BTHE BARATELLI INSTITUTE · Mentoring at Scale
FOR DONORS HOLDING APPRECIATED SECURITIES

Cash is the wrong way to give. Stock is almost always the right one.

Donating long-term appreciated stock to charity unlocks three benefits at once: a fair-market-value deduction, zero capital gains tax on the appreciation, and a clean rebalancing event for concentrated positions. Charity nets the same amount either way. Donor keeps 20-30% more of the value. This tool runs the side-by-side.

FMV
Full deduction
0% Gains
On the appreciation
+NIIT
3.8% avoided
Rebalance
Concentration cured
YOUR GIFT
1
The stock
2
Donor profile
3
Path comparison
STAGE 1 OF 3

The stock

FMV, cost basis, and holding period are the three things that determine whether this is a good gift to make in stock — or whether you should sell first and gift cash (almost never the right call when long-term gain is large).

Today's market value of the lot you intend to donate. Use the high-low average on the gift date for the formal acknowledgment.
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What you paid for the shares. For tax-lot purposes, donors typically gift the lowest-basis lots first to maximize the avoided-gain benefit.
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Must be more than one year and one day for long-term treatment. Short-term gifts get deductible-at-basis-only treatment — usually a meaningful haircut.
Publicly-traded securities are the cleanest case. Non-publicly-traded stock to a private foundation gets basis-only treatment with narrow exceptions; flagged in results.
Why charity gets the same either way. Charity is a tax-exempt entity. When charity receives stock and sells it, charity owes zero capital gains. So whether you give $250K cash or $250K of stock, charity nets $250K. The donor's outcome is what changes — donor either pays cap gains on the way to giving cash, or doesn't.
STAGE 2 OF 3

Donor profile

Federal capital-gains rate, state rate, and NIIT applicability — these set the size of the tax that Path A creates and Path B avoids.

Drives marginal ordinary rate, long-term cap-gains rate tier, and NIIT applicability.
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Public charities get 30% AGI cap on appreciated property; private non-operating foundations get 20% (and basis-only for non-publicly-traded stock).
No state income tax in FL/TX/WA/NV/SD/TN/WY. High-state donors get even bigger Path-A vs. Path-B differential.
Auto-set from AGI + filing (0% / 15% / 20%). Override if doing AMT / QBI / Section 1202 modeling.
Net Investment Income Tax: 3.8% on investment income for AGI above $200K single / $250K MFJ. Adds to the cap-gains hit on Path A.
Federal ordinary + state, used to value the charitable deduction. Auto-computed from AGI + filing + state.
%
Used to confirm the donor itemizes. If charitable + other don't beat the standard deduction, the deduction benefit is reduced or zero.
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STAGE 3 OF 3

Path comparison

Side-by-side: sell-then-donate (the wrong way) vs. donate-direct (the right way). Charity nets the same in both. Donor doesn't.

HERE, TRY THESE. THEY MAY HELP.

No sign-up. No nurture sequence. Just the work.

The deeper material lives in the two companion guides. Both are free. Both are written for practitioners — the donors who deploy concentrated wealth into mission, and the advisors who structure it.

Read the Family Office Guide → Read Estate Planning Decoded → All free tools
Practitioner reference. This is not tax, legal, or financial advice. Consult your CPA or estate attorney for your specific situation. Tax rates, AGI limits, RMD ages, and IRMAA thresholds change annually — verify against current IRS publications before relying on any number. Long-term capital gains brackets (0/15/20), NIIT thresholds ($200K single / $250K MFJ), and 2026 standard deduction figures are illustrative. State rates are top-marginal approximations. Closely-held / restricted stock requires qualified appraisal under IRS Pub. 561 and the basis-only rule for private-foundation gifts has narrow exceptions; engage a qualified appraiser and a CPA before transfer.
WANT THE METHODOLOGY BEHIND THIS TOOL?
Read more in the Family Office Reference.
The tool gives you the answer. The guide gives you the argument — the case law, the worked examples, the negotiation playbook, the cross-check tables, the exception cases.
The methodology behind this calculator is in Estate Planning Decoded · charitable giving of the reference guide.
Read more in the Family Office Reference → Browse all 22 guides
Educational references and tools — not legal, tax, accounting, or investment advice, and not a recommendation to buy or sell any security. Consult a qualified professional about your specific situation. © 2026 The Baratelli Institute.