From 1999 Cover Subjects: 3 Hip-Hop Business Leaders and Where They Are Now

Damon Dash

Estimated Net Worth: $2 million

This well-known American entrepreneur is Jay-Z’s former business partner and manager. In 1999, he organized one of Jay-Z’s tours, raking in $19 million. Dash dated R&B singer Aaliyah until her tragic death in a plane crash in 2001. Four years later, Jay bought Dash out of his stake at Rocawear. Today, the hip-hop mogul is working on the introduction of a new clothing line called CEO Clothing.