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.

James Haden is one of the owners of the Skateboarder community, together with Nash Gibson – his co-owner. He works as a full-time copywriter for a private company and also a true adventurer. He is an avid reader, writer, traveler, and extreme sports junkie. During his free time, he researches interesting content for their blog and continuously writes for their audience.
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.)
In 1977, skate parks began cropping up all over the place, including Skateboard USA, where Gelfand began to spend most of his time. His buddy, Scott Goodman, is the one who gave Gelfand the nickname of “Ollie” and dubbed his aerial lipside the “ollie-pop.” Pictures of Gelfand during this time period clearly show him getting airborne and performing the trick associated with his name today.
Slam your back foot down on the tail of your skateboard as hard as you can. At that moment, you want to also jump into the air, off of your back foot. This part is key and takes practice. The trick is in getting your timing right. You want to slap the skateboard’s tail down, and as it hits the ground, jump off of that foot into the air. Make sure to pull that back foot high into the air. It's a quick, snapping motion.
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Smile and wave – Feel free to look around at all the other people at the skatepark that stood by and marveled at your new-found accomplishments (all one of them). I’m sure by this point you’ll be picking up roses that are being thrown at your feet, and taking a well-deserved bow as they begin to chant your name. Take it all in, thank the crowd for their undying affection, and then go get a snow-cone. You deserve it, champ.