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.
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. Specific figures should be confirmed against current IRS publications before you act on them. 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.
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.
All tax guides
Every tax-related page on the site.
- IRS Publication 590-A and 590-B (IRAs) - irs.gov
- IRS Rev. Proc. 2025 inflation adjustments - irs.gov
- Kitces.com - Roth conversion and withdrawal sequencing research - kitces.com
- Bogleheads wiki - Tax-Efficient Fund Placement - bogleheads.org
- Social Security Administration benefit calculators - ssa.gov
Qualified vs non-qualified dividends, DRIP and the tax trap.
Advanced strategies: DAF and QOZ
Donor-Advised Fund (DAF)
A charitable-giving account that lets you take a tax deduction now and distribute to charities later at your own pace. Contribute assets (cash, stock, Bitcoin) to the DAF, receive a tax deduction immediately at fair market value, invest the funds inside the DAF tax-free, then grant to charities over time verify×DON'T TRUST, VERIFYClaim: DAFs allow immediate deduction at fair market value with deferred distribution to charities.Verify at: IRS Donor-Advised Funds page ↗DAF contributions are deductible at fair market value (subject to AGI limits), and distributions to qualified charities are required, but no minimum payout deadline applies at the donor level..
Who benefits: people bunching multiple years of charitable giving into one year (to clear the standard deduction); people with highly appreciated assets (donating Bitcoin or stock avoids capital gains and gets a deduction at FMV); high-income years where extra deduction is most valuable.
Qualified Opportunity Zones (QOZ)
Designated low-income census tracts where investments through a Qualified Opportunity Fund receive capital-gains deferral. Defer original capital gains until 2026 (or sale of the QOF investment). Hold the QOF investment for 10 years and the appreciation in the QOF itself becomes tax-free verify×DON'T TRUST, VERIFYClaim: QOZ 10-year hold eliminates tax on appreciation of the QOF investment.Verify at: IRS Opportunity Zones page ↗IRC Section 1400Z-2 governs the program. The original deferred gain is recognized in 2026; the 10-year exclusion applies to QOF appreciation..
Risks: illiquid (typical 10-year hold), development risk in the underlying project, complex legal structure. Who should consider: someone with a large capital gain (business sale, large Bitcoin sale) looking to defer and potentially eliminate gains. Consult an attorney; the structuring is not DIY.
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Last updated 2026-04-14. Not legal or tax advice. For anything material, hire a CPA.
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