Chapter 19 Retirement and Estate Tax for US Citizens and Green-Card Holders

Estate Tax and Retirement Accounts for US Persons

This chapter is written specifically for US citizens and green-card holders (US Persons). It covers the RMD tax bomb inside traditional retirement accounts, Roth conversion tactics, the PFIC trap of foreign funds, FBAR/FATCA reporting obligations, and the debt deduction and exemption of the US estate tax (the endgame of Buy, Borrow, Die).

A reminder: the US tax content described in this chapter (RMD, Roth conversion, step-up in basis, PFIC, FBAR/FATCA, estate tax, gift tax, and so on) is a compilation of publicly available provisions from the US IRS and related regulations, benchmarked against the tax law in effect on the release date of the cited CLEC videos. US tax law and its interpretive rulings may change at any time; for your own actual filing, cross-border tax planning, and the timing and size of Roth conversions, please consult a qualified CPA, Enrolled Agent, or registered agent. The editor of this book is not a tax professional recognized by the US IRS, and nothing in this book constitutes case-specific tax advice or tax-planning services.

For US citizens and green-card holders, worldwide assets fall under US tax jurisdiction. This is both a burden (worldwide reporting obligations) and an advantage (a high estate-tax exemption plus federal-income-tax-free qualified Roth distributions). This chapter fully unpacks the tax tactics that a US-person investor must master at the two critical moments of exiting in the retirement phase and passing on assets.

The RMD Tax Bomb Inside Traditional Accounts

Many people, in their younger years, greedy for an immediate income-tax deduction, pour large sums into a Traditional IRA or Traditional 401(k). Yet these pre-tax accounts face the required minimum distribution (RMD) rule imposed by the US Internal Revenue Service once the investor reaches the statutory age (under SECURE 2.0: those born 1951 to 1959 at age 73, those born from 1960 onward pushed to age 75, effective 2033; the actual starting age is governed by whatever the IRS SECURE 2.0 rules specify at the time).

Because with your Traditional IRA or Traditional 401(k), later on you will never finish paying the tax, because at 72 you will be forced into this RMD … you will pay tens of millions in tax. This is exactly why the Traditional IRA … (Video 00399)

(When Teacher James recorded the video, the RMD start age was 72; it has since been adjusted under SECURE 2.0 to 73 or 75, depending on birth year.) If an investor has genuinely carried out long-term index investing, by the age when RMDs kick in the assets in the account may already have climbed to several million or even tens of millions of US dollars. The IRS will compel a set proportion to be withdrawn every year, and all of these withdrawn funds get folded into that year’s personal income tax. This means an investor may be forced, after retirement, to face the penalty of the highest tax bracket, and a very large part of the capital painstakingly accumulated will be levied away directly, forming an extremely sizable tax drain.

A more extreme real case gives this threat a sense of scale:

Look, he has US$1.74 million in his IRA. If he never does a conversion and waits until the RMD to do the conversion, then he gets taxed at a very high rate. That US$1.74 million will later grow to more than US$88 million, and half of that must be paid in tax, so he would pay more than US$44 million. But if he uses a very low tax rate, he escapes it, and he can save tens of millions in tax. So the ordinary laborer would rather go work for a dozen years than lift a finger to save tens of millions. (Video 00499)

Lay the mathematical trajectory out: an investor currently has US$1.74 million in a Traditional IRA. If he does not proactively execute a Roth conversion and lets the funds compound at the QQQ-scale high speed of that case (about 14% to 15% annualized, an assumption specific to that video’s case, not this book’s forward-looking 12% baseline), then by the RMD start age of 73 the account may swell to more than US$88 million. At that point the RMD forced-withdrawal mechanism activates, and with the top US federal marginal rate of about 37% plus state tax that can reach 13%, the effective rate can hit 50%. In other words, of that US$88 million, more than US$44 million must be handed to the IRS.

