[7] Growing up, Sheffey was inspired by the skating of Mark Gonzales, Jesse Martinez, and Natas Kaupas.
[2] In the late 1980s, Sheffey attended a skateboarding contest in Ocean City, Maryland.
[7] In his part in the 1991 Life Skateboards skate video A Soldier's Story, Sheffey notably fakie ollies over a school lunch table.
[8][2] After Life Skateboards, Sheffey joined the new company, Plan B, skating alongside a talented team of Danny Way, Rick Howard, Sal Barbier, Matt Hensley, and Rodney Mullen.
[2] In July 1994, Sheffey graced the cover of Transworld Skateboarding performing a kickflip at Fort Miley Military Reservation.