Consider spraying your hair with a heat protecting spray. This will help keep your hair from getting damaged while you blow dry it.
Use a round, tube-shaped brush, not a paddle brush.
Remember to use a heat protecting spray before using the flat iron. Flat irons get much hotter than a hair dryer and can cause more damage.
Some people find it easier to use a special loop made for flipping ponytails. You can also bend a pipe cleaner in half and use that instead.
If you are having troubles getting the ponytail through the hole, try widening the hole a little bit by inserting your first two fingers and spreading them. You can also try pushing the ponytail through the hole.
This style works best with straightened hair.
Instead of pointing the end of the comb straight back, consider angling it slightly towards the center-back of your head.
This works best with hair that falls somewhere between your shoulders and your elbows. If your hair is too long or too short, it may not be as effective. Use a small, less dramatic motion. This will help make it look more natural. If you try to make a huge show of your hair flip, and make a large gesture, you will look overly dramatic and unnatural.
Depending on the length of your hair, you might end up catching someone in the face.