Why Nobody on Your Team Has Mentioned Cost Segregation
Key Takeaways
- Many large real estate portfolios and wealthy family offices miss out on cost segregation studies not due to a conscious financial decision, but simply because the strategy is never brought to their attention by their advisory team.
- DJ Van Keuren notes that the primary reason missed tax strategies happen in family offices is an education and awareness gap, as advisors often focus heavily on risk and capital preservation rather than proactive tax planning.
- While bonus depreciation and cost segregation can add an extra 3 to 4 percent to an asset's return, about 80 percent of families still skip 1031 exchanges, demonstrating a broad need for proactive tax strategists within large investment teams.
- Cost segregation is generally not recommended if you plan on holding a property for only a short period of time, or if you sell without utilizing a 1031 exchange and face immediate depreciation recapture.
- Real estate tax benefits like depreciation and cost segregation should be factored directly into the acquisition underwriting model rather than treated as an afterthought.
Cost segregation is a real estate tax deduction many of the largest property owners never use. The reason has nothing to do with money. David Wiener, Mr. Cash Flow, sits down with DJ Van Keuren, founder of the Family Office Real Estate Institute and co-founder of Evergreen Property Partners, who has spent 25 years inside family office real estate. They cover why a cost segregation study so often never reaches the people who make the decisions, who actually brings a new tax strategy to a wealthy family, why DJ's annual family office study finds about 80 percent of families do not do 1031 exchanges, how 100% bonus depreciation changes the math when a deal is underwritten, how depreciation recapture works when you sell, and when not to do a cost segregation study at all.
Built for the real estate investor who assumes a bigger portfolio means better tax planning, the business owner who owns the building the company runs out of and has never had anyone look at it closely, and the tax professional who knows how cost segregation works and wants a 25-year view of how these conversations start inside a family office, and who starts them.
WHAT YOU WILL LEARN
Why a missed cost segregation study is usually an oversight, not a decision, and who is most likely to raise it
How wealthy families pick advisors by trust, and why a bigger team can mean fewer tax strategies reach you
The five types of family office real estate investors and which ones have someone watching for cost seg
When not to do a cost segregation study: a short hold, a sale without a 1031 exchange, losses you cannot use yet
Why tax benefits belong in the real estate underwriting model, and how depreciation recapture works on the way out
CHAPTERS
00:00 Same tax code, different outcome: why big real estate owners miss cost segregation
03:03 What is cost segregation? 27.5 and 39 years vs 5, 7, and 15 year property explained
04:39 Why family offices underuse cost segregation, and what the callers asked
05:56 Missed tax strategy: a decision or an oversight? Who wealthy families trust
09:20 The five types of family office real estate investors and who handles cost seg
13:18 How many families skip 1031 exchanges and opportunity zones
18:24 When not to do a cost segregation study: short holds, small properties, passive losses
20:30 Bonus depreciation in the underwriting model: how tax benefits change real estate returns
24:26 Depreciation recapture, 1031 exchanges, and why cost seg cannot fix a bad deal
29:24 Your cost segregation playbook: the question to ask your tax professional this week
Nothing in this episode is tax advice for your situation. Your numbers are your numbers and they need a professional who knows them. Tax evasion is a crime, but tax avoidance is mandatory.
Your host: David Wiener, "Mr. Cash Flow"
David.wiener@cashflowstrategies.us
770-224-8504x2
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Frequently Asked Questions
What is a cost segregation study?
A cost segregation study is an engineering-based analysis that breaks down a building's purchase price into individual components like 5, 7, and 15-year property, allowing investors to accelerate depreciation instead of using the default 27.5 or 39-year timelines.
Why do wealthy family offices often miss out on cost segregation?
Family offices frequently miss out on cost segregation because their primary focus is strictly on risk mitigation and capital preservation, and their trusted advisors often lack specific awareness or deep real estate tax specialization.
When should you avoid doing a cost segregation study?
You should generally avoid a cost segregation study if you are planning a short-term hold on the property, intend to sell without executing a 1031 exchange, or have passive losses you cannot currently utilize.
How does bonus depreciation impact real estate underwriting?
Incorporating bonus depreciation and accelerated recovery periods into your underwriting model can significantly boost overall property returns by lowering early-year tax liabilities and increasing cash flow.
