Attack Pilot To College Sophomore To Fintech Entrepreneur


[Nords note:  Tyson dropped by FinCon’s “Military Meetup” table in the exhibit hall to chat.  We had a great conversation about retirement calculators and financial independence.  He’s a vet, and he understands where military pay & benefits fit in a calculator.  You can learn more from the video at the end of this post, which is definitely NOT your typical fintech video.  If you want to learn more about the company, I’ve included a review from my rockstar blogger friends.]

[There are no affiliate links in this post, but take a look at the review (linked below) and support a veteran.]

[And now, here’s Tyson Koska’s story in his words:]

I joined the military for one reason only — the G.I. Bill.

I hadn’t considered that this decision, and the few years I’d spend in the military, would so heavily influence the rest of my life, but there you go.

I grew up exceedingly self-aware of my lower-middle-class situation. We lived in an affluent area, and I had a loving family — but if I wanted anything of “my own”, I had to buy it. As a 12-year-old, I did odd jobs — mowing lawns, painting houses, landscape stuff — but at 13, I became an entrepreneur. I opened T ‘N’ T Snowballs with a neighborhood friend and for the first time, I had “real” money of my own. The sweet taste of that cash would never go away. Having my own money meant I could make my own decisions, choices that were independent from what others thought I should or shouldn’t spend it on — money, literally, bought me freedom.

So as a senior in high school a few years later, when I failed to get the 4-year ROTC scholarship to Virginia Tech that I felt CERTAIN I would get — and faced with the prospect of living in my parents’ basement, taking classes at a local college, while also having to work to pay my car insurance and other living expenses — well, visiting the Army recruiter seemed like my only logical choice. When the recruiter told me I could go directly from high school to flight school AND have the G.I. Bill waiting for me when I got out — damn, I was sold!

 

Enlisted and in flight school

Sure, there was the ASVAB and FAST tests to contend with. There was an intrusive flight physical and interview with three high-level officers — but in the end, I shipped off to Basic Training in 1988 at 19-years old eager to escape the prospect of my parents’ basement and the same old roads to the same old places, and taking classes at some local no name school. At least, that’s what I thought I was eager to do.

Now I don’t know how it is in other branches, and I don’t know how it is now — but back then, the Army Warrant Officer program was fantastic. In basic training, they paid me as an E-3 and in flight school as an E-5. That E-5 pay (which many families live on) was the most money I’d ever made. And I was single, in Daleville, Alabama — and I got myself in crippling debt. Suddenly credit card companies were throwing themselves at me, and department stores couldn’t WAIT to let me take stuff from their store by opening their store-card. I can’t even count now how many $500 credit-limit store-cards I accumulated during that year — enough that even with a whole family’s pay, I couldn’t keep up.

Then I graduated flight school, shipped off to Korea and started getting paid as a W-1 (a few hundred bucks below O-1). Do you know what I did? Of course, you do. Isolated on a base without much to spend my money on, without the ability to drive — I bought a $15,000 Jeep — without the opportunity to travel, I spent hundreds of dollars every weekend going nowhere and doing nothing.

Money worries aside, however, these were fantastic and formative years for me. Flight school taught me what I was capable of deep-down, and how to develop an attitude that’s helped me overcome adversity the rest of my life. During these years I learned how to pay attention, how to struggle, and how to fight. I learned the importance of persevering, humility and of taking chances. I learned that life is, by and large, a game — and that some rules can be bent and some should never be doubted. Those years made me the man I am today — but I sure had a hard time controlling my wallet.

After Korea, I ended up in Germany and somehow already began to feel “old”. Korea was a 1-year duty station, so pilots just out of flight school had to work fast and hard to become a PIC (Pilot-in-Command) during their tour. And of course, the mission depends on having plenty of PICs. I was an OH-58 pilot in an Air Cavalry unit which meant (in theory) we were the focus, and the AH-1 Cobras were there to support us. I managed to become a PIC in the first 3-months and spent the rest of the year “blasting holes in the sky” as they say.

Back to Germany — a few other pilots had graduated near the time I had, but they were still flying co-pilot in a pretty slow-paced (by comparison) unit. I went out for beers with the unit’s IP (Instructor Pilot) and convinced him to test me straight-away for PIC. To my surprise, he did — and so, within weeks of arriving in Germany, I was Pilot-in-Command at my second duty-station. I was only 21. This sounds as if I’m bragging, but I’m building up to a point (I promise) — sometimes age and experience become divergent.

Getting out of debt

But as experienced as I was as a pilot or a person, I still couldn’t pay my bills. By luck, I happened into a group of guys that were seriously money-minded. These guys were trading stocks (this is pre-Web 1990, mind you). They were making plans to buy rental properties and looking at the best franchises to potentially invest in. I met one couple who invited me to their house to listen to a pitch from a financial planner who’d put them on this absolute austerity budget and invested a huge part of their pay with him. To this day, I don’t know if it was legitimate or some kind of MLM / pyramid scheme — but the influence of all these folks began to affect me.

