This can be tricky to figure out, so just take your time and relax. The first few times you try and ollie, it helps to not worry about this part. You will end up doing a sort of half-ollie, popping just a little in the air. Or, you might fall! But, don't worry, this is all part of learning. If you want though, you can certainly start with rolling your ankle when you try and ollie - whatever works for you! Eventually, you will need to roll and drag, and you'll figure it out. Just take your time!
Invented in the late 1970s by Alan "Ollie" Gelfand, the ollie has become a skateboarding fundamental, the basis for many other more complicated tricks. In its simplest form, the ollie is a jumping technique that allows skaters to hop over obstacles and onto curbs, etc. What's so amazing about the ollie is the way the skateboard seems to stick to the skater's feet in midair. Seeing pictures of skaters performing soaring 4-foot ollies, many people assume that the board is somehow attached to the skater's feet. It's not. What's even more amazing about the ollie is that to get the skateboard to jump up, the skater pushes down on the board! The secret to this paradoxical maneuver is rotation around multiple axes. Let's take a closer look.
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The Wasatch Imports Good Skateboards is the ultimate compact and complete street board that is ready-to-go. It is great for exercise and fun. It is very portable and perfect for all skill levels. It has a variety of awesome vintage color combinations that you can choose from. It is made of topline construction, with a high-density plastic deck, 59mm super smooth wheels, ABEC7 bearings, and solid aluminum trucks. It measures 22″ long and 6″ wide and weighs 4 pounds. It has a  full manufacturer’s lifetime warranty on all parts, pieces, and materials. It has a weight limit of 200 pounds which can ensure that bigger skaters can join the fun.
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The Powell Golden Dragon 2 Skateboard is an affordable and complete skateboard for the beginners and also for the advanced skaters.  It has high-rebound, hand-cast polyurethane wheels to give you a great roll and grip.  It measures 7.5 inches wide with a colorful screen-printed bottom.  It is made in China and has an average rating of 4.2 on Amazon.
The DAPANLA deck is 7.5-by-31-inches in size, on the smaller side of good quality, real skateboard decks, which makes it ideal for smaller and shorter people. Unlike many decks on the market today, the DAPANLA deck comes with non-slip grip tape on the top. The underside of the deck is similarly decorated, with a range of DAPANLA designs including the fun cartoon avocado board that is sure to turn a few heads for its uniqueness. 
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It wouldn’t be until the early 1980’s however, that a man named Rodney Mullen fully developed the skateboard ollie and brought it into vogue. Competing in the Rusty Harris contest in Whittier, California in 1982, Rodney Mullen used a back and forth motion on his skateboard to strike the back end of the board on the ground and using the front end to level the board out in mid-air – all from a flat surface. The audience’s jaws collectively hit the ground.
So you want to know how to ollie? Be warned, it’s not for the faint of heart, and a lot of people have tried and failed and tried some more and still failed and then eventually thrown their boards into a wall out of frustration (I have no idea who those people are). It’s by no means an easy skateboard trick, but if you want to know how to ollie, start with these simple tips:
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