[dmur]

>If he's willing to do that, then he'll have to exercise what he already has vested.

Not necessarily. It depends on the terms of his or her options grant. Many companies give employees a 10 year exercise period after they leave (advocated by Sam Altman: http://blog.samaltman.com/employee-equity).

[amirmc]

> "Many companies give employees a 10 year exercise period after they leave"

I suspect many companies don't do this, as there'd be no need to advocate for it otherwise.

[jayp]

A 10-year exercise window has to be extremely rare to the order of non-existing in SV startups. Maybe it's picking up stream since the article was written and I am not aware of it. Can an employee vouch for his/her employer (company) that does this? Do more recent YC companies do this?

In fact, even Quora hadn't actually implemented a 10-year exercisable window by the time (or right before the time) Sam's article was written: see comment at https://news.ycombinator.com/item?id=7610668. Note that the article simply mentions it as an idea; not as an ongoing implementation. I wonder if it is now actually implemented at Quora.

[idunno246]

Except after 90 days ISO become NSO, so you lose tax benfits. But maybe he 83b'd them and already purchased as employee #2