"""The idea of being an entrepreneur, in the GTA especially, is buying a second house in the suburbs and hoping the housing market continues rising.""" ... or

"""The idea of being an entrepreneur, in the GTA especially, is buying a second house in the suburbs and hoping the housing market continues rising.""" ... or a condo to put on Airbnb. You are definitely onto something when you say that there are some deep cultural issues within Canada; Look at RIM, the company believed that its central business customers cared more about security and efficient communication and that the iPhone presented no threat to them. The iPhone was just a crazy idea to them, who would want to use that clunker with a horrible battery life and browse the net on it? Canada has talent, without a doubt, but it also keeps people subdued as you stated because they are constantly questioned by everyone else. Canadians are a lot like accountants, they want to buy that fancy Harley and take it out on the road and live a little, but only on the weekends. :)