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Host (possibly Jeff or a similar podcast host)
So you worked inside one of the two AQR co founders David Caballer's family office. You saw an opportunity to invest in real estate in a tax aware strategy. What was your thesis behind starting what
David Kotler
you do today, starting with Arkitel. We are a private investment firm specifically focused on maximizing after tax returns for a taxable client base. You know I began my career at AQR and as you mentioned, you know I, I was, I saw how AQR was developing what has now become their tax aware public market strategies. And as you're probably well aware, they've grown significantly over the past several years with this strategy. You know, as, as they were growing and incubating those strategies in house, there was an opportunity because AQR doesn't do anything within private markets to try and bring the same tax focused lens into private assets.
Host (possibly Jeff or a similar podcast host)
Tell me about the opportunity for tax aware investing in real estate.
David Kotler
You know, real estate is gifted one of the most advantaged tax codes of any investable asset class in the United States. And I think what will be pretty eye opening is, you know, everybody knows or has an intuition that real estate can be tax efficient. But I don't think most people understand just how much they're leaving on the table unless they approach it in a very intentional manner.
Host (possibly Jeff or a similar podcast host)
Break that down to brass tax. What kind of tax savings are we talking about and does this really move
David Kotler
the needle approaching private real estate investing in a tax focused manner can result in a two times greater after tax net of fee return or basically true wealth creation compared to a tax agnostic strategy. Look at incentives of the managers that are actually managing these underlying private real estate investors investments. They're incentivized to cycle through investments. That's typically how they take payment of their own performance fee. They can crystallize their promote. Well when you do that you crystallize the tax consequences, the depreciation recapture, some of the capital gains implications of private real estate. So I think again you're leaving a lot on the table if you don't approach private real estate investing in a manner where there's alignment of investment strategy with structure.
Host (possibly Jeff or a similar podcast host)
Some listeners might question why I talk a lot about tax and tax alpha and I just look at the markets very much as mostly efficient markets. In the public markets I believe in the mostly efficient market hypothesis and the private markets it's more efficient than a lot of people think. And tax is one of those parts of the market where you can actually sustain alpha. Especially when you're talking about, you mentioned double the post Net returns on essentially what I would guess is a similar investment. So you have the same kind of high level investment in the same property. One is tax tax advantageous, one is not. You might get twice twice as higher return than a tax advantaged one.
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David Kotler
I mean it's this concept of structural alpha. So again, if you combine an underlying investment strategy and marry it with the right structure, you can get more than a two times after tax total return. It's greater than if you approach it in a tax agnostic manner. And I think this is, it's really critical because when you approach, when you approach investing as a taxable investor, it needs to fundamentally shift how you evaluate the investment options that are available to you because you're no longer looking at items from a pre tax basis. So some strategies that can make a lot of sense from a pre tax returns basis no longer make sense once you layer in the after tax return considerations. If you look at a traditional endowment model, they have high single digit exposure historically to private real estate. They don't get any of the tax advantages that are afforded to it. So when you layer in the after tax return profile, some of the diversification Benefits and the correlation to other major investment asset classes. I would argue that taxable investors on average can tend to be under allocated to private real estate.
Host (possibly Jeff or a similar podcast host)
So maybe this is a good time to double click on what it means practically to invest in tax aware real estate strategy. So I'm a high net worth investor that's investing $1 million into strategy.
Sponsor/Announcer
What do I get?
David Kotler
You should be able to get via K1s pass through depreciation. And by the way, the current administration, recent legislation has been implemented that makes it very, very, let's say, compelling to invest into real assets because you're able to accelerate a lot of depreciation and take bonus allocations upfront. You look at private real estate, whether it's the non traded REITs or traditional closed end funds they have, they have a set life cycle, maybe they underwrite to three, five or seven year target durations. Maybe cycling through properties, that is how you trigger a lot of the tax consequences that are associated with with private real estate.
Host (possibly Jeff or a similar podcast host)
And that's because other firms are not focused on an after tax basis. So it might make sense for them to sell, to generate DPI and to show a multiple to investors. You guys are focused on a very different part of the market where you're focused on the taxable investors and what they care about is after tax.
