Chamillionaire Ditched Rap to Do...What?

Andy Sheppard/Redferns

"I bet Slim Thug sounds like a big dummy." That was a friend of a friend’s the other day. We were having drinks and I had just met this guy. I’m not sure how much of that line could be attributed to alcohol, but I replied that Slim Thug was actually a smart businessman who seems to be doing fine for himself.

He asked if I'd met Chamillionaire. I replied that I'd met him twice and interviewed him for a story once.

He was silent. I wasn’t sure if he was thinking of Chamillionaire, who is also known as King Koopa, as a dummy, but I offered up a preemptive response anyway:

"Chamillionaire is a smart guy, too. He built his career from the ground up, sold his music out of the trunk of his car. He even made Forbes list one year."

There’s this stupid myth that the ability to string rhymes together is also synonymous with the inability to conjure up profitable business moves. This myth persists, despite the resounding success of people like Jay Z, Master P and 50 Cent. And Chamillionaire.

Chamillionaire exploded onto the national scene in the mid-00s after turning a $4000 song to a platinum-selling, chart-topping, Grammy-winning hit. That song is "Ridin'," which you've probably heard. He's also a savvy entrepreneur who invests in early stage startups and advises for tech companies.

Chamillionaire hasn’t released a proper album in eight years, but he’s been plenty busy.

What has he been up to lately? When are we going to hear new music? Are we going to hear new music?

Noisey’s Peter Holslin caught up with the Mixtape Messiah recently. Turns out Chamillionaire has taken up residence in sunny Santa Monica, where’s he studying the investment game at Upfront Ventures.

“I walked around the music industry for a bunch of years, right?

I saw a lot of rich people. I didn’t see wealthy,” Cham tells Noisey. “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.”

Cham is the EIR (Entrepreneur in Residence) at Upfront Ventures. It’s a loosely defined role that basically amounts to an opportunity for Cham and his business partner Nsilo Reddick to learn what works and what doesn’t in the VC realm.

Cham’s adventures in LA could be traced back to a chance meeting with venture capitalist Mark Suster in 2009.

"Five-and-a-half years ago I first met Chamillionaire at a tech conference in LA," says Suster. “I saw him on stage at the event talking about how he used social media to engage audiences. This was 2009 and his understanding of audience engagement was far beyond anything I was hearing from most people at that time."

After hanging out with Cham and discussing a few business ideas the rapper was mulling, Suster urged the Houston rapper to move to the west coast for a chance to immerse himself in the investment process.

"I told him it’s one thing to fly 2x a month from Houston to LA, SF or NY to meet entrepreneurs and a whole other level to immerse himself in the scene by meeting entrepreneurs every day as I do. When you see pitch after pitch – what works and what doesn’t – you start to get a sense of patterns of business model approaches, go-to-market strategies and the like," Suster writes on Both Sides of the Table.

"So we discussed his moving to LA for a while and working in our offices and developing his ideas and we decided to formalize it.”

At Upfront, Cham sits in on pitches. He gets to watch and learn up close. "I don’t want to be the guy that’s sitting here, calling somebody and telling them their dream," he tells Noisey. As Cham explained, he doesn't want to settle for advising or investing, he wants to be "in the seat of the founder.”

Chamillionaire has several mixtapes and two full-length albums, The Sound of Revenge and Ultimate Victory, to his name. He heads his own Chamillitary Records.

Cham’s residency at Upfront Ventures is expected to last six months. He hopes to have developed a pitch by the end of the project.