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I'm interested in building a web app where users are paid a percentage for their content, and I'm wondering where to start. I have no issues with aspects of making payments to users, and gathering the data necessary to know what I owe them. I'm more interested in the less obvious details, like the following:

  • At what point (or dollar amount) do I need tax info from users?
  • What regulating bodies in the US and/or Canada would I have to answer to?
  • Are the earnings I pay to my users still considered taxable income for me?
  • Would incorporation simplify or complicate this structure?

Obviously, a lawyer would be a good thing, but given it would initially be a side project, I'm just wondering what I would need to know to even get started. To make matters potentially worse, I am based out of Canada and would like to be able to pay U.S. residents as well as Canadian.

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If it is only a small number of users within a single jurisdiction, why not have a passthrough structure (where taxes are the responsibility of the recipients?) – drllau May 16 at 19:31

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