The Oakley Podcast

This week on the Oakley Podcast, Jeremy and Megan sit down with Rick Rupe, one of our owner/operators at Oakley. Rick shares his journey from farming to trucking, the importance of family support, and the realities of life on the road. Rick shares insights on balancing farm and trucking responsibilities, the decision-making process behind becoming an owner-operator, and practical advice for those considering the leap. The conversation also addresses common misconceptions about truck drivers and emphasizes the value of perseverance, adaptability, and community in the trucking industry. Key takeaways include the importance of doing your homework before buying a truck, maintaining a healthy work-life balance, and staying open to new opportunities.

Key topics in today’s conversation include:

• Episode Preview & Welcoming Megan Back (0:51)
• Rick Rupe’s Owner/Operator Story (4:16)
• Farming Background and Entry into Trucking (6:44)
• Transition from Chicken Farming to Trucking (10:10)
• Decision Process to Join Oakley (14:13)
• Gaining Confidence to Become Owner-Operator (16:20)
• Upgrading Trucks and Changing Divisions (20:21)
• Learning the Plastics Division (23:35)
• Myths About Truck Drivers (24:44)
• Advice for Aspiring Owner-Operators (30:33)
• Financial Realities and Family Support (33:50)
• Final Thoughts and Takeaways (34:20)

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.

This week on the Oakley Podcast, host Jeremy Kellett welcomes Kevin Hensley, an Owner/Operator at Oakley with over 20 years of experience, as the two debunk common myths about truck drivers. They discuss the diverse backgrounds and education levels of truck drivers, the strict safety and health regulations they follow, the financial opportunities in the industry, and the role of technology in modern trucking. Kevin also shares insights from his experiences on the road, highlighting the discipline, responsibility, and adaptability required for success. Listeners will gain a deeper appreciation for the challenges and rewards of a trucking career, and a better understanding of the vital role truck drivers play in everyday life. Don’t miss this myth-busting episode. 

Topics in today’s conversation include:

• Kevin’s Background and Entry into Trucking (1:59)
• Myth 1: Truck Drivers Are Uneducated (4:09)
• Truck Driver Qualifications and Physicals (7:55)
• Daily Routine and Regulations (9:09)
• Myth 2: Truck Drivers Are Unsafe/Outlaws (11:25)
• Importance of Safety in Trucking (13:44)
• Myth 3: Truck Drivers Don’t Make Money (16:22)
• Owner-Operator Responsibilities (18:09)
• Technology in Trucking (21:54)
• Myth 4: Truck Drivers Are Lazy (25:10)
• The Future of Trucking (27:11)
• Kevin’s Motocross Hobby (32:03)
• Final Thoughts and Takeaways (35:26)

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.

This week on the Oakley Podcast, host Jeremy Kellett chats with Jared Smith, one of our new owner/operators at Oakley. Jared talks about his first month at Oakley Trucking, sharing his journey from company driver to independent contractor. He discusses the challenges of making the leap, the importance of family and faith, and the support he’s received from Oakley’s team. The conversation covers orientation, adapting to new technology, financial planning, and the value of a strong support system both at home and on the road. Key takeaways include the importance of taking risks, building a solid foundation for your family, the benefits of joining a company that values its drivers and fosters a supportive community, and so much more.

Key topics in today’s conversation include:

• Meet Jared Smith: Background and Family (3:07)
• Jared’s Path to Oakley (4:30)
• Career History: Firefighting and Oilfield Work (6:07)
• Transition to Owner-Operator (9:41)
• First Month at Oakley: Orientation and Training (14:07)
• On-the-Job Training and Field Support (15:42)
• Toughest Challenges on the Road (18:53)
• Explaining Trucking to the Public: ELDs and Safety (21:13)
• Oakley vs. Other Trucking Companies (25:47)
• Learning Finances as an Owner-Operator (26:19)
• Health, Food, and Staying Active as a Driver (29:11)
• Jared’s Goals for the Future (32:12)
• Final Thoughts and Takeaways (36:59)

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.

