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"Most of my friends would go over to this part of the community and want to aspire to be these drug dealers," he told CNBC's "The Brave Ones. "
"And many of my friends were dead or in jail at the age of 16 to 17. I was losing a friend every three months," he said.
But then a new kind of activity got popular: making music.
"They were just as wealthy, or even more wealthy, than these crack dealers, but they were selling music. It was LL Cool J, Run-D.M.C., Salt-N-Pepa, Tribe Called Quest, Ja Rule. All of them are from Hollis, Queens," John said.
And their music, hip-hop, was the social currency of the era, growing in popularity years before the internet or smartphones were widespread.
"Hip-hop was the voice of the streets and it was our version of today's Instagram or Twitter. And the kids were communicating through this music about their love, their hopes, their dreams, their aspirations."
And as music was mixed and tracks are sampled, so was fashion, according to Elena Romero, author of "Free Stylin': How Hip Hop Changed the Fashion Industry". "We took the brands that existed in those days and times and gave it our own spin," she told "The Brave Ones."
John's own apparel brand, FUBU (For Us, By Us) was created because John and his friends felt mainstream labels weren't aimed at them. "I just remember standing on that street corner and saying: 'This is For Us By Us. I understand what you want to wear. You understand what I want to wear. And if you're wearing this across the street, and I'm wearing it over here, we silently know that we all love hip-hop," he told CNBC.
Correction: This story was updated to attribute a quote to Elena Romero.