A special tax break is designed to help qualifying small C corporations raise capital by allowing long-term noncorporate investors in original issue stock to cut the tax on their profit.

If a five-year holding period is met, qualifying investors can exclude 50 percent of their gains on qualified small-business stock from taxable income. The nonexcluded portion is taxed at the maximum rate of 28 percent, for an effective tax rate of 14 percent (50% x 28%). However, for exchanges after May 5, 2003, through 2010, seven percent (previously 42 percent) of the 50 percent of excluded gain is a preference item that must be factored back in for AMT purposes.

In order to qualify for this special break, taxpayers must jump through a large number of hoops.

The 50 percent capital gains exclusion applies only to gain on eligible stock (1) originally issued by a qualifying corporation after August 10, 1993, and (2) held for more than five years. The highlights of this break follow:

• The stock must be acquired in an exchange for money or other property (other than stock), or as compensation for services provided to the corporation (other than acting as the stock's underwriter).
• The small business must be a regular C corporation; it must have $50 million or less in aggregate capital as of the date of stock issuance; and at least 80 percent by value of corporate assets must be used in the active conduct of one or more trades or businesses.
• The corporation cannot be involved in the performance of personal services (such as health or law) or in the finance, banking, leasing, real estate, farming, mineral extraction, or hospitality industries. A number of other types of businesses, such as mutual funds and REITs, are also disqualified.
• The exclusion for each eligible corporation applies only to the extent that the gain does not exceed the greater of (1) 10 times the taxpayer's adjusted basis in the stock disposed of during the tax year (post-issuance additions to basis are disregarded), or (2) $10 million ($5 million for marrieds filing separately), reduced by gain excluded in earlier years from sales of stock in the corporation.
• Although a post-issuance purchaser of otherwise qualified stock doesn't get the exclusion, the tax break is preserved for those who receive such stock as a gift or due to the death of the original purchaser. The transferor's holding period also carries over to the transferee. Similar rules apply to qualified stock distributed by a partnership to its partners.
• Individuals can roll over, tax-free, gain realized on the sale or exchange of qualified small business stock provided that the proceeds are used to purchase other qualified small business stock within 60 days of the sale.