I've actually just gone through this process. I'm a Canadian who just finished school and here are the option my US-based immigration lawyer laid out for me:
1) E2 investment visa: not easy to do. You need to meet an undefined "minimum investment criteria" which is typically $500,000 but if you're lucky you may be able to get in with less.
2) TN-1. A legitimate option for Canadians and Mexican. You need to find an American to own your startup in the U.S. and you start a company in either Mexico or Canada. You then get hired by the owner of the U.S.-based company and get a TN-1. You can't be the owner of the U.S.-based company but you can have an option to buy the whole thing.
The nice part about this is that you then get the American-based company to issue you an H1-B visa the next year and you're well on your way to a Green Card.
3) L2. Find someone on an L1 visa and marry them. You can then work for anyone in the U.S. including your own company
As a Canadian, don't you just need the citizenship card to get in America? The borders are pretty much open, so I wouldn't be surprised if that were the case.
Thats if you want to spend money in America. I grew up on the border and even worked a short stint in customs. They can be right anal if they think you're actually do anything productive. Could've just been the fine folk in Montana. Tight squinting eyes boring through your soul. Fingers rapping gently over the grip of their pistol. Waiting and watching you as a stillness fills the air, offering you no escape. "You boys ain't look'n at taki'n jobs from good 'merican boys now are ya?"
As someone mentioned, you can 'visit' but I'm not sure how well that'd work overall. Boston is a 5 hour drive from Montreal. If I recall correctly YC has funded outsiders before. I would be very interested to hear how they managed.
I think Y Combinator would be an amazing experience that I wouldn't get anywhere else. I'd be more than willing to give up several months of my life to move to a new country to learn and work with amazing people. The question of the border is the biggest stumbling block in the path.
I've actually just gone through this process. I'm a Canadian who just finished school and here are the option my US-based immigration lawyer laid out for me:
1) E2 investment visa: not easy to do. You need to meet an undefined "minimum investment criteria" which is typically $500,000 but if you're lucky you may be able to get in with less.
2) TN-1. A legitimate option for Canadians and Mexican. You need to find an American to own your startup in the U.S. and you start a company in either Mexico or Canada. You then get hired by the owner of the U.S.-based company and get a TN-1. You can't be the owner of the U.S.-based company but you can have an option to buy the whole thing.
The nice part about this is that you then get the American-based company to issue you an H1-B visa the next year and you're well on your way to a Green Card.
3) L2. Find someone on an L1 visa and marry them. You can then work for anyone in the U.S. including your own company