Kris Sharpe - The Flying Entrepreneur
Interviewed by Steve Gillman
Kris Sharpe has had an interest in aviation and business for
most of his life. He first put the two together at the age of
eight, selling paper airplanes. Now, at just thirty years old,
with years of experience as a pilot and flight instructor, he
is again tying together his two interests. Naturally I wanted
to ask him about his newly-launched company, WingmanTF, but I
had to start his story with that first business he launched at
eight years old.
I understand that you made some
top-notch paper airplanes as a child, and that you not only sold
them to other kids in school, but even had an employee or two.
Can you tell us about that?
I have to chuckle and smile at that. Yeah, they are top notch
paper airplanes and gliders. I was in the 4th grade and noticed
that everyone wanted me to make paper planes or gliders for them.
So, I did. Well in grade school if you can remember, your parents
or guardians will only let you have so much paper for school.
I thought to myself, I should be getting paid for the use of
my paper to make these paper planes. So, I began to charge for
the service rendered. I was charging anywhere from 5 cents to
25 cents per the quality of the plane. I was still using my paper
at first. Then I capped it at certain point so I would still
have paper for school. I told anyone that wanted a paper airplane
or glider made they would have to supply the paper and the cash.
Believe it or not I got busier. I started doing the same thing
at my daycare. I was making anywhere from $10.00 to $20.00 a
week. I hired a few employees to keep up with the demand. A month
to month in a half into I was shut down. Complaints from parents
started to come in about their children having no lunch money.
Granted I did buy desserts and drinks for students to subsidize
the earnings. I had some explaining to do. Surprisingly I didn't
get into as much trouble as I thought I was going to. I was told
to give the money back. I simply explained that I had no receipts
and did not track who bought what. Then it was dropped. I was
told not to sell anything at school again. It was my first business.
I learned a lot from the experience.
Was that early interest in aviation
sustained through childhood, or is it something you rediscovered
I discovered aviation on my first flight at the age of two.
I was hooked. All I ever talked about was flying. I feel that
you will always rediscover your passions in new ways. Growing
up flying was always in the back of my head, but I was too young
to do anything about it. In high school I was able to accomplish
my goal of completing my private pilot license. I got a job working
at a hospital thanks to my basketball coach. It would be the
way I paid for my lessons. I had to work for it but it was well
You clearly demonstrated an entrepreneurial
spirit with your paper airplane business, so did you try other
ways to make money at an early age?
Thanks and yes. I would work around the house. Do yard work.
Shovel snow. What most kids would do.
How old were you when you first
got a pilot's license and first became a flight instructor?
I was 17 when I achieved my private pilot license. I was 22
when I received my flight instructor's certificate.
Was teaching people to fly something
that you enjoyed or just a way to pay the bills?
If you have ever been in the aviation game you could agree
that it's both. Most everyone I have met in my career of aviation
really truly enjoys it as I do. I have had the pleasure of meeting
great students. Facing the facts though, aviation is all about
getting your flight time if you want to get to the next level.
Flight instruction is good for building time and for working
on your communication skills. Flight instruction doesn't really
start as just a way to pay the bills but it can definitely turn
into it. So many variables can affect if you will be getting
an ok paycheck or not, but that is the game.
Now, your current venture is all
about clothing and accessories. How did you decide to get into
Yes, my current business, WingmanTF, is starting out with
clothing and accessories. I wanted to be able to share my passion
for aviation. I decided to start this business back in 2010.
It started out as joke. Then I started to really think on it.
I said why not. Like any venture there is the reality phase.
My friends pretty much thought I had lost it even though they
were trying to be supportive. I just said this makes me happy
and I'm going to do it. It hasn't been an easy road but you can
expect that when paying for a business out of pocket. A big factor
of passion has to be in any venture. If there is no passion for
the long run it will die.
Will all of your products have
an aviation theme, or do you plan to sell other types of clothing
I guess you could say every product will have some sort of
aviation theme. Now these products are not just tailored for
those just in aviation. I wanted to give WingmanTF a name we
all knew. There is a fun side to aviation. So, I thought the
wingman angle would be a great one. The difference would be I
have made a living in aviation which could compliment the WingmanTF
Finally, clothing is a tough market,
and doing something different is often required for success,
so what makes your products unique?
You said it. Clothing is a big market. I think it's all about
having a niche. There's nothing new under the sun. I wish I could
tell you I'm doing something different or I had the master plan.
Just like with flying things can change in a hurry. So, being
able handle the movement is key. In today's business world it's
hard to tell what will work and what will not. You just have
to be willing to try and see where it takes you.
Kris Sharpe lives in Naples, Florida at the moment, but operates
his business from wherever he finds himself.