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Are you trying to imply that these people aren’t counterculture? Really difficult for me to name anyone who’s caused more impact / disruption than the list of names here.
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If whole top of Silicon Valley is "counterculture", that word has no meaning.

> Really difficult for me to name anyone who’s caused more impact / disruption than the list of names here.

And from that you make the conclusion they are "counterculture"? I don't think it means what you think it means.

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> a group whose values, norms, and behaviors actively oppose and reject those of mainstream society

Basically every name listed meets this definition

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Are you trying to imply that Jeff Bezos and Mark Zukerberg are counterculture in some way? What?
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Correct, but I wasn’t trying to imply it, I stated it outright.
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So anyone that creates a new business that is successful is inherently counter cultural?
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These people in fact are some of the principal figures dictating the dominant culture and status quo.
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In what way? The dominant culture hates them.
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No it doesn't. Fashionable people pretending to be counter-cultural love to talk about hating them, but look how many people are on Facebook, how many are using Amazon, how many are using Google products. Consider that "google" is now a verb and literally everyone knows what it means. The part of dominant culture is to show one's "independence" and "free-mindedness" by saying some words about how all those people are oh so awful - and then go and consume the products they make, exactly in the way the want you to use them, and pay a lot of money for it. That's no more "counter-culture" than a multi-millionaire Hollywood actor dressing in a six-figure dress and showing up at a six-figure-per-ticket gala to protest "the elites" is "counter-culture". It's just the elites' LARPing.
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Either of the mentioned was at one point of their career someone who would have been considered at least belonging to "counterculture".

Unfortunately, money and power corrupts, and lo and behold, one day you wake up to find you have become the very thing you once swore to destroy.

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Maybe, some of them were poor young iconoclasts some day. That's not when they joined the fashionable trend of Burning Man though. When they joined their trend, they were well into their power (or at least, in the case of somebody like Holmes, pretense of it). Because that's what is fashionable, of course, and they couldn't afford not to be part of "counter-culture" - it's so gauche not to be part of it!
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Power doesn't corrupt, it reveals.
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All of the people mentioned have been in millionaire to billionaire families since birth, so based on that alone I am not sure I work with the same definition of “counterculture” as you are.
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Millionaire is not some ultra privileged status in the United States, an upper middle class family with a paid off house in a somewhat decent area will have a net worth in the neighborhood of 1 million dollars.
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Number of millionaires in the US: 23,831,00.

Yet again, different idea of “privilege”, I guess?

https://en.wikipedia.org/wiki/List_of_countries_by_number_of...

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Maybe wisdom gives another perspective on the ideals we had in our youth?
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there's nothing wise about hoarding
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None of those people are your average citizen.

The idea that rich people are all right wing conformist republicans does not survive getting to know a few of them.

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They may not be right wing conformist republicans but they are certainly not opposed to any aspect of current power structures in any meaningful way (unless, perhaps, it is restraining them).
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Not sure how did you read "right wing conformist republicans" into my comment that had literally nothing about partisan politics.
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