1715 Treasure Coast Financial Wellness with Thomas Davies

Roth Conversion Ladder: Cut Taxes in Retirement Over 5 Years

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What if the biggest tax bill of your retirement is completely avoidable? If you have $1 million or more sitting in a traditional IRA or 401(k), every dollar coming out will eventually be taxed as ordinary income. The real question is when you pay — and at what rate. In this episode, we break down the Roth conversion ladder strategy and how a disciplined five-year approach can dramatically reduce your tax burden in retirement. We cover how to sequence conversions, how to avoid common mistakes that trigger unnecessary taxes, and why this is one of the most powerful tools in long-term retirement planning and wealth management. Whether you are already retired or approaching it, this episode will change how you think about your tax-deferred accounts. Ready to talk? Schedule a complimentary discovery call at TDWealth.net. For educational purposes only. Not investment advice. 📖 Full show notes: https://tdwealth.net/roth-conversion-ladder-cut-taxes-in-retirement-over-5-years/

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SPEAKER_00

Imagine you spent, you know, your entire life working, saving, and just diligently investing.

SPEAKER_01

Right, doing everything exactly by the book.

SPEAKER_00

Exactly. You played by all the conventional rules, you maxed out your 401k, you deferred your taxes, and you successfully built this massive multimillion dollar retirement nested.

SPEAKER_01

It feels great. You feel incredibly secure.

SPEAKER_00

Oh, absolutely. Maybe even a little proud of what you've accomplished. But uh what if you were to suddenly realize that what you've actually built isn't just a nested?

SPEAKER_01

Oh.

SPEAKER_00

Yeah. What if it's actually a massive ticking tax time bomb?

SPEAKER_01

Yeah. That can be a really chilling moment for a retiree. I mean, when they finally look past that top line number of their net worth and actually calculate the deferred tax liabilities, just, you know, waiting for them.

SPEAKER_00

Right, because it's not all theirs.

SPEAKER_01

Exactly. The illusion of total ownership just crashes headfirst into the reality that the IRS is essentially a silent partner in all of those traditional retirement accounts.

SPEAKER_00

Aaron Powell Wow, a silent partner. That is a brutal way to look at it, but it's so true. So today, we are focusing on how you can buy out that silent partner on your own terms.

SPEAKER_01

Aaron Powell A very necessary buyout.

SPEAKER_00

For sure. We are unpacking a really comprehensive strategy guide created by Davies Wealth Management. They're a fee-based fiduciary advisor down in Stewart, Florida. Yep. And they put this deep dive together for the 1715 Treasure Coast Financial Wellness Podcast. And the whole focus is this thing called the Roth Conversion Ladder.

SPEAKER_01

Aaron Ross Powell Specifically how this multi-year strategy applies to high net worth retirees. Because it's uh it's very different for them.

SPEAKER_00

Yeah, it really is. And the documentation they've put together provides this incredibly dense, totally actionable blueprint.

SPEAKER_01

Aaron Powell It's fantastic. It moves way beyond your standard run-of-the-mill retirement advice. It really gets into the granular mechanics of preserving wealth when you have complex overlapping income streams.

SPEAKER_00

Okay, let's unpack this. Before we get into how a conversion ladder actually works to shield your money, we really need to understand the fundamental problem here.

SPEAKER_01

Aaron Powell Right. The why.

SPEAKER_00

Yeah. The why. Because we've always been told that deferring taxes into traditional IRAs and 401ks is like the absolute smartest thing a high earner can do.

SPEAKER_01

Which it is. Or, well, it was.

SPEAKER_00

Right. So why does this suddenly turn into a massive crisis for high net worth individuals when they hit their 70s?

SPEAKER_01

Aaron Powell Well, the conventional wisdom to defer your taxes was absolutely the right move during your peak earning years. Every dollar you put into those pre-tax accounts was a dollar they didn't get taxed at your highest marginal rate back then.

SPEAKER_00

That makes total sense.

SPEAKER_01

Plus, that money got decompound over decades, right? Without the constant drag of annual taxation pulling it down.

SPEAKER_00

Aaron Powell So you were basically getting a tax break on the front end and then this accelerated growth on the back end.

SPEAKER_01

Exactly. It's a sweet deal. But the government, you know, they don't let you defer those taxes forever.