But if this investor, during the low-income window after retirement (say ages 60 to 72), proactively executes a Roth conversion, converting to a Roth IRA in batches at low marginal rates, then converting the entire US$1.74 million in full may cost only a few million in tax (rather than more than US$44 million). Same principal, same compound growth, yet the net assets that finally land in hand may differ by US$30 million to US$40 million. The most ironic contrast is this: the ordinary laborer is willing to toil for a dozen years to earn a few million more, but unwilling to spend a few days understanding the Roth conversion mechanism and methodically carrying out the conversions, watching helplessly as tens of millions in assets are handed over to the IRS. This is the true motive behind the CLEC system’s repeated emphasis on aggressively converting to Roth during low-tax-rate periods: if you do not convert, the IRS converts for you, and it charges 50%.

Laying the numbers out makes it hit harder. If at age 61 a Traditional IRA holds US$1 million at a 10% annualized return, then by the RMD start age of 73 the account may already have grown to about US$3.14 million, with a first-year forced withdrawal of about US$118,000 (the divisor applicable at 73 is about 26.5). If the account reaches US$2 million at 15% annualized and you want to finish converting in the 10 years before RMDs begin, you would need to convert about US$399,000 a year, which keeps the post-retirement marginal rate stuck at the very top bracket throughout. All of these withdrawal and conversion amounts get folded into that year’s income, which is equivalent to detonating the post-retirement tax-rate pressure all at once.

The more dangerous fuse on this bomb is the moment of inheritance. When a Traditional IRA becomes an estate, it faces the devastating blow of double taxation:

Feel this devastating blow with concrete numbers: suppose a Traditional (pre-tax) IRA accumulates to US$20 million, and the total estate exceeds the 2026 federal estate-tax exemption of about US$15 million. The excess US$5 million is first hit with the top federal estate tax of 40%, about US$2 million, leaving the IRA at about US$18 million.

This US$18 million is still a pre-tax IRA. Under the current SECURE Act, most non-spouse heirs must fully withdraw the account within 10 years, and each withdrawal is taxed as ordinary income. If the withdrawals are poorly planned, concentrated in a few years, or dragged out until the final year and taken all at once, a large amount of principal and the appreciation over the period get crammed into the same year, pushing the heir up to nearly the top marginal rate (the federal top is about 37%, and some states add a state income tax on top). In other words, the same pool of assets is first brought into the estate-tax base through transfer at death, and then taxed a second time as ordinary income when the heir withdraws it. This is why the Traditional IRA is called double taxation in high-asset households, and why it eats up the greater part of a family’s inheritance (the actual tax burden still varies with the withdrawal strategy, the heir’s income, the state of residence, and other planning).

Put differently, the income tax that the decedent never paid during his lifetime detonates all at once at the moment of inheritance: the descendants must not only pay estate tax on the decedent’s behalf, they must also make up income tax using their own income-tax brackets. This is precisely the strongest motive for converting a Traditional IRA into a Roth as quickly as possible while still alive: a Roth IRA inheritance requires no income tax from the heir, and what is passed to the next generation is truly tax-paid money.

The Three Painless Steps of Roth Conversion

To dodge the bomb above, high-asset retirees should launch a three-step painless conversion. Step one, retire immediately so that salary income drops to zero, artificially manufacturing a tax trough. Step two, execute an aggressive Roth conversion during the low-tax-rate period. Step three, the tax bill generated by the conversion should never be paid by selling stock; instead, use a securities-backed loan (a pledged asset line, PAL) to borrow the money to pay the tax. This preserves the core assets and lets compounding run the full course inside the tax-free account.

When pledging enters the practical stage, the question of which account the funds sit in is more critical than most people imagine. Teacher James once gave clear instructions on the multi-account allocation of a US-person investor:

Putting cash in the Brokerage is wrong. The Base that the Brokerage pledges should all be QQQ. Your Traditional is where you put cash, understand? … The real cash should be one year’s worth of cash placed in the Roth, and everything else in the Traditional. And that one year’s US$300,000 in the Roth, when the trigger happens, when the market drops and a Margin Call is triggered, you can move this US$300,000 to the Brokerage and buy QQQ to top up the assets. (Video 00671, short-form)

Break this passage down into concrete rules:

Note that this rule does not conflict with the “345 cash rule” (a drawdown rate of 3% / 4% / 5% corresponding to cash of 30% / 40% / 50%). The overall cash proportion is still decided by the total allocation, but under the US tax architecture, the physical location of this cash should be concentrated in the Roth and the Traditional, not the Brokerage. Misplacing cash in the Brokerage means simultaneously losing pledge Base and the explosive growth space inside the Roth, a double tax waste.

