The Road That Built Me

My name’s Rob Carpenter, and I’m your go-to driver voice for The Playbook. Whether you’re driving out on the road or running your own trucking business, I’m here to help you cut through the noise and figure out what actually works at a practical level. The Playbook, Roadmap, and Masterclass are all about giving you the real-world tools and strategies to succeed, no fluff, just straight-up practical advice. I grew up on a backwoods Virginia farm, raised by my grandparents and great-grandparents hardened by the depression and the aftermath of it. From an early age, I was learning about mechanics, problem-solving, and the realities of hard work. I had to find my way to freight, trucking, and supply chain and did that successfully because I had serious mentors who knew the key was to teach me everything they had spent their lifetime learning. I hope you find your mentorship here with us in The Playbook.

I got my CDL 22 years ago with all the endorsements, but as anyone in this industry knows, you don’t start with good jobs. Companies want documented experience with reputable carriers, meaning you take the hard, honest, dirty, sometimes nasty work that no one else wants. I did tree work, moved furniture, pumped human waste, and whatever it took to get my time in. The work was brutal, but I knew it was temporary. I wasn’t going to be a dead-end driver. That was not the path I wanted forever, my entrepreneurial spirit pushed harder for better, for growth, for more. 

The key to moving forward was commoditizing myself. I wasn’t just a driver. I needed to understand the entire industry. I networked with leadership, sales, brokerage, HR, dispatch, and maintenance people. I became a broker agent with BlueGrace, learning the business side of transportation and how carriers, brokers, forwarders, steamship lines, and rail companies operate independently and together.

I kept driving while running small and mid-sized fleets. One of those was part of Wanchese Fish Company, and when our owner retired after selling the boats, I took over. It was my business, finally. I thought it was all cake from then on, but little did I know it would be one of my life’s most cash-flow-intensive, sink-or-swim moments. I expanded the business, got my broker authority, and never had to refuse freight. If I couldn’t haul it myself, I could move it through the brokerage. That artificial capacity changed everything. As an agent, I added international freight forwarding under Berkshire Hathaway’s BNSF Logistics. Why? Because I failed the customs broker exam, but this gave me control over international exports and imports while integrating rail alongside trucking. I had built a broad, efficient, and not mode-specific network.

Then everything changed. I was in a crash. A bad one. An illegal immigrant operating an unregistered farm vehicle hit me, and I ended up needing a spinal fusion from my hips to my mid back. That accident didn’t just take my physical ability to drive full-time initially, It changed how I saw the industry. I was an outlaw. I was known to frequently drive with countless logbooks or loose leaf grid logs, running as many as 40 hours without sleep. I had always prioritized efficiency and revenue, but now I saw firsthand how safety and compliance mattered in ways I hadn’t fully appreciated before.

I sold the business to a carrier I had helped grow from an owner-operator to a fully independent fleet. From there, I transitioned into fleet safety, compliance, and FMCSA regulations. I started building scalable safety programs, integrating systems, and working with some of the biggest companies in the world, both independently and through TruckSafe Consulting. The deeper I went, the more I realized that trucking isn’t just about moving freight. It’s about moving it legally and safely. The industry doesn’t care how much money you make; you won’t stay in business if you aren’t compliant.

To stay ahead, I kept learning, sharpening my skills in every avenue, including on some things people said I would never need. Some said I would never use those skills in trucking. I learned Spanish to better communicate with fleet employees, learned PHMSA and pipeline safety for pipeline logistics for specialized clients, crash reconstruction to better manage claims, HR compliance to understand the hiring, recruiting, and retention of employees and labor law, drug and alcohol testing, management and collection to manage drug and alcohol programs, autonomous vehicle safety, took vehicle course better to understand vehicle dynamics and maintenance, and driver training and coaching to understand better how to coach and run drivers to improvement. I immersed myself in everything because knowledge is leverage, and mentorship is the shortcut. You can read every regulation and policy, but 90% of success in this industry comes from experience or the wisdom passed down by people who’ve done it before you.

That’s why I believe mentorship is everything. I didn’t get here alone. I learned lessons from those willing to teach, and I believe in paying that forward. I’ve helped dozens of new drivers become owner-operators, and an equal number of owner-operators operate under their own authority.  I answer messages, give advice, and help people without charging them because that’s how this industry should be. Trucking isn’t a competition. There’s room for everyone. The winners are willing to learn, evolve, and pass that knowledge down to the next in line.

For me, it has always been about being better than I was yesterday. I don’t have an ego too big to learn from anyone, and I don’t believe in gatekeeping knowledge. If someone is willing to listen, I’ll help them however I can. That’s what trucking should be. That’s what life should be. It should be an industry where people look out for each other. The dog-eat-dog mentality of modern-day trucking is toxic. Mentorship builds the next generation. Your success is measured in the knowledge you pass down to those coming up behind us.

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