text: skateboarding help? ok i know how to ollie but icant seem to ollie while im riding... can anyone help? 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.