Sitting in the living room of his European-style villa in Beverly Hills, Sean “Diddy” Combs is eager to speak about an entire galaxy of issues. He wants to talk about “The Four,” the Fox singing competition show bearing his imprimatur as both producer and star judge. He’s antsy to delve into the past and future of Bad Boy Records, the hip-hop and R&B label that he founded and built into a game-changing powerhouse back when he was the world’s flashiest twentysomething A&R man. He wants to discuss his various business ventures, which span everything from fashion to spirits and bottled water to cable network Revolt TV.

But at the forefront of his mind, and fueling his passion, are the hot-button topics of race and the central paradox of modern African-American enterprise — in which black popular culture is as ubiquitous as ever, yet so many old obstacles to black financial autonomy remain in place.

At 48, Combs, who for two decades has been one of black America’s most visible and successful business figures and has been dubbed the richest musician for several years running, is trying to take stock of what his accomplishments mean — and what the culture that enabled his success still has to overcome.

“You have these record companies that are making so much money off our culture, our art form, but they’re not investing or even believing in us,” says Combs of hip-hop’s commercial dominance, especially through streaming.

“For all the billions of dollars that these black executives have been able to make them, [there’s still hesitation] to put them in the top-level positions. They’ll go and they’ll recruit cats from overseas,” he continues. “It makes sense to give [executives of color] a chance and embrace the evolution, instead of it being that we can only make it to president, senior VP. … There’s no black CEO of a major record company. That’s just as bad as the fact that there are no [black] majority owners in the NFL. That’s what really motivates me.”

Combs is unsparing about the music business landscape in which he came of age (“There was segregation, as well as blatant racism, and there still is”) and the film business’s baby steps toward inclusion.

“‘Black Panther’ was a cruel experiment,” he maintains, “because we live in 2018, and it’s the first time that the film industry gave us a fair playing field on a worldwide blockbuster, and the hundreds of millions it takes to make it.”

For Combs, harnessing the means of production is the only way forward — and the organizing principle of his various businesses.

“We only get 5% of the venture capital invested in things that are black owned — black-owned businesses, black-owned ideas, black-owned IP,” he says. “You can’t do anything without that money, without resources. But when we do get the resources, we over-deliver. When Adidas invests in Kanye and it’s done properly, you have the right results. When Live Nation invests in artists and puts them in arenas the same way U2 would be, you have the right results. ‘Black Panther,’ ‘Black-ish,’ fashion; it’s all about access. If you’re blocked out of the resources, you can’t compete. And that’s my whole thing — to be able to come and compete.”

Combs has given himself new sobriquets almost as often as he’s launched new businesses, with Puff Daddy, Puffy, Diddy, and Love being only a few of his past and present aliases. One thing that’s remained consistent, however, is his preternatural talent for working the angles. Madonna and U2 manager Guy Oseary first met Combs at the launch party for Bad Boy’s debut artist, the late Craig Mack, back in the mid-1990s. Oseary notes that Combs’ outsize ambitions, and knack for making offers in the least refusable manner possible, were obvious from the start.

“From day one, he was an entrepreneur,” he says. “He was always hustling, always on a mission.” Oseary remembers getting a call from Combs in 2003 when he was training to run in the New York City Marathon, through which Combs raised $2 million for New York public schools and children’s charities. “I picked up the phone, and he said, ‘Hey Guy, how much are you gonna give to support my marathon? And by the way, we’re filming this.’” Oseary laughs. “He’s on the other end with a camera.” Minutes later, Oseary got a ring from Chris Rock, who revealed that Combs had made him a similar call and convinced him to match Oseary’s pledge, without telling him the amount.

Robbie Fimmano for Variety

But Combs certainly presents as an older, wiser version of the wrecking-ball force of nature he was in Bad Boy’s heyday. As passionate as he might get, he exudes a combination of focus and calm in conversation, and he’s taken to espousing a philosophy of “We, not me.” Last year, he appointed longtime staffer Dia Simms, who started as his assistant in 2005, as president of Combs Enterprises and its 200-plus employees across multiple brands — the first time day-to-day business of his empire has been overseen by anyone not named Sean Combs.

