respect for my mother, newfound respect for my father. I cared more about just being slow and, and spending time and listening to the birds chirp and smelling a goddamn flower than do I care about being on a plane, flight, jumping on a podcast, going to do this, going to do that. My, my, my values changed. And then my values poured over into my investment philosophy. I stopped making decisions that immediately benefit Carlton, but benefit the household.
Justin Colby
Yeah.
Carlton Dennis
And what over time is. My happiness started to come from my ability to serve in the connections that I was making with people less about what Carlton was doing for himself.
Justin Colby
So when you invest today, how are your entities structured? How are you doing for that purpose? Right. Versus just cash flow or type? Like how do you set up the entities for your wife, for your children today?
Carlton Dennis
Yeah, so I run a whole co structure. Everything operates as C corporations for me. We have a high profit business in tax advisory. Plus I have a family office company. So my C Corp is a holdco that owns all my operational cos. Everything flows up to that C Corporation and it operates like a single family office. That family office has its own management structure, HR structure that disseminates across every single operational co. I have an S corporation that does consulting to my C Corp. You might ask why. It's because I don't like paying double taxation with the C Corp. So my C corp pays my escort, my escort pays me.
Justin Colby
That's right.
Carlton Dennis
My S Corp allows me to take distribution. So if I want to go buy real estate randomly today, or go buy crypto randomly today, every time I pull money out of a C corp, I'm taxed at dividend rates. Every time I transfer money from a C corp to an S corp, well, that's a management fee. My C Corp receives a Tax deduction. Now with my S Corporation, I'll take a distribution. I'm not taxed on that distribution when I took the money. And I can go park that into an investment that earns me a return while simultaneously being able to draw down my tax liability inside of my parent company. This is what we call entity layering. And for most people, when you're starting out, you don't even need to worry about having multiple entities. You just need to figure out your first entity. But over time, the things you care about will start to change. Your exit strategy will start to become something that you care about, depending on the size of your business, your employment, and lowering cost. I'm well over 60 employees, so the way I run my structure benefits my entire ecosystem. I have much more favorable rates from my health benefits and all the stuff that I provide my employees by running my operational code the way that I do. And more importantly, I have leaders now that run these businesses instead of everything. All roads lead to Carlton Dennis. There's operators at every level and allows for me to be able to do what I do best, which is media and being the magnetic energy that allows for all these businesses to feed off of each other.
Justin Colby
So when you have your S corp that gets the distribution and you're going to go invest in an apartment with me, is it Carlton Dennis investing in an apartment, Is it an llc, another S corp who's investing with me in my apartment?
Carlton Dennis
Yeah. So my wife and I, we invest together. Part of the reason why we do this is because she qualifies as a real estate professional. So we have an investment LLC that's specifically set up for us to do investments together. If I'm going to go invest with you, I'll probably come on as an lp, depending on my relationship with you and how much capital I'm coming to the table with. But I'll most likely come on as an lp. So I have that investment LLC that will invest inside of your llc. Got it. The reason why I do that is because I prefer to have partnership entities. Partnerships file their own tax return and then that tax return flows a K1 into the individual tax return. Not to say that, you know, that's bad to invest as an individual inside of that LLC. It's not like I'm not going to get a K1, but I really like to do things inside of partnerships and limit things on my individual return as much as possible because it does reduce audit risk. Partnerships and S corporations are audited on average around 30 to 35% less than schedule. C businesses. So I try to do everything through partnerships or S corporations to try to keep as much activity off of that individual tax return.
Justin Colby
Assuming that LLC gets funded by you personally.
Carlton Dennis
Yeah. So if I'm taking a distribution from my S Corp, then the distribution is going to flow from my business checking account to Carlton Dennis, from Carlton Dennis as a contribution to Carlton Dennis's investment llc. And then that investment LLC makes an investment into the property.
