Tax strategy.
What every CPA does for wealthy clients.

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 IRAIndividual Retirement Account (IRA)A personal retirement savings account with tax advantages. Two main types: Traditional (tax now, pay later) and Roth (pay now, tax-free forever).Full definition 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 ConversionRoth conversionMoving money from a tax-deferred retirement account (where you'll owe tax later) into a Roth account (where everything grows and comes out tax-free). You pay regular income tax this year on the amount moved.Full definition Ladder. Model the low-income window between ending work and age 73 (RMDsRequired Minimum Distribution (RMD)The minimum amount the IRS requires you to withdraw annually from Traditional IRAs and 401ks starting at age 73 (rising to 75 in 2033). Calculated as account balance divided by your IRS life expectancy factor. Roth IRAs have no RMDs during the owner’s lifetime.). That is the single most valuable tax arbitragearbitrageProfiting from price differences in the same asset across different markets, often by buying low in one place and selling high in another. in the system.
• Already retired, pre-Social Security. Withdrawal Sequencingwithdrawal sequencingThe order in which retirement accounts are drawn down. Conventional textbook order is taxable, then Traditional, then Roth. The actual optimal order depends on Roth conversion opportunities, RMD pressure, IRMAA, and Social Security timing. 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 incomeprovisional incomeThe income figure used to determine how much of your Social Security benefit is taxable. Includes adjusted gross income, tax-exempt interest, and 50% of your Social Security benefit. Up to 85% of SS benefits can be taxable for higher earners. below the 85% cliff where possible.
• Bitcoin holder in any bucket. Tax-Loss Harvesting every bear marketbear marketA period when investment prices are falling, typically defined as a 20% or greater drop from recent highs.. Bitcoin in Roth if you have the contribution room. Plan large sales around state residency. See Bitcoin Taxes.

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 DAFDonor-Advised Fund (DAF)A charitable account where you contribute, take an immediate tax deduction, and direct gifts to charities over time.Full definition, 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 deductionstandard deductionA fixed dollar amount that reduces your taxable income without itemizing. Most people claim this instead of listing individual deductions.Full definition); people with highly appreciated assets (donating Bitcoin or stock avoids capital gainscapital gainsThe profit from selling an asset for more than you paid for it. Taxed differently depending on how long you held the asset. and gets a deduction at FMVFair Market Value (FMV)The price an asset would sell for between a willing buyer and seller with equal information.Full definition); 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.

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, IRMAAIncome-Related Monthly Adjustment Amount (IRMAA)A Medicare surcharge added to your monthly premium if your income exceeds certain thresholds.Full definition 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.

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