Yes, you read that right. The West’s roaring lion, the British Bulldog, he of “blood, toil, tears, and sweat”—Sir Winston Leonard Spencer-Churchill—“customarily wore underwear made of pale pink silk.” We’ll come back to that later.
I was recently asked to speak at a Defense Entrepreneurs Forum panel at the US Air Force Academy, which got me to thinking about what that actually means. Some hold the term, “defense entrepreneur,” in contempt: Why isn’t this just innovation? Why do we have to go and create a new word for the same thing?
Those folks would be wrong. Just as there’s an important distinction between a “driver” and “driving,” there is a useful difference between an entrepreneur and innovation. One is a dynamic process; the other, a human catalyst that propels, advances, and often guides this dynamic process. Related, but not the same. The military spends a lot of time and ink on innovation, but not nearly as much on the individual innovator—the defense entrepreneur.
Winston Churchill was such an entrepreneur, with some noteworthy successes in his early career as First Lord of the Admiralty (akin to the American Secretary of the Navy): he was in favor of using airplanes in combat, replaced coal with oil on Royal Navy ships, and helped develop the tank, all of which proved to be meaningful innovations in the First World War. There were, of course, blemishes, not the least of which was his support for the eugenics movement, or his entrepreneurial, yet disastrous, strategic move in World War I to land British and allied forces at Gallipoli in the Dardanelles, a failed attempt to punch open a line of support to Russian allies and force the Germans into a fully resourced two-front war. Ask the ANZACs; that wasn’t pretty.
And neither is entrepreneurship, particularly defense entrepreneurship, if done poorly. (Note: this essay steers the “defense” term toward those in active military or government service; it should be noted there are those in industry and commerce that might be conceived of as “defense entrepreneurs” as well—yet, this essay hews specifically to the former, less to the latter.)
The stakes are higher on the battlefield than they are in business; failures can get a lot of people killed. That’s why it matters that we understand some fundamental principles about defense entrepreneurship, so as we go about seeking innovative, better ways of doing things, we do it with a keen understanding of the inspirational flame that enables defense entrepreneurship—so it lights the way instead of burning us up.
Many are familiar with serially successful entrepreneur Peter Thiel’s bestselling book, Zero to One, in which he defines the divergence between going from zero to one (doing entirely new things) and one to n (copying things that work). Both are important processes to business people and offer a useful way to frame defense-specific entrepreneurship.
Defense entrepreneurs have one extra step, organizationally and strategically. They don’t ever go just from zero to one. Warfare doesn’t merely create new political societies out of nothing. They must first break what came before. Military efforts typically first destroy, and then create, geographic monopolies on violence. When successful on both counts, as Allied efforts were against Germany and Japan during and after the Second World War, the results are spectacular. When unsuccessful, well, not so much.
The same is true with American defense organizational change. The US Department of Defense is the world’s largest employer, bigger than China’s People’s Liberation Army, Walmart, and McDonald’s. The Department of Defense has been around, in some form, for over 240 years. So there are a great many pre-existing structures.
In both those arenas, strategic and organizational, American defense entrepreneurs fundamentally must do two things: creative destruction (go from one to zero) and creative construction (go from zero to one). Even Clausewitz would agree with this point, which is why he defined war in two ways: as an act of force (the destructive aspect) and as an act of policy (the constructive imperative).
My own experiences in bringing change, in part through the growth of the Modern War Institute, as well as some theory and common sense, have led me to ten principles that are meant to explain a bit of the imperative (the Why?) and the best practices for the budding defense entrepreneur (the How?), and ultimately to address a question: What does this mean for those in uniform that choose the entrepreneurial path?
Why must we seek out and support defense entrepreneurs?
These three imperatives function at different, yet interdependent levels.
Strategic logic: War’s outcome is governed by many factors, but, one at the very core is what Edward Luttwak has described as the “paradoxical logic” of strategy. He reminds us that the enemy’s presence means war will always be a counterintuitive endeavor in which a good road is a bad road because it is a good road (and the enemy will likely attack there). Likewise, what worked yesterday won’t work tomorrow because it worked yesterday. The surest way to battlefield death is to do what the last guy did.
I was in Korea recently when a senior officer told a group, “If another Korean War comes, when society collapses in the north, it’ll look like Iraq—members of the regime going to ground, starting an insurgency, setting IEDs.”
Of course, that might be right. But what struck me is how much it was based on personal experience in Iraq. And Iraq is not Korea. Each war is unique. Strategic solutions rarely translate. And yet military thought is so often tragically guilty at pounding old ideas into new wars, imprisoning minds into pre-judged cages with steel bars forged in Iraq or Afghanistan (or wherever the last war was).
And so we have to break the wheel to reinvent it for war—precisely because our opponent is a living, willed enemy and will know the shape of our last wheel. (Yes, I’m aware that you’re thinking, “destroy the village to save it,” and, yes, at war, where up can actually be down, that might be the best solution—see Moscow, circa 1812 for more on that point.)
We’ve got to have wheel breakers.
Organizational need: Jeff Bezos, Amazon’s CEO, has acknowledged “companies have short life spans” and he believes it is “inevitable” that “Amazon will be disrupted one day.” Think Sears, Circuit City, Kodak, and other enormously famous companies that went the full march from Good to Great to Below Average. We often think about how creatively innovative Amazon is, and, at one point, many people held the same sense about these other, eventually marginalized companies. But then this feeling fell off because other another, newer, better businesses came along and disrupted them. And they were decimated or swept away.
