Natural Born Hustlers: Top 5 Rapper CEOs

The rap game is filled with natural born hustlers, that much is undeniable. It is truly astonishing, looking at how so many MCs, since the inception of the genre itself, have successfully used hip-hop as a platform to become titans of multiple industries. Even though Jay Z (spoiler alert: he’s on this list) was the one who coined the phrase “I’m not a businessman. I’m a business, man,” he has not been the only rapper to make it a reality. With Hov dipping his feet into the pot of musical streaming services with TIDAL and Snoop Dogg lobbying to be the CEO of Twitter (honestly, not a bad choice), rappers are finding new and exciting ways to lead businesses that are increasingly accessible to their audiences.

In the wake of Forbes' highest-paid celebrities list, on which a few of the names on this list land (but not all), we take a look at five rappers who turned into CEOs.

If Tech N9ne's music isn't enough to convince you he's the undisputed king of underground Hip Hop, then perhaps his bank account will do the trick. Fresh off his impressive 2015 release Special Effects, Tech N9ne has made a name for himself with his longevity. Thanks largely in part to his rabid, cultish fan-base, the Kansas City spitta has developed his brand into one that can sustain a profitable 100-date-a-year tour schedule. Known for popping out albums and merch/swag that makes the 'Hood Go Crazy,' N9ne's lucrativeness has gotten him covered by Forbes and also made him a certifiable multi-millionaire. 

Let’s get this one out of the way since I already spoiled it, why don’t we?

Jay Z’s track record is impeccable, and unlike Sean Combs, Shawn Carter has been able to keep his nose (and track record) relatively clean while his millions. Creating a foundation for himself with Roc-A-Fella records, Jay-Z went on to dominate early 2000’s fashion with Rocawear. That wasn’t enough for Jay, though-- he needed more (and I don’t mean Beyonce)-- because he also herded some of the world’s elite sports superstars to be signed to the agency he founded - Roc Nation Sports. Most recently, he took on the very ambitious endeavor of TIDAL, a streaming service which aims to compete with platforms like Spotify and (even more recently) Apple Music.

Despite his seeming inability to keep his name out of the headlines, Diddy is the first head you’d chisel into the Rapper CEO Mount Rushmore. He started with Bad Boy Records before captaining the fashion, food, fragrance, booze, and television industries. It’s actually hard to believe that between all of his business ventures that the artist known as Puff Daddy even has time to make music, never mind also getting into scandalous fights all the time.

Still, we can’t hate. Forbes lists this guy as possessing a net worth around $725 million. That’s a boat load of shekels, worthy of the best PR team and lawyers. 

Tunechi himself has been working on his empire since the age of 15, when he first began the Cash Money Records collective. The label, in tandem with Wayne’s trademark style and out-of-the-box clever lyricism, was enough to make Weezy have a net worth of about $135 million, and now holds claim to Weezy’s imprint Young Money Entertainment, which breeds some of the more successful rappers (Drake, Nicki Minaj) in the industry today, and names Wayne as the CEO.

The current CEO and co-founder of Cash Money Records (alongside Lil Wayne, although they famously do not see eye to eye lately) keeps his money stack fat by serving as a sort of Godfather, shepherding countless young talents into the rap game.  Even though he stays busy, he still had a falling out with his former brethren-- the aforementioned Weezy F. Baby-- over apparent financial mismanagement (one of many which has plagued CM over the years). Regardless, Cash Money is still arguably the most influential label in the history of Hip Hop.

Dr. Dre has helped mold the genre that birthed him in his vision over three decades. There are so many layers and phases to both his music and business ventures, but Dre’s personal music-making days became few and far between after the emergence of Aftermath Entertainment-- the label he founded and still to this day serves as CEO of.  Known to dwell in the studio laboratory, either making beats or adding to the pile of his fabled vast library of unreleased amazingness, Dre figured, why not create an additional empire out of the things he spends time with most: headphones. Founding and CEO-ing Beats Electronics, Dre has made his music audio accessories synonymous with both sound and style, quite a feat.