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.

When learning it, you will, slip and fall. Feel like an idiot doing something over and over again and not getting it, feel fear bcos you don’t know what's going to happen to you once you pop the tail, jump and slide your foot and then you land. Will you land on your board, will you be on the pavement? Will you slip out, will u kick the board away, will you land primo? No one knows but you gotta try it out and find it out yourself. Whatever it is, don't give up cos it's the strength to persevere, be crazy persistent to achieve and most of all being patient in learning and progressing that let's you earn the skateboarder title for your ownself.
The rider begins the ollie by crouching and jumping directly upward. As the rider begins to leap, instead of lifting the feet from the board, he/she "pops" the tail by striking it against the ground, which raises the board nose-first. Maintaining contact with the board, the rider lifts the front leg and bends the front ankle so that the outer or top side of the shoe slides towards the nose of the board. The friction between the shoe and the board's grip tape helps to guide and pull the board upward, while the rear foot only maintains slight contact with board to help guide it. When nearing the peak of the jump, the rider lifts the rear leg and pushes the front foot forward, which levels the board and keeps it in contact with the back foot.
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. 
Decks come in a variety of shapes and sizes. You can choose a mini-board, a cruiser, a drop-through or a standard deck for your favorite set of wheels and hardware. Widths range too from a few inches with a 22-inch board to the wide size of a true cruiser. Some decks are flat as possible while others are significantly concave for optimized turning. You can buy a deck with artwork and grip tape already attached for a quick install or you can get a bare-bones wooden deck to truly customize.

The longboard, a common variant of the skateboard, is used for higher speed and rough surface boarding, and they are much more expensive. "Old school" boards (those made in the 1970s–80s or modern boards that mimic their shape) are generally wider and often have only one kicktail. Variants of the 1970s often have little or no concavity, whereas 1980s models have deeper concavities and steeper kicktails.[7]
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.
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