#236 Harley Finkelstein: Why You Must Requalify for Your Role—Every Year

The Knowledge Project with Shane Parrish

Farnam Street

Business, Investing, Entrepreneurship

4.7 • 2.9K Ratings

🗓️ 8 July 2025

⏱️ 106 minutes

🔗️ Recording | iTunes | RSS

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Summary

What does it mean to live—and lead—with intention? Shane sits down with his friend and Shopify President Harley Finkelstein to explore what happens when you treat every role in your life—father, husband, leader—as something you have to requalify for, every single year. Harley shares why stepping down as COO was the hardest decision of his life, how a simple family motto is shaping his daughters, and what it really takes to become a world-class storyteller. They also unpack AI’s real advantage, the calendar system that keeps him honest, and the quiet force of standards that never get lowered. It’s a candid look at ambition, identity, and the challenge of holding yourself to a higher standard—everywhere it counts. Approximate timestamps: Subject to variation due to dynamically inserted ads: (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 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

Transcript

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0:00.0	It completely changed my energy levels. It made me exothermic again. It made me excited again.
0:05.0	It made me want to recommit year after year after year to Shopify and to Toby and to and to this mission that we're on.
0:12.0	Go a little deeper on your father and how that's impacted you and what that relationship was like.
0:18.0	At 17 years old, the rug got pulled from me,
0:21.2	and I was forced to basically grow up overnight.
0:24.7	Ultimately, if you think about the mission of Shopify,
0:27.6	it's we want to create more entrepreneurs.
0:29.4	We want to make entrepreneurship more accessible,
0:31.0	but we think that entrepreneurship allows anyone to do that.
0:34.5	It's the great equalizer.
0:35.8	The way that I think I had the most amount of value to Shopify
0:37.6	is the same thing that I want to be what class at, which is...
0:40.3	I want to start with what areas of your life do you think you have...
0:52.3	What other people would consider unreasonably high standards?
0:58.8	Foof.
1:00.6	Maybe start with, I mean, professionally, I think.
1:04.9	I am pretty hard in myself in terms of achievement.
1:11.5	Years ago, I read something about the concept of abundance versus scarcity mindsets.
1:20.0	And I think generally I do not have an abundance mindset about the things in my life.
1:26.3	Some of that may be, I don't know, this is going deep
1:29.1	in the first minute, but some of them might just be like multi-generational trauma, which I actually
1:33.5	believe in. I think I carry some of the weight of my grandparents, Hawkehaw-Cost survivors,
	...

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