Of course it is. All things being equal, if you're still employed a year later your stock vests. In his situation he'd have to start negotiations about his equity. That's a huge difference.
I don't agree. If he's indispensable he'd have an easy time getting equity after a year. If he's underperforming he'll be let go in just under a year to avoid the cliff...
The biggest problem in his situation is there's not contract in place to keep the employer honest. There's nothing to prevent them denying they ever offered equity, nor to prevent them starting the clock on vesting at the time the option agreement is signed. "Here's a meager salary for now, and you'll have to trust us to do The Right Thing later."
The employee is the one getting the work done. And he's got to watch out for his bottom line like everyone else. If you're being promised equity without a written agreement, then take that into account- assume it's not even part of the equation and negotiate better pay or move on.
It's not strictly equal, and true, accelerated vesting is a factor.
Just attempting to make the point that one should not take too much comfort in any options package before he/she is over the cliff and unless he/she has seen the cap table.
