The Situation

Tobi is 37, a research engineer who joined Anthropic in 2022, back when explaining where he worked took a full sentence. He lives in San Francisco with his wife, who is a pediatric nurse, and their son started kindergarten this month. He early-exercised his incentive stock options in 2023, wrote a check that felt reckless at the time, and has not thought about it much since.

He and his wife have given to the same two organizations for eleven years, a literacy nonprofit in Oakland and a fund that supports nursing scholarships. Roughly $20,000 a year, out of checking, by automatic transfer. They have never missed a year and they have never once looked at how they were doing it.

Then Anthropic ran a tender offer in April, at a valuation that made the number on Tobi's shares stop being abstract. He did not participate. He called us for a different reason: he wanted to know whether he should give some of the stock away, and whether it was too early.

The Gap We Found

It was not too early. It was very close to too late, and for a reason nobody had told him.

Tobi's CPA files an excellent return and had never seen a stock certificate. His 401(k) advisor manages a balanced portfolio and does not know what he holds outside of it. Neither of them had any reason to raise the point that governs this entire decision: the charitable window on private stock closes when the outcome stops being uncertain. Once a transaction is effectively locked in, the IRS can treat the gain as the donor's under the anticipatory assignment of income doctrine, and you end up giving away the asset while keeping the tax bill.

With a tender behind the company and press reports pointing at a possible listing, Tobi had months, not years. And the mechanics he needed, a qualified appraisal, company approval for the transfer, and a charitable sponsor willing to accept private shares at all, take most of those months to arrange.

What We Did

We started with the only question that could stop everything: would the company approve the transfer. Private shares carry transfer restrictions and rights of first refusal, and a charity cannot accept stock the issuer will not release. We got that answer first, in writing, before spending a dollar on anything else.

Then we sized the gift as a percentage rather than a number. Tobi kept trying to decide how many dollars to give, and every time the valuation moved he started over. We asked him instead what share of the position he was willing to give away, permanently, without knowing how the story ends. He said eight percent in about four seconds. He had never been able to answer the dollar version at all.

A qualified appraisal valued the donated tranche at $1,240,000 as of the transfer date, meaningfully below the headline tender valuation because a minority, non-controlling, illiquid common position appraises at a discount. His basis across those shares was $31,000. Had he sold them instead, the $1,209,000 gain would have carried roughly $448,000 in federal and California tax. Donating the shares directly means nobody pays it, ever.

We split the gift deliberately. A portion went straight to the two organizations he has supported for a decade, because Anthropic's charitable match program applies to direct gifts and Tobi had never opened the page describing it. The rest went into a donor-advised fund, so the giving can continue on his schedule for the next twenty years rather than arriving all at once and then stopping.

The deduction is where the plan gets patient. Appreciated property is deductible against 30% of adjusted gross income, and Tobi's 2026 AGI is his salary, about $412,000. So he deducts roughly $121,500 this year, after the new 0.5% floor takes the first $2,060, and the remaining $1,118,000 carries forward for up to five years. That carryforward is not a consolation prize. It is waiting for the year his remaining equity settles and his income goes somewhere it has never been.

The Result

• About $448,000 in federal and California capital gains tax permanently avoided, on a gift that cost him nothing out of pocket
• A $1,240,000 charitable deduction, roughly $121,500 usable in 2026 and about $1,118,000 carried forward into the year his income spikes
• His two organizations received more than double what his annual cash gifts had been delivering, once the employer match was applied
• The transfer was approved, appraised and completed with room to spare, rather than during a window when it would no longer have been possible
• He stopped restarting the decision every time the valuation moved. A percentage held still in a way a dollar figure never did.

Why This Worked

Nobody in Tobi's financial life was doing a bad job. His CPA was accurate, his advisor was prudent, and both were working inside their lane. But the decision he needed sat exactly between the lanes: it required reading a grant agreement, a tax return, a charitable intention and a news cycle at the same time, and no one was holding all four. Because Alphanso charges a flat fee and takes no percentage of assets, nothing about recommending that he give a piece of his largest position away costs us anything, which is precisely why he could trust the recommendation. If you hold pre-IPO equity and giving is somewhere in your plans, the timing matters more than the amount. Talk to an advisor.

This case study is a composite illustration based on real Alphanso client scenarios. Names and identifying details have been changed for privacy. Results are not guaranteed and will vary based on individual circumstances. All investing involves risk, including the possible loss of principal. Tax services are for educational purposes and do not constitute legal advice. Alphanso LLC is a registered investment adviser.