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Re:Ask HN: Anyone have stock option horror stories? by shagie on Thursday March 17, 2022 @08:53PM (#30717520)
I had this situation back in the dot com crash.

I sold 2000 options in June. The following April I had to sell 15,000 to pay the taxes on the 2000. The following April I had to sell another 10,000 to pay the taxes on the 15,000.

If I had sold 20,000 instead of 2,000 and used that to pay taxes, I would have been in a far better financial situation.

Fortunately, I never went into the red, but I know people who did.

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