How William the Conquerer Invented Humility

Following is the never-before published introduction for

The Humility Imperative

In 1066, William the Conqueror became the king of England. He kicked off his reign by confiscating land from Saxon lords and allocating it to members of his own family—he also tossed a few acres to the Norman lords who helped him overthrow the country.

This was pretty much a major bummer for those who already lived on the land.

They were deemed common people. Peasants.

The designation bore more pain than unfortunate classification: they were required to provide services to the king, and for that, they received protection and were able to continue living in their feeble huts.

Of course, King Willy wasn’t all bad. He threw lord-like bashes for those in the upper class. And, after choosing the best cuts of meat for his festivities, he passed on the scraps to the peasants. (Hey, c’mon, it would be hard for them to provide services if they starved, right?)

These leftover meats, they had a name. They were called umbles.

And that’s where the word humble originated.

Over the course of time, humble became associated with anything deferential. Indeed, humble pie is now what you eat when you exist in a lowly station.

Humility, thus, is what you have when you are humble—providing some logic to why humility is defined as having a modest view of your own importance.

Fast-forward a few centuries and here I sit contemplating the very nature of humility. Frankly, it confuses me.

• I’ve run seven startup companies. One was acquired for $60 million and another for $150 million.
• One of my companies was the cover story of a New York Times Magazine article.
• For years, I served on the global executive team of a $1 billion revenue company with 2,500 employees.
• I’m a (slightly reformed) venture capitalist and have personally invested in north of fifty startup companies on my own.

Early in my career I was unequipped to balance my abilities with the perception of myself. I can imagine a few folks considered me a narcissist. Arrogant. An egomaniac.

A complete and utter asshole.

But over time, the sharp edges have dulled. I’ve received executive coaching and I’ve been part of team exercises that border on therapy sessions. With a bit of success, I no longer have to race to prove results; I’ve become more comfortable in the marathon versus the sprint.

But in order to build a company, one has to inspire a team. In order to woo investors and manage boards of directors, one has to make strong decisions. In order to invest capital in someone else’s startup, one has to have conviction. In all cases, one has to have confidence.

Which begs the question: can one be confident and have humility at the same time?

The Humility Imperative—the concept—is the assignment of that question.

In order to explore that, one needs to understand that humility may be intended in one’s heart, but only becomes genuine if it is reflected through the thoughts of others. The lessons are a reminder that every interaction—both professional and personal—is the lens by which your own intents become clear. Humility is an imperative. It lives in the eye of the beholder.

The Humility Imperative—the book—delivers authentic, raw evidence that building anything requires constant attentiveness to interpersonal dynamics.

Central to that are the professional relationships that fuel any business growth: teams, investors, managers, peers, and clients, as well as current, potential, and even ex-employees.

Many chapters of the book focus there.

Yet those relationships pale compared to the significance of the personal relationships required for the leadership journey — the individuals who provide unseen support, criticism, and love. “The significant other.” “The spouse.” Nay, the passenger who is along for the ride, whether they like it or not. While often overlooked in the broader narrative of stories of success and failure, the impact of these relationships can’t be simplified, obfuscated, or overstated.

Building any company is like guiding a rowboat in the middle of the ocean: massive swells and troughs require one to hold on tightly while bounding between sheer terror and supreme elation. You may find the chapters of this book follow that rhythm. Be prepared to climb aboard.

The rises and falls may be unintended consequences of the journey, but the silver lining is that they force behaviors to ensure execution through strength of leadership.

Those behaviors often require confidence.

And always require humility.

BONUS: 4 chapters in The Humility Imperative originally appeared in Hacker Noon. You can read them below:

All VCs are Dicks

The 20 slides that Raised $7M

Two Tales of Transmoral Leadership

Notes on Nutting Up