Again, hed still be a worker though. He still wouldnt be the boss. He cant turn around and start the Anderson Cooper network.... but thats pretty much what you said Envy should do. In some businesses, but ESPECIALLY media, access to a big platform (with the reach, ad money, infrastructure) etc is worth a lot more materially than having the ability to say "I'm a boss". In my opinion, if striking out on your own isn't a clear path to more money, there is no value in it.
Like I keep asking though, what lessons has your pops taught you that a man working at a job couldn't? Workers don't have to work hard? Workers don't have to have integrity? Your pops did well for himself, struck out on his own. That's good. But that had no bearing on his ability to teach you well. He would have taught you well working a job. The way a man makes his money does not define his character.