The Prince – Bookcast #16

The Prince (1532) by Niccolo Machiavelli

The most famous (and infamous) book on politics ever written. The Prince was initially denounced as a collection of sinister maxims and a recommendation of tyranny. It is, in reality, the first description of the science of politics as they are ACTUALLY practiced rather than as they SHOULD be practiced.

As a young Florentine envoy to the courts of France, Spain and the Pope, Niccolò Machiavelli (1469–1527) was able to observe what rules a monarch must follow to stay in power – and which rules would lead to his failure (and often his death).

500 years later, The Prince has only grown more influential. Machiavelli’s timeless wisdom and ruthless cunning are more relevant now than ever. If you want to achieve power and maintain it, this book is required reading.

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“The Prince” Show Notes

0:00 – Intro to “The Prince”

  • Very brief historical background: Prior to the writing of The Prince, Machiavelli had spent 14 years on the war council of Italian city-state of Florence and was one of the most influential diplomats in Italy. Then the powerful Medici family returned from exile, dissolved the Florentine city-state, and removed all government officials – including Machiavelli.
  • Machiavelli wrote The Prince in an attempt to gain favor with the Medici family and regain his political position. The book is dedicated to the young prince Lorenzo de Medici. Machiavelli distills decades of diplomatic knowledge down into a single book designed to instruct the young prince on what he must do for his principality to succeed.
  • Intended audience: Anyone who wants to become more powerful, anyone who believes the world is a kind, gentle, safe place, and every scholar or student of the dark art of politics
  • Who won’t like it: People who insist the world is a kind, gentle, safe place, people who need to classify all actions as right or wrong, people who only watch Disney movies and romantic comedies

6:00 – How easy is the book to read?

  • Difficult. Although the Mansfield translation is very readable (and filled with vital footnotes), The Prince discusses 500 year old Italian history and politics and they take time to learn. But the greatest challenge is wrestling with Machiavelli’s amoral – and sometimes immoral – political advice.
  • Print: 160 pages (5-8 hours to read – many, many more hours to study and digest)
  • Audio: 5 hrs 15 minutes

6:30 – Reviews and significance of “The Prince”

  • Dozens of versions and translations available, all of them popular on Amazon
  • True number of readers = Unknown (Millions upon millions over the last 5 centuries)
  • Because of multiple copies of the book, hard to say how many thousands of reviews (maybe 5k? 6k?) — All of them are roughly 4.5 stars
  • Currently: 
    • #1 Amazon – Modern Renaissance Philosophy
    • #5 Amazon – History of Renaissance Europe
    • #7 Amazon – Philosophy (entire category)
    • #48 Audible – Renaissance History
    • #92 Audible – Classic Literature (entire category)

9:45 – Bio of Niccolo Machiavelli

  • Niccolo Machiavelli was an Italian Renaissance diplomat, philosopher, historian and playwright who lived in Florence during the end of the 15th and early 16th century.
  • Machiavelli was born in a chaotic era of shifting city-states, where Italian noble families constantly battled amongst themselves – as well as with France, Spain, and the Holy Roman Empire – for regional influence and control. 
  • Five years after the Medici family had been expelled from Florence, Niccolo was appointed to the position of secretary of the Florentine Council for Diplomacy and Warfare. He was an advisor for 14 years…until the Medici family returned to power.
  • During his tenure, the Florentine government sent Machiavelli as a diplomat throughout southern Europe to help negotiate various conflicts, including to the courts of King Louis XII of France, King Ferdinand of Spain and the Pope in Rome.
  • Niccolo’s success ended abruptly when the Medici family returned to power and dissolved both the republic and the Florentine city-state. Sensing Machiavelli’s power, they accused him of conspiracy and had him first banished for a year. Then he was arrested, sent to prison and tortured. 
  • Eventually the Medicis released him from prison. After being stripped of his power, Niccolo spent the remainder of his life outside of government and instead devoted his life to writing.
  • Along with his political works, Machiavelli also wrote several highly popular plays that won him fame and some financial success.
  • Machiavelli wrote more than a dozen major works of political history and theory, including an eight-volume history of Florence, his classic Discourses on Livy (one of the first significant books on Republicanism) and of course The Prince.
  • None of Machiavelli’s books on politics or history were popular during his lifetime. His two most famous books – Discourses on Livy and The Prince – were published after his death.

