All courses of action are risky, so prudence is not in avoiding danger (it's impossible), but calculating risk and acting decisively. Make mistakes of ambition and not mistakes of sloth. Develop the strength to do bold things, not the strength to suffer.

He who has annexed them, if he wishes to hold them, has only to bear in mind two considerations: the one, that the family of their former lord is extinguished; the other, that neither their laws nor their taxes are altered, so that in a very short time they will become entirely one body with the old principality.

Many have dreamed up republics and principalities that have never in truth been known to exist; the gulf between how one should live and how one does live is so wide that a man who neglects what is actually done for what should be done learns the way to self-destruction rather than self-preservation.

Gold will not always get you good soldiers, but good soldiers can get you gold.

it is much safer to be feared than loved because ...love is preserved by the link of obligation which, owing to the baseness of men, is broken at every opportunity for their advantage; but fear preserves you by a dread of punishment which never fails.

Nothing feeds upon itself as liberality does.

A wise man ought always to follow the paths beaten by great men, and to imitate those who have been supreme, so that if his ability does not equal theirs, at least it will savor of it. Let him act like the clever archers who, designing to hit the mark which yet appears too far distant, and knowing the limits to which the strength of their bow attains, take aim much higher than the mark, not to reach by their strength or arrow to so great a height, but to be able with the aid of so high an aim to hit the mark they wish to reach.