20 Under 40 Class of 2024: Garrett Fleishman

20 Under 40 Class of 2024: Garrett Fleishman

I’ve always had an interest in vintage aircraft and warbirds. I started by building and flying large scale RC airplanes at my local RC club, the Quaker Farms RC Flyers, in my early teens. By the time I turned 16 I had a job at my local airport KOXC as an airplane washer for Tradewind Aviation, a part 135 operator that flys Pilatus PC-12’s and Citation CJ3’s.

While working for Tradewind I started flight training with the Oxford Flying Club. I waited for them to acquire a Cessna 170, soloed at 16 and earned my Private on my 17th birthday.

My mentor Nick Tramantano had a Twin Beech and a T6 Texan. I was very fortunate to be able to build time with him in the Beech early in my aviation career. I also spent a lot of time volunteering to keep a C47, Placid Lassie, flying and became a Board Member of the Tunison Foundation that operates it. I earned a DC3 SIC type rating soon after I had my Multi, and become a PIC with about 120 hours of SIC time in the DC3.

I had my private and a few hundred hours in mostly tailwheel aircraft before I went off to college. I graduated in 2020 with a bachelors degree in unmanned aircraft systems as well as my instrument through CFI from Embry Riddle Aeronautical University. During my free time I started skydiving and became the President of the Embry Riddle Skydiving Club.

To build experience, I worked many different jobs at Tradewind Aviation. I started as an airplane washer and quickly became a Maintenance Assistant then spent season as an Aircraft Dispatcher. I started flying full time for Tradewind in the PC-12 in 2020 after getting back from College.

I purchased my first airplane in November of last year, a 1941 Boeing Stearman project out of Dallas TX. I drove my new airplane home behind my truck all of the way to Connecticut and have been putting it together with my friends since. I test flew the airplane a few weeks ago and only have a few squawks to address before the airplane is complete and I start sharing my beautiful new biplane with others.

I have about 40 different aircraft types logged and warbirds are truly my passion. I earned a FAST Formation card through the North American Trainers Association and started flying in airshows in the C47, Twin Beech, and T6 a few years ago. I have an LOA to fly the TBM Avenger and hoping my next type rating is in the aircraft.

I now hold an ATP, CFI, DC3 and CE525 PIC type ratings, as well as a dispatch certificate. To fund my warbird addiction I am currently a Check Airmen, Instructor, CJ3, and PC-12 pilot for Tradewind Aviation.

I’m extremely excited to see where my Aviation Career takes me and I would not be where I am today without the support of all of my friends, family, and mentors. It is my goal to give back to the aviation community by sharing my passion with as many people that I can and never take an interesting airplane flying without an empty seat.