On July 4, 2025, the One Big Beautiful Bill Act (“OBBBA” or “the Act”) became law and ushered in the most significant changes to the Qualified Small Business Stock (“QSBS”) regime in more than a decade. These changes—codified under Internal Revenue Code § 1202—apply only to stock acquired after July 4, 2025. Stock issued on or before that date remains subject to the pre-OBBBA rules. From both an estate planning and a corporate tax/M&A perspective, the legislation creates new opportunities and new traps, all of which hinge on careful timing, documentation, and structuring.
One Big Beautiful Bill Act: Three Key QSBS Changes
The OBBBA modifies QSBS in three central ways. First, it introduces a tiered gain-exclusion system based on holding period. For QSBS acquired after July 4, 2025, a taxpayer can exclude 50% of the gain if the stock is held at least three years, 75% of the gain if held at least four years, and the full 100% of gain if held for at least five years. This partial-exclusion regime allows for earlier liquidity events while still preserving significant tax benefits. Second, there is an increase in the per-taxpayer, per-issuer exclusion cap for post-Act QSBS, from $10 million to $15 million (inflation-adjusted starting in 2027) or 10 times the taxpayer’s basis in the stock, whichever is greater. Third, the Act expands the “qualified small business” size threshold, raising the aggregate gross asset limit from $50 million to $75 million (also with inflation adjustments beginning in 2027). This change allows more growth-stage companies to qualify and remain eligible longer.
While these headline reforms are taxpayer-friendly, the Act’s transition rules are critical. QSBS acquired on or before July 4, 2025 will be subject to the pre-OBBBA rules, 100% exclusion after five years and capped at the greater of $10 million or 10 times basis. The acquisition date remains central: it is determined on a lot-by-lot basis, and holding periods generally tack in carryover transactions such as gifts and certain reorganizations. Attempting to “refresh” pre-Act QSBS into post-Act QSBS through an exchange will not succeed under the anti-reset rules. Furthermore, for sales before the five-year mark, the exclusion cap is scaled proportionally to the exclusion percentage—so a 50% exclusion at year three comes with a $7.5 million cap, and a 75% exclusion at year four carries an $11.25 million cap.
What the Changes Mean for Estate Planning
From an estate planning standpoint, the OBBBA enhancements magnify the longstanding benefits of QSBS “stacking.” Because the exclusion applies on a per-taxpayer, per-issuer basis, creating multiple taxpayers—most often through gifts to non-grantor trusts or to individual family members—can multiply the total amount of gain shielded from federal income tax. Gifts and bequests preserve QSBS character and tack the donor’s holding period, provided the stock otherwise remains eligible. Grantor trusts (e.g. revocable trusts), however, do not create separate taxpayers for § 1202 purposes, so only non-grantor structures achieve stacking. With the larger $15 million cap and the ability to claim partial exclusions after three or four years, families may find it attractive to diversify earlier while still extracting substantial tax-free gains. The expanded $75 million asset threshold also means more venture-backed startups can qualify, giving founders more runway to implement gifting strategies before the issuer grows out of QSBS eligibility. As always, these techniques must be coordinated with valuation practices, state-level conformity rules, and the broader estate plan, especially in light of federal estate tax exemptions and state-level estate and inheritance taxes.
What the Changes Mean for Corporate Tax Work
From a corporate perspective, the reforms reshape capital-raising and exit strategies. The increased $75 million threshold allows issuers to raise additional equity before breaching the QSBS ceiling. However, the unchanged “significant redemption” rules—triggered by certain buybacks within prescribed windows—can still taint new issuances, so companies should continue to include no-repurchase covenants and redemption blackout periods in financing documents. The original-issuance requirement also remains; secondary purchases do not confer QSBS status, and the holding period for restricted stock generally begins at vesting unless an 83(b) election is made.
The tiered holding periods invite more nuanced deal structuring. A founder with post-Act QSBS might, for example, negotiate a sale in year three or four with a price gross-up to account for the partially taxable portion, or roll over that taxable slice into replacement QSBS under § 1045 to defer the gain. In the M&A context, tax-free reorganizations can preserve QSBS attributes and tack holding periods, but practitioners must confirm that the reorganization qualifies and that the stock received meets the § 1202 requirements. Asset sales followed by liquidation, on the other hand, generally destroy QSBS eligibility for the seller. Deal diligence should now expressly address QSBS status, asset-test compliance, redemption history, and potential contamination of eligibility, with appropriate representations and warranties in the transaction documents.
Conclusion
In practice, the OBBBA’s QSBS reforms do not change the core principle: the regime remains a powerful incentive for investment in qualified C corporations, provided the eligibility rules are met and maintained. What has changed is the scope for planning. For estate planners, there is greater flexibility to achieve tax-efficient transfers and earlier diversification. For corporate and M&A practitioners, there are new timing and structuring options to maximize after-tax proceeds, alongside the same old pitfalls that can erase the benefit entirely. The message is the same for both audiences: track your dates, document your compliance, and coordinate your tax and legal strategies early.
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