Jay-Z
Jay-Z's been making boardroom moves ever since he founded Roc-A-Fella Records with Damon Dash and Kareem "Biggs" Burke to put out his 1996 debut, Reasonable Doubt, after the major labels rejected him. The Roc went on to launch Kanye West, Cam'ron, Beanie Sigel and a successful clothing brand, and Jay eventually became president of Def Jam before starting his new Roc Nation imprint.
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