Making the Most Out of Life and Business with the President of Shopify
April 13, 2023
AI Summary
5 min read"I Don't Want Any Transition Time"
Harley Finkelstein, president of Shopify, opened with a confession: he is optimizing his entire life for low transition time. He wants to be either fully on—building the business—or fully immersed in things that give him joy, like family, hobbies, and great conversations. The worst part of his high school day was the 30-minute commute, not because it was long, but because it was non-productive time he couldn't enjoy. This framing—that time spent neither building nor enjoying is time wasted—runs through the entire conversation, but not in the way a hustle-culture advocate might expect.
The Eight-to-Ten Hour Lever
Finkelstein described a Monday morning when he woke up unmotivated and texted a founder group chat. The response he got was counterintuitive: "I actually don't think your life will improve much by applying more pressure. I think your life will improve most by creating space to think, by protecting, nurturing your energy." The advice was to aim for eight to ten hours of highly leveraged work per week—hours worth five thousand dollars each—and then do everything else with the remaining time to keep those hours valuable.
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What you'll learn
- 1 Timestamped Outline
- 2 (00:32) **Hassle vs. Balance & The Anti-Transition Philosophy** - Harley Finkelstein explains his personal philosophy of minimizing transition time between work and life, aiming to be either fully engaged in building or fully engaged in joy, with nothing in between.
- 3 (02:17) **The 8-10 High-Leverage Hour Framework** - A founder friend's advice on shifting from hustle to high-value work: focus on 8-10 highly leveraged hours per week worth $5,000/hour, and protect the rest of your time to keep those hours valuable.
- 4 (04:22) **Meaning Over Happiness** - Harley argues that the goal isn't constant happiness but a meaningful life, and shares how naming emotions helps pattern-match and prepare for tough days.
- 5 (08:26) **The Montreal Immigrant Hustle** - Harley explains how growing up in Montreal's immigrant culture created a unique entrepreneurial DNA rooted in survival rather than passion, with immigrant entrepreneurs as local heroes.
- 6 (14:52) **Building Your Own Tribe in a Non-Entrepreneurial City** - When Harley moved to Ottawa (a government town), he had to intentionally create his own entrepreneurial community, leading to Fresh Founders and a network that produced Shopify, Getaround, and other companies.
- 7 (17:08) **Obvious vs. Non-Obvious Mentors** - Harley explains the power of seeking mentors who aren't famous or obvious, noting that these people have disproportionate "alpha" because their stories haven't been told.
+ Full timestamped outline available in the app
Show Notes
Today Greg is joined by Harley Finkelstein, the President of Shopify. In this episode, Greg and Harley talk about growing up in a predominantly immigrant neighborhood in Canada, getting mentors and finding joie de vivre.
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LINKS FOR THIS EPISODE:
Production Team:
https://www.bigoceanpodcasting.com
Harley Finkelstein:
https://www.shopify.com/
https://twitter.com/harleyf
SHOW NOTES:
0:00 - Intro
5:49 - Growing up in Montreal as a Jewish Canadian
10:56 - Finding peers that inspire you
18:29 - The benefits of non-obvious mentors
26:06 - How to DM your heroes
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