But there’s no sweeping away the US military. It might be thought of as a company that’s served the same shareholder for going on two and a half centuries. In those terms, it is clear there’s a duty to reinvent, change, and fit the times to stay relevant—even more so than at Amazon.
Survival instinct: This might be taken straight from Charles Darwin’s elegant theory of natural selection through the small variations that increase an individual (or group’s) ability to compete, survive, and reproduce. In short: adapt or die. This merciless model functions effectively at every level of war. What traits survive? Which ones thrive?
Those propelled by nothing more than the will to survive might be the most effective entrepreneurs in defense.
How does the defense entrepreneur function for maximum effectiveness?
Always be questioning: This orients the entrepreneur to problems that need solving. Peter Thiel’s close business partner, Eric Weinstein, asks a particular question whenever he’s evaluating a company: What is it that they can’t afford to say or think? Translated, his query cuts to the heart of many underperforming organizations. But this question shouldn’t be limited to business. A defense entrepreneur must be willing to ask not only piercing, quality questions, but also produce a mass bombardment quantity of questions—because only that intellectual shovel work will uncover the buried details that matter most. Lives depend on it.
Comfort the afflicted and afflict the comfortable: Finley Peter Dunne coined this maxim to describe ideal journalism, but it is also how the defense entrepreneur’s mind best functions. In many ways, the two greatest sins in America’s modern defense establishment are: (1) the social harm directed at individuals that’ve been persecuted for trying something new and failing or, worse, having a new idea that would cause change (denigrated as the “Good Idea Fairy”), and, (2) those that’ve given in to the comfortable (AKA “lazy”) way of doing things.
The defense entrepreneur counters both these sins. First, by providing aid and comfort to those that have stood out on a limb, tried something new, taken the initiative, and failed. Second, by rigorously afflicting flawed ideas. Because, as Luttwak would counsel, failed ideas eventually lead to successful ones and, as Churchill might have said (despite probable misattribution), “success is going from one failure to another without losing your enthusiasm.”
Modern persistence hunters: Harvard evolutionary biologist Daniel Lieberman has found that for thousands of years, mankind hunted animals with very basic tools like knives and spears. So limited were these weapons that humans were unable to kill for food from a distance. How did they do it?
Persistence. More specifically, early humans would gather hunters, herd animals, and then run them down until the animals over-heated (because humans cool more efficiently than many of the animals they hunted). In short, we ran them to death.
Today, the established, entrenched bureaucracy, which is truly effective at what it does (we get paid on time!), also means that any change is like turning the Titanic. Manually.
Persistent pressure over time is often the only way. The adoption of new ideas in an American defense setting is better measured by calendar than clock, and takes a commitment on par with those early hunters running to survive.
What does this mean for the modern defense entrepreneur?
You have to be so good they can’t ignore you (even if you wear pink underwear). Churchill wasn’t so destined for greatness as the popular imagination imagines. No university degree. His mother was American in a British society. He was forced to turn to journalism to make ends meet. He drank heavily. He spent over a decade in the political wilderness. He was mocked relentlessly by political rivals (not necessarily for his silky pink underwear, though that cannot have helped).
But he remained true to himself, as committed to his convictions as he was to his penchant for unconventional undergarments, and on one point—the Nazi threat to Europe in general and Britain in particular—he was exactly right. His will and words in 1940 were so powerful they kept the British in the war when their weapons weren’t enough.
Insider, outsider, intrapreneur, extrapreneur, technophile, technophobe—none of the labels matter if your ideas aren’t demonstrably better and you’re not ready to compete. It is fine and good to have an arsenal of ideas—but if you’re not prepared to use them, then they’ll never leave the arms room. Churchill was right at the right time and nobody could argue effectively otherwise. So must be the successful defense entrepreneur.
Your name will not appear in bright lights. This isn’t Shark Tank and you’re not Mark Cuban. While wearing a uniform, even if your ideas save millions of dollars or thousands of lives, you will be paid as much as anybody else of your rank; not a dollar more. So if your motivation is for fame and finances, find somewhere else. I hear Silicon Valley’s nice this time of year.
But if your satisfaction comes by way of intrinsic means, stick around. Because there’s nothing more righteous than having and implementing a novel idea that better protects and serves your country.
You will fail. This is both a principle and a challenge to the defense entrepreneur. Unfortunately, the military doesn’t teach this well: the core cultural flaw of the military service academies, for example, is that they do not support failure (Consider Gen. MacArthur’s dictum: “there is no substitute for victory”).
But we’ve confused sports with strategy; forgotten what field really matters. If our aim is flawless victory, achieving perfection, then we’re not seeking the challenges that stretch us and pull us to newer, higher limits. And every day you’re not pushing yourself to a new limit you’re making yourself weaker, a fact that might just matter someday on some distant battlefield. This is the laziness of limited success. My lived experience is that all the best things in my life have been born from failure.
You will not be a general. If you want to be a defense entrepreneur in uniform, you may save lives, you may make battlefield wins and strategic success possible, but you will not be popular. Max Brooks has noted that human communities were (and are) built on the social strength that comes through solidarity. Security by cohesion.
But defense entrepreneurs come along and say, “this could be better,” an inclination that inherently rocks the boat and aggravates others.
This friction typically means you will not be promoted as rapidly as those that choose the well-established Great Ladder to the Stars. By spending so much time focusing on a better way, you’ll likely miss several steps on that Ladder.
If anything, defense entrepreneurs know there’s always another option. Churchill was never a general; his active military service ended when he was a lieutenant. But he also won a war, perhaps due to, and not in spite of, his predilection for fancy pink underwear.
