In my experience it really has not much to do with who the owner is vs how hard someone is willing to work at it and what their attitude is. I'm pretty sure that you could point to many really good pilots that were not "born into it" and some real sketchy ones that were....
Does someone have to be willing to "put up with mistakes?" Sure but that's a lot more likely to happen if you have a learning attitude and a willingness to admit mistakes. Something that in my experience is very hard for a lot of pilots to do.
Why? Well maybe because pilots have a tendency to fight gravity. It's part of their nature.