David Wiener: Two owners, same tax code, same kind of buildings, completely different outcome. The first one bought a short-term rental last spring. It's her very first property. She heard about cost segregation on a podcast, called somebody. A trained professional walked the property and the deduction showed up on her very first return. The second one owns a portfolio. Industrial, multifamily, couple of office buildings. There's a family behind it. And around that family there's a team, a tax professional, a wealth manager, an attorney, somebody running the investments full time. Nobody on that team has ever run a cost segregation study on a single one of those buildings. Not because they looked at it in the past, because it never came up. And that's what I want to understand today. My guest has spent 25 years working with families like that second one, and he's going to tell us how a strategy actually reaches a family And why this one so often doesn't. Welcome to the Tax Strategy Playbook. I'm David Wiener. People call me Mr. Cash Flow. And this show is to help real estate investors, small business people, and tax professionals learn more about the tax code and what can keep them from overpaying their taxes. My dad was a CPA and he used to tell me that tax evasion is a crime, but tax avoidance is mandatory. Here's what you're going to be able to do by the end of this episode. You'll know how a tax strategy actually travels to a property owner, who raises it, who doesn't, and why that has almost nothing to do with how much property you own. You'll understand why a big team around you can actually mean fewer strategies reaching you rather than more. That's the idea we're turning over today, and it catches people off guard. And you'll leave with one question to ask your tax professional this week. If you own rental property, stay with me because the Reason the biggest owners in the country miss this is the same reason you might, and it has nothing to do with money. If you own a business and you own the building, it operates out of, that building is probably the asset nobody on your team has looked closely at for years. And if you're a tax professional, you already know how cost segregation works. What you may not have seen is a twenty-five year view of how these conversations start and who starts them, and that part is worth your time. My guest today is DJ Van Keuren DJ is a co-founder and co-managing member of Evergreen Property Partners in Denver, a real estate investment platform for family offices. He's the founder of the Family Office Real Estate Institute and the president of the Harvard Real Estate Alumni Organization, which he helped found in 2009. He spent twenty five years on the allocation side of real estate for single family offices, including Heyman, Arsenault and Jane family offices. DJ, thanks for coming on.
DJ Van Keuren: Thanks for having me.
David Wiener: I'll tell you why I wanted you here today. Most people who talk about this on a podcast are explaining the strategy. You spent 25 years on the other side of it sitting with families while they work out what to do with a building. That view is rare and I don't think anybody's ever asked you about it. So before I ask you anything, give me 90 seconds so everybody's understanding the same thing. Then I'll get out of the way. When you buy a building, the whole purchase price gets depreciated over one
DJ Van Keuren: Thank
David Wiener: long life by default. Residential rentals run twenty-seven and a half years, commercial runs thirty-nine years. But a building isn't just one thing. It's a lot of things put together. Carpet, cabinets, specialty electrical, the plumbing that serves the equipment instead of the structure. Outside you've got paving, curbing, site lighting, landscaping. Under the code, a lot of that isn't building at all. It's considered personal property and land improvement, and it carries a five, seven, or fifteen year life. Cost segregation study is the engineering work that finds those components and prices them. And here's the part I always say engineering based studies are the only kind worth doing. Not a desktop estimate, not a percentage rule of thumb. An engineer looking at the building with a trained professional who takes the pictures. That's the strategy. If you want the full version, episode two builds it from scratch. Episode 20 covers the myths, episode twenty four is the audit documentation. DJ, that part I can handle. What I want from you is everything all the way around it. Back in twenty twenty two, you said publicly that family office is underused cost segregation, and you said that the phone rang after you said
DJ Van Keuren: Okay.
David Wiener: it. I wanted to know for a while what those callers were actually after. What were they asking you?
DJ Van Keuren: Well, I'll tell you, how that came about too is I had been sending out emails, just educational emails, on a monthly basis. And I'll get some responses occasionally, but when that information about cost segregation went out, the phone just rang off the hook. Families were calling me and they were asking me, okay, what exactly is this? And how does this work? yeah,
David Wiener: I've heard that question before.
DJ Van Keuren: and so, you know, it's a matter of, you know, the best strategy in the world doesn't matter if it never reaches the decision makers, right? And if they don't know about it. And that's exactly with cost segregation. mean, there's various, in some capacity, I mean, everybody owns real estate, right? Even if it's your home. But for families, it's the second largest area of wealth creation outside of where they created their initial wealth.
