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How can Qualified Small Business Stock save you taxes?

CAUTION: With the recent cuts in capital gains rates, the QSBS may not result  in much, if any, tax savings.

Gain rollover. With limited exceptions, if you so elect, you can 'rollover' gain from the sale of Qualified Small Business Stock (QSBS) sold by you, or by a partnership, mutual fund or 'S corporation' (see 'What is QSBS below') in which you hold an interest. (Partnerships, mutual funds, S corporations, estates and trusts can also elect rollover treatment.) The election is available for QSBS you sold after Aug. 5, '97.

In a rollover in which you are the seller of the QSBS, you can sell the QSBS without currently paying tax on the gain if you (1) held the QSBS sold for more than six months and (2) buy, within 60 days of the sale date, other QSBS (replacement stock) at a total cost at least equal to the total amount you realized from the sale.

The rollover enables you to end or reduce your investment in the QSBS of a corporation without currently paying tax on the gain. Also, because there is no rule requiring you to buy replacement QSBS in only one corporation, you can, in one or more rollovers, lessen your risk by spreading your investment among multiple small corporations.

Gain not currently taxed in a rollover ('unrecognized gain') will be fully taxed on a sale of the replacement stock, if the replacement stock is not itself rolled over and the amount received from the sale of the replacement stock exceeds the basis of the replacement stock (generally, your basis is the amount you paid for the stock) as reduced by the unrecognized gain. However, if the later sale is for a lesser price, all or part of the gain will be permanently excluded from your income. Part of the unrecognized gain will also be permanently excluded if the later sale itself qualifies for the 50% exclusion discussed below.

50% gain exclusion. A 50% permanent exclusion of gain from the sale or exchange of QSBS is available to the same types of taxpayers as those eligible for the gain rollover. No election is required for the permanent income exclusion to apply.

To qualify to permanently avoid paying tax on the gain, you must hold the QSBS for more than 5 years before you sell or exchange it.

The amount of gain excludible in any tax year is limited to 50% of the greater of: (1) $10 million ($5 million for a married individual filing separately) reduced by the amount of gain taken into account in earlier years, or (2) 10 times the basis—excluding amounts added to the basis after the stock was issued—of the stock disposed of in the year. Both limits are applied on a per-taxpayer per-issuer basis. For example, if a married couple filing jointly owns QSBS in 3 different corporations, they can together exclude at least $15 million of gain ($10 million of gain x 3 x 50%).

The inflexibility caused by the more-than-5-year holding period required for the 50% exclusion may be reduced by the availability of the gain rollover discussed above. For example, consider someone (Mr. Smith) that, on Dec. 1, Year 1, buys QSBS in corporation A for $1 million, sells that QSBS after two years for $2 million, purchases $2 million of QSBS in corporation B during the 60-day rollover period and, on Dec. 2, Year 6, sells the B stock for $4 million (without buying replacement stock). Even though Mr. Smith held neither the A nor B stock for more than 5 years, he satisfies the more-than-5-year holding period requirement and will have a total taxable gain of only $1.5 million.

In connection with the 50% exclusion, you should know that 42% of the excluded part of the gain—28% for stock with a holding period that begins after Dec. 31, 2000—can expose you to the alternative minimum tax (AMT). However, exposure to AMT can, at most, reduce, but can't eliminate, the tax benefit of the 50% exclusion.

What is QSBS. To be QSBS, stock must be issued after Aug. 10, '93 and, with exceptions, must be stock you acquire when it is issued (directly or through an underwriter) in exchange for money, property (other than stock) or services (other than underwriting). Also, the stock must be stock in a corporation that:

(1) for substantially all the time that you hold the stock is not a mutual fund or other special type of corporation;

(2) at the time the stock is issued and for substantially all the time that you hold the stock, is a U.S. corporation and is not an S corporation (a corporation that, under subchapter S of the income tax provisions of the Internal Revenue Code, has elected to not be subject to the regular income tax on corporations);

(3) at all times after Aug. 10, '93, and before the issuance of the stock, has gross assets that don't exceed $50,000,000 (taking into account predecessor and affiliated corporations);

(4) immediately after the stock is issued, has gross assets that don't exceed $50,000,000 (taking into account affiliated corporations);

(5) for substantially all the time that you hold the stock, uses—taking into account subsidiary corporations—more than 80% of its assets in the active conduct of a trade or business. Some types of businesses (like farming), even if actively conducted, don't count toward satisfaction of this 80% 'active business' test, and some investments in real estate, stocks or securities can cause an otherwise qualifying corporation to fail the 80% test.

As you can see, the rules for QSBS and its benefits are complicated and some rules including some special pro-taxpayer rules not discussed above also may apply. Should you be interested, you should discuss QSBS with your tax advisor before you incorporate, but certainly before you make any tax elections.