Nah, I didn't do it like that. I did it like how I used to do it on PS3.I signed him up as a "secondary" to my account on http://www.playstation.com/en-us/home/ did you do the same @GoldenGlove ? that could be why it's not working.
He downloaded everything under my account. Switched over to his account, and it wouldn't let him play shyt because it said that the account trying to play the DLC wasn't the primary account.
I have to investigate this further