An Ollie is the most basic but fundamental trick in skateboarding. Knowing how to ollie is the basis of learning flip tricks, grinds, and simply helps move around town getting up and down curbs.
There are open, never ending debates on the best way to start learning and getting comfortable with ollies but first and foremost you need to be comfortable with your skateboard. get a good, quality deck. It does not have to be expensive and it does not need to have expensive parts. Buying an already built complete from your local skate shop is great. If you can not find a built complete, getting an inexpensive deck such as the Schlaudie Lil' Logo with quality trucks, wheels and bearings works perfect and will last a new rider an extremely long time. Steer clear of Wal-Mart and target "skateboards". They are not the same as quality decks from your local skateshop. The wood is cheap, has no pop, snaps easily and the bearings and wheels do not move as freely as they should. Because of their severely low quality, they can potentially cause an extremely long learning curve and slow down your progression before it even has a chance to start. Go with quality. It is more expensive but ALWAYS better.
Now that you have a quality board, there are multiple ways to help learn the basics of an ollie. But, getting comfortable with the board is primary. So, I recommend that you get on the board and skate. Roll around. Go to the skatepark and learn to balance on the deck. Learn to turn, feel out the trucks and set them for your level of comfort. Ride the board with no thought process of tricks until you are comfortable enough on your deck pushing, turning and riding that it is done with ease.
After the comfort and balance is built, now we can work on learning tricks. I want to emphasize that your ability and speed to learn how to ollie is all on YOU. DO NOT worry about your friends, the guy you spoke to on Instagram or anyone in any videos. Do not let anyone make you feel bad about learning and do not get upset with how long it may take to start landing your first ollie. Both in my time skating growing up and meeting kids through the brand, I have seen beginners vary in learning. Some pick up ollies and move to other tricks quickly others take several months. Again, do not worry about how long it takes you and do not let anyone make you feel bad for taking longer. Go out, and have fun in the learning experience. THAT is what skating is about.
Once you are comfortable with your board, you want to get comfortable with the movement and motion of doing an ollie. An ollie is the basic pop or "jump" with a skateboard. It is the action of being able to pop your skateboard's tail while dragging your front foot upward in order to get all four wheels off the ground to get up and over obstacles.
Foot Placement:
You want to start with proper foot placement. Your back foot should be placed so as to easily have a downward motion on the tail. Your foot should be mostly (or fully) on the tail but at the back edge so as to be able to slam the tip of the tail on the ground. Your front foot should be just behind the bolts which hold your front trucks. The ball of your front foot should be close to center on the deck.
Popping:
You want to make sure you have a proper pop. There is something about the sound of a good pop that is beautiful to the ears. The slamming of wood on concrete is music and something skaters love. In order to get used to popping, you have to practice. You can start with standing with only one foot on the deck. Stand with your front foot on the ground and your back foot on the tail. Push down on the tail of the skateboard with force and as soon as the tail touches the ground, immediately lift your foot off the board. You should see the front of your skateboard go upward and when you let go of the deck, your tail should come up off the ground. This is the basic motion of popping. Practice this in order to get used to the action of popping.
Foot drag:
After you have gotten used to popping the tail, your next focus should be foot drag. This is the motion of moving your front foot upward toward the nose. It is done immediately following the pop of the tail. By dragging your front foot up, it assists to lift the tail of your board and even it out over the ground. It also will help later on in gaining more height on your pop.
Stand on your board with the proper foot placement as stated before. Then, push the tail of your skateboard to the ground and stand on the board with your tail on the ground and the nose pointing slightly upward. With your front foot, drag the side of your foot up toward the nose. You will want to continue doing this motion many times in order to build muscle memory with it. Eventually you will start to see lines in your grip tape going up toward the center of your nose as your shoe drags.
Putting it all in motion:
Now that you have learned the proper foot position, learned how to pop the tail and learned how to drag your front foot, you want to put it all in motion. There are plenty of ways to help get comfortable with all of the so-called "moving parts". You can place your rear wheels into a crack in the sidewalk to help keep your board steady as you learn to pop; you can practice in short cut grass, or you can even buy skate helpers which go over your wheels to keep you from rolling. Which ever way you do it, do what you feel most comfortable with.
Stand on the board and pop your tail down. As soon as it touches the ground, jump with your back foot and drag your front foot upward toward the nose as you did before. This will allow the board to pop upward while using your front foot to guide and level out the skateboard.
As soon as you start to get the motion, I recommend that you move to rolling ollies. Do this as early as possible. This will make it slightly harder, but the motion of movement will get you ollieing faster over obstacles sooner. and get your to feel more comfortable with ollies. Your ollies will not be high at first and possibly only a few inches off the ground but in order to help make things more fun and give you something to work toward, find a crack in the ground and ollie over it. It will give you something to work toward and something to be proud about when you finally land it!
Something to watch for:
Many find when they are learning to ollie that their board often goes behind them. This is caused by uneven shoulders. Keep a conscious understanding of your shoulders and where they are pointed. The jumping motion will make your shoulders want to turn so make sure you keep them parallel with the board. Throughout skating, you will find that your shoulders guide a lot of the direction of the skateboard.