Charitable Remainder Trusts: Tax Wins Every Wealthy Donor Needs

Do you have over $1 million in appreciated assets and a passion for giving back? There may be a smarter way to donate — one that generates income, slashes your tax bill, and supports causes you love. In this episode, we break down Charitable Remainder Trusts and why they're one of the most powerful yet underutilized tools in wealth management today. Whether you're holding concentrated stock, investment real estate, or a business interest, a CRT could help you avoid capital gains taxes while creating a reliable income stream for retirement. Our fee-based, fiduciary advisors walk you through exactly how these trusts work, who they're designed for, and what to consider before setting one up as part of your broader financial planning strategy. Don't leave a significant tax opportunity on the table. Ready to talk? Schedule a complimentary discovery call at TDWealth.net. For educational purposes only. Not investment advice. 📖 Full show notes: https://tdwealth.net/charitable-remainder-trusts-tax-wins-every-wealthy-donor-needs/

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Transcript

SPEAKER_01 0:00

So imagine you're sitting on um over a million dollars in highly appreciated assets. Right. You know, maybe it's a business you built from the ground up over twenty years, or uh a portfolio of investment real estate that you've just managed since the nineties.

SPEAKER_00 0:14

Yeah. Or even if you're a tech executive with just a massive concentration of company stock.

SPEAKER_01 0:20

Exactly. And you know you need to diversify. I mean, it's investing 101, right? But the moment you go to sell that asset to diversify, you are going to trigger this massive wealth-destroying capital gains tax bill.

SPEAKER_00 0:32

It's brutal.

SPEAKER_01 0:32

So how do you solve that?

SPEAKER_00 0:34

Welcome to today's deep dive, specifically curated for the 1715 Treasure Coast Financial Wellness Podcast by Davies Wealth Management.

SPEAKER_01 0:42

Yeah, they're a fee-based fiduciary advisory firm out of Stewart, Florida.

SPEAKER_00 0:46

Right. And today we have a very specific mission for you. We are unpacking this incredibly powerful yet surprisingly underutilized strategy for high net worth individuals, which is uh charitable remainder trusts. It really is, you know, the classic catch-22 of wealth accumulation. Because you're penalized heavily for doing the responsible thing, which is diversifying your risk.

SPEAKER_01 1:09

Right. You get punished for doing it right.

SPEAKER_00 1:11

Exactly. And for a lot of people, the sheer terror of that tax bill causes them to just freeze up. They hold on to these concentrated, really risky positions way longer than they should, just hoping the market doesn't turn against them.

SPEAKER_01 1:24

Okay, let's unpack this because if the phrase charitable remainder trust or CRT hasn't come up in your state planning conversations yet, you might literally be leaving, I mean, hundreds of thousands of dollars on the table.

SPEAKER_00 1:36

Oh, absolutely.

SPEAKER_01 1:37

But before we get into the massive tax advantages of this structure, we need to understand the basic plumbing here. Like how does the asset actually move? Because a trust is essentially just a legal bucket, right?

SPEAKER_00 1:49

Yeah, that's a really good way to look at it.

SPEAKER_01 1:50

Yeah.

SPEAKER_00 1:50

A charitable remainder trust is a specific type of irrevocable trust. And whenever you set one up, there are three main parties involved in the transaction. First, there's the grantor. That's you, you know, the person who funds the trust with the appreciated asset and then receives an income stream from it.

SPEAKER_01 2:08

Aaron Powell Makes sense.

SPEAKER_00 2:09

Second, there's the trustee. That is the person or the institution actually managing the assets inside that bucket.

SPEAKER_01 2:16

Aaron Powell And could that be me? Like could I be my own trustee?

SPEAKER_00 2:18

Aaron Powell You can, yeah. You can be your own trustee initially, though a lot of people transition to a corporate trustee later on as things get more complex.

SPEAKER_01 2:25

Aaron Powell Got it. And the third party.

SPEAKER_00 2:27

Aaron Powell The third party is the charitable remainder beneficiary. And this uh this has to be a qualified nonprofit organization.

SPEAKER_01 2:35

Aaron Powell So how does this actually prevent the tax hit? Like if you have highly appreciated stock and you want to turn it into a diversified portfolio, what is the exact chronological process there?

