Here is another edit from “Dear Sophie,” the advice column that answers immigration-related questions about working at tech companies.
“Your questions are vital to the dissemination of knowledge that empowers people around the world to rise beyond borders and pursue their dreams,” says Sophie Alcorn, a Silicon Valley immigration attorney. “Whether you’re in people operations, founding, or looking for a job in Silicon Valley, I’d love to answer your questions in my next column.
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Dear Sophia:
I am a Canadian citizen working under a TN visa as a software engineer in the United States. I want to start my own business or at least make money from side hustle. Is this possible on my TN, or is this the only way to do this via a green card? If so, is it possible to obtain permanent residency since the TN is for non-immigrants?
— A shrewd Canadian
Dear Clever,
There are many things the modern US immigration system was not designed for, including (but not limited to): Internet, e-filing and blockchain, remote work, home, the modern gig economy, startups, flexible work arrangements and entrepreneur work.
You may know that our current system of laws was generally created by the Immigration and Nationality Law in 1952, when everything was much simpler. The legal story at play here includes judges making rulings on tailors from China sailing to San Francisco to take measurements for suits that would be sewn months later when they return home.
I’ll cut to the chase: you cannot perform work under your TN for anyone other than the employer who sponsored you for TN. So my educational message is this: no hustles or startups on your TN.

Picture credits: Joanna Buniak / Sophie Alcorn (Opens in a new window)
Two TN visas at the same time?
Yes it’s possible. Under immigration law, you can have two TN visas at the same time – one from your current employer and one from another employer; say, your startup. However, this is very difficult to achieve and comes with two very important caveats: