Most companies issue options to be exercised in a very window after an employee leaves a company, and don’t offer to cover the cost to exercise. What this means is that while you are getting a discount on the opportunity to purchase stock in the company (based upon the increase in value of the company since you started working there), when it comes to exercise its very difficult to justify a several thousand dollar expense that more or less amounts to buying stock in a very early stage company.

If I wanted to do this I would simply buy stock in a company without working to earn the privilege to buy it. Because the 3 months to exercise is such a short amount of time usually not enough has changed in the company to indicate whether or not that purchase is a wise investment. Some companies give you the option of immediately selling back the stock and simply receiving back the value of the discount on the exercise but this is usually not the long term investment people are looking for when they say equity, and is usually quite small.

Ive gotten bit by this several times for the companies I worked for previously and because the exercise window was very short and the cost to exercise was not covered, I couldn’t justify spending several thousands of dollars on the exercise even with companies that I was very confident in.

When people refer to golden handcuffs they usually refer to the vesting period of the options but it actually has more to do with the fact that the options must be immediately exercised if someone has to leave, and because I live in an at will state thats a really big liability for the options to have no value. Can anyone corroborate this? Are the options I’m getting being structured to have no value? What types of things should I ask for so I can actually get an investment in the company long term? Is it weird to ask for straight stock issuance instead? Are there more resources out there to help me with this?

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