I love Jay Lenos garage! I think he has some cars with a value of close to 1 mil. Not to mention one of the best collections of vintage and rare motorcycles in the world.
I don't doubt that the money doesn't matter to him either, he is probably happier tinkering with an Arial Square Four, a 1930's Knuckelhead, or riding an Indian Chief. He would probably make a ton of money doing a special interest cable car program, I'd watch it.