Jessee's first sponsor was Powell Peralta and later Vision Street Wear,[2] but made the move to a professional sponsorship deal with Santa Cruz Skateboards in December 1987.
He notably featured in the company's 1988 highlight video Streets on Fire, in which he played a fictional version of himself who is arrested and jailed for illegal skateboarding.
[4] After an extended period of absence from the skateboarding industry, Jessee was once again sponsored by Santa Cruz and he helped the company during its 40th-anniversary celebration in 2013.
[9] Jessee has additionally worked as a custom-car and motorcycle builder, and was briefly a member of Los Angeles–based lowrider car club Dukes.
[2] Jessee came under controversy in May 2018 when a thread on an online forum hosted by Slap magazine alleged his past usage of racial slurs, hate speech, and Nazi imagery.