Small Business Stock Sales and Exchanges

Corporate stock is considered an investment, in which the shareholder is distinct from the business. Thus, ownership of the shares is considered a capital asset, even if the equity interest is in noncapital business assets. Hence, gain or loss from the exchange of stock is a capital gain or loss.

Stock sales by individuals are generally given preferential tax treatment. If a capital gain is a long-term capital gain, meaning that the asset has been held longer than 1 year, then the tax rate will be 0%, 15%, or 20%, depending on the taxpayer's income; otherwise it is considered ordinary income, subject to the marginal tax rate of the shareholder. There may be other tax advantages for small business stock if they qualify under IRC §1244 or §1202. However, a corporation does not gain preferential treatment from the sale of a capital asset, since a capital gain is taxed as ordinary income. Furthermore, a corporation can only deduct capital losses from capital gains.

Public stock is a highly liquid asset that can easily be converted into cash, but stock in a private corporation is much less liquid, since there is no public disclosure of the sale price. Instead, the seller and buyer negotiate privately to arrive at a mutually agreed upon price. However, in many cases, the stock of closely held corporations cannot simply be sold to anyone, since the stockholders can be subject to buy-sell agreements, which often stipulate that the stock 1st be offered to other shareholders or to the corporation, or the sale must be approved by the Board of Directors before they can be sold to a 3rd party. S corporations, in particular, must restrict the sale of stock, since only United States citizens or residents can own stock in an S corporation. Since there is no public bidding on small business stock that would set its value, to minimize shareholder disputes and to avoid expensive professional appraisal or litigation, buy-sell agreements are often subject to a formula to determine the price of the stock, such as discounted cash flow or the capitalization of earnings.

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The gain or loss of a stock sale is equal to the sale price, or equivalent value, minus the stockholder's tax basis in the stock, which is generally equal to the purchase price of the stock plus commissions on the transaction or to the substituted basis of property if the stock was acquired in a nontaxable §351 exchange. If the stock was acquired at different times and at different prices, then the owner must keep track of stock purchase dates and prices. Subsequent contributions of capital by the shareholder or a return of capital from the corporation to the shareholder changes the basis of the stock – contributions increase the stock basis, while a return of paid-in capital decreases it.

When stock is sold, the shareholder can decide which lots of stock were sold; if the shareholder cannot determine when the stocks were purchased or the purchase price, then the tax code stipulates that the basis of the earliest acquired stock must be used.

Private stock finances many small businesses, which helps to create jobs and its concomitant tax revenue, so Congress added some sections to the Internal Revenue Code, specifically IRC §1244 and IRC §1202, to promote the sale of what is generally referred to as small business stock, by giving certain tax advantages to their sale, thereby promoting the growth of the economy, which is largely effected through the creation of small businesses. Consistent with these objectives, these tax advantages only apply to active businesses, not businesses created largely for managing investments or businesses that provide the services of its employee-owners, such as personal service corporations. The corporation must also directly benefit from the initial stock sale, so stock qualified for these tax advantages must be bought directly from the corporation, not from another stockholder.

Section 1244 Stock

A C corporation can issue a certain type of stock, called §1244 stock, which receives preferential tax treatment if the shareholder suffers losses on the stock. IRC §1244 allows stockholders of qualified stock to treat losses from the sale of the stock as a net operating loss from a trade or business and, thus, deductible from other forms of income. If the business fails or if the shareholder sells the stock at a loss, then up to $100,000 ($50,000 if married filing separately) of the loss can be deducted against other ordinary income in the 1st year of the loss. The $100,000 limit applies even if only 1 spouse owns the stock. Any losses over $100,000 are considered capital losses and can be carried forward but only $3000 per year can be used to offset ordinary income — remaining losses must be carried forward. However, any amount of §1244 losses can be used to offset capital gains. To claim a loss under §1244, the taxpayer must file a statement with his individual tax return to explain the loss. The loss is claimed on Form 4797, Sales of Business Property.

Example: You invest $142,000 in a small business corporation that qualifies as a §1244 corporation in exchange for §1244 stock. The corporation subsequently goes bankrupt, with no distributable assets for its equity holders. Therefore you have lost all $142,000 of your investment. However, since you make $250,000 annually as a neurosurgeon, you can deduct $100,000 of your loss against your working income. The remaining $42,000 can be deducted in future years. If you have no capital gains in future years, then you can only deduct $3,000 per year for the next 14 years.

To receive Section 1244 treatment, the following requirements must be satisfied:

Additional rules apply to stock that was issued after June 30, 1958 but before November 7, 1978.

Section 1244 does not apply to any contributions made after the initial shares are issued. However, later contributions can qualify if the investor receives shares that were authorized but not issued. The §1244 stock should be issued pursuant to a written corporate resolution. A loss can be claimed by individual shareholders as a §1244 stock loss on Form 4797, Sales of Business Property and must be filed with the shareholder's individual income tax return.

Worthless Securities

A §1244 loss can also be claimed on worthless securities; however, determining when the securities became worthless can be problematic. A company declaring bankruptcy or becoming insolvent is a good sign that its securities are worthless. However, in some instances, they may have some value if the company is reorganizing. Since it is sometimes difficult to determine exactly when a security becomes worthless, the tax code allows the recognition of loss for worthless securities on an amended return for up to 7 years after the due date of the year in which the securities became worthless. The loss can also be recognized if the stock owner relinquishes all ownership rights to the stock, effectively abandoning it.