David Wiener: So when when the phone started
DJ Van Keuren: Hmm.
David Wiener: ringing, who was on the other end? Was it the family itself or was it somebody who was advising them?
DJ Van Keuren: It was primarily the patriarchs that were calling and the actual primary decision makers.
David Wiener: Here's the question I keep coming back to. When a family doesn't run a study, is that usually a decision somebody made or is it usually just nobody put it in front of them?
DJ Van Keuren: It's the latter. People didn't put them in front of them. And, you know, I think it goes back to really understanding the where families and our definition is families, family offices worth 250 million or more. And when I say this, it'll probably make sense. But, you know, I made the mistake the first three months in working in this space and I thought here you have very successful people. have people that are very wealthy, that are tied in, et cetera. But they've spent the last 40 years, let's say, chemicals or tires. And all of they have all this money that comes in. They don't understand hedge funds and real estate and venture capital when private equity Right. And some people spend their whole life not only just in venture capital, but health care venture capital, not just health care venture capital, but middle market. Right. So you can't assume that, which I did initially, that they understand everything. Right. From A to Z. And so.
David Wiener: Or that somebody's telling them about it.
DJ Van Keuren: Well, here this goes to my next point. So somebody gets a huge amount of money, hundreds of millions of dollars, 100 million. whatever that number is. Who do you think is the first person that they call when they're sitting on all this money? If you had to guess, who would you guess?
David Wiener: I'd say they're CPA.
DJ Van Keuren: Well, you'd think, especially if they built a business that they'd hire, they'd look for the very best person that's out there, right?
David Wiener: Sure.
DJ Van Keuren: The reality is, who do I trust? So it might be the CPA, but it very well may not be. It could be their neighbor who ran a business. It could be their financial planner. It could be their attorney. At the end of the day, it comes down to who do I trust will make good decisions and try to help me with what I'm doing? Now, I would say 95 % of the people fall into the family office space because of that, but guess what? That person that they hired, they don't understand venture capital and real estate and private equity and hedge funds, right? And this whole
David Wiener: Right.
DJ Van Keuren: thing. now you've got sort of, in some ways, I don't want to say the blind leading the blind, but you have people that don't know, who are very intelligent, but just... don't have the information about everything.
David Wiener: In some ways it is kind of the blind leading the blind.
DJ Van Keuren: Well, I'll tell you, it's really interesting. there are three things that I was told every time I worked for a family, and that was, don't lose money, don't lose money, don't lose money. Right? And
David Wiener: I get that.
DJ Van Keuren: a lot of the, if there is an investment committee, which isn't always the case, but usually, regardless, the focus is on risk. right, and returns. Tax strategy is offered and reduced later than it should be. And so it's a
David Wiener: When
DJ Van Keuren: matter of where can we put the money, where we can keep it safe, because they're not going to receive that money again.
David Wiener: Yeah. When when something like cost segregation comes up, who who's the one who tends to bring it? Somebody in the family or somebody on the team?
DJ Van Keuren: You know, that's a good question. And if it does come up, it's typically, if they're allocating to, well, let's go back here first because there's five different types of real estate families. So you have the families that created their wealth in real estate, A Trump or other people, I mean, that's their whole career. They're going to understand cost segregation because that's their business that they're in every day, right?
David Wiener: Right.
DJ Van Keuren: The second type of investor for a family office real estate is the Michael Bloomberg, the Bill Gates, the Michael Dells. And they have so much money they have to get out that they'll write a minimum check of $20 million. But they're going to hire the institutional people that worked for a Blackstone or a Goldman Sachs to come in. Now, they may not necessarily understand cost seg either, but they're going to usually have their own real estate department. So most likely, it's probably the case. The third kind is the family that says, look, we want to own our own portfolio. So we're going to go outside and we're going to build up a bunch of properties. And maybe they hire a property manager. Maybe they've hired an asset manager, right? That internal CIO is usually the person that we were just talking about. Or maybe they helped with their business, right? The fourth kind is a family that says, I don't necessarily have their infrastructure, but I'm going to allocate. So I'm going to look for joint ventures. I'm going look to go direct on deals. And I'm going to provide money to sponsors and operators. And typically, those operators will take care of cost seg for the most part. And then the fifth kind has zero infrastructure in place. So they're going to typically go into funds. they still may have a bunch of their own real estate, right? And as well as the top three for sure, or I'm sorry, the last three I mentioned has their own real estate. And the one that I mentioned that builds their own portfolio, they don't necessarily have, remember, let's say the CFO is now taking over their family office information, they may not know cost segregation, right? And so a lot of times it get bypassed and that is just purely from a knowledge, education, and awareness perspective.
