Steve Jobs alone is more of a counter culture figure, with the ashram in India, and the drug use, and the whole garage story.

Zuckerberg was a kid from freakin' Harvard and Phillips Exeter. I think the Harvard thing alone disqualifies him from being a counter cultural figure, especially since he has always seemed squeaky clean and fairly intelligent.

As far as the nerds "winning" -- I thought that was the way of the world. Napoleon wasn't some giant, neither was Bill Gates. The idea that the jock's best years are in high school is a pretty well-known trope at this point, often used to comedic effect in movies like Revenge of the Nerds -- or TV shows like Married with Children.

Well-off kids doing well for themselves is hardly unusual or counter cultural -- it's more like that's what we would expect with the advantages afforded to them.