give the shares, not what's left after the tax

There is a way to be organized about generosity that quietly shrinks the gift by about a fifth. You sell the shares, you set the money aside, you write the check — and the tax on that sale came out of the charity's side of the ledger, not yours.

You can donate stock directly to a qualifying charity or donor-advised fund instead of selling it first. If you have held the shares more than a year, the transfer generally avoids capital-gains tax on the appreciation and lets you deduct fair market value, so the recipient gets the whole position rather than whatever survived the sale.

This is not tax, legal, or investment advice. Limits, floors, and rates change from year to year, the figures below are illustrations, and your own advisor plus the current Internal Revenue Code govern what actually happens on your return.

Who this is for: someone who already owns shares they can transfer — vested and delivered stock, exercised options, a long-held public lot. Unvested RSUs and unexercised options generally cannot be given. Newly vested RSUs often carry a basis near the vest-date price, so they may not be the low-basis gift this post is about.

the order of operations is the whole trick

Two paths, same intention, different arithmetic.

Run one illustration. Say you hold $100,000 of stock with a $10,000 cost basis, and assume the top federal long-term rate plus the net investment income tax — 23.8% — with state tax set aside.

Sell first and the $90,000 gain generates roughly $21,420 of federal tax, leaving $78,580 to donate — and a deduction on $78,580, because that is the size of the gift you made. Transfer the shares and the charity books $100,000, your deduction is generally $100,000, and the gain is never realized by anyone who owes tax on it. The $21,420 gap is not a saving you found. It is a bill you volunteered to pay on the charity's behalf.

That is the loss frame, and it is the honest one: the money is already gone by the time most people ask the question. Sequence is not a rounding error on a concentrated, low-basis position.

four things decide what the gift is actually worth

1. Holding period. More than a year, and you are generally deducting market value. A year or less, and the deduction is generally capped at your cost basis — which on a position that just ran up is a fraction of what it looks like on your screen.
2. Publicly traded or not. Listed shares transfer electronically and need no appraisal. Private company stock, restricted stock, and LLC or partnership interests need a qualified appraisal, and many sponsors will not accept them at all.
3. Which lots. Give the lowest-basis shares. Keep the high-basis ones for the sale you were going to make anyway. Specify the lots in writing before the transfer, not after.
4. Who receives it. The recipient has to be a qualifying charity and it has to be operationally able to take the asset. Plenty of excellent land trusts and watershed groups cannot process a private-stock transfer. That constraint, not the tax code, is what pushes most people toward a donor-advised fund sponsor.

a lockup is not a sale

This is where confident wrong answers do real damage, in both directions.

A lockup usually restricts disposing of the shares — sale, pledge, and often transfer. Many forms carve out bona fide gifts, often with the recipient bound by the same restriction. Whether yours does is in the document, and whether it is permitted depends entirely on the document you signed. Some agreements carve out gifts to charity. Some allow them with company or underwriter consent. Some prohibit any transfer, and some let the shares move while keeping the restriction attached, so the charity holds locked stock until the window opens and only then can sell. Private company shares usually carry their own layer: transfer approval, a right of first refusal, and a plan administrator who has seen this request before.

So: read your agreement, then ask your counsel and the company — in that order. Do not assume you are blocked. Do not assume you are clear. And do not take the sequencing lesson above as permission to move restricted stock; the whole advantage evaporates if the transfer was not allowed in the first place.

why the room is already saying "DAF"

Some context on why this question is suddenly everywhere, offered as illustration rather than instruction.

Reporting and advisor chatter around Anthropic describe an employee program that matches equity donated to charity: historically around 3:1 up to half of an employee's equity, with newer hires described at 1:1 up to a quarter. Dario Amodei wrote in January 2026 that employees had "pledged to donate company shares worth billions… donations that the company has committed to matching." Treat the ratios as rumor-and-advisor grade — they come from company essays, wiki-style trackers, and the people who advise those employees, not from a benefits document anyone has published. This is not a walkthrough of anyone's HR portal, and we are not telling you what your plan allows.

The narrow point is this: if a match is keyed to donated equity — as the Anthropic program is described by advisors and by Dario Amodei's January 2026 public line — the choice between giving shares and giving cash can become the largest financial decision of someone's year. And the default landing place for that decision is a donor-advised fund. US donor-advised funds held about $327.9 billion in fiscal 2024 across roughly 3.6 million accounts. Two-thirds of contributions at the big sponsors are already non-cash, because this is exactly what the rails were built for.

the shares clear. the watershed doesn't notice yet

Here is the part the mechanics section cannot tell you. A donor-advised fund is a parking lot. A living system is a place.

