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by nbclark 2125 days ago
Without knowing your exact situation, one thing to keep in mind is that the preferred value (last valuation / # of shares) of a share is generally a good bit higher than the tax liability (value of a common share from the 409a minus your strike). Still likely a big tax hit, but perhaps slightly better. IMO changes to tax law for illiquid assets is the best but most unlikely option here.
1 comments

Yeah it's a good call out, in this case FMV is about 1/3rd the preferred. Sadly the that still puts it out of reach for me, but means I can afford to exercise at least some.