Justin Colby
So I hope you guys all fight because I'm very understanding what he's saying, but might want to rewind that. This is good tax now, by the way, I don't know if we can even promote this, but there's going to be a live event coming up. I'm going to be speaking at. But, but I think if, if this creates questions for all of you listening, first and foremost, go follow Carlton. But also like, is that an event, something we should talk about? Like, because I think people need to get in front of this because they just make investments. I have so many investors like, oh yeah, John Doe is going to make the investment. I'm like, oh, what entity? No, just me. And I go, okay, well, I'm not going to sit here and give you financial advice per se. Maybe you have a reason to do that. Right? But I think people need to understand this, like what's on your desk, that they can start to research some of this stuff, whether it's a product, a group, a live event, what can they go start to get educated with taxes
Carlton Dennis
is one of those things that you are going to learn it the moment you decide that you are ready to submerge yourself into just knowing more. If you can commit, you can learn tax strategy. But if you put one foot in, it's going to be an uphill battle for you. So we put on an event called the Tax Free Millionaire Summit where taxpayers can spend three days with us going over advanced tax strategy, asking questions and really understanding all the frameworks that we leverage. Whether it's entity structuring frameworks, income shifting, placing children on payroll, or alternative strategies like oil and gas, gas stations, you need access to the right information broken down in a way that you can actually understand it. Most people don't act on tax strategies. It's not because they don't have access all the time. It's because something has not been explained to them in a way in which they fully understand it.
Justin Colby
That's right.
Carlton Dennis
The Tax Free Millionaire Summit allows for that.
Justin Colby
So if you follow me or follow Carlton, Carlton will be in the more club. By the way, so we'll get him in there to start giving some pieces of advice because ultimately, the more, you know, the better you can become investors. Right. And so he's my guy that I go to for tax advice. He will be in the club. If you're not in the club, make sure you get in that club. The more club. So now let's go fast forward your investing today.
Carlton Dennis
Yeah.
Justin Colby
Because of your kids, because of longevity. What is your thought process of how you're going to leave it to them? Hopefully you live another 78 years, which would put you at 110ish.
Carlton Dennis
Yeah.
Justin Colby
Yeah. You know, and you probably will. You and I will probably be somewhere in Bimini with, you know, with our. With our wives and kids because, well,
Carlton Dennis
you got to go check out Bimini.
Justin Colby
Bimini. So how are you looking to leave all this? Right. As you start to make these investments, what's the purpose? You and I have just talked a lot about. Like, I start to ask why, why, why? For everything I'm doing now.
Carlton Dennis
Yeah.
Justin Colby
Because I don't believe in a lot of the nonsense of this world. The older I'm getting, I'm really realizing, like, I need to have contentment and happiness. Yeah. So why am I doing it? Why am I investing in this? Why do I have this business? Why? So when you are doing this, how are you leaving it to your family?
Carlton Dennis
You know, I had a conversation with my team about this, and my heart has changed. You know, originally my mindset was build up wealth because you want to be able to leave it to your children. But. But I've seen so many children that have inherited wealth that have done nothing with the wealth. And more importantly, their brain is like literal mush because they were just handed everything in their life that they can't even think for themselves.
Justin Colby
Yeah.
Carlton Dennis
I believe wealth is really the transfer of information, not just the transfer of assets. And my happiness is not going to come from me just transferring information is going to be. It's going to come from me knowing that I worked my ass off to build up enough assets that are going to be permanent assets in our family, assets that will live on legacy assets. And I'm structuring my trust. Trust, plural, irrevocable. And irrevocable trust to mitigate estate planning taxes for my daughter and for the children that might come directly after her, but putting clauses in my trust that allows for them to have access to certain wealth at certain points in time. I know for me, I'm 32 years old. I would say I'm at the Point right now based off of the work that I put in where I feel very comfortable making financial decisions. But I put in a lot of work. And I'll be honest with you, my daughter's not going to have to put in as much work as I did to get the level of information that I have access to. That is what I'm working so hard for. So if she can have access to information, great. I want her to have access to information early. I don't want all the dramas that come with having access to money too early. And my biggest thing is about pattern recognition. How can I teach my daughter to recognize patterns so she can adopt things, activities, behaviors that can allow for her to be a full hearted, God fearing, successful woman. And that's what I care about the most. So for me, I believe that the money part, it's probably not going to come for majority of my children who inherit it until 35 years old. That's the number that me and my wife have decided if they're going to receive anything, they'll receive it when they're 35. And we have a 60, 40 rule, which is 60% of all the wealth that me and my wife create together is our wealth. 40 is going to be left over for whoever is there at that point in time.
