Sheckler was born in San Clemente, California. When he was just 18 months old, Sheckler found his dad's old-school skateboard. Sheckler taught himself to push it around using one knee, and eventually stood up on the skateboard. From age 6 on, he has spent up to 22 hours a week practicing tricks in his backyard skate park, which includes a half pipe, table tops and several grind rails. He developed his own trick called the Sheck-lair - an indy kickflip flyout.

Sheckler's career took shape during the summer of 1995, when his dad built a new quarter pipe in the family's skatepark. A few years later, he joined the CASL (California Amateur Skateboarding League), entered one of their contests and won.
Sheckler turned professional in 2003 after winning in the X Games, Gravity Games, Vans Triple Crown and Slam City Jam.

In 2004, he was named the World Cup of Skateboarding’s National Street Champion. The next year, he took the title again, along with the AST Dew Tour Athlete of the Year. In 2006, 16-year-old Sheckler won the Global Assault in Australia and finished fifth at the Tampa Pro in Florida.Sheckler is currently on tour making a few appearance nationwide for Jourey's Backyard Barbecue (2009).