Section 1202 Qualified Small Business Stock

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A non-corporate taxpayer who has held small business stock that qualifies under IRC §1202 for more than 5 years can exclude at least 50% of any gain from the disposition of the stock. More can be excluded if the stock was issued by a corporation in an Empowerment Zone or if it was issued within certain dates.

Stock Exclusion
Qualified Small Business Stock50%
Issued by Corporation in Empowerment Zone60%
Issued February 18, 2009 – September 27, 201075%
Issued September 28, 2010 – December 31, 2013100%Not included as an AMT preference item.
Issued After 201350%

However, except as noted in the table, 7% of the excluded gain is an AMT tax preference item includable in the seller's alternative minimum taxable income.

Qualified small business stock must also have been issued after August 10, 1993 by a C corporation and acquired by the taxpayer as an original issue in exchange for money, property, or, unlike for §1244 stock, for services provided to the corporation. Stock that has been acquired because of a conversion from preferred stock or by the exercise of options or warrants is deemed to have been acquired as original issue. However, qualified small business stock cannot be acquired from another stockholder, since the corporation must be the seller.

Except for a regulated investment company, the issuing corporation must be a domestic C corporation, or a cooperative or other similar pass-through corporation, with aggregate gross assets that does not exceed $50,000,000 at the time of the stock's issuance. Members of a controlled corporate group are considered 1 corporation when applying the $50,000,000 asset test. Furthermore, during the taxpayer's holding period, at least 80% of the corporation's assets must have been used in an active qualified trade or business (active business test), which does not include the performance of services in such fields as health, law, engineering, architecture, hospitality, farming, insurance, finance, mineral extraction, or any industry that primarily provides a service. The main industries that benefit include manufacturing, technology, and retail and wholesale.

Qualified small business stock can also be rolled over if it was held for longer than 6 months and replaced with the purchase of other qualified small business stock within 60 days of the sale— referred to as a §1045 rollover. The replacement stock must meet the active business requirement for at least 6 months after the purchase. The holding period will be added onto the holding period of the previous stock and any gain realized on the purchase of the replacement stock reduces the taxpayer's basis in the stock. Special rules apply to partnerships and limited liability companies.

Section 1202 gain exclusion is limited to the greater of:

This rule applies to any 1 corporation.

Example: Section 1202 Exclusion

Assume that you have 40,000 shares of small business stock that qualifies under §1202, and that you sell some of the stock in 2008 and the remaining shares in 2015. Using the given facts provided by the table below, you calculate your exclusion amounts thus:

Given Facts
Number of Shares40,000
Purchase price per share
(stock basis)
$60
Date acquired2000
2008 Stock Sale
Number of shares sold in 200812,000Note that the taxpayer has held the stock for more than 5 years.
2008 Sale Price per Share$400
2008 Gain =
Sale Price – Purchase Price =
$4,080,000
$10,000,000 Limitation$10,000,000= $10,000,000 – Eligible Gain in Prior Years
10 × Basis of Stock disposed during the year$7,200,000= 10 × Number of Shares Sold × Stock Basis
= 10 × 12,000 × $60
Applicable Amount Eligible for Section 1202 Exclusion =$4,080,000= Entire Amount since it is less than the Greater of ($10,000,000 Limitation or 10 × Basis of Stock Disposed during the Year)
2008 Excludable Amount = Gain × 50% =$2,040,000
2015 Stock Sale
Number of shares sold in 201528,000
Sale Price per Share$700
Gain$17,920,000= Sales ProceedsStock Basis
= 28,000 × $70028,000 × $60
$10,000,000 Limitation$5,920,000= $10,000,000 – Eligible Gain in Prior Years
= $10,000,000 – $4,080,000
10 × Basis of Stock disposed during the year$16,800,000= 10 × Number of Shares Sold × Stock Basis
= 10 × 28,000 × $60
Applicable Amount Eligible for Section 1202 Exclusion =$16,800,000= Greater of ($10,000,000 Limitation or 10 × Basis of Stock Disposed during the Year)
Section 1202 Exclusion = Eligible Amount × 50% =$8,400,000.0

S corporation stock is not eligible for §1202 exclusion since it only applies to C corporations. However, S corporation stock can qualify as §1244 stock. When an S corporation shareholder sells the shares, the stock basis must be adjusted by the allocations of income and losses and distributions from the corporation up to the date of the sale.

Deferred Gain Recognition by Investing in a Specialized Small Business Investment Company

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Up to $50,000 ($25,000 if married filing separately) of gains from the sale of publicly traded securities can be deferred annually by reinvesting the proceeds, within 60 days, in either stock or a partnership interest of a specialized small business investment company (SSBIC). The gain is deferred by reducing the basis in the stock or the partnership interest by the amount of the deferral, so the gain is recognized when the SSBIC interest is sold. However, there is a $500,000 lifetime limit ($250,000 if married filing separately) on the deferrals.

An SSBIC is a partnership or corporation licensed by the Small Business Administration under §301(d) of the Small Business Investment Act of 1958 to provide venture capital to small businesses owned by minorities who are deemed socially or economically disadvantaged. The capital is provided as either straight debt financing or as equity participation loans to either provide startup funding or help a small business grow. The SSBIC uses its own private source of funds plus borrowed money guaranteed by the Small Business Administration. IRC §1044