The moment the shares transfer, the tax event is finished — deduction taken, gain avoided, receipt filed. The impact event has not started. There is no federal minimum payout on a donor-advised fund, so the gap between those two moments can be a week or a decade, and nothing in the paperwork will tell you which one you chose. That is the actual trap in this whole sequence, and it is a much bigger number than the $21,420.

Watersheds, forests, soils, species, and the water cycle exist whether or not anyone funds them. They are not one cause area among several. They are the substrate every other cause runs on: the global-health program, the food system, the data center, and the endowment that pays for all three. Underfunding the living world is not neutrality.

So the second question, after the sequencing one, is what the gift ends up holding. A grant can buy a year of an organization's general operating budget — that is often the right gift. Land trusts have attached gifts to named parcels for decades. The extra question is whether you can still see the place afterward. Name a place, not a theme. A live example we already write is inland wetlands — a named living stock, not a cause area. Another is the Okefenokee.

That is the work here: ensurance funds and protects named natural assets before loss, rather than compensating after it. In plain terms, a certificate, if one is recorded, is a record of what got funded at one named place — no land title, no promised return. If the dollars come from a donor-advised fund, the grant goes to a qualifying public charity. You do not get a security, a claim, or a tradeable position back. A certificate, if one is recorded, is a record of what the grant funded — held by the recipient — not a benefit to you. Buying a certificate with taxable money is a different act, and it is not a charitable contribution. When we put a price on a place's condition, the price is a bridge that makes the bill legible to capital. It is never a claim about what the place is worth.

To be plain about where we are: there is no "grant from your DAF" button here to click. The right first move is a conversation, and depending on the place, the receiving charity may be a land trust or fiscal sponsor rather than us. Say what you want the money to hold and we will tell you whether a live door exists — see /specific for what is actually on the grid today.

this post is stock. land is a different door

If the appreciated asset is real property rather than shares, almost everything above changes: the appraisal requirement, the AGI ceiling, the vehicles, and whether you can keep using the land after you give it. That has its own cluster, and it is more thorough than a paragraph here would be:

• land donation: the complete guide to giving land for conservation — recipients, timelines, what a land trust will and won't take
• the tax play: how donating land can pay you back — the deduction, the capital-gains break, conservation easements, and the vehicles that pay you income
• how to fund a conservation group — if you already know the organization and just want the money to land well

frequently asked questions

can I donate stock to charity?

Yes. Most public charities, community foundations, and donor-advised fund sponsors accept publicly traded shares by electronic transfer, and the standard result for shares held more than a year is a fair-market-value deduction with no capital-gains tax to you.

Private company stock, restricted stock, and pre-IPO equity are a different conversation. Those need a qualified appraisal, they need the company's transfer rules to permit the gift, and they need a recipient willing and able to hold an illiquid asset. Confirm all three before you promise anyone a number.

why donate appreciated shares instead of cash?

Because the appreciation is never taxed, so the same intention produces a larger gift and you keep the cash you would have used to pay the tax. The stock is the tax-inefficient dollar in your portfolio; cash is the efficient one. Give the inefficient dollar.

There is one clean exception. If the position sits at a loss, the logic inverts: selling to realize the loss and donating the cash generally beats gifting a depreciated share, because a gift throws the loss away.

can I donate shares during an IPO lockup?

Sometimes, and the only reliable answer is in your own documents. A lockup restricts sale, not necessarily transfer — some agreements permit charitable gifts outright, some require company or underwriter consent, some forbid transfer entirely, and some allow the shares to move with the restriction still attached, so the charity cannot sell until the window opens.

Read the lockup, then ask your counsel and the company before you initiate anything. And notice the timing question underneath it: for many people, the largest gift decision arrives at the exact moment their shares are least movable, which is precisely why it is worth deciding what the money should hold before the window opens.

next steps

The sequencing decision is short and mostly arithmetic: give the shares, pick the lowest-basis lots, check what your agreement permits, keep the cash. The one that takes real thought is the one nobody bills you for — what the gift ends up holding.

how to grant from a DAF to a place →

talk to someone about where the money should land →