SPEAKER_00 2:45

Aaron Powell Well the process starts with the transfer. You legally transfer your highly appreciated stock or real estate into the CRT.

SPEAKER_01 2:52

Wait, you don't sell it first.

SPEAKER_00 2:53

No, you do not sell it first. That is the critical mistake people make. You have to transfer the asset in kind.

SPEAKER_01 2:59

Oh wow. Okay.

SPEAKER_00 3:00

Because this specific trust is a tax-exempt entity under IRS rules. So the trust itself then sells the asset.

SPEAKER_01 3:08

Aaron Powell And since the trust doesn't pay capital gains taxes.

SPEAKER_00 3:12

Exactly. Zero taxes are paid at the moment of that sale. The trust then takes the full gross amount of cash, reinvests it, and pays you an income stream for the rest of your life, or you know, for a set period up to 20 years.

SPEAKER_01 3:25

Aaron Powell And then what happens at the end?

SPEAKER_00 3:26

Aaron Ross Powell When you pass away, or when that term ends, whatever's left in the trust goes to the charity.

SPEAKER_01 3:32

Aaron Powell Okay. So think of it like donating an apple orchard. You give the orchard to a trust, the trust sells the apples and gives you a steady cut of those profits for the rest of your life. I like that. It's a nice predictable income. Then when you pass away, the charity doesn't just get a few leftover apples, they get the actual land and whatever trees are remaining.

SPEAKER_00 3:52

Aaron Powell That is a brilliant way to visualize it. But there is a crucial guardrail here regarding the orchard, what we call the golden IRS rule for CRTs. The IRS mandates that the projected remainder going to the charity absolutely must be at least 10% of the initial net fair market value of whatever you put into the trust.

SPEAKER_01 4:11

Aaron Powell Oh, so you can't just structure it so the charity is left with like a single rotting apple tree at the end of 30 years.

SPEAKER_00 4:18

Precisely. That is not a suggestion or, you know, a loose guideline. It is a firm mathematical requirement.

SPEAKER_01 4:25

How do they even calculate that?

SPEAKER_00 4:26

The IRS uses their own actuarial tables, factoring in your life expectancy. If the math shows the charity isn't projected to get at least 10%, the trust is just invalid from day one.

SPEAKER_01 4:37

That makes perfect sense. I mean, they want to ensure there is genuine philanthropic intent, not just a tax dodge.

SPEAKER_00 4:44

Right.

SPEAKER_01 4:44

Now you mentioned a cut of the profits earlier, that income stream you get while you're alive. How exactly is that payout calculated?

SPEAKER_00 4:51

Well, how that income is calculated dictates the specific type of trust you set up. There are two main engines here.

SPEAKER_01 4:56

Okay, what's the first one?

SPEAKER_00 4:57

The first is the charitable remainder annuity trust, commonly called a C Crat. A CRAT pays you a fixed dollar amount every single year. By law, it has to be a minimum of 5% of the initial value you contributed.

SPEAKER_01 5:11

So if you put in a million dollars and set a 5% payout, you get exactly $50,000 a year.

SPEAKER_00 5:18

Every single year. It never changes, even if the trust investments double in value or get cut in half.

SPEAKER_01 5:24

Wait, if it pays a fixed dollar amount and never adjusts for inflation, isn't that inherently risky if you live another 20 or 30 years? I mean, 50 grand today does not buy what 50 grand buys in two decades. That seems like a massive flaw.

SPEAKER_00 5:37

You've hit on the exact reason why corrects are becoming much, much less common in practice. They offer extreme predictability, which you know some highly conservative investors really love.

SPEAKER_01 5:46

Sure, I can see that.

SPEAKER_00 5:47

But they completely lack inflation protection. Plus, the IRS won't let you add more assets to a C CRAT after it's initially funded. You want to contribute more next year? You have to set up an entirely new trust.

SPEAKER_01 5:58

Oh, that sounds like a headache. So what's the alternative?

SPEAKER_00 6:01

This brings us to the second, much more popular option: the charitable remainder unit trust, or CRUT.

SPEAKER_01 6:08

Let me guess. The CRUT recalculates based on the market.