David Wiener: I you know, I've learned over the years that I've been doing this that there's a huge education gap out there. People just don't I mean it's becoming more and more and more popular and more and more and more mainstream now. I remember the days when I heard cost segregation and I thought, what the heck is that? You know, and now I've been traveling all over the country trying to educate people on what it is and how it works and and those kinds of things. But you don't always get in the in the kind of groups that I'm teaching, either it's a group of CPAs or it's a group of real estate investors. But your high wealth investors don't generally show up at those meetings. You know, so if let's say somebody is is talking to their to their team, their their family office team, and they bring up the idea of cost segregation, because they heard about it somewhere. They they listened to the tax strategy playbook and they found out about it. W what has to be true for it to go anywhere and if it stalls, where does it usually stall?
DJ Van Keuren: You know, it really comes down to understanding. So if somebody brings it up, now it's on the radar. So it's a tax benefit, right? And something, it's a tool that you can use. So by all means, they're going to say, explore that, find out, and let's get some information and see if it's applicable for us, and then how do we implement that? It's a matter of, it's not a case of saying, Let's move forward. It's a case of somebody bringing it up or talking about it or being a little bit.
David Wiener: L yeah, let's let's think about it. Let's talk about it. And then you gotta find out
DJ Van Keuren: Yeah.
David Wiener: about it too.
DJ Van Keuren: Well, you know, so we do the largest family office real estate investing study in the world actually. And, you know, when you look at some of the numbers that are tax related, if you had to guess how many families do not do 1031 exchanges, what would you say?
David Wiener: a vast majority, I would say. prob yeah, I was gonna say probably seventy five.
DJ Van Keuren: Yeah, it's 80%. It's been consistent every single year. Yeah. And then you look at another great tax strategy with real estate, and that's qualified investment strategies, right? And everybody thought that families would be the main investors in those. The issue
David Wiener: Yeah.
DJ Van Keuren: is... only about 34 % consistently of the families will invest into qualified opportunity zones. And initially it was because the rules weren't clear the first year, right? So they didn't know what's going on, but it still comes down to, I don't understand it. I don't know really how this works. And so that number has been consistently in about 30 to 35 % of the families have actually taken advantage of those. And so it's not
David Wiener: Wow.
DJ Van Keuren: a matter of, and we know they're smart. It's just, I'm not going to invest in anything. don't understand.
David Wiener: that's a good argument for the fact that every family office should have a tax strategist as part of it. You know, somebody who knows that area and can can bring up those ideas and and those kinds of things. I'll volunteer, you know.
DJ Van Keuren: Well, you're 100 % right. And I'll tell you, I can't tell you how many, I mean, I can tell you stories of, we have an executive education class in the Institute at University of for the first class we did years ago had three billionaire families represented, whether it was a family member or it was a CIO. And they all asked, what's a cap rate? Well, from a real estate perspective, that's pretty fundamental, right?
David Wiener: Yeah.
DJ Van Keuren: And so, It's just a matter of educating. So what you're doing, not only speaking, but here with your show, is a huge, huge benefit, right? It's just a matter of same thing, getting it out to as many people as possible so that they can understand. And that's exactly what anybody listening to this should do. They should be forwarding this information or bringing it up or say, you might want to check this out because, you know, it's a lot of money. that with different
David Wiener: It is a lot of money.
DJ Van Keuren: tax strategies, right?
David Wiener: And yet, you know, like I said, tax evasion's a crime and most of them would not even consider tax evasion. But tax
DJ Van Keuren: Mm-hmm.
David Wiener: avoidance, you gotta do it. You gotta do it. my dad told me as I was growing up, you know, I hope someday you have a very large tax bill. And I said,
DJ Van Keuren: Hmm.
