I think your past mentality is what a lot of people have still in the bay area. It seems that every person I meet at startups thinks that their stock is going to be worth significantly more than the strike price.
If a startup has a decent exit, it's usually that founders get a life changing amount of money and then employees get car changing amount of money. Even if my 50,000 shares sell at $10/piece... It's definitely not any better than what I would've received at Google/FB. And I'd be nearly guaranteed to get those shares at Big N and liquidate them vs low single digit chance at a startup. The expected value when it comes to stock compensation at startups, in my rough estimate, is maybe 10% of that of what you'd see at a Big N.
If a startup has a decent exit, it's usually that founders get a life changing amount of money and then employees get car changing amount of money. Even if my 50,000 shares sell at $10/piece... It's definitely not any better than what I would've received at Google/FB. And I'd be nearly guaranteed to get those shares at Big N and liquidate them vs low single digit chance at a startup. The expected value when it comes to stock compensation at startups, in my rough estimate, is maybe 10% of that of what you'd see at a Big N.