Sean “Diddy” Combs strategically promoted himself to the wealthiest individuals as he transformed his bold rap style into a billion-dollar empire. According to billionaires interviewed by The Post, Combs would reach out via cold emails with business propositions.
Additionally, he received praise from Wall Street insiders, who referred to him as a “genius,” and the CEO of the New York Stock Exchange likened him to an “inspiration” comparable to the Founding Fathers.
Following federal investigators’ raids on his residences in Los Angeles and Miami, which are reportedly part of a sex-trafficking inquiry led by the Southern District of New York, Sean “Diddy” Combs faces potential threats to his career as an entrepreneur and investor. Combs has refuted any allegations of misconduct, labeling the investigation as “a witch hunt.” Although hip-hop wealth expert Zack O’Malley Greenburg officially declared Combs a billionaire in 2022, Combs had long aspired to achieve this status, expressing his desire for significant wealth to Forbes as early as 1999, stating, “I wanted to be very, very rich.”
Along the way, he acquired a Rolodex littered with boldface names: He partnered with billionaire investor Ron Burkle; was “mentored” by hedge fund guru Ray Dalio; had his fashion line sold in Macy’s and Dillards; went into business with alcohol giant Diageo; opened the New York Stock Exchange with Estée Lauder heir William Lauder; struck deals with Zac Posen and Liz Claiborne; 50% owned his own TV channel, Revolt; launched a water range with Mark Wahlberg; and teamed up with Salesforce’s Marc Benioff to launch a black business marketplace.
In 2003, he sent then-owner of the Dallas Mavericks Mark Cuban an email asking to design the uniforms for the NBA team, Cuban told The Post. They had never, met so the cold email was a bold move.
For Diddy, it was a slam dunk to associate his new clothing brand, Sean John, with a pro sports team. While Diddy took credit for the design, it was actually Diddy’s top designer who created it and Diddy signed off, Cuban said.
“We were an up-and-coming team at a time when pro sports teams didn’t do anything with entertainment industry people,” Cuban said. “We never even met … we never did any follow-up or anything beyond that,” Cuban said.
For Diddy — who had gone to Howard University to study business — a single deal with an NBA team gave him credibility that he leveraged for even more dealmaking.
But it was a two-way street: Diddy also used his own cachet — the promise of entry into a world of celebrity — to attract investment for his projects.
The same year as his Mavericks deal, Diddy got Burkle, a serial investor worth an estimated $2.9 billion, according to Forbes, to inject $100 million into his fashion range Sean John.