It’s 36 degrees on the last Saturday night in October in San Antonio, Texas. As winter’s arrival looms over 25,000 Mala Luna Music Festival attendees, I’m escorted to the outdoor artist lounge and wait to converse with Wiz Khalifa.
In a meager attempt to take my mind off of what feels like the early onsets of frostbite, I build a rapport with both of Khalifa’s bodyguards and point one of them to the table of free nachos. Upon his return, we all bond over Cardi B’s lyrical prowess.
“How long have you been working with Wiz?” I ask, in between ineffective efforts to warm my hands with my breath.
“Since the beginning.”
Minutes later, I’m summoned inside the trailer temporarily housing Khalifa. The unit isn’t tall enough to allow the six-foot-four-inch rapper to stand upright. Still, he dutifully wraps up the last of an incessant string of photo ops.
Counting his debut mixtape Show and Prove in 2006, the Pittsburgh rapper is well into a decade-plus-long career in the music business. It’s not happenstance that he’s consistently found himself headlining music festivals, covering magazines and appearing as a Forbes Cash King. When one studies his career closely, it's evident his success has been contingent upon four integral pillars.
SERVING HIS CORE FAN BASE
Khalifa turned 30 years old in September. In his 20s, he built an empire that justifies retirement before the age of 40. But that’s far from ideal.
“I still wanna create, and I still have tons of ideas,” he said. “I’m a musical person so my words are my gift. Finding ways to get better is really the exciting part.”
Some of those ideas likely found their way onto his mixtape Laugh Now, Fly Later. Despite his massive commercial success - boasting hits such as “Black and Yellow,” “We Dem Boyz,” and “See You Again,” (which was once the No. 1 most-watched video on the platform) - Khalifa hasn’t deviated from releasing free product, a strategy he established early in his career to grow and satisfy his core fan base.
EXPANDING HIS BRAND
His Midas touch has spilled over into his side hustles, too. Khalifa raked in $28 million in 2017 because of his Khalifa Kush marijuana strain and Weed Farm mobile app; the latter has garnered four million downloads since its release in April.
“At the end of the day, everything I do business-wise is part of my real life anyway,” he claimed.
NURTURING HIS RELATIONSHIPS
Will Dzombak has served as Khalifa’s manager for the past 10 years. It’s somewhat of an anomaly in an industry where artists are prone to firing their right hands, even if they were instrumental in building a multimillion-dollar empire (i.e. Jay Z replaced John Meneilly after years of serving as his consigliere, despite Meneilly’s assistance in selling his Roc-A-Wear clothing line for over $200 million in 2007).
Nonetheless, the two spearhead Taylor Gang Entertainment, the record label is home to artists such as Juicy J and Ty Dolla $ign. To put it simply, Khalifa handles the front-of-house and face of the brand, while Dzombak handles the back-end logistics.
“There aren’t a lot of people who can find that complete reflection of themselves, who don’t do music but goes as hard in other areas," Khalifa said of Dzombak.
MAINTAINING A CONSISTENT WORK ETHIC
Over a decade into his career, Khalifa shows no interest in slowing down. When asked about what his plans for the future are after his mixtape drops he said, simply, “Just workin’.”