More Than "Rap or Go to the League": Top Hip-Hop Artists and Basketball Players Who Became Entrepreneurs

2 Chainz’ new album “Rap or Go to the League” references the stereotypical aspirations of young black men who grow up in underserved areas. But throughout the album, he pokes holes in those stereotypes. He shows alternate paths and preaches the value of independence.

Is 2 Chainz an astute cultural critic? He might be.

What we know for sure is that these are not the only two paths to success for minorities in America. Successful entrepreneurs show young people another way to freedom and security.

The ranks of these artists entrepreneurs are filled with top hip hop artists and basketball players. Even celebrities have an entrepreneurial spirit.

We found a handful of rappers and ball players who demonstrate excellence in their professions and business. It’s possible to do both and they offer a lot of inspiration. Read on to find your new hero.

Top Hip Hop Artists and Basketball Players with Entrepreneurial Careers

Most of these people you know. It would be hard to find famous athletes and entertainers who had slipped under your radar. However, the way they invested their money may surprise you.

See for yourself.


This one is too obvious. Biggie’s former running mate has worn many hats: NBA team owner (the New Jersey and the Brooklyn Nets), entertainment agency founder (Roc Nation), club owner (40/40 Club), and champagne maker (Armand de Brignac’s Ace of Spades).

His most impressive business partnership might be his marriage. Together, he and Beyonce have a net worth of more than one billion dollars.

Michael Jordan

Speaking of a billion dollars, Air Jordan was one of the first athletes to become a billionaire.

He was synonymous with sponsorships during his playing years, thanks to his partnerships with Nike, McDonald’s, Coke, and Gatorade. After he retired, he poured a lot of that money back into basketball, thanks to his investment as the chairman and majority stakeholder of the Charlotte Hornets.


Usher isn’t just an entrepreneur. He is a philanthropist. His New Look charity uses education and real-world experience to help young people achieve their dreams.

He also helped a very famous young man achieve his dreams through his record label Raymond Braun Media Group. That young man? Justin Bieber.

Helping to launch the career of Justin Bieber might be the shrewdest financial move anyone on this list will ever make.

Chauncey Billups

This one is our favorite. The former Detroit Piston used some of the money he made during his 17 seasons in the NBA to go into restaurant franchising.

True to his nickname, “Mr. Big Shot,” Chauncey did not go small with his investment. He and another former basketball player, Junior Bridgeman, purchased 30 Wendy’s franchises.

Make That Money

Top hip hop artists and basketball players can represent distant dreams, but they still have the power to inspire us. We hope the way these celebrities branched out inspires you.

If you want even more entrepreneurial inspiration, check out our list of black businesses succeeding in 2019.

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