SPEAKER_00

Yeah, eventually they want their cut.

SPEAKER_01

They absolutely do. And the IRS mandate is entirely unavoidable. Under the current tax law framework, specifically the updated rules in Secure 2.0, you are legally required to start pulling money out of those tax-deferred accounts when you reach age 73.

SPEAKER_00

Okay, age 73. And these are the RMDs, right?

SPEAKER_01

Right. Required minimum distributions. The government actually uses this very specific uniform lifetime table to calculate exactly how much you must withdraw every single year.

SPEAKER_00

And just to be super clear for you listening, these are mandatory distributions. It completely does not matter whether you actually need the money to live on or pay your bills.

SPEAKER_01

Oh, the IRS does not care at all about your personal cash flow needs. And for a high net worth retiree, the sheer scale of these mandatory withdrawals is where the mass just gets brutal.

SPEAKER_00

Walk me through the math.

SPEAKER_01

So Davies Wealth Management uses this highly realistic baseline example in our guide. Let's say you've accumulated a $5 million balance in your traditional IRA over your career.

SPEAKER_00

Okay, $5 million.

SPEAKER_01

When you turn $3, that IRS formula dictates that your very first RMD will be roughly $188,000.

SPEAKER_00

Wow. Wait, so on day one of being $73, you suddenly have $188,000 of taxable income just forced into your lap.

SPEAKER_01

Forced right into your lap. And every single penny of that is taxed as ordinary income.

SPEAKER_00

That is wild.

SPEAKER_01

And it gets worse. Consider that someone with a $5 million portfolio almost certainly has other income streams, right?

SPEAKER_00

For sure.

SPEAKER_01

They might be collecting maximum social security benefits. Maybe receiving a corporate pension or generating passive income from commercial real estate.

SPEAKER_00

Right. They aren't just sitting around with zero income.

SPEAKER_01

Exactly. So that $188,000 RMD gets stacked right on top of that baseline income, which can easily launch a retiree straight into the highest federal tax brackets.

SPEAKER_00

We're talking like the 32% or even the 37% tier.

SPEAKER_01

Yes.

SPEAKER_00

Instantly.

SPEAKER_01

You know, I look at this scenario kind of like a pressure cooker. For 30 or 40 years, you've been building up all this incredible pressure that's your wealth compounding inside this sealed tax-deferred pot.

SPEAKER_00

That's a great analogy.

SPEAKER_01

But then at age 73, the government steps in and just rips the release valve wide open. And if you aren't prepared to control that steam, you just get completely scalded by taxes. You really do. You lose all autonomy over your own tax rate. However, there is a strategic window to act before the government forces that valve open.

SPEAKER_00

The gap years.

SPEAKER_01

Yes. Financial planners refer to this critical window as the gap years. Trevor Burrus, Jr.

SPEAKER_00

Okay, let's define that. The gap years are basically that period between the day you retire and you know stop earning a massive salary and the day you turn 73 when those RMDs actually begin.

SPEAKER_01

Aaron Powell Right. That's exactly it. For a high net worth individual retiring in their early 60s, this could be a 10 to 15 year window where their earned income just plummets, but their massive RMDs haven't kicked in yet.

SPEAKER_00

So their income is artificially low.

SPEAKER_01

Right. And this period of artificially low income is the exact moment to strike. This is when you execute the Roth conversion ladder.

SPEAKER_00

Okay, let's get into the actual mechanics of this ladder because we are talking about systematically shifting money from that fully taxable traditional IRA into a permanently tax-free Roth IRA. But to do this effectively, the Davies Guide emphasizes that you first have to map your income floor. How does a retiree actually figure that out when their income is coming from like so many different places?

SPEAKER_01

Well, before you can proactively manage your tax bracket, you really need a hyperaccurate projection of your baseline income for every single year of your gap window.

SPEAKER_00

So you have to be super detailed.

SPEAKER_01

Very. You have to forecast when your deferred compensation payouts begin and end. You need to map out whether you're claiming Social Security at 65 or optimizing it by waiting until 70.

SPEAKER_00

Right.

SPEAKER_01

You have to account for dividend yields and rental income. Only when you aggregate all of those streams do you find your true income floor.

SPEAKER_00

Because once you know where your floor is, you can see exactly how much headroom you have before you bump your head on the ceiling of the next tax bracket.

