>The worst time to join a startup is anywhere in between. The exercise price of your options is too high on day 1 you can't afford to buy them, then you work there for years and become vested on paper but can't do anything about it, then you leave prior to an IPO and you still can't afford to buy the options so they cancel and you are left with nothing.
Hedge with far OTM (1-5 delta?) LEAPS puts in same-industry/sector competitors or market indices? At least reduce some crash risk, though I am not sure how you run your stock options compensation through BSM without a market to price against. Probably should figure what your VaR is for an x-sigma crash and try to get a hedge which will roughly balloon to that level under high vanna.
Hedge with far OTM (1-5 delta?) LEAPS puts in same-industry/sector competitors or market indices? At least reduce some crash risk, though I am not sure how you run your stock options compensation through BSM without a market to price against. Probably should figure what your VaR is for an x-sigma crash and try to get a hedge which will roughly balloon to that level under high vanna.