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Practical Business Advice From a Chicago Drug Dealer

03/18/2010 05:12 am ET | Updated May 25, 2011

It was typical spring day in Chicago, which means that it could have been gray and snowing like hell, or raining and chilly, or something else. This particular March afternoon, however, was a bright, dry eighty degrees with a sky that was bluer than Lake Michigan. My friend, whom I'll call 'D,' was meeting a business associate in the Loop, trying to make a living like the rest of us. He yawned pulling into a parking spot - warm weather makes him sleepy - and was arrested by federal drug enforcement agents.

Pump-action shotguns pointed at his head were not what he had expected, but he was not completely unsurprised, either. He'd been dealing drugs in one form or another since he was 13 years old and was acutely aware that all things - profitable, illegal, and otherwise - must come to an end. In many ways, he was ready for it to be over.

The charge, which was undeniable, was conspiracy to distribute narcotics. He didn't have any coke on him but it didn't matter - the feds had him dead to rights, and all he could think to ask as they applied steel bracelets was if the arrest meant he wouldn't make his trip to Las Vegas the following day. The agents chuckled a little and said, yeah, that's what it meant.

Turns out it meant a whole lot more.

Several months later, 'D' demonstrated his willingness to cooperate with DEA by making a controlled buy. Since then, the process that began with his arrest and subsequent lawyering-up has slowly culminated in sentencing, which will happen soon. 'D,' who did not possess a criminal record before his arrest, could get six months or he could get 10 years to life. The law that applies to his crime is, at the moment, in flux. Although his fate is in question, the long path to sentencing has been, for the most part, bureaucratically stultifying. There has been skillful negotiation by his lawyer and logical pronouncements by the judge, but little drama and absolutely no excitement.

In other words, the opposite of 'D's' life as a Chicago drug dealer.

At the time of his arrest, 'D' was moving in a rarified crowd. He did business with notable figures in the worlds of Chicago politics, law, charitable giving, sports, and entertainment. 'D' is quick-witted and personable - people like him and want to be liked by him - and his role as salesman of controlled substances merged seamlessly with that of invited guest, and then confidant, in a number of exclusive circles. From street-level distribution on the South and West Sides to coke-sniffing powerbrokers on the Gold Coast, drugs are ubiquitous in Chicago, the grease moving many wheels of influence. The Windy City feeds a twin dependency - celebrities, socialites, and the politically-connected who pay top dollar for discreet indulgence of their habits versus the agencies and organizations that police it - and 'D' was at its confluence. He watched both halves of the druggy whole not only interact, but protect one another, and party together.

Full disclosure: my relationship with 'D' is borne from collaborating on his concept for an original TV series chronicling the Machiavellian, morally ambivalent Chicago drug culture in which he flourished. Our search for a producing partner is just beginning, and as we continue to tweak the material, making it as real as possible, 'D' reminded me that, "As in any career, there are things people can't know unless they're directly involved in the field." I asked for examples, and while his reply didn't surprise me, it did underscore an important aspect of his former life: in essence, 'D' was a conservative, one-man small business. He was a pusher, to be sure. It just so happens that what he was pushing, mainly, was a pencil around a piece of paper, trying to balance product and sales in order to turn a profit. To that end, he established a set of 12 simple business principles, which I've transcribed below; the quotations are his:

1) Relationships: Each customer is different: be sure that they know you personally, by name ("whatever name you're using that week")

2) Communication: Have constant access to phone, text, and pager so that customers can reach you, day or night ("swap them daily and discard them monthly")

3) Savings: Keep a healthy amount of cash in reserve ("cash on deck")

4) Credit: Cultivate positive working relationships with associates who have ("cash on deck to lend")

5) Support: Retain a qualified attorney at all times ("make sure he has bail money")

6) Diversify: Invest profits wisely and pay all taxes early and in full ("Uncle Sam needs his cut, too")

7) Trust: Business is business: trust only yourself to look out for your own interests ("your mom will sell you out")

8) Security: Conduct extensive background checks on every client, employee, and vendor ("everyone has secrets")

9) Strength: Show no weakness, or both clients and vendors will take advantage ("lion versus the lamb principle")

10) Truth: Being dishonest will cost you business or reputation ("or worse")

11) Insurance: Buy the best liability insurance money can buy for when something happens ("liability insurance means muscle")

12) Resources: Cultivate friends in high places ("on both sides of the law")

In theory and principle, what 'D' did was both wrong and illegal, and he knows it, and I know it. While it's easy to draw comparisons between alcohol and drugs (both are controlled substances, both are physically and emotionally addictive), the only point that matters is that one is legal to sell in the United States, and the other is not. If a law requires change - if popular consensus demands it - then the democratic process must be followed for the legal system to remain intact. But it's also unrealistic to pretend as though the drug business is not, in fact, a real industry, or that it has not infiltrated all levels of society, or that it's under control. It's not, because in addition to being incredibly profitable, it's also a hotbed of innovation and excitement for a certain type of ambitious young businessman.

What better place for it to flourish than a city that was founded by entrepreneurs and criminals alike?