Rich kids can afford 'responsibility' because they have money to pay for their mistakes. Poor kids don't.
Best way to be prepared for success? Be born to a rich and well connected family.
In my perception many of the rich kids lack the drive to work as hard as you need to, to become a successful entrepreneur, instead opting for a safer route. Granted, if you are from a really poor background and live in the US without much of a social safety net, I could see how that could hamper your prospects, but that's hardly a problem where I'm from.
If you're surrounded by entrepreneurs (such as SV) it's not a representative sample. Even being born "middle class" is a narrow slice of humanity today, much less everyone ever born.
Of all the people rich today -- or ever -- how many started middle or lower class?
How many came to America with nothing and died, barely survived, went to jail, got deported, peaked at lower middle class, etc.?
If I know a lot of plane crash survivors I still would not recommend getting on an unsafe plane. (I actually only know one crash survivor and would not get on a small plane unless it's a life or death emergency.)
Which is funny, since now the descendants of some lucky people get the opportunity to take lots of chances and say "look how hard work pays off — I made my own luck!"
Though that's a pretty simplistic take; I feel like hard work really does pay off, broadly speaking, but also luck plays a (much) bigger role than most give it credit.
Those born wealthy can often buy so many tickets it's virtually guaranteed they'll stumble into something that works, at least once.
No one is saying people don't have to at least lift a finger to try. Just that birth luck affords so many other opportunities that the advice of outliers and the born comfortable isn't transferable.