As with any winching trick, your first step to ollie a gap is to make sure the gap is safe and not totally sketchy. Make sure you have enough room to land (and remember you will cover some ground when you ollie at 20-plus miles per hour!) Make sure there is nothing that will tangle up your rope or any jagged rocks in the landing.
Before you attempt to ollie a winch gap, you want to have your ollies down in the flats behind the boat. Make sure you know how to get your legs up and stay over your board.
As you are approaching the gap, you may need to edge left or right, depending on the location of the winch. If you being pulled straight, you can flatten off, but if not you may need to pop off your edge. Keep your handle close to your hip, knees bent, and stay relaxed so that you can use your whole body when you ollie. Now just pop and stay over your board and spot your landing. Before you know it you’ll be at the bottom of the gap.
For your first time ollieing a gap, make sure you find something mellow. If you just keep it mellow, worry about getting your knees up popping a little ollie, the winch will make sure you cover the distance you need. BUT. You probably won’t have much luck landing like that. If you pop as hard as you can, the board will stay with you and your knees will be more bent for landing, meaning you won’t land so hard (and you’ll look a lot cooler.)
After you get comfortable with ollieing down a gap, add some style and then start throwing tricks!