SPEAKER_01

Exactly. And that is where the conversion targets actually come into play.

SPEAKER_00

Okay, break that down for me.

SPEAKER_01

So the tax code is progressive, meaning your income is taxed in chunks at increasing rates. Once you know your baseline floor, you look at the federal tax brackets. Take a married couple filing jointly in 2026. Okay. The 24% tax bracket caps out at just under $395,000 of taxable income. If your baseline income floor is mapped at $150,000, you have nearly $245,000 of empty room left in that 24% bracket.

SPEAKER_00

Oh, I see. So the latter strategy is to convert exactly enough of your traditional IRA to a Roth to perfectly fill up that remaining $245,000 in the 24% bracket.

SPEAKER_01

Yes.

SPEAKER_00

Deliberately stopping right before you spill over into the 32% bracket.

SPEAKER_01

Precisely.

SPEAKER_00

And you just do this sequentially, year after year.

SPEAKER_01

Right, filling up those lower brackets.

SPEAKER_00

Okay, I have to push back on this step-by-step approach, though. Because if moving this money into a permanently tax-free Roth IRA is so incredibly beneficial for wealth preservation, why are we tiptoeing around with a ladder?

SPEAKER_01

What do you mean?

SPEAKER_00

Well, if I have a $3 million traditional IRA, why not just try to force a fire hose amount of water through a garden hose size tax bracket? Like, why not just rip the band-aid off, convert all three million on day one of retirement, pay the massive tax bill, and enjoy tax-free growth forever.

SPEAKER_01

What's fascinating here is how often human psychology directly conflicts with optimal tax mathematics.

SPEAKER_00

Tell me about it.

SPEAKER_01

People are inherently drawn to immediate resolution. They just want the tax liability eliminated today. But executing a lump sum conversion of that magnitude is actually one of the most financially destructive mistakes a retiree can make.

SPEAKER_00

Oh wow.

SPEAKER_01

Yeah. You've just voluntarily surrendered over a million dollars of your wealth to the IRS in a single swipe.

SPEAKER_00

Just writing a massive check for no reason.

SPEAKER_01

Exactly. The latter is entirely about bracket management. By spreading that $3 million conversion out over a decade, say, converting $300,000 annually, you keep every single dollar shielded within that 24% bracket.

SPEAKER_00

That makes total sense when you put it like that.

SPEAKER_01

Right. You're preserving 13% of your total wealth simply by deploying patience and precision.

SPEAKER_00

Okay, so bracket management solves the federal income tax problem. But the Davies guide makes it very clear that you can't just stare at the standard IRS income tax bracket.

SPEAKER_01

I definitely cannot.

SPEAKER_00

There are these invisible tripwires hiding in the background of the tax code that can just completely blow up this strategy if you aren't careful. I want to talk about IRMA and the NIT.

SPEAKER_01

Yes. These are the hidden mechanisms that often catch self-directed investors completely off guard.

SPEAKER_00

Let's start with IRMA, which stands for the Medicare Income Related Monthly Adjustment Amount. I've heard horror stories from retirees who got hit with massive surprise Medicare premiums because of some, you know, hidden income formula. Is that what we are dealing with here?

SPEAKER_01

It is. And the mechanism behind it is incredibly insidious. IRMAA is essentially a surcharge added to your standard Medicare Part B and Part D premiums. But the formula isn't based on your standard taxable income.

SPEAKER_00

It's not.

SPEAKER_01

No, it's based on your modified adjusted gross income or MEGI. And the real trap here is that the government looked at your MAGI from two years prior to determine your current surcharge. Trevor Burrus, Jr.

SPEAKER_00

Wait, a two-year look back. Yes. So a financial move I make today can suddenly haunt my health care costs 24 months from now.

SPEAKER_01

Exactly.

SPEAKER_00

And how does a Roth conversion impact this modified adjusted gross income?

SPEAKER_01

Aaron Powell Well, a Roth conversion is treated as ordinary income. So when you convert $200,000, your MGI artificially inflates by $200,000 for that specific year.

SPEAKER_00

Okay, I follow.

SPEAKER_01

In 2026, for a married couple filing jointly, the very first IRMAA surcharge kicks in when your May GI crosses approximately $212,000. And unlike federal tax brackets, which are graduated and smooth, IRMAA operates on brutal cliff effects.