David Kotler
There are a couple of factors that drive kind of the cycling mentality that's been traditional throughout private real estate. The first is if you're serving a taxable and tax exempt client base, you know your mandate to maximize after tax returns falls because you're also trying to cater to maximizing pre tax returns, which by the way is how most managers operate. So that should fundamentally shift whether or not it makes sense to sell an asset in a particular moment in time. Again, if you're not, you don't have to underwrite what the tax consequences are. That's the first answer. The second answer is if you think about traditionally how most managers get paid, it's through promote, it's through carry. And typically carry is crystallized and payable once the properties or underlying investments are sold. That's the liquidity event. And then I think, you know, the third thing is look, it's people get addicted to liquidity.
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David Kotler
By specifically focusing on a taxable client base, we remove that mandate of trying to serve both pre tax and after tax returns clients so we can specifically focus on how do we maximize after tax returns.
Host (possibly Jeff or a similar podcast host)
I'm going to go back to where we started, which you said that real estate investors, taxable investors, can double their after tax return gain versus a comparable investment. Walk me through that.
David Kotler
So let's, let's take an investment that is underwritten in a tax agnostic manner to a five year time horizon. Again, that may be consistent with what you see in a lot of private real estate funds, some direct investments. Think about what happens. So you make an investment, hopefully there's yield that's getting thrown off. Depending on what that investment is, you do generate some depreciation so that yield can be tax shielded as it's coming out to you and then the asset is sold. And for the purpose of this illustration, a 1031 exchange is not utilized. So you actually have a taxable event at that moment in time. Well, through a combination of some depreciation recapture. So and depreciation recapture can be broken out into several different buckets. Some is taxed at actually ordinary income tax rates. Some is taxed at a more advantaged, you know, cap 25% federal rate. But between the depreciation recapture and the long term capital gains, and I'm being generous here, assuming that the investment was hold, held for several years. So you're not falling into a short term capital gain scenario. You're paying, you're paying tax drag at that point. And that blended rate can be, you know, depending on your state of residency. If you're a New York City resident, as you are, you know, that effective tax rate can be, you know, well north of 35% combined state, federal and potentially city. Compare that to a strategy where you remain invested so you continue to get yield off of the underlying investment. Maybe there's some refinancing scenarios that allow you to very tax efficiently, continue to get your capital out from the underlying investment and you stay invested and continue to compound. Well, in addition to deferring the depreciation recapture and the capital gains event, the long term capital gains event that I just referenced, what you're also able to do is if you've generated depreciation from that investment and you've banked these passive activity losses, this tax asset on your books, you can actually free up and utilize that tax asset if you pair it with other passive income generators. And then what you can do is you can Actually again, increase the after tax return across that second investment, whereby it significantly increases the value of the first investment you made.
Host (possibly Jeff or a similar podcast host)
And do you also look for 1031 exchanges within your strategy or do you just rely on holding for a long time?
David Kotler
So the 1031 exchange is a gift from the IRS. It's an incredible tool to be able to rebalance or trade out of an asset and continue to defer the tax liability. So to continue to defer depreciation recapture, continue to defer the capital gains of that at that moment. Our strategy, specifically, we're not reliant on the 1031 exchange. We're actually underwriting to 15 year hold periods. You know, at that moment, once some of the tax benefits do start to diminish as you think about working your way through a depreciation schedule, we have the ability to utilize a 1031 exchange to tax efficiently rebalance our portfolio. But the strategy itself is not predicated on the use of it. And I, I think that's one thing. Look, I want to highlight this again. It's a gift. It would be wrong of me to try and say it's not a gift from the irs, but we find it's too, it's overused, it's too prevalent. And if it's used incorrectly, by the way, so you have managers that are cycling out of assets and are justifying their tax efficiency through the use of the 1031 exchange, I would still then ask, okay, how much are you paying away to frictional costs, even separate from taxes? You know, there's a lot of data that suggests that if you're a 1031 buyer, because of the time pressures that are implemented on you, you tend to overpay for the replacement property. Not to mention, by the way, some of the fees that a lot of 1031 exchange facilitators will charge to the underlying client to execute a 1031 exchange.
