A life of having shit handed to you on a platter is poison
I'm going to disagree. It isn't that things were handed to him, but because he received everything because he was a piece of shit. He earned millions partially from his ability to ride his skateboard, but mainly from his ability to be a disgusting asshole to his family, friends, and strangers. He seems completely lost when being a disgusting asshole doesn't reward him with money, admiration, and a better life. He appears to only knows how to shit on those around him, while acting like a spoiled toddler.
And, I worry that this idea of having things handed to you is a bad thing is something that those of us who work for a living tell ourselves to make ourselves feel better. We pull on this myth that the things that make us miserable are really what make life meaningful. Reasonable challenge can be great, but suffering and struggling are not positives.
Leaning into the notion of hard work when we are just trying to tread water, reminds me of destitute people in Africa leaning into Western religion to save them. The guy who lives in luxury who is selling us the myth that hard work is what matters is the weaker cousin of the colonizer bringing Jesus's love to those that the colonizer is about to rob and steal from. The colonized pray to the myth brought to them by the person who came to exploit them, and we lean into our suffering is "real life" when someone else goes home to a nice warm house and doesn't deal with the stress of hard work accompanied by little reward.