Glenn Allyn was born and raised in New York, where his interest in leadership and complex systems began to form early. He pursued higher education at Hartwick College in Oneonta, earning a Bachelor of Arts in Management. His academic path continued in New York City, where he obtained a Juris Doctor degree from the Benjamin N. Cardozo School of Law. These qualifications became the base for a multi-industry career that integrated legal knowledge, aviation, and real estate.
After law school, Glenn worked at several respected legal firms in New York City and White Plains. He advanced to become a partner in two firms and focused his practice on aviation law and ski-related liability. Early in his legal work, he was involved in major international airline cases related to aircraft crashes, which deepened his understanding of reinsurance and transportation risk. This work led to a lasting connection between his legal skills and his future in aviation.
Glenn B Allyn's legal work overlapped with personal interest when he began working on ski industry liability cases. At the same time, he coached young ski athletes between the ages of 12 and 15. He had previously served as a ski instructor and staff trainer at a mountain resort, teaching both instructors and students. His role as a J3/J4 coach required him to develop technical skiing skills, guide race strategies, build confidence among young competitors, and emphasize safety and discipline on the slopes.
Before entering law, he started his professional life in the automotive sector. He worked as a sales manager at a Nyack, New York dealership. This initial experience introduced him to business operations, client interaction, and performance accountability—skills he would carry into every role thereafter.
Over 15 years, Glenn Allyn also built a parallel career in real estate. His work spanned residential and commercial development, property management, and tenant services. His responsibilities included managing renovations, overseeing leases, and coordinating construction. This experience gave him practical knowledge of large-scale asset management and long-term business planning.
His passion for aviation took professional form when he joined Northeast Jet in Allentown, Pennsylvania, as a Learjet captain. Later, he became Director of Operations at Tab Aviation, which operated in New Hampshire and New York. These roles gave him insight into flight safety, regulatory standards, and management practices required in private aviation.
In addition to flight operations, Glenn expanded his aviation expertise in sales. At Best Jets, Inc., he served as a broker and sales associate, arranging deals involving jets, helicopters, turboprops, and other aircraft. He guided buyers and sellers through all transaction stages, ensuring each sale met legal and mechanical standards while delivering reliable client service.
As Chief Pilot for M’Air Aviation, he supervised pilots, managed risks, and participated in sales processes. His leadership included responsibility for operational planning, customer service, and compliance with flight regulations. These experiences set the stage for the launch of his own aviation business, combining technical insight with entrepreneurial drive.
He has operated Flying Zebra, a private aviation company based at Westchester County Airport in New York, for over seven years. The company provides chartered flights throughout the U.S., Canada, the Caribbean, and the Bahamas. Its fleet includes Pilatus PC-12 models known for performance and safety. Under his direction, the company emphasizes reliability, customer support, and a strong safety record.
Glenn’s responsibilities at Flying Zebra are extensive. They include pilot training coordination, maintenance oversight, sales and charter scheduling, aircraft tracking, and risk management. He also handles warranty management, insurance compliance, aircraft leasing, and documentation. His knowledge includes tax matters related to aviation, such as deductions and ownership implications.
He has accumulated over 30,000 hours of flight time, including more than 22,000 hours as a lead pilot. His experience spans multiple aircraft types, including jets, turboprops, and helicopters. With 1,600 hours logged in helicopters, he has operated in routine and challenging flight conditions. He holds FAA Part 135 certification, authorizing him to conduct charter flights and commercial on-demand operations.
Glenn Allyn has developed numerous aviation documents, such as commuter applications, Canadian operational certifications, emergency and safety manuals, and HZMAT plans. His expertise in these areas ensures that his operations remain compliant and prepared for varied scenarios.
His company focuses on destinations that commercial airlines do not serve. This model allows clients to reach remote or high-end locations with flexibility and convenience. His operational approach is grounded in safety, discretion, and efficiency, and he continues to guide the company toward adapting to client needs and evolving industry standards.
Outside of aviation and business, Glenn maintains an active lifestyle with interests in golf, cycling, biathlon, kiteboarding, and photography. He has a background in skiing competitions, including amateur and professional events, participating in disciplines like aerials and moguls. He also enjoys scuba diving, waterskiing, running, motorcycling, and competitive shooting.
Glenn Allyn remains committed to aviation and business leadership, drawing from decades of cross-sector experience. Through Flying Zebra, he continues to lead flight operations and client services with focus and care, backed by a deep knowledge of flight safety, legal compliance, and customer priorities.