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The Oakley PodcastAuthor: Oakley Trucking
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. Language: en Genres: Business, Careers, Management Contact email: Get it Feed URL: Get it iTunes ID: Get it |
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289: Forty Years on the Road: Why Getting Your CDL Is Still One of the Best Careers in America
Wednesday, 22 April, 2026
This week on the Oakley Podcast, Jeremy Kellett sits down with long-time Oakley owner-operator Tim Drake to talk about his life in trucking, from growing up in a trucking family and starting with a chauffeur’s license before CDLs, to running his own 379 Peterbilt with over 1.6 million miles. Tim shares how he transitioned from flatbed to Oakley, why he stuck with pneumatic tanks, and how careful maintenance and money management helped him pay off his truck and weather tough times. He opens up about the sacrifices of being away from family, the importance of saving for breakdowns and retirement, and the changes he’s seen in the industry, including regulations, technology, and distracted driving. Along the way, Tim talks about his passion for motocross at 57, the value of a CDL as a lifelong career option, and offers practical advice to younger drivers on working hard, living within their means, and taking care of their health and safety on the road. Key topics in today’s conversation include: We’ve Hit 100,000 YouTube Subscribers (0:25) Tim’s Background, Arkansas Roots, and Early Trucking Start (5:50) Growing Up in a Trucking Family and Riding with Mom and Dad (6:49) Getting Back into Competitive Motocross at 57 (8:19) Is Trucking a Hard Life? Sacrifices, Rewards, and Family Time (10:19) Why Tim Left Flatbedding and Chose Oakley Mileage Pay (13:27) Switching from End Dump to Pneumatic Tank Work (15:18) Advice to 27-Year-Old Tim on Saving, Hard Times, and Retirement (18:23) Mental Side of Trucking, Living in a Truck, and Staying Active (19:53) How Trucking Has Changed from “Back in the Day” (22:24) Adapting to New Rules, Regulations, and E-Logs (25:49) Why Tim Likes Pulling a Pneumatic Tank and the “Art” of Unloading (30:30) Distracted Driving, Cell Phones, and How to Really Fix the Problem (34:47) Why a CDL Is Still a Great Career Tool Anywhere You Live (39:04) Final Reflections on Trucking, Money, and Being Blessed by the Career (39:59) Oakley Trucking is a family-owned and operated trucking company headquartered in North Little Rock, Arkansas. For more information, check out our show website: podcast.bruceoakley.com. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
