I don't think he's a clown. He just has no clue when it comes to fashion - particularly youth clothing and choices. Look at him. Very little sense of adult fashion either.
Can't you just imagine him 20 years ago saying: "No. Nike. No No NO I hate the model. How can you possibly think you can sell sneakers at twice the price of my converse. It's just a fad. It won't last."
When it comes to picking trendy retail and who will win, I don't mind being on the other side from a Harvard/NY schlep who can't name three surfers or even one boarder other than Tony Hawk.