As Simms’ first order of business, she sought to make the company “a hater-free, no-asshole zone.” In an interview, she tells Variety of her boss: “As long as I’ve been here, he’s been enormously focused in being the best man he can be and also the best brand, forgive my rhyme. But it’s not accidental, and it’s not a cliché.”

Fergie, who serves as host of “The Four” alongside judges Combs, DJ Khaled and Meghan Trainor, notes: “He comes to you like a coach. And I’m not saying he’s sweet as pie — he commands your attention, and he’s a presence. And sometimes that’s not all saccharine and sweetener. You’ve gotta be tough, and you’ve also gotta be tough love, and it’s interesting to watch as he switches from one to the next.”

While the structure of “The Four” doesn’t diverge much from that of predecessors “American Idol” and “The Voice” — fresh-faced hopefuls perform and share inspirational stories; celebrity judges offer extravagant praise or brutal critiques; audiences vote on winners — Combs’ primary demand when setting the show up at Fox was that the full breadth of the pop radio landscape (particularly hip-hop and Latin music) be reflected in the contestants and song selections.

“Me and Puff said there wouldn’t be a show unless there was hip-hop involved,” says Khaled. “We’re on the same page with that. One thing I know with Diddy is it’s gonna be right. If he wasn’t with me here, I’d make sure it’s right, but since he is here, it’s really right.”

Fox Television Group chairman and CEO Dana Walden adds: “Sean was a must-have for us, because not only is he a superstar and an icon in the music business, but he also has tremendous credibility in artist discovery and development. There’s no one better at what he does, and he’s always looking to break new ground. So this is a perfect fit for him.”

During the first season of “The Four,” Republic Records president Charlie Walk served as the fourth judge, only to step down from both positions after allegations of sexual harassment surfaced. Asked about the scandal, Combs says: “I’m not gonna be anybody’s judge and jury. But I will say that nobody should feel like they’re getting taken advantage of or getting abused when they’re just trying to create a livelihood for themselves.” He adds: “There are a bunch of injustices going on, and the same fire and vigor that people have about the #MeToo movement, I think it’s time that they have that about the way black America has been treated too.”

“In my early days, we would’ve never sold anything except music. If not for guys [like Combs], I never would’ve even thought about doing something like Beats.”

Jimmy Iovine

Getting a TV series off the ground is hard enough, but Combs is embroiled in an even loftier challenge: an entire cable network. Revolt TV was launched five years ago, one of a handful of black-owned cable nets in the country. According to Simms, the network currently boasts a 40 million household reach. Its mission is straightforward, says Combs: “The African-American voice is the No. 1 voice being heard and digested by the world; Revolt brings an unapologetic view of that.” In other words, it’s an embodiment of Chuck D’s famous description of hip-hop as “the black CNN.”

But with the subscription-TV business in a cord-cutting-spurred state of turmoil, the launch hasn’t been frictionless. The network underwent an executive shuffle over the past year — adding Roma Khanna as CEO and Robyn Lattaker-Johnson as head of content — and experienced layoffs last month.

Combs says that the platform was built to roll with the punches. “I want to be perfectly clear: Revolt is not just a cable television network; that never was the plan,” he explains. “We were always social by design — multiplatform. People try to put it in boxes, and it’s not gonna be that. It’s gonna jump on your phone; it’s gonna be on all your screens. Linear cable is not the future; the future is in the actual brand being a multiplatform provider of premium content.”

Combs habitually brings the conversation back to matters of black enterprise, and seems particularly haunted by a catastrophic race riot that devastated an Oklahoma community back in 1921.

“I think a lot about Black Wall Street,” he says, referring to the Tulsa neighborhood of Greenwood, where black entrepreneurs once built a robust local economy, only to have it all destroyed by a white mob. “The black people in this community were thriving, and others were having to look at them thriving because they had their own banks and supermarkets. Income was being cultivated, and they were having a lot of success. And so the white mob burned the town, lynched people to send a psychological message. And it worked. The message was, if y’all come together, if you thrive, this is what’s gonna happen.”

