The Oakley Podcast: From the Archives – Open Skies to Open Roads: A Pilot’s Unique Journey From Flying to Trucking

We’re taking a look back at some of our favorite episodes of 2025. This week on the Oakley Podcast, hosts Jeremy Kellett and Megan Cummings welcome Brad Page, one of our owner/operators at Oakley Trucking. During the episode, Brad shares his incredible journey as a commercial airline pilot for over 30 years to the open road of being an owner-operator. The discussion covers Brad’s memorable flying experiences, including challenging landings and his work in medevac missions. The episode also touches on Brad’s family, his sons’ careers in engineering and mechanics, the evolving technology in the trucking industry, comparisons between being a pilot and an owner-operator, and so much more.

Key topics in today’s conversation include:

  • Previewing the Upcoming Episode (1:14)
  • Changes in the Office (6:31)
  • Megan’s New Role (7:30)
  • Listener Interaction Segment (9:29)
  • Brad’s Background and Aviation Career (13:35)
  • Medevac Job Explanation (17:12)
  • Becoming a Pilot (18:57)
  • Commuter Airline Job (22:17)
  • Challenges of Airline Piloting (25:32)
  • Air Conditioning on Planes (34:31)
  • Landing in Windy Conditions (37:05)
  • Transition from Aviation to Trucking (39:01)
  • Consulting Work Post-Retirement (42:03)
  • Joining Oakley Trucking (46:55)
  • Learning the Ropes at Oakley (51:09)
  • Making Pilot Announcements (58:03)
  • Technology in Trucking (59:18)
  • Final Thoughts and Takeaways (1:01:04)

Oakley Trucking is a family-owned and operated trucking company headquartered in North Little Rock, Arkansas. For more information, check out our show website: podcast.bruceoakley.com.