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

271: Heroism in Uniform and Behind the Wheel

November 12, 2025

This week on the Oakley Podcast, host Jeremy Kellett is joined by military veteran and Oakley owner-operator Josh Bailey for a heartfelt Veterans Day discussion. Josh shares his experiences from nearly two decades of military service, including multiple combat deployments, and discusses his transition to trucking and civilian life. The episode delves into the challenges veterans face, the unique camaraderie and pride they carry, and the important role of teamwork and support in both military and trucking careers. Key takeaways include the significance of Veterans Day, the value of veteran support, the enduring pride and resilience of those who have served, and so much more. 

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270: Diesel in His DNA: Why Rowdy Loves the Trucking Life

November 5, 2025

This week on the Oakley Podcast, hosts Jeremy Kellett and Megan Cummings welcome owner-operator Rowdy Gibbs to share his story of transitioning from the car business to trucking, highlighting the importance of passion, financial responsibility, and a supportive work environment in the trucking industry. The discussion covers Rowdy’s background, practical advice for new drivers on managing money and work-life balance, the evolving public perception of truckers, and the role of good training and company culture. Key takeaways include prioritizing savings, loving your work, the value of strong industry relationships for long-term success, and so much more. 

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269: Building an All-in-One Supply Chain: The Oakley Advantage

October 29, 2025

This week on the Oakley Podcast, host Jeremy Kellett welcomes Gregory Fallin, Alex Witkowski, and Bo Gray as the group discusses Oakley’s growth and integration across feed, fertilizer, and logistics operations, highlighting the impact of recent acquisitions like the ADM terminal. They outline how Oakley’s one-stop-shop capabilities, customer service excellence, and flexible logistics set them apart in the industry. Listeners gain behind-the-scenes insight into Oakley’s team culture, expansion strategy, and the advantages these bring for customers and drivers, along with a look at future plans for continued growth. Don’t miss this behind-the-scenes look at the company’s growth and operations.

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