I heard most of the time the skater gets a few different shoes to choose from, he chooses the one he likes best, and they stitch his name into it. I bet a lot of time they probably just tell them what they want (vulc/cup sole, leather/suede/synthetic, techy/basic, whatever) and somebody else designs something based on what the guy wants. Sometimes pros design it themselves, but in reality, if we let every dude who was good on a skateboard design his own shoe from scratch, there would be a lot of crap shoes out there, they aren't designers.