Almost no one lands an ollie on their first try. Repetition is the most important part of learning how to ollie. Once you learn how to do an ollie, you can try doing them while rolling. Learning is one of the funnest parts of skateboarding. After you learn ollies, you can move onto 180s, Pop Shove-Its, and flips. Soon a whole world of tricks will open up.
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In 1977, skate parks began cropping up all over the place, including Skateboard USA, where Gelfand began to spend most of his time. His buddy, Scott Goodman, is the one who gave Gelfand the nickname of “Ollie” and dubbed his aerial lipside the “ollie-pop.” Pictures of Gelfand during this time period clearly show him getting airborne and performing the trick associated with his name today.