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.
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.
The board also boasts of its reasonably small size and lightweight nature, making it easy to control and ride. In addition, carrying it wherever you want to go is also much easier because of its lightness. It is flexible enough that it can accommodate the needs of different kinds of users, including cruisers, travelers, beginners, expert riders, and kids.
In general an axle width should be chosen that is close to the width of the deck it will be used with. For example, a 7.75" wide deck will usually be fitted with trucks that have axles between 7.5" wide and 8.0" wide. (Standard truck axle nut size is 5/16"-24tpi UNF, and the thinner "jam" style with an optional nylon lock.) Trucks that are too wide can make doing tricks difficult and can cause the wheels to get in the way when the skateboard is being ridden. Trucks that are too small can be hard to maintain stability and can cause wheel bite to occur when turning.
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.
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.