A rushed take-off might be the problem here. Steps 2-4 of this trick tip could help you out. In order to make your feet “stick” to the board, you have to do the movement fluidly. But don’t stress yourself out! You should rather start with some preliminary exercises until you feel safe while ollieing. It is also important to pull your foot up to your board’s nose in a straight manner to prevent it from spinning.
It looks simple but yet complicated and vice versa. It takes most weeks to months to learn n some even years but a lifetime of effort to be consistent and be perfect at it and able to go higher, faster and further. It is not a feat you achieve once and it can be thrown out of the window if you want to continue to skate well. I've know skateboarders who just does ollies, boned ollies, ollie north and ollie souths, fakie ollies, switch ollies and nollies and nothing else but everytime he's popping them over 3ft height and up ledges, over gaps and down stair sets or over handrails. So no one's gonna argue on that even though he's not bustin some new fangled pressure flip late flip revert or something. He gets mad street creds for those huge ollies.
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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.


Before learning it, do have your riding basics down. Meaning you are very comfortable riding it around and doing kickturns and not be pushing mongo. Best to learn it whilst stationary with your wheels on a crack so that you don't move and slip out so much. I don't recommend doing it on grass or carpet cos when you pop the tail, it's gonna be absorbed by the floor and when you start doing it on pavement, your muscles will memorize a different way of doing it. So nope, no easy way out i guess.
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Before we show you how to ollie, let’s get familiar with the legends that brought this skateboard trick to the masses.  If it were a person, the history of ollie would start way back in 1974, when Alan Gelfand got his first skateboard from his father after his family moved to Hollywood, Florida from New York state. It didn’t take him too long to get the hang of it; he won the South Florida Skateboard championships two years later.
Low ollies: This can happen for a lot of reasons, but the biggest one is that you are not crouching low enough before your ollie, and not pulling your feet high enough after you jump. When you crouch down, try and touch the ground. When you jump, try to hit yourself in the chest with your knees. ​Both knees. Don’t worry about falling. That will happen sometimes – that’s just part of skateboarding! For more help, read the How Can I Make My Ollies Higher? FAQ
This board is an excellent option for beginners because of its simplicity and durability. The lightly concave design allows for simple turns but doesn’t require the rider to be an excellent navigator. You can start off riding this deck down the street and use it as you learn ollies, kickflips and how to drop in to a half pipe. It will withstand it all and look good doing it. 
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