Harley Finkelstein on anxiety
From Shopify’s Harley Finkelstein is an Anxious Achiever · · Morra Aarons-Mele
“When I'm preparing for something that's really important, the IPO for example, or an earnings call for example, or negotiating a very important business deal, I actually don't need to activate the parasympathetic nervous system. I actually want to use some of that anxiety to anticipate all the things that could go wrong, not because I want to bring my anxiety or transfer it to them, but because it provides me with this incredible checklist of things that most people would never think about.”
On , Harley Finkelstein, President at Shopify, spoke about anxiety during Shopify’s Harley Finkelstein is an Anxious Achiever on Morra Aarons-Mele.
About Harley Finkelstein
Harley Finkelstein, President of Shopify, discussed the company's Q1 2026 earnings in several May 2026 interviews. He noted that Shopify reported $3.17 billion in revenue, up 34% year-over-year, with free cash flow of $476 million and its second consecutive quarter of over $100 billion in gross merchandise value. Finkelstein described the quarter as "incredible strong growth" and highlighted that Shopify now accounts for 14% of U.S. e-commerce. He emphasized that the company is "at the epicenter of the AI era," citing that orders from AI-powered searches to Shopify are up 13x year-over-year and that Shopify is the only platform powering selling inside ChatGPT, Microsoft Copilot, and Google. He also discussed Sidekick, Shopify's AI assistant for merchants, which he said has seen 4x year-over-year usage growth. Finkelstein stated that AI is "making entrepreneurship dramatically more accessible" and predicted that "more billion-dollar brands" will be built from scratch in the next five to ten years. In other appearances, Finkelstein spoke about his personal side business, Fire Belly Tea, a tea company he co-founded with former Shopify COO David Siegel during the pandemic. He also addressed antisemitism in Canada, saying that what some call advocacy is "unequivocally antisemitism" and that the current moment requires Jews to "be loudly and proudly Jewish." He expressed optimism under Prime Minister Mark Carney compared to the previous government. Finkelstein also participated in a game identifying real and fake Shopify products, correctly guessing various niche businesses while acknowledging his familiarity with many of the merchants on the platform.