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Selling company stock or one big position: spread it, shelter it, or give it

A concentrated position is the one big sale where installment sales and 1031s do not apply. The tools are different: which year, which lot, which account, and whether charity is part of the picture.

One-page cheat sheet for this exact situation, plus a live Zoom walkthrough Saturday, October 10, 2026 at 10:30 AM PT / 1:30 PM ET. Nothing is sold.

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The number

What this sale costs if nothing is planned

$1,500,000 of employer stock with $150,000 basis, married couple, California, sold in one year in 2026

Layer	Rate (source below)	Amount
Long-term capital gain ($1.35M)	20% above $613,700	about $260,000
Net investment income tax	3.8%	about $51,000
California	9.3% to 12.3%	about $150,000
Total		about $461,000 (34% of gain)

Rounded, illustrative, assumes no other income in the year of sale. See Sources and review at the bottom of the page.

The options, in plain language

Five ways this tax gets paid, spread or shrunk

Sell across years, filling brackets. Sell enough each year to stay under the 20% line ($613,700 MFJ taxable) and, where possible, the 3.8% NIIT line. The 0% bracket ($98,900 MFJ) is real in a low-income year.
QSBS (Section 1202). Original-issue C corp stock held 5 years: up to $15M of gain federally tax free (2025 law). Confirm eligibility before selling a share.
Exchange fund. Contribute the position to a diversified partnership; no sale, no tax, diversified after 7 years. Accredited investors, high minimums, illiquid.
Charitable remainder trust or donor-advised fund. Give appreciated shares, not cash. A CRT sells untaxed and pays income for life; a DAF gives a deduction at full value with no gain.
Gift and step-up. Shares given to family in lower brackets carry your basis; shares held to death get a step-up. Sometimes the answer is to sell a little and hold the rest.

Who this is written for: people who have owned the asset for years, often decades, and are selling once, usually around retirement. If you are buying and selling frequently, different rules (dealer status, ordinary income) apply and this page is not for you.

Six questions to bring to your CPA

Lot-by-lot basis and holding periods?
Is any of it QSBS, and what documents prove it?
How much can I sell this year and stay under 20% and NIIT?
Which shares should go to charity versus be sold?
Does an exchange fund make sense at my size and liquidity needs?
RSU / ISO / ESPP pieces: which are ordinary income?

The deadlines that decide it

QSBS: 5-year holding from issuance.
Charitable gifts of stock: delivered by December 31.
Estimated tax in the quarter of a large sale.
10b5-1 plans for insiders: set up before the window closes.

Common questions

Straight answers

Can I do an installment sale of publicly traded stock?

No. Publicly traded securities are excluded from Section 453.

What is the 0% capital gains bracket?

Married couples with taxable income under $98,900 (2026) pay 0% federal on long-term gains. A retirement gap year can be a 0% year.

Is an exchange fund a sale?

No, it is a contribution to a partnership. Tax is deferred until you sell the fund units.

What about an inherited position?

It got a step-up at death; the gain before that date is gone. Sell or hold on the merits, not the tax.

Audit trail

Sources and review

Reviewed for the Retirement Literacy Foundation, a 501(c)(3) education nonprofit. Prepared by Hans Goldstein, retirement educator; IRS Special Enrollment Examination Parts 1, 2 and 3 passed, enrollment pending; California licensed insurance professional #4273294. Informational only. Not tax, legal or investment advice. Every figure below cites its source so your CPA or attorney can check it.

Capital gains rates and brackets 2026: IRS Rev. Proc. 2025-32 (2026 inflation adjustments); IRC 1(h)
Net investment income tax 3.8%: IRC 1411; thresholds $200,000 single / $250,000 MFJ, not indexed
Depreciation recapture 25% (unrecaptured 1250) and 1245: IRC 1(h)(6), IRC 1245, IRC 1250; IRS Pub. 544
Section 121 home-sale exclusion: IRC 121; IRS Pub. 523; surviving-spouse 2-year rule IRC 121(b)(4)
1031 exchange rules: IRC 1031 (real property only after TCJA 2017); Treas. Reg. 1.1031(k)-1 (45/180 days, QI); IRS Form 8824
Delaware Statutory Trust as 1031 property: IRS Rev. Rul. 2004-86
Installment sales: IRC 453; IRS Pub. 537; Form 6252; IRC 453A interest charge above $5,000,000; IRC 453(k) excludes publicly traded stock
Monetized installment sales: IRS Dirty Dozen (IR-2023-54 and later); proposed regs REG-109348-22
QSBS: IRC 1202 as amended by P.L. 119-21 (2025): $15M cap, tiered holding periods for stock issued after July 4, 2025
Charitable remainder trusts: IRC 664; Treas. Reg. 1.664; pre-arranged sale doctrine (Rev. Rul. 78-197)
Step-up in basis: IRC 1014; community property IRC 1014(b)(6)
Inherited IRA 10-year rule: IRC 401(a)(9)(H) (SECURE Act); Treas. Reg. 1.401(a)(9) final regs 2024
California treatment: Cal. Rev. & Tax. Code 17041 (rates), 18031 (1031 conformity), FTB Form 3840 (out-of-state exchange tracking); Prop 19 (Cal. Const. art. XIII A, sec. 2.1)
Purchase price allocation: IRC 1060; IRS Form 8594

Figures are 2026 federal amounts and 2025 California rates unless stated. Examples are illustrative, rounded, and assume no other income; your numbers will differ. Last reviewed September 21, 2026.

Selling company stock or one big position: spread it, shelter it, or give it

What this sale costs if nothing is planned

Five ways this tax gets paid, spread or shrunk

Six questions to bring to your CPA

The deadlines that decide it

Straight answers

Can I do an installment sale of publicly traded stock?

What is the 0% capital gains bracket?

Is an exchange fund a sale?

What about an inherited position?

Sources and review

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