People that grew up in money also don't have much of a notion of the true meaning of it. They haven't had the experience of not having it, and can sometimes not even comprehend being given to. So they don't know what it feels like to have something out of their reach, but they do know they can easily resolve that situation. They also don't understand the vulnerability of the self-esteem of those receiving.

Further to that, they're used to doing the giving (paying) and spending, and it not really making a dent either way.

My boyfriend is in this boat. I earn well, I don't need his money, but it is the easiest gesture he can possibly make and it is easy for him. For him, that is the most fluent, regular way of showing love or friendship to someone. Even though me paying for our dinner is a piss in the ocean to him and even a bit of a slight to his ego, I'll insist upon it on birthdays and other occasions like that. Luckily, he understands gestures, even if dollars and cents don't have much meaning to him.