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Do I need to send 1099s to all my subcontractors?

You don’t need to send a 1099 to every subcontractor. The rules depend on how much you paid them, how they’re structured as a business, and how you made the payments.

The basic requirement is straightforward. If you paid $600 or more to a subcontractor during the year for services, you generally need to send them a 1099-NEC. Payments below that threshold don’t require reporting. The $600 applies to the total for the year, not per payment. Ten payments of $75 each to the same person adds up to $750, which crosses the threshold.

Corporate status matters. Payments to corporations, both C-corps and S-corps, typically don’t require a 1099. If your electrician runs an S-corp, you don’t need to file one for them. The major exception is payments to attorneys, which always require a 1099 regardless of their corporate structure.

Payment method also changes things. If you paid a subcontractor through a credit card, debit card, or a payment service like PayPal or Venmo, you don’t need to send a 1099. Those payment processors are responsible for reporting through a 1099-K instead. This catches a lot of business owners off guard because they think every payment over $600 needs reporting. It only applies to checks, cash, ACH transfers, and similar direct payments.

The only way to know whether your sub needs a 1099 is to have their W-9 on file. The W-9 tells you their legal name, tax ID, and most importantly, their business type. Get the W-9 before you make the first payment, not in January when you’re scrambling to file. Chasing down W-9s at year end is one of the most frustrating parts of running a business that uses subcontractors. If you work in skilled trades and construction, this is especially important because you might pay fifteen or twenty different subs throughout the year.

The deadline is January 31. The 1099-NEC must be sent to the subcontractor and filed with the IRS by this date. There’s no automatic extension, and penalties for late filing start at $60 per form and increase depending on how late you are. Miss enough of them and the penalties add up fast.

Track who you’ve paid and how much throughout the year. By December, you should already know which subs need 1099s and have their W-9s collected. Waiting until January creates unnecessary stress and mistakes. Small business bookkeepers can set up systems to track payments by vendor and flag anyone approaching the $600 threshold so nothing slips through.

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More Questions

What is retainage and how do I record it in my books?

Retainage is a percentage of each payment that clients hold back until a construction project is complete. In your books, it's recorded as a separate receivable asset that gets collected when the job wraps up.

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What e-commerce expenses are tax deductible?

E-commerce sellers can deduct platform fees, inventory costs, shipping and packaging, software subscriptions, advertising, and home office expenses. The key is tracking expenses properly throughout the year.

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When should I switch from doing my own books to hiring a bookkeeper?

There's no universal trigger point. The signs are usually falling behind on reconciliation, making recurring errors, or spending hours each month on something that pulls you away from actually running your business.

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What forms do I need when I hire a new employee?

Every new hire needs a W-4 for federal withholding and an I-9 to verify work authorization. Virginia also requires a VA-4 for state withholding and new hire reporting within 20 days.

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Can you help me migrate from QuickBooks Desktop to QuickBooks Online?

Yes, we regularly help businesses migrate from Desktop to Online. The process involves transferring your data, cleaning up historical entries, and getting you comfortable with the new system.

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How do I pay myself as a business owner?

The method depends on your business structure. Sole proprietors and most LLCs take owner's draws. S-corp owners must pay themselves a salary through payroll and can take additional distributions.

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