My Dad was a bit like that.
He made his money, was a master of locking himself in with managerial style and software, and would get these ironclad contracts. He ran things very well, to the point where the business would rely solely on him to stay running. He also rented out properties on the side. By all accounts, he's led a life that I wish that I had.
He initially wanted to see more "him" in me, but honestly, I couldn't deal with the amount of legalities and backstabbing that he dealt with. With aside from one or two of his right-hand men, he pushed away everyone as a potential backstabber. He was very lonely and miserable when we lived together.
He's happily retired now, in a lovely house with a beautiful new family. He'd say that it was all worth it.