Catching Up With Greg Windmiller


Canopy pilot extraordinaire Greg Windmiller has been a busy man making big changes over the past year. One of these was his ‘retirement’ from the Golden Knights and the subsequent creation of his own business Superior Flight Solutions. Here we catch up with him to learn about his transition from the military to being a business owner and operator.

What was your life like when you were a part of the Golden Knights and how is your life different now that you have ‘retired’?

I was coaching so regularly on the weekends while I was in the Army that it made it an easy transition into civilian life. [And] Life, for me, isn’t much different than when I was in the Army, but it is quite a bit busier.

While on the Golden Knights, my job during the week was to research and develop new techniques and procedures and figure out how to win. It was also to train for national and international competitions. Simply put, my job was to win medals and set records. During the weekends, when I wasn’t competing, I would book canopy courses all over the east coast. I would travel from Miami all the way to Maine because the east coast was easy to travel to. I would take a red-eye out Friday and the red-eye back Sunday if I had to fly. I never had to advertise my courses, and I didn’t need to because my courses were always full.

Photo by Joe Abeln

Photo by Joe Abeln

Young in my skydiving career, I was fortunate enough to have some very good coaches. I got coaching from a lot of different people at the highest levels. From 4 way coaching with Arizona Airspeed and Pete Allum to canopy coaching with National and World Champions in Accuracy, CRW and Canopy Piloting. I would always seek out the best, and when they talked, I would not only listen to what they said but I would also listen to how they said it. I watched and listened to their mannerisms, their attitudes, and their energy. I remembered the best instructors not by what they said but by how they related it and relayed it. I wanted to be a professional coach. I strived to be the coach that could explain everything to everyone. When coaching, I focus more on the person than the situation. My goal is for every single person to leave my courses feeling as though they were the only ones in the course. As if it was a one on one course. To me, it’s more important what is going on in the head of the person while they are under canopy than what they are doing while under canopy.

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Do you miss being part of the Golden Knights?

I miss being on the Golden Knights. I miss the camaraderie of being on the team, but honestly, once you are on the team, you are always a teammate. I just don’t have to get up early during the week and do those dumb mandatory online classes once a month.

Hanging with a couple of civilians (Melanie Curtis and James La Barrie at the 2017 PIA Symposium. Photo by Melanie Curtis

Hanging with a couple of civilians (Melanie Curtis and James La Barrie at the 2017 PIA Symposium. Photo by Melanie Curtis

Additionally when you began coaching (while still a part of the Golden Knights/ Military) did you see it progressing the way that it has? Did you think you would make a career out of coaching?

I started coaching around 2002 while I was on the team. I coached accuracy and basic courses teaching what I learned

Photo provided by Greg Windmiller

Photo provided by Greg Windmiller

from my coaches while I was the team leader of the Golden Knights Accuracy team. It wasn’t until 2009 that I started coaching high-performance canopy piloting.

I didn’t even jump a crossbraced canopy myself until I had 6,000 jumps. Around 2013, I knew this was something that I could make into a career. I knew it was something that I wanted to keep doing. The success of my students speaks for itself. Since 2011, 80% of the medal winners in the advanced division of canopy piloting at the USPA Nationals have been my students. That is something I am extremely proud of.

What sort of challenges were there to get Superior Flight Solutions off the ground? Did your military career prepare you to face these challenges?

The only challenges getting Superior Flight Solutions off the ground was branding. While in the Army, it was always “Greg Windmiller’s Canopy Courses.” When I retired, I started advertising under my company’s name, but people didn’t know Superior Flight Solutions.  I had a DZ advertise my companies name for a course once. It was advertised for 2 weeks. No one signed up. They begged and begged to use my name. Finally, I agreed and said okay. The course sold out in 4 hours. 12 slots per day for 3 days straight. After the course sold out, I had them change it back to my company’s name. 4 people backed out within the hour.

My career in the military prepared me for what would be my biggest challenges. The personalities, the unpredictability of skydivers and the occasional lunatic who tries to hurt themselves. My biggest pet peeves in the sport and in coaching are people not being courteous towards others.  In the courses, it is people showing up late for courses. Yeah, it may be you showing up late, but in the end, it’s actually you taking a jump away from 11 other people that came to learn and that had the courtesy to show up on time.

Since you started this business it has really expanded and now you have Matt Leonard working for you. How is business going? What does he visualize for the long term?

In the last year, the business has expanded so much with military contracts that I have hired one of my long-time students and the 2015 advanced US National canopy piloting champion, Matt Leonard. I can’t say enough good things about Matt. He is smart, energetic and talented. We talked about expanding a while ago, but letting go of liability and letting go of something I built is something that I didn’t take lightly.

This blog proudly supported by Burble Software.

This blog proudly supported by Burble Software.

After long deliberation, I asked Matt to join me. He followed me and watched me coach several courses. We sat together for over a week and a half and went over videos for hours and hours, coaching techniques, and etiquette. Matt has his own technique of teaching, and that is something that I believe to be extremely important and something that I love about him. It’s a fresh way of looking with new eyes at the program that I developed. Matt has great ideas about expanding the company, and I greet them with open arms.

Finally, what are you most passionate about with skydiving today? What keeps that passion burning?

My passion lies in the students and teaching. I feed off of the energy of my students and it motivates me. I love seeing the proverbial lightbulb go on and their eyes light up when they get it. Now, I get to hand some of that off to Matt while I focus on my military contracts.

My military contracts have taken off and that is what I was hoping for. I wanted to give military units an option. Before, there were only a few organizations coaching military units in free fall and canopy progression, and the organizations coaching them had no military background themselves. They had actually never done what they were teaching. Before I joined the Golden Knights, I was on a Military Free Fall team. I served seven years in a small specialty unit, and we used military free fall as a method of insertion. I was also an instructor for 4 years after that which taught soldiers how to do what I did. My background prepared me to coach military units. I had actually walked the walk and now it was time to give back.


I designed military program years ago that I have been waiting to present. Once I retired, I got that chance. After I ran the first course, word got out, and now it is non-stop, and I love it.  To me, it’s not about the money. It’s about giving back to the soldiers what I learned while I was a soldier. I make every course, military or civilian, personal. I treat every student as though they are my only student. I want to make every single skydiver in the world a safer skydiver and the only way to do that is to make them smarter.

About James La Barrie

James La Barrie is passionate about marketing and changing a company's service culture. Originally from the Caribbean island of Antigua, James melds his approach of marketing and delivering elite service together as one. James has injected his 'service marketing' approach throughout his career to transform companies from good to great.

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