W-2 (employee) vs 1099 (contractor): the most-litigated classification question in US labour law.
W-2 is correct when:
- You direct how, when, and where the work happens
- You provide tools and training
- The relationship is ongoing
- The worker doesn't have other clients
1099 is correct when:
- The worker controls how and when they do the work
- They have a real independent business with other clients
- The relationship is project- or outcome-based
- They invoice; you don't issue paystubs
Misclassifying a W-2 employee as a 1099 contractor (the most common founder mistake) exposes you to back-taxes, penalties, and personal liability for unpaid Social Security/Medicare contributions. California's AB5 is the strictest; most other states use the IRS's "common-law" test. Err toward W-2 when in doubt.
State payroll registration: every state where you have a W-2 employee requires separate registration (state withholding tax, unemployment insurance, sometimes paid family leave). This is the part founders skip. Tools like Gusto ($40/mo + $6/employee), Rippling, or a PEO like Justworks handle multi-state registration as part of the service.
Founder salary timing: US Delaware C-corp founders typically start drawing salary once revenue or funding lands. Below that, founder loans (advances) or simply not paying yourself is normal. Once on payroll, you're a regular W-2 employee.