This week on the Oakley Podcast, host Jeremy Kellett brings in Corey Huey, Kent Childers, and Dustin Eagle from the Oakley recruiting department as the group talks about the company’s approach to recruiting and retaining top owner-operators. They cover Oakley’s unique benefits—including pay for all miles, weekly settlements, anniversary and referral bonuses, fuel and insurance discounts, and no trailer rental fees—while emphasizing the importance of transparency, relationship-building, and setting clear expectations with recruits. Listeners gain insight into the daily challenges recruiters face, the company’s supportive culture, how Oakley’s commitment to its drivers sets it apart in the trucking industry, and so much more. 

Key topics in today’s conversation include:

• Podcast as a Recruiting Tool (1:12)
• Basics of the Recruiting Call (4:34)
• Pre-Qualifying and Relationship Building (6:25)
• Explaining Pay Structure and Incentives (8:38)
• Anniversary Bonus Program (13:07)
• Company Culture and Personal Touch (16:23)
• Financial Benefits and Savings for Owner-Operators (18:12)
• Referral Bonus Program (20:34)
• Long-Term Recruiting and Relationship Management (24:37)
• High Standards and Application Rejection (26:29)
• Setting Expectations with Recruits (29:22)
• Recruiters’ Multifaceted Roles (32:13)
• Retention Through Recruiting Process (34:06)
• Final Thoughts and Takeaways (36:21)

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.

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, the value of building strong relationships with drivers, and the critical role dispatchers play in ensuring both company and driver success. Key takeaways include the need for adaptability, clear communication, and understanding the unique challenges faced by both dispatchers and drivers. Don’t miss this inside look at how dispatchers keep trucks on the road.

Key topics in today’s conversation include:

• Meet Myers and Jack: Backgrounds and How They Joined Oakley (1:03)
• First Impressions and Shop Experience (2:55)
• Transition to Dispatch: Learning the Ropes (7:26)
• Challenges of Dispatching and Building Relationships (9:23)
• A Day in the Life of a Dispatcher (12:15)
• Ensuring Drivers’ Earnings and Settlement Checks (14:21)
• Regulatory Compliance and Administrative Duties (17:02)
• Building Personal Relationships with Drivers (21:04)
• Orientation and Understanding Driver Rules (24:22)
• Load Planning and Communication with Drivers (26:15)
• Customer Interaction and Cold Calling for Freight (29:17)
• Advice for Drivers: Flexibility and Communication (33:15)
• Company Culture and Camaraderie (34:53)
• Final Thoughts and Takeaways (36:41)

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.

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 highlights the importance of a supportive spouse, effective truck maintenance, and adaptability in the trucking industry, currently transitioning from hopper to pneumatic tank hauling. Gerald also offers insights into the daily challenges of trucking, such as parking difficulties, traffic congestion, and the impact of technology like e-logs. The episode provides a personal and inspiring narrative about perseverance, learning from failures, and finding success as an owner-operator, with Gerald emphasizing that having a strong support system and being willing to embrace new challenges are key to thriving in the trucking profession. You won’t want to miss this! 

Key topics in today’s conversation include:

• Welcome to Today’s Episode (1:05)
• 2290 Tax Form Reminders (2:51)
• Heat Safety and Company Calendar (4:20)
• Gerald Brown’s Background and Family (9:12)
• Balancing Trucking and Family Life (11:30)
• Gerald’s Path to Trucking (13:02)
• Owner-Operator Challenges and Fleet Ownership (16:43)
• Financial Setbacks and Recovery (19:05)
• Starting at Oakley and Early Setbacks (23:38)
• Switching Divisions and New Truck Purchase (00:25:14)
• Truck Maintenance Philosophy (28:48)
• Parking and Hours-of-Service Challenges (30:25)
• Biggest Challenges in Trucking Today (32:59)
• Importance of Family and Support (35:04)
• Bulk Trucking vs. Other Segments (37:40)
• Future Plans for Gerald and Parting Thoughts (39:09)

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.

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 intense interest in trucking, using American Truck Simulator and already planning to start his own company in the future. The episode explores changes in the trucking industry, the importance of family values, understanding of trucking regulations, and truck models. Key takeaways include the evolving nature of trucking, the significance of mentorship even from parent to child, the potential for young, passionate individuals to innovate in the transportation industry, and so much more. 

