Harley Finkelstein (Shopify) - Building a 100-Year Company & the Future of AI Commerce
On this episode, Shopify President Harley Finkelstein joins us to unpack:
- Why Harley says entrepreneurship is "the greatest equalizer," and how watching his refugee father and his grandfather's egg stall shaped how he thinks about starting a business
- The research Shopify did into why the average tenure of an S&P 500 company has dropped from 30 years to under 20, and what that taught Harley about building a "100-year company"
- Why Shopify deliberately ships features before they're fully baked, and which parts of the platform, like checkout and payments, are never allowed to break
- What happened when Harley typed the same request into ChatGPT and Google looking for a screen-free phone for his daughter, and why one sent him to Best Buy and the other sent him to a small independent brand
- The eye-opening stat Harley shared on Shopify's earnings call: over 70% of orders coming from AI agents are for products outside Shopify's top 100 categories, and what that means for small merchants versus big box retailers
- Why Harley believes agentic commerce is the first truly "merit based" discovery tool, and what separates lasting celebrity brands like Emma Chamberlain's coffee company from one-hit-wonder influencer launches
- The story behind Fire Belly, the seven-figure tea company Harley started during the pandemic with his best friend, and why running his own Shopify store makes him a better product leader
- Why Harley calls himself and Shopify "spiky, not well-rounded," and how knowing exactly what you're good at shapes how he spends his time as president
- The "cha-ching" sound that Harley calls the secret handshake of the Shopify merchant community, and the story of hearing it in a random airport
