> I think it's healthy to just let vesting mean you get to take it with you, period, no catch.

This sounds great in concept but in practice acquiring the shares is the taxable event. So if a company just gives you shares, that's the taxable event. And since you get taxed on the delta between your strike price and the "fair market value" (even though there isn't one), it would happen on the company's schedule, not your own.

If you extended the exercise window for N years, that would mitigate most of it because you could wait to execute until it's liquid. Or not execute at all if it goes under.

* I've been through two IPOs in the last couple years.. good planning shielded me from having major tax liabilities.