The reason that many wealthy people stay that way is thanks to them being pretty darn stingy. It's always the friend on six figures who is sending the $2 Venmo requests. While nobody likes a freeloader, the irony is that those who don't need to do this can be the most audacious when it comes to taking financial liberties.
A recent and depressing example of this has been found on r/AmItheAsshole, in which a wife complains about the grocery habits of her husband. Clarifying that they have a combined household income of over $200,000 a year, she was horrified to realize that her partner had been regularly using food banks to cut down on their expenses.
Explaining that she had gone to stay with her brother after the shocking revelation, she took to Reddit to ask if she had overreacted. Needless to say, other people were not impressed at her husband's unbelievably selfish actions.