The Oakley Podcast

The Oakley Podcast

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.

Episodes

July 30, 2025 40 mins

This week on the Oakley Podcast, host Jeremy Kellett chats with Myers Buck & Jack Pinkerton, some of our dispatchers at Oakley Trucking. Myers and Jack share their journeys from shop work to dispatching, discussing the day-to-day challenges of managing drivers and loads, as well as the importance of communication, flexibility, and teamwork in the trucking industry. Listeners will gain insights into the human side of dispatching, th...

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This week on the Oakley Podcast, Jeremy welcomes Gerald Brown, a seasoned truck driver with 30 years of experience, who shares his remarkable journey from real estate to trucking. Gerald is an owner/operator here at Oakley and candidly discusses his career challenges, including a failed attempt at managing multiple trucks, and his transitions through various trucking jobs, ultimately finding stability with Oakley Trucking. He highl...

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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 i...

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This week on the Oakley Podcast, host Jeremy Kellett chats with Carlton & Leigh Wing, the Hosts & Founders of Wing Media Group and creators of the Arkansas Great Outdoors show. During the episode, Carlton & Leigh share their journey from broadcasting to media entrepreneurship. Leigh also shares her personal ties to trucking in the family and the appreciation everyone should have for truckers and their importance in keeping the coun...

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This week on the Oakley Podcast, host Jeremy Kellett welcomes Brian Carpenter, one of our owner/operators at Oakley Trucking. During the episode, Brian, a 30-year veteran truck driver, shares his rich and diverse background. A former Army artillery soldier who transitioned from seminary school to trucking, Brian discusses the challenges of trucking, including navigating traffic and hauling complex loads like bauxite dirt, while emp...

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This week on the Oakley Podcast, host Jeremy Kellett chats with Jason Webb & Bradley Simpson, Operations Managers at Oakley Trucking. During the conversation, the group provides an insider's view of managing bulk freight across pneumatic and end dump divisions. They discuss the challenges of coordinating over 900 owner operators, emphasizing the critical importance of communication, customer service, and building strong relationshi...

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This week on the Oakley Podcast, Jeremy Kellett and Megan Cummings discuss important updates for truck drivers, including new medical exam submission requirements that mandate physicals be uploaded to the national registry within 24 hours. They highlight Oakley Trucking's significant investments, including a new 18,000-square-foot trailer shop set to open in July with improved maintenance facilities and two newly purchased Kenworth...

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Key topics in today’s conversation include:

  • Welcoming Tony Justice to the Show (1:27)
  • Inspiration behind the Cars and Guitars Truck Show (2:56)
  • Tony's Family Background (6:03)
  • Balancing Music and Trucking (8:58)
  • Transitioning to Full-Time Music (10:44)
  • Collaboration with Aaron Tippin (13:09)
  • Songwriting Process (17:06)
  • Tony’s Musical Influences (22:20)
  • Career and Audience (25:11)
  • Future Plans (27:19)
  • The Story Behind Tony’s Truck Named "P...
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Key topics in today’s conversation include:

  • Welcoming Alex to the Podcast (1:56)
  • Military Contracts Explained (4:38)
  • Skills Gained from Military Service (7:54)
  • Alex’s First Truck Experience (14:36)
  • Becoming an Independent Contractor (17:23)
  • Purchasing a Truck (19:19)
  • Understanding Business (21:59)
  • Financial Planning (23:17)
  • Fuel Costs (25:21)
  • Fuel Efficiency Habits (27:20)
  • Speed Management (31:50)
  • Analyzing Empty vs. Loaded Miles (37:47)
  • Av...
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Key topics in today’s conversation include:

  • Chris's Trucking History (1:15)
  • Truck Maintenance Insights (2:24)
  • Chris's Start in Trucking (3:53)
  • Changes in Trucking Over 30 Years (7:27)
  • Advice for New Truck Drivers (8:53)
  • Carter's Future in Trucking (10:50)
  • Memories of Trucking (12:11)
  • Final Thoughts and Takeaways (16:43)

Oakley Trucking is a family-owned and operated trucking company headquartered in North Little Rock, Arkansas. For...

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Key topics in today’s conversation include:

  • Jimmy's Background and Trucking Journey (1:56)
  • Overcoming Fear of Change (4:17)
  • Military Background Correlation (7:30)
  • Oakley’s Reputation (9:25)
  • Differences in Trucking Types (15:25)
  • Inspiration for YouTube Channel (17:42)
  • Advice for Starting a YouTube Channel (20:22)
  • YouTube as a Recruiting Tool (23:25)
  • Public Perception of Truck Drivers (24:01)
  • Health Awareness for Truck Drivers (26:46)
  • Futur...
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Key topics in today’s conversation include:

