Regarding "thrive or die", the usual case is neither. The usual case is "zombie", continuing along, surviving, but failing to really get ahead. In many ways it'

Regarding "thrive or die", the usual case is neither. The usual case is "zombie", continuing along, surviving, but failing to really get ahead. In many ways it's worse than thriving or dying, since at least dying frees you up to get a fresh crack at things. With a company woodpile of $1M to burn and a stake that's currently worth $300k in Powerball tickets (eventually to be $1.2M in Powerball tickets if you keep working there), you could be doing worse. But you're not doing that well. Consider getting a job at a BigCo in the bay from here on out. $185k + stock options that you can actually turn into cash seems very possible. Your current company with only $1M in the pile is not going to be able to move your needle all that far from the vow of poverty you took, not without raising more money or bringing in substantial revenue. In many ways, I would argue it's already failed if you're not in the chips after a year. You've met your cliff, so you can take the money and run, so if somehow the company makes a $100B valuation, keeping your 0.5% on top of a decent salary elsewhere seems substantially less risky than grinding poverty to raise the number past 1%. It's not about what's "fair", it's about what's possible. Your boss will tell you his hands are tied when it comes to bumping you into the six figures. If you don't want to "break up the band", and you want to "see things through", and you can tolerate continued poverty, then I submit to you you don't need to ask for a pay increase. Otherwise, it's not your boss you should be asking, but a competing company. Silicon Valley VC's aren't the only ones selling dollar bills for fifty cents.