Jack Esper:
Independent Instructor Commercial Pilot
Thank you for coming to my website! This is the place where I can share a bit more of who I am, what inspired me to fly, and what I can offer to help you achieve your mission! Scroll down to learn more!
Check out my portfolio with photos I have captured from some of my many adventures in the sky!
About Jack



Jack first took to the skies with a discovery flight in 2021 at home in Colorado, and quickly knew aviation was going to be his passion. He chose to fly at Southeastern University in Lakeland Florda, where he earned a Bachelor of Science in Aviation Management in three years. This program allowed him to achieve his Private and IFR ratings in 2022, followed by Commercial in 2023, and CFI in 2024 when he graduated. On top of those ratings, Jack received his CFII at the end of 2024, and both his Multi-engine add on and tailwheel endorsement in 2025.
When Jack received his Commercial in 2023, he was given the opportunity with Northwoods Air to fly a summer aerial survey contract in Indiana. This is where Jack's aviation experience really started, as he was given sole responsibility of both flying and maintaining an airplane on his own. This led to some fun experiences as well as good learning lessons.
After Jack graduated from SEU, he was hired by Northwoods as a CFI. He moved from Florida all the way up to Old Town Maine, where he was given the responsibility of helping run and manage a flight school from the ground up. Jack did this for a year, and grew the Maine flying community by helping manage operations at the airport and provided training to those who wanted to fly!
Both of these experiences have sharpened Jack's ability and knowledge as a Commercial pilot and an Instructor. Between aerial survey and flight instruction, Jack has flown in over 10 states with ferry operations and survey work, has over 500 hours of dual given with various students and airframes, and has helped over 5 student pilots pass their checkrides! On top of that, Jack has experience with all four weather seasons and different climates of terrain, including plenty of mountain and wintertime flying thanks in Maine.
Jack's Services
Currently Jack is based out of the Denver metro area in Colorado, but is flexible and able to travel if you are located elsewhere
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If you are interested in learning more and have questions about rates, scheduling, or about any of the services that Jack provides, please contact Jack with the form below!
Flight Instruction
Learning to Fly
With plenty of experience as a CFI, Jack would love to help you achieve your goals! Whether its starting at 0 hours or finishing up your training, Jack has experience in both sectors and can help you cross the finish line!
Currency and Endorsements
Whether you need a Flight Review/Instrument Proficiency Check, or High Performance/Complex/Tailwheel endorsement, Jack can sign you off and will give you the proper training if needed!
Pilot Operations
Ferry Flights
Depending on the aircraft and situation, Jack can help you move your aircraft wherever it needs to go. Whether its a relocation or a new aircraft buyer, Jack has the experience with the National Airspace system to get your plane from A to B.
Safety Pilot and Second in Command
With a background flying different operations in both Single and Multi engine aircraft, Jack can be a second set of eyes if you are looking for an experienced option for a safety pilot or an SIC.
Custom Options
If you need any specific training or have a specific operation of flying, be sure to contact Jack and he can work with you on what you are looking for!


