Here's how Sean 'Diddy' Combs built his $885 million empire

From an intern and A&R at Uptown Records in the early 1990’s to a billionaire thirty years later Sean “P. Diddy” Combs’ career trajectory has been nothing short of staggering. In an era when hip-hop has produced a spate of billionaires — a few from Jay-Z’s tutelage — Rihanna, Kanye, not to mention Jigga himself (Dr. Dre hit a home run with one product — Beats) — P. Diddy seems to have been around for an age because he did it all first. The first to have his own label, the first to branch out into beverages, the first to start a clothing label, and the first to become a restauranteur. Now he’s at it again, buying a massive marijuana business that the Wall Street Journal first reported is worth up to $185 million.

In the 26 years since California legalized the use of medical marijuana, the cannabis trade has grown to a legitimate $27 billion business. If US and state regulators give P. Diddy’s venture the green light, it will create the country's largest Black-owned and licensed cannabis company. In a largely white-run business, which is expected to reach $42 billion in sales by 2026, Black people have disproportionately been arrested for marijuana crimes in the past. Combs' purchases aims to redress the balance. 

"It's diabolical," Combs told the Wall Street Journal. "How do you lock up communities of people, break down their family structure, their futures, and then legalize it and make sure that those same people don't get a chance to benefit or resurrect their lives from it?"

The deal includes Combs' company acquiring nine retail stores and three production facilities from Cresco Labs Inc. and Columbia Care Inc., two of the largest cannabis businesses in the U.S. in New York, Massachusettes, and Illinois with an initial outlay of $110 million in cash and $45 million in debt financing. Additional payments will be made based on growth milestones. 

Though this marks the largest Black-owned marijuana deal, it's not the only one. Fellow rapper/entrepreneur Jay-Z (Sean Carter) created a fund as part of his Marcy Ventures to invest in minority-owned cannabis startups.

Here's a look at the other business ventures Combs has been involved in over the years to help him attain his current billionaire status.

Bad Boy

Combs was one of the hip-hop's first entrepreneurial moguls with his own record label, Bad Boy, then a fashion label, Sean John, a series of restaurants, followed by a move into the alcohol business with Ciroc Vodka, and Revolt TV which skyrocketed his fortune. However, it was undoubtedly Bad Boy, that launched Puffy, as he was then nicknamed, the mogul, and gave him the gravitas to launch his other businesses. 

At its height in the mid 1990s with artists such as Craig Mack, 112, Faith Evans, Mase, and the iconic songs of Notorious B.I.G. the label was worth $100 million. It lost its luster and the hits dried up as Diddy diversified out of the music business. After a co-venture with Warner Music, the label signed a distribution deal with Epic Records in 2015 but has largely been dormant in recent years.

Sean John

In the latter 1990s, it seemed it was impossible to go anywhere without seeing someone in a Sean Jean T-shirt or jeans. With a flagship store on Fifth Avenue and celebrity endorsements, the clothing company was on every street in every city. Ever the savvy businessman, Combs sold his controlling stake in Sean John in 2016 for a reported $70 million. However, in late 2021, Combs bought back his streetwear brand for $7.5 million out of bankruptcy from Global Brands Group to regain total ownership, WWD reported.

"I launched Sean John in 1998 with the goal of building a premium brand that shattered tradition and introduced hip-hop to high fashion on a global scale," Combs said in a statement. "Seeing how streetwear has evolved to rewrite the rules of fashion and impact culture across categories, I'm ready to reclaim ownership of the brand, build a team of visionary designers and global partners to write the next chapter of Sean John's legacy."

Cîroc

In a somewhat controversial move at the time, Combs entered the crowded beverage business by becoming an ambassador for the vodka company Cîroc in 2007. As part of a 50/50 partnership, he helped revenue explode in one year from 40,000 cases to a million cases. The deal was reported to have netted the mogul over $100 million and continues to be a lucrative source of income estimated to be in the hundreds of millions. 

Revolt

According to Business Insider, Combs formed Revolt TV in 2013, a deal that pushed up his net worth by $200 million, increasing his total net worth that year to $580 million. As the company's majority shareholder, a deal with Time Warner Cable gave the company an immediate 25 million subscribers when it debuted. 

Other Notable Deals

• Combs reportedly received $28 million from MTV in 2007 for his influential "Making of The Band" series. 

• In 2014 he and Mark Walhberg teamed up to launch Aquahydrate. After a $20 million investment from the two entertainment figures, the company was generating $65 million in sales per year by 2020. 

• In 2014, Combs announced a 50/50 partnership with DeLeon tequila in a partnership with British drinks multinational Diageo, with whom Combs is already in business through Cîroc.

• Combs also owns a super yacht called Maraya which he purchased in 2012 with a value of $65 million.

• He also owns a private all-black Gulfstream G550 private jet worth $60 million.

His sprawling business empire has reportedly made Diddy a billionaire this year. In addition to his businesses, he owns a sizeable real estate portfolio of personal homes, as well as cars and jewellery. He also recently invested $10m to back Elon Musk's buyout of Twitter. Like fellow mogul Jay-Z, he has dabbled in art, spending $21 million on a Kerry James Marshall painting called "Past Times" in 2018. It was the highest-ever paid-for-a-living Black artist.

Conclusion

A knack for business, and marketing with an ear to the street, earmarked Sean Combs' success in the music business 30 years ago. Since then, he has brilliantly leveraged his visibility as a cultural icon, breathing life into stagnant brands, and making himself a billionaire. 

There are only a few people who can pull it off. Jay-Z, who has a notably more reserved public persona than Combs, is the other. If there is any one aspect of Combs' personality that helps define his success, it's a complete and total self-belief in his ability. In Combs' case, his confidence has proven contagious.