The W-9 Lesson: How One Business Owner Learned the Hard Way
Meet Jake. Jake is a hardworking general contractor who needed to hire extra hands during a particularly busy summer. He didn’t want to deal with payroll taxes or paperwork, so when his helpers asked how they’d get paid, he said, “You’re contractors. I’ll just write you a check every week.”
Easy enough—or so he thought...
When tax season rolled around in January, Jake’s tax preparer asked him for W-9 forms for all of his contractors so she could prepare their 1099-NEC forms. He hadn’t collected any information for any of them. He had names and phone numbers. Which is not enough.
When 1099 Reporting Kicks In
Here’s the deal: If you pay independent contractors $600 or more during the year (see below for changes to 2026 reporting), you may have to issue form 1099-NEC to report payments for services performed for your trade or business. How do you know who needs to receive a 1099? The IRS guidelines state that if the following four conditions are met, you must generally report a payment as non-employee compensation.
- You made the payment to someone who is not your employee.
- You made the payment for services in the course of your trade or business.
- You made the payment to an individual, partnership, estate, or in some cases, a corporation.
- You made reportable payments to a payee that total the threshold amount or greater during the year. Which is $600 for 2025. (An Important Note: The new $2,000 threshold signed into effect by the OBBB starts in 2026 for payments made after December 31, 2025. Don’t let rumors fool you—keep collecting those W-9s and issue 1099s for $600+ payments this year.)
To correctly issue 1099 forms to your contractors, they will need to fill out a W-9 — the form that gives you their name, address, and taxpayer identification number (SSN or EIN). Jake didn’t know this, so he was missing the one thing he needed most — their tax IDs.
The January Headache
Instead of kicking off the new year with fresh projects, Jake spent hours chasing down contractors. He called. He texted. He left message after message. Some replied right away — but others had new phone numbers, moved away, or just vanished, taking Jake’s peace of mind with them. The IRS 1099 filing deadline was fast approaching, and Jake couldn’t complete half of his forms.
There are two big issues when you pay contractors without getting a W-9:
- Issuing the 1099 — the problem everyone knows about. Without the contractor’s SSN or EIN, you can’t correctly issue a 1099, and the IRS may fine you for missing or incorrect forms.
- Backup Withholding — the problem no one talks about. And this one can cost you money.
The Backup Withholding Trap
Here’s what the IRS expects if you make payments to a contractor that are equal to or greater than the $600 threshold:
- Make sure you have the contractor’s name, address, and Tax Identification Number on a form W-9. This ensures you have everything you need to issue Form 1099.
- If you don’t have the contractors’ Taxpayer Identification Number, you must withhold 24% of their payment and send it to the IRS. This is called backup withholding. This is a very common area of non-compliance. The law (IRC 3406(a)(1)(A)) states backup withholding is required if the payee fails to furnish his Tax Identification Number to the payor.
Let’s put this in Jake’s world. Jake paid one of his missing contractors $1,000 for some deck work. Since he never got a W-9 he should have withheld $240 (24%) and paid the contractor $760. The $240 would have been sent to the IRS. In this scenario, that $240 is not Jake’s money, it was the contractors, and Jake would be paying the tax on behalf of the contractor.
But, here is the bad news. When the IRS reviews Jake’s filings and notices the missing forms or unreported payments, they will assess that tax against Jake, not the contractor. That means Jake could be on the hook for that $240, plus penalties and interest.
The Cost of Procrastination
By the time Jake finally tracked down a few of his contractors, the filing deadline had passed. He ended up filing some 1099s late, paying penalties, and still couldn’t report the payments for the ones who disappeared.
And the worst part? All of it could have been avoided with five minutes of paperwork before cutting that first check.
Jake’s New Rule (It Should be Yours Too)
Now, Jake won’t let anyone lift a hammer until he gets their W-9. His new motto: “No W-9, no pay.” If you pay contractors, learn from Jake’s mistake:
✅ Always collect a W-9
before making the first payment.
✅ If you don’t have one, start backup withholding (24%) AND pay that to the IRS.
✅ Remember, if you skip both, the IRS may come after
you, not the contractor.
Moral of the story:
Paperwork may not be fun, but it’s a whole lot easier than trying to hunt down missing contractors in January.
How can KAC Consulting, Inc. help?
If you would much rather focus on the parts of your job that you love most, or you need help with bookkeeping and compliance, please contact us today and let's see how we can work together!











