The legitimate way to get this Achievement requires you to play online with a friend. If the two of you play through the game starting from the beginning, this Achievement will unlock for both of you about half way through.
The other option, and one that is much easier, is to go to the Stark Enterprises common room and go back and forth between the lobby area and the secret Iron Man room behind the waterfall. You'll get this Achievement after about five minutes.
Of course, you could always turn on a second controller and do this on your own, if you'd rather not play online, or you don't have a Gold subscription.