LLC vs Sole Proprietor for Roofing Sales Reps

You close a big roof, the commission check hits, and somewhere in the back of your head a question keeps nagging. Should you set up an LLC, or just keep filing as a sole proprietor like you have been? Maybe another rep on your crew formed one and now you&

What Is an S-Corp, and When Do 1099 Reps Look Into One

You close a big month, the commission check hits, and then tax season rolls around and you find out how much of it belonged to the IRS all along. If you're a 1099 roofing sales rep, that sting is your self-employment tax showing up. Somebody at the

What Is a SEP IRA? A Guide for Self-Employed Reps

You close a big month. The check clears, the truck payment's handled, and there's real money sitting in your account. Then the same thought hits every 1099 guy sooner or later. Where's this money supposed to go so future-you isn't still

1099 vs W-2 Roofing Sales: The Tax Differences

Two roofing sales reps close the same number of deals in the same year and bring home the same gross commission. One of them files as a W-2 employee. The other files as a 1099 contractor. Come April, one of them owes way more than the other, and it

The Home Office Deduction for Field Sales Reps

You're on rooftops all day, in the truck between appointments, and in customers' driveways closing deals. So when somebody mentions a home office deduction, your first thought is probably "I don't even have an office." You work outside. How does a guy who

Quarterly Estimated Taxes: A 1099 Rep's Overview

If you sell roofs on commission, nobody is holding taxes out of your checks. That check that hits your account is the full number, and it feels great. Then April shows up and the government wants its cut, all at once, and now you're staring at a bill

How to Set Up a Separate Tax Account for Commission Income

Here's the trap almost every commission rep walks into. You close a monster month, the check hits, and every dollar in that account looks like yours. It isn't. A chunk of it belongs to the IRS, and they're going to come collect whether you

Mileage vs Actual Vehicle Expenses for Sales Reps

If you're running a roofing route in your own truck, that truck is a rolling tax deduction. Most guys I talk to know that much. What they don't know is that the IRS gives you two totally different ways to write it off, and picking the

What Is a 1099-NEC? What to Expect at Tax Time

You crushed it last year. Big months, fat commission checks, the kind of season that makes you feel like you finally figured this whole thing out. Then a little form shows up in your inbox or mailbox in January, and suddenly your stomach drops. That form is a 1099-NEC.

Is Your Truck a Tax Write-Off? What 1099 Reps Should Know

You live in your truck. You drive it to inspections, to supplier runs, to that one neighborhood where the last storm dropped hail the size of golf balls. So it makes sense to wonder if all that driving is buying you a break come tax season. Here's the

Tax Write-Offs Roofing Sales Reps Should Know About

Every roofing sales rep I talk to has the same reaction the first time they see their tax bill. Shock, then a little bit of anger. You made great money, you worked your tail off, and now the government wants a huge slice that nobody warned you about. Here'

How to Decide Which Debt to Pay Off First

You've got a truck payment, a couple of credit cards, maybe a personal loan hanging around. You've finally got some money to throw at the pile. So which one do you kill first? It's a question that stops a lot of roofing sales reps