Most people would tend to think that women are the only ones who are interested in celebrity hairstyles; this couldn't be further from the truth. While most men may not want to admit it, they are just as interested, they are just quieter about it.
The best way to get your ponytail in instead of trying to fight with all the hair at the back is lean forward and brush all your hair down to your face. Bring all of the hair from the back forward. Once you have done this then you can gather all of your hair in one bunch and apply the holder that you are going to be using.