Camp Kendrick: Dave Free serves as manager of Lamar and president of TDE, the label that launched... [+]
In a back hallway of the Wiltern theater in central Los Angeles, Kendrick Lamar is sitting on a director’s chair next to labelmate Jay Rock, dutifully waiting to welcome every single one of the fans trickling in to meet him from a line that stretches seemingly all the way to Malibu.
It’s the last show of his Kunta’s Groove Sessions, a concert series at theaters that can fit only 2,000 people or so, roughly one-tenth the size of the arenas he appears destined to sell out in the near future. After this performance, he’ll head to his dressing room and sign 1,000 copies of his latest album, To Pimp A Butterfly, which helped Lamar earn 11 Grammy nominations this year, second-most by any artist in a single night after Michael Jackson’s 12 in 1984. In the meantime, he’ll sign anything his meet-and-greet visitors put in front of him.
“He wanted to make the fans feel like we’re still there,” says Dave Free, Lamar’s 29-year-old manager, a few moments before the show begins.
Like Lamar, the understated Free looks about five years younger than he actually is. But like many of his peers on our 30 Under 30 list, he’s already accomplished more than most people twice his age. In fact, of all this year’s honorees in the music category—including big names like Fetty Wap, Selena Gomez and Shawn Mendes—Free came the closest to a unanimous selection amongst our blue ribbon panel of judges.
The reason: Free has helped launch the career of the most significant West Coast rapper since Tupac Shakur. He met Lamar in ninth grade, and with the help of Top Dawg Entertainment (TDE) and later Dr. Dre’s Aftermath Entertainment and Interscope Records, Free has guided Lamar from the streets of Compton to the fast track to Grammy glory.
“It’s more like working with a brother that just so happened to love what I do, too,” says Lamar of Free. “So when you put these two individuals into creative spaces, it’s a different type of chemistry, it’s a different type of bond, it’s a bond that really can’t be broken … whether it’s in the studio or behind the camera. It’s like Voltron.”
The duo met in high school, and by age 16, Lamar had already earned a reputation as one of the most talented rappers in Southern California. His dense rhymes were often so complex that Free couldn’t understand what he was saying, and occasionally had to go back and listen to songs multiple times in order to fully comprehend them.
The year after Free graduated, he got a job working as a computer technician while continuing to help Lamar on the side—by any means necessary. One day he received a call from TDE founder Anthony “Top Dawg” Tiffith, a local underworld operator gone legit who, at this particular point in time, needed his computer fixed.
When Free arrived at Tiffith’s house, he assessed the situation and immediately realized he wouldn’t be able to fix the computer. But he knew he had an opportunity to get Lamar’s music in front of an important pair of ears, so he put on the rapper’s latest mixtape and started to take apart Tiffith’s computer. As soon as it was over, Free turned to Tiffith. “Man, I don't think I can fix this.”
Tiffith was much more impressed with Free’s client than his computer repair skills. By 2007 Lamar had signed on with TDE, which gave him and a growing cadre of young rappers access to a studio in Carson City, Calif., and a shot at wider recognition. That same year, Tiffith named Free the president of TDE. Lamar soon hit the road, serving as a hype man for labelmate Jay Rock. In his spare time, Free would upload Lamar’s music to the web and blast it out to anyone who’d listen.
In 2011, Lamar’s music finally started to catch. Eminem's manager Paul Rosenberg heard his music via RapRadar, one of the sites where Free had sent Lamar's mixtape, Section.80. Rosenberg alerted Dr. Dre, who then met with Tiffith and eventually worked out a deal to bring Lamar into the Aftermath/Interscope fold in a joint venture deal.
Though Dre offered the young rapper plenty of advice—ideas on intonation, advice on pronunciation and, of course, perfectionist production—Lamar didn’t need much help. “When we came in, he already had music,” says Free. “He already had ideas.”
Indeed, TDE has become something of a factory for successful young rappers. The label’s acts have amplified each other’s successes by touring together, appearing on each other’s songs and even sharing producers and mixing engineers—namely Derek “MixedByAli” Ali, another 30 Under 30 Class of 2016 member, who has mixed every TDE release to this point.
Lamar, Jay Rock and fellow TDE acts Ab-Soul and Schoolboy Q (another 30 Under 30 honoree) also founded hip-hop supergroup Black Hippy. Part of Free’s role as president of TDE: trying to replicate those acts’ success with more recent signees like Isaiah Rashad and SZA while continuing to boost Lamar and Q through the framework of TDE’s joint ventures.
“TDE is an independent, but we move and we structure like any of the majors,” says Lamar. “If we’re talking about Aftermath/Interscope and TDE, I’d say all of them are basically one big giant machine.”
TDE’s agility, Aftermath/Interscope’s reach and the co-sign by executive producer Dr. Dre came in handy for Lamar’s 2012 breakout album, good kid M.A.A.D city. The record sold 242,000 copies its opening week, and went on to earn platinum certification and heaps of critical praise. Pitchfork called it a “miracle,” praising its “dazzling lyrical virtuosity,” while publications ranging from Time to Billboard named it one of the best albums of the year.
But Lamar’s latest effort, last year’s To Pimp A Butterfly, is the record poised to launch the Compton rapper—along with Free—to levels few dreamed possible. With reviews perhaps even better than its predecessor and Grammy nominations galore, it seems likely to be the sort of event that solidifies Lamar as a musician who transcends genre.
That kind of crossover status translates to massive earnings, as fellow 30 Under 30 alum Drake can attest: the Canadian rapper earned $39.5 million last year, more than triple Lamar’s $12 million tally, thanks largely to arena shows and big brand endorsements. Lamar appears ready to make the move on the live side, but he has generally shied away from associating himself with products. Still, that doesn’t keep Free from maintaining constant vigilance.
“You have to have a desire, an unbroken desire, to be successful,” says Free. “You can’t actually sleep, you know what I mean? You have to see every opportunity and make something of every opportunity. There’s a million other people dying to have your spot, and they would do anything to have it. You can't just look at this as a hobby.”
Success has already brought riches—modest, by A-List hip-hop status—to Lamar: roughly $30 million in pretax earnings thus far. Though Free doesn't take a standard manager's cut, instead getting paid as a TDE executive, he's still getting compensated handsomely. To keep things in perspective, he’ll sometimes take a drive through Los Angeles to clear his head, making sure to pass through Skid Row.
“If you don't put yourself back in those places where you can see real life, you forget,” he says. “You’re just believing in this fairy tale.”
For Free and Lamar—whose future seems to promise a great deal more Grammys, sold-out arenas and critically-acclaimed new music—it seems the fairy tale is only just beginning.
Full coverage: The 30 Under 30 Class of 2016
For more about the business of music, check out my Jay Z biography, Empire State of Mind, and my other book, Michael Jackson, Inc. You can also follow me on Twitter, Facebook and by subscribing to my quarterly newsletter.
