Method #1

The ollie is possibly the greatest trick in all of skateboarding, because without it, almost everything else is impossible. All skaters should be eternally grateful that Alan "Ollie" Gelfand invented this trick. Send him a few dollars.

The ollie should be learned while standing still. Place the board in a patch of grass in the park, or even better, place it on the sidewalk so that the rear wheels are inside the sidewalk crack.

This prevents the board from moving back and forth too much, which can cause balance to be lost. This technique can be used to learn many tricks, including flip tricks, although it generally is not helpful in learning tricks that require body and/or board rotation.

Place the back foot on the tail and the front foot on the bolts.

Push the back foot down so that the tail hits the ground. At the same time, lift the front foot up. A split second later, lift the back foot off the ground.

The importance of the back foot is frequently underestimated. The back foot must "pump" down, then up, in order to successfully ollie. Many beginners fail to do this and the result is frustration. This is a split-second motion, so it should not to delayed.

In fact, this "pumping" motion of the back foot is essential in all flip tricks, not just the ollie. Being accustomed to this movement will help speed the learning process when attempting more difficult flip tricks.

Method #2

The first thing with an ollie is to be relaxed and smooth. Watch any pro skater ollie and they're smoother than silk sheets. When you're feeling relaxed and smooth stand on your board with one foot on the kick and one foot in the exact middle of the board. (Try this trick stationary first then add motion later). Then with your back leg jam down the kick. This should but all the wheels of the board into the air momentarily. As soon as you do this drag your front foot up the board. Using the front kick to "catch" your front foot is a great idea and will give you extra height. For a good part of the ollie only the front foot should be in contact with the board. When you come to the peak of your ollie shift your weight equally on both feet in preparation for the landing. Land, bend at the knees and ride away.

Extra

Ollieing Curbs
Try approaching the curb at an angle, such as 45 degrees or so. It is usually much easier this way than approaching from a perpendicular angle. Once the curb ollie is mastered from a 45 degree angle, the perpendicular version should be attempted.

The most difficult aspect of this trick is the timing. If the ollie is performed early or too late, the trick will fail. Here is a secret way to practise this timing:

Temporarily forget about the curb ollie and simply ride towards the curb and ride up it. Lift the front wheels up onto the curb and then a split second later, lift the back wheels onto the curb. After this timing is mastered, ollieing curbs may come more easily.

4. Increasing Ollie Height
This is a technique that may or may not work, depending on the individual, but it should be attempted because it has a chance of being quite helpful.

Most people, when preparing to do an ollie (or any other trick), crouch down slightly, then jump. To increase height, try this: crouch down super-low. Bend the knees so low that the back hand can actually touch the ground. Then do the trick.

Sometimes this technique may work well, but other times, it may not work at all. However, it should at least be attempted.

Also try this: instead of putting the front foot on the bolts, put it farther back, closer to the back foot. Instead of simply lifting up the front foot, lift it at a more vertical angle. Try to get the board totally vertical, rather than the usual 45 degree angle. This technique can also help increase ollie height.