Entrepreneurial ecosystems: Reflections on Toronto and Silicon Valley

On May 26th, I attended the C2 conference in Montreal, joining my good friend Harley Finkelstein (Shopify), along with Magaly Charbonneau (Password Box), Wesley Chan (Felicis) and Eric Boyko (Stingray) on a panel. The theme was: “Entrepreneurial ecosystem: it takes a village to build a startup”.

Harley asked about my experiences growing up in Toronto and moving to Silicon Valley, specifically what my thoughts are on the differences between the two communities.

It’s an interesting question and one that I’m asked quite often. In fact, I touched upon the subject in a reflection I wrote last year on Building startups and collective ambition outside Silicon Valley”. When discussing regional and cultural differences, it’s hard to not overgeneralize, but here’s what I shared during the panel.

Culture, harmony and outliers

Canadians tend to be harmonious and neutral. We apologize for everything. We aren’t extreme and aim to get along. This is quite different from the US where things seem more polarized. While living in Silicon Valley (which has a more capitalistic culture), I’ve had the privilege to meet some the smartest, most brilliant, most ambitious, and generous people. But there’s also a huge disparity in wealth, education, etc. There are countless people on the other end of the spectrum who have not had the same opportunities, feel disenfranchised and are a stark contrast to the American Dream.

So what do these culture differences mean for entrepreneurship when winners are usually outliers? It doesn’t pay to be average or play it safe.

I believe that there are opportunities for both ecosystems to improve, albeit in very different ways. For Canadians, we need to be bold and think on a bigger stage. For SV, we need to think about how we can build and use technology to democratize knowledge, improve access to healthcare for all, and create a fairer distribution of wealth.

Culture and diversity

For Toronto (and most of Canada), diversity is our nation’s identity and pride. It is the quality that unites us. It is a great strength that introduces us to different perspectives and experiences, while teaching us tolerance and inclusion. On the other hand, SV is quite homogenous when it comes to diversity of thought (i.e. there’s a lot of “groupthink” with everyone being in tech). As a result, here, diversity is a way that individuals can stand out from the crowd.

For an analogy on how the two nations embrace diversity: just think about their birthdays. The differences are quite clear: Canada Day celebrates confederation, and July 4th celebrates Independence Day.

What are the implications for entrepreneurship? We already know that diverse companies and teams perform better and the recent events have put tremendous pressure on Silicon Valley (and all of us, for that matter) to be more aware and purposeful around the cause. On the flip side, Canadians should be more aggressive in embracing this advantage to gain some ground!


As you can see, these are very general observations made during a panel discussion. I’m deeply entrenched in both ecosystems. It’s not my place to say that one is better than the other, especially when I truly love both. But by appreciating the differences, we can learn and grow each ecosystem to cultivate more success for all.

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