Justin Colby
So I like that 6040 rule. I'm not. That's the first time I've heard that, which, you know, listen, I've. I've bounced back and forth between like, do I want to give them anything? And I think it's a little aggressive to say I wouldn't give them anything, but like, I want to live a good life while I'm here too.
Carlton Dennis
Yeah, of course.
Justin Colby
And I think I'm not going to judge anybody, but I think the people that like hoard it all and they don't do, and they don't use it. Me and my wife had a conversation literally last night about like, while we're here, we're gonna spend money. We're not gonna cheapskate. We're not. Now you can still do that in a way that is smart. Right. And understanding taxes and understanding what you're spending money on. And, and I've seen stuff where you've talked about taking vacations that are business trips and, and things of that nature. Because yes, it's a business trip. I need to go see this apartment we're about to go buy in Phoenix, Arizona. So I gotta go to Phoenix, Arizona. I gotta go walk this property. Right, right. All these type of things. But I think it Is it is great to hear that you'd say, let's just use $10 million. You're gonna spend 6 million of it for you and your wife to actually enjoy life while you're here, too.
Carlton Dennis
Yeah.
Justin Colby
Because we only get one life.
Carlton Dennis
I'll be unapologetically okay with that because at the end of this day, we, We've. We've seen what it's like when people have worked so hard and then never turned around and, and got to allow for that hard work to be something that they benefited from. Life is short. And as much as, you know, I don't agree with his business model, the guy that created only fans, I believe.
Justin Colby
Oh, yeah, they just did a documentary about his death or something, right. 40, 44, I think. My age.
Carlton Dennis
44 years old.
Justin Colby
Yeah.
Carlton Dennis
Drops dead, right? Drops dead.
Justin Colby
Yeah.
Carlton Dennis
I. I don't know if he's. He might be a bad example. He probably didn't enjoy a lot of, I don't know, all the things he was enjoying. But what I'm trying to get at here is, brother, we don't know how long we're gonna be on this. On this earth. Right. So for me, it's like, I bought the Lamborghini because I don't want to get into a Lamborghini at 55 years old having a crouch. Personally, I don't want to. Right. But I like the fact that I'm driving it right now. It's not to say I'm going to be driving it forever, but I spent the money. The experience happened. The experience got absorbed. I believe God wants me to have these experiences. I don't think that God put me here to just sacrifice. Sacrifice, Sacrifice. Just work, work. I know God worked, but I also know God enjoyed experiences, too. He was serving every single day, but you can't tell me he wasn't enjoying what he was doing.
Justin Colby
I think it's important to find that contentment because it doesn't matter whether people judge you or not. They're going to judge you. Whether you drive a Lamborghini. Drive toy. They're going to say you're broke or you're rich or you're all about money. It doesn't matter. Go do the thing that makes you happy.
Carlton Dennis
Yeah.
Justin Colby
I have found through spending a lot of money on things that don't actually bring much value, my happiness faded.
Carlton Dennis
Yes.
Justin Colby
And so I'm getting to the age where I realize, okay, if I buy this expensive thing, I know my happiness is going to fade over time. So do I really, really want that thing like 100. So now to me, I connect things like this watch was when my daughter was born. My other watch was when my son was born. I literally connected to a meaningful moment that you can't take that fate. It never fades.
Carlton Dennis
Yes.
Justin Colby
It doesn't go anywhere. Right. And so that's my way of, of justifying it. The older I get, I want to lean into this idea of real estate creating this longevity. So for example.
Carlton Dennis
Yeah.
