Nvidia’s CEO resigned on Nov. 12, and the stock had already lost about 30% over the past month. For clients with a large position in a single stock, whether it’s Nvidia, company stock from their employer or an early winner they never sold, it’s a reminder that one headline can erase years of gains.
Most of those clients believe they’re stuck. Selling means a huge capital gains tax bill, so they hold and hope. They’re not stuck. They just haven’t used the tools that work best before Dec. 31.
The most powerful one is giving. Donating shares held more than a year to a donor-advised fund removes the gain entirely and creates a deduction for the shares’ full market value, generally up to 30% of income for appreciated stock. New rules this year make that strategy even more useful: itemizers can now deduct only charitable gifts above 0.5% of their income, which rewards “bunching” several years of giving into a single year. A client who already gives every year can fund the next few years of giving with their most appreciated shares and claim the deduction now.
Three strategies are worth comparing: giving the lowest-cost shares to a donor-advised fund, selling in stages across two tax years while offsetting gains with harvested losses, and protecting the position with options while diversifying over time. Most clients need a combination, and the right mix depends on their bracket, their giving, their age and how much of their wealth the stock represents.
Rather than walk through generic pros and cons here, we built a prompt that builds the plan for you. Describe your client and their position in one sentence, and it returns a one-page brief: how much to give, sell and keep, the estimated tax savings, which ETFs to use for the proceeds, what to watch out for and language you can use with the client.
Copy this prompt
My client: [Describe the client and the position in a sentence, e.g., "64, married, still working with $250K income, $2.1M portfolio with $700K in Nvidia bought years ago for about $50K, gives about $15K a year to charity."]
Work from whatever I've given you. Where details are missing, make reasonable assumptions and keep going. Don't stop to ask me questions.
Context (as of Nov. 13, 2026):
- On Nov. 12, 2026, Nvidia CEO Jensen Huang resigned; the stock had fallen about 30% over the prior month. The broader lesson applies to any concentrated position: company stock, an early winner the client never sold or an inherited holding.
- Many clients believe they're stuck with concentrated positions because selling triggers a large capital gains tax bill.
- Long-term capital gains are taxed at 0%, 15% or 20%, plus the 3.8% net investment income tax above $250,000 of modified AGI (joint) or $200,000 (single).
- Giving appreciated stock held more than a year to a donor-advised fund or public charity avoids capital gains tax on the appreciation and creates a deduction for full market value, generally limited to 30% of AGI for appreciated property, with a five-year carryover for any excess.
- Starting in 2026, itemizers can deduct only charitable gifts above 0.5% of AGI, and for taxpayers in the 37% bracket, the deduction's value is capped at 35%. This makes "bunching" several years of giving into one year more valuable. The new deduction for non-itemizers covers cash gifts only and excludes donor-advised funds.
- Selling part of a position in December and part in January splits the gain across two tax years. Harvested losses elsewhere in the portfolio (such as bond funds that fell after the Nov. 10 jump in yields) can offset gains; watch wash-sale rules when replacing sold holdings.
- For older clients or those with large estates, holding some shares until death can be valuable because heirs generally receive a step-up in cost basis.
- Options strategies such as collars or protective puts can limit downside while a position is sold down over time; very tight collars can trigger constructive-sale rules, so they need careful structuring.
- Donor-advised fund platforms are busy in December and stock transfers can take weeks to settle, so gifts should start by early December.
Three strategies to compare:
1. Give it: donate the lowest-cost-basis shares to a donor-advised fund, bunching several years of the client's normal giving into 2026.
2. Sell it in stages: sell portions in December 2026 and January 2027 (and beyond if needed), offsetting gains with harvested losses where possible.
3. Protect it while diversifying: hedge the remaining position with protective puts or a collar while selling down over a longer period.
ETFs for the proceeds (choose ones that don't add to the client's existing concentration; for a tech position, avoid tech-heavy funds):
- RSP (Invesco S&P 500 Equal Weight ETF): expense ratio 0.20%, broad U.S. stocks without mega-cap concentration
- VTI (Vanguard Total Stock Market ETF): expense ratio 0.03%, broad U.S. market (includes large tech weightings)
- AVUV (Avantis U.S. Small Cap Value ETF): expense ratio 0.25%, diversifies away from large-cap tech
- VXUS (Vanguard Total International Stock ETF): expense ratio 0.05%, non-U.S. stocks
Write a one-page meeting brief that makes complete sense on its own to someone who hasn't seen this prompt. Never refer to strategies by number or mention "the list," "the context" or "the prompt." Use exactly this format, in under 300 words total:
**What happened:** Two sentences on the news and why it matters for this client's position.
**Best fit:** Describe the recommended strategy or combination in plain words and explain why it fits this client in two sentences.
**The plan:** Three short lines with estimated dollar amounts and timing: Give, Sell and Keep (use "none" where a step doesn't apply).
**The numbers (estimates):** One or two sentences with the estimated capital gains tax avoided, the value of any deduction and the tax owed on any sales.
**Where the proceeds go:** A short table of ETFs for the sale proceeds, with columns for ETF (ticker plus full fund name), role and one key data point.
**Watch out for:** No more than three one-line points specific to this client (deadlines, itemizing, losses to harvest, step-up considerations, hedging risks).
**What to say:** Two or three sentences I can say to the client in plain language.
End with one line listing any assumptions you made about the client, then a final line: "Tax and fund data as of Nov. 13, 2026; verify before acting."
Write in plain language an advisor can scan in 30 seconds. Round numbers and label them as estimates. No jargon without a short explanation, no predictions about the stock, no generic investing advice and no political commentary. This is not tax advice; flag where a CPA should confirm the numbers.
