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by recursivenature 1583 days ago
Couple of important points I haven't seen mentioned yet.

1 - You should already have an option exercise form that you can fill out to actually exercise these options / notify the company you want to do so. It is important that you fill this out and have it in writing, email/certified mail/whatever, that you sent this in with a request to exercise because of 2.

2 - Depending on your employment agreement and your role, you should find out exactly what your Post-Termination Exercise Window is. This is the time period in which you have, after a certain condition, the ability to exercise your options. If you do not exercise them within this period, in most cases, the options will revert back to the company and you will not have the ability to exercise them in the future. This can often be as short as 30-90 days. While I would try to assume positive intent, you need to make sure they are not trying to wind the clock down against you.

3 - You should also be aware of the cost to exercise the options and the number of options that you have vested at the time you leave. In your grant, there will typically be several components, most importantly the strike price, the number of options and the vesting schedule (typically 4 years with a 1 year cliff). While there is much to work through with your lawyer, in general, Strike Price ($1.00) * # Options Vested (5,000/10,000) = Cost to Exercise ($5,000)

4 - Keep in mind that once exercised, if the shares turn out worthless, you can't get the funds back. The shares can end up worthless for any number of reasons including Investor Preferences, Debt Overhang, or a sale price that is too low. Overall, do your own risk/reward calculation here to make sure its worth the price of admission.

5 - I'd echo the points here in that they may never have had an employee exercise their options previously. Believe it or not, most employees do not exercise when they leave a company, and you may have been the first to do so here.

6 - Finally, document all of this thoroughly. If for whatever reason they are attempting to run out the clock on your Post-Termination Exercise Window, ensuring that you have documented you WANT to exercise them and the company didn't execute on your desire is critical in eventually getting the options.

(IANAL and you should find counsel to work through the specifics with you, this is not legal advice and there are unintended tax consequences that may occur if you don't consult a tax professional - Options are complicated!)