There comes a time in every successful rapper's life when he has to ask himself one of the most important questions of his career: Should I start a clothing line? Some have done it successfully (Jay-Z and 50 Cent come to mind), while others haven't had such good fortune

For Drake and his brand October's Very Own (bettern known as just OVO), it's more complicated than just getting his gear into Macy's and making bank. We had an opportunity to pick his brain for our cover story, and here's what he has to say about the future of his brand. 

Interview by Damien Scott (@thisisdscott)

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