Most who make a name for themselves in the world of rap don’t plan on spitting bars forever. Instead, many of the best lyricists hustle hard to stack cash and then invest it accordingly so they’re set for life. Thanks to this approach, Chamillionaire’s net worth continues to grow long after he stopped rapping full-time. The Houston-bred entertainer came up in the early 2000s and is best known for his The Mixtape Messiah series (the original of which is the longest and most bought mixtape in Texas history). Early on, Chamillionaire started making smart financial decisions that eventually landed him the role of entrepreneur in residence at venture capital firm Upfront Ventures. Read on to learn more about his journey!

Chamillionaire’s Confidence Helped Get Him Started In The Rap Game

Strong networking skills helped Chamillionaire get his foot in the door of hip-hop alongside his friend Paul Wall. The ambitious duo connected with Michael “5000” Watts, owner of Swishahouse, and offered to promote his company in exchange for a chance to freestyle on his radio show intro. Watts agreed and eventually put their raps on his mixtapes, getting his new friends started on the road to Houston rap royalty. Wall and Cham collaborated on the Get Ya Mind Correct LP in 2002, selling over 150K copies and earning a nomination from The Source Magazine for independent album of the year.

He might not have known it then, but Chamillionaire’s life changed forever in 2004 after sharing his 61-track effort The Mixtape Messiah. Around the same time, the 44-year-old founded his Chamilitary Entertainment label, which has over 20 tape and album releases between Cham, Lil Ken, Troy Henry, Yung Ro, 50/50 Twin and the owner’s younger brother, Rasaq Seriki.

The “Ridin'” hitmaker gave us his debut solo LP, The Sound of Revenge, in 2005, debuting at No. 10 on the Billboard 200. It’s now certified Platinum by the RIAA and even earned Chamillionaire a Grammy for Best Performance by a Duo or Group. His sophomore project arrived in 2007 with features from UGK, Lil Wayne, Devin the Dude and Lloyd; this would be the last studio album to come from the Texas legend, although he went on to share mixtapes and his Ammunition EP into the early 2010s.

For Over Two Decades, He’s Been Making Sound Investment Decisions

Part of the reason the “N Luv Wit My Money” artist was able to step back from the spotlight are early investments he made. In 2003 he started out by backing Houston-based auto dealer Fly Rydes, which specialized in customizing cars. Less than a decade later, Chamillionaire reportedly made a multi-million profit after investing $1.5M in Maker Studios, an online video talent network. When they were acquired by Disney for $500M, the Southern superstar’s cut was an estimated $20M.