One big question I didn't discuss is how to evaluate the prospects of the employing company, and I didn't discuss it because I didn't come up with good advice.

One big question I didn't discuss is how to evaluate the prospects of the employing company, and I didn't discuss it because I didn't come up with good advice. Companies differ tremendously. In particular, I personally was spoiled working for a company where the founders are very good negotiators, apparently even better ones than the various i-bankers they dealt with. For instance, they never took any VC money, presumably under the assumption that VCs might decide to gut the company if it doesn't become profitable in a time frame which for them seemed too short. They also made sure to raise tons of money years and years before running out of already-raised money; the conventional wisdom is you're not a bank and you should only raise capital when you absolutely need it, you shouldn't have stashes of idle cash, but the problem with this approach is that you raise money when you're desperate and this diminishes your bargaining power tremendously. Raising money long before it's really needed resulted in really good deals for them. I was also spoiled working for a company with a simple business model and pretty predictable revenues so it wasn't that hard to put a conservative lower bound on its future value. Anyway, I only addressed the really wrong arguments that I heard a lot, that after a late-stage investor gets on board the stock "can't possibly rise any more" (meaning, the late-stage investor is at best going to not lose money but can't possibly make any, so they're much dumber than you are); and, "even if it rises, it'll just rise a little" (which neglects the arithmetic of how your capital gain is calculated.) Your argument is different and I confess that I don't have any stats to either support or refute it.