SPEAKER_00

Wait, I want to make sure I'm really grasping the math on this clip. So if I do a precise Roth conversion and my MGI lands at exactly $211,999, I pay the baseline Medicare premium, right?

SPEAKER_01

Right.

SPEAKER_00

But if I convert just $1 more.

SPEAKER_01

Just one dollar.

SPEAKER_00

And my MGI hits $212,000.

SPEAKER_01

That single dollar pushes you completely over the cliff and you trigger the surcharge for the entire calendar year.

SPEAKER_00

Are you kidding?

SPEAKER_01

Nope. And there are multiple escalating IRMA tiers. As your income rises, the surcharges become increasingly punitive. A careless Roth conversion that pushes you over a higher IRMAA cliff could easily add $5,000, $10,000, or even $15,000 in unexpected non-deductible Medicare costs.

SPEAKER_00

That completely destroys the return on investment of the conversion you just made.

SPEAKER_01

It absolutely wipes it out.

SPEAKER_00

And IRMAA isn't the only trapdoor out there. The guide also heavily emphasizes the NIIT, the net investment income tax. How does an ordinary income conversion trigger an investment tax?

SPEAKER_01

Aaron Powell It all comes back to that inflated, modified, adjusted gross income. The NIIT is a 3.8% surtax on your investment income, things like capital gains, dividends, and rental income.

SPEAKER_00

Okay.

SPEAKER_01

For a married couple filing jointly, this surtax activates when your MEI crosses the $250,000 threshold. That is the exact mechanism. You might model a conversion thinking you're only paying the 24% income tax rate. But if that conversion inflates your May GI past 250K, it triggers the 3.8% NIT on your dividends and capital gains while simultaneously triggering a top-tier IRMAA surcharge two years later.

SPEAKER_00

That is just brutal.

SPEAKER_01

When you compound those intersecting penalties, the effective marginal tax rate on your converted dollars can quietly exceed 40%.

SPEAKER_00

Wow. You know, this perfectly illustrates why high net worth advice is fundamentally different from mass market financial media. Absolutely. Like a generic blog post will just tell you, hey, fill up the 24% bracket. But a high net worth individual isn't just looking at one variable. You are threading a microscopic needle between federal brackets, Medicare cliffs, and investment surtaxes.

SPEAKER_01

The mass market approach just assumes isolation. The high net worth approach recognizes that every single financial threshold is dynamically linked.

SPEAKER_00

So we've navigated the gauntlet of federal taxes and hidden surcharges. Now the Davies Guide zooms out to look at the macro picture, specifically geography and legacy. Here's where it gets really interesting.

SPEAKER_01

It does.

SPEAKER_00

Let's talk about where you physically live when you execute this ladder.

SPEAKER_01

State domicile is actually one of the most powerful levers a retiree can pull. The contrast presented in the strategy guide is stark. They look at executing a conversion ladder in California versus executing one in Florida.

SPEAKER_00

And with Davies wealth management being headquartered in Stewart, Florida, they obviously have a front row seat to this specific migration pattern.

SPEAKER_01

They see it every day. And the arithmetic of that migration is staggering. California levies a state income tax that can scale up to 13.3%.

SPEAKER_00

Yikes.

SPEAKER_01

Florida, conversely, has zero state income tax. Zero.

SPEAKER_00

That's a massive difference.

SPEAKER_01

So if a high net worth retiree is planning accumulative $500,000 in Roth conversions over their gap years, doing that while legally domiciled in California means forfeiting up to 13.3% of that wealth to the state franchise tax board.

SPEAKER_00

So you're saying the sunshine in California is great, but avoiding a $65,000 state tax hit on a half million dollar conversion that makes the Florida beaches look significantly more inviting.

SPEAKER_01

I'd say so. By strategically coordinating your relocation, waiting to establish your Florida domicile before accelerating the heavy rungs of your conversion ladder, you permanently preserve that $65,000.

SPEAKER_00

That is just smart planning.

SPEAKER_01

It is a massive swing in net worth, dictated entirely by geography and sequencing.

SPEAKER_00

Which naturally leads us to the final consideration of the ladder: generational wealth. We spend so much time worrying about our own taxes, but how does shifting money into a Roth impact the people who actually inherit it?

