After prep school, he built a thriving business. Now he’s got to find a way to get out of it.
By David Amsden
One of four phones Lenny uses for business; this one is for staying in touch with runners making deliveries. The phone numbers are prepaid, attached to no name.Every day he tells himself the same thing. You are doing nothing wrong. It plays through his mind on repeat, keeping his nerves in check. You have no reason to worry. Tonight, a Friday, he is walking down a cobblestone street in Soho, hands wedged in his leather jacket, his posture slump-shouldered, as if he’s curling in on himself. In his right-hand pocket, there is a plastic bag containing numerous smaller plastic bags — "tickets," he calls them — filled with either a gram or gram and three quarters of cocaine. The smaller ones he calls "chiquitas." They cost $60. The big ones, known simply as "big ones," go for $100. He is heading to see a customer, a twiggy, doe-eyed woman who asked to meet outside an art gallery. He thumbs through the Baggies, able to gauge the weight with his fingertips, and secures her order in his fist, all the while humming along to the voice in his head.
You are doing nothing wrong —
This is deluded, he knows, but in his business, delusion is everything: both what you're selling and how you sell it. His name is Lenny Starke, or at least that's what we'll call him here, and seven days a week he moves through the city like this: making pickups and deliveries, a sequence of handshakes and handoffs that earns him, tax-free, about $5,000 a week. This places him somewhere in the middle of the $92 billion worldwide cocaine industry, above petty street dealers, below the organized syndicates that are his main suppliers. Given Lenny's upbringing — the socially ambitious parents, the airy Manhattan apartment, the uptown private school — dealing seems an odd career choice. But to him, it's almost logical. His financial portfolio is impressive: $30,000 in a safe bolted to the floor of his apartment, another $25,000 in storage at a "wholesome" friend's house, and a steady stream being invested and washed clean in the stock market. And when Lenny wants to spend a weekend on Shelter Island or comes down with a cold or just feels like staying inside and playing Grand Theft Auto—a video game in which the hero is a drug dealer—he has a rotating cast of employees who do the work for him. All this, and he is not yet 25. "I'm going to be financially set," says Lenny. "I can skip a step. I'm able to pay for my apartment without having to work a crap job or having to ask Mommy and Daddy to send me rent checks every month—that, to me, is just as bad."
It's an absurdly warm night for March, still early, edging on 6:30, that hour when the tension of the workweek gets eclipsed by a restive desire to get a little lost. Lenny's cell rings repeatedly. Per dealer protocol, the number is prepaid, attached to no name, untraceable. The phone is an old-school, beat-to-hell Nokia that he refuses to upgrade, Lenny being somewhat superstitious. "Probably it's the warm weather, but I'm thinking tonight's gonna be busy," he says after taking a call, this one from a 21-year-old kid so "papered up" — Lenny's term for those with enviable wealth—that his parents bought him an entire brownstone. "The kid is a spoiled brat, basically, who wants to pretend he's all thugged out," Lenny continues, seemingly unaware that the same could be said about him. "Anyway, those calls just now? That's three more orders, and we only walked, what? Four blocks. It's cool, but I was hoping to kick it, have a beer. I've been working since, like, noon, right? Went up to midtown for the day shift. That's finance types mainly, guys in suits, some people in fashion. I meet them at their offices. Or on the street, real quick, boom-boom, you know? Or in banks, right in the lobby by the ATMs. Banks are my favorite. Nobody is thinking people are buying coke at a bank."
Dealing has always appealed to Lenny's two most dominant personality traits: an obsession with money and chronic impatience, characteristics that don't exactly set him apart from his peers, kids who came of age during the hip-hop and Internet booms, two movements united by the philosophy that money is something to be made quickly, dubiously, and only in large amounts. "I was always the kid that wanted more," is how Lenny puts it. "I never grew up with nothing, but I never had enough. If you gave me $20, I wanted $40. I like eating out, I like nice things. I can’t really function if I can't get what I want. Ever since I was little, I would just go out and get, you know?"
About $25,000, a fraction of his savings. He nets an average of $5,000 a week and stores much of his money in a safe bolted to the floor of his apartment. But, lately, as his friends settle into careers in private-equity consulting and cosmetics PR, Lenny has found himself questioning his profession. Whenever he tries to imagine himself five or ten years down the line, his mind either shudders and comes up blank, or spits back images of clichéd cautionary tales: Lenny the Addict, Lenny in Jail, Lenny Dead. "I'm not gonna be 30 years old and feeding my babies with this," he declares, but given that he's often in debt up to $15,000 to a man who regularly carries a gun, getting out is more complicated than suddenly growing a conscience and tossing your phone into the East River. "You have to get out smoothly," says Lenny. "Same way you got in."
With this in mind, he has recently set in motion a plan for retirement, one that gains momentum with each customer he greets —
"Hey, baby, what's up?"
Outside the gallery, the doe-eyed woman hurries across the street, her vintage riding boots clicking on the cobblestones. There must be an opening tonight, because bodies are pouring into the street, blocking traffic. Beneath the thin yellow glow of the streetlights, the figures are silhouetted: a sea of conceptualized hairstyles all referencing bands that Lenny, who listens almost exclusively to hip-hop, has never heard of.
"Yeah, baby, long time no see."
With that, Gallery Girl presses her waxen cheek to his, kissing the air just below his earlobe. Lenny can smell her perfume — vaguely citrus, superclean. He shakes her hand, sliding the two big ones she ordered into her palm. She slips the Baggies into her purse as they walk through the crowd making small talk, two old friends who know nothing about each other. Eventually, they stop and she gives him another delicate kiss, this time reaching out her other hand, the one that's been palming $200 the entire time.
"See ya, baby," she says, cantering across the street and disappearing through the gallery door.
Lenny, meanwhile, goes into accounting mode.
After every delivery, he pulls out his T-Mobile Sidekick and uses its tiny keypad to record the specifics of the transaction just completed: customer nickname, quantity purchased, cash received. This information will be erased later tonight, once he gets home and downloads it into a Microsoft Excel spreadsheet tracking every deal he's made over the past year. That file is then purged from his hard drive and stored on an unlabeled diskette: a cheap, flimsy piece of plastic that Lenny hopes will make him a small fortune. Like many markets, the drug business thrives on mergers and acquisitions, or what is known in the trade as "selling your numbers" — giving up your phone and client list for a fee. Every dealer keeps track of his profits in one way or another, though Lenny's Excel document is likely a rare prep-school touch, one he hopes will boost his sale price. Recently, he heard about a pot-delivery service going for $50,000, but cocaine is both a pricier drug and a growth industry — use among adults has been increasing nationally since 1999 — so he's thinking he could double that number. "The rule in any business is that you don't sell your company for what it makes in a year," explains Lenny, "but for what it makes in two or three or four years, right? Well, in my business, you can't do that. Someone gets arrested and — boom — it's over. So you gotta sell it based on what you make in, like, six months."
And that, in outline, is Lenny Starke's retirement plan: Cash in, cash out, and use the windfall to invest in something legitimate. A business of some sort. Real estate, for instance. Maybe get an M.B.A. Every now and then Lenny even thinks, half-seriously, about law school. "Yeah, it's ironic or whatever. People say, 'Oh, law school, yeah-yeah ...' But doing this has made me better suited," he claims. "I'm a good talker, good at sitting down with people and working out deals. Half of law is the pretrial stuff you don't see on TV, striking deals behind the curtain, which all comes down to money. Well, that's the *&^% I do every day."