Series · 7 parts
The Startup Prince
Machiavelli's The Prince, read as a guide to startups — the ways a venture that looks like growth is actually falling apart.
- 01On the Risk of a Vision Never Made ExplicitThe first post in a series that reads Machiavelli's The Prince as a guide to startups. We look at how a vision that exists but is never made explicit quietly scatters an organization in different directions.
- 02On the Risk of Making Money the Goal — The Paradox of Chasing It Further AwayThe second post in The Startup Prince. Even when a vision exists, money can quietly slide into its seat. We look at how that shift distorts an organization's decisions, borrowing Machiavelli's view of wealth as a byproduct rather than a goal.
- 03On the Risk of a Business Built on Contact Points — When the Founder's Network Is the Revenue StructureThe third post in The Startup Prince. We look at why early revenue built on a founder's personal relationships rarely lasts, borrowing the story of Cesare Borgia — who could not hold power built on borrowed strength.
- 04On the Risk of Scaling by Fortune Alone — Luck Opens the Door, Skill Holds the RoomThe final post in Part One of The Startup Prince. We examine the risk of mistaking growth carried by market tailwinds for one's own capability, borrowing Machiavelli's distinction between virtù and fortuna.
- 05On the Risk of Fighting on a Battlefield You Cannot Win — Courage Charges In, Strategy Chooses the GroundThe first post in Part Two of The Startup Prince. Which battlefield you end up on is largely a matter of luck; how you fight once you're on it is a matter of skill. We look at the risk of grinding it out on a losing battlefield, borrowing the way Machiavelli saw the Romans wage war and the half of life he assigned to fortuna.
- 06On the Risk of Dominating Instead of Leading — Obedience Reaches Only as Far as the Order; Understanding Goes Beyond ItThe second post in Part Two of The Startup Prince. Extracting obedience through the power of the office is not the same as leading people. We look at why an organization that runs on compelled obedience alone moves only while the founder is watching, borrowing Machiavelli's distinction between two kinds of power.
- 07On the Risk of Making Every Judgment With Your Own Eyes Alone — Trust Only Your Own Sight, and the Organization Closes Its EyesThe third post in Part Two of The Startup Prince. A founder's judgment is the asset that carried the company this far — but the moment it becomes the only standard for every decision, it shuts the organization's eyes. We look at why Machiavelli made the choice of ministers the first measure of a ruler's ability.