How do you get confidence on a skateboard?

im a very good skateboarder, but i have a problem. since i skate so much i go threw decks and shoes in a week. I want to get sponsored and to achieve that goal i want to learn handrails. I just don't have enough confidence to ollie up on to the rail. im not sure i could ollie up on to the rail. so i was wondering if you could give me some advice about confidence.