Musical acts make $1 million+ per concert (if they're doing arenas), so they're not in the poor house.
Rogan has $100 million, so there's no need for him to do anything different. His ascension has been interesting. He's sort of done the McDonalds thing of being consistent. Not amazing, not perfect. Just consistent - grinding it out. He's been podcasting for 20+ years. And despite being gullible for conspiracy theories (even the really dumb ones), the one biggest thing he's had going for him was his lack of an ego. He's said countless times that he's an idiot, that he's an expert on nothing, and that no one should base their political decisions on what he says.
He has had experts in an incredible number of different fields on, talking for 2-3 hours, while asking questions and for clarifications just as any layperson would. THAT is what's drawn people in. He's not always up against a commercial break or arbitrarily ending the show at a set number of minutes, and it's allowed for conversations to occur that you can't find anywhere else. Not because he's particularly deep or knowledgeable, but because he's never been beholden to anyone. He ends the podcast when everything's been fleshed out, not because a focus group says an ideal podcast length is 92 minutes.
I can't tell you how many times I've been enjoying one of my other podcasts and they "need" to wrap it up.....because.....reasons? Because if you spoke about philosophy or college football or religion for 7 more minutes, the world would explode? All your listeners would complain? What? It's stupid.
Joe Rogan isn't great at anything except not being a slave to the clock. The mainstream everything can't handle that.