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3 MIN READ

Tax strategy.
What every CPA does for wealthy clients.

Taxes are the single largest expense most Americans will ever pay. Legally minimizing them is not a loophole - it's what every CPA does for wealthy clients. This is that playbook, applied to a regular person's life, with a Bitcoin lens where it applies.

READING TIME: 4 MIN

THE SHORT VERSION

Five levers do most of the work: put the right asset in the right account (asset location), move pre-tax money to Roth in your low-income years (Roth conversions), sell losers to offset winners (tax-loss harvesting), time Social Security around your tax picture, and pull from accounts in the right order in retirement. Each one is a real pile of money. Stacking all five is career-changing.

Not a CPA. This is education, not tax advice. Rates, thresholds, and limits change every year. Anything marked [VERIFY] needs to be confirmed against the current IRS publications before you act on it. For material decisions, hire a CPA.

The five-lever playbook

Each card is its own deep-dive. Read them in order if you are starting from scratch. Jump to whichever matches your life stage if you are not.

LEVER 1
Same assets, different accounts, very different after-tax outcomes. Bonds in Traditional. Bitcoin and stocks in Roth. Index ETFs in taxable. The placement matters more than almost any fund pick.
LEVER 2
Move pre-tax money to Roth in low-income years. Pay tax now at 12% instead of 24% later. The classic early-retiree move. Bitcoin crashes create perfect conversion windows.
LEVER 3
Sell losers, offset winners, carry the rest forward. Bitcoin has no wash-sale rule (for now), which makes it the cleanest harvesting asset in the portfolio.
LEVER 4
When to claim (62, 67, 70) is a tax decision, not just a longevity bet. Roth income does not count toward the provisional-income formula that taxes your benefits.
LEVER 5
Which account first in retirement. The textbook answer (taxable, then Traditional, then Roth) is often wrong. Fill the 12% bracket every year you can.

Which applies to you

Tax strategy is not one-size-fits-all. Pick the lever that matches your situation first, then come back for the rest.

  • Starting out, first real job. Asset Location. Get Bitcoin and stocks in the Roth IRA from day one. That one decision compounds for 40 years.
  • Mid-career with a 401(k) piling up. Asset Location plus Tax-Loss Harvesting. Most of your savings are pre-tax. Build a Roth bucket alongside.
  • Retiring in the next 10 years. Roth Conversion Ladder. Model the low-income window between ending work and age 73 (RMDs). That is the single most valuable tax arbitrage in the system.
  • Already retired, pre-Social Security. Withdrawal Sequencing plus Roth conversions in the low-income gap. Fill the 12% bracket every year.
  • Already claiming Social Security. Social Security taxation plus Withdrawal Sequencing. Keep provisional income below the 85% cliff where possible.
  • Bitcoin holder in any bucket. Tax-Loss Harvesting every bear market. Bitcoin in Roth if you have the contribution room. Plan large sales around state residency. See Bitcoin Taxes.

A well-run tax strategy routinely saves a middle-class household six figures over a lifetime. A great one saves seven. It is the highest-leverage financial work most people never do, because their CPA is a form-filler and their advisor is an asset-allocator. Neither job is tax strategy.

A word on "not advice"

Everything on these pages is general education. Tax law is fact-specific. Two households with identical incomes can have completely different optimal moves based on state residency, filing status, pension situation, healthcare subsidies, IRMAA brackets, and a dozen other variables.

For anything material, hire a CPA. Not the one who files your 1040 in twenty minutes, a planning CPA. Expect to pay $500 to $3,000 for a tax projection. It pays for itself many times over when the strategy is right.

Sources & Citations
  1. IRS Publication 590-A and 590-B (IRAs) [VERIFY 2026] - irs.gov
  2. IRS Rev. Proc. 2025 inflation adjustments [VERIFY 2026 brackets] - irs.gov
  3. Kitces.com - Roth conversion and withdrawal sequencing research - kitces.com
  4. Bogleheads wiki - Tax-Efficient Fund Placement - bogleheads.org
  5. Social Security Administration benefit calculators - ssa.gov

Last updated 2026-04-14. Not legal or tax advice. For anything material, hire a CPA.

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