SPEAKER_01

If we connect this to the bigger picture, the true compounding value of a Roth conversion ladder is often realized long after the original account owner has passed away. It is arguably the most potent estate planning tool available today.

SPEAKER_00

That's interesting because when we talk about estate planning, people usually jump straight to the federal estate tax exemption.

SPEAKER_01

Right. The death tax.

SPEAKER_00

Yeah. And in 2026, that exemption is massive. It's sitting at $13.9 million per individual, meaning a married couple can shield nearly $28 million from federal estate taxes. Exactly. So for a lot of multimillionaires, the actual death tax isn't really the primary threat.

SPEAKER_01

It's not. The primary threat to generational wealth today is actually income tax, and it's driven entirely by the death of the stretch IRA.

SPEAKER_00

The stretch IRA. Explain that.

SPEAKER_01

Well, under the secure 2.0 legislation, if a non-spouse heir, like an adult child, for example, inherits a traditional tax-deferred IRA, they are legally barred from stretching those distributions out over their lifetime.

SPEAKER_00

Oh, I see.

SPEAKER_01

Yeah. They are mandated to empty that entire account within 10 years.

SPEAKER_00

The 10-year depletion rule. And because it's a traditional IRA, every dollar they are forced to withdraw over that decade is taxed as ordinary income.

SPEAKER_01

Exactly. And consider the demographic collision here. When do people typically inherit money from their parents?

SPEAKER_00

Usually when the parents pass away in their late 80s or 90s.

SPEAKER_01

Right. This means the children inheriting the IRA are typically in their mid-50s or early sixties.

SPEAKER_00

Oh wow. They are in their absolute peak earning years.

SPEAKER_01

Precisely. Your heirs are likely already sitting in a high tax bracket due to their own mature careers and investments. Now they inherit a three million dollar traditional IRA, and the IRS forces them to drain $300,000 a year from it. Yes. You have inadvertently forced your children into the highest possible tax brackets, allowing the government to confiscate a huge percentage of their inheritance.

SPEAKER_00

But if you had taken advantage of your lower income gap years to convert that money to a Roth, the dynamic completely flips. Right. The rule is the same.

SPEAKER_01

However, every single distribution they take over that decade is 100% income tax-free. By deliberately paying a managed 24% tax rate during your gap years, you shield your heirs from paying a forced 37% or higher during their peak earning years.

SPEAKER_00

That is just an incredible gift to leave your kids. And the guide details some incredible synergy for creating even more conversion room during those gap years using charitable giving.

SPEAKER_01

Yes. Strategies like qualified charitable distributions or QCDs.

SPEAKER_00

Right. How does giving to charity actually help you convert more money to a Roth?

SPEAKER_01

Well, a QCD allows you to send money directly from your IRA to a qualified charity. Because the money never actually touches your personal bank account, it bypasses your modified adjusted gross income entirely.

SPEAKER_00

Oh, so it just doesn't count.

SPEAKER_01

Exactly. It never even shows up on line 11 of your 1040 tax return. By using QCDs to fulfill any required distributions or philanthropic goals, you actively suppress your income floor.

SPEAKER_00

That is so smart.

SPEAKER_01

It creates a larger void in the lower tax brackets, allowing you to convert larger tranches of traditional IRA money to Roth without tipping into the higher punitive brackets.

SPEAKER_00

It's a brilliant way to support causes you care about while simultaneously weaponizing the tax code to your advantage.

SPEAKER_01

Aaron Powell Weaponizing the tax code. I love that phrasing.

SPEAKER_00

Okay. So we've built the theoretical architecture of the strategy. We understand the RMD threat, the brackets, the tripwires, and the generational impact. But a brilliant strategy executed poorly is just a disaster.

SPEAKER_01

It usually is.

SPEAKER_00

Let's talk about physical execution because the Davies Guide flags one crucial, unforced error that just completely ruins the math of the ladder.

SPEAKER_01

The mechanics of how you pay the tax bill on the conversion dictate the ultimate success of the strategy.

SPEAKER_00

Let's look at a real world scenario. Let's say I decide to convert $200,000 from my traditional IRA to my Roth this year. The IRS wants their 24% cut, which is $48,000. It seems incredibly convenient to just check a box and have the brokerage withhold that $48,000 directly from the conversion amount, right?

SPEAKER_01

It is very convenient and it is a catastrophic mathematical error.

