equity-question on Hacker News
Otherwise, of course, waiting until the options are profitable is the best move and is risk-free.
If I choose to do so, then I will have no risk of a loss, because like you said, if the option is underwater, then I will simply not exercise.
The only reason I may end up having to take risk is due to limits on exercise windows. For example, I have to exercise any vested option within 6 months of leaving the company. In that case, I may want to buy the stock, and hold onto it if I expect it to appreciate. Then I will be taking risk, effectively like buying any other stock that may depreciate.
I received an offer for a senior role at a US startup. A key part of the compensation is a very large stock option package.The problem is that exercising all these options will cost me hundreds of thousands of dollars.That seems like a big, scary gamble. Effectively, I'll be investing six figures in a pre-IPO startup. I am not the type of wealthy individual who can afford to make this sort of...