SPEAKER_00 6:12

You got it. A CRUT pays a fixed percentage of the trust's value, but that value is recalculated every single year. The payout still has to be between 5% and 50%.

SPEAKER_01 6:23

So if the trust investments grow over time, your income stream grows with it.

SPEAKER_00 6:27

Exactly. It acts as a natural inflation hedge. Furthermore, a CRUT allows you to make ongoing additional contributions over time.

SPEAKER_01 6:35

Which is huge if you are an executive getting annual stock compensation or um a business owner selling off tranches of equity year after year. You can just keep feeding the same machine.

SPEAKER_00 6:44

That's it, exactly. And if we connect this to the bigger picture of retirement planning, there are even subtypes of the CRU. The most famous is the NIN MCRU.

SPEAKER_01 6:51

The NIN MCRU. Okay, that sounds like intense financial jargon. Unpack that for us.

SPEAKER_00 6:55

Yeah, it stands for net income with makeup C RUT. Basically, a NIN MCU root allows the trustee to intentionally limit your payout to the actual income the trust generates, like dividends or interest.

SPEAKER_01 7:06

Rather than a strict percentage of the total value.

SPEAKER_00 7:08

Right. And why would you want that?

SPEAKER_01 7:09

Yeah.

SPEAKER_00 7:10

Well, because if you are 50 years old and still working, you don't want more taxable income right now.

SPEAKER_01 7:16

Right. You're already in a high bracket.

SPEAKER_00 7:18

Exactly. The NIMCRUT allows you to aggressively grow the underlying assets inside the trust and intentionally defer taking the bulk of the income until you actually retire and drop into a lower tax bracket. It's just incredibly flexible.

SPEAKER_01 7:32

Okay, so the machinery is clear. The bucket is built. Now let's look at the financial output. Why do affluent donors actually go through the trouble of setting up this legal machinery? Let's dive into the core tax advantages.

SPEAKER_00 7:45

Aaron Powell Let's start with the most obvious one deferred capital gains. This is really the flagship benefit.

SPEAKER_01 7:50

Let's use a specific example.

SPEAKER_00 7:52

Let's look at an example modeled by Davies Wealth Management. Imagine you hold $2 million in concentrated company stock. Your cost basis, which you originally paid for years ago, is only $200,000.

SPEAKER_01 8:04

So you are sitting on $1.8 million in pure unrealized profit.

SPEAKER_00 8:09

Correct. If you just sell that stock directly through your brokerage account to diversify, you're getting hit with the top long-term capital gains rate of 20% plus the 3.8% net investment income tax. The NIAT. Yeah. That triggers roughly $342,000 in federal tax right out of the gate. And that is not even counting state taxes.

SPEAKER_01 8:30

Wow. So your $2 million instantly shrinks down to roughly $1.65 million to reinvest.

SPEAKER_00 8:35

Exactly. But if you use a CRT, that $342,000 stays invested inside the trust.

SPEAKER_01 8:42

Okay, here's where it gets really interesting. Because by avoiding that $342,000 tax hit on day one, you're essentially getting a zero interest six-figure loan from the government.

SPEAKER_00 8:53

That's one way to look at it, yeah.

SPEAKER_01 8:54

And you get to invest that loan for your own benefit inside the trust. The math on that compounding over 10, 20, or 30 years is just staggering.

SPEAKER_00 9:03

It is the time value of money working at maximum efficiency. Yeah. You are earning yields on money that normally would have just been sitting in the U.S. Treasury.

SPEAKER_01 9:10

That's incredible.

SPEAKER_00 9:11

And beyond just deferring the sale tax, there is an immediate income tax deduction. The year you fund the CRT, you get a tax deduction against your ordinary income.

SPEAKER_01 9:22

But wait, you don't get to deduct the whole $2 million, right? Because you are retaining an income stream from it.

SPEAKER_00 9:27

Exactly. You only get to deduct the present value of the remainder interest that the charity will eventually get.

SPEAKER_01 9:32

Okay, but how does the IRS value a gift that a charity might not receive for another 30 years?

SPEAKER_00 9:38

They use a mechanism known as Section 7520 rates. It sounds complicated, but conceptually, the IRS looks at current interest rates and your life expectancy to determine what that future gift is worth in today's dollars.

