Damon Dash’s mother used to tell him, “No one is smarter than you.” It was that mantra that drove Dash to insist on a level of control and a degree of diversification that would surpass that of even Russell Simmons, and propel the career and fortunes of his Roc-A-Fella partner and number one artist, Shawn “Jay-Z” Carter. Dash walked out of meetings with record executives who disrespected or lowballed him. He fired lawyers who failed him. He’d spend his own money rather than settle for being shortchanged by a partner.

Within months of the release of Jay-Z’s first album, Reasonable Doubt, Dash had scored a multi-million dollar joint venture agreement with Def Jam. And even after the deal was done, Dash raged at the slightest slight or the faintest hint of being eclipsed by the larger label. Spite was Dash’s fuel. When the clothing brand Iceberg Jeans told him that they weren’t interested in awarding Jay-Z an endorsement deal, Dash told them that he would start his own clothing company and put them out of business.The threat didn’t turn out to be so far from the truth.

Rocawear, founded in 1999, became one of a few ascendant “urban” clothing brands in the first decade of the 21st Century. But Dash, typically, wanted more, casting Kevin Bacon and Naomi Campbell to appear in Rocawear ads, pushing Rocawear as a mainstream, global brand. Dash applied that same sense of entitlement to other consumer products. When he tired of holding bottles of Belvedere in his videos, he created his own brand, Armadale. Weary of seeking the endorsement of corporate brands, he bought them instead, licensing the PRO-Keds mark from Stride Rite in 2004.

As a result, Dash created a new paradigm for hip-hop dominance. Hip-hop was no longer a beggar at the door of corporate America. It was a player, worthy of a seat at the table. Dash probably would have tried to buy the table, too, had his partnership with Jay-Z not unraveled.