I exercised ISOs and all I got was this crummy certificate.
April 10, 2013 10:01 AM   Subscribe

Should I have received additional paperwork after exercising ISOs in a cashless transaction from my former employer?

I exercised some ISO's in early 2012 from my former employer (a privately held company) whom I parted ways with in 2011. I opted for what the CFO called a cashless exercise and sold a portion of my options to cover the costs so nothing was out of pocket.

Since then, I have received a stock certificate and nothing more. No brokerage statement, no W-2, no 1099-B. All I have is an informal email explaining the math and the issued certificate. I do not have a broker, or a CPA. I'd like to avoid paying out the nose for a tax accountant as the total value of my remaining stock is less than $4000. I'm trying to fill out my taxes now but all the forms and schedules that seem like they're pertinent require information from forms they assume I've received. Should my former employer have issued me these forms or some other information?
posted by okay okapi to Work & Money (2 answers total)
I am no tax expert (I'm not even a reliable novice), but I would say yes, you should get a 1099 for both exercising and selling shares. These are both (I believe) taxable events. If it was me, I'd call up your former CFO and ask if he has filed them, has them for you, or any advice on what taxes to pay (maybe they have a CPA for current employees who would do it for you on the cheap?).

Also, someone previously mentioned that the IRS actually has awesome customer service. This is probably the worst time of the year to try, but if you have all the numbers in front of you, they might be able to tell you what to do and how much to pay.
posted by Phredward at 11:06 AM on April 10, 2013

Obtaining non-qualified options with a fair market value different than the strike price is also a taxable event for that tax year. However, since yours are ISOs, your strike and holding price are the same and start when you receive them, so there's no forms for the simple exercise (only for the sales).
posted by kcm at 11:37 AM on April 10, 2013

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