DiscoverThe Oakley Podcast258: One Month at Oakley as an Owner-Operator: Jared’s Journey
258: One Month at Oakley as an Owner-Operator: Jared’s Journey

258: One Month at Oakley as an Owner-Operator: Jared’s Journey

Update: 2025-08-13
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This week on the Oakley Podcast, host Jeremy Kellett chats with Jared Smith, one of our new owner/operators at Oakley. Jared talks about his first month at Oakley Trucking, sharing his journey from company driver to independent contractor. He discusses the challenges of making the leap, the importance of family and faith, and the support he’s received from Oakley’s team. The conversation covers orientation, adapting to new technology, financial planning, and the value of a strong support system both at home and on the road. Key takeaways include the importance of taking risks, building a solid foundation for your family, the benefits of joining a company that values its drivers and fosters a supportive community, and so much more.

Key topics in today’s conversation include:

  • Meet Jared Smith: Background and Family (3:07 )
  • Jared’s Path to Oakley (4:30 )
  • Career History: Firefighting and Oilfield Work (6:07 )
  • Transition to Owner-Operator (9:41 )
  • First Month at Oakley: Orientation and Training (14:07 )
  • On-the-Job Training and Field Support (15:42 )
  • Toughest Challenges on the Road (18:53 )
  • Explaining Trucking to the Public: ELDs and Safety (21:13 )
  • Oakley vs. Other Trucking Companies (25:47 )
  • Learning Finances as an Owner-Operator (26:19 )
  • Health, Food, and Staying Active as a Driver (29:11 )
  • Jared’s Goals for the Future (32:12 )
  • Final Thoughts and Takeaways (36:59 )

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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258: One Month at Oakley as an Owner-Operator: Jared’s Journey

258: One Month at Oakley as an Owner-Operator: Jared’s Journey

Oakley Trucking