There are two types of options, NSO and ISO. You want ISO as an employee because it's better for taxes, but that has a 90-day exercise window set by the IRS. You can push for yourself paying higher taxes in exchange for more flexibility, but it's a tradeoff.
Zach Holman one of the first github employees didn't get to exercise any of his options for the aforementioned reasons. When they tell you to throw your life away to believe in the vision, nobody tells that 24 y/o to get a lawyer to understand what that actually means.
He compiled a list of startups with sane exercise windows:
At the bottom of that link: “It's worth noting that Andreessen Horowitz has come out in strong favor of the 90 day window. If you feel strongly about extended exercise windows, it might be worth considering whether a16z portfolio companies are a good fit for you.” with a link to https://a16z.com/2016/06/23/options-timing/
The a16z link is astonishingly self-serving. Their top line solution was: “One existing solution to the ‘dead equity’ problem has been — and still can be — to make exceptions where appropriate for certain exiting employees. In fact, employers make exceptions all the time for certain employees, depending on their contribution to the company, critical skill set, and so on.” Riiiiiiight - asking nicely for a handout when you are quitting is a great strategy!!
And I would love to know how they come to this conclusion “In our model, we estimate that moving from the current 90-day window to a 10-year window will cost the average remaining employee as much as 80% in incremental dilution.” - just, wow.
https://carta.com/blog/pte-90-day-window/