W9 Collection Strategy - Tax Season 2025
Context
As the owner of gMoney LLC, I need to collect W9 forms from all contractors paid over $600 in 2025 to issue 1099s. Standard practice is to collect W9s before payment, but I'm doing this retroactively.
Approach
Phase 1: Pilot (December 2025)
Send W9 requests to 3 contractors I'm comfortable with to test the process and messaging:
- McKenna ✅
- Arielle ✅
- Johnny✅
- Sam ✅
- Russ ✅
Goal: Get comfortable with the process, refine the email if needed based on responses, build confidence before broader outreach.
Phase 2: Full Outreach (Early January 2026)
Send W9 requests to all remaining contractors. Having done the pilot, this should feel routine.
- Barbara Hastie ✅
- Brooke Joy ✅
- Denise Mitchem ✅
- Samuel Armes ✅
- Sophia Sunaga ✅
Timeline
| Date | Action |
|---|---|
| Dec 11, 2025 | Send pilot emails to McKenna, Arielle, Johnny |
| Dec 11-31 | Collect responses, note any friction or questions |
| Early Jan 2026 | Send remaining W9 requests |
| Jan 31, 2026 | Deadline to file 1099s with IRS |
Notes
- Attach blank W9 to each email
- Track who has responded
- Follow up gently if no response within a week