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The King of Everything: Sean Combs

To get to the top, Diddy had to outwork everyone.
The King of Everything: Sean Combs
The King of Everything: Sean Combs

Sean Combs has accomplished more in fifty years than most could accomplish in a hundred. In the time since he started working when he was 13, Combs has amassed a $740-million-dollars worth—but what’s more impressive than the money is the number of ways that he’s done it.

Comb's story is multiple lifetimes of self-made success rolled together: from an artist who’s performed under no less than four names — from Puff, to P. Diddy, to Puff Daddy, to Diddy; to a marketer who took a fifty-percent stake in a floundering vodka brand and found a market to sell millions of cases a year; to a guy who started off as a record label intern, then left to start his own label—and then became a multi-platinum selling artist in his own right. And he’s still not done.

Combs has been, from his youth, a hustler in the very best sense of the word. Someone who has never stopped reinventing himself, never recoiled in the face of a challenge, and has never been satisfied, no matter how much success he’s found. Even now with his almost three-quarters-of-a-billion-dollar fortune, Combs proudly announced last year that he’s become the mentee of billionaire investor and hedge fund manager, Ray Dalio. Yes, you read that right —Diddy wanted a mentor.


To most, it’s unfathomable what would make someone with so much success already under their belt feel the need to learn anything but how to perfect their golf swing. But we get it. Because we know that what keeps Diddy going is the same thing that got him hustling all those years ago with his paper route, is the same thing that we’re chasing today as we watch our company grow. It’s the challenge to see just how far we can take things: and no matter what success we have, we’re always going to be on that journey.

But big dreams, and a desire to do big things, don’t make multi-millionaire media moguls like Combs. So what was it that set him apart, and earned him the worldwide influence that he has today? If you asked Diddy, he’d say it was one thing:

“Success doesn’t just land on your lap. You have to work, work, work, work, and work some more.”– Sean Combs


Before the vodka company, the Grammy awards, the platinum records, the buzzed-about fashion, or the absolute legend that Diddy has grown into, he was a paper boy. To be more specific, he was a paper boy franchise. At the age of 13, Combs, in need of some cash but too young to work, found a way to get around the age requirements to get a route: he talked a high school graduate into keeping his paper route, and letting Combs deliver it for 50% of the pay. Then he repeated the process with several other kids.

Combs credits that story to his entrepreneurial spirit showing up early, but the true motivation came the lack of money that was available at home. At 13, Combs was living in Mt. Vernon, New York, as the child of a single mom who, herself, was working three to four jobs. It was a second life for the family, a calmer environment that his mother sought out after her husband was murdered while sitting in a parked car in Harlem, when Combs was only two.

The years since weren’t easy for the family, and his mother worked four, five jobs at a time. Today, Combs credits the incredible way his mother worked for his own insane work ethic and desire to always be doing more. But back in 1983, all that Combs knew was that when he asked his mother for a pair of shoes, she almost started to cry. In his words, “My hustle was born. I never wanted to see her face like that again.”

“I called one of the guys that was going off to college and told him I'd deliver his papers...He accepted it and then I franchised it out and by the time I was 14, my mother didn't have to have that look on her face anymore."– Sean Combs

In his time as a paperboy, Diddy learned another valuable lesson: one in customer service. He purposefully placed every paper inside the screen doors on his route, to be just that much better than the paper boys who had the route before. It was all part of his master plan: one that he seems to always have stewing in the back of his mind. No matter what endeavor he’s following, Combs seems to be a few steps ahead of everyone else. Thinking a little bit harder. Making his moves a little bit earlier. Even if sometimes it means going against what most would consider prudent advice.


Combs left Mount Vernon when it came time for college and moved to Washington D.C., where he attended the historically black Howard University. By the time he entered college, Combs had already earned his nickname “Puff” on the high school football field, where he was known to huff and puff when he got mad, but it would be years before he put that name to use as a rapper. At Howard he was focused on studying business: until, that is, he got an internship that would change his life, at Uptown records.

Working at Uptown, It didn’t take long for Combs to realize that what he was doing at Howard wasn’t enough to keep his attention. And he was making a four hour train commute from D.C. to New York, where Uptown was headquartered. So he dropped out of Howard after two years, and focused full-time on Uptown, where he was quickly promoted to A&R and worked with a few new artists: among them were Mary J. Blige and Jodeci. In fact, Diddy rose so fast that he was entrusted with Executive Producing Mary J. Blige’s What’s the 411 which hit number six on the Billboard charts and went on to go triple platinum.

