The rapper used some of Wall Street’s richest to climb up the wealth ladder.

Sean ‘Diddy’ Combs aggressively marketed himself to America’s richest businessmen as he transformed his earnings from his rap career into a billion-dollar empire.

Diddy was first declared a billionaire by hip-hop wealth expert Zack O’Malley Greenburg in 2022, but had coveted the status for years, telling Forbes in 1999, “I wanted to be very, very rich.”

He went about it by targeting some of the wealthiest men in the U.S. to invest in his various businesses.

One investor, Ron Burkle, worked with him on several projects, while he also linked up with Zac Posen, William Lauder – the heir to Estee Lauder’s brand, had a fashion line sold in Macy’s and teamed up with actor Mark Wahlberg to sell a brand of water.

Combs fancied himself as an enterpreneuer and according to the billionaires he worked with, he would cold email with business proposals. It clearly made a fine impression on Wall Street’s bigget names, with one CEO of the New York Stock Exchange called him an “inspiration”.

The deal that changed everything

In 2003, he sent an email to Mark Cuban – the former principal owner of the Dallas Mavericks NBA team – asking to design the uniforms for the team.

They had never met so the cold email was a bold move, but Cuban agreed. It was a huge boost for Combs to his new clothing brand, Sean John, to link up with a pro sports team as it expanded their profile.

“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.

Combs – who went to Howard University to study business – used the deal to leverage for even more dealmaking. But it also worked in the investors’ favor, as Combs brought them in the world of A-list parties and meeting celebrities.

Police investigating Sean ‘Diddy’ Combs

After federal investigators raided his Los Angeles and Miami homes as part of a sex-trafficking investigation led by the Southern District of New York, Combs’ reputation has taken a huge hit.

It comes after Rodney ‘Lil Rod’ Jones filed a lawsuit against Combs in February, alleging he was sexually assaulted by the ‘Bad Boys’ rapper. He has denied wrongdoing and called the probe “a witch hunt”.

It remains to be seen whether Combs will still enjoy the same level of influence in the world of business if he is convicted.