Justin Colby
Apartments, I'll use that because that's my vehicle of choice. But over next 20 years, if someone invests 40 grand in these apartments in 1031 exchanges, they're going to be making close to a hundred thousand dollars a
Carlton Dennis
month tax free in a 15 year time frame.
Justin Colby
Did I say 15 or 20? 15 is closer to 70 grand a year. $68,000 in 15 years. Yeah, 40 grand a year every single year. Compounding 1031 ing 15.
Carlton Dennis
What you just said, it's compounding. That's right.
Justin Colby
Because you never take it out.
Carlton Dennis
Right.
Justin Colby
And so it compounds. And so when someone passes, can that income be passed off to their children tax free? I know there's a step up basis in valuation of the actual net worth and valuation. How does that look to the children? Because then I would say, why wouldn't everyone invest in any type of compounding dividend that goes forever? Because that is the fastest way, I would argue, to go, leave your children something of value and they don't get it until you pass. Because then you leave them this 70 grand a month of income that they're going to inherit.
Carlton Dennis
Yeah. Two reasons. One, uneducated, they don't know what step up in basis is or they've heard about it and don't really fully understand it. And two, they are lazy. They hear about something and like, okay, well one day when I'm rich or when I have time, I'll go.
Justin Colby
That sounds nice. That's for you.
Carlton Dennis
Those are for wealthy people. I mean, why would I focus on that structure right now? I must have to have all of it already figured out in order to. In order.
Justin Colby
Remember Carlton gave six grand out of his 11 grand net worth starting because you got to start somewhere.
Carlton Dennis
Yes.
Justin Colby
So talk to us about the step up basis so people can be a little bit more informed about that.
Carlton Dennis
Yeah.
Justin Colby
And then my actual genuine question with not being informed that I don't know if I'm making 70 grand a year tax free and I pass because I have all these apartments, does that, is there an ability to pass on the cash flow to my children tax free?
Carlton Dennis
The cash flow is still going to be taxable income to them every single year. They'll have to report it.
Justin Colby
But if they were, now they net 40 grand a year or 40 grand a month. That's a pretty nice little gift.
Carlton Dennis
That's an amazing gift.
Justin Colby
What?
Carlton Dennis
That's an amazing gift. Yeah. So they'll still, they'll still pay taxes on whatever the cash flow is, but the asset, the, the ownership, if they were to sell their interest and being a part of your, you know, fund or syndication structure that determines whether or not they're going to pay capital gains taxes. We Talked about the 1031 exchange, which is an IRS rule that allows for you to transfer your capital gains and your cost basis into a new property that's equal or greater than value. You're essentially kicking the can down the road, the tax can, if you will. And the rule exists because if you're a real estate investor, the government wants you to stay in real estate. They want you to continue to buy, to buy properties or provide affordable housing. So they're going to incentivize you to stay in real estate with the 1031 exchange strategy. So what happens if you end up dying and you've done 5, 10, 15, 1031 exchanges going back to when you were 40 years old? Well, if you have a trust in place and your children are beneficiaries of that trust, they may receive a step up in basis, which means that the ownership of the assets that they're receiving is going to step up to the fair market value of at the date of their parents death. So if their parents got in with a basis of a million dollars, and that basis is now $15 million, well there's a $14 million gain that the children are going to have to experience. If there's no step up in basis in place, there's no trust, there's no estate planning that was done. Most taxpayers don't want their children to be dealing about their loss and mourning over their loss and at the same time trying to figure out how to sell assets to pay the taxes associated with the, the estate that they inherited.
Justin Colby
No doubt.
Carlton Dennis
So if you can do proper planning ahead of time, you can establish a revocable living trust. Your children receive the step up in basis and now they inherited an asset tax free. Let's make it simple. Imagine you bought Apple stock for a hundred dollars and now Apple stock is trading at a thousand dollars. That's a 900 gain. And your children inherits the stock. Well, guess what, they're going to pay taxes on that 900. If there's no trust structure in place with the proper struct structure or will establish, your children can establish or receive step up in basis. Meaning now when they inherit that Apple stock at $1,000, they can sell it with absolutely zero capital gains. Now just multiply that number by 100,000. And that's the type of wealth that we're talking about in the grand scheme of things. For some taxpayers.
