ARTICLE | July 25, 2025
Executive summary
The One Big Beautiful Bill Act (OBBBA), enacted on July 4, 2025, significantly expands the tax benefits available under section 1202 of the Internal Revenue Code, which governs qualified small business stock (QSBS). These enhancements aim to stimulate investment in small businesses by offering substantial capital gains exclusions to eligible shareholders.
The benefit of section 1202 has increased significantly since 2009–2010. Prior to 2009–2010, the benefit was relatively limited, and as such there is very little guidance on a number of issues where the law is unclear. This is both a benefit and risk to taxpayers, and currently provides taxpayers with a certain level of leeway in concluding on qualification.
Key opportunities
1. Tiered exclusion structure
Investors can now exclude:
- 50% of capital gains after three years (with the remaining gain taxed at 28% for a 14% rate and 50% exclusion from 3.8% Medicare tax);
- 75% after four years (with the remaining gain taxed at 28% for a 7% rate and 75% exclusion from 3.8% Medicare tax)
- 100% after five or more years
This tiered system rewards long-term investment while offering earlier liquidity options.
2. Retained pass-through exclusion
The exclusion can be passed through to investors in S corporations and partnerships if structured properly, so the maximum exclusion is often significantly higher than either the $15 million or 10 times the basis that the S corporation or partnership would receive at the entity level.
3. Broader eligibility
The gross asset threshold for qualifying businesses has increased from $50 million to $75 million, expanding access to QSBS treatment—especially for capital-intensive startups.
4. Higher exclusion caps
The lifetime gain exclusion cap has been raised to $15 million for stock acquired after the OBBBA’s enactment, with inflation adjustments beginning in 2027.
5. Strategic planning: QSB silos
Taxpayers are increasingly exploring so-called QSB silos to isolate qualifying business lines within larger pass-through structures. By housing eligible activities in separate C corporations, investors may unlock significant capital gains exclusions while maintaining operational synergies. Another term that could describe a QSB silo is a “Captive QSB.”
While “Captive QSB” may raise eyebrows due to its resemblance to micro-captive insurance structures, the intent here is to isolate qualifying business lines—not to create artificial tax shelters.
Example: QSB silo formation within a large partnership
Background
A partnership holding company, Holdings LP, operates a diverse portfolio of businesses valued at approximately $500 million, primarily through:
- Disregarded entities (e.g., single-member LLCs)
- Joint ventures structured as partnerships
- Direct ownership of assets
Transaction
Holdings LP acquires the assets of the target business for $70 million, which is below the $75 million gross asset threshold required for QSBS eligibility under section 1202.
QSB silo strategy
After acquisition, Holdings LP decides to incorporate the target business assets into a newly formed C corporation—let’s call it TargetCo Inc. This entity is structured to meet all QSBS requirements:
- Original issuance of stock
- Active business operations
- Gross assets below $75 million at the time of issuance (fair market value or basis depending upon facts and circumstances)
Assuming all requirements are met, stock in TargetCo Inc. may qualify as QSBS, offering potential capital gains exclusions to future shareholders.
Key consideration: stand-alone viability
The critical issue becomes whether TargetCo Inc. (the QSB silo) is truly stood up as an independent operating entity. Specifically:
- Can TargetCo Inc. operate on a stand-alone basis?
- Does it have the capacity to carry the debt it reports?
- Is it functionally independent from Holdings LP, or merely a shell?
If the QSB silo is overly dependent on Holdings LP for operations, financing, or management, the IRS may challenge its substance and deny QSBS treatment. This is especially true if the debt used to acquire the target business remains on TargetCo’s books but is serviced by Holdings LP or other affiliates. Other considerations include appropriate transfer pricing to maintain arm’s length transaction standards between the entities.
Takeaway
While the QSB SILO strategy can unlock significant tax benefits, it must be executed with care. The new entity should:
- Be operationally viable
- Maintain independent governance and financials
- Avoid artificial structuring that lacks economic substance
Substance matters: The IRS will look beyond form to determine whether the QSB SILO is a legitimate stand-alone business or a conduit for tax benefits.
Key risks
1. Aggressive structuring
Some taxpayers may attempt to qualify stock or manipulate entity structures in ways that stretch the intent of section 1202.