SPEAKER_01 9:53

So if interest rates are high.

SPEAKER_00 9:54

If interest rates are high, the assumed growth of the trust is higher, which generally increases the value of the deduction. For high income earners, this partial deduction translates to tens of thousands of dollars in immediate hard cash tag savings.

SPEAKER_01 10:08

And is there a limit on how much you can deduct?

SPEAKER_00 10:10

You can deduct up to 30% of your adjusted gross income in the year you set it up.

SPEAKER_01 10:14

And if the deduction is so massive that it wipes out that 30% limit in year one, like what happens to the rest?

SPEAKER_00 10:21

You don't lose it. The IRS allows you to carry forward whatever is left over for up to five additional years. It is a persistent shield against your income taxes.

SPEAKER_01 10:31

That is a huge benefit. So we've solved the immediate capital gains hit on the sale, and we've generated a nice income tax deduction today. But earlier, you mentioned this is an estate planning tool.

SPEAKER_00 10:42

It is.

SPEAKER_01 10:43

What happens when you eventually pass away? Doesn't the IRS come knocking for estate taxes?

SPEAKER_00 10:48

That is the next major advantage. The assets you put into the CRT are legally removed from your taxable estate. Yeah. And this is absolutely critical right now due to the legislative environment.

SPEAKER_01 10:58

You're talking about the 2026 sunset, right?

SPEAKER_00 11:00

Yes. In 2026, the historically high federal estate tax exemption limits, which were put in place by the Tax Cuts and Jobs Act, are sunsetting. They were dropping by roughly half.

SPEAKER_01 11:09

So estates that were previously totally safe from estate taxes are suddenly going to be in the crosshairs.

SPEAKER_00 11:15

Precisely. We are looking at estates in the $7 million to $10 million range, suddenly being exposed to a brutal 40% federal estate tax.

SPEAKER_01 11:24

Ouch.

SPEAKER_00 11:24

Yeah. For families hovering near that cliff, a CRT is a highly effective way to proactively shrink their taxable estate footprint, moving the asset completely out of the IRS's reach while still retaining a cash flow from it while they're alive.

SPEAKER_01 11:39

So those first few benefits feel like um blunt force trauma to your tax bill, just massive immediate savings. But the deeper we go into the Davies wealth strategies, the more it feels like precision wealth management.

SPEAKER_00 11:52

Really is.

SPEAKER_01 11:52

Let's talk about the income you receive from the trust. How is that actually taxed when it hits your bank account?

SPEAKER_00 11:57

This brings us to a concept called income smoothing. When the trust pays you your income stream every year, the IRS doesn't just look at it as one lump sum of generic income.

SPEAKER_01 12:07

They don't.

SPEAKER_00 12:07

No, they use a very specific four-tier taxation system. Think of the trust as a dispenser with four different buttons. It pays out ordinary income first, then capital gains, then tax exempt income, and finally a tax-free return of your original principal.

SPEAKER_01 12:20

Okay, so the IRS forces you to take the highest taxed money out first. That seems tricky.

SPEAKER_00 12:25

They do. But a sophisticated trustee understands this mechanism. They can manage the trust's underlying investments to intentionally influence which tier your income falls into.

SPEAKER_01 12:36

Give me an example of that.

SPEAKER_00 12:38

Well, for example, if they invest heavily in growth stocks that don't pay dividends, there is no ordinary income being generated inside the trust. Therefore, when you get your payout, the trustee skips tier one and dispenses tier two, which is capital gains.

SPEAKER_01 12:51

And those are taxed at a significantly lower rate.

SPEAKER_00 12:54

Exactly. It is an active mechanism for managing your annual tax bracket.

SPEAKER_01 12:58

Which ties perfectly into another precision strategy, which is managing your Medicare premiums. Because for anyone nearing Medicare age, there is a hidden tax tripwire called IRMAA.

SPEAKER_00 13:09

Yes, IRMA, the income-related monthly adjustment amount. It's essentially a stealth surcharge on your Medicare Part B and Part D premiums if your income is deemed too high.

SPEAKER_01 13:19

And the tripwire is lower than most affluent retirees realize, right?

