The quote that I picked isn't necessarily the most outrageous thing that Machiavelli wrote, but it is one that I particularly liked.
"A prudent man should always set out on paths beaten by those who are truly great and worthy of imitation. This way, even if his own skill does not attain the same heights, he can at least expect to achieve some of the effect."
I believe that Machiavelli is correct in his statement. But the most important thing in this statement is that this can only be achieved by a "prudent man." This means that the person undertaking this endeavor must be at the least, competent. He (or she) doesn't need to be as great or fantastic as the person that they are following in the path of, but they must have some skill. A complete idiot cannot follow after the path of someone as great as say the Founding Fathers of America. But someone who knows a thing or two can attempt to achieve what they did, and even if they don't get the full effect, they can do some good.
Machiavelli went on and spoke of how an archer who knows his own skill, as he is aiming at a target far away will aim higher then the sighted target so that when the arrow falls short, it will be close to the mark. This might be the origins of the saying "shoot for the moon, because if you miss, you will still land among the stars." Machiavelli said many things that upset a lot of people, but overall I believe the man was quite intelligent, just blatantly honest about tough subject matter.