our story

Ryan J. Fleming, MBA, RICP, CRPC is “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 want to change their life!

I was born in central Ohio where the first thing they do is give you a football in the hospital crib, just to ensure there is no confusion about what college football team you will be rooting for. We lived on the outskirts of town in those early years, and I remember my father being on the road a lot working various construction projects to make ends meet.

My mother took care of my older sister, Ashlee, and I and a few cousins who lived down the street. We spent most of our time playing outside, building forts in the woods and walking up and down the small streams near our house that we referred to as “creekin” later in life.

When I was in first grade, my dad landed a job that got him off the construction projects and we moved away from all my family, venturing south to Cincinnati. He sold plumbing supplies, and this was going to be our new break in life. My parents got a house in a nicer neighborhood that we could hardly afford, and my mom started cleaning houses around town for the more fortunate. It was tough paying the bills, but they were adamant about keeping us in this school district so we could have the opportunity to get a great education.

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.