receives compensation from some of the companies listed on this page. Advertising Disclosure


What Serving in Combat Taught Me About Startups

Jeffrey Chapman
Jeffrey Chapman

Starting a business requires a similar mindset to serving in combat. Here are some insights from the military that apply to entrepreneurs.

Serving in combat was the most daunting experience of my life, but the most challenging thing I ever did was start a business. When I share that truth with my fellow entrepreneurs, many of them look at me sideways and ask how I can possibly compare the two experiences. Here's what I tell them.

1. Forget what you've heard about entrepreneurship. You're on your own.

In the military, you know that the person fighting next to you, the pilots flying above the battlefield, and the support troops in the rear are all on the same team. Everyone in the military shares the same broad objective, even if their specific missions are unique. But during the initial stages of starting a business, entrepreneurs aren't likely to find many people in their corner. In fact, quite often, entrepreneurs are on their own until their vision and passion attract sufficient capital to hire a cadre of select early employees.

When it comes to forming a successful business, entrepreneurs are in a unique position. As founders, they are the only people with the singular objective of making the entire enterprise succeed. That's a big deal, especially during the early stages when a business is more of a concept than a concrete thing. All businesses are especially vulnerable at the beginning. In order for that idea to grow into a real business, you have to be there every step of the way – protecting, nurturing and growing the vision.

But let's talk about the people on your team for a moment. Your startup's first employees are crucial to your success. Most will come from your direct network. While your trust in them is high (validly so), they also have careers to manage, and sometimes that means putting their futures ahead of the organization. Investors want you to succeed, but they are hedging their bets and have their own obligations to make a profit, so typically, their ultimate allegiance is to their bottom line. And while strong advisors can offer valuable advice (mentored startups grow 3.5 times faster and raise seven times more money than others, according to one study), your success is never "make or break" for them because, quite simply, it's not their company. 

In my time as a military officer, these were difficult lessons to learn at first. After all, I came from a background where I was surrounded by people with the same ethos and objective as me. I never had to consider the possibility that the people I went to war with weren't as committed as I was. That alignment was a given – and that was a good thing.

The business environment isn't nearly so black and white. Your employees may not be motivated by the same things you are, your investors may not share your vision or its changing timeline, and your advisors might not agree with your decisions. None of this makes the business world a bad place, but good leaders have to recognize their operating environment for what it is. While every person connected to a startup is supposed to be on the same page in theory, a good leader recognizes that the reality is often quite different. In fact, I'd argue that nothing destroys a company faster than a leader who can't see where the incentives lie for everyone involved. 

A good leader understands that their employees are motived by career and financial goals that may diverge from the best interests of the company. A good leader sees that an investor's concern for their bottom line isn't always the same thing as the company's roadmap to success. And a good leader knows that even the best outside advice should be taken in context. None of this undercuts the value these people will play in your success; it simply highlights the potential for incongruence between your vision and the actions of others.

2. Every plan fails. It's how you respond to failure that matters.

For all of its complexity and confusion, war boils down to one thing: breaking the enemy's will to fight. Entrepreneurship is a similarly complex enterprise that boils down to three simple rules:

  1. Your new enterprise has to make money.
  2. You must have the skills and vision to lead the company.
  3. You have to want to do it.

But business has some other things in common with war too. At the outset, a favorable outcome in war looks achievable. Once you put boots on the ground, however, your plans and assumptions meet reality. Military leaders internalize this phenomenon through doctrine. As Prussian General Helmuth von Moltke put it, "No plan survives contact with the enemy." The quote is a famous one, but the second part of Moltke's thesis is equally important: "Strategy is a system of expedients." In other words, it's only possible to plan at the beginning. After that, strategy becomes a system of expanding or contracting options.

That framework is especially relevant to entrepreneurs. As one study put it, founders typically need two to three times longer than they expect to validate a business model. The same study found that 70% of founders eventually realize that their intellectual property isn't a competitive advantage. Anyone who has ever put together a business plan and pitched investors knows that a lot of thought goes into a competitive advantage and the time it'll take to validate the plan. Yet, just like any warrior on the eve of combat, we ought to know that our assumptions about what should happen will inevitably prove false. Just as a war plan won't survive first contact with the enemy, a business plan won't survive first contact with investors, competitors or customers. [Read related article: 4 Ways Military Service Prepares You for Entrepreneurship]

What this means is that success is about what you do after your initial plan falls apart. Business strategy is a system of options just like military strategy, which brings me back to the three rules of business. If you're not exploring options for your enterprise to make money, make your product possible, or sustain the will to continue doing what you're doing, you're headed for defeat.

3. The risk is total, so you must accept that you’re all in before you start.

In the military, you put your life on the line. We understand this when we join the military, and that fact is an omnipresent reality for everyone who serves as well as their families. Startups require a similar commitment. They aren't life and death, but entrepreneurs need to think about their commitment in terms of being all in for the business they're building.

It might be counterintuitive, but the reason entrepreneurs need to see startup risk as total is that almost all startups fail. Even the most experienced entrepreneurs fail; it comes with the territory. The important corollary here is that uncommitted or under-committed entrepreneurs never succeed. So here's the lesson: If you're not all in, you're putting yourself in a precarious position with the wrong mental attitude.

For me, the startup stakes were incredibly high. I took out a second mortgage on my house. There were times when I wondered if I would be able to feed my family or make payroll. Those weren't happy moments, but they were clarifying. I understood that I was all in for my business, and that feeling was similar to the commitment I felt in the military.

These are the gut-check moments when you truly understand that your only option is to push forward. Only by facing the reality of failure directly do you put yourself in a position to succeed.

Image Credit: jacoblund / Getty Images
Jeffrey Chapman
Jeffrey Chapman Member
Prior to founding Babel Street, the President of United States appointed me as the Deputy Executive Secretary for Economics and Finance at the U.S. Department of the Treasury. In that capacity, I developed financial strategies concerning the government overhaul of domestic capital markets and terrorism finance regulations. Before accepting my appointment to Treasury, I co-founded, led, and sold a software and consulting firm formed to meet post-9/11 needs of homeland and national security. I am a former naval intelligence officer and decorated combat veteran and an alumnus of the United States Naval Academy. I hold graduate degrees from the University of Virginia and Harvard University. As an Adjunct Professor at the U.S. Air Force Special Operations School where, I lecture on topics such as terrorism and geopolitics of the Middle East.