Host (possibly Jeff or a similar podcast host)
You obviously built this with a billion dollar family office in mind. David Kotler, Other family offices, when they come to you, what problems are they looking to solve?
David Kotler
There's two different kinds. So you have a family office that's upscale and has the in house, you know, capabilities to go and implement direct, real asset or private investing themselves. So I would say off the bat, if you're upscale to bring a team in house, you go in and you can build a diversified portfolio where you're the only investor, you control buy and sell decisions yourself. That's the optimal way to invest. Right? And you can actually layer in tax considerations from other parts of your portfolio to inform when it may make sense to actually trigger sales of those, those, those underlying investments. What we have found is that a significant percentage of family offices, whether it's because they're not of scale to actually bring that team in house, or candidly, some that just don't want to take on the operational complexity of executing deals directly and then managing those investments, you know, an outsourced solution can be very compelling. And by the way, that's really what arcatelle was founded for. It's how do we become an outsourced solution for, you know, ultra high net worth taxable investors?
Host (possibly Jeff or a similar podcast host)
Do you find that you have to sell the post the net of tax strategy with every new client?
David Kotler
The answer is yes. And I mean, I'll even take a step back as we were launching Arcitel several years ago, you know, looking at how competed, you know, the private real estate industry is, you know, most in most investable asset classes you've been talked about, you know, Alpha gets eroded. Everybody's going to say they have smart investment teams and they're, they're smart and thoughtful with underwriting and risk management. You know, given how competed and commoditized the space was, you know, our North Star to really differentiate in a CSA in this was how are we more thoughtful about tax efficiency? How do we specifically focus on serving a taxable client base to the best of our abilities in a commingled structure? So you know, for us that has allowed us to get into business and to keep growing our business in this really commoditized and competed space. I think we're still in very early innings of the tax story here. I mean, you look at the incredible traction some firms like AQR have gotten as they've grown their tax aware investing business. You know, I think if you're a taxable investor, the metric that matters is what your after tax return is. And I think that is going to continue to proliferate across the investment industry. And if you're an RAA or you're a family office or a multifamily office, you know, how do you differentiate and provide value to your clients? How do you provide, you know, alpha that won't get eroded? Structural alpha, it's really through. How do you, how do you, how are you smarter about tax, how are you more thoughtful about the structure and strategies that you're marrying?
Host (possibly Jeff or a similar podcast host)
You have a unique vantage point where you are helping the co founder of AQR who built the largest really franchise in tax aware investing. You now deal with tax Aware investors all the time. What do you attribute to the rise of tax awareness and this entire trend?
David Kotler
It comes back to how competed and commoditized the investment space can be and all the products and look about the sales forces that are distributing here. It's, you know, you, you, you can try and differentiate, but all sources of alpha, as you mentioned, you have typically, I shouldn't say all but alpha can erode over time. If you think about structural alpha and trying to be smarter about maximizing some tax benefits which are afforded by the tax code, which can change. But you're, you're operating based on what the current IRS guidelines and the rules are today. That's a way where by the way, the magnitude can be so significant that it becomes a much more compelling story to tell. I mean you can talk about again finding a manager that has, you know, top quartile, top decile, pre tax returns absolutely matters. I'm not trying to diminish that. But let's look at what the dispersion of the returns might be. The guess here or the statement would be that will dwarf the return dispersion compared to, you know, lower quartile to top quartile. When you layer in the after tax, the after tax component, ideally you marry both. You marry top quartile, top decile, pre tax performance with the tax efficiency.
Host (possibly Jeff or a similar podcast host)
If you look at median versus top quartile and core core plus real estate, so the bread and butter typically about 200 basis points, there's of course a whole question on whether that's sustained, whether top quartile is sustained. There's also a question on whether you could pick those managers, whether there's some luck involved there. But even so, it's only 200 days basis point which is why I think this whole tax aware strategy has become so big in the public markets because you have a similar phenomenon there. The spread is even lower between top, top quartile and median. And when you see this tax structural alpha tech strategy, I think it's going to be a thing to come for many years.
