10 Business Lessons I have Learned from Sean “Diddy” Combs

Part 1

Words By Nick Kaoma

“Ten years from now we’ll still be on top/ Yo, I thought I told you that we won’t stop”

Diddy, Mo Money, Mo Problems, 1997

Forget the initial 10 year outlook, 23 years after founding Bad Boy Entertainment, Sean “Diddy” Combs is still on top. And like he promised, he hasn’t stopped. Diddy or Puffy, as many still call him, is still one of the most ubiquitous characters in hip hop and global entertainment. He has literally seen it all and done it all.

Diddy is a certified hustler and marketing genius who has spread his tentacles across multiple industries in a manner that would make the original hip hop mogul Russell Simmons extremely proud. Diddy’s story is a thing of legend. He started off as Andre Harrell’s assistant at Uptown Records and eventually blossomed into VP of A&R after making a success of artists such as Mary J Blige and Jodeci. Diddy did not only fine-tune their sound but he also shaped their styles and on-stage personas.

Being a kid from Harlem Diddy was always oozing with style and confidence. Over the past 27 years Diddy has updated and packaged that same style, swag and attitude and sold it to us in various forms …. Ciroc, Sean John, Aqua Water, Revolt and Bad Boy all carry Diddy’s indefatigable spirit which we all need a small piece of in order to become the best versions of ourselves. Or at least that’s what Diddy would like us to believe. Take that, take that!

I’ve grown up admiring Diddy’s business and marketing prowess – he has done things like no other. Do you guys remember his B.I.G MAC campaign that he used to to launch Bad Boy Records’ Craig Mack and the Notorious B.I.G? It was so ingenious that Madison Avenue’s favorite Hip Hop marketing whiz Steve Stoute calls it “one of the best marketing campaigns ever”.

“I’m tryna push you to Supreme Being … You don’t wanna embrace your destiny/you wanna get by” – Diddy, Nobody, 2015

Diddy entered the entertainment scene at the tender age of 18. He might have lacked experience when he convinced Andre Harrell to take him as an intern but he was not short of energy and ambition. Diddy used to make the daily trek from Washington D.C (where he was studying at Howard University) to New York City where Uptown Records was based. EVERY SINGLE DAY. Imagine that? That’s how badly he wanted to be a part of the game.


Very few moguls have taught me about the power of ownership than Diddy. Sean Combs doesn’t do endorsements like other celebrities. If he sees a gap in the market he will develop a product, build the brand and create a distinct lifestyle around it. He will then own that brand outright (or have a major stake in it) and will promote it ceaselessly until it blows up.

Be sure, it’s a very risky trajectory he has chosen but is this not what entrepreneurship is about? Where people run out of a burning building we go straight in with the goal of turning things right around. Risk is part of the game but with experience you learn how to cleverly mitigate it and insulate yourself from potential losses when things go south.

Like Berry Gordy before him, Diddy did not only shape the sound of an era but he built a business and brand worth hundreds of millions of dollars in the process. A brand that is profitable and that evokes sincere emotions from legions of followers. Every time a song from the 90’s or 00’s comes on and you hear “BAAAAAAD BOOOOOOOY” in Diddy’s cracking voice goosebumps engulf your body and what follows is usually a Harlem Shake or the Diddy Bop. Diddy made us dance but he also motivated us on every other record that he did. Diddy rarely passes on an opportunity to unleash one of his trademark rants that can light up a fire up your ass.

Like he always says, “I’ve been sent here to inspire you”.

Just like I did with Jay Z, I’ve taken the time to distill 10 powerful business I have learned from the great Sean “Diddy” Combs. Here are the first 5 (the rest to drop on Monday):

Fail Forward:

A lot of people don’t know this but back in his varsity days when he was still called Puffy, Diddy had to overcome a tragic incident that would have killed the spirit and motivation of an average joe. While at Howard, Diddy was known for throwing amazing parties (yes, he’s always been that guy!) that every kid at varsity clamoured to attend. In 1991 Diddy hosted a concert at the New York City Gymnasium headlined by the late Heavy D. The event was overcrowded as it was sold to almost double its capacity so several thousand people were stuck outside. With everyone pushing and trying to getting in a stampede ensued and 9 people lost their lives on that tragic day. The event made headlines across New York City. He almost went to jail. This was exactly 3 years before Diddy launched Bad Boy Records. Many would have forgiven Diddy for giving up after such a tragic setback but after settling the matter with the authorities Diddy picked himself up again and went on to make history.


Diddy is Diddy, unapologetically so. Diddy danced his way through every one of his artists’ videos and concerts and may labelled him corny as a result. Diddy’s dancing famously got ridiculed by Suge Knight, founder of Death Records at The Source Awards. “Any artist out there that want to be an artist and stay a star, and don’t have to worry about the executive producer trying to be all in the videos, all on the record, dancing… come to Death Row!”

But what Suge Knight failed to understand is that Diddy actually genuinely loves dancing. It’s his thing. He is being himself. He doesn’t care that the hip hop audience finds it corny. 22 years later after that speech was made Diddy is till shimmying away in videos while Knight is locked up serving a long term prison sentence. Ha!

“If you dream and you believe, you can do it” – Diddy

Reinvent Yourself:

Diddy is the Master of Reinvention. Over the years he’s gone from Puffy to Puff Daddy to P.Diddy to just Diddy. When the biggest star on his label was gunned down in cold blood in 1997 he didn’t panic. As if he had been preparing for this moment for years he simply took off his shiny suit, got into the studio, grabbed a mic and recorded No Way Out alongside Mase, Lil’ Kim, The Lox and many others. That album went onto sell more than 10 million records worldwide (7 million in the U.S alone)  and spawned one of the most successful hip hop tours of all time. The lesson here is that the universe will throw you plenty of challenges (this is guaranteed), it’s up to you to decide how you respond to them. Diddy responded by getting out of his comfort zone (record label head) and becoming the artist.

Partner up with the Big Boys:

Diddy is a really talented businessman and marketing whiz but he hasn’t done it on his own. He has been clever enough to know that even he needs partners especially the kind that posses worldwide infrastructure and distribution prowess. With Bad Boy Records, Diddy went into a 50/50 joint venture Clive Davis’ Arista Records. Arista gave Diddy a huge advance which he used to launch the careers of the Notorious B.I.G and Craig Mack. On top of that Arista distributed and marketed all of his records to a global audience whilst Diddy focused on what he knew best – making hits. The same model applies now with Ciroc. Diddy has a profit-sharing deal with Diageo, owners of Ciroc, who pay him royalties based on cases sold every year. They produce and distribute the product globally whilst Diddy focuses on the marketing. This is  a crucial lesson for start-up entrepreneurs. When you have built enough leverage partner up with a bigger company that will bring assets that you might not have. You’ll realize your goal faster.

Be a Paper Gangster:

Diddy is not a gangster in the criminal sense. Many in the industry have described him as a paper gangster because of how on point his contracts are (to his benefit). From day 1 Diddy has always armed himself with a litany of litigators and entertainment lawyers (because Mo Money, Mo Problems). If you know how shady the entertainment industry can get you’d realize how this is a prerequisite and not an option. Diddy’s contracts are so water-tight he’s managed to fight off everyone from The Lox to Mase and plenty of other executives who wanted to either get out of their contracts or screw him over in a deal. Many have called Diddy evil but he’s just being a smart businessman. You should never lose the leverage in business and part of how you maintain that is by having excellent paper work that protects all your intellectual property and assets.

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