I found that my problem was unclear instruction about the timing between jumping and popping. One day when I was watching a slowmo ollie video though, I noticed that the skateboarder already was beginning to jump (at least his body was already going in an upward motion) before snapping the board off the ground. That was a critical change I needed to make in order to get it working. I had been trying to pop the board while all my weight was still pushing down on it (kind of an obvious mistake, but I somehow overlooked this). Hope this helps somebody.
Now, I might not be able to skate to save my life, but I can do a little physics. So here's a thought - maybe I can use physics to learn how to do an ollie. Here's the plan. I'm going to open up the above video of skateboarder Adam Shomsky doing an ollie, filmed in glorious 1000 frames-per-second slow motion, and analyze it in the open source physics video analysis tool Tracker.
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