> Once again we’re talking about employee #2, exercising early would not have been that expensive!
Exercising early almost certainly would have cost hundreds of thousands of dollars. For employee #2 of a startup, you’re almost certainly already working for mostly equity and not salary.
You are high as a kite if you think it’s reasonable to dump large sums of money into a five-person company while getting paid peanuts in return.
A -EV investment like early-stage startup equity is still -EV for every incremental dollar spent. Paying upfront for equity whose terms can be rewritten out from under you with zero input is not smart from any angle.
You’re basically criticizing the guy for not having perfect foresight, when the real issue is that startup equity is trivially manipulable by upper-level management. It’s a carrot they can dangle in front of people while only rarely having to pay even a fraction of what was promised in the rare event of a profitable exit.
Exercising early almost certainly would have cost hundreds of thousands of dollars. For employee #2 of a startup, you’re almost certainly already working for mostly equity and not salary.
You are high as a kite if you think it’s reasonable to dump large sums of money into a five-person company while getting paid peanuts in return.