Key topics in today’s conversation include:

• Welcome to the Episode (0:46)
• Oakley Trucking Recruiting Needs (1:19)
• Celebrity Encounter Story (4:54)
• Preview of the Episode & Past Highlights (9:30)
• Introducing Fred and Jerome Levy (13:31)
• Fred’s Early Trucking Career (17:35)
• Jerome’s Introduction to Trucking and Passion for Trucks (20:45)
• Fred on Family, Purpose, and Jerome’s Passion (24:43)
• Fred’s Career Path Before Oakley (26:26)
• Fred’s Experience at Oakley (30:01)
• Jerome’s Business Aspirations (33:51)
• Changes in Trucking Over the Years (37:58)
• Trucking Regulations and Cleanliness (41:13)
• Jerome’s Training and Future Plans (45:25)
• Generational Lessons and Family Support (47:41)
• Final Thoughts and Conclusion (49:12)

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.

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 country running. The Wings highlight Arkansas's incredible natural resources, emphasizing the state's diverse outdoor opportunities and the importance of getting people, especially youth, engaged with nature. Carlton also reveals his recent decision to step back from politics after serving in the House of Representatives for 10 years. Throughout the conversation, they stress the therapeutic benefits of outdoor experiences and the joy of discovering new activities like fishing, hiking, and exploring state parks. Don’t miss it!

Key topics in today’s conversation include:

• Welcoming the Wings to the Show (1:18)
• Carlton’s Broadcasting Journey (4:34)
• Personal & Family Background (6:12)
• Moving to Arkansas & Love for the Outdoors (8:11)
• Overcoming Career Setbacks (12:27)
• Birth of Arkansas Great Outdoors Show (14:51)
• Expanding Outdoor Content (18:24)
• Arkansas’ Outdoor Reputation (22:15)
• Game & Fish Commission and State Parks (24:01)
• Carlton’s Political Career (25:48)
• Future Plans for the Wings (29:30)
• Favorite Fishing Techniques (32:43)
• The Benefits of Getting Outside (35:50)
• Final Thoughts and Takeaways (39:11)

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.

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 emphasizing the importance of patience and safety. Beyond driving, Brian reveals his passions: riding his Harley, volunteering at a music theater, supporting a Christian country radio station, and maintaining a positive TikTok presence. With a pilot's license and a love for old country music, Brian represents the multifaceted nature of professional truck drivers - dedicated professionals who are much more than just drivers. The episode highlights the personal stories, challenges, and diverse interests that define modern trucking professionals, offering listeners a nuanced and inspiring view of life on the road. Don’t miss it!

Key topics in today’s conversation include:

• Permits, Licensing, and 2290s (1:59)
• Upcoming Vacation Plans (4:13)
• Jeremy’s Surprise in NYC (5:07)
• Introducing Brian Carpenter (11:59)
• Brian’s Background and Family (13:21)
• Friendship and Owner-Operator Community (17:26)
• Military Service Reflections (19:15)
• Transition to Oakley and Truck Ownership (22:39)
• Unique Loads and Memorable Deliveries (24:09)
• Favorite Things About Oakley (27:31)
• Accidents and Road Stories (32:05)
• Brian’s Hobbies and Volunteering (36:13)
• Radio Station Volunteering (38:47)
• Bryan’s TikTok and Pilot’s License (40:20)
• Final Thoughts and Takeaways (42:41)

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.

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 relationships. With over 1,000 customers and opportunities for growth, the podcast highlights how Oakley's success stems from reliable drivers, strategic operations, and a commitment to solving problems quickly. The conversation also reveals the complex world of trucking, where technology, customer expectations, and operational efficiency intersect to create a thriving business. Don’t miss this episode!

Key topics in today’s conversation include:

• Previewing Today’s Episode (0:12)
• Role of Operations Managers and Dispatchers (4:04)
• Current State of Freight: End Dumps and Pneumatics (7:14)
• Challenges: Capacity and Missed Opportunities (10:00)
• Customer Base and Untapped Potential (12:54)
• Communication: The Key Challenge (15:06)
• Booking Loads: Then vs. Now (17:23)
• Building Customer Relationships (20:13)
• Oakley’s Competitive Edge (22:12)
• Customer Feedback and Owner-Operator Excellence (25:09)
• Importance of Customer Service and Owner-Operator Standards (30:04)
• Behind-the-Scenes Operations and Trust (33:33)
• Looking to the Future (37:18)
• Final Thoughts and Takeaways (39:23)

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.