Josh Hamilton

Choosing the Right Partner: Questions to Ask a Trucking Payroll Service Provider Payroll may not be the most exciting part of running a trucking business, but it’s one of the most important. When drivers are paid accurately and on time, trust builds. When mistakes happen, frustration spreads quickly. That’s why choosing the right trucking payroll service provider isn’t just a technical decision—it’s a strategic one. The right partner can simplify compliance, save time, and support growth. The wrong one can create constant headaches. If you’re evaluating payroll providers, asking the right questions upfront can make all the difference. Below are the key areas you should explore before committing to a long-term partnership. Do they truly understand the trucking industry? This may seem obvious, but it’s often overlooked. Payroll in trucking is very different from payroll in most other industries. Drivers may be paid by the mile, by the load, hourly, or through a mix of incentives and reim...

Why Every Owner-Operator Should Consider a Tax Specialist? Being an owner-operator means independence, flexibility, and control over your business. It also means responsibility—lots of it. You’re not just driving the truck; you’re managing income, expenses, compliance, and long-term planning. Taxes sit right in the middle of all that, and they’re often the most misunderstood part of the job. Many owner-operators try to handle taxes on their own, at least at first. Some do fine for a while. Others don’t realize something’s wrong until a notice shows up in the mail. This isn’t about fear—it’s about realism. Trucking taxes are complex, and the cost of small mistakes can quietly grow over time. Trucking Taxes Aren’t Like Other Small Businesses At a glance, it might seem similar to other independent work. You earn income, deduct expenses, and file a return. But trucking adds layers that most businesses never deal with. Multi-state income, fuel taxes, per diem rules, depreciation schedules, ...

Common Misconceptions About Trucking Tax Services Taxes are one of those topics most truck drivers would rather avoid. Between long hours on the road and running a business, it’s easy to rely on assumptions passed around at truck stops or online forums. Unfortunately, many of those assumptions about trucking tax services are outdated, incomplete, or just plain wrong. Over time, these misconceptions can lead to missed deductions, compliance issues, or unnecessary stress. Let’s clear the air. Below are some of the most common misunderstandings truck drivers have about trucking tax services—and why believing them can cost more than you think. “I Can Just Use the Same Tax Software Everyone Else Uses” This is probably the most widespread misconception. While general tax software works fine for simple W-2 income, trucking taxes are rarely simple. Owner-operators and small fleet owners deal with fuel taxes, multi-state income, depreciation, per diem, and mileage-based deductions that generic ...

Top Questions to Ask a Trucking Tax Specialist Before Hiring Hiring a trucking tax specialist can feel like a big step, especially if you’ve handled your taxes on your own for years. There’s money involved, trust involved, and the quiet worry of choosing the wrong person. Not all tax professionals understand the realities of trucking, and asking the right questions upfront can save you from costly mistakes later. This isn’t about grilling someone like an audit interview. It’s about understanding how they think, how they work, and whether they truly fit your business on and off the road. Below are the most important questions every truck driver should ask before making that decision. Do You Specialize in Trucking or Transportation Taxes? This should always be the first question. Trucking taxes come with industry-specific rules—per diem, mileage logs, depreciation schedules, and fluctuating income streams. A specialist who “also works with truck drivers” is very different from someone wh...