Justin Colby
I think this should start to. I'm hoping this episode lights a light bulb in people's head. You and I invest in these passive assets for somewhat different but similar reasons is we make money in a model that is not reliant on the passive income model.
Carlton Dennis
No.
Justin Colby
Okay.
Carlton Dennis
That's correct.
Justin Colby
I think people need to remember you still need to put gas in the car. That gas is your income.
Carlton Dennis
Yes.
Justin Colby
I don't care if you're W2, I don't care if you're an entrepreneur. Great. Keep making the gas. Because over time, over Runway the 10, the 15 year old Carlton making putting 6 grand in this deal gave himself enough Runway that if he did this every single year, which now you've well surpassed that, you're going to wake up one day and start having 70 grand a month. 80 grand a month, 120 grand a month passively. But you're also going to have this huge net worth that was driven by the gas you put in the tank. And now you have choices.
Carlton Dennis
Yes, you do.
Justin Colby
Do you need gas anymore or not? I don't know. You're a call, right? Like is it really worth it? Does it create your happiness and you've built over time. I'm 44. I believe I will be living to 100.
Carlton Dennis
Yeah.
Justin Colby
In the next 30 years I can literally create a six figure a month income that's tax free. And I'm going to be able to give that. Now they could pay taxes on it, but they're still going to be making 60 grand a month.
Carlton Dennis
Yeah.
Justin Colby
Tack that 60 grand tax free to them. Plus they step up the cost and whatever the hell I'm in, in 30 years I won't even have an idea right this second. And they're going to say, oh great, I'm going to take my 180 million dollar portfolio my dad just essentially gifted me because of his trust and we're going to sell it. How much, how much taxes are they going to take if I set it up with the right trust system?
Carlton Dennis
Yeah.
Justin Colby
And they are the, the executors of the trust. Yeah. How many on the $180 million of real estate and they sell it, you're
Carlton Dennis
going to pay quite a bit of taxes because depending if your, your parents are married or if you're married, when you inherit an estate like that, you, you may only get a 15 million or a $30 million exclusion. So if you're inheriting a huge estate like that, you would have hoped that your parents put some of that real estate into an irrevocable trust and kept some of it properly in a revocable trust. The reason why I say this is because the irrevocable trust takes assets out of the estate for the purpose of eliminating estate taxes. You become a beneficiary of the irrevocable trust and because of that you don't have to worry about capital gains taxes. But the downside is you get no step up in basis on the assets and irrevocable trust. But what if your parents identify the right assets to leave in the revocable living trust keeping you under that 30 million? Maybe you have the right type of assets in that revocable trust that you do want to get the step up in basis in keeping you underneath that 30 million dollar threshold. And then everything else goes in the irrevocable trust that you still inherit that prevents you from owing estate taxes. So this is a situation where having two trusts matter a lot more than having one trust. Which is why estate planning ahead of time is very powerful.
Justin Colby
This is game. This is why you guys need to be in this club, the more club. Because men like this are going to be in there. By the way, you have a book either, it depends on when this launches. It's either out on Amazon.
Carlton Dennis
Yeah.
Justin Colby
And if it's not out yet, it's coming. Let's talk about this book real quick.
Carlton Dennis
Yeah, we have the book called the Art of Legal Tax Avoidance. And it's so funny that you talked about not quitting your earned income job because we address that in chapter two do. I'm not telling taxpayers that, you know, just because real estate provides the best tax benefits. Quit your job, go start a business, go invest in real estate. No, I'm telling you to do that right, right alongside your earned income. We don't want you to abandon your earned income. What we want to do is we want to leverage your earned income to get into assets that can turn around and offset your earned income so you can get to retirement faster. I'm all about compounding. And your ability to invest early and often is what's going to get you to freedom sooner rather than later. But if the tax code is working against you, or sorry, if the taxes are working against you, what are we doing about your biggest expense? If you have no strategy to try to offset your biggest expense, then your goal is to just work more and try to invest more. That's a very defeating, defeating play because every hour that you work more, you're trading 37 cents on the dollar to Uncle Sam. Whereas if you're smart and you're a savvy taxpayer, that number might be 10 cents or even less. Like real estate, where a lot of real estate investors are paying close to zero percent in income taxes. So before you can get there to where you're paying 0%, you have to figure out your investment vehicle. For most taxpayers that are working full time jobs, they love the idea of real estate. Once I tell them how the strategy works, then it comes down to a little bit of management. We manage the real estate, we start benefiting from the cost segregation study and now we have big refund checks coming back to us if we're W2 or we're avoiding big tax payments if we're self employed.
