How to legally work in the US?

The answer will depend on various factors, including the structure of the company, your position/title/duties, your shares, remuneration you are receiving (salary by T-4, contractor (no T-4), dividends, etc.), does the company employee Canadians or permanent residents, profitability of the company, your English test results from a standardized testing organization, e.g. IELTS, CELPIP. A lot of changes have occurred to the management of most immigration applications (Express Entry introduced in January 2015), creating a more competitive and fast paced immigration process. http://www.cic.gc.ca/english/immigrate/express/express-entry.asp The Ontario Opportunities (Provincial Nominee Program) program remains a very good option for recent graduates of Ontario colleges/universities and if you hire an experienced immigration lawyer to strategize and plan the best pathway to immigration, using your company as a catalyst/springboard (applying for Employer Pre-Screen of a Job Offer), you have a high likelihood of success in gaining permanent residence status. http://www.ontarioimmigration.ca/en/pnp/OI_PNPSTUDENTS_JOB.html Keep in mind there are on-going changes and future changes that are to come with the management and processing of immigration applications and there is no 100% way to predict or guarantee how any immigration application will unfold. However, working with an experienced and savvy "think outside the box" immigration lawyer, before any application is submitted, who can prepare and present your application in the most favourable way (knowing how the immigration bureaucracy thinks and what factors will make an application look more promising) and navigate the web of immigration law and policy to avoid delays in processing or refusal, and manage your temporary status as a worker along the way, is key.

I am a bit confused why you are starting a business, but asking how to best monetize it. That is a red flag, at the start. In my experience, when you are starting (or looking to gain more clients), defining a niche is a far better strategy than being a generalist. That said, once you are established, you can expand your service offerings. But at the start, you must be known for something (a niche), otherwise, you’ll be known for nothing. By choosing a niche, you can position yourself as a true expert and give your clients the assurance that you understand their needs, speak their language, and know how to solve their problems. As a generalist, you are likely to be seen as a “Me too!” A widget who can be replaced at any time. Further, a widget often relies on competing on price, as there is no differentiator between you and the next widget. You are interchangeable. Therefore, you must be cheaper than the next widget and a race to the bottom ensues. And be careful, because a race to the bottom is not one you want to win.

I think what you need to do is market analysis. According to Labour Market Outlook, there is cumulative hiring requirements in Canada for ICT talent are expected to be over 182,000 by 2019. I think the number will vary by 10-15%. Having said that, I would suggest you focus on the ICT professionals. You have to design your business model, work on customer value proposition and business risk.

I am from Toronto as well and you can receive money and work remotely for which you have to pay taxes. However in order to go and work there you need a work visa. H1B - H2B etc.

1) Get a job offer from a friend or connection who runs a US business... or... 2) Offer your services at a significant discount to a local worker. Work visa is the fastest, easiest way. Still not easy, but better than marrying someone for a visa.