David Kotler
You look at what variables you can control, right? You can diligence managers, you can diligence underlying investments. They can be very shrewd investors and risk managers. But you know, a lot can happen that's outside of your control. I think tax is more within your control certainly I would say than the, the, the pre tax return outcome of an underlying investment. So you know, you focus on those variables that you can at least better control.
Host (possibly Jeff or a similar podcast host)
Well, I think tax aware investing is here to stay. I think we're going to see a lot of really interesting applications across different asset classes, so really appreciate you jumping on the podcast. Looking forward to continuing this conversation live. Thank you very much, David.
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Host (possibly Jeff or a similar podcast host)
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Episode Title: E317: Most Real Estate Investors Optimize the Wrong Return Metric
Date: March 4, 2026
Host: David Weisburd (possibly with guest host, referred to as Jeff in transcript)
Guest: David Kotler (Founder of Arkitel, former AQR)
This episode tackles the critical mistake that most real estate investors make: optimizing for pre-tax returns rather than after-tax (net) returns. David Kotler, founder of Arkitel and an expert in tax-aware real estate investing, shares lessons from his background at AQR and managing a family office. He breaks down why structural alpha via tax strategy can have a transformative effect on real estate wealth creation, especially for taxable investors.
“You know, real estate is gifted one of the most advantaged tax codes of any investable asset class in the United States... I don't think most people understand just how much they're leaving on the table unless they approach it in a very intentional manner.”
— David Kotler [00:54]
“Approaching private real estate investing in a tax focused manner can result in a two times greater after tax net of fee return... compared to a tax agnostic strategy.”
— David Kotler [01:18]
“If you're serving a taxable and tax exempt client base, your mandate to maximize after tax returns falls because you're also trying to cater to maximizing pre tax returns, which by the way is how most managers operate.”
— David Kotler [06:12]
“Our strategy, specifically, we're not reliant on the 1031 exchange. We're actually underwriting to 15 year hold periods... If it's used incorrectly... you tend to overpay for the replacement property.”
— David Kotler [12:04]
“A significant percentage of family offices, whether it's because they're not of scale... or... don't want to take on the operational complexity... an outsourced solution can be very compelling. And by the way, that's really what arcatelle was founded for.”
— David Kotler [13:29]
“For us that has allowed us to get into business and to keep growing our business in this really commoditized and competed space. I think we're still in very early innings of the tax story here.”
— David Kotler [14:29]
“I think tax is more within your control, certainly I would say than the pre-tax return outcome of an underlying investment. So you know, you focus on those variables that you can at least better control.”
— David Kotler [17:36]
On eye-opening tax advantages:
“Real estate is gifted one of the most advantaged tax codes... I don't think most people understand just how much they're leaving on the table unless they approach it in a very intentional manner.” — David Kotler [00:54]
Structural alpha explained:
“It's this concept of structural alpha. If you combine an underlying investment strategy and marry it with the right structure, you can get more than a two times after tax total return.” — David Kotler [04:12]
Why 1031 exchanges aren’t a cure-all:
“It's a gift. It would be wrong of me to try and say it's not a gift from the IRS, but we find it's overused, it's too prevalent. If it's used incorrectly... you tend to overpay for the replacement property.” — David Kotler [12:04]
On commoditization and the rise of tax-smart investing:
“You can talk about again finding a manager that has top quartile, top decile, pre tax returns... but when you layer in the after tax, the after tax component, ideally you marry both.” — David Kotler [16:03]
Kotler’s tone is analytical, pragmatic, and focused on clear financial outcomes. The host presses for real-world examples and practical applications, resulting in a conversation rich in actionable insights and strategic perspective.
The episode powerfully underscores the overlooked importance of after-tax returns in real estate investing. By marrying investment strategy to tax structure, investors—particularly family offices and high-net-worth individuals—can potentially double their wealth creation compared to traditional, tax-agnostic approaches. As alpha is squeezed in a competitive market, tax strategy emerges as a major lever for differentiation and sustainable outperformance.