Justin Colby
Now this book is either out on Amazon now or will be depending upon when this launches again. What was the name of the book?
Carlton Dennis
The Art of Legal Tax Avoidance, Volume one.
Justin Colby
There you go. Now you also need to go follow this man all over social media. He is massive. He is the go to. He is my guy that I go to for this stuff. So if it's good enough for me, it's definitely good enough for you. As you're here listening and watching this, go to his YouTube, go to Instagram, go to TikTok, Carlton, Dennis, any other names on any of these channels that they needed put in there? Tax Alchemy. Go look at Tax Alchemy. I'll just plug you because how great you are and all things. What else? We have a live event in.
Carlton Dennis
Yeah, yeah, we have a live event coming up in, in June for our private client group members. And you know, if you're somebody that like likes to come in person to learn tax strategy, it's definitely an event I'd have you reach out at. You can go to WW tax alchemy.com to get more information. If you're somebody that's an avid learner, the book is going to be a great resource for you. I know it was for a lot of our taxpayers that have already read it. It's called the Art of Legal Tax Avoidance. You can go to the artoflegal taxavoidance.com to download your copy today.
Justin Colby
There you go. That's it. Carlton Dennis, it's been a pleasure.
Carlton Dennis
My bro, Justin Colby. Thank you so much.
Justin Colby
We're gonna do a lot. All right. That is Carlton Dennis. I am Justin Colby. This is the More show and again brought to you by the More club where you will see and meet and talk to Carlton Dennis himself. Make sure you're a part of that club. We will see you in the next episode. Peace.
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Episode Title: Did you know the Tax Code Is Designed To Make You Rich, If You Know How To Use It?
Guest: Karlton Dennis (Tax Strategist & Real Estate Investor)
Host: Justin Colby
Date: May 21, 2026
In this engaging episode of The MORE Show, host Justin Colby sits down with renowned tax strategist and real estate investor Karlton Dennis to unpack the hidden wealth-building opportunities inside the U.S. tax code—especially for those leveraging real estate investments. Dennis delivers practical strategies, candid stories, and in-depth education on how both new and experienced investors can use the tax code to accelerate wealth, protect their assets, and plan for generational legacy. The conversation moves from foundational principles to advanced tax and estate planning strategies, keeping a relatable, high-energy tone throughout.
On Patience & Sacrifice:
"Everything that I've ever really achieved in my life came on the other side of sacrifice and discipline."
— Karlton Dennis (16:40)
On Tax Code & Gas Station Investments:
"Gas stations depreciate over 15 years... you can take a bonus depreciation and write off the entire purchase price... in year one."
— Karlton Dennis (04:56)
On Legacy & Information:
"I believe wealth is really the transfer of information, not just the transfer of assets."
— Karlton Dennis (28:38)
On Step-Up in Basis:
"Your children can receive a step up in basis and now they inherited an asset tax free."
— Karlton Dennis (37:06)
On Choosing the GP vs. LP Role:
"You take on a lot more risk when you're a GP."
— Karlton Dennis (11:50)
"With GP, you get active deductions... that can go to offset your active W2 or 1099 income. As an LP, your loss is passive."
— Karlton Dennis (10:10)
This episode is a masterclass in demystifying real estate tax strategy and legacy planning. Whether you’re an aspiring investor or a seasoned entrepreneur, it delivers both actionable steps and the “why” behind true wealth-building.