The second you make money. If you are doing personal sales then the expenses can only be deducted up to the amount of income. It's treated as a hobby. You're still supposed to report the amount on the 1099-K but it can never be a negative number. At best it zeroes out with the cost of the items that you sold.
If your intention is to make money though then it is a business the second you start earning. Then you would enter all of your sales as income and deduct all of your costs. If you end up with a negative number then you lost money this year.
If you are losing money at a business for three years then the IRS considers that a hobby.
@2025taxman
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