EDIT: I as well assumed you were referring to Sun Tzu. I can't speak to whether my comments hold for Machiavelli's at all.

If you've lumped "The Art of War" into the same category in your mind as Ayn Rand's writings, I suggest you to read it. You may find yourself pleasantly surprised. Aside from being both commonly cited as influential (in greater or lesser unfortunate ways), there's really about zero similarity between the two.