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Dealing with a contradiction in a character

I have this one character that supposed to represent two things: Old Money coming with a prestigious name and the self-made man who reach success all by himself. As you can see, there is a contradiction there, so I came with this idea to keep both these things:-His family was rich for generations but when he took over the family business, their company reached a level of success never seemed before.I fear this idea to be far-fetched, the reader might perceive it as “Okay, so he was a rich guy who just sat down and gained a lot of money after his parents died, now he’s even richer because his parents provided to him the right education to use his money, where is the merit?”. I have two main characters, they came from a lower-middle-class and their opinion of this character is a key element for this story, one finds him to be just another rich asshole who was Lucky enough to be born in the right family, the other admires him and wants to be just like him because he perceives him to be a self-made man just like he dreams to become.This also creates another problem, his son supposed to be a reckless playboy with no idea how to handle money whose ways ended up being the failure of his father. In my earlier versions, the father was truly a self-made man coming from a regular middle-class family, so would make sense for him to be too busy on his job and not teaching well his son but he comes from a traditional aristocratic-ish family that for generations thought their children how to administrate business his son being a stupid playboy would come as unlikely.Success, richness, and realizations are central themes in my story so I need to handle them well and I’m unsure about this point of the story, any advice?