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.

“I know about budgets. I was a drug dealer,” Jay Z told Vanity Fair contributing editor Lisa Robinson. “To be in a drug deal, you need to know what you can spend, what you need to re-up. Or if you want to start some sort of barbershop or car wash — those were the businesses back then. Things you can get in easily to get out of [that] life. At some point, you have to have an exit strategy, because your window is very small; you're going to get locked up or you're going to die.”

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.

"Maybe Fortune Magazine was right:" Strauss wrote in June 2012, "legal or illegal, business is all about problem solving and organizational structure. Who knew?!"

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.

"The same traits that a successful drug dealer has are the same traits any legitimate entrepreneur has," Henderson told the Huffington Post. "You have a product, you have a marketing plan, you have a vision, you build relationships. You outsmart [and] out-strategize the competition."

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.

"It's the same concept in any business -- if you're a car dealer, you need to go to Detroit," Henderson said. "You get as close to the source as possible and eliminate as many middlemen as you can to get the better price so you can increase your profit margin and ultimately be more successful than the competition. If you always have a better product and better price, word will spread."

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.

"I tell young guys: 'If you're a gang leader, you have the ability to convince people to listen to you, buy into your program and follow you. You have great leadership potential, understand logistics and manage a diverse workforce. You just have to change your path and the type of people you deal with, and you could be successful, too.'"

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.

"I would take potential clients to lunch or dinner, buy the gifts, take them shopping. Like any businessman, if you want to do business with someone, you court them. I didn't know what those words meant back then -- marketing, PR, strategic relationships -- but it came naturally to me."

Photo credit: WENN