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Comment by ushakov | Hacker News Reader

most of the startups that offered me stock options had completely exaggerated valuations, so...

my heart goes to engineers, who joined a startup on bold promises to make it, but never got to IPO, M&A or even worse - were forced to execute options to later sell them at loss

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This happened to me as well. Ridiculous billions+ valuations for companies that have not much of a moat and questionable market sizes, plus competition. Consequently the stock grants were for laughably thin slices of the company for massively inflated "Fair" Market Values per share, not to mention below-average salary offers. Basically, many startups think employees are only too willing to assume inordinate amounts of risk to make founders and their cronies rich while putting their futures on the line, and expect employees to be grateful they are given such opportunities. F that.

So many startups never IPO, and their stock options are effectively $0. When they leave they have a small window to exercise them and pay capital gains tax (with inflate valuation, this could be $100k or more).

Anyone thinking of making money off stock options at pre-IPO startup are taking a get a) valuations are realistic b) startup will IPO. In this current environment, both are false.

IIRC, at Stripe, and other nice-minded startups, you have 7 years to exercise, instead of the usual 60 days.

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