So after spending some time squatting in front of my tv like a horses pa toot with no luck, I realized the issue. It seems you have to have the controller in your hands to do this achievement, and be in the menu of the app, not watching a video (thanks ch1cag0steve).
So Start the Machinama App, hold the controller in your hands, squat (and stand back up), and pop, the achievement should unlock. For good measure I was also going through the menus as I 'dipped'...but can't confirm if that is an achievement requirement. If you are having issues, just keep trying various methods of squats, as it seems the achievement is finicky on when the achievement pops.