[calcsam]

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.

[tootall]

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.