Very tiny tips and very, very huge icebergs.
I challenge you to think of ways that this spoilt kid can spend his money that will realistically cause him to go bankrupt. Yes, he could buy his dog 1500 Learjets, but unless he bought them all at once he could still buy many more. (Indeed, he could buy 150 Learjets per year for 30 years and still be pretty damn rich.)
Yes, he could buy many private islands and armies.
2 Apple watches, or 1000 Apple watches, are not remotely a significant “tip of the iceberg” in any meaningful sense.
Yes, that is absolutely the case. Bankrupcy is many, many times more likely to happen because of (a) enemies in the government, or (b) pitchforks from the peasents then it ever is due to rick-kid spending.