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Unapologetically Jewish

Unapologetically Jewish

Harley Finkelstein: Why Being Unapologetically Jewish Matters Now

Aug 24, 2026 · 46m

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About this episode

Harley Finkelstein says the advice to Jewish Canadians right now is brutally simple: stop pretending this is a vibe and start naming what is happening. The Shopify president, entrepreneur, and Big Shot co-host opens up about why October 7 changed the cost of being publicly Jewish - and why he refuses to let fear decide the future of Jewish life in Canada. Raised as the grandson of Holocaust survivors and the son of immigrants, Harley built his life around hustle long before he became one of Canada’s most recognizable business leaders. In this conversation, he traces that drive from a 13-year-old DJ business to co-building Shopify with Toby Lutke, and explains why his identity as a proud,…