Chamillionaire at Upfront Ventures. Photo by the author.Itâs 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. Weâre 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. Chamâs sitting in a swivel chair, resting his elbows on a frosted-glass table, angling forward as he explains to me the difference of being ârichâ vs. being âwealthy.ââI walked around the music industry for a bunch of years, right? I saw a lot of rich people. I didnât see wealthy,â he tells me. âI 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? Iâm in Silicon Valley, Iâm in L.A., Iâm in Santa Monica, and Iâm seeing billionaires all over the place. And theyâre young. Thatâs not in the music industry.âRight now, the 35-year-old born Hakeem Seriki is rich. But heâs aiming to get wealthy. Thatâs what brought him to Upfront Ventures. Since March heâs been heading here every week to serve as the firmâs new âEntrepreneur in Residence.â In the world of venture capitalism, an âEIRâ is a relatively loose, informal and temporary positionâbasically 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 Chamâs case, he says he doesnât have specific office hours; heâs 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 weâre sitting in to pitch their ideas to Upfrontâs partnersâwith the hopes of walking away with a term sheet promising anywhere from $1 to $10 million in seed money.Continued below.The experience has been quite an educational one for the 35-year-old big name of the mid-â00s Houston rap explosion, whoâs otherwise known as King Koopa. Though he declines to name whoâs been coming in, Cham says visitors include scientists, Ivy League graduates, people who have brilliant ideas and âpeople who are just winging it.â Essentially itâs a grab bag of people touting projects Upfront might be interested in getting a piece ofâsomething that could prove to be a total flop, or could just as well end up as the next Uber or Snapchat.âThere are people that are doing things that I wouldâve never even thought possible,â says Cham, whoâs giving his first interview about the EIR since it was announced in February. âTo 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 couldnât 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.âSo, uh, why exactly is Chamillionaire chilling with VCs these days? The answer is simpleâmoney. Also, power, influence and equity. Heâs dunzo with the traditional workings of the music industry. In recent years heâs 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 itâs paved in tech dollars.âYour Facebook page youâre posting all onâhow much money are they making off your page? Do you know?â he says. Heâs looking understated but fresh in a black hoodie, chunky diamond earrings and long gold chain. âMost people donât know, or donât care to know. Iâm one of the people that kinda wants to know.âCham has always been a business-minded fellow, but heâs 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 Wallâs 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 albumâs bombastic production.And then of course thereâs âRidinâ,â the albumâs 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 placeâhe doesnât even drink or smoke.âThat song wasnât 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 hasnât nobody said this?â he says. âEven if youâre doing nothing, you could be a college student, whatever, and the police officerâs just looking like they think youâre doing something wrong. And itâs like, âWhereâs the theme song for this?ââHeâs 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 doesnât mean heâs been slacking, though. He wants to make a music video for each of the albumâs 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.âI got to drive a tank,â he says. He isnât wearing his glittery grill of years past and shows off his pearly whites when he flashes a grin. âIt was super intense.âThese 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-â00s 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 millionâwith a promise of another $450 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, heâs been paying close attention to how the partners deliberate over pitches and decide whom to invest in. Thereâs no set deadline for how long his residency will last, but theyâre usually about 6 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.âI donât want to be the guy thatâs sitting here, calling somebody and telling them their dream,â he says, explaining that he wants to do more than just advising and investing. âI want to be in the seat of the founder.âHe doesnât have a solid plan yet, and thereâs no guarantee that whatever he does come up will equal big success. A week after our interview, Jay Zâs own startup, the âartist ownedâ 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, heâs 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.âWhen I was in Iraq, I was like, âOK, rap got me here.â Iâll 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,â Chamillionaire says, sitting in the Upfront Ventures pitch room. âBut now that Iâve seen the world and I see so much, Iâm just on this mission to let everybody else knowâespecially my peers in the music industryâabout whatâs happening over here.âPeter Holslin also wants to be a Chabillionaire. Follow him on Twitter.
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