Harley Finkelstein wants Canadian entrepreneurs to ignore the “bullshit”

Harley Finkelstein Shopify president on The BetaKit Podcast
Shopify president cautions against doom-and-gloom narratives and founder mental traps.

Back in May, BetaKit hosted a town hall where Shopify CEO Tobi Lütke noted that ambition is a problem in Canada’s “go-for-bronze” culture.

The point resonated with many founders across the country, but I’m not sure if ambition is the sole problem.

“Using Canada as an excuse for why you didn’t get funding, you didn’t get to hire the right person … I think that’s bullshit.”

Currently, we have: entrepreneurs threatening to leave Canada due to a high cost of living and Budget 2024’s capital gains tax rate changes; Canadian angels saying those tax rate changes are killing their investment pipeline; and we’re in the middle of the worst year for VC fundraising in a decade according to BetaKit’s Josh Scott, who has reported on whispers of emerging VC’s quietly leaving the space as they fail to close funds.

It’s a sharp about-face for the brand of Canadian entrepreneurship compared to say… 2016. But is the doom and gloom legit or just another spin of the wheel in an ongoing cycle?

On the podcast this week, we have Shopify president Harley Finkelstein, someone personally and professionally invested in the state of entrepreneurship, and one of the more doggedly optimistic people I know.

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I ask Finkelstein if the above issues are core problems or if we’re simply in need of a brand refresh, and it’s interesting which side of the line he falls depending on the subject. Some highlights from Harley on this episode for Canadian founders:

  • Be proud of being Canadian.
  • Be less Canadian.
  • Stop comparing Canada to the US.
  • Start thinking and acting on a global scale.

The advice can seem contradictory and perhaps a little hard to swallow if you’re an early-stage entrepreneur. The fact that the Québec venture ecosystem is “highly dependent” on public funding is below Shopify’s stratosphere, but very real for first-time founders, emerging managers, and even some of the entrepreneurs Finkelstein mentions by name on the podcast (almost all of whom are 10 years or more into their entrepreneurial journey).

But here’s the thing: on the whole, Finkelstein is correct in his proclamations, and the complexity lies in understanding the proper calibration for each truism. He seems most interested in busting Canadian founders out of any mental trap holding their company back; for everything else, flavour to taste.

So does the president of Canada’s largest tech company really think we’re being too Canadian? 

Let’s dig in.


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The BetaKit Podcast is hosted by Douglas Soltys & Rob Kenedi. Produced & edited by Jess Schmidt. Recording support for this episode graciously provided by AmberMac Media.

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