text: well before you can ollie while riding you have to get comfortable when doing an olie. so if you been doing an ollie for a day the keep doing the ollie over and over again for about a week. then start by going slow. then a little faster and a little faster. until you go the fastest you can on your skateboard. but dont worry about falling its okay if you do just get back up and keep trying i have been watching the pros do it for about 5 years.