Sean "Diddy" Combs, the charismatic force behind the rap empire and a billion-dollar fortune, attracted the attention of the ultrarich with his innovative business proposals. Over the years, while he got accolades from billionaires and Wall Street elites, there have been federal investigations over the sex trafficking allegation, leaving his entrepreneurship in a bit of uncertainty.

Diddy's mental vision of big-time billionaires—so real that he was practically counting their money—linked him to people like billionaire Ron Burkle and hedge-fund guru Ray Dalio, giants in the investment world. His deals have been across all kinds of sectors, from fashion with Macy's to partnerships with alcohol giant Diageo and tech magnate Marc Benioff.

Outstanding was his daring manner of emailing Mark Cuban about designing uniforms for the Dallas Mavericks, leveraging his association with the Sean John clothing brand in pro sports. This strategic rapper's negotiations resulted in him receiving significant respect, particularly from Diageo for Cîroc vodka in Hollywood.

But with success, he also had a fair share of controversies—accused by ex-Cassie of serious allegations, Diddy had to face public scrutiny, which resulted in brand dissociations: Macy's stopped the sales of the fashion line, and several companies left his Empower platform.

Diddy's brand faces legal battles and reputational damage. The message and products come to mind. But still, the impact is there, felt within the business environment, as his ventures have molded industries and inspired future business people.