A more advanced extension is the concept of asset location: the same pool of funds, placed in accounts of different tax character, produces wildly different results.

The principle is simple:

This asset split of low-growth in the Traditional and high-growth in the Roth is an advanced tax-optimization move after a Roth conversion has already been executed. Misplacing it (such as leaving QLD in the Traditional) detonates a double disaster when RMDs trigger.

The Painless Conversion Technique of Not Selling Stock at the Lows

To defuse this tax bomb, converting funds from a Traditional account into a Roth IRA is an essential defensive strategy for high-asset individuals. The timing of the conversion is extremely important. The best timing is in a year when the personal income-tax rate is lower (for example, kept within 24% or 32%), or to convert at the lows while the stock market is in a large pullback.

So if you convert early in the year, if you convert at the low, you can convert more shares. Likewise, if you want to convert US$100,000, you can convert a few more shares. (Video 00399)

In practice, converting does not mean the stock must be sold and cashed out to pay tax; instead, the assets can be transferred painlessly into the Roth account directly in the form of shares. For example, when QQQ’s price falls from US$500 to US$400, converting the same 100 shares means you only report income tax on US$40,000 of value at the low, whereas at the high you would owe tax on US$50,000. By transferring in kind at a market low, you not only move more shares into the tax-free account, you also greatly reduce that year’s tax burden.

The difference is even clearer viewed through a fixed conversion budget. Suppose you only intend to convert US$50,000 this year: at a price of US$500 you can only convert 100 shares; at a price of US$400 you can convert 125 shares, 25 more. If those 25 shares then keep compounding inside the Roth, over the long run they magnify into a real asset gap. This is the core value of “converting in a down market to gain shares.”

▲ Figure 19-1 Converting to Roth in a down market to gain shares, where the same budget moves more shares into the Roth for tax-free compounding at the lows

In addition, for an investor only a few years from retirement with a large Traditional IRA balance (say as high as US$1.7 million), it is all the more important to launch a phased conversion plan at once. Keep each year’s amount within a reasonable tax bracket (for example, converting US$100,000 to US$200,000 a year), ensuring that before the RMD age arrives, the water level of funds in the traditional account is lowered as far as possible into the tax-free Roth account. And for a young person whose salary is so high that direct Roth IRA contributions are barred, one should make good use of the Backdoor Roth IRA: place the funds first into a traditional IRA, then convert to the Roth IRA the very next day, so as to bypass the income-threshold limit.

If you are already 59 and a half and the taxable account has insufficient cash, there is an advanced tactic in practice: set tax withholding directly when executing the Roth conversion. The IRS will deduct the tax straight from the conversion amount, and at this age the early-withdrawal penalty is waived. Although this slightly reduces the principal entering the Roth, it lets the assets move quickly into the tax-free defensive zone, an excellent hedging compromise.

Take a practical calculation as an example: if you want to convert US$200,000 in a year and choose to withhold 10% federal tax, the IRS deducts US$20,000 straight from the conversion amount to pay tax, and only the remaining US$180,000 enters the Roth account. This maneuver lets a high-asset person past 59 and a half complete a cross-year tax conversion tactic without touching any cash from the ordinary taxable account at all.

The After-Tax Shrinkage of ROI and the Truth of Compounding

When evaluating investment performance, most people look only at the surface return on investment (ROI) and fail to factor in tax, the largest hidden cost of all. The funds in a Traditional IRA are in a not-yet-taxed state, while the funds in a Roth IRA are already tax-paid. Under long-term compounding, the real purchasing power that finally lands in the investor’s pocket differs by a world.

