What these guys said about marketing is right. THe best way for this gy to succeed at thits (and its possible) is to make himself a niche. I'm going to say viral marketing is going to be his weapon. That and capture a small area.
Here's his plan,
He needs to a few distintice shirts. Not a whole brand just yet, just a few shirts, that are distinct identifiable as his label. THEN, find some type of group/culture element, contained within one area, and do whatever it takes to get that one group to adopt his shit.
Generic example, say a local skat scene in seattle. Thats it. All he does for a year or two is get his shirts circulating in that community. Eventually it will become this cool, inside trend with the seattle skaters. Then, via word of of mouth, social networking, etc his shit will be "discovered" as "this cool underground brand that is really big with all these seattle skaters". Then, the label starts to get heard of around the rest of the country, and its already got itself some (engineered and fabricated) street cred. 6 months or so later, he can start introducing a broad line of designs, which will be able to ride the name recognition.
