It's ok not to spend time and money on looks. No matter how much money you have. There's no obligation to look good for anyone. The way he looks is not the problem with him.
He owns the company, he can represent it anyway he wants. If he owes anything to his employees, it's fair wage (I have no idea how fairly or not he pays).
He was going for Roman Emperor with the last one, but he neglected to consider the shape of his head. I really don't know what haircut would look good with his strangely shaped face/head.
He is rocking that sun bed tan line(the white eyes and live over the nose), which to me makes it look like he never actually does go outside. And does seem to have a bit of an orange tinge to him as well.