I found that my problem was unclear instruction about the timing between jumping and popping. One day when I was watching a slowmo ollie video though, I noticed that the skateboarder already was beginning to jump (at least his body was already going in an upward motion) before snapping the board off the ground. That was a critical change I needed to make in order to get it working. I had been trying to pop the board while all my weight was still pushing down on it (kind of an obvious mistake, but I somehow overlooked this). Hope this helps somebody.
So you want to know how to ollie? Be warned, it’s not for the faint of heart, and a lot of people have tried and failed and tried some more and still failed and then eventually thrown their boards into a wall out of frustration (I have no idea who those people are). It’s by no means an easy skateboard trick, but if you want to know how to ollie, start with these simple tips:
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An Ollie is basically an upward/forward jumping trick. The name “ollie” comes from the nickname of Alan Gelfand who created the ollie in 1976. The ollie was then modified for flat-ground use by Rodney Mullen in 1982, and it is this flat-ground version of the ollie which is most commonly referred to as the ‘ollie’ today. The ollie is arguably the most important trick in skateboarding because it is the foundation of the majority of skateboard tricks which require lift. When you want to do a trick like the kickflip, when you want to get onto something like a ledge, or down something like a set of stairs, or try handrails, the ability to ollie is a necessity. Therefore the ability to ollie high and with good control is critical to your total skateboarding skill-set.