Chamillionaire is a Houston legend who made the transition from rapper to entrepreneur after achieving major success during the mid-2000s. • Chamillionaire got his start as a rapper on the KBXX-FM radio show of Michael “5000” Watts, a popular mixtape DJ from Houston who owned the label Swishahouse. • He signed to Universal Records in 2005 and released the platinum-selling album The Sound of Revenge. The single “Ridin’” hit No. 1 on the Billboard Hot 100 and won a Grammy for Best Rap Performance By a Duo or Group. • The rapper collaborated with singer Ciara on the single “Get Up”, which was featured in the 2006 film Step Up, starring Channing Tatum, Jenna Dewan and Mario. • After parting ways with Universal due to unresolved legal issues surrounding his unreleased third studio album, Chamillionaire dropped the 2013 EPs Elevate and Reignfall on his own label. • Since then, Chamillionaire’s primary focus has been tech investing. He was an early backer of companies such as Lyft, and he held the title entrepreneur-in-residence at the venture capital firm Upfront Ventures.