Harley Finkelstein: Why Being Unapologetically Jewish Matters Now

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, visible Jew is now inseparable from his public voice.You’ll hear Harley break down:why he thinks a principle only matters if it costs you somethinghow Big Shot turned from a celebration of Jewish entrepreneurship into an archive of Jewish resiliencethe uncomfortable reality behind the latest data on antisemitism in Canadawhy “plan B” conversations are reshaping Jewish life across the countrywhat it means to stay, fight, and build when others are leavingHe also shares the personal side of the story - from putting on tefillin in the middle of law school, to watching his family be targeted publicly, to why he and his wife chose to build a Jewish center in Ottawa rather than retreat. This is a conversation about leadership, courage, identity, and the price of visibility.Essential listening if you care about Jewish life in Canada, the responsibility that comes with influence, or what it takes to stay unapologetically yourself when the pressure to go quiet is getting louder.The Big Shot Podcast - https://open.spotify.com/show/1kk0MtA697RceL9VCa3nUX?si=71829e6f53214477