That goes to the heart of the most frequent cause of trouble between shareholders: badly aligned interests. Even so, if you're looking at the stock as a lottery ticket and the company does take off you're in a good position to make a fair amount of money, you just shouldn't count on that. But if you're going to play you might as well play for stakes that are worth it. Each to his own, I think a big part of the 'compensation' in being part of any start-up is that you get ring side seat on how that whole thing works and you can - if you are not just heads down coding - get some very valuable contacts out of it.

This can turn out to be worth more than either the stock or your salary but that's a long game and one with even less guarantees.

Still, I'm pretty sure that very few people that were on board with one of the bigger SV successes of the last 2 decades are going to complain about their pay-day, whereas for everybody whose company did not make it it hardly matters how much stock they got. And that's really where these founders miss the boat: they should be happy to share a sizable chunk of what is essentially worth nothing. They are essentially already busy with their exits when they should be building a company and that alone is a good reason to avoid those companies.