David Wiener: gee, thanks, Dad. You know, and he said, No, no, don't pay a cent more than you absolutely have to, but I hope you wind up having to pay a large tax bill. And it it came true. He didn't live to see it, but it came true. But now I gotta figure out how to get to all of these family offices to tell them, you know, this is what you need to consider. Here's so the deduction sitting there, the process oftentimes doesn't get a look at it. Hold on to that because I want to put some size on what we're describing. Here's where we are. A first-time short-term rental owner with one property gets this done because they're listening to the podcasts. They're going to real estate meetups to learn and they're and they're learning about these things. A family with a portfolio you couldn't count on two hands often doesn't. Same code, same buildings, same advantage, same deduction available to both of them. The difference is really who heard about it? Two things. if this is Resonating with you, I'm going to invite you to subscribe to the Tax Strategy Playbook newsletter at Tax StrategyPlaybook.com slash newsletter. And it gives you free access to my 2026 tax planning guide and playbook notes or a cheat sheet for every episode we do at no charge. And then send me one word back. Yes or no? Has anybody ever run a cost segregation study on a property you own? If your answer is I don't know. Put that down as a no and get in contact with me and I can explain it all to you. Okay, so let's get out of theory. Tell me if you can about a specific one. No names, no family, kind of what the property was, what the basis was, and what happened when the tax question came up in the investment committee.
DJ Van Keuren: Well, again,
David Wiener: Do you have one that you that comes to mind?
DJ Van Keuren: actually, you need to, once again, in order for it to come up in the investment committee, you need to have somebody that brings it up and talks about it. It's really getting to that point, but to implement in an investment committee, that's not an issue. They're like, of course, right? Why would you not do it? unless there was some specific reason not to do it, which you can tell me if there is. I don't know why you wouldn't necessarily.
David Wiener: There's only a couple of reasons. I mean, if you plan on selling soon without doing a ten thirty one, then
DJ Van Keuren: Yes. Yes.
David Wiener: it's not worth doing. And the basis is you know, it used to be years and years ago that no cost segregation s company would look at a property under a million dollars depreciable basis. That's not true anymore. And that's one of the reasons the small first time investors are able to take advantage of cost segregation now, because I know we work with properties with a cost
DJ Van Keuren: you
David Wiener: basis of a hundred and fifty thousand and up. Well, that's pretty much all of your properties. I mean, unless you're just buying old beat up houses, you know. That kind of stuff. But so you know there's a lot of people out there that believe, well, my property's too small to do a cost segregation, or my property's too old to do a cost segregation. Unless you're planning on flipping the property and and not doing a 1031 exchange, there's very little reason not to do a cost segregation study. Now it may be that it's passive and you don't have enough passive income to offset. But that's an individual case, and it's still worth at least, you know, talking about it with somebody who knows cost segregation and can guide you there.
DJ Van Keuren: But even if that's the case, though, mean, those tax benefits are just going to continue to accumulate, right? You're not losing them, but you can use them later on down the road.
David Wiener: No, you can use them later on down the road, but in some cases, this we're talking smaller properties, it doesn't really make sense to accelerate a deduction that you can't use right away or within the first couple of years because you're speeding it up to slow it back down and but I go over all of that stuff with everybody that I talk to that want comes to me for a free estimate, so that if it's just definitely not going to be in their best interest, I'll tell them I I don't think this'll this'll help you, but go back to your tax professional and see and see what they say because they know your tax situation better than I do. So when you underwrite an acquisition, is is the tax treatment there in the model?
DJ Van Keuren: Yes, for us, it is. We'll go ahead and it's been great since it was passed under this new administration going back to 100%, right?
David Wiener: Absolutely.
DJ Van Keuren: that's something that we definitely take into consideration. And one of the things that I've had an issue with for a long time is that when you look at real estate models, Typically when they talk returns and everything, they're talking just, they're not including any of the tax benefits. And those tax benefits, whether it's deferral or something else, can add another 3 to 4 % return on what you're doing.
David Wiener: Absolutely. I just did a study last year for a flight school that got the guy an additional two million dollars worth of tax deductions in that first year. That'll move the needle right there.
DJ Van Keuren: I mean, it's one of our partners. His family had found the Fairmount hotels, and he owns quite a number of very large assets in New York City. And he has 100 million of passive offsets. he's like, people are like, well, why did you do this? Or why did you do that? And he's like, look, my 7 % is really like an 11 % return. He goes, I'm never going to run out of it. And that's
David Wiener: Absolutely.
