I get mixed emotions. Yes, companies that do 'bad things' ideally are corrected out of existence by the market. I never like to see anyone lose their jobs, because at some level the rank and file of the company is the blood coursing through its veins. And as Marissa Meyer and others have re-iterated over the last few months, companies don't do thing
people do things. So people who are getting things done and fighting the good fight, its always painful to see them go.
On the money thing though you really need to come to terms with the fact that there is way more random chance than there is earned riches in the tech business. For every person who got rich being the most brilliant mind on the problem at the right time, there are hundreds, if not thousands, of people who got rich just because who ever was sitting in the seat they happened to be sitting in also got rich. The folks who just happened to be at Sun when it founded, or HP, or Google, or FaceBook. Randomness, not skill, plays a huge role there. There was a guy at Sun whom I helped manage out of the organization, he landed a job at a start up that two months later got bought with a full vesting of everyone. He walked away with several million dollars. It took a lot of thinking about that series of events to let it sit in my head without pissing me off.
Different people exploit their opportunities differently. I know that if I both knew how, and could have, shorted stock I held but was locked up but worth 'millions' I would have. I would have said "That's enough for me, sell it all, and when it dribbles out via my acquisition contract timed unlock I'll hand over the shares." That would have made me 'evil' in the eyes of the shareholders who bought stock during that time (and later sued the company) but my motivation would have been quite pure (FU money is a good thing). But I don't think of myself as an evil guy, and generally am pretty nice.
Bottom line is people with large holdings in a startup will look to 'liquify' a chunk of that to diversify and allow them to activate the wealth 'ratchet' (that is where you solidify your position by converting equity into real goods). If the value of the company continues to grow nobody ever remembers, if the value plunges, they get the short end of it. But its mostly randomness at work.