DiscoverThe Oakley Podcast260: Farming Roots to Trucking Routes: Rick’s Journey to Oakley Trucking
260: Farming Roots to Trucking Routes: Rick’s Journey to Oakley Trucking

260: Farming Roots to Trucking Routes: Rick’s Journey to Oakley Trucking

Update: 2025-08-27
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This week on the Oakley Podcast, Jeremy and Megan sit down with Rick Rupe, one of our owner/operators at Oakley. Rick shares his journey from farming to trucking, the importance of family support, and the realities of life on the road. Rick shares insights on balancing farm and trucking responsibilities, the decision-making process behind becoming an owner-operator, and practical advice for those considering the leap. The conversation also addresses common misconceptions about truck drivers and emphasizes the value of perseverance, adaptability, and community in the trucking industry. Key takeaways include the importance of doing your homework before buying a truck, maintaining a healthy work-life balance, and staying open to new opportunities.

Key topics in today’s conversation include:

  • Episode Preview & Welcoming Megan Back (0:51 )
  • Rick Rupe’s Owner/Operator Story (4:16 )
  • Farming Background and Entry into Trucking (6:44 )
  • Transition from Chicken Farming to Trucking (10:10 )
  • Decision Process to Join Oakley (14:13 )
  • Gaining Confidence to Become Owner-Operator (16:20 )
  • Upgrading Trucks and Changing Divisions (20:21 )
  • Learning the Plastics Division (23:35 )
  • Myths About Truck Drivers (24:44 )
  • Advice for Aspiring Owner-Operators (30:33 )
  • Financial Realities and Family Support (33:50 )
  • Final Thoughts and Takeaways (34:20 )

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.


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260: Farming Roots to Trucking Routes: Rick’s Journey to Oakley Trucking

260: Farming Roots to Trucking Routes: Rick’s Journey to Oakley Trucking

Oakley Trucking