This week on the Oakley Podcast, Jeremy Kellett sits with Michael and Leslie Hopper, a husband-and-wife team at Oakley Trucking, to share their late-career transition into trucking and eventual success as owner-operators. They walk through Michael’s move from multi-unit management and daycare operations and Leslie’s 31-year restaurant career into trucking in their late 40s, starting with carriers like Werner, Tyson, U.S. Xpress, and FedEx Custom Critical before buying their own trucks and ultimately landing at Oakley. The Hoppers explain how teaming works day vs. night, how they became a top revenue truck pulling an end dump, why they’re now moving to pneumatics for longer miles and higher pay, and how trucking allowed them to buy a home, build retirement, and support a large blended family. Their key message: it’s never too late to reinvent yourself, owner-operator trucking can be a powerful path to financial freedom, and companies like Oakley can make the leap from company driver to business owner much more achievable.
Key topics in today’s conversation include:
- Welcoming the Hoppers to the Show (0:42)
- Leslie’s Restaurant Career and First Talk of Trucking (6:09)
- Michael’s Corporate and Daycare Management Background (9:17)
- How They Met, First Date, and Long-Distance Relationship (13:18)
- Convincing Leslie to Change Careers and Go to Truck School (16:44)
- Training Together at U.S. Xpress and Becoming a Team (18:23)
- Why Teaming Works for Them, Day vs Night Driving, and Resets (23:44)
- Taking the Leap to Owner Operator and Early Panic With No Loads (26:35)
- Running FedEx Custom Critical and Department of Defense Freight (29:59)
- Leaving FedEx, Short Hazmat Stop, and Choosing Oakley (33:17)
- Deadheading, Emergency Loads, and Being a Top Revenue Truck (36:27)
- Leslie’s Social Media, Oakley Community, and Dump Video Followers (41:01)
- Buying Their House on Five Acres And Building Late-Life Retirement (44:02)
- Moving From End Dump to Pneumatic and Chasing Higher Rates (47:32)
- Why It’s Not Too Late to Start Trucking at 50 and Thrive (52:39)
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.