Made his money early being a mouthpiece for slackers, which means he used a network to get noticed from a relatively young age.
If he came from a working class family, he obviously doesn't remember the work it took for his parents and neighbors to get where they were, and how lucky he was to get where he is.
Doesn't care about anything, doesn't need to care about anything, has enough money banked to do whatever he wants, and assistants to play mommy and daddy, taking care of the hard or expensive stuff for him so he never has to count his change two days before payday -
Unlike all his followers - the raised by TV dude-bros and gals who float through Millennial or Gen Z circles, wondering why they can't just have a car or a cool apartment, or be able to collect all the toys, instead of paying attention to what's actually going on or being curious about how the world works, or why they and any respect for their potential are being passed by "society" in general.
It's an outlook that's all so shallow, and wastes productive like constantly watching streams or playing video game instead of examining a puzzle or finishing a project.
Totally dependent on the system they operate in; they're basically NPCs and they're willing to sit back and live that way.
They've grown up with the expectation that if things get too hard, the can just switch the channel or hit reset - unfortunately, that's something only rich dudes can do anymore.
Looking forward, if society collapsed, there's nothing "there" Rogan and his dude bros can fall back on. Except for being relatively strong back
S to be used by whichever warlord or regional dictator is clinging to power until he wears out.
Rogan's not going to be in charge of "Bartertown", he doesn't have the imagination or smarts to make it to the to the top. At best, he'll will end up a disposable work gang boss due to the ability to be recognized by lemming bros