If Scott wasn't with Kourtney he'd probably be in jail. I can totally see him taking part in ponzi schemes and other fraud activity to make "easy" money. He sure as hell wouldn't be working a normal job, he's as lazy as they come. He lucked out with Kourt.
LOL. I can see that. I also see him as Patrick Bateman from American Psycho - without the serial killer aspect, but definitely with his love of fine things etc etc
And now I can't get the image of Lord Dick (<typo and it stays) singing "It's Hip to be Square" out of my head.