Podcast Episodes

289: Forty Years on the Road: Why Getting Your CDL Is Still One of the Best Careers in America

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.

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288: Oakley’s Trucking Success at Port 33: Growing from 40 to 150 Trucks

This week on the Oakley Podcast, Jeremy Kellett takes the Oakley Podcast on the road to Oakley’s Port 33 terminal in Catoosa, Oklahoma, to spotlight terminal manager Justin Jolly and operations manager Kyle Haney. They share the origin story of the Oklahoma terminal, from working out of an RV on a dusty gravel lot to running about 150 trucks today, while explaining how the port’s barge, grain, fertilizer, and local industrial freight created a powerful home‑time‑friendly operation. Kyle walks through day‑to‑day dispatch realities (breakdowns, tires, planning, and tight coordination with North Little Rock and Reserve), and both men stress relationship‑based dispatch, face‑to‑face communication with drivers, and proactive communication with customers. Key takeaways: Oakley’s growth in Oklahoma has been steady and intentional, built on dependable service, clean and professional owner‑operators, integrated barge‑truck logistics, and a strong culture of transparency and trust with both drivers and customers. Don’t miss this episode! 

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287: From the Road to the Bank: How ATBS Helps Truckers Take Control of Their Finances

This week on the Oakley Podcast, Jeremy Kellett sits down with Todd Amen, president of ATBS, to break down the 2026 trucking market, how recent tax law changes (including the Big, Beautiful Bill Act) impact owner operators, and what truck drivers should be doing right now in tax season. They cover extensions, quarterly estimated taxes, the power of the qualified business income deduction, and how per diem really works in simple, practical terms. Todd explains common, often-overlooked deductions specific to truckers, how the ATBS app helps track income, expenses, and per diem, and why maintaining reserves and smart money management separate profitable owner-operators from those who struggle. The episode closes with guidance for drivers who are behind on taxes, free tools available from ATBS, and how Oakley owner operators compare financially to the broader industry.

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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.