Machiavelli's Other Book Is About Republics Actually

Published on August 28, 2024

Machiavelli and his domain

The Context Thing

So here’s a fun story about Niccolò Machiavelli. Everyone knows him as the “ends justify the means” guy who wrote The Prince, that cynical handbook about how to be a ruthless dictator. But here’s the thing: Machiavelli actually preferred republics! I know! The guy whose name literally became an adjective for scheming political manipulation spent most of his intellectual energy writing a massive love letter to republican government. It’s like finding out that Gordon Gekko’s favorite book was actually about credit unions.

The book is called Discourses on the First Ten Books of Titus Livy, which, okay, is not exactly a beach read title. Machiavelli wrote it between 1513 and 1519, roughly the same time as The Prince, but the circumstances matter here. See, Machiavelli had what we in the finance industry call a “career event.” In 1512, the Medici family rolled back into Florence after the republican government collapsed, and Machiavelli, who’d been Secretary to the Second Chancery of the Republic of Florence, basically a senior bureaucrat and diplomat was immediately:

  1. Fired
  2. Exiled
  3. Tortured (they used something called the strappado, which I will not describe)
  4. Eventually released to his farm to write angry books

This is sub-optimal career progression.

The Unemployed Guy Writing About Management

So there’s Machiavelli, sitting on his farm, professionally destroyed, personally humiliated, and what does he do? He writes TWO books about politics. It’s like getting fired from Goldman Sachs and immediately starting a Substack about optimal banking regulation.

The Prince was his job application dedicated to Lorenzo de’ Medici, essentially saying “hey, I know you guys tortured me, but I’m really good at this politics stuff, maybe hire me?” (Spoiler: they didn’t.) But the Discourses was different. This was Machiavelli writing for his friends, for posterity, for the sheer intellectual pleasure of figuring out how republics actually work.

The structure is delightfully weird. Livy was a Roman historian who wrote about the early Roman Republic, and Machiavelli uses Livy’s history as a jumping-off point to talk about… everything. It’s like if someone today wrote a book called “Thoughts on Reading Michael Lewis” and used it to explain their entire theory of financial markets. Actually, that’s not a bad idea.

The Republican Machine

Here’s what Machiavelli figured out, and it’s kind of brilliant: republics are antifragile (to use Nassim Taleb’s word, which Machiavelli would have loved).

The basic Machiavellian insight about republics goes like this: You know how in The Prince he says rulers need to be feared rather than loved? Well, in republics, the whole system runs on controlled conflict. You’ve got:

  • The nobles (who want to oppress everyone)
  • The people (who want not to be oppressed)
  • Some kind of institutional structure that lets them fight it out without actually killing each other

It’s like checks and balances, but messier and more honest about human nature. Machiavelli looks at Rome and says: “These guys were constantly having internal conflicts between patricians and plebeians, and that’s WHY they succeeded, not despite it”

This is counterintuitive! The conventional wisdom in Machiavelli’s time (and honestly, in our time too) is that you want unity, harmony, everyone pulling in the same direction. Machiavelli is like: “No, no, no you want productive tension. You want the investment bankers and the regulators to be in permanent conflict, because that’s how you get a system that actually works.”

The Startup Founder’s Guide to Ancient Rome

What makes the Discourses fascinating is that Machiavelli treats Rome like a case study at Harvard Business School. He’s constantly asking practical questions:

  • How do you set up institutions that channel ambition productively?
  • What do you do when your republic gets too successful and rich? (Spoiler: it’s bad)
  • How do you prevent some charismatic strongman from taking over?
  • What’s the optimal amount of inequality? (Some, but not too much)

And here’s the kicker: unlike The Prince, where Machiavelli is explaining how one person can gain and keep power, the Discourses is about how to build systems that don’t depend on one person being good at their job. It’s the difference between “how to be a successful day trader” and “how to build a functioning stock market.”

The Fortune Thing

Machiavelli has this whole riff about Fortune (which he personifies as a woman, because 16th century) that’s way more sophisticated in the Discourses than in The Prince. In The Prince, Fortune controls half of everything and you just have to be bold and grab her. Very trading-floor energy.

But in the Discourses, he’s like: “Actually, good institutions can hedge against Fortune better than any individual prince.” A republic with strong institutions, good laws, and that productive internal conflict we talked about? That’s diversification, baby. One bad leader won’t tank the whole system.

Why This Matters (The Money Paragraph)

Look, the reason people should care about the Discourses today isn’t because we need another take on Roman history. It’s because Machiavelli is asking the fundamental question: How do you build political systems that account for the fact that people are, generally speaking, the worst?

His answer which is republics with lots of institutional conflict, checks on power, and channels for ambition feels weirdly modern. Or maybe modern democracy feels weirdly Machiavellian. Either way, the Discourses is Machiavelli saying: “Look, I told you how the sausage gets made in The Prince, but if you actually want good governance that lasts, you need a republic.”

The irony is delicious. The guy whose name means “evil schemer” actually thought the best government was one where no single schemer could win. It’s like if Bernie Madoff’s secret passion project was designing better SEC regulations.

The Lesson

So Machiavelli is sitting there in exile, career destroyed, probably drinking whatever the 16th-century Italian equivalent of whiskey was, and he writes two books. One (The Prince) makes him infamous forever as an amoral monster. The other (Discourses) contains his actual political philosophy: that republics are better than principalities, that conflict can be productive, and that good institutions matter more than good leaders.

The lesson here is either:

  1. Be careful which book of yours gets famous, or
  2. If you’re going to get tortured and exiled anyway, you might as well write what you really think

Also, maybe read the Discourses? It’s actually pretty good, and way less likely to get you called Machiavellian at parties.