You need to have one foot in front of the other. Most of your weight should stay on the front foot.

        Lift both toes off the ground so that only the wheels are touching. Make sure the back of the shoe isn't touching the ground - I'm quite sure that's the brake. (More on that later)
       
        It takes a few minutes to get your feet to stay in that position and your toes to stay above ground like that when you roll. Try (on a flat ground) someone pulling you along while you assume the "heely" position.

        Once you get them, you will not get this position right away. It takes a few minutes. At first, I thought something was wrong with me. But then I kept trying and I got it.