It's easy to look back and say, you're filthy rich now so you aren't actually taking risks, but taking risks is how he got there.
Having said that, I'm going through a stage in my life where I am getting to see the real character of people in terms of their risk appetite. Everybody wants to be an entrepreneur but when it really comes to doing it people chicken out. May be it's my circle but again that's my experience.
Also his music is pretty derivative if you've heard the music he is 'biting' or 'paying homage to' or what have you. I'd hesitate to call it pushing boundries as much as it is introducing it into the pop music lexicon.
Also people like The Kardashians despite their antics does that make them good... What is it they do again?
Lots of artists didn't 'go all gangsta' to make it. He isn't the first or the last.
The Blueprint being one of the greatest hip hop albums ever made is also highly debatable.
Claiming that soul beats weren't a thing in 2000 hip-hop is silly. Released in '99: Mos Def's Black on Both Sides, the Roots' Things Fall Apart. Hip hop started with soul beats, and soul has always been a part of hip-hop.
Edit: Removed part of comment that may have sounded overly negative.
He stresses that the most important thing to him is actually having ideas and sharing them with the world. He says this over and over again, and I can't help but believe him.
> The risk for me would be in not taking one — that's the only thing that's really risky for me.
His risk is sort of a philosophical/existential risk. Not what many would consider an 'actual' risk to himself. This really does seem to be a function of the fact that he is rich and a celebrity.
Kanye's very fortunate that "having ideas" are "the only thing that's really risky for me."
Personally I don't find a lot of value in his "ideas" nor do I agree that he's risking very much. For all his nonsense about liberation from evil, he seems hellbent on integrating himself with the fashion world.
Edit: Wikipedia says, "middle class" and the college he dropped out of was an art school so it isn't like he was giving up a sure thing to take a course that was more risky.
Knowing what college professor's salaries are like, "at least upper middle class" is way optimistic, though "probably solidly middle class" is likely.
I don't buy the premise that you need to be poor to have an appreciation of risk. Risk isn't just financial, there is also career and personal risk. Think of all the well-off kids who didn't follow in their fathers footsteps or what their parents wanted and pursued their own dreams, at the risk of being alienated, disowned etc.
The interesting thing though about most successful rappers is that, while almost all of them come from poverty, they tend to achieve success early in life such that by the time they hit middle age they've been rich longer than they've been poor (Nas notes this in one of his songs)...
A guy like Jay-Z talking about hardship increasingly sounds out of touch :)