12:00 – Major Themes of the Book

Free Will

  • Fortune is a “woman” who can be countered, but who must be defied with boldness and brashness. 


  • It is safer for a prince to be feared than it is for him to be loved. Men dread punishment, and this fear can be used to a prince’s benefit. 
  • Love can lie, but fear is a primitive emotion that will not change at the tip of a hat
  • A prudent prince will therefore use cruelty to his advantage – though only when necessary.
  • Cruelty is well-used when it preserves a prince’s safety or secures the state; gratuitous cruelty is to be condemned. 


  • Princes should be both men and animals, intellectuals and warriors. When it comes to animals, they should be both lions and foxes, with the lion representing sheer force and the fox representing craftiness.
  • A prince should always use his own troops and not rely on mercenaries and auxiliaries. 
  • Politics is always bathed, necessarily, in blood.


  • “A prince should read history and reflect on the actions of great men.” 
  • In order to be great, one must study the greats of the past, and in order to avoid pitfalls, one must examine the mistakes of failed predecessors. 


  • Generosity is often dangerous for a prince. It is better for a prince to be thought a miser to keep his state financially secure, and to reserve money for when it is most needed.
  • If a prince showers his subjects with gifts in order to curry favor, he winds up depleting his own resources, so that in the end he must take back his gifts from the people in order to keep the state afloat.

The Unification of Italy

  • The Prince ends with a call to a unified Italy. 
  • Machiavelli explicitly addresses Lorenzo de Medici as the potential savior Italy has been yearning for: “There is no figure presently in sight,” he writes, “in whom [Italy] can better place her trust than your illustrious house…favored by God and the Church….who can take the lead in this process of redemption.”
  • This unification is invoked in symbolic biblical terms as a “mass salvation” with the prince unifier as “messiah” – a fascinating finale to a book that seems so secular and amoral on the surface.

16:30 – Jay’s Perspectives

  • What did you like best about The Prince? 
    • It feels like a guidebook – maybe THE guidebook – for 21st century politics.
    • Smarter, wiser and more clever than any other book on politics I’ve ever read.
  • Share a favorite quote (maybe 2). Why did this quote(s) stand out?
    • “[A]ll the armed prophets conquered and the unarmed ones were ruined. For…the nature of peoples is variable; and it is easy to persuade them of something, but difficult to keep them in that persuasion. And thus things must be ordered in such a mode that when they no longer believe, one can make them believe by force.”
    • “[M]en will always turn out bad for you unless they have been made good by a necessity.”
  • What did you learn from this book / How did this book change you?
    • It makes me want to accomplish more; set my sights higher; think grand.
    • It also made me ask the question “Is changing the status quo ever going to be unopposed? Was any nation, territory or thought-space ever truly unoccupied before it was ruled?”
  • What did you like least (critique)?
    • Honestly, there’s so few things I dislike about this book…I’d say the one thing I really want is for Machiavelli to come back from the dead 500 years later and write another book for the modern era. But honestly I don’t think he’d change much.
  • What question(s) would you ask the author?
    • You wrote comedic plays, romantic poetry, long histories and razor-sharp political commentary. Which was the most fun?
  • Any other related/connected books that you’d recommend to others?

24:00 – Matt’s Perspectives

  • What did you like best about this book? 
    • I love the deep insight contained – it reads like it is about current times instead of being 500 years old
  • Share a favorite quote (maybe 2). Why did this quote(s) stand out?
    • “Everyone sees what you appear to be, few experience what you really are.”
    • “The first method for estimating the intelligence of a ruler is to look at the men he has around him.”
  • What did you learn from this book / How did this book change you?
    • See people for who they are trying to be
    • How to gain and hold power
  • What did you like least? (critique)
    • Nothing, really. The Prince is excellent!
  • What question(s) would you ask the author?
    • I would live to hear his take on modern western politics
  • Any other related/connected books that you’d recommend to others?

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The Prince – Bookcast #16 2

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