Before we start going for this achievement, download TinyTask to your computer (download link is
https://www.tinytask.net/). When you open TinyTask, set the hotkey for recording and playback to whatever suits your fancy (I did F12 for recording, F8 for playback) in Prefs and turn on Continuous Playback. Launch Endless Skater and go to the tutorial. Go up to the point where a hint will appear on the center of the screen and start recording. Exit out of the hint screen and keep pressing the ollie button (Up Arrow on Keyboard) until the game gives you another hint screen. Stop recording and playback. If done correctly, it should go like this: Enter, Up, Up, Up, Up, Up, Up, Up, Up, Enter (and so on). While you wait, go put on some TV or do something else. As long the game doesn't freeze or crash (which it did a few times on one of my computers), you'll get the achievement. Check back in every half of an hour to see if the achievement unlocked.