283: Why Three Owner-Operators in ONE Family Chose Oakley Trucking

This week on the Oakley Podcast, host Jeremy Kellett chats with Jerald, Meka, and Jermari Hogan, a husband, wife, and son trio who are all Owner/Operators at Oakley Trucking. They walk through Jerald’s 30-year journey from military heavy-equipment hauling to Oakley, how he intentionally built a path to buy trucks for his wife and son, and how Meka and Jermari each transitioned from other jobs (postal work, welding, hot shot, TransAm) into successful trucking careers. The family shares hard-learned lessons on safety, protecting your CDL, managing business numbers versus “looking good,” working with dispatch, and navigating marriage and family when everyone’s in a truck. Key takeaways: trucking can be a true family business, strong planning and discipline beat shiny equipment, Oakley’s freight and support make ownership more attainable, and trades like trucking can out-earn many college paths when treated like a real business. Don’t miss this great episode!

Key topics in today’s conversation include:

  • Welcome to Today’s Episode with the Hogans (0:36)
  • Jerald’s Oakley Story and 30 Years in Trucking (3:35)
  • Jerald and Meka’s Long Relationship and Marriage Background (7:27)
  • How Meka Got Talked into Driving and Her Early Trucking Struggles (10:52)
  • Buying Meka’s Truck, Covid Pricing, and the Business Plan for the Family (14:53)
  • Jermari’s Career Search, Welding Job, and Decision to Get His CDL (18:38)
  • Hot Shot Hauling, Learning Ownership, and Laying the Path to Oakley (22:12)
  • Younger Drivers Getting into Trucking (26:25)
  • Safety, Sharing the Road, and What the Public Needs to Know About Trucks (30:02)
  • Relationships with Dispatchers and Oakley’s View of the Hogan Family (33:42)
  • Future Plans, CDL Versus College, and Final Thoughts (37:46)

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.