When I left the military, it was to be my own boss. It didn’t work out so well at first, but after a few false starts, including getting kicked in the teeth a few times, I finally found something that I enjoyed doing—writing and publishing—and I turned it into a business.

I’ll start from the beginning, but before I do that, let me explain something. The reason I’m writing this new “Military Millionaire” series is to empower transitioning military veterans with the knowledge to become financially independently. The transition classes I received when I got out were good, they just didn’t provide enough information for me.  Also, I’m tired of the military “hero-or-victim” narrative spun by most of the American media, because it’s bullshit, all it does is box veterans into a corner. Military veterans are some of the most capable people I know: They show up on time, take responsibility for their actions, and can manage others effectively. I know because I am one, and employ more than a dozen veterans through Force12 Media and SOFREP.

I want to share the story of my transition from military life to my 10 years of experience in business, the executive world, and entrepreneurship. My primary goal is to help military veterans avoid simple mistakes that cost me dearly, and give them an opportunity to learn from the experiences that made a positive difference in my transition. This will also include interviews from successful veterans of industry. So now that we got all that out of the way, it’s time to get down and dirty.

A short personal history of my transition: I was a 29-year-old Navy SEAL chief petty officer with a young family. I made over a quarter million dollars buying small houses and apartments while on active duty, and I was hooked on real estate (always a great investment if you buy right). That led me to start reading books on investing and business (a good place to start for anyone). If you want to be successful, start reading about other successful people and their experiences. Then I did some simple retirement math, and realized that if I stuck around another 7-12 years (this would put me at 20 or 25 years in), I wouldn’t just be physically broke, I’d be financially broke as well. I had great income as a Navy SEAL because of all the special pays that added to my base pay, but only my base pay would factor into my retirement pay, so in essence, I would get the same retirement as a Navy cook (no offense, cooks!). Hopefully this changes in the future, but it was that way in 2006 when I took the jump and left active duty.

Let’s also get this straight: I’m not advocating leaving your retirement on the table. There are great benefits that come from retiring at 20 years, such as military family medical—a very important asset (more so now than ever because American healthcare is a nightmare). If you were to ask me my advice on staying longer than 20 years? Unless you’ve got a star on your shoulder, get the hell out because you’re wasting time, and that’s one of the most precious things we have.

So there I was, on active duty, meritoriously promoted to E6 at sniper cell, then selected for CPO my first at-bat while acting as the West Coast Naval Special Warfare Sniper Course manager. I was having a great career, then realized my fun meter was pegged, my back hurt, and I wanted a better life for my family. I pulled the plug.

My goal was to contract with a three-letter agency to ease my transition and start my first business. I had my first overseas deployment date as a contractor before my terminal leave ran out. I was leaving the military, and I was scared shitless. I didn’t know anything about business or how my skills would translate, but that didn’t bother me. I just knew I’d figure it out. Because military people are problem solvers, if they don’t know the answer, they know who to ask, and how to just get it done.

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It was one of the best decisions I ever made.

In the following article, I’ll cover starting or buying a company, raising money, and navigating business bank loans.

Main takeaway: Have a clear vision for your retirement or early transition out of the military. You’re either doing one or the other, so start planning for this now. Read books and start gaining knowledge. Decide what your plan is—the simpler the better—and don’t rule anything out, even if it’s moving to a foreign country to live like a king on your military retirement! I’ll cover this idea, too, because it’s an option—more so if you don’t have kids. Let me know what you think in the comments below, and please share this series with someone you think it would help.

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Photo: Author’s collection. Contracting in Iraq, 2007

(Featured image courtesy of web-mech.net)