The Founder

Meet
Kesha Thomas

I'm not a guru. I'm not a coach who read about drayage in a book. I'm someone who actually did the work — and built something to help you do it better.

Kesha Thomas — Founder, Drayage Academy
Kesha Thomas
Founder, Drayage Academy
The Story
Real Talk.
Real Experience.

Before I ever touched a container, I spent over 20 years in Information Technology (IT) and finance — managing projects, building systems, and making sure complex operations didn't fall apart. I have a Master's in Project Management and a Bachelor's in Computer Information Systems. I know how to take something complicated and make it work.

Then I got into trucking — and drayage found me.

We started out hauling 53' dry van before we figured out that drayage was where the real opportunity was. But nobody warned us about the red tape. The fees. The compliance. The documentation. We made expensive mistakes and learned the hard way that container freight is a completely different animal.

I took everything I knew about systems and process and applied it to drayage — and it changed everything. Over the next several years I built out our operation, figured out what actually works, and watched too many other small carriers struggle with the same things we struggled with early on.

So I built Drayage Academy
to change that.

Not theory. Not recycled content. Real operator knowledge from someone who's been in the gates, dealt with the ports, fought the fees, and built a profitable operation from scratch — so you don't have to figure it out alone.

🎓
M.S.
Project Management
💼
20+
Years in IT & Finance
🚛
7+
Years Running Drayage
📱
App
Drayage Quoter — iOS & Android
🌐
3K+
Carriers in Community
What I Bring to the Table
Multiple Perspectives.
One Mission.
💻
IT & Systems Background
Two decades in IT taught me how to build systems that don't break and document processes that actually get followed. I brought that same discipline into drayage — and it's the reason our operation ran tight.
🚢
Drayage Carrier Experience
I've been in the gates. I've dealt with demurrage charges, chassis shortages, port registrations, and railroad headaches. Everything I teach comes from real operations — not something I read about online.
🤝
Freight Broker Perspective
Understanding the broker and shipper side of drayage gives me a perspective most carriers never get. I know what customers are looking for — and I teach carriers how to show up as a professional operation that gets the freight.
📱
Tech Builder
I built the Drayage Quoter app — live on iOS and Android — because carriers needed a simple way to quote loads accurately. When I see a gap, I build something to fill it. That's just how I'm wired.
The Mission
Level the
Playing Field

Drayage Academy exists to level the playing field for owner-operators and small fleets. Big carriers have resources, teams, and systems. You're often out here figuring it out alone. That's not fair — and it doesn't have to stay that way. My goal is to engage, empower, and elevate carriers who are serious about building a real drayage business.

Hauling containers is not for the average trucker... but it can be. With the right knowledge, the right systems, and the right community — you can run a profitable drayage operation and build something that actually takes care of your family.

Engage
Empower
Elevate
Work With Me
Ready to Build
Something Real?

"My passion is to see you succeed in this market."
— Kesha, Founder of Drayage Academy

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