Sean Combs and Sean John – The notoriously entrepreneurial artist formerly known as Puff Daddy, P. Diddy and just Diddy made his name(s) producing Top 40 smash hits with Notorious B.I.G., but he made his money manufacturing menswear. Launched in 1998, Diddy’s Sean John is an award-winning clothing company that’s helped Combs become the richest rapper in the world. Along with his record business and stake in Ciroc vodka, Sean John has helped Combs build a $475 million fortune. “My brand is rocket fuel. It would take this brand 10 years to get to where I can take it in one year,†Combs told The New York Times in 2008. “I’ve gotten to the point where I don’t want to do just endorsements. I want ownership.â€
Jay-Z and Rocawear – Trailing Combs just slightly, the Brooklyn native is worth about $450 million, almost half of which can be traced back to Jay-Z’s fashion line Rocawear. Jay-Z founded the company in 1999 with his Roc-a-fella Records co-founder Damon Dash and after several profitable years sold the brand $204 million in 2007, just a couple of months after an investigation found dog’s hair in Rocawear faux fur coats. In the meantime, Jay-Z has built out his empire with ownership stakes in the 40/40 nightclub chain, Carol’s Daughter beauty products, and J Hotels, a real estate venture. “My brands are an extension of me,†Jay-Z said in a 2009 interview. “They’re close to me. It’s not like running GM, where there’s no emotional attachment.â€
