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The barriers between entrepreneurial dreams and reality have never been lower—yet for many, starting a business feels out of reach.
The tools of commerce have been fundamentally democratized—we’re entering an era where spare bedrooms compete with offices on Fifth Avenue, and solo entrepreneurs challenge century-old giants.
My guest today is Harley Finkelstein, President of Shopify and an entrepreneur who embodies the confluence of commerce and personal growth. Starting his first business as a 13-year-old DJ, Harley has evolved into a transformative force in global retail, helping millions of entrepreneurs manifest their dreams through Shopify’s platform.
Harley’s trajectory is compelling. From teenage hustler to law school graduate to tech executive, he’s consistently challenged the myopic view of what entrepreneurship can be. As Shopify’s President, he’s revolutionizing how we think about commerce, making business tools accessible to anyone with an idea and the courage to start.
“This is the greatest time ever, in the history of the world, to build a brand new business.”
– HARLEY FINKELSTEIN
Today, we span an expansive terrain of modern business and self-development. Harley discusses his recent Misogi challenge climbing 29,029 feet—a journey that taught him the power of incremental progress. We explore the evolution of Shopify from its origins helping small merchants to now powering Fortune 500 companies, demonstrating how the aperture for entrepreneurship has widened beyond what anyone imagined possible.
Harley shares his perspective on anxiety as a potential superpower when properly channeled, his family motto, “The way you do anything is the way you do everything,” and maintaining intentionality across all aspects of life. From his early days as a teenage DJ to selling t-shirts to support his family, Harley recounts how these experiences—including an unexpected stint in law school that became his “entrepreneurship finishing school”—shaped his approach to business and life.
We consider the future of retail through fascinating case studies—from Supreme’s iconic drops to how direct-to-consumer brands are revolutionizing commerce—and examine why having a powerful story is now as crucial as having a great product
Harley explains the delicate dance between ambition and presence, scaling a business while staying true to oneself, and why this might be the most promising moment in history to start something meaningful.
For those who prefer a visual experience, the conversation is available on YouTube. As always, the audio version streams wild and free on Apple Podcasts and Spotify.
For those seeking to understand how entrepreneurship can become a vehicle for self-actualization—or simply wondering if now is the time to start something of your own—this exchange is a must-listen.
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- Connect with Harley: Instagram | X | LinkedIn
- President of Shopify: Shopify
- Forbes: Harley Finkelstein
- NPR Foundation: President of Shopify and entrepreneur Harley Finkelstein on “retail everywhere”
- Speakers Spotlight: Shopify’s Harley Finkelstein on How to Pitch “Next Gen Den”
- Brain Station: Announcing the Winners of the Sixth Annual Canadian Startup Awards
- Fortune: 40 Under 40
- UOttawa: Harley Finkelstein, JD & MBA ’09, named one of Fortune’s 2021 Top 40 Under 40
- TV Show: I Quit
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Thank The Team: I do not do this alone. Send your love to Jason Camiolo for audio engineering, production, show notes and interstitial music; with additional audio engineering by Cale Curtis and additional music by Moby; Dan Drake & Morgan McCrae for video, & editing; graphics by graphics by Alejandro Ribadeneira & Bryan Lawrence; portraits by Davy Greenberg; copywriting by Ben Pryor; and theme music by Tyler Piatt, Trapper Piatt & Hari Mathis.
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