I am not particularly impressed with people who, by virtue of being born into money, spend years of their lives engaged in various unproductive pursuits.
I do find it interesting that someone named johngalt would be impressed by someone living the benefits of unearned wealth. Perhaps you should have adopted a more appropriate username. Were philiprearden and jamestaggart taken?
While it's not what I would choose for my kids, the money isn't uneared. His parents or ancestors earned it and spending it on him is what they want to do. It's not like he took it from them by force? FYI, objectivists are also allowed to buy birthday presents for their toddlers.
Do I find the idea of traveling the world and surfing interesting? Yes I do. Would I consider that adequate job experience? Not at all.
Remove the chip from your shoulder. Someone who wasn't you was able to do something fun. Don't be jealous of that.