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  • Writer's pictureNick Smith

How to Sell your Small Business Tax-Free*

Negotiating the purchase price for your business is probably your primary concern. In-depth financial analysis and similar transactions in your industry may bring you and your buyer to an agreement on the enterprise value of your company; however, the structure of the transaction, not just the headline multiple or dollar value, ultimately determines what you receive at close and what ends up in your pocket after Uncle Sam takes his portion. We talk about simple transaction structures in another article here, but in this post we’ll examine a specific tax law that could make Uncle Sam’s take much smaller.

For entrepreneurs searching for a tax-free windfall, the Qualified Small Business Stock (QSBS) 1202 exemption seems to offer an answer. This powerful incentive offers the potential to exclude up to 100% of capital gains on the sale of qualifying stock, making it a potential game-changer for those preparing to sell their business. However, the asterisk in our title above should probably be in size 50 font. The QSBS 1202 requires a deep understanding of its requirements, limitations, benefits, and potential pitfalls. Finally, the QSBS 1202 is only available in a stock purchase, as opposed to an asset purchase, which pushes risk onto the buyer and may result in a lower purchase price. 

The Requirements

The siren’s song of a tax-free sale may have prompted you to read this post, but to take advantage of the QSBS 1202, you must meet some eligibility requirements:

  • C-Corps Only: To qualify for the QSBS exemption, the stock must be issued by a US C-corporation

  • Gross Assets: At all times before stock issuance (including immediately after the stock is issued), the company's gross assets cash, and other property held by the corporation, must total $50 million or less.

  • Active Business: The company must be engaged in an active trade or business, excluding passive activities like investments or real estate holding. At least 80% of the company's assets must be used in its qualified trade or business during substantially all of the taxpayer’s holding period. 

  • Minimum Holding Period: The shareholder seeking exemption must hold the stock for at least five years.

The Limitations

While the exemption presents a substantial opportunity, it's important to acknowledge its limitations:

  • Gain Ceiling: The exclusion applies only to the greater of $10 million or 10 times the adjusted basis of the stock. For high-value exits, a portion of the capital gain may still be taxable.

  • Holding Period: The five-year holding period can be a significant hurdle for owners seeking quick exits.

  • Risk of Disqualification: Certain events, such as mergers or acquisitions, can disqualify the stock from the exemption, requiring careful planning and due diligence.

  • Stock Sales Only: QSBS 1202 does not apply to transactions structured as asset sales.

The Benefits

Despite the limitations, the potential benefits of QSBS 1202 stock sale are undeniable:

  • Substantial Tax Savings: For QSBS 1202 qualifying sales, sellers have the opportunity to eliminate up to 100% of capital gains tax on the proceeds of the stock. 

  • Long-Term Growth Incentive: By aligning tax benefits with holding periods, the incentive encourages investors and founders alike to stay invested and support the long-term growth of companies.

The Pitfalls

Before embarking on the QSBS journey, be aware of the following:

  • Complexities and Uncertainties: QSBS is a complex law with intricate interpretations and evolving regulations. Consulting with a qualified tax professional is crucial to avoid unintentional missteps.

  • Documentation Burden: Maintaining meticulous records and adhering to stringent documentation requirements is essential to claim the exemption effectively.

  • Transaction Structure: Business buyers often seek asset sales when acquiring companies. Stock sales can increase risk for the buyer. Increased buyer risk will result in a lower purchase price.

Make an Informed Decision

QSBS 1202 is a powerful tool, but it's not a one-size-fits-all solution. Always seek expert guidance from qualified professionals. In saving money through lower taxes, increased risk from a stock sale may reduce the negotiated purchase price. QSBS 1202 gives specific stock sales a potential tax haven. Know what to ask of your buyer or seller agent and if we can be helpful, please let us know.

For more detail on QSBS 1202, readers can navigate to the IRS guidance on tax returns, or can reference this article on the topic.



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