DJ Van Keuren: why he went and got, you know, and went for a new portfolio and all this other stuff. you know, that's the other issue that a lot of people don't think about. You know, when you hold onto assets for a long time, especially if it's passed down to the next gen, well, the next gen is sort of picking up this asset and they don't know because they didn't build it. But I can't tell you how many families I've talked to that have like no basis and it's worth tens and tens and tens and tens of millions of dollars and they're getting no tax benefits out of it. And to me,
David Wiener: Yeah, that's wow.
DJ Van Keuren: that's crazy because one costs seg, like you said, and you can increase the portfolio and get additional deductions, but that's the other thing too. It's like, well, I don't have any debt on it and it's not doing anything bad, but reality is you're not maximizing.
David Wiener: Absolutely. That's true. That's absolutely true. You said that families want preservation over return. So where does a legal deduction fit in that? Is that is claiming depreciation a preservation move or a return move? And do you think the industry's thinking about it under the wrong one?
DJ Van Keuren: Well, the average return for a family office's portfolio, you're probably going to be surprised at this, but it's 7%. That's the average return. And so it's more about saving. So first is making sure that the money stays safe. Secondly would be the tax benefits from that. So that comes secondary to where that money is being put. And it's not necessarily, a decision isn't necessarily being made because of the tax benefits. But at some point in time, you you're gonna look for everything you can.
David Wiener: Yeah, so risk is probably the most important thing in their mind. not losing the money they have, you know. Return is great. they just don't know about it.
DJ Van Keuren: I mean, what's the chances that you're going to create that type of wealth ever again? Now, it does happen occasionally, but if you get $200 million, $400 million, $500 million, your chances of that happening again are very, very, very small. So you want to make sure you keep it on. Now, with that being said, And I don't know if we spoke about this before, but 70 % of families lose their wealth by the second gen and 90 % by the third generation, which
David Wiener: Wow.
DJ Van Keuren: is another reason to maximize the tax benefits.
David Wiener: Absolutely true. Absolutely. And there's another side to all of this, and and I'd rather put it on the table myself than have somebody raise it in the comments. I sort of pushed off a a question earlier. Well let me lay out the limits. I want your read on them, DJ. This isn't free money. When you sell, the accelerated piece comes back at you. Section twelve forty-five property, which is the stuff that we can accelerate, recaptures at ordinary rates. The twelve fifty side carries the twenty-five percent unrecaptured rate. That's episode seventeen. That's it's it's the answer for anybody wondering what happens on the way out. Unless you do a ten thirty-one exchange. If the plan is to hold the building and pass it down, the math changes. Episode 19 gets into which assets serve your heirs well and which ones cause problems. That's a good one to listen to. Back in episode 25, I said a study can't rescue
DJ Van Keuren: Cough
David Wiener: a bad deal. That still stands. A study, a cost segregation study, a 179D study, makes a good deal better. It doesn't fix a bad one. One more thing while we're here. None of this is a loophole. None of this is a gray area. I want to make sure people understand that. Tax evasion is a crime. I'm never going to lead you there. This is the other thing entirely. There these are recovery periods Congress wrote into the code on purpose for people who buy buildings. So get me the other side. Who's the family where a study genuinely isn't the right move and what makes it wrong for them, in your opinion?
DJ Van Keuren: Well, you brought it up before, if it's a short term, right?
David Wiener: Short term hold, yeah.
DJ Van Keuren: If it's going to be a short term hold, that's primarily the reason why it wouldn't be utilized. Other than that, You know, that's where I come back to you to say, what else is there? I mean, that's the biggest thing on the radar is the time period.
David Wiener: Yeah, I I would suggest that that's that's absolutely true and that's about the only one. you know, I think the accelerated depreciation is a great idea, but it sounds to me like the family office world just hasn't caught up on it yet. Would you say that's true?
DJ Van Keuren: Yeah, 100%. I mean, once again, you have to have somebody that brings it up at the table.
David Wiener: So now my job is to help family offices ge get up to speed. That's not a small task. So
DJ Van Keuren: Well, you know, but that's how the Institute came about. It started as a one-page website having to do with market cycles, and then it just continued to grow. And so people like you are extremely valuable because whether we have you write an article in the magazine, we have you on our podcast, maybe we have you at an event, that's one way that we're really able to get the word out there. And, you know, there was the biggest comment of gentlemen, he's become a good friend. He's a billionaire and he's just a great guy. And he came to one of the events and he literally said, he said this on camera, is that I didn't know what I didn't know. And
David Wiener: That's it. That's that's the phrase right there. You don't know what you don't know. I was
DJ Van Keuren: Yeah.
