From Cockpit to Compliance: Ryan DeMoor's Journey

From Cockpit to Compliance: Ryan DeMoor's Journey

From The Cross-Check by The Frequency Network: The Wave

October 15, 2025 · 36 min

About this episode

Ryan DeMoor shares his journey from commercial pilot to aviation tax and finance expert, discussing the challenges and innovations in the field.

Is there a disconnect between your flight department, payroll and tax reporting? Sometimes it takes a unicorn like Ryan DeMoor to create system to tie it all together. Ryan shares his journey from being a commercial pilot to transitioning into the aviation tax and finance sector. He discusses the impact of 9/11 on his career, the importance of bridging the gap between finance and aviation, and the innovative solutions being developed at MySky to address tax compliance in at Part 91 and 135 operations. Ryan emphasizes the need for effective communication within flight departments and the importance of engaging the next generation in aviation tax roles. He also outlines future directions for MySky and the ongoing challenges in the aviation tax landscape. Chapters: 00:00 From Pilot to Professional: The Journey Begins 02:14 Navigating Career Changes: The Impact of 9/11 04:11 Bridging Two Worlds: Aviation and Finance 06:24 The Evolution of MySky: From Auditing to Software 08:34 Tax Compliance Challenges in Aviation 10:42 Misconceptions in Aviation Taxation 13:06 The Role of MySky in Flight Classification 15:15 Leadership in Aviation Tax: A Unique Perspective 17:42 Engaging Young…

People in this episode

Guest: Ryan DeMoor

Topics covered

  • aviation tax
  • finance
  • career transition
  • compliance
  • communication
  • future of aviation

Keywords

  • aviation
  • tax compliance
  • finance
  • career changes
  • MySky
  • 9/11 impact
  • communication

Mentioned in this episode

Organizations: MySky

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