If you’ve ever watched a skateboarder roll down the street and then all of a sudden pop into the air on a skateboard, you’re probably wondering the same question a lot of people do: how on earth do they do that? It almost seems magical how they just seem to explode off the ground, and then just kind of float. Skateboarder, meet, the ollie. It’s not in the category of “easy skateboard tricks,” but if you learn how to ollie, you’re well on your way to fame and fortune as a professional skater.
Today, many riders use the “ollie-pop” on more than just the flat-level surfaces in between other tricks, it’s used heavily in the half-pipe and bowl ramps to allow the rider to go even higher in the air. Performing the “ollie-pop” while you’re at or near the top of the lip is a great way to get an extra couple feet, which might be all you need to get that extra turn in and nail the 720 (or 900, if you’re Tony Hawk).
When I was about 10, I broke my first skateboard by riding it into a ditch. A decade later, in college, I broke another skateboard within an hour of owning it (surely a record) in a short-lived attempt at doing an ollie. (Surprisingly, the store accepted a return on that board even though it was in two pieces.) Then I was gifted a really nice, high-quality skateboard. The first thing I did with it was ride it down a big hill, a valiant but ill-fated adventure which ended with me jumping off the skateboard, rolling down the grass, and arriving scraped up, deflated, and rather disoriented near the entrance to my college cafeteria. (In my defense, the wheels and ball-bearings on that skateboard had been pre-lubricated to minimize friction, and why would anyone do that, that's just crazy.)
As you jump into the air, your front foot needs to roll slightly inward, and with the outside of your foot, you want to guide the skateboard as it flies into the air. Some people describe this as dragging the side of your front foot up the skateboard – that’s more or less what is happening, but what you are doing is using your shoe and the grip tape on the board to pull the skateboard higher into the air with you, and guiding the skateboard to where you want it.
It is mainly because those items are guaranteed to help you familiarize yourself with the ins and outs of using them. They are a big help in making you feel comfortable when you push off with your feet while also balancing on top of the board when riding. It is not good to go for a very technical product, so it’s best to choose the mentioned types first.