David Wiener: surprised. I spoke at a at an event called WealthCon a number of years ago, and I was speaking in a room of three hundred and fifty people. Seasoned investors, mostly residential, but seasoned investors. And I start I started out by saying, How many of you guys are familiar with cost segregation? I figured every every hand in the room would go up. Less than two dozen out of three hundred and fifty people. And I said, How many of you guys have ever done cost segregation? Six. They were all my clients. And one guy in the back of the room stood up and said, We've done twenty seven properties together. I haven't paid taxes in years and I don't plan on paying any going forward And that caught everybody's attention. Now they all know about cost segregation. Okay. what I want to do is I wanna I wanna give up some rapid fire questions. and then I'm gonna give everybody something to do. If you can answer me in one sentence or less, that would be good. Ready? One word. When a family misses this deduction, is that a decision or an oversight?
DJ Van Keuren: oversight.
David Wiener: Who's more likely to raise a new tax strategy with a family, the family or the advisor?
DJ Van Keuren: Probably the advisor.
David Wiener: Okay. Bigger portfolio, better tax planning. True or false? Best way for a family to find out what they don't know they're missing.
DJ Van Keuren: Listen to your show.
David Wiener: I could have written that for you. That's that's pretty good. I'll send you I'll send you a couple bucks for that one. you've sat in on a lot of investment committee meetings, I assume. What's the best question you've ever heard somebody ask in one?
DJ Van Keuren: Why am I just learning about this now?
David Wiener: Boy, if I've heard that a lot.
DJ Van Keuren: Hahaha
David Wiener: So at the end of every episode, we like to give people a playbook. We call it the tax strategy playbook, after all. And by the way, you mentioned I would be more than happy to write an article, be on a podcast, or speak in person anytime if I get an opportunity to educate people about cost segregation. We haven't even talked about 179D, which We love the big beautiful bill because it restored 100% bonus depreciation. That was the yay, but the boo was 179D ended for any buildings that were started, that were begun after June 30th, 2026. we haven't even talked about that, and I'll bet that's something that does not come up with your commercial buildings as well, and absolutely needs to. So here's your playbook. Number one, ask your tax professional one question this week. Has anyone ever run a cost segregation study on the property I own? Not should we. Has anyone ever? DJ, you've you've watched these conversations start. When somebody says, why haven't I learned this before? One, what are they really asking? And two, what happens at that point?
DJ Van Keuren: Well, think what they're asking, I can tell you what they're thinking. They're
David Wiener: Yeah.
DJ Van Keuren: thinking, what else am I missing that hasn't been brought up or discussed? And what were the other two? You said, what are they?
David Wiener: And and and w what happens when somebody finally asks that question?
DJ Van Keuren: It's like, okay, we need to figure this out now. We've already wasted too much time and probably a bunch of money, so let's figure out where we can use it, when it's beneficial, when it's not beneficial, and let's implement.
David Wiener: Do do you think there's a bit of accusation there where they're accusing their their advisors of not bringing them the the stuff that they need?
DJ Van Keuren: I don't think that, I mean, remember what I said too, is that if they have somebody helping them, it's usually somebody that falls into it because they trust them, right?
David Wiener: Mm. Right.
DJ Van Keuren: And so I think a lot of times it's like, it's accepted that they may not have been brought everything because this person, you know,
David Wiener: Doesn't know everything.
DJ Van Keuren: they don't because they haven't been doing this for a long time. I also think that there's a lot of advisors. that really they just stopped learning or they stopped digging or they stopped, you know, saying, how can I be the very best that's out there? And they just get complacent.
