An Open Letter to the Trucking Industry: The Playbook Is Here

There are moments in life when an idea takes shape in a way you never expected — when the right conversation happens at the right time, setting off a chain reaction that leads to something bigger than you anticipated.

For me, that moment started with a tweet.

I was sharing my thoughts on a compliance issue — one of the many daily battles small carriers and owner-operators face — when Craig Fuller, CEO of FreightWaves, saw it. He reached out via direct message, inviting me to speak at the FreightWaves F3 Future of Freight Festival in Chattanooga, Tennessee. What began as a simple tweet turned into a 15-minute conversation on stage, one that resonated so deeply that when we stepped off, we both knew it couldn’t end there.

A few weeks later, we met on Zoom, and as we started talking, the first thing that came to our minds was The Playbook.

Why The Playbook?

Because for as long as I’ve been in this industry — 25 years and counting — there has never been a truly comprehensive resource for small carriers, owner-operators or those looking to become one.

Back when I got started, there was nothing — no centralized information, no real roadmap for success. You learned by trial and error, often at a high cost. Today, while information is easier to find, it’s fragmented. More importantly, it’s often flat-out wrong.

Social media has made it easier than ever for misinformation to spread, and truckers are paying the price for bad advice. I’ve seen it firsthand — people losing their businesses because they followed the wrong guidance, overpaying for services they didn’t need or failing to build sustainable operations because they never had the right playbook to follow.

That’s why we built The Playbook — to give small carriers the right information, in the right way, at the right time.

What Is The Playbook?

The Playbook isn’t just a website. It’s not a course. It’s not just another content hub. It’s a one-stop resource designed to give trucking business owners and aspiring ones the exact tools they need to succeed in an industry that’s only getting more competitive.

The Playbook is built on education, data and community. It provides clear, fact-based guidance on the key areas of running a trucking business: compliance, finance, operations and sales. But more than that, it’s a structured, ongoing resource that ensures small carriers have everything they need to build and scale their business the right way.

The Playbook includes:

• A digital learning hub with structured courses and training on critical trucking business topics. This isn’t scattered, outdated information — it’s a step-by-step roadmap built on real-world experience.
• A biweekly Masterclass designed to go deep into essential topics such as pricing strategies, compliance updates, shipper outreach and more.
• A monthly Small Carrier Market Update, providing insight into freight trends, rate shifts and industry changes that directly impact small carriers and independent owner-operators.
• Industry-specific data and insights backed by FreightWaves, ensuring Playbook members get access to real-time market intelligence that larger carriers have relied on for years.
• The Long Haul podcast, bringing real conversations about the industry, business growth and the challenges that small carriers face. This will feature deep-dive discussions with industry leaders, successful carriers and subject matter experts.
• A partner portal connecting small carriers with vetted, reliable industry partners offering services designed to help them grow and operate more efficiently.
• Special Playbook events, including in-person workshops, networking sessions, and exclusive access to FreightWaves conferences and discussions tailored to small carriers.
• Real case studies and expert interviews showcasing successful small carriers that have built sustainable, profitable trucking businesses.
• Tools and templates, including spreadsheets, calculators, contract templates and other essential business resources that help small carriers run their operations without having to start from scratch.

Why FreightWaves?

Because FreightWaves is the pulse of the industry.

FreightWaves isn’t just a news source — it’s a powerhouse of data, analytics and insights that the biggest players in the industry rely on every day. But for too long, small carriers have been left out of the conversation. They’ve had to piece together information from unreliable sources, trying to compete in an industry where knowledge is power — and where, too often, that knowledge hasn’t been accessible to the very people who need it most.

The Playbook is changing that.

By partnering with FreightWaves, we’re ensuring that small carriers, independent owner-operators and those just getting started finally have access to the same level of insight and strategy that larger carriers have used to dominate the industry for years.

Why Me?

Because I’ve been exactly where you are. From day one. As soon as I was old enough to get my CDL, I had it.

I started in this industry behind the wheel, grinding it out as a driver with nothing but a truck and a Yellow Pages to find loads. I built a fleet from scratch, navigated the ups and downs, and made every mistake in the book — mistakes that cost me money, time and opportunities.

But I learned. I adapted. And most importantly, I found better ways to do things.

For years, I’ve dedicated my journey to helping small carriers not just survive, but thrive. Through coaching, mentorship and training, I’ve helped countless trucking business owners build sustainable, profitable companies. Now, with The Playbook, I’m bringing that mission to an even bigger audience.

This is more than just content. This is the real playbook for success in trucking.

The Future Starts Now

The Playbook isn’t just a project. It’s a movement.

It’s the start of something that should have existed a long time ago — a structured, trusted, fact-based resource for small carriers and owner-operators who are tired of sifting through bad advice and misinformation.

And this is just the beginning.

The Playbook will grow. It will evolve. It will become the go-to resource for small carriers looking to gain an edge in an increasingly complex industry.

Because at the end of the day, my mission remains the same:

I want to leave the industry in a better place than I found it.

Bio

Adam Wingfield is the founder and managing director of Innovative Logistics Group, a Charlotte, North Carolina-based trucking consulting and carrier services firm that focuses on providing resources and success guidance to small carriers. He is a 22-year industry vet who started in the industry as an OTR company driver and quickly progressed to fleet ownership, purchasing his first semi-truck at 23. He graduated magna cum laude in business management/supply chain from Strayer University.

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