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

243: Honoring Heroes: Wreaths Across America with Courtney George

April 23, 2025

During this week’s episode of the Oakley Podcast, host Jeremy Kellett is joined by Courtney George,  Director of Transportation and Industry Relations at Wreaths Across America, live from the Mid-America Truck Show in Louisville, Kentucky. In this powerful conversation, Courtney shares the inspiring mission of honoring veterans by placing wreaths on military graves nationwide. The program has grown from 5,000 wreaths in 1992 to over 3.1 million wreaths at nearly 5,000 locations, highlighting the trucking industry’s crucial role in supporting this meaningful tribute to fallen heroes. Listeners will learn about the program’s growth, emotional impact, and how individuals can contribute to remembering and respecting those who have served. You won’t want to miss this great conversation. 

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242: Breaking the Leasing Stigma: An Honest Approach to Truck Financing

April 16, 2025

During this week’s episode of the Oakley Podcast, host Jeremy Kellett is joined by Joe Hoovestol, General Manager at Lone Mountain Truck Leasing. In this conversation, Jeremy and Joe look at a transparent approach to truck leasing for independent owner-operators. Joe explains their unique model that helps drivers acquire trucks without hidden fees, highlighting their success in helping nearly 12,000 operators complete truck payments. The conversation also explores current trucking market challenges, including frustrating after-treatment systems, volatile truck prices, and the complexities of entering the trucking industry. Key takeaways include the importance of understanding market conditions, building long-term relationships, and choosing a leasing partner that prioritizes the owner-operator’s success. Don’t miss it!

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241: Back to the Basics: Solving the Trucking Industry’s Biggest Challenges

April 9, 2025

During this week’s episode of the Oakley Podcast, host Jeremy Kellett is joined by Lewie Pugh, Executive Vice President of Owner-Operator Independent Drivers Association (OOIDA) live from the Mid-America Truck Show in Louisville, Kentucky. In this conversation, Lewie gives a powerful critique of the trucking industry, highlighting critical challenges in driver training, retention, and technological adaptation. Discussing legislative insights and practical advice, Lewie emphasizes the need to invest in drivers, find specialized niches, and prioritize quality over quantity. The conversation also exposes the industry’s systemic issues while offering hope through advocacy, continuous learning, and supporting organizations like OOIDA that fight for truckers’ rights. Listeners will gain valuable insights into the complex world of trucking, understanding that success comes from returning to basics, valuing experienced drivers, actively engaging in industry improvements, and more.

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