Kris Sharpe - The Flying Entrepreneur

Interviewed by

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 later?

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 worth it.

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 that business?

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 and accessories?

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 theme.

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.

If you liked this page please let others know with one of these...

Other Relevant Pages

Fun and Interesting Jobs

Good Businesses

Interviews with People Making Money


(The newsletter has been discontinued.)

Every Way to Make Money | Flying Entrepreneur