Shopify President Harley Finkelstein talks with Shane Parrish about treating every role in your life like a job you have to earn again each year.
Harley shares why stepping down as COO was his hardest choice, the family motto that guides his daughters, and what makes someone good at storytelling. They discuss AI’s real advantage, the calendar system that keeps him accountable, and how he maintains high standards.
Approximate timestamps:
(00:02:10) Living With Unreasonably High Standards
(00:03:40) Generational Trauma and Family Relationships
(00:07:52) Growing Up With Adverse Circumstances
(00:14:42) Prioritizing In Life And Becoming World Class
(00:24:45) Requalifying For Your Job
(00:30:05) Mindset for Professional Growth and Success
(00:31:33) How To Find A Great Business Partner
(00:32:57) Switching From COO Of Shopify To President/Chief Storyteller
(00:40:34) How Storytelling Impacts Shopify
(00:42:00) How To Get Better At Storytelling
(00:46:13) Shopify And How Commerce Has Evolved
(00:49:27) Forced Entrepreneurship Vs Passion-Based Entrepreneurship
(00:51:34) Mentorship
(00:59:41) Overcoming Failure And Rejection
(01:02:46) Out Caring Is More Important Than IQ, EQ, Raw Talent
(01:06:07) Parenting And Teaching A Hardwork Ethic
(01:11:23) Teaching Resilience
Thanks to our sponsor for supporting this episode:
SHOPIFY: Sign up for your one-dollar-per-month trial period at shopify.com/knowledgeproject
MINT MOBILE: Get your 3-month Unlimited wireless plan for just 15 bucks a month at mintmobile.com/knowledgeproject
Newsletter – The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at fs.blog/newsletter
Upgrade — If you want to hear my thoughts and reflections at the end of the episode, join our membership: fs.blog/membership and get your own private feed.
Watch on YouTube: @tkppodcast
Learn more about your ad choices. Visit megaphone.fm/adchoices

#67 Jim Collins: Keeping the Flywheel in Motion
An earnest student and powerful teacher, mega best-selling author Jim Collins goes under the hood and shows what all enduring companies have in common. We talk luck, leadership, and business longevity. Go Premium: Members…
#66 Dr. Emily Nagoski: Pleasure is the Measure
Sex educator and author Dr. Emily Nagoski demystifies the science of sexuality and shows us how to shed our insecurities, connect more closely with our partner, and define pleasure on our own terms. Go…
#65 Shep Gordon: Trust, Compassion, and Shooting Friends from Cannons
Legendary show-business manager, agent, and producer Shep Gordon talks sex, drugs, and rock and roll. He also shares the formula for manufacturing fame, and his unique philosophy on success, love and happiness. Go Premium:…
#64 Greg Walton: The Big Impact of Small Interventions
Greg Walton, Associate Professor of Psychology at Stanford University shares the four types of interventions, how they’re used to create positive behavior change, and strategies we can use right now to improve our health, well-being,…
#63 Hugh Howey: Winning at the Self-publishing Game
Hugh Howey had two dreams: to make a living from writing and sail around the world. In this interview, he describes how he did both, why traveling is so good for the soul, and how…
#62 Dr. Sue Johnson: Cracking the Code of Love
Dr. Sue Johnson is a researcher, clinical psychologist and developer of EFT or Emotionally Focused Therapy. In this interview, we discuss how to create, protect, and nourish fulfilling sexual and emotional relationships. Go Premium:…
#61 Jonathan Haidt: When Good Intentions Go Bad
Jonathan Haidt is an author, social psychologist and one of the world’s leading experts in moral psychology. On the show we discuss helicopter parenting, the rise of the “call out culture,” and the dangers of…
#60 Jim Dethmer: Leading Above the Line
Jim Dethmer, founder of The Conscious Leadership Group shares practical advice about becoming more self-aware, ditching the victim mindset, and connecting more fully with the people in our lives. Go Premium: Members get early…
#59 Following Intellectual Curiosity with Thomas Tull
Thomas Tull, founder of Tulco and former CEO of Legendary Entertainment shares valuable lessons on learning from our own mistakes, asking difficult questions, and protecting our intellectual curiosity. Go Premium: Members get early access,…
#57 Sheila Heen: Decoding Difficult Conversations
Sheila Heen, two time NY Times best selling author, consultant, and lecturer at Harvard Law School, makes the tough talks easier by breaking down the three layers that make up every difficult conversation Go…