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I'm a software engineer with US citizenship and will be relocating to Ireland under a skilled workers Visa. I will be bringing my family with me. Currently in addition to day job I'm involved in a small startup which compensates me in cash and equity.

I would like to maintain my position in my startup and continue to be compensated.

Is it legal for me to do so? If not what could I do to maintain both jobs?

Some of the options I've been trying to look into, but have not found any concrete info are:

  1. Just work for both companies and pay my taxes.
  2. File a US LLC and operate my startup though that.
  3. Create an Irish company and operate through that.
  4. Making my spouse the head of a small company of which encapsulates my startup work.
  5. Create an Irish company, hire myself as a contractor and pay for a second visa/permit.

Note: I'm not looking to avoid taxes/etc. I'm more interested in everything being square with Irish/EU/US policy as I am planning on this relocation being permanent.

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Just after relocation on high skilled visa, you'll have Stamp 1. That's basic immigration status. Your spouse will have Stamp 1G or Stamp 3 (depending on some regulations). All those stamps (1, 1G, 3) don't allow you or your spouse starting a company or being a contractor in Ireland. So options 3,4,5 violate your both immigration status.

Options 1 and 2 don't violate your status, but you will need to file for double taxation avoidance to Irish and US tax services. I have a couple American colleagues, they do so.