Nasir Jones, the Grammy-nominated rapper, entertainer, entrepreneur, and burgeoning venture capitalist—who’s gone by monikers like Nasty Nas and Escobar but has for over two decades been known simply as Nas—sips tea in a secluded studio on a warm spring day in Los Angeles.

He’s just spent the better part of the day diligently recording voice-over tapes for Hennessy, the French luxury cognac house whose liquor he’s been referencing since he was a 20-year-old kid from Queensbridge, Queens, New York.

That kid grew up fast, skyrocketing to hip-hop stardom off the strength of the seminal Illmatic, the first of 10 studio albums that would chart his life through his art, and vice versa. But while countless rappers have waxed poetic about hip-hop’s favorite liquor over the years, few have shrewdly made moves to capitalize on it by partnering with the company.

Nas officially joined forces with Hennessy as a brand ambassador in 2013, repping their Wild Rabbit campaign, and has re-upped every year since. This year’s push highlights the Piccard family of explorers and adventurers, whose pursuits of excellence fits the brand profile of a legendary MC who’s cultivated a diversified portfolio of business interests even as he maintains his grasp as one of rap’s living lions.

“Hip-hop is the only musical genre or musical style that speaks about what we like,” Nas offers. “We’re the only ones that tell you what kind of car we like to drive, the neighborhood and the type of homes we like to live in, the watches we wear, the food we eat, and the drinks we drink.”

He ponders why it is, exactly, that rappers mention a 250-year-old cognac quite so often in their songs. “We do it for free,” he laughs. “But it’s not really for nothing, because we’re happy to. We’re like Yelp. We’re better than Yelp and we came before Google. It’s just hip-hop!”

Rap’s most introspective street’s disciple turns pensive. “When I think about it, I think about life. It’s funny how things you never thought would become reality,” he muses. “If I had gone a different route, maybe I wouldn’t have done half the things I’m doing today…”

People often ask Nas, now 42, to weigh in on the state of rap these days. He’s not one to take easy shots. But as a member of the old guard, many of today’s pop rappers were either in diapers or not even born when Nas burst onto the scene in the ’90s and put New York City hip-hop on the map again.

“A lot of people before me in the civil rights era or business people who came before me, they didn’t see this revolution of hip-hop music coming and they missed out,” he says. “Some people who were a part of the ’60s and ’70s movements, they didn’t identify with the youth anymore and they lost out because of it.”

“Today’s music represents today’s young generation, good or bad. Whether we like it and whether we agree or not, it’s their truth,” he continues. “It’s what they’re being fed. It’s what they’re being taught. It’s what they see. And they’re giving it back to us. I feel like it’s their honesty. And a lot of it is marketing, a lot of it is show business, a lot of it is fluff, a lot of it we could do without. There’s some good stuff out there by a younger generation than myself. I’m just happy to be here, to listen to the youth, and to make my own mind up about what I want to do today.”

Nas, more than many MCs of his generation or subsequent ones, has always been one to pour deeply personal musings into his music. You can pick up any Nas album and hear which era of Nasir Jones was spitting into the mic.

“I will say that I’m one of the two or three guys who brought the vulnerability and lyrics to today’s rap game,” he says, analyzing the style that’s marked every era through 2012’s Life Is Good, the last studio album he released. “And I hate saying that. I don’t want to sound like I’ve got an ego, that’s not where I’m coming from. But that’s been my thing, you know, since I’ve been doing it.”

“There are different kinds of people out there, and one person might relate to this record and another person might relate to that record.” He pauses, searching. “I like to write for different parts of the human spirit. You know what I mean?”

In the last decade alone fans have seen Nas reveal striking shifts in his perspective as an artist through his musical output, from 2006’s Hip Hop Is Dead to the controversial 2008 Untitled album. Nas looks back on those last 10 years.

