Credit: Mikamote

Before becoming a billionaire and one of the greatest rappers of all time, Jay-Z sold drugs around the Marcy Projects. He started selling drugs at the age of 13 after the crack epidemic took hold in the 1980s. After his father left when he was 11, Jay found his place in the streets, looking up to dealers in his local neighbourhood.

However, after experiencing multiple deaths and incarcerations, Hov realised he needed to find a way out. “I started seeing people go to jail and get killed, and the light slowly came on,” he told Oprah Winfrey. “I was like, ‘This life has no good ending.'”

Jay was in his early adulthood when he came to this realisation. He split his time between drug dealing and rapping, becoming known as Jazzy, selling records out of his car. Hova gained a loyal following before launching his label, Roc-A-Fella Records, in 1996.

He was around 20 years old when he decided that he needed to quit the streets to pursue a thriving music career. “I’d been trying to transition from the streets to the music business, but I would make demos and then quit for six months,” he said to O Magazine. “And I started to realise that I couldn’t be successful until I let the street life go.”

Jay took advice from his mother in putting an end to selling drugs, believing he had to put his all into making a career out of music. It was a considerable risk but one worth taking.

“My mom always taught me—you know, little boys listen to their mums too much—that whatever you put into something is what you’re going to get out of it,” he recalled. “I had to fully let go of what I was doing before for the music to be successful. That was a leap of faith for me. I said, ‘I have to give this everything.'”

Everything Jay experienced up until age 26 was put into his debut album, Reasonable Doubt, which was released in June 1996. It’s his favourite project of his career because it presented his life struggles until that point, allowing him to pour his heart and soul into it when he wasn’t the success story he is today.

“That first album, Reasonable Doubt, is my favourite because all the emotions and experiences of 26 years came out in it,” he said. “That was the record I had 26 years to make.”

Hov sold drugs as a way to survive in Brooklyn and learned how to manage money along the way. “I know about budgets. I was a drug dealer,” he told Vanity Fair. “To be in a drug deal, you need to know what you can spend, what you need to re-up.”

When asked if he regrets dealing drugs, he said, “Not until later, when I realised the effects on the community. I started looking at the community on the whole, but in the beginning, no. I was thinking about surviving. I was thinking about improving my situation. I was thinking about buying clothes.”