I changed my attitude toward credit. Previously I thought, “Oh, you’re offering me credit, why yes, please! And may I have some more?” But within the year, I’d started living more frugally, paying down debt and purchasing Savings Bonds (yeah, I know, not the best investment). Then Saddam Hussein invaded Kuwait, and from the “getting-on-track-with-money” perspective — it was perfect timing. Suddenly I (quite literally) had NOTHING to spend money on, AND I was getting additional combat pay!

Attached to the 4/229th Attack Battalion, with sand horizon-to-horizon, the credit card bills melted away, the savings bonds piled up and when the Army offered early-outs at the end of the first Gulf War, I left the military 4-years into my 6-year commitment. I had $4,000 saved and $20,000 of G.I. Bill money ready to carry me back into civilian life.

Using the GI Bill

And you’ll never guess where I ended up — in my parents’ basement, driving the same old roads to the same old places, and enrolling at a local school — and absolutely loving it. The fresh air of coming home, the comfort of knowing where I was going and the almost guaranteed safety of getting there, it was satisfying in the most profound ways possible. Just driving up to a red light that I’d sat through a thousand times in my life — it felt like a gift. Then my classes started.

Fortunately, I’d earned some college credit in the military, so I started school as a sophomore. Being a freshman would have probably demoralized me, but sophomore seemed okay.

I attended Towson University, which is not exactly a “no name” school, but it was just a 15-minute drive from my childhood home. (Note: I LOVE Towson University. It’s provided incredibly valuable learning and relationships in my life. I continue to be involved both as a financial supporter and as an adjunct professor in their Computer Science department) The classes themselves, were not the problem — but remember that whole “age versus experience” thing I mentioned? Let’s just say I had problems fitting in. I was 24 when classes started, which is certainly older than the 19-20 year olds I was attending classes with — but as a former pilot, army warrant officer, and foreign war veteran — the experience gap felt massive.

I started to question my decision to attend college at all. Yes, being home felt wonderful. Regaining old friendships was a blast, and I certainly had a new appreciation for family and being connected to a particular place. But college itself, the atmosphere and social aspects — it felt like going backward, almost like a waste of time. The first couple semesters were definitely the most difficult part of my transition back to civilian life — and I nearly dropped out on more than one occasion. Then I visited my local Army Reserve unit.

My perspective shifted all over again. I entered the pilot lounge and almost immediately after striking up a conversation with some guys — I felt completely out of place. There was something about the story-telling and reminiscing, the military bravado, the tendency to verbally lift themselves up having lived (and in many cases fought) through aspects of life most Americans never have to endure — somehow that all felt behind me as well. At 24 I most certainly did not want to be staring back at my life, and I realized that if I didn’t finish up my degree and engage in some new career — then whatever I did, it would probably have me staring squarely backward.

Perseverance and resilience– from the military

Image of the logo of a Veteran Owned Small Business from the Veterans Administration

So the next 25 years passed rapidly. I finished college and began working in IT. I had a 20+ year career in all aspects of software development, and in 2014 I began to work on my own “Personal Financial Modeling” software, OnTrajectory.com. This new stage of life as “FinTech Entrepreneur” may be separated from my time in the military by many years, but not from the skills and life experiences I gained — the most important being self-confidence and self-reliance. Those were the two most critical lessons I learned, and they’re necessary for anyone going the “start-up” route.

Of course, those lessons did more than enable me to become an entrepreneur, they underpinned all of the success I’ve had in life. Knowing what’s inside you, what you’re capable of, and having the perseverance to push through any adversity — these I learned in the brief 4-years I spent in the Army. I had no idea that getting the G.I Bill would bring so much more than a college education — that it would shape who I am for the rest of my life, but there you go.

Related articles:
OnTrajectory review by Gwen (of FIery Millennials) on BudgetsAreSexy
Five Ways To Ease The Transition From The Military To A Civilian Career
Military Veterans Rate A FREE Year Of Linkedin Premium
Life After The Military:  Now What?

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The Military Guide to Financial Independence and Retirement Price: By Doug Nordman: This book provides servicemembers, veterans, and their families with a critical roadmap for becoming financially independent. The Military Guide to Financial Independence and Retirement All Author royalties donated to military charities. Last Updated: 10/10/2018



WHAT I DO: I help you reach financial independence. For free. I retired in 2002 after 20 years in the Navy's submarine force. I wrote "The Military Guide to Financial Independence and Retirement" to share the stories of over 50 other financially independent servicemembers, veterans, and families. All of my writing revenue is donated to military-friendly charities.

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