Sounds like the Monty Hall problem :) keep your door or switch. I'd say the ones who left were wiser ex-ante
I would be shocked if more than 10% of those recent grads who were working at Microsoft in 2001 and stayed in the industry anywhere are not now millionaires. (It's not that high nor noteworthy of a hurdle for our industry.)
You can look at this from many directions. Did the natural hustlers hustle their way to Google, while the naturally complacent stayed put? Did the Googlers just go there because that's where their friends went, or because they thought it was cool? Did the Mountain View people catch the fever after the fact, and become hustlers, while the Redmond people absorbed the relatively relaxed culture there? Did everyone just go where they thought was best and then it turned out one of those places was saturated in money?