One example involves funding a company just under the $75 million gross asset threshold at incorporation, and then almost immediately borrowing funds and acquiring assets that push it well over the limit—all pursuant to a prearranged plan. While technically the gross asset test applies at the time of stock issuance, the IRS may view such pre-planned maneuvers as abusive, subject to step-transaction doctrine, substance over form, or even the section 269 anti-abuse provisions.
Other areas could include the treatment of QSB following stock held by a private equity fund that undergoes a fund continuation, qualification of the active business requirement through investments in certain pass-through entities, the treatment of certain SAFE (simple agreement for future equity) investments, convertible debt, and qualification of management fees for certain “friendly” disqualified service businesses (e.g. engineering and medical practices) where the entity earning management fees effectively controls the professional practice.
2. Documentation failures
Section 1202 offers one of the most powerful benefits of the tax code—yet many taxpayers fail to properly document their eligibility. A common issue arises when shareholders claim the QSBS exclusion on gains passed through from partnerships or S corporations but lack visibility into whether the underlying stock actually qualifies.
In these cases, shareholders often rely on a basic qualification letter from the issuing company, which may be incomplete, outdated, or entirely incorrect. Without detailed support regarding original issuance, gross asset levels, and active business requirements, the IRS may disallow the exclusion—even if the shareholder acted in good faith.
Case in point: In Ju v. United States, poor recordkeeping led to disqualification of QSBS benefits, underscoring the importance of thorough and accurate documentation at both the entity and shareholder levels.
3. State-level discrepancies
States such as California and Pennsylvania do not conform to federal QSBS rules, creating a false sense of tax savings that may not materialize at the state level.
4. Future Treasury and IRS guidance
With the expanded benefit, there is always the risk that the U.S. Department of the Treasury and IRS could issue more robust guidance clarifying the rules, which could serve to either support or restrict certain positions being claimed by taxpayers in calculating the exclusion. As with the IRS’s crackdown on employee retention credits, captive insurance, and conservation easements, section 1202 could become a target if perceived as abusive.
Lessons from past IRS enforcement
Micro-captive insurance
In Syzygy Ins. Co. v. Commissioner, the Tax Court ruled that the captive arrangement lacked economic substance and did not constitute valid insurance. The IRS now designates certain micro-captive transactions as listed transactions, requiring disclosure and subjecting them to heightened enforcement.
In a 2025 settlement with Alta Holdings, the IRS pursued penalties under section 6700 against promoters of abusive captive structures, reinforcing its aggressive stance.
Employee retention credit (ERC): A cautionary tale
Originally designed for pandemic relief, the ERC became a magnet for opportunistic advisors. Many businesses filed questionable claims based on overly broad interpretations or misleading marketing. In response, the IRS launched a sweeping enforcement campaign, including audits, disallowances and penalties.
Just like with the ERC, we are now seeing a proliferation of online advisors offering guidance on QSBS planning—some of it aggressive or poorly substantiated. Companies and shareholders should carefully vet their advisors and positions to avoid a repeat of the past. What begins as a legitimate incentive can quickly become a minefield if misused or overpromoted.
In 2023–2024, the IRS even paused processing new ERC claims to address the surge in potentially fraudulent filings. The QSBS landscape could face similar scrutiny if taxpayers interpret the rules too broadly.
Conclusion: Proceed with purpose
The OBBBA opens a new era for tax-free growth—but only for those who plan carefully and document thoroughly. Between the corporation, shareholders and investors in pass-through entities, the parties should:
- Evaluate QSBS eligibility early
- Structure investments with qualification in mind
- Maintain airtight documentation
- Stay informed about state-level and federal changes
- Vet advisors and avoid overly aggressive strategies
Whether looking at a QSB silo or a standalone acquisition, the expanded QSB opportunity should be part of any strategic review of eligible businesses as well as future acquisitions, and taxpayers should seek out qualified tax advice when dealing with QSBS. Act now to capture the benefits—without repeating the mistakes of the past.
Please connect with your advisor if you have any questions about this article.
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Call us directly at 972.221.2500 (Flower Mound) or 940.591.9300 (Denton), or complete the form below and we’ll contact you to discuss your specific situation.This article was written by Nick Gruidl, Nick McCreven and originally appeared on 2025-07-25. Reprinted with permission from RSM US LLP.
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