Riding in a town car through Culver City, one of the many once-affordable L.A. neighborhoods to recently fall victim to rapid development and rent increases, Combs thinks back on the changes that have taken place in his home neighborhood of Harlem.

“Gentrification is heartbreaking,” says Combs. “When I go back to New York, the energy doesn’t feel the same — the nightlife, the excitement, the provocativeness. In Harlem you still feel that, even though the community has gotten displaced and shrunk. Like, where are the black people at?”

Combs’ entrepreneurial origin story has been told so many times it’s practically calcified into music industry myth. Raised by a single mother in Harlem and Mt. Vernon — his father was murdered when Combs was a toddler — the 11-year-old Combs lied about his age to secure a paper route, then took part in the grade-school version of a corporate acquisition when he offered other neighborhood kids a cut of his earnings to take over their routes too. Those Harlem roots inform everything Combs went on to accomplish.

“It’s a beautiful place to grow up,” he continues. “You’re empowered by knowing your history. You can envision Malcolm X speaking on 125th, the ’20s at the Cotton Club, Langston Hughes, Harry Belafonte, Lorraine Hansberry. … There was such a deep sense of culture. When you’re born in Harlem, you’re taught how to dress nice on $5. You understand presentation, where your sneakers always have to be fresh, and the necessity of dance. … We’re just natural-born hustlers.”

Combs attended Howard University and blustered his way into an unpaid internship with Andre Harrell’s Uptown Records. After rising to an A&R position, shepherding acts like Jodeci and Mary J. Blige to multiplatinum careers, he was fired from Uptown and immediately set up his own label, Bad Boy, through Arista. With the marquee signing of the Notorious B.I.G., Combs played the part of Col. Tom Parker to the biggest player in the game, helping shape the Brooklyn rapper’s image, orchestrating wildly successful raids on the pop charts and inserting himself into his artists’ songs and videos.

Robbie Fimmano for Variety

Biggie was murdered in March 1997, a formative trauma for Combs and the hip-hop community in general, and yet Bad Boy (whose discography swelled to include Mase, Faith Evans, 112, Total, Black Rob and Combs’ projects as a solo artist) continued churning out hits at a startling clip. That year, four Bad Boy singles topped the Billboard Hot 100 chart for a combined 22 weeks, and a label-wide tour set a record as the highest-grossing in rap to that point.

But Combs was nonetheless a deeply polarizing figure in the late 1990s. To some he was seen as a shameless self-promoter and a purveyor of the materialistic, radio-baiting music that blunted hip-hop’s rawer, more revolutionary edges.

Further risking the tarnishing of his still-developing image, Combs seemed to have a penchant for grabbing headlines, an attribute that took a darker turn when he was charged with weapons violations after a New York City nightclub fracas in 1999 (he was later cleared). By then, however, he was already expanding his empire beyond the fickle limbo of pop music. His first major extra-musical venture, the fashion imprint Sean John, has proved his most influential. While Combs was not the first hip-hop figure to dabble in couture, his imprint aimed far higher than concert merchandise tables — crashing the runway circuit in Paris, partnering with Estée Lauder and eventually landing retail real estate in Macy’s stores. And unlike contemporaries like Jay-Z’s Rocawear or the Wu-Tang Clan’s Wu Wear (recent entries include Migos’ Yung Rich Nation line and Drake’s OVO), the Sean John label has stuck around.

“With fashion, to be candid, I was looking for validation,” Combs says. “And Sean John gave birth to a lot. Sean John taught Virgil [Abloh]. It taught Kanye West. It taught a whole generation of designers that come from our culture. But also Gucci learned from it, Louis Vuitton learned from it, Givenchy, Balenciaga. So much of fashion is streetwear now, and the tipping point was Sean John. … I was the first to bring street wear to the runways, and now street wear [is] a multibillion-dollar industry where people are actually looking for the talent that’s coming from the community, giving them the resources, believing in them and benefiting from that.”

