The official record for the highest flat-ground ollie is 45′ (114.3cm) by Aldrin Garcia during the “Maloof High Ollie Challenge,” held on the 15th of February, 2011. You can watch the movie here. However, a groundbreaking moment in the lore of the ollie will always belong to Danny Wainwright’s ex record of 44.5′ (113.03cm, ELEMENT-HIGHEST OLLIE CONTEST Feb.6th,2000.) Reese Forbes, a competitor of Danny’s in this contest, was also well-known as a master of the ollie.
The good news is that majority of skate shoes today come with high-quality flat soles that are capable of providing the maximum surface area designed to let you come in contact to the board, thereby promoting better control. Look for a really durable shoe, which you can wear comfortably to guarantee a safe and enjoyable experience when you are skateboarding.
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.

Don’t get your hopes shot if it takes you a while to get this down.  Once you know how to ollie, beginner skateboarders you can do any trick in the book with just a little bit of practice.  Once you get this trick down while your stationary, go practice while moving around a little bit, try to hop off a couple of curbs.   You’ll be skateboarding like a pro in no time.  Just keep at it.
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.
Smile and wave – Feel free to look around at all the other people at the skatepark that stood by and marveled at your new-found accomplishments (all one of them). I’m sure by this point you’ll be picking up roses that are being thrown at your feet, and taking a well-deserved bow as they begin to chant your name. Take it all in, thank the crowd for their undying affection, and then go get a snow-cone. You deserve it, champ.
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