"It certainly would've been better financially, though honestly, the difference is "set for life" vs. "set for a long time", so I'm not certain it would make a

"It certainly would've been better financially, though honestly, the difference is "set for life" vs. "set for a long time", so I'm not certain it would make a material difference in my life now" Let's not forget that DropBox hasn't exited yet, and in fact may be in a very tricky position. As much as it's fun to look at "I'd have had 0.75% of $10bn, that's $75m!", it's rather unlikely that you'd see that money. Maybe they can pull it off, but it's also possible that they are in a bit of a tight spot where they're over-valued, which can absolutely ruinous to employee options. They have to prove to the market that they're much more valuable than Box, which has a head start on them in that regard. I'm not sure I'd view it as that clear-cut. If you walked away from your previous company with a life-changing amount of money, there's a very solid chance you were better off there than at DropBox, purely from a financial perspective. I'm not trying to be a jackass, I'm just trying to say that they haven't exited yet, and you can't really compare!