SPEAKER_00 13:23

Much lower. In 2026, IRNAA surcharges begin hitting single filers at around $106,000 of modified adjusted gross income and married filers at $212,000.

SPEAKER_01 13:36

So imagine you don't use a CRT. You just sell that $2 million stock portfolio directly. Your income for that year spikes massively. You don't just pay the capital gains tax.

SPEAKER_00 13:46

No, you trigger a cascade effect. That massive sale pushes your income so high that you hit the absolute maximum Medicare surcharge tiers. And because Medicare uses a two-year look back period, a spike in 2024 hits your premiums in 2026.

SPEAKER_01 14:01

Sometimes it can affect you for two consecutive years.

SPEAKER_00 14:04

Exactly. But by using a CRT, you are acting like a slow drip faucet.

SPEAKER_01 14:07

Yeah.

SPEAKER_00 14:08

You spread that massive gain out over decades of small income payouts, completely avoiding overflowing the bucket and hitting those IRMAA tripwires.

SPEAKER_01 14:15

Location plays a huge role in this, too, doesn't it? I mean the Davies team is based in Stewart, Florida.

SPEAKER_00 14:19

Aaron Ross Powell Location is a massive multiplier for this strategy. Florida has a 0% state income tax. When a Florida resident contributes an asset to a CRT, they're escaping both federal and state capital gains exposure. We see this constantly with relocation clients.

SPEAKER_01 14:33

Like people moving from California.

SPEAKER_00 14:35

Exactly. If you're escaping a high-tax state like California, which has a top state capital gains rate of 13.3%, the math on a CRT becomes undeniably potent. You're dodging a combined federal and state tax hit that could approach 37% on the sale.

SPEAKER_01 14:52

Okay, but let's address the elephant in the room here. This all sounds incredible for you, the donor, while you are alive. But what does this mean for your kids? I mean, if you give the remainder of this multi-million dollar trust to a charity, aren't you just disinheriting your family for a tax break?

SPEAKER_00 15:08

That is the single most common objection advisors here, and you know, it is a completely valid fear. But you don't have to choose between your heirs and the charity. Affluent families use a mechanism called the wealth replacement strategy.

SPEAKER_01 15:19

How does that actually work in practice?

SPEAKER_00 15:21

You take a portion of the income stream you are receiving from the CRT, perhaps combining it with the hard cash you saved on your income taxes from that upfront deduction, and you use it to pay the premiums on a life insurance policy.

SPEAKER_01 15:33

Oh, I see.

SPEAKER_00 15:34

But you don't just hold the policy yourself, you house it inside an irrevocable life insurance trust or an ILite.

SPEAKER_01 15:41

Let me push back on that though. Life insurance premiums for a multimillion dollar policy on a 60-year-old aren't cheap. Doesn't paying those premiums completely eat up the income you are getting from the CRT?

SPEAKER_00 15:53

It does use a portion of the income, sure. But remember the math. You are generating a higher income stream to begin with, because you didn't lose 25% to 37% of the assets value to taxes on day one.

SPEAKER_01 16:05

Right. You have a much larger principal base generating that yield.

SPEAKER_00 16:09

Exactly. When you pass away, the remaining assets in the CRT go to the charity. Meanwhile, the life insurance policy inside the ILIT pays out a death benefit to your children.

SPEAKER_01 16:18

And because the trust owns the policy, not you.

SPEAKER_00 16:21

That death benefit is completely tax-free and sits outside of your taxable estate.

SPEAKER_01 16:25

That is fascinating. You are essentially using the tax savings to fund the insurance premiums.

SPEAKER_00 16:31

We call this giving twice on the same dollar. You fully fund a charitable legacy, and your kids receive the exact same level of wealth, completely tax free. It completely removes the friction between philanthropy and family legacy.

SPEAKER_01 16:45

But let's be realistic, this isn't for everyone. Let's talk about who actually uses this and what the strict rules of the road are. Because comparing this to other strategies like a donor-advised fund, it seems much more complex.

SPEAKER_00 16:57

They are very different tools. A donor-advised fund gives you a great upfront tax deduction and lets you control charitable grants, but it's just a one-way street. It provides zero income back to you.