Because the government wants to take half your tax … so if your return rate is 10%, one chop and it becomes 6%. (Video 00405)

From a mathematical angle, a Traditional IRA is like a joint venture with the government: the more you earn, the more the government takes as its dividend. A Roth IRA, by contrast, is a personal private garden, where every cent of appreciation belongs entirely to you. If the long-term annualized return is 10% but you must pay about forty percent income tax on withdrawal, then the real after-tax return shrinks sharply to around 6%.

In addition, the act of collecting dividends generates a hidden drain. Data show that dividend tax and NHI premiums cause a compounding loss of about 0.78% a year. This number looks tiny, but stretched over 30 years it shrinks the final assets by more than 20%. Another landmine is the annuity, which pushes up the taxable-income bracket and makes it hard to execute a Roth conversion effectively. The true nature of compounding is to eliminate every unnecessary tax friction.

A Basic Explanation of PFIC

For those with US tax status (US Persons), many non-US-registered funds may fall under the PFIC (Passive Foreign Investment Company) rules. If you hold Taiwan ETFs (such as 00662, 0050), the common risks are:

If a US-person investor already holds Taiwan ETFs by mistake, it is advisable to consult a CPA with cross-border experience and evaluate the three paths of a QEF election, a Mark-to-Market election, or divesting. (Exemption threshold: if the total market value of all PFICs held at year-end is below US$25,000, or US$50,000 for a married couple filing jointly, and there is no excess distribution or disposition gain that year, you can usually be exempt from filing Form 8621.)

FBAR and FATCA Reporting Obligations

If you have US tax status and hold overseas financial accounts, you generally need to assess the FBAR (Foreign Bank Account Report) and FATCA (Foreign Account Tax Compliance Act) reporting requirements. Whether a threshold is met, how to report, and which accounts must be included should be handled according to that year’s rules and professional advice.

For US tax residents, compliant reporting of overseas accounts is not optional. The IRS has extremely destructive penalties for unreported overseas accounts: for a willful failure to report, the civil penalty can reach “the greater of 50% of the account balance or the statutory amount,” and it can be assessed year after year. Take a US$1.5 million Taiwan account (about NT$50 million) as an example: once it is deemed a willful failure to report, the penalty could start in the hundreds of thousands of US dollars, and this is only the civil penalty, not counting criminal liability. Overseas assets must not only be allocated well; they must also be reported in compliance.

The Debt Deduction and Exemption of the US Estate Tax

The US estate-tax system differs greatly from Taiwan’s; the applicable thresholds, the calculation method, and the scope of assets are all different. In arranging succession, cross-border families cannot design based on Taiwan’s gift and estate logic alone.

For US citizens and green-card holders (US Persons), the estate tax has a key computational mechanism of “deducting legal debts from the net estate, then comparing against the exemption,” which lets the Buy, Borrow, Die strategy exert its ultimate effect:

If your funds are large enough and your pledge capacity is high enough, for example a borrowable line of US$2 million, which should be enough for the expenses you mention, then keep spending with cheaply borrowed money and let your own funds keep earning a higher return. Never sell stock, never pay tax. Then when your hundred years come, assets offset debts, and only then do you have the net estate. If the net estate is within the exemption of US$15 million, it is also free of estate tax. This way, you pay no tax your whole life.

The core of this logic is that the net-estate formula for a US citizen or green-card holder is “total assets minus the pledge debt accumulated during life equals the net estate.” If this net figure falls within the exemption at that time (in 2025, OBBBA repealed the originally scheduled 2026 sunset and permanently raised the federal estate/gift-tax exemption to about US$15 million per person, indexed to inflation from 2027), then both the pre-death and post-death tax burden can be pressed to the extreme minimum. During life, using borrowed money to cover living expenses does not trigger income tax, and at death, debt offsetting assets presses the net estate down within the exemption threshold.

