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From Flying in the Military to Launching a Business

How one military man's experience prepared him for the entrepreneurial life.
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I’ve had two careers in my life: tech entrepreneur and military officer. On the surface these appear completely divergent, but in reality, military experience cultivates excellent entrepreneurial traits that most other career paths just can’t effectively emulate.

The traits I developed in the military have undoubtedly made me a better entrepreneur. Here are some examples:

Being comfortable with being uncomfortable. The military is constantly putting you in mentally and physically uncomfortable situations that require you to perform at your best.

Military: The second time I stood in the doorway of an airplane before jumping out of it I thought to myself, “I’ve already survived this once, why am I doing it again?” The adrenaline of the first jump was long gone, and at that point, I had to choose between accepting defeat or trusting my preparation, training and equipment. I chose the latter and lived to jump another day.

Related: What I Learned From the Military: Business Lessons From 8 Veterans in Franchising

Entrepreneur: As an entrepreneur, you’re constantly accelerating down a runway that’s still under construction. You need 10,000 feet to get airborne but only the first 6,000 feet of the runway are completed. You have to trust that you and your team will be able to build the remaining 4,000 feet before you crash.

Leadership during a crisis. When everything is falling apart, your team will look to you for leadership.

Military: As a brand new, 25-year-old KC-10 aircraft commander, leading my first overseas mission, I had a career-defining moment over the Indian Ocean when one of the F-15s flying on my wing experienced a serious in-flight emergency. Three weeks prior, I would have looked to my left to the person in charge for the plan. That day, when I looked to my left I saw nothing but ocean. When I looked back to my right, I saw three sets of eyeballs looking at me. It was time to lead. Fortunately, on that day we were able to get everyone to safety and complete the mission.

Entrepreneur: Recently, we had a major product bug make it into a release that caused our usage metrics, ratings and revenue to sharply decline, all while our CEO was on a well-deserved and much-needed break. Instead of destroying his rest, I, the guy on the team who does not write code, hopped in and worked with our team to get a plan in place to address the problem.

Related: Entrepreneurship Bootcamp Gives Wounded Veterans a New Life

Sleep deprivation. The enemy doesn’t care about your sleep patterns and neither does your startup.

Military: Any veteran will describe sleepless nights while deployed or being in harm’s way. The military will give you 26 hours of things to do and only 24 hours to do it in. You have to figure out what works for you and your body.

Entrepreneur: During the first two and a half years of our company, I worked a full-time job while co-leading the full-time startup. I also have two children under the age of 7 and a wife who works a full-time job. During those first couple of years, I couldn’t afford to sleep more than four to five hours per night or else I would have failed at something important.

Perspective. In the military, a day when you didn’t die or get someone else killed is a good day.  

Military: I vividly remember landing an airplane in absolutely horrible wind conditions. They were technically within legal limits but today I wonder if attempting to land was even the smartest decision. It was so turbulent that about a mile prior to touchdown I literally thought to myself, “If I fuck this up, we all die.” 

Entrepreneur: Recently, during the TechStars program, I was interviewed by a television reporter. In an attempt to communicate the dramatic importance of the event, he asked something to the effect of, “so what happens to your company if you bomb on demo day and can’t get any investor interest?” I paused, took in the question, and replied, “Well…the sun will come up, my family will wake up and go about their day, and we’ll keep grinding away on building this business.”

Although these stories are uniquely mine, they are not unique in the company I keep. I want to encourage more veterans to consider entrepreneurship, and more civilian entrepreneurs to consider veterans as co-founders and early hires. Neither group will be disappointed.

Related: How Military Veterans Are Finding Success in Small Business