“Hip Hop Is Dead is how I felt musically about music, and the Untitled album was how I felt, if you will, politically,” he explains. “The next one, Life Is Good, was more about me. Me—the person.”

“When you put part of your wife’s wedding dress, the part you left behind in the house, on the album cover,” he adds with a wistful smile, “that’s personal.”

He’s popped up recently on other artist’s songs while continuing to work on his highly anticipated next album, the one that’s been a few years in the works—to his fans’ frustrations. In January he featured on Future’s “March Madness” remix proclaiming his own “icon status” as “hip-hop’s baby dad” while throwing Hennessy a little shoutout (“Nas pour Henny / Future pour Dirty Sprite”).

He also teamed with Usher on last fall’s “Chains,” a blistering track about police brutality that marked the singer’s foray into politically conscious messaging in the Black Lives Matter era.

“That was his first time doing something like that and I was happy that he called me to assist him in walking into that world,” says Nas. “Being aware of what’s happening around you, of what’s happening in society… it’s a travesty. I was proud of him to see him do music like some of the guys who came before, like Marvin Gaye, who was not afraid to speak about what was going on in the world, because he was concerned about people.”

“I mean, I live here,” he adds. “I don’t live on Mars. I live here with everybody else and it’s not like I’m not right here. I see what’s happening.”

If Nas’s upcoming 11th studio album has been a few years coming, it’s because he’s been busy building a sprawling mini-empire of business interests. There’s his ownership stake in urban media label Mass Appeal, the sneaker and apparel store he’s opening in Las Vegas, the line of lip products he launched with his daughter, and his restaurant business venture with NYC soul food joint Sweet Chick, with plans for expansion to L.A. Most intriguing, Nas launched a venture capital firm—QueensBridge Venture Partners—which has invested in over 40 start-ups in tech, healthcare, Bitcoin, and companies like Lyft, Dropbox, Genius, and Tilt. In an interview with CNBC, Nas’s manager and QueensBridge partner, Anthony Saleh, said that the firm typically invests between $100,000 to $500,000 in a start-up, and helps fund about 20 companies a year.

“I signed a new deal on another venture today,” Nas smiles. “Just now! I took a five-minute break to sign a contract for a whole other thing. It’s too early to talk about but I’m really excited. I’m constantly moving.”

“But I can’t lie,” he admits. “That stuff has gotten in the way of my music. But it’s all about balancing everything out. I don’t want anything to be done half-assed, so everything has to get its proper attention. And now the music is getting its proper attention.”

After hitting the stage at SXSW in March, Nas dropped his full J Dilla collab The Diary and joined pal Killer Mike at last week’s Run the Jewels set at Coachella. At the time of our chat, he still hadn’t decided between two titles for his upcoming album—but Nas says he’s taking his time, letting his next major musical statement unfold organically.

“It takes time to do it because I’ve come from different moments in rap music where I was a part of the shifting of the whole thing,” he admits. “And once you’ve made those kinds of impacts on the music, you don’t always want to do too much of the non-thinking. You want to do something that adds onto what you’ve been building all these years.”

“I have to be excited about it. It has to mean something to me, more than just a record. It has to mean a lot of things to me. I don’t know if that’s a Virgo thing.” He laughs. “That should explain a lot, right? We’re sort of perfectionists and over-thinkers.”

“I’m working feverishly,” Nas insists, “and I’m working more than I have been [on the album] than I have in the last year or two. I’m working a lot more, because there’s something about this year. There’s something about it.”

His next album, he hints, is about “myself as a man, a thinking man.” He describes it as the next chapter, a progression from his Life Is Good—which was, after all, a deeply personal album written after his 2010 divorce from singer Kelis, who was at the time pregnant with their son, Knight.

“I can’t look back at anything,” Nas declares. “I have great moments in my life that I’ve forgotten about. I’m constantly trying to do exactly what I’m supposed to be doing, at this day and age, at this point in my life, and not looking backwards at anything.”