Introduction: Five Years in Review

Over the past five years, I’ve worked my way up from being a solo operator handling freight movements to running a small but growing logistics business. Reflecting on those years, it’s clear that scaling in logistics isn’t just about adding trucks or booking more loads—it’s about figuring out how to manage chaos, build trust with clients, and maintain profitability in an industry that thrives on tight margins and constant change.

This isn’t a “perfect success story” about flawless systems or endless wins. It’s a real-world look at the challenges logistics professionals face daily: juggling operational problems, managing clients’ expectations, finding good drivers, and keeping cash flow steady. If you’ve ever been up at 2 a.m. trying to find an empty chassis or explaining a delay to a furious customer, you’ll know exactly what I mean.

Here are five hard-learned lessons I wish I’d known sooner.

Lesson #1: The Freight Isn’t Always the Problem—The System Is

When I first started, I focused 100% on moving freight. “If the truck moves, the business grows,” I thought. But over time, I realized that running a successful logistics operation isn’t just about moving loads—it’s about building systems that can handle volume without breaking down.

What this looks like in practice:

• Example 1: Tracking Deliveries

Early on, I’d call drivers, update spreadsheets, and try to keep clients in the loop manually. This worked for 5 loads a week, but at 25 loads, it became impossible. Clients were frustrated, drivers were confused, and I was exhausted. Introducing simple tech tools like diginetics, something with visibility platforms, and automated updates made a world of difference.

• Example 2: Chassis Shortages

For port drayage, chassis availability is always a bottleneck. I learned to build relationships with multiple depots and pre-book equipment during peak seasons. Systems like this prevent last-minute scrambling and keep the operation running smoothly.

Takeaway: The freight is only as reliable as the systems supporting it. You don’t need fancy software to start—simple processes like standardizing how you book loads or track updates can make all the difference.

Lesson #2: Clients Don’t Care About Excuses—They Want Solutions

In logistics, there’s always something going wrong—weather delays, port congestion, missed appointments. But here’s the harsh truth: clients don’t care why something went wrong; they care about how you’re going to fix it.

A relatable scenario:

• Port Delays: A container scheduled for drayage is delayed three days at the port due to customs holds. The client is angry because their warehouse team is waiting. Instead of offering excuses, we began offering alternatives, like transloading onto trucks directly from the port or scheduling partial deliveries. These solutions kept clients happy—even if the delay wasn’t my fault.

What I’ve learned:

1. Be proactive: Notify clients of issues as soon as you know. It’s better to over-communicate than to let them find out on their own.

2. Offer options: Have backup plans ready (e.g., split loads, expedited deliveries, or warehousing).

3. Own the problem: Even if it’s not your fault, take responsibility for finding a solution.

Lesson #3: Not Every Client Is Worth the Work

When you’re starting out, it’s tempting to take any client who comes your way. But not all freight is good freight, and some clients will drain your resources without contributing to your growth.

Signs a client isn’t worth it:

1. They nickel-and-dime you: Clients who haggle over every dollar usually aren’t loyal.

2. Unrealistic demands: If a client expects 2-hour turnaround on loads without paying for expedited service, they’re setting you up to fail.

3. Late payments: Consistent late payments kill your cash flow and make it hard to pay your drivers.

A real example:

I once worked with a client who insisted on paying “within 90 days” but demanded daily updates and extra services for free. I spent hours chasing their loads, but their payments barely covered costs. Letting them go felt risky, but it freed up time and resources to focus on better-paying, reliable clients.

Takeaway: Your business is only as strong as your client base. Focus on clients who value your work and pay fairly.

Lesson #4: Drivers Are Your Backbone—Invest in Them

Finding and keeping good drivers is one of the biggest challenges in logistics. A reliable driver can make your business, while a careless one can destroy it. I learned this the hard way when I had to recover a $250,000 piece of equipment because a driver ignored clear instructions.

What works for me:

1. Fair Pay: Pay your drivers on time and offer competitive rates. They’ll stick with you if they know you value their work.

2. Respect: Treat drivers like partners, not just employees. Simple things like asking for their input on routes or listening to their concerns go a long way.

3. Support: Offer programs that help drivers grow, like becoming owner-operators. My Angel Investor program, for example, helps drivers own their trucks while building my business.

Lesson #5: Cash Flow Is Everything

The logistics business runs on thin margins, and cash flow can make or break you. Early on, I struggled to pay drivers on time because clients were slow to pay me. I quickly realized I needed to tighten up my payment terms and build a cash reserve.

Real examples of cash flow fixes:

• Invoice Factoring: I started factoring invoices to get paid within 24 hours instead of waiting 30-60 days. The small fee was worth the peace of mind.

• Clear Payment Terms: I stopped extending credit to new clients and began requiring deposits for high-risk loads.

• Cutting Costs: I reviewed every expense—from fuel cards to dispatch software—and cut anything that wasn’t adding value.

Takeaway: Cash flow management isn’t just about survival—it’s about creating stability so you can focus on growth.

Final Takeaways

Scaling a logistics business isn’t easy, but it’s possible if you focus on what really matters:

1. Build Systems: Streamline operations so they can handle more volume without breaking down.

2. Solve Problems: Clients will stick with you if you’re proactive and reliable.

3. Choose Wisely: Not all freight or clients are worth your time—focus on quality over quantity.

4. Invest in Drivers: They’re the face of your business, so treat them well.

5. Manage Cash Flow: Keep your finances tight to weather storms and invest in growth.

These lessons come from real struggles, late nights, and a lot of trial and error. If you’re in the trenches trying to scale your logistics operation, I hope this helps you find a path forward.