Don't spend any money until you are sure you'll be getting a return -- def. not on day one.
I've never actually heard of a compensation structure which has >$100k of options to even spend on day one. Most of the time they are vested on a schedule.
I've never actually heard of a compensation structure which has >$100k of options to even spend on day one. Most of the time they are vested on a schedule.
Do this only for very early stage startups where your total expense might be a few thousand dollars for maybe 1% or more of the startup. At most, you lose a few thousand dollars.
Spending $100K to optimize possible future taxes is a bad idea. At this stage, you should just think that future AMT is a good problem to have. Put the $100K in safer instruments.
I will hold off until then.
I certainly wouldn't drop 100k unless they offer a commensurate signups bonus (the 100k goes to the company so they could give you a bonus of $100k if you exercise the options which should help, though you'd still be on the hook for the taxes on that bonus).