The Knowledge Project Podcast

5 episodes

7h 24m of content

124,823 total views

He requalifies for his job every year and holds himself to the same standard at home. In this candid conversation, Shopify president Harley Finkelstein opens up about the family motto that guides him (“how you do anything is how you do everything”), the courage to close doors, and the simple AI habit that separates leaders who scale from those who stall.  You’ll get an unfiltered look at how this plays out behind the scenes—from stepping down as COO to become Shopify’s chief storyteller, to quarterly calendar audits, to choosing “spiky” partners over well-rounded executives, to learning when to listen instead of fix. Harley shares: ◽️ Why he requalifies annually (and how Tobi pushes him to find the next gear) ◽️ The family motto that sets the bar at work, in marriage, and with kids ◽️ The identity shift from COO to president & why a smaller scope can mean a bigger impact ◽️ How to design a calendar that kills mediocrity and protects energy ◽️ A simple script to avoid “problem-solving mode” in relationships ◽️ Why “spiky objects” beat well-rounded execs in founder-led companies ◽️ The reflexive AI rule Shopify expects and what it means for your career Harley x The Knowledge Project ----- Thank you to our sponsors for this episode: SHOPIFY: Sign up for your one-dollar-per-month trial period at https://www.shopify.com/knowledgeproject MINT MOBILE: Get your 3-month Unlimited wireless plan for just 15 bucks a month at https://www.mintmobile.com/knowledgep... ----- Timestamps: 00:00 Welcome, Harley 00:48 Living with unreasonably high standards 02:18 Generational trauma and family relationships 15:50 Prioritizing life to become world-class 25:48 Re-qualifying for your job 31:09 Mindset for growth and success 32:33 How to find a great business partner 34:00 Switching from COO to President 41:36 Storytelling’s impact at Shopify 43:42 How to get better at storytelling 48:45 Shopify and the evolution of commerce 50:58 Forced vs. passion-based entrepreneurship 53:02 Mentorship 1:01:09 Overcoming failure and rejection 1:04:14 Why “out-caring” beats IQ and EQ 1:08:21 Parenting and resilience 1:15:24 Teaching high-agency and responsibility 1:21:11 Calendar management system 1:27:00 AI and Shopify 1:40:55 If you aren’t using AI, you will fall behind ---- About Harley: Harley Finkelstein is the President of Shopify. He leads storytelling, external relations, and company energy—translating world-class product into world-class adoption. If this gave you one standard to raise your team—or your family—share it with a leader who needs to hear it today. https://x.com/harleyf   / harley   ----- Follow Shane https://x.com/shaneaparrish   / farnamstreet     / shane-parrish-050a2183   If you like this, check out these other interviews: 🎬  Morgan Housel: What You Need to Master (And Avoid) to Get Rich, Stay Rich, and Build Wealth:    • Morgan Housel: What You Need to Master (An...   🎬  The Marketing Expert: Sell Anything with this Trick | April Dunford:    • The Marketing Expert: Sell Anything with t...   🎬  A Practical Guide on Finding Inner Peace | Jack Kornfield:    • A Practical Guide on Finding Inner Peace |...   The Knowledge Project Like the mentor you’ve always dreamed of having, The Knowledge Project shares timely yet timeless lessons for work and life. Learn how leaders make decisions and achieve unprecedented results. Listen to The Knowledge Project Podcast on Apple, Spotify, or wherever you get your podcasts.