SPEAKER_00

Really?

SPEAKER_01

Yes. If you withhold the taxes from the conversion itself, only $152,000 actually arrives in the Roth IRA. The entire purpose of this strategy is to maximize the principal balance inside the tax-free shelter so it can compound over decades.

SPEAKER_00

Oh, I see. So the $48,000 tax bill absolutely must come from a completely separate outside account.

SPEAKER_01

It must. It needs to come from a taxable brokerage account, a high yield savings account, or cash reserves. By paying the toll with outside dollars, you ensure the full $200,000 lands in the Roth.

SPEAKER_00

That makes a ton of sense.

SPEAKER_01

The difference in tax-free compounding between a $152,000 principal and a $200,000 principal over a 20-year timeline is just staggering. You never ever cannibalize the tax-advantaged asset to pay the tax liability.

SPEAKER_00

Got it. Another execution detail the guide dives into is the five-year rule. This sounds like something that only applies in very specific situations. Who actually needs to worry about sequencing their conversions around a five-year clock?

SPEAKER_01

The five-year rule is basically the primary hurdle for early retirees. Every individual Roth conversion you execute starts its own unique five year holding clock.

SPEAKER_00

Okay.

SPEAKER_01

If you are under the age of 59 and a half, you cannot withdraw the principal of that specific conversion without facing a 10% early withdrawal penalty until its five year clock has expired.

SPEAKER_00

So if I'm, say, a corporate executive who steps away at age 55, and my plan is to actually live off these converted Roth funds. Before I hit 59 and a half, I can't just convert and immediately spend it.

SPEAKER_01

No, you have to perfectly sequence the rungs of your ladder. You convert money at age 55 so it becomes penalty-free at 60. You convert at 56 so it's available at 61.

SPEAKER_00

Wow, so you really have to plan ahead.

SPEAKER_01

You do. It requires projecting your exact cash flow needs half a decade in advance. For retirees over 59 and a half, this specific penalty rule largely disappears, allowing much more flexibility.

SPEAKER_00

All of these overlapping complexities really highlight the overarching philosophy of Davies wealth management, which is a conversion ladder is not a set it and forget it algorithm.

SPEAKER_01

Definitely not. Tax laws are rewritten constantly. The stock market surges, unexpectedly throwing off massive capital gains that alter your income floor.

SPEAKER_00

Life happens, right?

SPEAKER_01

Exactly. You might sell a vacation property or receive an inheritance. Every single life event shifts the variables of your baseline income. The latter demands rigorous annual recalibration.

SPEAKER_00

And this really speaks to the core value of working with a fee-based fiduciary. They aren't running these complex multi-year projections just to sell you an annuity or generate some quick transaction commission. Not at all. A fiduciary is legally bound to provide advice that serves your best interests over the long term. It's about building a collaborative brain trust, right? Integrating these wealth management strategies directly with your CPA and your estate attorney.

SPEAKER_01

This raises an important question for you listening to ask yourself. Is your current retirement strategy an actual multi-year blueprint? Or is it just reactionary guesswork?

SPEAKER_00

That is the big question.

SPEAKER_01

Are you just passively waiting to see what your CPA tells you you owe every April? Or are you actively manipulating your tax liabilities a decade in advance?

SPEAKER_00

So what does this all mean? It means your retirement accounts are not isolated buckets of money just sitting in a vacuum. They are deeply interconnected ecosystems.

SPEAKER_01

Well said.

SPEAKER_00

Every dollar you move sends a ripple effect across your federal tax bracket, your Medicare premiums, your state tax liabilities, and the ultimate legacy you leave behind for your children.

SPEAKER_01

Coordinated forward-looking tax planning is consistently proven to be one of the highest value services a financial advisor can deliver. Generating returns on a portfolio is really only half the battle. The other half is structurally shielding those returns from confiscation.

SPEAKER_00

We have covered a tremendous amount of ground today, unpacking Davies Wealth Management's Roth Conversion Ladder Strategy for the 1715 Treasure Coast Financial Wellness Podcast. It is. Think about that mandatory 10-year depletion roll rating for them. If you successfully build a $5 million nest egg, but your children inherit it as a mandatory, heavily taxed burden during their highest earning years, did you actually build generational wealth, or did you just build a generational tax bill for the IRS? Something to think about.