David Wiener: You can't stop learning. You've got to be a perpetual student because things change all the time. Okay, good. So number two on your playbook, before you call anybody, pull three things on every property that you've held more than a year. The purchase date, the date it was placed in service, which was the date it was ready for a tenant or for the business to use, and the purchase price. Those two dates are often different and both of them matter. That's all you really need to start. And if you're sitting there thinking you missed your chance because you bought it years ago and you didn't. Episode 27, which we just did a few weeks ago, covers the lookback study Form 3115, how the catch up lands on a current return. It came out a couple of weeks ago. It was built for exactly that. Number three, if you own a building through an entity with other people, find the operating agreements this week and read the tax allocation section. when somebody proposes a study to you, ask whether the cost segregation company performs an in-person site visit. If the answer is anything other than yes, treat it as a no and go find somebody else. Five, if you want to know whether your property is even a candidate, I'll be happy to look at it at no cost. Book it at Callendly.com slash David Dash Wiener slash CS or call me at 770-224-8504. Select option two. No obligation, no pitch. If a study won't pay for itself on your property, I'll tell you that because I'd rather be the person you call the next time. Write it down. One ask and we're done. Think of one person you know who absolutely, yep.
DJ Van Keuren: I want to say one thing too that you needed to add to that is if you've invested into a direct transaction, so it's an SPV, it's a private placement, look to see if there is a cost seg that the operator's doing that you're investing
David Wiener: absolutely.
DJ Van Keuren: with and are you benefiting from that? Because it doesn't happen all the time.
David Wiener: That's a question that they need to ask the operator. Yeah.
DJ Van Keuren: Yeah, exactly. And that happens a lot less than you think it does. Or a lot more.
David Wiener: No, I'm I'm pretty sure I know how little how f f frequently it happens and it's not very.
DJ Van Keuren: Yeah.
David Wiener: Very good. So one ask and we're done. Think of one person you know who owns buildings. Somebody who's been at it a while with good people around them. Send them this episode. The odds are decent that nobody's ever brought this up with them, and one conversation changes that. Not a list, not a group chat. Think of one person and send this episode to DJ, where can people find you and what are you working on right now?
DJ Van Keuren: So they can find me a couple of different places. One is djvankeuren.com. They can Google me and you'll see that I'll come up. And the two entities I'm affiliated with is the Family Office Real Estate Institute, where it's djvk at fore.institute, not .com, and then dj at Evergreen Property Partners. The biggest thing that I'm working on right now is we actually, it's been done over the last number of years, but has created a, we've created a real estate platform that is really focused on tax efficiency and compounding. So we figured out how we can allocate like an institution and have a perpetual 1031 exchange happening. within a diversified portfolio of value-add opportunistic development deals. So that is something that you're not going to find out in the marketplace. And so that's something we're really excited about.
David Wiener: Fantastic. And we will put all of DJ's contact information in the show notes at TaxstrategyPlaybook.com. So if you're looking for him, you can find him right there. thanks for coming on, DJ. I I think this is a question that's been sitting out there since twenty twenty-two and something
DJ Van Keuren: you
David Wiener: we absolutely needed to cover. next week on
DJ Van Keuren: Well, thanks for having me.
David Wiener: My pleasure. Next week, Join us on the tax strategy playbook for more strategies that you can use. Remember that tax evasion is a crime, tax avoidance is mandatory. I'm David Wiener, Mr. Cashflow, and I'll see you next Tuesday on the Tax Strategy Playbook.
Principal
DJ is a Co-Managing Member of Evergreen Property Partners, a real estate investment manager built for family offices and multi-generational investors. Evergreen sponsors the Evergreen Legacy Fund, the firm's third fund and the first built on its Master Tenancy Structure—a patent-pending platform designed to let real estate capital compound continuously across 1031 exchanges rather than reset at each sale. The fund invests alongside an operator bench of six joint-venture partners with $30B+ in combined transaction volume.
Before Evergreen, DJ spent 28 years inside and alongside family offices as an allocator, capital markets executive, and fund founder:
President of Real Estate, fourth-generation family office (MLB team ownership)
Vice President, Hayman Family Office (Giorgio Beverly Hills / Giorgio Perfume / Discus Dental)
Director, Arsenault Family Office (Mountain High Yogurt)
Vice President, Jain Family Office — underwrote and structured equity and debt on projects of $75M–$400M
Founder and Managing Director, The American Dream Fund (single-family residential)
EVP Capital Markets — secured $250M in commitments from international private equity
Real estate investment banker — structured equity and debt on $5M–$250M transactions
$5B+ in real estate assets underwritten across the career
DJ also founded the Family Office Real Estate Institute, the industry's dedicated education and research platform for family office real estate, and publish FORE Magazine. I am the author of Real Estate Investing for Family Offices, … Read More
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