Chamillionaire at Upfront Ventures. Photo by the author.

It’s a sunny afternoon in Santa Monica, and the Houston rapper Chamillionaire is making himself comfortable in an airy conference room where piles of money are routinely doled out and negotiated over. We’re on the fourth floor of the temporary offices for Upfront Ventures, an investment firm valued at $280 million. If you look outside you can see palm trees poking up in the distance and the blue spread of the Pacific Ocean beyond that. Cham’s sitting in a swivel chair, resting his elbows on a frosted-glass table, angling forward as he explains to me the difference of being “rich” vs. being “wealthy.”

“I walked around the music industry for a bunch of years, right? I saw a lot of rich people. I didn’t see wealthy,” he tells me. “I got into the tech industry, I see wealthy every day. The Snapchat CEO is 24 years old and a billionaire. How many billionaires do I have to walk around the music industry to find? I’m in Silicon Valley, I’m in L.A., I’m in Santa Monica, and I’m seeing billionaires all over the place. And they’re young. That’s not in the music industry.”

Right now, the 35-year-old born Hakeem Seriki is rich. But he’s aiming to get wealthy. That’s what brought him to Upfront Ventures. Since March he’s been heading here every week—alongside his producer Nsilo Reddick—to serve as the firm’s new “Entrepreneur in Residence.” In the world of venture capitalism, an “EIR” is a relatively loose, informal and temporary position—basically an opportunity for an entrepreneur to work with an investment team and get some capitalist know-how as they plot out their next project. In Cham’s case, he says he doesn’t have specific office hours; he’s free to come and go as he pleases. Mostly he just sits in on meetings and takes notes as leaders of various companies and start-ups come in to this very conference room we’re sitting in to pitch their ideas to Upfront’s partners—with the hopes of walking away with a term sheet promising anywhere from $1 to $10 million in seed money.

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The experience has been quite an educational one for the 35-year-old big name of the mid-00s Houston rap explosion, who’s otherwise known as King Koopa. Though he declines to name who’s been coming in, Cham says visitors include scientists, Ivy League graduates, people who have brilliant ideas and “people who are just winging it.” Essentially it’s a grab bag of people touting projects Upfront might be interested in getting a piece of—something that could prove to be a total flop, or could just as well end up as the next Uber or Snapchat.

“There are people that are doing things that I would’ve never even thought possible,” says Cham, who’s giving his first interview about the EIR since it was announced in February. “To be in the midst of that is just amazing to me. Coming up as a rap artist, man, I come from a world where people couldn’t just walk into a room and just get all this money. You had to be a rapper or a basketball player and you had to be exceptionally great at that.”

So, uh, why exactly is Chamillionaire chilling with VCs these days? The answer is simple—money. Also, power, influence and equity. He’s dunzo with the traditional workings of the music industry. In recent years he’s seen the tech world swoop in and take major chunks of the pie with companies like Apple and Spotify, and now he wants his cut. Yep, Chamillionaire has seen the road to becoming a Chabillionaire, and it’s paved in tech dollars.

“Your Facebook page you’re posting all on—how much money are they making off your page? Do you know?” he says. He’s looking understated but fresh in a black hoodie, chunky diamond earrings and long gold chain. “Most people don’t know, or don’t care to know. I’m one of the people that kinda wants to know.”

Cham has always been a business-minded fellow, but he’s come a long way over the years. He got his start on legendary Houston label Swishahouse in the 1990s, roving from city to city, record store to record store, and selling mixtapes out of his Ford Excursion. He eventually left Swishahouse and in 2002 he got on the national rap radar with he and Paul Wall’s Get Ya Mind Correct, a loving ode to candy paint, swangers, romance and $$$$$. But he really made it big when he signed to Universal and dropped his 2005 major label debut, The Sound of Revenge. In it Cham showed off his melodic hooks and crisp, agile rapping style, and also his taste for ambition, bringing in violins and other live instruments to fill out the album’s bombastic production.

And then of course there’s “Ridin’,” the album’s hit single, which bagged Cham a Grammy, broke ringtone-sales records and blew up across the globe with its anthemic message against police harassment. The song feels as resonant as ever amidst all of the police brutality and their unjust killings in the news today, and hammering the unjustness of it all home is the fact that Cham was never riding dirty in the first place—he doesn’t even drink or smoke.

“That song wasn’t even about me, honestly. I put myself in the shoes of other people. I was thinking about all the things that people have said, and why hasn’t nobody said this?” he says. “Even if you’re doing nothing, you could be a college student, whatever, and the police officer’s just looking like they think you’re doing something wrong. And it’s like, ‘Where’s the theme song for this?’”

He’s been quieter on the musical front in more recent years. He cut his ties with Universal in 2011, sick of being kept in the dark about important decisions related to his music. Since then his output has been limited to lower-profile EPs and mixtapes, and he seems to be in no rush to drop his long-awaited third album, Poison. That doesn’t mean he’s been slacking, though. He wants to make a music video for each of the album’s songs, and in 2011 he even flew to Baghdad to film one, collecting footage of gold toilets and man-made lakes in Camp Victory, the Saddam-era palace-turned-U.S. military base that has since been turned over to the Iraqi government.

“I got to drive a tank,” he says. He isn’t wearing his glittery grill of years past and shows off his pearly whites when he flashes a grin. “It was super intense.”

These days makes music mostly for himself and to keep his rhymes sharp, as he focuses more of his time to studying tech and venture capital. His interest began in the late-’00s when he started going to tech conferences, and after meeting a partner at Upfront Ventures in 2009, he moved into doing advising for start-ups and making investments. So far it seems to have done him well. Last year, one of the companies he gave money to, the online video network Maker Studios, was acquired by Disney for $500 million—with a promise of another $450 million if the company makes financial advances. He declined to say how much of a cut he made, but he says he expects to make way more money doing this than he did as a rapper.

At Upfront Ventures, he’s been paying close attention to how the partners deliberate over pitches and decide whom to invest in. There’s no set deadline for how long his residency will last, but they’re usually about six months, and by the end he hopes to have developed a winning pitch and get the financing to launch a start-up of his own.

“I don’t want to be the guy that’s sitting here, calling somebody and telling them their dream,” he says, explaining that he wants to do more than just advising and investing. “I want to be in the seat of the founder.”

He doesn’t have a solid plan yet, and there’s no guarantee that whatever he does come up will equal big success. A week after our interview, Jay Z’s own startup, the “artist owned” Tidal service, saw a devastating drop in popularity, falling off the top-700 iPhone app download charts.

But Cham is optimistic. In addition to sitting in on pitch meetings, he’s been having meetings of his own, telling friends about venture capital and entrepreneurship. He wants to spread the word that artists no longer have to bend the knee to major labels. With the right investments and ideas, they can claim ownership for themselves.

“When I was in Iraq, I was like, ‘OK, rap got me here.’ I’ll always keep that in my mind and realize that rap is what got me into this venture capital firm. Rap got me out of the hood. Rap got me out of Houston and helped me to see the world,” Chamillionaire says, sitting in the Upfront Ventures pitch room. “But now that I’ve seen the world and I see so much, I’m just on this mission to let everybody else know—especially my peers in the music industry—about what’s happening over here.”