Today, Sean Love “Diddy” Combs turns 50. See how hip hop’s original self-made mogul revolutionized entertainment and entrepreneurship, teaching an entire generation the art of hustle.

When New York City cops were targeting and shutting down hip hop clubs, Diddy was there. In 1986, when Run-D.M.C. performed at Madison Square Garden for the “Raising Hell Tour” and asked fans to raise their kicks to “My Adidas,” Diddy was there. When Teddy Riley needed an intern to carry his keyboard, Diddy was there. When Mary J. Blige still lived at Schlobohm Housing Projects in Yonkers and needed a ride to the city, Diddy was there. And when thousands of people lined the streets of Brooklyn to bid The Notorious B.I.G. farewell, Diddy was there. The crowd chanted “We love you Biggie,” throwing up peace signs and power fists as his funeral procession crossed Fulton Street. Diddy saluted the crowd right back and said “thank you.” The music pioneer has not only witnessed hip hop evolve from being a ridiculed art form; cultivated by economically oppressed black, Latinx, and queer youth; he helped globalize it.

Late 1980s – 1993: The Genesis

In the beginning, there was an ambitious kid from Harlem nicknamed Puff. He made it to Howard University, but even before stepping on campus, he had already secured a few key wins. He was a back-up dancer for Big Daddy Kane and Heavy D, did an internship at WBLS radio station and more importantly, started working for his mentor Andre Harrell, the founder and CEO of Uptown Records.

Puff spent several months persuading Heavy D to get him the internship and another 6-8 months to work directly for Harrell. So, even though he had classes at Howard University (located in Washington, D.C.), there was no way Puff was quitting his internship at Uptown Records. In order to satisfy his family’s academic expectations and continue impressing his boss, he would routinely commute from D.C. to New York. As the demands of his internship grew, so did his opportunities. Puff produced a remix for Jodeci’s “Come & Talk to Me.” The single became a hit, selling over 3 million copies. And let’s be clear: It was only after that moment, the now-mogul was able to parlay his internship into a paid, executive position as the label’s talent director.

To accept the job, Puff dropped out of Howard during his sophomore year. As Uptown’s talent director, Puff signed and developed artists who have now become household names (like Mary J. Blige). He innovated and popularized concepts millennials should never take for granted such as R&B remixes (featuring rappers at the beginning of a song) or Hip Hop Soul.

Nothing in entertainment (or life) is guaranteed. So in 1993, despite the hits and his knack for fostering talent, Puff was fired. However, Andre Harrell still believed in his mentee. When letting him go, Harrell agreed to let the 24-year-old keep an artist from Brooklyn he just signed: The Notorious B.I.G.

1993 – 1999: No Way Out

After being fired, Puff signed a deal with Arista Records to launch Bad Boy Records. Initially, Bad Boy’s partnership with Arista was a production deal. It was only after the success of singles like Craig Mack’s “Flava In Ya Ear” and artists like Biggie did the production deal get upgraded. Nothing legendary comes easy. Sean “Puffy” Combs and Bad Boy’s Hitmen production team had to sell millions of records and show direct proof of cultural capital before even being able to secure better ownership rights, and distribution with Arista. In 1997, just as Bad Boy Records was entering the mainstream stratosphere, Christopher “Biggie” Wallace, the label’s main star was murdered.

GQ

Rather than let the tragedy consume him, Combs pushed forward. His best friend and creative partner was gone, but through Bad Boy Records, he was determined to ensure that the world would remember him forever. “I’ll Be Missing You” became the first rap single in history to debut at No. 1 on the Billboard charts and went on to sell 8 million copies. The next year, Combs won two Grammy awards for his debut album, No Way Out, and the song. As he explained on Netflix’s “Hip Hop Evolution,” “‘Missing You’ was the first record to go number one in every country, so it wasn’t all pain. But, it could never feel as great as it’s supposed to feel with Biggie being here.”

2000 – 2009: Bad Boy for Life

In 1998, Combs established Sean John. And in 2004, he made history by becoming the first African-American to be named Best Menswear Designer of the Year by The Council of Fashion Designers of America (CFDA). The kid from Harlem, who grew up admiring pioneers like Dapper Dan and Karl Kani, noticed how bigger luxury labels were copying hip hop swag and streetwear without being willing to acknowledge black creators or consumers. Instead of waiting around for validation from high-fashion European or American distributors, Combs focused on strengthening his own ventures. He made sure Bad Boy Records and Sean John would complement each other, and created one giant marketing machine: A hip hop ecosystem that couldn’t be ignored. Puff was now Diddy. And Diddy wasn’t afraid to flaunt. He was a black man who was unapologetic about having refined taste and being wealthy. Whether it was fragrances like I am King (dedicated to Dr. Martin Luther King Jr., Muhammad Ali, and President Obama) or a bottle of Cîroc, the mogul promoted an aspirational lifestyle rooted in hip hop, blackness, and luxury; and it was exported globally.

2010 – 2019: Victory

Following the success of his 50-50 profit-sharing partnership with Cîroc vodka, Diddy added more beverages to his shelf. In 2013 (the same year REVOLT Media & TV launched), he purchased DeLeón Tequila in partnership with Diageo (the owners of Cîroc), maintaining 50% ownership. And in 2015, he invested a majority stake in AQUAhydrate, an athletic beverage. In September 2019, Alkaline Water Company acquired the brand in a deal that put its worth at an estimated $50 million. Throughout his career, Diddy has projected a public persona and charisma that often makes what’s difficult look very easy. However, for every major win, he has always had to establish proof of concept. Not through a blue icon verifying status on digital platforms, but actual sales. Diddy’s legacy is that he has never accepted the “negatives” of life as his permanent living narrative. To push through when you have every right to remain bitter is one of the many lessons Dr. Combs passed on in his 2014 commencement speech to Howard University’s graduating class.

No matter the challenge, he has always remained hopeful. Treating rejection as fuel, he’s a motivator, while pursuing and being black excellence. Happy birthday, Diddy!