Raised in Oakland, California, Tajai first met fellow Souls of Mischief member A-Plus in elementary school and the duo began their nascent rap careers. Tajai and A-Plus combined forces with childhood friends Opio and Phesto in high school to form Souls of Mischief before releasing their debut album, 93 'til Infinity on Jive Records in 1993. He graduated from Stanford University in 1997 with a degree in anthropology. He graduated from UC Berkeley in 2014 with a master's degree in Architecture. Souls of Mischief is one half of the crew Hieroglyphics, along with Del the Funky Homosapien, Casual, Pep Love, Domino and DJ Touré. Tajai has contributed to all six Souls of Mischief albums, as well as all three Hieroglyphics studio albums. In 1999, Tajai and the Hieroglyphics' then-webmaster, StinkE, formed the conceptual group SupremeEx and the Entity, which released an enhanced CD, Projecto2501, and in 2005, released the album Nuntype. Tajai is also a member of Crudo, a project featuring Mike Patton and Dan the Automator, who made their live debut in 2008. Recently Tajai created Rap Noir, a hip hop duo with producer Unjust from Chosen Few. They released two albums in 2018: Rap Noir and Trap Noir. Currently he is working on two studio albums, one with super producer The Architect called BLKTEK and another with the legendary Breakbeat Lou.