Jack O’Leary | Staff Flight Instructor








Certificates and Ratings: CFI

Jack was a Minnesota kid who wanted to live in California. He enjoyed teaching from a young age and gravitated to roles like sailing instructor and design adviser. After graduating from the University of Minnesota, he took a tech job in the Bay and fell in love with the area.

Jack’s interest in flying came from hearing his grandfather’s aviation stories and flying in a seaplane around Minnesota. His first demo flight was over the lakes near Minneapolis, and he started taking flying lessons after moving to the Bay. After a few years of flying in California and the midwest, he realized that he could combine his love for aviation with his passion for teaching by becoming a full-time flight instructor.  

Jack is an avid fan of flight simulators and enjoys virtual flights as a way to meet aviation enthusiasts around the world. When he’s not flying, you can find him hiking with his wife and dog or playing board games with friends.

Aircraft Flown

  • Cessna 152, 172, 182 (N9894E)
  • Piper Archer

Ratings Offered

  • Private Pilot
  • Commercial
Other Training Offered
  • Mountain Checkout

Rate: $85/hour ($100/hour for non-members)