People seem to assume the fact you’ve managed to amass money to be a fact that vouches for you … like you cannot be inept / senseless / bad at managing money because, look at that, you’ve got money. Doesn’t matter if you inherited (and subsequently lost much of) a bigger load of money, managed to injure yourself in some stunningly original way that requires some company to fork over millions, tripped over your untied shoelaces and discovered the lost Civil War gold. You have money, so you’re awesome at life.
It makes me think of the towel in the Hitchhiker’s Guide series — encounter someone while you’re wandering and, if they’ve managed to keep track of something so trivial as their towel, then they’ve obviously got it together.