Harley Finkelstein

Written By Jonah Platt

On Entrepreneurship, Antisemitism in Canada,
and the Responsibility of Being a Jewish Public Leader

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He's worth hundreds of millions, runs one of Canada's most powerful companies, and he still gets antisemitic replies every Friday when he posts “Shabbat Shalom,” here's why he refuses to stop.

Shopify President Harley Finkelstein joins host Jonah Platt for a wide-ranging conversation about Jewish identity, antisemitism, entrepreneurship, and legacy. Finkelstein, a grandson of Holocaust survivors whose family fled Hungary during the Soviet crackdown of the 1950s, opens up about why he has grown increasingly vocal as a public Jewish figure in Canada, especially in the wake of October 7th. He recounts two pivotal incidents that motivated his public advocacy: protesters storming his Big Shot podcast recording at Startup Fest, and demonstrators disrupting his speech at the opening of the Finkelstein Chabad Center in Ottawa. He discusses his relationship with Canadian Prime Minister Mark Carney, Shopify's massive e-commerce footprint (14% of all U.S. e-commerce), and his journey from being one of Shopify's first 136 merchants to its president. He also digs into Big Shot, his podcast with David Siegel that archives the stories of legendary Jewish entrepreneurs, from Charles Bronfman to Jeffrey Katzenberg, arguing that grit is the defining trait behind Jewish entrepreneurial success.

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