[kasey_junk]

I'd be surprised if he has any "equity". He may have options, but that is a significantly different thing. Most onerously of course is that if he leaves he will likely have to shell out actual cash on a lottery ticket. Who knows if he can afford to do this, or if it makes sense to do this.

That is a long way of saying, under almost any reasonable scenario, whether he has significant options (vested or no) should not be the determining factor on if he should stay.

He should stay if it he enjoys the job, they are compensating him enough in real compensation to overcome his lack of enjoyment, or he doesn't have other job opportunities.

I will say, as a long term employee (though to be fair, it's not that long term) he should have the ability to more forcefully outline what he wants to continue with the company. If he doesn't, either he's fooling himself about his real value, or he is doing a poor job communicating it to the company. In either case, it's his issue.