I like that saying but those are all entrepreneurs right? Where are all the philosopher wannabe billionares? From my experience they seem pretty happy in relatively low paying professor jobs.
I doubt that anyone could categorize the manosphere phenomenon as philosophy. Without empathy you can't really have philosophy. Or, at least not the kind that you can take seriously.
nassim taleb is primarily a philosopher who pretends to be a hedge fund guy, jordan peterson, robert kiyosaki, tim ferriss maybe, sam bankman fried, the tech lead yt
archetype is people who sell their success as a model for you to follow while having none themselves, wrapped up as some kind of philosophical position, so they can make money
lots of self help authors, failed vc funds, podcasts
I don't think Peterson is a philosopher or an entrepreneur. Does debating college kids make you a philosopher now? Is that the bar? At least mention Žižek. He's an actual, present day philosopher.