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

276: Battling on Two Fronts: Leadership & Family Sacrifice

January 21, 2026

This week on the Oakley Podcast, host Jeremy Kellett interviews Major General Bob Walters, exploring his extraordinary career in the U.S. Army, the challenges of military leadership, and the profound impact on his family. Walters shares captivating stories from deployments around the globe, including operations in Iraq, Afghanistan, and the notable Abu Ghraib experience. The episode also touches on the parallels between military discipline and the trucking industry, promoting Walters’ new book about leadership in tough times. Key takeaways include the sacrifices made by military families, the value of steadfast leadership under pressure, the strong ties between veterans and the world of trucking, and so much more. 

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275: Tariffs, Tech & Tough Markets: How Oakley Thrived in 2025

January 14, 2026

This week on the Oakley Podcast, host Jeremy Kellett is joined by ops managers Nick Dulaney and Jason Webb to review Oakley Trucking’s milestones and challenges in 2025 and look ahead to 2026. Topics include overcoming a tough freight market, the impact of tariffs, equipment and trailer updates, and maintaining high safety and service standards. The discussion highlights proactive strategies for customer retention, operational improvements using data and AI, fostering company culture, annual bonuses, and the significance of the new St. Louis terminal. Key takeaways are Oakley’s commitment to its drivers, adaptability in changing markets, positive outlooks for growth and efficiency in 2026, and so much more. 

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The Oakley Podcast: From the Archives – Wheels of Wisdom: A Father, Son, and a Love for Trucking

January 7, 2026

We’re taking a look back at some of our favorite episodes of 2025. This week on the Oakley Podcast, Megan Cummings and Dustin Eagle bring you another great episode as they welcome Fred & Jerome Levy. Fred is an Owner/Operator here at Oakley, and his son Jerome is already planning his trucking career. Fred, who started driving with Pepsi and transitioned to over-the-road trucking, discusses his career path and joining Oakley Trucking. Jerome, already knowledgeable in the industry, demonstrates an intense interest in trucking, using American Truck Simulator and already planning to start his own company in the future. The episode explores changes in the trucking industry, the importance of family values, understanding of trucking regulations, and truck models. Key takeaways include the evolving nature of trucking, the significance of mentorship even from parent to child, the potential for young, passionate individuals to innovate in the transportation industry, and so much more.

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