Backed by Y CombinatorThree documents and three sheets that track every contractor payment against the one thing that actually blocks a January filing.
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What you get
Pack of 6 files: 3 documents, 3 spreadsheets
RegisterLarkspur Renovations. Every contractor, and whether the W-9 came in before the first payment.
| Contractor | Trade | W-9 status |
|---|---|---|
| Devon Ashcroft | Electrician | On file |
| Marisol Pena | Plumber | On file |
| Reyes Drywall & Paint | Drywall, paint | On file |
| Tobias Lund | Landscaper | Missing, chased twice |
| Priya Nair Bookkeeping | Bookkeeping | On file |
| Wyatt Combs | Handyman | Not collected |
Totals| Contractor | Payments | Total paid |
|---|---|---|
| Reyes Drywall & Paint | 4 | $11,900.00 |
| Devon Ashcroft | 3 | $8,400.00 |
| Marisol Pena | 2 | $6,150.00 |
| Priya Nair Bookkeeping | 12 | $3,600.00 |
| Tobias Lund | 2 | $2,450.00 |
| Wyatt Combs | 1 | $1,150.00 |
| Total | 24 | $33,650.00 |
Filing| Contractor | Clears $2,000? | W-9 on file | Status |
|---|---|---|---|
| Devon Ashcroft | Yes | Yes | Ready to file |
| Marisol Pena | Yes | Yes | Ready to file |
| Reyes Drywall & Paint | Yes | Yes | Ready to file |
| Tobias Lund | Yes | No | Blocked |
| Priya Nair Bookkeeping | Yes | Yes | Ready to file |
| Wyatt Combs | No | No | Not required |
One contractor of six is blocked heading into January, and it is the one who never had a W-9 collected.
A free 1099 template online is usually nothing more than a blank form and a due date. It does not say which of this year's contractors actually clear the reporting threshold at all, and it says nothing about the specific failure that shows up every January. A contractor cleared the threshold months ago, with no W-9 anywhere in the file, and is no longer answering the phone.
Larkspur Renovations, invented for this pack, paid six different contractors $33,650 combined this year. For payments made in 2026, the IRS reporting threshold for Form 1099-NEC is $2,000 per contractor, up from $600 for payments made before 2026, so five of the six clearly need a form this year. Four had a signed W-9 on file before their first payment ever went out. The fifth, a landscaper paid $2,450 across two spring jobs, did not, and heading into January he is still not responding to requests for one.
Form 1099-NEC carries a single January 31 deadline for both the contractor's copy and the IRS copy, unlike Form 1099-MISC's split schedule, which in practice leaves no later date to fall back on once the form is actually due. Pair this with the owner pay and distribution pack for the separate question of what the business itself pays its own owner. The expense and receipt organization pack covers this same missing-documentation problem, worked through once more on the expense side of the ledger.
The IRS's own three-factor test for contractor versus employee status, applied to each of this year's six contractors by name.
The one rule that prevents the January problem: collect the signed W-9 before the first payment, while the leverage still exists.
The $2,000 reporting threshold, the January 31 deadline for both copies of Form 1099-NEC, and what each Filing Tracker status actually means.
Every contractor with their trade, first payment date, and whether the W-9 came in before or after that first payment went out.
Every payment to every contractor, running toward the total that decides whether the $2,000 threshold is cleared for the year.
Each contractor marked ready to file, blocked on a missing W-9, or not required, so the one entry that needs work is never buried.
Take the blank Word and CSV files with no account, or install the pack in River and hand it your own contractor payment records.
Check each new working relationship against the three-factor test, so the register only ever holds workers who are genuinely contractors.
Ask for it while the relationship is active and the money has not yet moved, not after the job is finished and paid.
The threshold check and the W-9 check run automatically against Payment Totals, so the one blocked contractor is visible months before the deadline.
Yes. Three documents and three sheets download as Word and CSV files with no signup and no credit card. Edit with AI is the optional path where the agent builds the tracker from your own contractor payments. The rest of the library is at the template index.
Word documents (.docx) for the Classification Note, Onboarding Requirements and Filing Procedure, and CSV (.csv) for the Contractor Register, Payment Totals and Filing Tracker. They open natively in Word, Pages, Google Docs, Excel, Numbers and Sheets.
$2,000 per contractor for the year, for payments made in 2026. It was $600 for payments made before 2026, and the amount is scheduled for inflation adjustment in years after 2026, so it is worth rechecking annually rather than assuming it holds.
Keep the request in writing and dated, and treat it as an active filing risk rather than routine follow-up once the contractor has cleared the reporting threshold. This pack does not cover backup withholding mechanics; an accountant can confirm the specific obligation once a W-9 is genuinely refused.
No. The payment still belongs on the Payment Totals sheet, because a second job later in the year, or next year, can push the same contractor over the threshold without warning if the running total was never kept.
It applies the IRS's own three-factor test and shows how this pack's worked example checks out. A genuinely close call on your own working relationship is a facts-and-circumstances question for an accountant or employment attorney, not something a template can settle on its own.
Written by
Co-founder & CEO, River
Chandler has spent the last six years working in AI, building tools for millions of users and Fortune 100 companies. In 2025, he co-founded River to build a new kind of operating system for AI agents.
Download the blank pack as Word and CSV files, or open it in River and have it build your own filing tracker from your payment records.
Edit with AI