As soon as I was big enough to start pushing a lawnmower, I started a business cutting grass. That job, combined with my newspaper route, made me feel like I was earning good money; enough to help out around the house and to buy some sports equipment as I started having an interest in all sports.

Although we never went without eating, we lived paycheck to paycheck and were definitely the least fortunate in our town. I decided back then that I was going to work very hard in school so that I would never need to live like that when I grew up. My interest in personal finance, therefore, started early in life.

I excelled in sports and upon graduation, I was being offered football scholarships by many schools in the Big Ten and also the MAC.

I knew nothing about the Air Force Academy in Colorado Springs, but after Fisher Deberry, Air Force’s Hall of Fame football Head Coach, showed up at a few of my basketball practices, I agreed to take a visit to Colorado to check it out. Something about it was different and it was one of top educations I could get in the whole country.

I graduated with a 3.94, so USAFA was very interested in me. Thankfully, I was being very analytical with my decisions back then because I came home and told my parents that I was going to attend the Air Force Academy, and to this day, I would say that was the single best decision of my life.

The Academy presented a very difficult life and everyone there was extremely intelligent. It was challenging and I met some of the most amazing people there, many of whom became lifelong friends.

I did pretty well in football there, breaking many of the records for wide receivers, and upon graduation, my leadership was trying to figure out a way I could get released from my Air Force commitment so I could play in the NFL.

While they worked on that, I had to give up my pilot training slot because they weren’t going to spend millions of dollars on training me to be a pilot so that I could go and play football.

The Secretary of the Air Force eventually said no to this request and playing in the Blue vs Gray All-Star game was the last time I engaged with the sport. I graduated from USAFA with a degree in Business Management in 2001.

After not being released from my active-duty commitment, I served as an Acquisition and Procurement Officer in the United States Air Force. I led a team that negotiated, managed and administered large multi-million-dollar government contracts in the Special Operations world.

I never was totally interested in the military or flying airplanes, but I figured I had the opportunity to try it and I shouldn’t pass that up, so I fought to regain my pilot training slot.  I still continued to improve myself during this time period and while doing my contracting job, I earned my MBA from the University of Arkansas with a specialization in Human Resource Management.

After a few arduous years of convincing the Air Force that they should send me back to fly, I was selected to attend flight school, and after receiving my wings as an Air Force Pilot, I eventually served multiple tours of duty in Iraq and Afghanistan, flying the mighty C­17A in direct support of the War on Terror.

I loved flying and I love being a part of a crew, but my passion for personal finance never went away. I did quite a bit of self-study courses and reading in the field, but outside of my formal finance classes at the Academy and in accomplishing my MBA, I had no formal education in the field.

I watched many of my buddies make horrible financial decisions as young officers in the Air Force and although I helped many of them, I knew there was a void to be filled.

“I’ve found that in life, everything happens for a reason, despite our best intentions and plans. So, let me tell you how I became a financial advisor…”

I was living in Destin, Florida, and I ran into a girl named Kari. I actually knew her before as she was a gorgeous soccer player at the United States Air Force Academy. She was two years younger, but all the guys knew who she was. Kari was extremely intelligent, independent and a very positive person who everyone wanted to be around. I must be very persuasive because I eventually convinced her to marry me and we have been happily married for the past 15 years.

Kari has a great family and eventually, I met her uncle who had been a financial advisor for over 30 years at the time. I would always ask him questions and was constantly picking his brain about this concept or his feelings on that fund. Finally, he convinced me that I would be really great as a financial advisor and he sponsored me to become part of his firm. I studied for months for the financial services version of the “Bar” exam, the Series 7 and the Series 66. The passage rate on these tests was barely 50% and I wanted to make sure I was on the right side of those statistics.  Thankfully, I passed both on my first attempt and I left active military service.  Then I entered the financial services industry as a Registered Representative for Cantella & Company, a SEC registered Broker/Dealer, located in the financial district of Boston.

After building my practice for a few years, I learned so much more about the business and knew the best thing for my clients and their future was to start my own firm and become a fiduciary.

As a fiduciary, I would be legally obligated to act in my client’s best interest at all times and I would no longer need to deal with the products that the broker dealer was pushing. I studied so many very successful financial advisors, but I wasn’t convinced they were truly doing what was best for their clients.  I was going to change that. In 2009, the Fleming Financial Group, LLC was founded.  I now had my own RIA.

Over the years, I earned a few more certifications and became a trusted name and advisor for the military community and fellow commercial pilots.  This is how I eventually became known as the “Pilot’s Advisor.”

I take great pride in helping my fellow aviators invest their money in a responsible and prudent manner. I don’t want to just manage their money, instead, I want to educate and teach them to stop speculating and gambling with their money. I teach them about how to use Nobel Prize winning research and academics to make investment decisions versus trying to predict the future. I teach them how to find true investment peace of mind so that they can sleep at night. I teach them how to “own and trust” a long-term investment philosophy.

My firm has grown considerably over the years and I look forward to one day running it with my wife Kari when she leaves active military service.  She is currently a Commander of a C-17 Squadron at Charleston Air Force base where we currently reside with our two children, Jaden and Race, and our yellow lab, Chuck.