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How Does Code Section 1244 Affect Stock Sales And How Can You Take Advantage Of It?

Starting a small business is an exciting journey, but it also comes with inherent risks. Fortunately, the Internal Revenue Code (IRC) offers valuable tax breaks to incentivize investment in these ventures. Section 1244 is one such provision, providing significant tax relief for qualified losses on certain small business stock.

Ordinary Loss Treatment: A Game Changer

Imagine this: you invest in a promising startup, but things don’t go as planned. Section 1244 steps in, allowing you to treat losses on this “§ 1244 stock” as ordinary losses. This is a major advantage compared to standard capital losses, which are limited to a deduction of $3,000 per year (married filing jointly) and taxed at a less favorable rate. With § 1244, you can deduct the entire loss in the year it occurs, up to a limit of $50,000 (or $100,000 for married filing jointly). This significantly reduces your tax burden and helps soften the blow of a failed investment.

Beyond Ordinary Losses: Additional Benefits

The advantages of § 1244 extend beyond ordinary loss treatment. Losses from this type of stock can also be used to offset Non-business Income (NBI) without limitation. This is crucial for small business owners who may generate income outside their primary business activities.

Understanding the Requirements: Qualifying for § 1244

To qualify for § 1244 treatment, specific criteria must be met, both by the corporation issuing the stock and the investor. Here’s a breakdown of the key points:

  • The Corporation:
    • Must be a “small business corporation” at the time the stock is issued.
    • Defined as having aggregate money and property received for stock, capital contributions, and paid-in surplus not exceeding $1,000,000.
    • Must derive more than 50% of its gross receipts from active business operations over the past five years (excluding royalties, rents, dividends, etc.).
  • The Stock:
    • Issued for money or other property (excluding stock and securities).
    • Issued pursuant to a documented corporate resolution.

Beyond Section 1244: Exploring Section 1202

While § 1244 focuses on loss mitigation, Section 1202 of the IRC offers a potential tax benefit on gains. This provision allows for the exclusion of gains from certain C corporation stock, up to a maximum of $10 million (or $5 million for married filing separately). To qualify, the corporation must meet specific criteria, including:

  • Having aggregate gross assets not exceeding $50 million when the stock is issued.
  • Maintaining an “active business” requirement.
  • The stock being held for more than five years.

Equipping Yourself for Success: Documentation is Key

To maximize the benefits of § 1244, it’s crucial to maintain proper documentation. This includes:

  • Corporate minutes and resolutions related to stock issuance.
  • Accounting and bank records demonstrating the corporation’s qualification.
  • Operational records showcasing the active business nature of the corporation.

Investing in the Future: How We Can Help

Section 1244 and 1202 are powerful tools for both small businesses and investors. If you’re considering starting a small business or investing in one, understanding these provisions can be highly beneficial. Our office has extensive experience in navigating the complexities of tax law related to small businesses. Feel free to contact us for further guidance on how to leverage these sections and optimize your tax strategy.

JS Morlu LLC is a top-tier accounting firm based in Woodbridge, Virginia, with a team of highly experienced and qualified CPAs and business advisors. We are dedicated to providing comprehensive accounting, tax, and business advisory services to clients throughout the Washington, D.C. Metro Area and the surrounding regions. With over a decade of experience, we have cultivated a deep understanding of our clients’ needs and aspirations. We recognize that our clients seek more than just value-added accounting services; they seek a trusted partner who can guide them towards achieving their business goals and personal financial well-being.
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