The Oakley Podcast

TRUCKING • BUSINESS • FAMILY

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About The Show

The Oakley Podcast is a trucking industry podcast that educates and empowers owner-operators by providing relevant industry, market, and company news in a digestible audio format.

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Podcast Episodes

251: More Than Just Loads: The Oakley Trucking Approach

June 18, 2025

This week on the Oakley Podcast, host Jeremy Kellett chats with Jason Webb & Bradley Simpson, Operations Managers at Oakley Trucking. During the conversation, the group provides an insider’s view of managing bulk freight across pneumatic and end dump divisions. They discuss the challenges of coordinating over 900 owner operators, emphasizing the critical importance of communication, customer service, and building strong relationships. With over 1,000 customers and opportunities for growth, the podcast highlights how Oakley’s success stems from reliable drivers, strategic operations, and a commitment to solving problems quickly. The conversation also reveals the complex world of trucking, where technology, customer expectations, and operational efficiency intersect to create a thriving business. Don’t miss this episode!

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250: Oakley’s New Wheels: Rental Trucks and Shop Upgrades

June 11, 2025

This week on the Oakley Podcast, Jeremy Kellett and Megan Cummings discuss important updates for truck drivers, including new medical exam submission requirements that mandate physicals be uploaded to the national registry within 24 hours. They highlight Oakley Trucking’s significant investments, including a new 18,000-square-foot trailer shop set to open in July with improved maintenance facilities and two newly purchased Kenworth rental trucks designed to help owner-operators continue working when their personal trucks are down. The podcast provides practical advice for drivers, emphasizing the importance of proactively managing medical certifications and maintaining equipment. Key takeaways include the need for drivers to be their own advocates, the benefits of the new rental truck program, Oakley’s commitment to supporting their owner-operators through innovative solutions, and more.

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249: Trucking Tunes: Tony Justice’s Road to Music and Trucking

June 4, 2025

This week on the Oakley Podcast, host Jeremy Kellet welcomes Tony Justice, a country music musician and over-the-road truck driver. Tony shares his journey, detailing his family’s trucking background and his dual career in music. He discusses his wife’s battle with breast cancer, which inspired the “Cars and Guitars for Truck Show” to raise cancer awareness. The conversation also explores Tony’s songwriting process, his band’s dynamics, and the significance of community support. The conversation also underscores a strong connection to the trucking community through Tony’s music and performances at truck shows across the country. You won’t want to miss it. 

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