Harley Finkelstein — Tactics and Strategies from Shopify, The Future of Retail, and More (#486)

Illustration via 99designs

I’m fascinated with how people find ambition, keep ambition, increase ambition, and unfortunately, as well, lose ambition.

— Harley Finkelstein

Harley Finkelstein (@harleyf) is an entrepreneur, lawyer, and the President of Shopify. He founded his first company at age 17 while a student at McGill. Harley is an advisor to Felicis Ventures, and he is one of the “dragons” on CBC’s Next Gen Den. In 2017, he received the Canadian Angel Investor of the Year award and Canada’s Top 40 Under 40 award, and in 2016 he was inducted into the Order of Ottawa. From 2014 to 2017 Harley was on the board of the C100, and from 2017 to 2020 he was on to the board of directors of the Canadian Broadcasting Corporation (CBC).

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#486: Harley Finkelstein — Tactics and Strategies from Shopify, The Future of Retail, and More


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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear an episode with Shopify’s founder and CEO? Check out my conversation with Tobi Lütke, in which we discuss feedback as a gift, fostering a growth mindset, the impact of dyslexia on Tobi’s reading list and coding endeavors, understanding “the next box,” why the business world should be keeping a close eye on the video game industry, Enneagrams, and much more.

#359: Tobi Lütke — From Snowboard Shop to Billion-Dollar Company


DISCLAIMER: I own stock in Shopify. I was not compensated in any way to have Shopify represented on the program or to talk about my reasons for investing in Shopify. I may financially benefit if Shopify’s stock goes up in value. I am not an investment adviser. All opinions are mine alone. There are risks involved in placing an investment in any company. None of the information presented today is intended to form the basis for any offer or recommendation, or have any regard to the investment objectives, financial situation or needs of any specific person.


  • Connect with Harley Finkelstein:

Website | Twitter | Instagram

  • Connect with Shopify:

Shopify | Twitter | Instagram | Facebook | YouTube


  • For anyone not in the know, what is Shopify, and how does Harley envision it scaling to become the entrepreneurship company? [06:50]
  • What books have been most formative for Harley in his business journey with Shopify? What books has he gifted the most to other people? [09:37]
  • How much has Shopify grown during the time in which I’ve known Harley? [14:00]
  • How did Harley wind up moving from Montreal to South Florida and back to Montreal again, who is Phillip Rimer, and what part does he play in Harley’s story? [19:14]
  • As someone who went to law school not to become a lawyer, but become a more effective entrepreneur, what were Harley’s most valuable takeaways from the experience? [28:37]
  • How did Harley most effectively play along with the Socratic method in law school, and how did he bypass the need to absorb 1,200 pages of case study? [33:18]
  • How would Harley design a curriculum that would convey the lessons he learned in law school without the need to actually go to law school, and which texts might I add to the list of required reading? [37:38]
  • I give one must-read fiction recommendation to the guy who’s just now reading a work of fiction for the first time in his life. [43:07]
  • What does Harley’s job at Shopify as COO actually entail, and how does annual re-qualification work there? [43:49]
  • Who is Tobi Lütke, and how did he and Harley meet? [45:47]
  • How did Harley get licensing agreements that made him competetive — as a nobody law student selling t-shirts — with monolithic companies like Walmart? [53:26]
  • How did Harley become the proprietor of Shopify Store 136? [56:06]
  • What were the early days of investment fundraising for Shopify like? [59:44]
  • How I met Tobi and Harley, and the piece of advice I gave them that they took to heart. [1:06:33]
  • On formulating the Build a Business competition that differentiated Shopify from the competition — even if the projected price tag seemed a bit steep at the time. [1:08:06]
  • How the winner of year one’s Build a Business competition helped rejuvinate a dying industry and accessorize a US president, and how year two was designed to differentiate Shopify even further. [1:15:32]
  • What impact have the multi-pronged surprises of 2020 had on retail, and what does Harley see for the future of the industry as a result — particularly ecommerce — that others might be missing? [1:17:55]
  • My own observations about ecommerce adaptations during 2020. [1:26:47]
  • Harley explains how Shopify is “arming the rebels,” and why ecommerce is poised to help support local communities, small businesses, and independent brands — especially during tough times. [1:29:46]
  • How are coaches used at Shopify, what makes some coaches more effective than others in the context of the company culture, and what does it mean when Harley says leadership has to “requalify” for their jobs every year? [1:31:38]
  • What does time with a coach at Shopify typically look like, how does Shopify’s post-coach era compare with its pre-coach era, and what does Shopify’s “trust battery” ultimately empower? [1:38:55]
  • Naming coaching as “one of the top three or four things” that he’s done, what are some of those other things that have moved the needle for Harley? [1:42:46]
  • After trying several “flavors” of meditation that didn’t really work for him, what variety does Harley find effective? [1:44:49]
  • On the importance of blocking out time for family and loved ones (and sometimes just yourself) when an otherwise busy schedule might inadvertendly elbow them out of the picture. [1:47:22]
  • What contemporary C-suite executives does Harley most admire as examples, and what is his unique approach to seeking out the most valuable advice from mentors? [1:50:10]
  • Why you never want to “entice” a busy, potential mentor-level person with these words: “May I take you to coffee and pick your brain?” (And some advice for how you might get better results.) [1:54:56]
  • Influential and thought-provoking biographies. [1:56:33]
  • “Nice guys finish last” is not a truism, and other parting thoughts. [2:00:09]