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Like any successful music industry CEO, Damon Dash knows the value of building personal relationships. "Individual development is very important to me," he explained earnestly to the roomful of aspiring moguls who hung on his every word at this past week's How Can I Be Down? (HCIBD) conference on South...
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Like any successful music industry CEO, Damon Dash knows the value of building personal relationships. "Individual development is very important to me," he explained earnestly to the roomful of aspiring moguls who hung on his every word at this past week's How Can I Be Down? (HCIBD) conference on South Beach. "I spend so much time talking to my artists -- whether it's before they go to jail, or after."

Kulchur couldn't stifle a surprised laugh -- this was hardly the standard text at Harvard Business School -- but Dash wasn't trying out one-liners. "Beanie Sigel was supposed to come home today," Dash sighed of his Damon Dash Music Group's flagship artist. The Philadelphia MC had just completed his one-year prison sentence for gun possession and Dash was eager to have him back doing the promotional rounds for the commercially stalled album The B. Coming. Instead, just before Sigel's release, "some kid called him a snitch and he broke the brother's nose," a move that had extended Sigel's incarceration and scuttled a slate of media appearances. "It's a Catch-22," Dash continued with obvious weariness in his voice. "You love [Sigel] 'cause he's real, but it's the realness that puts him in jail."

Welcome to the big business of hip-hop, or as the 200 or so HCIBD attendees sitting rapt before Dash at the Shelborne Hotel preferred to call it: "the rap game." Prison time, gunplay, and thinly veiled death threats -- if marketed correctly -- could all be crucial parts of branding an artist in a milieu where the aura of gangsterism can be a key sales component. And who better to lay it all out than Dash, cofounder with Jay-Z of Roc-a-Fella Records, one of the past decade's most successful labels and a veritable template for hip-hop's now de rigueur persona of the street hustler-turned-lyricist.

Accordingly, for a journalist attempting to profile an up-and-coming rapper, detailing a lengthy rap sheet isn't only accepted, but it's also often encouraged by publicists. Assaults, attempted murders, and a murky past in the drug trade are all simply part of a memorable narrative. Much more damaging is the specter of approaching middle age and a stable domestic life, as Kulchur naively reported in a 2001 column on then-29-year-old Kendall rapper-cum-family man Mr. Cheeks. Having a wife and nearing the big three-oh may be routine in suburbia, but chronicling that kind of "realness" in print had those same publicists intimating all manner of bodily harm on an errant writer.

Sure enough, Mr. Cheeks's most recent album from this past spring came complete with a chilling backstory, and much like Kulchur's own mother, who is now a bit removed from her fashion-runway strutting days, Mr. Cheeks retains the uncanny ability to freeze time and celebrate the same birthday year after year.

This same guile was on display throughout many of HCIBD's discussion panels, though even some of the panelists grew frustrated at the disconnect from reality -- or at least the lack of common sense. "A lot of cats went out and spent $500 to $600 on an outfit to prepare for this conference," griped Miami producer Sahpreem King at one point. "And they only spent five to six dollars on their disc." He held up an unadorned, home-recorded CD, one of the many generic-sounding demos thrust into his hands: "They should've spent that $500 to $600 in the studio." As for the array of eye-catching oversize tire rims he'd noticed slowly cruising up and down Collins Avenue, "brand-new spinners are not going to get you a record deal."

Of course, true hip-hop players aren't even after record deals anymore. Dash seemed relatively unfazed by concerns over Sigel's future, or that of his label's other star, the now-deceased Ol' Dirty Bastard, whose singular take on "realness" extended to a fatal drug overdose this past November. Music was but one small part of his envisioned empire, Dash said, and just like entry-level drug dealers who begin "on the grind" by "pitching hand-to-hand," eventually "you want to evolve." As a sea of heads began nodding sagely, Dash added, perhaps for the benefit of a translation-impaired Kulchur: "You can't put all your eggs in one basket."

In fact, running a dairy farm is about the only venture Dash hasn't tried his hand at yet. He's co-owner of the Rocawear clothing line, Tiret luxury watches, the magazine America, the gourmet vodka Armadale, the Manhattan nightclub NA, a stable of professional boxers under the auspices of Dash-DiBella Promotions, the Donald Trump-modeled centerpiece of BET-TV's Apprentice-style reality show Ultimate Hustler, and not least a producer of films -- both blaxploitation shoot-'em-ups like State Property 2 and Paid in Full, as well as the artsy Sundance feature The Woodsman.

The success of many of these projects is still up for debate. Though Dash boasted his Rocawear "does $350 million a year," Russell Simmons made a similar claim in 2003 about his Phat Fashions line both in his memoir and to media outlets such as CNBC and Newsweek. Instead, as reported by the New York Times this past May, Simmons admitted in a civil deposition that Phat Fashions' true revenue for that year had been only $14.3 million. "You give out false statements to mislead the public so they will then increase in their mind the value of your company," Simmons conceded in his deposition transcript before asking, "It is not going to come out, right, about me lying to everybody? Right?"

Thankfully, Dash didn't need a court order to drop the braggadocio routine. He freely admitted his films had all flopped so far, a bust made even more painful because he'd broken the cardinal rule for Hollywood producers: Never invest your own money.

"Once they start asking me more than one or two questions," he said of potential film backers, "I'm walking out. I ain't good at asking people for things. My tap-dance game ain't there. When they told me The Woodsman would cost two million dollars, I said, 'Yo, I'm just gonna cut the check myself.'" It was a mistake he doesn't intend to repeat.

So were hearing these lessons worth HCIBD's $300 admission ticket? For Miami's next generation of apparently clueless talent, reminded by Sahpreem King to write their names and phone numbers on their demo CDs before handing them over, any advice would be welcome. Still, the best counsel of the weekend came from Dash, who seemed bemused by the crowd's preoccupation. He was more than willing to discuss the hidden dangers of "recoupable advances" and warn of ill-formed distribution arrangements. Instead he received an incessant line of questioning about "negativity" and "haters."

"Don't take yourself so seriously," Dash replied to one would-be star who looked to be on the verge of a breakdown. Playfully turning his baseball cap sideways, he cocked a finger back at himself: "I'm a kid from Harlem, just a kid from 146th and Lenox. This is a great hustle. I'd rather be here than being chased by police. And I'm too old to be back on the block."

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