Date: Mon, 9 Apr 2001
From: Bruce
A follow on to the stock swap NQSO exercise FAQ answer - so there are 90 new shares and 10 replacement shares - do the 10 replacement shares get kept by the company as payment for the exercise? If you also have them withhold shares to pay the tax withholding, do you record this as a sale of X shares from the specified lot of 90 new shares?
Thanks, Bruce
Answer
Date: Wed, 25 Jul 2001
Hello Bruce,
I have so many FAQs, I’m not sure which one you are referring to.
If 10 previously owned shares are exchanged to exercise an option for 100 shares, the employer may either take the certificate for the 10 shares and issue a new certificate for 100 shares, or just have the employee document already owning the 10 shares and issue a certificate for 90 additional shares.
The employee generally pays cash for the withholding taxes.
For a cashless exercise, some of the shares will have to be sold to get the cash to pay the taxes, resulting in reporting some taxable income.
Good luck!
Mike Gray
IRS Circular 230 Disclosure: As required by U.S. Treasury Regulations, you are hereby advised
that any written tax advice contained in this answer was
not written or intended to be used (and cannot be used) by any
taxpayer for the purpose of avoiding penalties that may be
imposed under the U.S. Internal Revenue Code.