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The answer is very fact specific but depending on how often you come and and how long you stay, almost certainly you will be able to enter the US as a visitor for a period of time. That being said, it might just be easier to get a work status so that you don't have to work how often you come and how long you stay. Do you have operations and employees in Canada as well?

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Thank you for your insight! I'm the only Canadian right now. We're still a small startup. I don't have majority control of the company by myself any more as we have raised VC.

I only enter the States for very specific business purposes and short durations and the occasional short family vacation. Less than 8 weeks in any given year, and much less now that I have kids at home.

I am super qualified for a TN1 computer systems analyst. I could presumably make a case for an O1 but that's a lot of work to prepare.

You really should be fine coming in as a visitor with just your Canadian passport (although consul with an attorney if you're really concerned) and the strategy could be to do this until you get some pushback.

Thank you!

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