📱 Best Platforms
Upwork (1099 preparation and contractor payment tracking jobs during tax season), Fiverr (1099 form preparation and filing gigs), LinkedIn (pitch agencies and small businesses who hire multiple freelancers — they all need 1099s filed by January 31).
📖 The Hustle
Agencies and small businesses that pay freelancers, contractors, and vendors over $600 must issue 1099-NEC forms by January 31 each year or face IRS penalties. Most wait until January and scramble. You compile contractor payment records, verify W-9 information, calculate totals, prepare 1099-NEC forms, and e-file them. Charge $15-25 per 1099 or $200-500 for a batch of 20-30 during tax season.
🚀 First Step
Download a blank 1099-NEC form from the IRS website, study the fields and filing requirements, and practice filling one out with sample contractor payment data.
🔑 Keys to Success
- Start reaching out to clients in November for January 1099 season — the early pitch lands because their stress hasn't peaked yet.
- Require a completed W-9 from every contractor before you prepare their 1099 — chasing missing tax IDs in January is the worst part of the job.
- Use Tax1099.com or Track1099 for e-filing — paper filing is slower, more error-prone, and clients expect electronic filing now.
🛠 Tools & Resources: QuickBooks Online, Tax1099.com, Track1099, Google Sheets, IRS.gov