SPEAKER_01 17:08

What about qualified opportunity zones?

SPEAKER_00 17:10

QOZs can defer capital gains, but you are forced to invest in specific distressed real estate. There is no charitable deduction and no guaranteed income stream. A CRT is really the only tool in the toolkit that offers a lifetime income stream to you and full capital gains deferral on the sale.

SPEAKER_01 17:27

But there are guardrails. This isn't a DIY project you just set up online over the weekend.

SPEAKER_00 17:31

Far from it. Practically speaking, because of the setup costs and ongoing administration, you generally need a minimum of $500,000 to $1 million of appreciated assets to justify the structure.

SPEAKER_01 17:43

And there are administrative fees.

SPEAKER_00 17:45

Yes. The trust has to file annual tax returns. You have to hire appraisers for hard-to-value assets like real estate. The administrative and legal fees typically run between $1,500 and $5,000 a year.

SPEAKER_01 17:57

And timing is everything, especially for business owners looking to sell.

SPEAKER_00 18:01

Yes. There is a lethal trap called the step transaction doctrine.

SPEAKER_01 18:05

How does that catch people?

SPEAKER_00 18:06

Let's say you are selling your business.

SPEAKER_01 18:28

Wow. So you have to fund the trust before the sale is finalized.

SPEAKER_00 18:32

Exactly. The charity needs to bear some genuine economic risk.

SPEAKER_01 18:35

And we absolutely have to reiterate the irrevocability rule. Once you transfer this asset into the trust, you cannot change your mind. It is not an emergency fund.

SPEAKER_00 18:44

No, it's like pouring concrete. Once it sets, it is permanent. You can usually change which charity receives the money at the end, assuming your initial trust document allows for that flexibility. But you absolutely cannot crack open the concrete and take back the principal. It is gone from your control.

SPEAKER_01 19:00

Which is why this requires genuine long-term commitment. It is a sophisticated legacy and income vehicle, not a checking account. Spot on. So bringing this all together, why does Davies Wealth Management utilize the strategy for their clients? Because true wealth management isn't just about chasing a high return on a stock chart, it is about optimizing what you actually get to keep.

SPEAKER_00 19:22

Exactly.

SPEAKER_01 19:22

It's about living comfortably on your terms, giving meaningfully to causes you care about, and leaving a family legacy that reflects your values without being unnecessarily penalized by the tax code.

SPEAKER_00 19:33

And executing that requires intense coordination. As fee-based fiduciaries, a firm like Davies isn't just selling you a trust document. They are coordinating this incredibly complex dance with your CPA and your estate planning attorney to make sure the trust is structured, funded, and administered perfectly.

SPEAKER_01 19:51

Because the cost of getting it wrong is huge.

SPEAKER_00 19:54

Oh, failing that 10% remainder test or triggering a step transaction, it's simply too high to leave to chance.

SPEAKER_01 19:59

So if you are listening to this and realizing you have an asset, a business, real estate, concentrated stock that fits this profile, you need to take action before you decide to sell. Davies Wealth Management has a three-minute financial wellness quiz that gives you a personalized snapshot of your estate and tax planning gaps.

SPEAKER_00 20:16

That's a great starting point.

SPEAKER_01 20:18

You can also book a complimentary no obligation call directly with Thomas Davies at TDillwealth.net to walk through your specific scenario and see if the math makes sense for you.

SPEAKER_00 20:26

I want to leave you with a final thought to ponder regarding everything we've discussed today. We spend so much of our lives trying to hold on to every single dollar of our wealth tightly in our own fists, terrified of taxes, terrified of market loss.

SPEAKER_01 20:41

Right.

SPEAKER_00 20:42

But what if the ultimate financial flex isn't retaining absolute total control of your assets until the day you die? What if true financial mastery is orchestrating exactly how your wealth impacts the world long after you're gone, while legally forcing the IRS to inadvertently help fund your retirement in the process?

SPEAKER_01 21:01

It really changes the whole perspective on wealth because if you have the right strategy, you don't have to hold on to the apple orchard forever just to enjoy the harvest. You just need to know how to plant the right trees. Thanks for joining us on this deep dive. We'll see you next time.