From Selling Crack To Cutting Checks: How Jay Z Made The Transition From Drug Dealer To Businessman


At the age of 43, Jay Z -- the man, the spectacle, the lightning rod that attracts irresistible headlines from, not just music, but all sorts of different verticals-- shows no signs of going down. Like one of his most popular and latest songs proclaims, he's simply got it.

His endeavors as a joint NBA franchise owner, record label president and all-around music icon (amongst other things) has seen him become one of the most widely respected pop culture figures of our time. Like many highly successful people, Jay Z has attracted so much admiration that people look past some of the more dodgy things he's done. Besides, talking about how he's transcend his industry is a much more entertaining topic, anyway.

But in the upcoming November issue of Vanity Fair, Mr. Carter not only opens up about his notoriously taboo past as a crack cocaine dealer, but also said that his experiences have actually provided him valuable lessons that are useful now in his life as an entrepreneur.

Vanity Fair states that the hip hop mogul was namely talking about his new role as a sports agent when it comes to how his past "lessons" are helpful to him now, a role that he's plunged into knee-deep as he seemingly tries to push the New York Yankees into giving one of his biggest clients, Robinson Cano, a $300 million contract.

While the admission may raise a few eyebrows, Jay Z's drawing of connections between the drug business and, well, business is nothing new. From Fortune Magazine's 1986 issue ranking the 50 biggest mafia bosses, which stated, ”the organization chart of a crime family or syndicate mirrors the management structure of a corporation,” to this retrospective article written by Karsten Strauss for Forbes.

Actually, more people than you might think, especially those who have, astonishingly, had the opportunity to dip their toes into both worlds and live to tell about from anywhere else but behind bars.

One man who fits that profile is former San Diego drug lord Jeff Henderson, who spent nine years in prison after his arrest in 1988 for selling crack. Having held a paper route as a kid, sustaining a 5-year career as a drug dealer, becoming a prison cook while behind bars and then leveraging that experience into becoming the first African-American chef at the Bellagio casino in Las Vegas to, now, heading his own business, The Henderson Group Inc., the 48-year-old is well positioned to say if there are any similarities between the illegal and legal hustles.

And when it's time to do so, he makes himself clear.

As Henderson delves deeper into his life as a drug dealer, it's fascinating to consider the multiple parallels that he draws between crime and legal entrepreneurship. One would be inclined to think their leg was being pulled if someone tried telling them that the two *ahem* occupations were very similar. How could that be? You might ask.

That question is answered very concisely as he talks about how he handled every aspect of his business on the streets, from marketing and public relations, to managing supply and cutting costs.

Henderson may come across as one who is lauding his former lifestyle, but he makes no mistake in stating that he is not proud of his past as a drug dealer. And while he does admit that the similarities between being a drug dealer and a businessman are numerous, he is very clear when it comes to expressing how those who are leaning towards a life of crime should use it to their advantage.

The idea may sound crazy at first (A Drug dealer? The perfect entrepreneur?), but, then again, Henderson does have the perfect case studies to point to, Jay Z and, of course, himself, two men for whom crime and corporation required one set of interchangeable skills.

Photo credit: WENN