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Using Stock To Exercise Options

A stock-for-stock option allows holders of an option to use shares of stock they already own to pay for new shares. With a stock-for-stock option exercise, the option holder pays the option exercise price by delivering (either by physical delivery or by attestation) previously-owned shares of Company stock with a value equal to the option exercise price. This is a expeditious method of exercising a stock option, because there is no need to obtain cash to exercise the option. Further, by exercising an option in this manner, the option holder is able to avoid taxable gain from the sale of stock to obtain cash for the purchase of new shares.

Plan Provisions

Most stock option plans permit stock-for-stock option exercises. If not, the plan must be amended in order for this type of transaction to take place. In most cases, a plan amendment to add a stock-for-stock option exercise provision will not require shareholder approval, although the specific terms of each plan must be reviewed.

Amending an option plan or an individual option agreement to permit stock-for-stock option exercises should not be considered a "modification" for purposes of Section 162(m) of the Internal Revenue Code (the $1,000,000 deduction limitation). However, such an amendment would be considered a "modification" for "incentive stock option" (ISO) purposes. As a result, amending an option plan or agreement to add a stock-for-stock exercise feature to an ISO will ordinarily disqualify the ISO and convert the ISO into a "nonstatutory stock option" (NSO) for tax purposes. Companies should also consult with their accountants to determine whether any such amendment triggers a compensation expense for financial accounting purposes.


The shares that are used to pay the option exercise price can be delivered either by actual physical delivery of a stock certificate to the company or through attestation. With attestation, the option holder represents to the company, by executing an affidavit, that he or she owns other shares of company stock in a quantity sufficient to exercise the option. Attached is a sample form of attestation affidavit. Unlike stock certificates, an attestation form can be delivered by fax or e-mail. Upon receipt of the attestation form together with the company's option exercise form, the company simply issues the net shares representing the spread at exercise.

An example of a stock-for-stock option exercise follows:

  • An employee receives an NSO for 1,000 shares of company stock at an exercise price of $10 per share, the fair market value at the time of grant. At the time of exercise, the company stock has a fair market value of $25 per share.
  • The executive delivers (either by physical delivery or by attestation) 400 shares (the "Delivered Shares") of stock worth $10,000 (the aggregate option exercise price) to exercise the option. The executive receives (or retains in the case of attestation):
    • a certificate for 400 shares of company stock representing the previously-owned shares (the "Replacement Shares"), and
    • a certificate for 600 shares of company stock representing the spread at exercise (the "Gain Shares").

Tax Consequences

Exercising a stock-for-stock option creates a tax-free exchange of old shares for new shares. This exchange does not require the report of any taxable income. In the exchange of old for new, the additional shares received are for zero payment. These new shares will have the same basis and holding period as the old shares. However, tax laws change and the tax consequences should be reviewed with an accountant for a particular situation.

The new shares that are received maybe required to be reported as compensation income if the stock is vested when it is received. These shares have a basis equal to the amount of compensation income reported and the holding period begins when the shares are received.

Advantage of the Stock-for-Stock Option

The true advantage for a stock-for-stock option exercise is in not having to obtain cash to exercise the option. If it is necessary to sell stock in order to exercise a stock option, a capital gains tax will be imposed on the sale of that stock. However, by trading old stock for new stock in a stock-for-stock option, the capital gains tax can be deferred. Eventually, a capital gains tax will be imposed when the stock is sold, but the timing of the sale can be planned for minimal tax consequences.

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