Josh Hamilton

How Tax Specialists Help with Business Entity Setup? Starting a business—especially in the trucking world—is exciting, but let’s be honest, it’s also a little overwhelming. One of the first big decisions you’ll face is choosing how to structure your business. Should you be a sole proprietor? LLC? Maybe an S-corp? Here’s the thing: the business entity you choose doesn’t just impact how you’re seen on paper—it affects everything from your taxes to your personal liability to how much you keep after expenses. This is where the insight of a trucking tax specialist comes into play. While attorneys might focus on legal protections, tax professionals are laser-focused on how your entity type affects your bottom line. And that, in the long run, can be the difference between barely breaking even and building a sustainable, profitable business. 1. Entity Type Isn’t Just About Paperwork—It’s About Profit     There’s no one-size-fits-all when it comes to business structures. Each type—sol...

When You Should Hire a Trucking Tax Specialist? If you're in the trucking world, you know it's more than just hitting the road and delivering freight. Behind the wheel, there’s an entire business to manage—fuel receipts, maintenance costs, compliance paperwork, and most of all, taxes. At some point, even the most independent trucker hits a wall with tax complexity. And that's exactly when hiring a trucking tax specialist can save you time, money, and stress. This article breaks down when it makes the most sense to bring in a specialist, and why waiting too long could be costing you more than you realize. 1. You’re Just Starting Your Trucking Business     Starting as an owner-operator or launching a small fleet? That’s the perfect time to bring in a trucking tax specialist. The early decisions you make—like your business structure (sole proprietor vs. LLC vs. S-Corp), how you track expenses, and how you set up quarterly tax payments—can shape your finances for years. A good ...

Top Questions to Ask a Trucking Tax Specialist Let’s face it—trucking taxes aren’t easy. Between fuel receipts, IFTA, multi-state income, and depreciation on that shiny new rig, the financial side of trucking can feel like a maze. That’s why working with a trucking tax specialist can be a game-changer. But just hiring one isn’t enough—you need to ask the right questions to know if they’re truly equipped to handle the complex world you drive through every day. Whether you’re an owner-operator or run a small fleet, here are the top questions you should ask a trucking tax professional before handing over your books. 1. Do You Specialize in the Trucking Industry?     This one seems obvious, but it’s surprising how many tax preparers take on trucking clients without really understanding the business. A true trucking tax specialist should have experience working with drivers, fleet owners, and transportation companies. You want someone who doesn’t need an explanation for things lik...