There are basically two ways of becoming a billionaire: by taking risks in a new market, or by eliminating risk in an established market. American billionaires, by and large, tend to do it the first way. Every Canadian billionaire I can think of did it the second way. Neither the size of the Canadian market, nor the Canadian banking or legal system, nor the Canadian culture, encourage people to take risks on the scale required to build new businesses worth billions of dollars.
There's a reason why Elon Musk, after spending several years in Canada, chose the U.S. as the country in which to do business.
When your richest men got that way by avoiding risk, you can expect them to run their toy hockey teams in a similarly risk-averse manner.
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