As someone on a work visa, how did you quit your job exactly? What's the grace period before you need to find someone else to sponsor your visa? (I'm assuming your startup can't afford to do so, but I may be wrong)
As a Canadian, I may enter the US for up to 6 months at a time without requiring a visa, but am I not allowed to work. So when I do visit, I make sure to only visit friends and I make sure not to do any work. I am currently in Toronto, but next month will be taking a vacation to the USA.
I wonder what is considered "work" and how could it be tracked. Whenever I travel abroad, I bring my laptop, and I always end up answering a few emails and writing code (which is what I do when I go to the office here in the US). If you have a company registered in Canada and you come to the US for 6 months, who is to stop you from sitting at a computer and typing away, as long as no money changes hands in the US?
If you're not going to a common tourist destination for two weeks, have fun at the border.