How Chamillionaire Became a Better Entrepreneur than Rapper

Michael Beausoleil

The middle of the 00’s saw many rappers rise to fame then fall off the map. Sounds changed, ringtones became uncool, and new talent emerged. The music industry changes rapidly and many careers die faster than they started. For some people, the end of a music career might be the start of better endeavors.

Around 2004 the rap scene saw an increase in Texas-based rappers gain popularity. No one peaked higher than Chamillionaire, hitting the top of the Billboard Hot 100 for two weeks during the summer of 2006 with his song Ridin’. Falling from the top turned out to be a blessing in disguise because he’s become quite the successful investor.

Chamillionaire, whose real name is Hakeem Seriki, has taken some risks that paid off. He found ways to give back through his success, and has put his earnings to good use. Seriki’s music success has really pigeonholed him as a one hit wonder, but he’s much more than that. Now more than ever, we should be recognizing his accomplishments and they ways he is empowering future entrepreneurs.

The Decline of Chamillionaire the Rapper

If you remember the name “Chamillionaire,” it’s most likely thanks to Ridin’. If you don’t remember that song, you might be familiar with Weird Al’s pardoy White and Nerdy. For a brief moment in time Ridin’ was so popular that Weird Al could score the highest charting song of his career thanks to his parody.

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(Photo via Ridin’ music video & Universal Records)

Ridin’ was a catchy song, but also focused on the topic of racial profiling. This is still a conversation we’re addressing, and Chamillionaire was discussing it fourteen years ago. After this song, he struggled to find chart success again. His follow up album failed to reach the same level of success as The Sound of Revenge (the album containing Ridin’). The album after that never got released, and by 2009 the name Chamillionaire was old news.

As a solo artist, Chamillionaire would only ever release two proper albums. He would release a few more EPs and mixtapes, but as his success in music dwindled he would fade from the public eye. By the time he hit 30, he was facing retirement from the rap scene. He could continue with independent endeavors, but landing another major success seemed unlikely.

The Rise of Chamillionaire the Investor

This fast decline is quite typical for an artist who quickly rises to the top. This is also where Chamillionaire’s story becomes unique. Music began to become less of a priority, and business became a focus.

To some degree, this is not uncommon. Many rappers start their own record labels and hope to become the next media mogul like P. Diddy. Some even venture outside of rap with such examples being Beats by Dre or 50 Cent’s partnership with Vitamin Water. Others try to find success in other genres, like Akon who is credited with giving Lady Gaga her first major deal. While all of these ventures are impressive, they’re also enhanced by star power and celebrity endorsements.

Chamillionaire’s interest lied in the tech scene, and he first dipped his toes into this space in 2009. Venture capitalist Mark Suster recognized the rapper for his ability to engage an audience while at a tech convention. He wasn’t just generating excitement, he was discussing how he rose to the top of the iTunes charts thanks to his focus on digital media.

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(Photo Chamillionaire via Deccan Chronicle)

Audience engagement wasn’t the only reason Chamillionaire appeared on the tech scene; he was there to learn to invest. He made some notable investments early in his career, but not without shopping around. Early in his career, he invested in Maker’s Studio, which would later be sold to Disney for a reported $675 million. While it’s unknown how much Chamillionaire made in this investment, he invested early and made a significant profit upon his exit.

By 2015, Chamillionaire joined Upfront Ventures in Santa Monica as the Entrepreneur-In-Residence. In this role he invests early in rising tech companies, hoping to accelerate the growth and identify the next big thing. It’s hard to deny his eye for future successes. His portfolio includes early investments in: home security system Ring (acquired by Amazon), self-driving car technology Cruise (acquired by GM), and ride-sharing app Lyft which went public in 2018.

For a one hit wonder, it’s safe to say Chamillionaire is doing better than a lot of other rappers.

Investing in the Future

It’s true that people hate to see you become successful, because no one saw Chamillionaire while he was acquiring his newfound success. In 2017 the internet went abuzz when he was spotted court side at the NBA finals. Despite some nice seats at an NBA game, Chamillionaire hasn’t really been bragging about his money. Right now, he’s investing in his future and the futures of others.

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In 2018, Chamillionaire introduced the world to his own app named Convoz. The goal is to encourage collaborative video conversations around current topics. If Twitter and TikTok had a baby, it might look something like Convoz. One user posts a message, another user can reply, and anyone else will see the back-and-fourth like it’s a realtime conversation.

Future plans include helping new tech ideas blossom, particularly for women and people of color. In 2019, Chamillionaire held a content to invest $25,000 in a start up because so few start ups had a female founder and so few people of color had their start ups venture-backed. He later ran a second competitor, this time investing $100,000 into the winner. After applying through Convoz, Pierre Laguerre’s company Fleeting was selected as the winner. Laguerre is a Haitian-born college dropout who recognized the shortage of qualified truck drivers in the US. As our shipping needs grew, he wants to bridge the gap with by connecting truck drivers to on demand jobs.

Is Fleeting the next big start up? Possibly. It’s hard to deny Chamillionaire’s eye for success. While he still dabbles in rapping occasionally, his biggest success can be found in the investing world. He seems to have built a path for longterm growth rather than being dependent upon the trends associated with the music scene. At this point, he could probably retire if he wanted. I don’t see that happening, however. He wants to serve communities who are underrepresented by investors and build his reputation as a founder. He’s truly found success in a new industry, and his achievements are worth celebrating.

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