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Re:Ask HN: Exercising stock options with imminent new round ... by calcsam on Monday April 03, 2017 @11:41AM (#14023630)
You should call a tax lawyer ASAP. This is above HN readers' pay grades.

FWIW, we had a similar situation at Zenefits, but were advised it would probably be all right if we exercised before the company officially started raising $.

George Grellas comments on Hacker News frequently, he may be a good option.

I'd also look into secondary markets for selling some of your shares to offset the tax burden.

Re:Ask HN: Exercising stock options with imminent new round ... by tootall on Monday April 03, 2017 @11:50AM (#14023731)
Thanks for the precious information!

I thought about asking here because it's not the first time HN saves my "life" by providing proper perspective on important decisions.