For some taxpayers, investing in a small start-up business may be a lucrative place to put your money. But, as with any other investment, there are risks. Fortunately, the Internal Revenue Code also provides some relief from the inherent risk of investing in a small business. If executed properly, investors in small businesses can deduct losses from Section 1244 stock far in excess of the $3,000 per year limit on capital losses. They can also pay less capital gains tax when the business becomes successful.

Losses. Under Section 1244 of the Internal Revenue Code, taxpayers are allowed to write off a loss of $50,000 ($100,000 if married filing joint return) on qualifying small business stock in any one year. The loss is allowed in the year the business fails or when the taxpayer sells his stock. This provision applies to both C corporations and S corporations, whether the taxpayer is active in the business or not.

Without Section 1244, a taxpayer realizing a loss from the disposition of the stock of a small corporation would only be able to use the loss to offset capital gains from other investments or ordinary income up to $3,000 per year. In addition to the $50,000 ($100,000 for joint filers) first year loss allowed, any excess losses from Section 1244 stock (over the $50,000/$100,000) can be carried forward and claimed in future years (although in future years, the $3,000 per year limit will apply).

“Qualifying small business stock” defined. In order for losses from the disposition of small business stock to qualify under Section 1244, the following requirements must be met:

• Total original capitalization less than $1 million. When the corporation was formed, the total money or property it received for stock must have been less than $1 million in order for the stock to be Section 1244 stock.

• Business must be active business. The business must be “largely an operating company” with greater than 50% of its gross receipts in the previous five years coming from nonpassive sources.

• Must be original issue stock. Only the original purchaser of the stock is eligible to take advantage of the provisions under Section 1244. The stock must be purchased from the company on original issue to qualify.

• Stock must be issued for money or property only. The stock must be issued in exchange for money or property (other than stock or securities) only. Stock received in exchange for services to the business will not qualify as Section 1244 stock. Also, contributing a note to the corporation in exchange for stock will not qualify.

• Stock must actually be issued. The corporation must actually physically issue stock certificates for the money or property contributed. It is not required that this be done when the corporation is initially capitalized; a corporation can issue additional stock at a later date.

Example: Bob and Mark incorporated ABC Inc. Both of them contributed $100,000 and were issued 10,000 shares of stock. During the year, both of them need to make an additional capital contribution of $50,000 to cover operating expenses. Although the additional capital contribution hasn’t changed their respective ownership percentages in the corporation, the corporation must issue additional shares in order for any potential loss related to the contribution to qualify as Section 1244 stock. Without the actual issuance of stock certificates, the $50,000 would just be an additional capital contribution to the corporation and will not qualify as Section 1244 stock.

Gains. Under the American Recovery and Reinvestment Tax Act of 2009 (2009 Recovery Act), investors may exclude up to 75 percent of the gain from the sale of certain small business stock acquired and held for more than 5 years. The increased exclusion applies only to stock acquired after February 17, 2009 and before January 1, 2011. For purposes of the temporary incentive, a “small business” in this case can have assets up to $50 million and must conduct an “active trade or business.”

Reporting requirements. In the year of a loss, a statement must be included with your individual tax return stating that you are taking a loss pursuant to Section 1244. If audited in subsequent years, be prepared to provide additional information about the corporation that issued the stock such as physical address, # of shares outstanding, etc…; how the stock was acquired and what consideration was paid; and, the fair market value (FMV) of any property and your basis in the property at that time, if the stock was acquired for property instead of cash.

It’s crucial that the requirements for deducting a loss pursuant to Section 1244 be met before a loss is claimed. Failure to meet the requirements of Section 1244 may result in a loss being reclassified as a regular capital loss, limiting your loss against ordinary income to the $3,000 capital loss annual limit. A disallowed loss claim discovered in a subsequent year could result in a very large tax bill.

If you are contemplating an investment in a small business and think that Section 1244 may apply to you, please feel free to contact our office for assistance.