The Hard Part with Evan McCann Harley Finkelstein from Shopify
27 snips
Jun 17, 2025 
Harley Finkelstein, President of Shopify, shares his journey as the chief storyteller of the e-commerce giant. He emphasizes the need for ambition in Canadian entrepreneurship, shifting away from cultural modesty. The discussion highlights Shopify's decision to go public and the importance of fostering supportive networks for entrepreneurs. Harley advocates for a culture that embraces innovation and recognizes the challenges faced by startups, while also exploring the significance of passion and purpose in business.
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Canada's Tall Poppy Syndrome
- Canadians tend to downplay achievements due to politeness and tall poppy syndrome.
- Lack of recent Canadian role models reinforces a cultural reluctance to boldly showcase success.
Shopify’s Early IPO Journey
- Shopify went public in 2015 to build trust and allow investors to share in growth.
- Being public was part of a long-term vision to become a trusted, century-lasting company.
Think Long-Term In Product Strategy
- Use a long-term view to build products that serve all customers from startups to large enterprises.
- Resist chasing short-term profits by focusing on scalability and merchant continuity on your platform.