I realize I could have attempted to exercise sooner, but that isn't quite the point. The part that really bugs me is the fact that time is undervalued (or non-valued). If I have a high value asset, my time, that I contribute towards the success of a company, it's value goes severely underappreciated by management and the board. That's the problem. If person X puts in money, and person Y puts in time, the time is regarded as a non-asset. Now, you might be tempted to say, "but you got paid", and I did. But I put in far more time than would be required somewhere else. That is, I put in extra time, a non-fungible unrecoverable asset, into the company and had nothing to show for it. Asking for more payment (for the options) is the equivalent of asking me for more time, which I had given plenty of already.

I think this is a good point. If you're going to take options in lieu of part of your salary, they should for fairness be options on preferred shares, because you're effectively contributing cash.

Of course, nobody gives employees options on preferred shares.

So were you the only one working longer hours? And if you felt so undervalued, why didn't you ask for a raise at any point over those 8 years? Perhaps your work ethic is why you were given the options in the first place?

It seems like you're whining about something that you had complete control over, and chose not to exercise.

people make companies and the rules. you are a person and agreed to this and acted as if you agreed. you took a bet and it didnt come out financially the way you want. you probably learned alot about startups and what works and doesnt tho.

Well, yeah, the only person I was angry with was myself. The rest of my emotions at the time were mostly of frustration and sadness with a system that undervalues an asset I had invested (my time above and beyond).

A lot of times a company will have a decent idea of what their exit is, based on how much money is in their market, or how much similar companies have sold for. When that's the case, you need to ask.

1/3% (and that's generous) of a potentially $1B dollar company might seem like a lot, but after 10 years of dilution how much will you really have left? If your options dilute by 1/4 (also generous), you've made about an extra $80k a year, and that's not even with taxes subtracted. And don't forget the likely higher salary, raises, bonuses, stock grants, and medical care you get at a big 4 company.

It's possible that you can be be assured to make no extra money working for a startup, even with all the extra risk, depending on how those factors play out.

I think the point is employees under estimate the risk involved. I could make a start up that pays people in literal lottery tickets but I'd be unable to hire anyone because prospective employees can easily see it's a bad deal. Not the case for start ups.

I was thinking yes, but then no?! I bet you could hire a bunch of people with lottery tickets!