An especially serious contrasting warning: a Taiwan tax resident who is an NRA (non-resident alien) under US tax law has an exemption of only US$60,000 for US-situated assets, with the excess taxed at 40% estate tax directly. The gap in the exemption between the two statuses is “US$60,000 versus US$15 million,” a huge difference of up to 250-fold. If an NRA reader mistakenly applies the US-citizen logic of deducting debt from the estate to himself, he will face catastrophic tax consequences at succession.

Tax status Estate-tax exemption Rate above the exemption Buy, Borrow, Die endgame applies
US citizen / green-card holder About US$15 million (from 2026, made permanent by OBBBA) 40% Yes (after debt offset, falling within the exemption can mean zero tax)
Taiwan tax resident (NRA under US tax law) Only US$60,000 for US-situated assets 40% No (the exemption is too low; separate planning is needed at succession)

US-person readers can boldly use the Buy, Borrow, Die strategy: during life, cover living expenses with pledged borrowing (which does not trigger income tax), let assets keep compounding, and at death let the pledge debt offset assets to drop below the exemption threshold, achieving a succession endgame with an extremely low tax burden.

The Priority Pecking Order of Tax-Advantaged Accounts in the Accumulation Phase

Exit and succession tax matters are important, but for a US-person wage-earner, the order of contributing to tax-advantaged accounts in the accumulation phase equally determines how much fat compounding can churn out. The tax-advantaged accounts a US household can use fall roughly into four categories: the pre-tax 401(k)/403(b), the HSA (Health Savings Account), the Roth IRA/Roth 401(k), and the 529 education savings account. These four have a clear priority pecking order, and getting the order wrong means handing money to the IRS every year.

The priority rules split into two scenarios:

The 529 education savings account ranks last, not because it is worthless, but because its tax-free scope is limited to qualified education expenses, its fund choices are restricted and often carry extra management fees; and if the child ultimately does not need this education money, withdrawals are taxed as income plus a 10% penalty. When resources are limited, consider the 529 only after the first three categories are filled.

The essence of this pecking order is “grab the free money first, then the triple-tax-free, then the partially tax-free, and only last the conditionally tax-free.” Any decision that disrupts this order, such as funding the 529 before the HSA, or ignoring the employer match to fund a Roth first, actively hands your own several thousand US dollars a year of tax benefit to the IRS.

▲ Figure 19-2 The priority pecking order of tax-advantaged accounts for US persons in the accumulation phase, where you grab the free money first, then the triple-tax-free

This chapter is general informational explanation, not tax or legal advice. The RMD ages, federal tax brackets (top of 37%), and PFIC rules listed here are compiled from the IRS rules in effect in 2026 (RMD per Pub 590-B and SECURE 2.0, tax brackets per Rev. Proc. 2025-32, PFIC per IRC §1291 to 1298 and Form 8621). Tax law is adjusted year by year, and actual filing is governed by the latest IRS announcements and CPA advice. For specific tax decisions, please consult a US tax advisor holding a CPA license. Before executing a Roth conversion, PFIC handling, cross-border inheritance, or other specific operations, the recommended process is:

  1. First confirm whether you yourself have US tax status (citizen, green-card holder, tax resident).
  2. Prepare an account inventory and asset classification, including Taiwan brokerages, overseas brokerages, and bank accounts.
  3. Consult a US tax CPA with cross-border experience on PFIC, FBAR, FATCA, and estate planning.
  4. After obtaining written advice, return to adjust the usable version of this book’s allocation strategy.

Asset allocation is not merely about choosing high-return targets; it is also a long-term game against the tax system. Only by recognizing early the latent threat of RMDs, flexibly deploying Roth conversions at market lows and low-tax-rate periods, completing FBAR/FATCA and other filings in compliance if holding overseas assets, and making good use of the federal estate-tax exemption, legal debt deductions, and complete asset-succession planning can a US-person investor effectively lock in the fruits of compounding. True financial freedom lies not only in how much money you made in the market, but in how much of your assets you can ultimately, legally and completely, preserve to pass on to the next generation.