Key Takeaways

  • Machiavelli's Italy wasn't just unstable; it was built on systemic, unpredictable regime changes where current rulers were overthrown and their work undone by new enemies every ten years.
  • This environment, fueled by successive popes expanding military power and launching arbitrary wars, meant no "thread of legitimacy" could ever form in institutions or among the people.
  • Founders often plan for incremental change or adaptation, but Machiavelli's world shows what happens when foundational rules and allegiances are continuously ripped up by external forces.
  • Your startup's operating environment might appear stable, but understanding this extreme historical chaos reveals the deep fragility of relying on any long-term 'normal.'

The World Where Nothing Sticks

Imagine a world where the government you operate under is guaranteed to be overthrown every decade. Not just a new leader, but a new ruler who is almost certainly an enemy of the last one, and whose first order of business is to tear down everything their predecessor built. This wasn't some hypothetical thought experiment for Niccolò Machiavelli; it was daily life in 15th-century Italy. As historian Ada Palmer explains, Machiavelli lived in a "perfect storm" of political instability. Cities were in constant flux, with the "thread of continuity" repeatedly cut.

This wasn't just local squabbling; it was a systemic problem exacerbated by the Papacy itself. Palmer points out that “Over the course of Machiavelli's lifetime and just before, a bunch of consecutive popes expanded executive power, especially in the military side, and launched more wars, or did more arbitrary overthrow of governments.” These pontifical power grabs created a cycle of chaos. Every change of pope could mean a complete reordering of alliances, laws, and the very structure of governance. What little stability might emerge was short-lived, ensuring that “every ten years, you suddenly have a completely unpredictable new monarch who's almost guaranteed to be one of the enemies of the old monarch, and will therefore rip up and replace all of the things that that monarch tried to do with new things.”

In this environment, no institution could build traditions, and no people could truly invest in their current rulers. Palmer puts it sharply: “Practically every polity in this region has just had the thread of legitimacy cut. Its institutions have no traditions. Its people have no investment in its current rulers.” This wasn't just "change is hard"; it was an absence of foundational ground. It’s what happens "When a long thing cracks—boom, boom, boom, boom, boom—you get chaos." Machiavelli's famous realism wasn't born from cynicism, but from a brutally honest observation of how power operated when nothing was permanent.

Your 'Stable' World Can Be Machiavelli's Italy

Most founders build for a future of iterative progress. You launch, you get feedback, you pivot, you scale. You assume a certain baseline of market structure, regulatory consistency, or customer behavior. But what if your environment is more Machiavellian than you realize? What if a "new monarch" is coming for your industry, one who will rip up every convention, every partnership, and every market assumption you’ve built your company on?

Think about the sudden shifts in platform algorithms that can tank a business overnight, or a major regulatory ruling that redefines an entire sector. Consider the impact of a dominant new competitor, backed by limitless capital, who enters your space and disregards all previous norms. These aren't just market corrections; they can be the "thread of legitimacy" for your current business model being cut. Your team's investment, your customers' loyalty, even your investors' patience, might be built on traditions that suddenly no longer exist. If the entire operating logic of your market is reset by an external force, what do you do?

What to Do With This

Stop optimizing for a stable future; prepare for a radical, external reset. This week, identify the "new monarchs" lurking in your industry: a looming regulatory change, a dominant tech platform's likely strategic shift, or a well-funded competitor with a radically different approach. Run a thought experiment: what if these forces totally disrupt your market in the next 12-24 months? Outline how you would re-establish legitimacy for your product, re-engage your team, and rebuild customer trust if the previous "traditions" of your market were completely ripped up. This isn't about contingency planning for a small pivot; it's about building processes for rapid re-founding under entirely new rules.