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

281: From $17 to Owner Operator: Bobby Prickett’s Trucking Journey to Oakley

February 25, 2026

This week on the Oakley Podcast, host Jeremy Kellett talks with Oakley Owner/Operator Bobby Prickett about his journey from small-town Arkansas to a successful career in trucking and owning his own truck. They cover his start in the industry, being in Canada on 9/11, why he left and later returned to Oakley, and what he enjoys about end dump work, fishing, and family life. Key takeaways include the importance of watching fuel discounts, securing and maintaining equipment, and treating ownership as three jobs in one: driving, maintenance, and bookkeeping, showing that trucking can be a strong career for those willing to work hard and manage their business. 

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280: He Should’ve Died in the Crash, But God Had Other Plans

February 18, 2026

This week on the Oakley Podcast, host Jeremy Kellett talks with Oakley Owner-Operator Craig Taylor about his journey from a long, successful career in wealth management to trucking and becoming a first-time owner-operator. Craig shares his past as a high-functioning alcoholic, a devastating 2019 single-vehicle accident that nearly killed him, the long recovery that followed, and the wake-up call of alcoholic pancreatitis that led him to quit drinking cold turkey. He explains how faith, second chances, and personal responsibility shaped his return to trucking, his move to Oakley, and his approach to running his truck like a business, covering fuel strategy, costs, and what it really takes to succeed as an owner-operator. Trust us, you won’t want to miss this episode! 

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279: Clean Showers, Fresh Food, Safe Lots: Inside Road Ranger’s Driver-First Strategy

February 11, 2026

This week on the Oakley Podcast, host Jeremy Kellett talks with Kirk Waidelich, Chief Commercial Officer at Road Ranger, about how the growing travel stop chain is evolving to better serve truck drivers and auto customers. Drawing on Kirk’s 40-year retail background, they discuss Road Ranger’s expansion, particularly in Texas, and the changes driven by driver feedback, including competitive fuel pricing, cleaner showers, better food, reserved parking, and stronger loyalty perks, along with the company’s commitment to community through St. Jude partnerships. Don’t miss this great conversation! 

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