The short version is that Machiavelli is a rather profound Stoic philosopher, but everyone misses that in a lot of his work he is being slightly sarcastic to throw the "powers that be" off the scent that he was criticizing them. When you hear how he suggests that "Princes should be feared rather than respected." he actually calling out the despots of his day. It's kind of how Stephen Colbert portrayed a right wing pundit on "The Colbert Report" as a way of satirizing right-wing pundits.