Profile in Action — On to the Next One: How Jay-Z Used Mentors to Get to the Top

Jay-Z was raised by a single mother in the Marcy Projects of Brooklyn. His father flew the coop when he was 10, and Jay-Z was largely left to fend for himself. With origin stories like this we often attribute outliers to God-given talent or an unceasing drive for success. 

It’s true that Jay-Z possessed both of those in spades, but he was also humble and savvy enough to recognize when he crossed paths with someone he could learn from to reach his final destination.

First, it was Jonathan “Jaz-O” Burks, an older rapper from Marcy who recognized himself in the young, hungry rapper. Jaz-O helped Jay-Z improve his rap skills, teaching him not to practice on his craft on the corner, so that when he would spit in the streets or a club people would wonder how he made it look so easy. 

Jay-Z then partnered with his high school classmate and fellow dropout DeHaven Irby to learn the drug game in Trenton, New Jersey. While selling cocaine he developed his penchant for profits, eventually expanding their operations to Maryland and Virginia where there was more room to breathe away from New York.

Later he would persuade rapper Big Daddy Kane to let him travel on his tour bus, earning his spot by rapping during intermissions at his shows that featured artists like Queen Latifah and Tupac Shakur.

Jay’s third and most fruitful mentorship was with Damon Dash. Dash was from Harlem and a hustler in his own right as a club promoter. Dash was skeptical of the rumors about Jay-Z’s talent at first, unable to fathom there was a rapper that good from Brooklyn. But upon meeting Jay, he knew he had the goods. 

Soon after partnering up, Jay and Dash tried selling Jay-Z’s legendary first album, Reasonable Doubt, to record labels, but they were met with a series of rejections. Undeterred, Dash decided he and Jay would start their own label, Rock-A-Fella Records and sell the album themselves.

They started by selling Reasonable Doubt out of the trunks of their cars, going anywhere to sell the album, even barbershops. 

Reasonable Doubt sold 420,000 copies in its first year.
With the hype they built from their ground game, they were able get an unheard of deal with Def Jam Records for the second run of Reasonable Doubt, splitting only a third of the profits with the company. Years later, Jay-Z would become CEO and president of Def Jam Records, usurping his mentor Dash when he bought out his stake in their apparel company, Rocawear.

Jay-Z’s friends and collaborators have attributed his ability to spot knowledgeable people and quickly absorb their wisdom to his humility and curiosity. By holding onto what Buddhists call “beginners mind,” or a child-like attitude of openness and lack of preconceptions, Jay-Z quickly recognized people who knew the landscape and ingratiated himself with them.

 Upon happening upon new territory, whether in hip-hop or drug dealing, Jay-Z was able to learn from, and quickly surpass, mentors who had been working at it far longer than he had. Instead of trying to go it alone (he probably could’ve), or being intimidated by people with more power and status, which would have flattened his rise, he swallowed his pride and sought out partners in crime.

 By ingratiating himself with people higher on the food chain, constantly asking questions, and internalizing their wisdom, Jay-Z was able to go from street hustler to the CEO of Def Jam Records in 10 years.

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This was previously published on Medium.