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Not an answer to your question,but something you might consider in any case:
So I’m a contractor for a new US startup
Arguably, you aren't, because of the monthly pay and option grant.
This impacts what NI and income tax you pay, how you pay tax on any option exercises, and how the startup pays NI.
(I may be making some completely incorrect assumptions, of course.)
NotThamesWater
haveo
So I’m a contractor for a new US startup, as part of my payment we are awarded stock option grants on top of my monthly pay. There was an initial vesting period which has now past, and new options vest monthly.
Before hand I did a bit of reading about how these work, and the fact that I can choose to exercise them, but I have no clue about timings and when the right time to do that would be. For example is it best to hold off exercising them until it’s clearer that the company is going to succeed? Anyone been through a similar process and have any insight?