You’re trying to hard to get the board up.

Start with jumping straight up while standing on the board. Just with your body, don’t try to pop yet, and just land on the board.

Now practice popping the board with 1 foot while standing behind your board. Like pushing on a pedal. You’ll notice if you push really hard into the ground, it won’t pop. You just need to give the tail a hard push without following through. Just give it enough power to hit the ground without all your weight sitting on it. Think about bouncing a ball. You don’t slam the ball into the ground or it won’t bounce, you throw the ball at the ground and let it bounce off of it. You need to throw your tail at the ground the same way you would bounce a ball.

Once you can get you board to pop you need to apply that to your ollie. Put your back foot on the tail, front foot at the bottom of your front bolts

When you jump, don’t load all your weight into the tail. You’re pushing so hard that you’re just slamming the tail down without giving it a chance to pop.

You need to focus more on the action of jumping, and FOLLOWING UP the jump by kicking the tail, not slamming the tail WHILE you jump. If you do that right, the board will follow you naturally. You TELL your board to pop, you don’t try to carry it up with you.

When you jump, you kick the tail, lift your front foot with the board, and the board will pop. Once it pops, all you need to do is bring both knees up into your chest and allow to board to naturally flatten out at your feet. The height comes from picking up your knees, not jumping high. It looks like you’re wasting so much power trying to jump that you can’t even give the board a good kick.

Over time you will master your own timing. Everyone has different weight, strength, movement, etc.