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Re:Ask HN: Planning to leave. How best to handle stock options? by tuckermi on Wednesday December 09, 2015 @02:51PM (#10706232)
I think the point is that there is same-year tax liability on the $5M value, but there is no guarantee on getting the $5M payout that same year (or ever, for that matter). When you exercise your options, you now hold shares in a private company, which may restrict your ability to realize the payout in various ways.
Re:Ask HN: Planning to leave. How best to handle stock options? by leroy_masochist on Wednesday December 09, 2015 @06:22PM (#10707597)
Yes, exactly this.