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WinniePaws
Sitter Tax Guide
WinniePaws · SC & NC Pet Sitting

Sitter Tax Guide

What every WinniePaws sitter should know about 1099s, independent contractor status, and where to find your tax documents.

As a WinniePaws sitter, you're an independent contractor, not an employee. That means WinniePaws doesn't withhold taxes from your earnings — you're responsible for reporting and paying your own. This page covers the essentials; for anything specific to your situation, always check with a qualified tax professional.

You're an independent contractor

WinniePaws does not withhold federal or state income tax from your earnings — that's different from a traditional job. You're responsible for reporting all WinniePaws income on your own federal return (Schedule C) and your South Carolina or North Carolina state return.

You may also owe self-employment tax (15.3%, covering Social Security and Medicare) if your net WinniePaws earnings are $400 or more in a year. If you expect meaningful income through the platform, consider making quarterly estimated tax payments to the IRS to avoid underpayment penalties.

Do you get a 1099-NEC?

A 1099-NEC is the tax form that reports your WinniePaws earnings to the IRS. Whether you receive one depends on how much you earned and which tax year it is:

Tax yearForms issuedYou get a 1099-NEC if you earn
2025January 2026$600 or more
2026 and onwardJanuary 2027+$2,000 or more (adjusts for inflation each year after)
The threshold only affects whether we're required to file a form for you — it doesn't affect whether your income is taxable. All WinniePaws earnings must be reported on your tax return, even if you're under the threshold and never receive a 1099-NEC.

Expenses you may be able to deduct

Many pet sitters deduct business-related expenses from their WinniePaws income. Keep records throughout the year — a tax professional can tell you what actually applies to your situation:

  • Mileage driven to and from bookings (IRS standard rate)
  • Pet supplies purchased specifically for bookings
  • A reasonable percentage of your phone bill
  • Liability insurance premiums

Finding your tax documents in Stripe

WinniePaws pays sitters through Stripe Express — that's also where your 1099-NEC and full payout history live.

  1. 1Log in to your Stripe Express dashboard at express.stripe.com
  2. 2Go to Tax Forms to view or download your 1099-NEC (available once WinniePaws files, typically in January)
  3. 3Go to Payouts for your complete earnings history, any time of year — useful even if you don't get a 1099
  4. 4Go to Settings → Personal Information to update your legal name, address, or Social Security Number

Watch for an email from Stripe each November asking you to confirm your tax information — that's a normal part of the process, not spam.

Frequently asked questions

WinniePaws provides this information for general awareness only. We are not tax advisors and this is not tax advice. Please consult a qualified CPA or tax professional for guidance specific to your situation.