

Ask HN: Startup options and exercising - paradox95

I am approaching my first full year at a startup and my options cliff for 25% of my options. Should I exercise that 25% immediately or let it sit? What are tax repercussions on exercising vs. not exercising?
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brk
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.

