IRC §1202 can exclude gain on qualified small business stock from federal income tax: for stock issued after July 4, 2025, 50% after 3 years, 75% after 4 and 100% after 5, capped at the greater of $15M or 10× basis; older stock needs 5 years, capped at the greater of $10M or 10× basis. Federal only: California taxes the full gain.
Send me the sale price and rough basis. Within one business day I'll email you the actual number and the Seller's Guide to §453. If it doesn't fit your deal, I'll tell you that plainly.
No retainer · no obligation. Hans Goldstein, a licensed insurance agent (CA Insurance License #4273294), will contact you and may discuss insurance products, including annuities.
Go deeper: excluding gain on qualified small business stock under Sections 1202 and 1045 on Big Sale Tax.
IRC §1202, the Qualified Small Business Stock (QSBS) exclusion, lets a qualifying founder exclude up to $10 million OR 10× their basis (whichever is greater) of capital gain on the sale of C-corp founder stock acquired on or before July 4, 2025 from federal income tax after a 5+ year hold. Codified since 1993, expanded to 100% exclusion in 2010.
2025 update (P.L. 119-21, signed July 4, 2025): for stock acquired after July 4, 2025, the per-issuer cap rises to $15 million (indexed for inflation after 2026), the exclusion phases in at 50% after 3 years, 75% after 4 years and 100% after 5 years, and the company gross-assets limit rises to $75M. Stock acquired on or before July 4, 2025 keeps the old rules: $10M cap, 5-year hold, $50M limit.
For a California founder selling a successful startup exit, this can remove millions of gain from the federal return, and it’s a statutory exclusion in the Internal Revenue Code that doesn’t require any structure, trust, or annuity.
The exclusion limit is the GREATER of:
For a founder who got 1M shares at $0.0001 basis ($100 total cost), the 10× cap = $1,000. So the dollar cap controls: for older stock, $10M of gain is excluded and normal capital-gains tax applies above that; for stock acquired after July 4, 2025, the cap is $15M.
| Item | Amount |
|---|---|
| Sale of founder stock | $15,000,000 |
| Cost basis (original purchase) | $100 |
| Capital gain | $14,999,900 |
| §1202 exclusion (federal, capped at $10M) | −$10,000,000 |
| Remaining taxable gain | $4,999,900 |
| Federal tax on remaining (20% + NIIT 3.8%) | −$1,189,976 |
| California state tax (~13.3% on FULL $15M gain, CA does NOT conform to §1202) | −$1,994,987 |
| Net to founder | $11,815,037 |
In this example, the federal §1202 exclusion removes about $2.38M of federal tax (the federal tax that would otherwise apply to the first $10M). California still taxes the full gain at ordinary rates. California does NOT conform to §1202 for individual sellers.
Under the new rules, the same $15M gain on stock acquired after July 4, 2025 could be fully excluded federally after a 5-year hold (the earliest such sales are in July 2030). The California tax would still apply.
California, Pennsylvania, Mississippi and Alabama do not conform to the federal §1202 exclusion. A California founder still owes CA marginal income tax on the FULL gain, even the portion excluded on the federal return.
For a $15M California exit, that means $1.99M in CA tax even with the full $10M federal exclusion. This is where stacking §1202 with the SIS makes sense: it spreads the California portion across multiple years.
Most §1202-qualifying founders can:
For a founder with $15M of qualified gain who has no immediate cash need, one structure to model is: claim the $10M §1202 exclusion + structure the remaining $5M as a 20-year SIS + a ~$1M cash carve-out for liquidity, which in this illustration comes to roughly $13M net (vs ~$11.8M from a straight cash sale at California rates). Your figures depend on your income, state and the payment terms.
If you didn’t hold the QSBS for the period §1202 requires (5 years for stock acquired on or before July 4, 2025; at least 3 years for a partial exclusion on newer stock), you can use IRC §1045 to roll over the gain into REPLACEMENT QSBS within 60 days of sale. The new QSBS inherits your holding period from the old. After 5 total years (counting both the old and new holding periods), you can sell with the §1202 exclusion.
Common use case: company gets acquired at year 4. Roll the gain into a new QSBS investment, hold for 1+ more year, sell with the full exclusion.
If your QSBS-eligible startup FAILS (worth $0 at exit), §1244 lets you claim up to $50K single / $100K MFJ as an ORDINARY LOSS (rather than capital loss limited to $3K/yr). Combine with regular capital-loss treatment for the rest. It is the downside counterpart to §1202’s upside.
If you’re selling a C-corp position you’ve held long enough (5+ years for older stock; 3+ years for a partial exclusion on stock acquired after July 4, 2025) and the company was under the gross-assets limit when you got your stock, you may qualify to exclude up to $10M federally, or $15M for newer stock. For California-state-tax planning on the residual, an SIS structure spreads the bite across years.
Run the SIS calculator on your exit 213-414-2808
A plain-English guide for sellers on how a structured installment sale defers the tax when you sell a business, practice, or property. It covers the math, the alternatives, and how to tell if your deal fits.
Leave your details and the PDF downloads right away. Within one business day Hans will email a preliminary read on which structure fits your deal. No retainer. On a funded structure, the insurer pays a one-time commission of about 4% of the amount structured to the brokerage firm that places it (Hans’s share is about 2.4%; no trail). It is built into the annuity pricing, not a separate fee.
📞 Hans Goldstein · 213-414-2808 · CA Insurance License #4273294 · Independent §453 specialist · Goldstein & Co. LLC
Hans Goldstein, a licensed insurance agent (CA Insurance License #4273294), will contact you and may discuss insurance products, including annuities.