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!
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.
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.