Apple Music head Jimmy Iovine — who partnered with Combs while head of Interscope a decade ago — emphasizes the impact of Combs’ sartorial ventures. “It’s a much bigger deal than you think,” he says. “You look at the rock ’n’ roll world, and no one was selling sneakers, clothing lines, shit like that. In my early days, we would’ve never sold anything except music. If not for guys [like Combs], I never would’ve even thought about doing something like Beats.”

While Sean John may have been Combs’ most groundbreaking cultural expansion, his greatest financial success lay in an entirely different arena. In 2007, Combs acquired a stake in Diageo’s grape-distilled vodka Ciroc — later adding the DeLeón tequila line through the same company — and proceeded to hawk the brand with the same vigor with which he’d previously hyped new Bad Boy signings. Combs personally obsessed over details like bottle design and label font, he would confront bar managers at hot spots when he couldn’t see Ciroc sitting on the top shelf, and it’s hard to find a talk-show appearance from the past decade into which Combs doesn’t manage to shoehorn a Ciroc shout-out. But roll your eyes at your peril: According to Combs, Ciroc was a money loser before he came on board, shipping 40,000 cases annually; last year, it moved 2.6 million.

Of his five-year-old tv network Revolt, Combs says, “the African-American voice is the no. 1 voice being heard and digested by the world; Revolt brings an unapologetic view of that.”

Chris Pizzello/Invision/AP/REX/Shutterstock

As far-flung as Combs’ various brands might appear (he also has Aquahydrate, an alkaline bottled water brand on which he’s partnered with Mark Wahlberg and Ron Burkle, and he plans to enter the dark spirit business with Diageo’s upcoming brandy line, Ciroc VS), the way he approaches them all comes from the same basic instincts. “I have an eye for spotting talent and for curation,” he says. “I’m not the guy that can come up with a font, but I’m the guy who can look at a hundred fonts and say, this has to be the one.”

Given the sort of empire Combs oversees, it’s fair to ask how he manages the time to maintain a label and a recording career. Most recently distributed under Sony’s Epic Records, Bad Boy has since gone fully independent and continues to be active, with French Montana and Janelle Monáe among its biggest current artists, as well as Christian “King” Combs, one of Diddy’s six children. Combs himself hasn’t released any albums since 2010’s “Last Train to Paris,” an electro-R&B concept album that garnered some of the best reviews of his solo career yet was also his most disappointing seller.

“Musically, that was the one that broke my heart, because I knew it was dope,” he says. “But that’s part of the game. You gotta have those. Throughout your career you should do things that you really, really believe in, and take a chance.”

And despite Combs’ insistence that he doesn’t “sleep in the trophy room,” he did book an extended trip down memory lane for Bad Boy’s 20th anniversary, releasing a box set and a Live Nation Productions produced, Apple-backed documentary (“Can’t Stop Won’t Stop: A Bad Boy Story”) and mounting a full reunion tour revisiting the label’s classic material. Even the professionally unimpressed Combs felt the experience was an eye-opener.

“For me, I didn’t really understand the impact we had on music,” he says. “I understood what we did in that time but not how it continued on — that it was possible for hip-hop and R&B to mature into legacy acts, [just] like the Rolling Stones or U2 or the Grateful Dead. Onstage it was like a discovery.”

If that tour felt like a victory lap, Combs insists he’s already plotting his next act in music, one that might not look a whole lot like the first.

“I feel like we’re in a new disruptive time, and when I announce what I’m doing with music it’ll be equally as disruptive as Bad Boy was,” he promises. “My focus now is more on Revolt and on supporting other labels, other musicians. I want to go from being on the stage to actually being the stage — from being the entrepreneur to supporting other entrepreneurs, but still with that same Bad Boy attitude. Right now, I look for executive talent, creative talent, just like I used to look for rap artists and singers. It’s about me going to a new level and empowering the next generations of Bad Boy and Diddy.”