Finished this book yesterday while at my hotel room in Salt Lake City.
A lot of what Machiavelli writes is applicable in situations today, whether it be realpolitik or corporate management. Which illustrates his profound insight and our lack of evolution in those social dynamics. I wonder what a new "The Prince" would look like in a post-Singularity world; would the concept of a Prince even be meaningful? Probably not. Let's hope so.
There's priceless stuff in Machiavelli's short book, and one picks up a bit of history along the way, though the structure, largely consisting of categorizations of the type "there are three reasons why..." "and this is caused by four factors, two of which can be further thought of in terms of two principal causes..." gets a little repetitive.
But surely, you gotta love a canonical book that contains uplifting nuggets like:
"Because this is to be asserted in general of men, that they are ungrateful, fickle, false, cowardly, covetous, and as long as you succeed they are yours entirely; they will offer you their blood, property, life, and children, as is said above, when the need is far distant; but when it approaches they turn against you."
This reading follows closely after watching a documentary on the book by Discovery Channel, made interesting by interviews with the likes of Henry Kissinger on the influence and meaning of this book.