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Unlocking the Tax Potential of Qualified Small Business Stock

As a savvy investor or small business owner, understanding the nuances of Qualified Small Business Stock (QSBS) can be a game-changer for your tax strategy. Established under the Revenue Reconciliation Act of 1993, QSBS provides significant tax incentives, allowing you to potentially exclude up to 100% of capital gains from taxable income as per Section 1202 of the Internal Revenue Code. In this article, we delve into the essentials and complexities of QSBS, offering key insights into maximizing your tax benefits.

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Defining Qualified Small Business Stock: QSBS pertains to shares in a C corporation eligible for tax exclusions specified by Section 1202. It's crucial to know that not every C corporation qualifies; specific conditions relating to issuing corporations, holding periods, and operational metrics must be met.

Eligibility Criteria for QSBS: To be classified as QSBS, stock must be issued by a domestic C corporation conducting a qualified trade or business. Important criteria include:

  • Small Business Status: At issuance, the corporation's gross assets must not exceed $50 million, increasing to $75 million after July 4, 2025.
  • Active Business Requirement: At least 80% of the corporation's assets should be actively used in the trade or business.
  • Qualified Trade or Business: Typically, professional service-based businesses like law and finance, as well as certain other sectors, are excluded. Qualifying businesses must focus on eligible activities.
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Key Tax Advantages of QSBS: The primary appeal of QSBS is the potential exclusion on capital gains:

  • Stock acquired before 2009: 50% capital gains exclusion.
  • Post-2009 through the 2010 Small Business Jobs Act: 75% exclusion.
  • Post-2010 and before OBBBA: 100% exclusion for stock acquired from September 28, 2010, to July 5, 2025.

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Under the "One Big Beautiful Bill Act" (OBBBA), stocks acquired post-July 4, 2025, have reshaped exclusions based on holding periods:

  • Three-year holds: 50% exclusion
  • Four-year holds: 75% exclusion
  • Five-year holds: 100% exclusion

Prior to July 5, 2025, the excludable gain is capped at $10 million or ten times the investment basis, whichever greater, increasing to $15 million after OBBBA with inflation adjustments.

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Disqualifications and Other Considerations: Certain scenarios disqualify stock from QSBS benefits:

  • Disqualified Stock: Stock obtained via repurchase within two years.
  • S Corporation Stock: This stock is ineligible unless there's a conversion to C status.

Strategic Transfers and Rollover Opportunities

  • Transferring as Gifts: Gifts of QSBS retain the holding period for eligibility.
  • Passthroughs via Partnerships: Partners might benefit if conditions are satisfied.
  • Gain Rollover under Section 1045: Defers gains on QSBS held over six months, reducing basis on new stock. Future exclusions apply post-qualified holding period.

Tax Considerations: Not all QSBS gains qualify for exclusion; up to a 28% tax rate can apply to non-excludable gains. Alternative Minimum Tax (AMT) implications have evolved, with current amendments removing AMT preference considerations for QSBS exclusions.

QSBS represents a strategic tax-saving device, particularly empowering investors to support domestic small businesses. By comprehending its qualifications and potential advantages, investors can more effectively design their portfolios. Count on ChesebroCPA for astute guidance tailored to your business’s unique tax landscape. Through practical expertise and tailored advice, we alleviate tax stress and enrich financial clarity.

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