While there, he also started working with an artist named Christopher Wallace, who would ultimately be the end of his time at Uptown. Uptown was releasing records in partnership with MCA, and when Combs tried to release the uncensored, raw rhymes of Wallace, the partner balked and wanted to reign them in. That’s when Combs would receive the greatest gift that is so well known to so many of the self-made: he was fired.

“I don’t believe in fear – I live my life without regrets."– Sean Combs


When Combs was fired from Uptown records in 1993, he immediately turned around and founded his own label, Bad Boy Records. It would become not only an icon in the music industry, but the foundation upon which Combs would build his larger-than-life aspirations into a reality. Because it turns out when Uptown fired Combs, they let two legends walk out their door that day. Because Christopher Wallace, the artist that Combs got fired from Uptown over, went by another name: the Notorious B.I.G. And when the label released his debut album, Ready to Die, in 1994, it was met with critical acclaim and went on to secure Comb’s legacy as a producer who launched some of the biggest artists in the industry. 


Over the next three years, Combs continued to build Bad Boy, and the list of hits got longer and longer. The company worked with Usher, Lil’ Kim, TLC, Mariah Carey, Boyz II Men, and more. From ‘94–’95, Combs produced several songs for TLC. And all the while, behind the scenes, another plan must have been taking shape. First, for Comb’s own music career, and second, for his business to become what it is today: something far more than music—an entire lifestyle that could be bought and lived at every waking hour, with all of the profits going directly to Combs’ enterprises.

“I wanted to make the records that you woke up in the morning to. I wanted to make the clothes you got into after taking a shower. I wanted to make the cologne you put on after that...the water that you drink...I want you to be able to turn on the TV and watch one of the television shows I produce."– Sean Combs

The first step in that evolution was for Combs to start to release his own music, which he did in 1997. He released “Can’t Nobody Hold Me Down” and the success was instant: it was on the Billboard Hot 100 chart for 28 weeks and hit number one. He followed it up with a debut album that went number one in the first week and sold more than half a million copies. In 1998 it got five Grammy nominations and won Best Rap Album. And that same year, Combs launched Sean Jean: the clothing enterprise that would expand his business from music, to every part of culture.



How Combs keeps up the pace of life he has today is impossible to understand. He’s said of himself, “I’m not human. I’m a machine.” He talks about working eighteen hour days, and is quoted as saying that if you work for him, sleeping if “forbidden.” But for Combs, it works. From the time he first discovered hits at Uptown, it seems that the story has only been up from there. 

When Combs launched Sean Jean in 1998, it wasn’t long before it received acclaim in the fashion world, being nominated for every year from 2000 to 2005 for excellence in design by the the Council of Fashion Designers of America.

Two years later he was approached by Diagio about developing his own brand of spirits, but saw a different opportunity. Looking at their portfolio he noticed Ciroc, which he had tasted, and asked about its performance. The brand was faltering and selling only around 30,000 cases a year. Not even remotely great. But worried about how long it would take to start his own brand, Combs took this as an opportunity and got straight in the game as a 50/50 partner with Diagio in the brand. With Diddy involved, in 14 months the brand was selling more than a million cases.

From there, Combs has only continued to expand his portfolio. He’s teamed up with Mark Wahlberg on a performance water brand, Aquahydrate, and even launched a cable network called REVOLT in 2013. The dream Combs had of owning brands that could cover every part of everyone’s day turned out to not just be possible, but a reality—and he’s not done yet.

As a tireless businessman who’s never ceased to find new ventures, the next step for Combs is anyone’s guess. But looking back at how he’s amassed the fortune and influence he has today, the path to get there will look at logical and measured as the way his history until now appears: just the next logical step for someone on a path to always become greater. But that easy chain of events looking backwards belies an important truth about Comb’s success: that from his very earliest days, he knew where he was going. Even back when Combs was working his paper route, he felt deep down that he was going to shape the world: born to shake things up. And with an insatiable work ethic like his, and that solid vision in his mind, there appears to be no limit at all to what Sean Combs can become

"I'm gonna go down in history as being one of the best music men and businessmen in entertainment ... The people that I'm going to be greater than are Steven Spielberg, David Geffen and Clive Davis."– Sean Combs