#236 Harley Finkelstein: 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

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

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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