Welcome back to The Road Show with Tony Justice and Friends! We’re kicking off the second half of our 2025 season with a bang. In this episode, I sit down with Jeremy Kellett from Oakley Trucking. Jeremy and I go way back, and he recently had me on The Oakley Podcast – so it only made sense to bring him on my show to return the favor and dive into a great conversation. We talk trucking from the unique lens of a company deeply rooted in tradition, innovation, and genuine care for its drivers. If you’re in the industry or just curious about the heartbeat behind America’s freight movement, this one’s for you.

We explore everything from the generational legacy of Oakley Trucking to the everyday challenges and triumphs of owner-operators. Jeremy shares valuable insights into driver retention, the pitfalls of overregulation, and how Oakley stays ahead of the curve with honest recruiting, realistic expectations, and a family-oriented culture. Whether you're an aspiring driver, seasoned hauler, or trucking enthusiast, this episode is packed with lessons and laughs you won't want to miss.

Topics Discussed in the Episode

• Jeremy shares the 57-year history of Oakley Trucking and its generational leadership

• The critical difference between recruiting and retention in the trucking world

• How Oakley Trucking vets and supports its drivers from day one

• Why driver appreciation and honest communication matter

• How Jeremy would tackle overregulation in the trucking industry

• The impact of The Oakley Podcast and how it's fostering stronger driver connections

Links & Resources

• The Oakley Podcast: https://podcasts.apple.com/us/podcast/the-oakley-podcast/id1500924861