Had one rich guy who fits your profile but the odd thing was although on the ground he was very domineering and confident, in the air he had very little confidence. With attempting to deal with him on the ground I just didn't let him get away with it, I couldn't knock him down a peg or two though, because of his lack of confidence in the air.
With teaching more experienced pilots from airlines I have generally not had many problems, they're usually very happy to be taught by someone less experienced than them in total hours, however, I did have a problem 747 Captain when I was first starting out, he was new to the club so needed a checkout and was refusing. I failed to convince him otherwise partly because he recognised my inexperience and realised he could dominate me, I ended up having to get the CFI to convince him, but even then the CFI had to do the checkout.