I got this backwards, as do most founders.
We think “being vested” protects us from VCs. Yes, there can be some corner cases where that is true, I guess. Maybe. Some times.
But what vesting really does is protect the most committed founders from the least committed ones.
Most startups I’ve worked with, one of the cofounders doesn’t work out. The usual reason is he or she isn’t just committed as the others. Startups are hard.
And this less committed founder often leaves just when it’s getting good. And often walks out the door with way too much stock.
The last thing you want, just as you are finally getting paying customers, just as it’s finally working … is the 2 co-founders doing the real work each owning say 25%. And the one cofounder that checked out a while ago owning another 20%. Just think of who you could hire, and what you could do with that 20%. You could hire 20 great VPs with that. 40 great directors. You could redistribute it to so many folks killing themselves to make it happen for you.
That will eat at you for years to come.
Longer vesting, longer cliffs, protect the founders going long. The real founders.
The cofounders that quit early should have good equity positions — be fair. But they should have nothing remotely like the ones that stay on and do the heavy lifting.