In the December 1999 issue of Black Enterprise, these three hip-hop moguls were featured as leaders in the business of hip-hop. When rap music exploded, new fortunes and businesses emerged. Now, almost 20 years later, these music executives still have some of the best reputations and most impressive resumes in the industry. Check out where they are now and the successes they’ve seen:

 

 

P. Diddy is a household name and has been for quite some time now. In 1994, Black Enterprise listed him as one of the Top 50 Entertainment Power Brokers. Five years later, the rapper appeared in BE‘s December issue. He became recognizable and infamous almost instantly. Today, he is involved in multiple business ventures, including his Sean John clothing line. He also owns the television network REVOLT, which launched last year.

 

 

In the late 90s, Master P’s first single Mr. Ice Cream Man, started the legend’s successful career journey. The star does more than just produce records and albums; he has also been featured in numerous television shows and DVD films. An extremely successful entrepreneur, he has invested in jewelry lines, sports management, telecommunications, car rims, and many other ventures.

 

 

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.