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I run a small business and am looking to pay some people to assist with sales as contractors. They would be paid via something like paypal, google or square. Do I still need to file a 1099 for each person paid over $600? Or would I just record the amounts paid as a single deduction when the time comes?

I'm trying to determine how much book keeping I would need to do at this point.

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You have to file and issue each one of them a 1099 if you are paying them $600 or more for the year.

Because you need to issue a 1099 to them (so they can file their own taxes), I don't think there's a way that you could just combine all of them.

Additionally, you may want to make sure that you are properly classifying these people as contractors in case they should be employees.

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    Important exception: You do not need to issue a 1099 for corporations. So if any of these people are doing business as an S-corp, C-corp, or LLC, you don't need to submit a 1099 for them.
    – Ben Miller
    Commented Jun 4, 2015 at 1:39
  • @BenMiller, great point, yes. What I wrote applied to paying individuals.
    – briantist
    Commented Jun 4, 2015 at 1:40

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