  • Bryan's Background in Trucking (2:05)
  • Evolution of 4 State Trucks (3:23)
  • Impact of "Trick My Truck" (7:08)
  • Reality of Reality TV (8:37)
  • Origin of Chrome Shop Mafia (10:46)
  • Trends in Truck Customization (16:24)
  • Guilty by Association Truck Show Origins (20:26)
  • Entertainment at the Truck Show (24:44)
  • Community and Camaraderie in the Trucking Community (27:16)
  • Future Plans for 4 State Trucks (28:05...
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Key topics in today’s conversation include:

  • Bruce Background and Journey (1:11)
  • Importance of Early Exposure to Trucking (5:05)
  • Owner-Operators and Their Resilience (6:05)
  • The Appeal of Trucking (8:52)
  • Community Support Among Truckers (10:32)
  • Performance of Various Engines (13:14)
  • Bruce’s Personal Retirement Reflections (15:12)
  • Listening to Customer Needs (20:43)
  • Hurricane Helene Damage (27:51)
  • Retirement Realities (38:01)
  • The Addiction t...
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Key topics in today’s conversation include:

  • Wreaths Across America Overview (1:13)
  • Growth of the Program (2:46)
  • Impact on Trucking Industry (4:05)
  • Wreath Placement Ceremony Date (5:56)
  • Wreath Production Process (8:07)
  • Driver Experience at Wreaths (9:57)
  • The Remembrance Tree Program (14:26)
  • Continued Growth of the Program (16:37)
  • Courtney’s Background and Journey to WAA (20:13)
  • Engagement with Veterans (23:21)
  • Opportunities for Participati...
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Key topics in today’s conversation include:

  • Welcoming Joe to the Podcast Live from MATS (1:08)
  • History of Lone Mountain Truck Leasing (3:35)
  • Current Status of Truck Leasing (4:50)
  • What Sets Lone Mountain Apart (6:20)
  • Approval Process for Leasing (8:14)
  • Service Contracts and Warranties (11:17)
  • Truck Specialization and Purchasing Strategy (14:53)
  • Service Reliability (18:06)
  • Independent Contractor Trends (19:42)
  • Market Dynamics (23:10)
  • Conne...
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Key topics in today’s conversation include:

  • Previewing Upcoming Episode with MATS (1:31)
  • Podcast Growth and Future Plans (3:34)
  • Mid-America Truck Show Introduction (8:47)
  • Lewie Pugh Joins the Podcast (9:13)
  • Challenges in Finding Qualified Drivers (11:44)
  • Industry Turnover Rates (12:54)
  • Raising Standards in Trucking (14:00)
  • Changing Demographics in Trucking (17:31)
  • Back to Basics in Trucking (19:46)
  • The Importance of Basic Skills (21:55)
  • U...
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Key topics in today’s conversation include:

  • Previewing Today’s Episode (0:38)
  • Spotify Playlist Announcement (2:06)
  • Brent's Retirement Announcement (3:06)
  • Hobbies and Future Plans (7:51)
  • Building a House in the Philippines (9:02)
  • Challenges of Building Abroad (11:06)
  • Retirement Plans and Reflections (13:40)
  • Trucking Experience and Industry Changes (15:02)
  • Favorite Aspects of Trucking (17:24)
  • Route Driver Insights (20:30)
  • Memorable Pneumati...
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Key topics in today’s conversation include:

  • Introducing Today’s Topic (0:12)
  • Evolution of Advertising (3:13)
  • Changes in Marketing Strategies (4:43)
  • Fragmentation of Audiences (6:39)
  • Challenges of Targeting Drivers (10:16)
  • Common Marketing Mistakes (12:43)
  • Importance of Authentic Messaging (15:10)
  • Introduction to Digital Advertising (18:00)
  • Local Advertising Success (19:53)
  • YouTube's Role in Company Culture (22:08)
  • The Impact of Short-Form...
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Key topics in today’s conversation include:

  • Previewing Today’s Episode with Cruz (0:12)
  • Come See Us at MATS (3:02)
  • Cruz’s Background and Journey in Trucking (7:33)
  • Becoming an Owner Operator (12:09)
  • Purchasing a New Truck (13:40)
  • Cruz's Girlfriend: Professional Boxer (16:11)
  • Experience with Dump Trailers (17:31)
  • Reasons for Staying in Trucking (18:44)
  • Adjusting to a New Truck (20:24)
  • Future Aspirations in Trucking (23:45)
  • Advice for Aspir...
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Key topics in today’s conversation include:

  • Previewing Today’s Episode (0:12)
  • New Business Opportunities (3:03)
  • Regulatory Processes (4:41)
  • Customer Reactions (7:03)
  • Experience in Waste Remediation (9:29)
  • Flexibility on Job Sites (12:26)
  • Importance of Trailer Preparation (14:59)
  • PPE Requirements (18:14)
  • Trailer Cleanliness Procedures (21:33)
  • Dumping Conditions at Landfills (24:15)
  • Industry Competition and Opportunities (26:02)
  • Feedback fro...
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