How Diddy got to be one of hip-hop's biggest businessmen

• Federal officials raided homes belonging to Sean "Diddy" Combs on Monday.
• The hip-hop mogul is one of the most successful businessmen in  the industry.
• He's amassed a fortune that was at one time valued at $1 billion — and power to match.

Federal officials raided the Los Angeles and Miami homes of Sean Combs on Monday. The action by Federal Homeland Security Investigations is part of an ongoing sex trafficking investigation, the AP reported.

While the target of the raid has not yet been identified and Combs has not been arrested as of Tuesday, it was the latest and most serious event in ongoing legal troubles facing the music mogul, who is best known as Diddy. Over the past five months, sexual assault and misconduct allegations have piled up against him.

In November, an ex-girlfriend of Combs', Casandra Ventura, filed a lawsuit accusing him of sexual assault and abuse during the 10 years they dated. Combs denied the allegations and Ventura, known as Cassie, settled with Combs a day after she filed the lawsuit. Still, additional women soon came forward with their own allegations of rape, sex trafficking, and sexual abuse. In February, music producer Rodney Jones Jr., also known as Lil Rod, filed a lawsuit accusing Combs of groping him and forcing him to perform sexual acts with sex workers.

Combs has denied all the prior allegations against him. In response to requests for comment from Business Insider following Monday's raids, his attorney Aaron Dyer said in a statement:

"Mr. Combs was never detained but spoke to and cooperated with authorities. Despite media speculation, neither Mr. Combs nor any of his family members have been arrested nor has their ability to travel been restricted in any way. This unprecedented ambush — paired with an advanced, coordinated media presence — leads to a premature rush to judgment of Mr. Combs and is nothing more than a witch hunt based on meritless accusations made in civil lawsuits. There has been no finding of criminal or civil liability with any of these allegations. Mr. Combs is innocent."

Diddy operates in a world of extreme wealth. In the three decades since he started Bad Boy Records, the 54-year-old has amassed more money than nearly any other hip-hop artist. He pioneered a business playbook that has been followed by many other successful musicians and became an industry gatekeeper — giving him power that several of the people suing him accuse him of using to cover up his abuse.

Records, fashion, liquor: Combs pioneered the hip-hop money-making playbook.

In 1993, Combs, then known as Puff Daddy and Puffy, founded Bad Boy Records after a stint at Uptown Records.

The label soon became the place for East Coast hip-hop acts emerging on the scene. He signed Craig Mack, 112, Faith Evans, Mase, and Notorious B.I.G. Combs' own 1997 album "No Way Out" reached platinum status seven times over.

In its heyday, the label brought in $130 million annually — enough that Combs could negotiate a $55 million personal advance in 1998 from Bad Boy's partner, Arista Records, Forbes reported in 1999. Until he returned the publishing rights to some of Bad Boy's artists last year, Combs was personally earning millions from the Bad Boy catalog each year.

Music was only the beginning. By the late 1990s, Combs was paving the way for what would become the business path for many future musicians.

He started with Sean Jean, a line of clothing, furniture, and fragrances sold at stores like Macy's and Dillard's. It became a consistent source of revenue for the mogul.

While the brand's cache eventually dwindled — he purchased it back for only about $7.6 million in 2021 — Sean Jean enjoyed more than a decade of success. In 2016, when a majority share was sold to Global Brands Group, it was reported that the brand had retail sales of $450 million and that he pocketed $70 million.

Combs' most lucrative endeavor came in 2007 when he became a brand ambassador for Ciroc vodka. He struck up a unique deal with Diageo and got paid per case.

Within the first two years of the partnership, annual sales grew from 75,000 to 400,000 cases, according to a lawsuit Combs filed against Diageo last year. In 2014, it sold 2.6 million. The liquor giant doubled down on Combs, announcing in 2014 that they'd bought DeLeon tequila in a 50-50 partnership.

While Combs and Diageo parted ways earlier this year after a contentious legal battle, the company did give some insight into Combs' total earnings in a court filing last year: He'd made nearly a billion dollars throughout their 15-year partnership.

He's invested that money in other upstarts, launching the Revolt TV cable network in 2013 and teaming with Mark Wahlberg to purchase a majority stake in water company Aquahydrate.

"At the end of the day, the numbers don't lie," he told Forbes that year. "I'm just like any other businessman; at the end of the year I have to get my report card and deal with the reality of whatever it is."

In 2022, Combs was labeled a billionaire for the first time.

In 1999 interview, Combs told Forbes that he "wanted to be very, very rich."

That's exactly what happened. By 2022, Combs' net worth had reached $1 billion, according to Zack O'Malley Greenburg, the author of the Jay-Z biography "Empire State of Mind," who tracks hip-hop's wealthiest musicians.

And while that figure has likely fallen over the past year — he's given up the publishing rights for Bad Boy's artists, and his deal with Diageo has been dissolved — his wealth is still massive.

Combined, he's earned well over $1 billion, pretax, from the Ciroc deal, his record label, and Sean Jean. Some of that is tied up in various investments — including less-than-successful ones, like Revolt TV — while a significant amount has been spent on a life of luxury and various toys. He owns a jet that costs eight figures, over $1 million worth of jewelry, and a collection of art that includes a $21 million painting by Kerry James Marshall and works by Andy Warhol, Keith Haring, and Jean-Michel Basquiat.

His real estate portfolio includes immense properties in Los Angeles and Miami, worth $46 million and $36 million, respectively, according to county assessments.

While building his empire, Combs amassed "dangerous" power.

Combs has accumulated a combination of wealth and influence from his various business endeavors.

That has made him "immensely powerful, and immensely dangerous," Ventura's attorney wrote in her complaint against Combs.

He "used his money and power to orchestrate extensive efforts to hide the evidence of his abuse," the complaint continues.

The complaint alleges Combs "lured" Ventura into his circle, using his position as the head of Bad Boy Records. Ventura said after the abuse started, Combs used his money and power to hide it.

She was often afraid to fight back or speak up, knowing he had a powerful network who would defend him, according to the complaint.

"There was no one she could tell about what had happened at the hands of this incredibly powerful man," the complaint says. "She recognized that she was powerless, and that reporting Mr. Combs to the authorities would not alter Mr. Combs's status or influence but would merely give Mr. Combs another excuse to hurt her."

In a separate lawsuit filed in November, Joi Dickerson-Neal alleges that Combs drugged and assaulted her in 1991.

When, at the time, she tried to take legal action, "colleagues told Plaintiff that they were terrified that Combs would retaliate against them and that they would lose future business and music opportunities if they made a statement in support of Plaintiff, as Combs' star was on the rise in the 1990s," the complaint says.

Yet another lawsuit, filed in December by an unnamed woman only identified as Jane Doe, accuses Combs of using a private jet to aid in the sex trafficking and gang rape of a high school student.

With the feds storming his properties and allegations mounting, it seems as if Combs' reign as a hip-hop powerhouse may be coming to an end — in part due to the lawsuits.

Following the claims of sexual assault, Combs stepped down as Revolt's chairman and has reportedly sold his shares. Hulu canceled a reality show about his family.

And the lawsuits are coming after more than him and his personal cash stash: Four of them name Bad Boy or Combs Enterprises as defendants.