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Comment on Ask HN: Startup options and exercising

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IANAL. Advice is worth what you paid for it...

There is hardly ever any valid reason to exercise your options before an IPO or similar equity event. There is a small tax benefit to exercise and hold them for at least 1 year, but there is HUGE risk in the value being wiped out or diluted.

There can be a small benefit in being an actual shareholder, as you are supposed to get minutes from the board meetings. But, you don't need to exercise all your options to do that, $1.00's worth would be enough.

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