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.
The ollie is a skateboarding trick where the rider and board leap into the air without the use of the rider's hands.[1] It is basically the combination of popping, sliding, and jumping on the skateboard all at the same time. Originated in vertical skateboarding, and later on flat ground, it is not intuitively obvious how the liftoff is achieved, making the movement visually striking.
It’s not just standard deck sizes that are available for creating or replacing your board. You can just as easily get a great longboard deck to work on in your basement or garage. One of the best and best reviewed options out there is the Loaded Boards Poke Longboard Skateboard Deck. This standard-design longboard deck has it all to help you make the ideal board. 

The board is shaped like a cup in the center, and has whale tails on both ends, designed to make tricks easier to do. The blue stain on the board looks like the picture. It has a semi flat finish with no lacquer top coat. The underside is plain which allows the owner to add stickers and graphics if they want but they look great just the way they are.


The longboard, a common variant of the skateboard, is used for higher speed and rough surface boarding, and they are much more expensive. "Old school" boards (those made in the 1970s–80s or modern boards that mimic their shape) are generally wider and often have only one kicktail. Variants of the 1970s often have little or no concavity, whereas 1980s models have deeper concavities and steeper kicktails.[7]

Punisher Skateboards Warphant measures 31 x 7.5 inch.  It has a 9-Ply Maple Black Board with Concave Deck and Double Kick Tail.  It comes with ABEC-3 Bearings, 5-inch V-style Heavy Duty Alloy Trucks, and Bases.  It uses 54 x 36 mm PU injection molded wheels and PE Riser Pad with PU Cushion and Punisher Logo.  It is perfect for learning and doing tricks.  It is best suited for riders who are 8 years old and above.  It has a 5 rating on Amazon.
The skateboard has a solid and stiff mini-deck, which is around 22 inches and constructed out of 100% plastic material. Such deck is very lightweight. It is only four pounds but you have an assurance that it can handle up to 198 lbs. of weight. You will also fall in love with the board as it comes in 23 graphics and colors, so picking a favorite is much easier.
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.
It comes with a plastic board deck, which is small in size, making it ideal for riders who need a really sturdy skateboard. It is more suitable for both experts and beginners who want to learn new tricks in skateboarding. The fact that it is stable and small makes it good for kids, too. It promotes ease in riding and controlling it in a crowded street. This complete skateboard is lightweight, too, allowing you to carry it almost everywhere.
The Bamboo Skateboards Galaxy Series Cosmic Cloud Skateboard Deck is an excellent option. This concave board is made exclusively of a bamboo hybrid, rather than pure maple. This means the deck is lighter, stronger, more flexible and can even absorb shock better. The non-carbonized, light-wood deck is made of 6-ply wood and is in its fourth generation of designs.
Skateboarding is a very individual activity. There is no right or wrong way to skate. Skateboarding still hasn't stopped evolving, and skaters are coming up with new tricks all the time. Skateboarding has gone through its ups and downs over the years. However, since 2000, due to attention in the media and products like skateboarding video games, children's skateboards and commercialization, skateboarding has been pulled into the mainstream. As more interest and money has been invested into skateboarding, more skate parks, better skateboards have become available. In addition, the continuing interest has motivated skateboarding companies have to keep innovating and inventing new things. In 2020 Skateboarding will appear for the first-time in the Olympics in Tokyo, Japan.[4]
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Sizing plays an important role in the performance of any deck. A large majority range in size from 7.75" to 8.5" in width. These will provide a great platform for shredding any obstacle and will excel in street and skatepark environments alike. For those who prefer a smaller board, decks are offered down to 7.5" in width- benefiting people with smaller feet or the technical skater. Conversely, those looking for a wider board will enjoy our selection ranging up to 8.9" wide. Larger decks will accommodate those with very large feet, as well as offer an amazing experience for cruising and shredding large ramps and transitions.
The Element Quadrant #14 board is 8-inches wide and 31.75-inches long, from nose to tail. This deck features a bare top that needs grip tape and a design on the bottom with four quadrants featuring the Element symbol in alternating red and black backgrounds. The wheelbase between the trucks is just over 14 inches while the nose is 7 inches and the tail is 6.325. 
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 KPC Series Pro Skateboard measures 8.0” x 32”. This is a common width most often associated with pro skateboarders. Wider and stronger than the rookies, this model is the perfect size for someone who is better at skating and looking for an upgrade from the rookie models. The pro features a modern concave which allows for not only comfort, but more pop making it easier to learn tricks.

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.
But, a quick warning! If you learn to ollie while standing still, you can develop some bad habits. Some skaters end up turning in the air a little, and not landing straight. You might not even notice until you try to ollie while rolling. So, if you practice while standing still, I highly recommend also practicing while rolling. Maybe only practice in one spot for a few days - maybe a week or two - and then give the rolling ollie a shot. That way, if you are developing bad habits, you can shake them off before they really mess you up.
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