Entrepreneurial ecosystems: Reflections on Toronto and Silicon Valley

By Angela, May 31, 2017

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.

  • Vimarsh Karbhari

    Having moved from SV to Toronto last year and being in this space a few observations:
    1. SV has a deep focus on ownership as it gives out stock has you are able to grow the startup. Canadian tax implications make it very difficult to do so. Without ownership and shared responsibility towards growth it is difficult to build an ecosystem here cause startups are hard in general.
    2. I feel diversity is necessary in thoughts. It helps gain alternative viewpoints on a problem. Canada has a lot of it which tends to help. I agree with your view on culture and diversity. Having an alternate viewpoint is important but constructive only when the team has focus on the same goals which is difficult because of 1.
    3. Most of New Grads in computer science (Graduate who are Canadian Citizens) opt to work in the US after graduation. This causes brain drain which is detrimental to startups. Immigration is easier but it does not help fill the void as best talent leaves the country.

  • atkingyens

    Good to read your observations as someone who has done the reverse move 🙂 Thanks for sharing!

  • Jon Zwickel

    Your insights are very thoughtful. My sons and I were born in the US, moved to Vancouver a number of years ago, hold dual citizenship and have never missed voting in an election in either country. I remember taking a trip to Israel with them when they were teens. Even though I’ve been an activist since the 60’s, the decision to buy Canadian flags to sew on our back packs was strange for me. The thought of feeling safer being identified as a Canadian was new back then, but I’ve become proudly so – especially since last Nov. 8. While both countries have nurtured and supported my entrepreneurial spirit my entire life, I’m more at home here. Your comment about confederacy vs. independence summed it all up. Thanks!

  • Thank you for this post. It’s always encouraging to hear people in the industry talk about the lack of diversity in venture. I attended a conference a couple of months ago in San Francisco where Mitch and Freada Kapor of Kapor Capital gave a very compelling, hour long talk on this very topic and what they’re doing to help improve it. Conversations like theirs and posts like yours are evidence that, albeit slow, thigs are moving in the right direcion.

  • atkingyens

    We’ll get there as long as we aren’t complacent 🙂

  • atkingyens

    Thanks for sharing your story, Jon! And glad that the Canadian flags sewn on your packs are now legit 🙂

  • Ian Nichol

    I’d separate problem identification, solutions and execution into different buckets. Diversity likely helps in each. “Canadian politeness” can get in the way of executing on new ideas. (Toyota can run a very polite factory but that is different than rapidly expanding & building..)

    4 things delay execution
    – Priorities (if you have 100 ‘priorities’ you will achieve nothing, true for individuals & orgs)
    – Alignment (a team’s progress slows if someone wants to improve UX & someone else wants to reduce hosting costs)
    – Specificity (‘improve’, improve what? clarity is key)
    – Resources (money, talent, technology, partners)

    I am a Canadian but I have also worked with US teams.
    Priorities – Being ‘nice’ sometimes means we are too wishy-washy to narrow down priorities, everyone’s little project makes the list

    Alignment – we are so ‘nice’ we let people pull in opposite directions

    Specificity – everyone has difficulty with this. When building something new it is tough to describe exactly what will work. Nailing down the next step forward speeds things up. (Agile vs. Waterfall highlights this)

    Resources – Canadians seem to have a bigger loss aversion bias than Americans… Money likes to play it safe. In my own circle the top tech talent is often 1-gen and values the stability of job over the chance to make it rich.

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