Shopify President: How To Become A Millionaire For The Price Of A Starbucks Coffee! E245

Harley Finkelstein joins Steven Bartlett to make the case that entrepreneurship is more accessible than ever, with the cost of failure close to zero. He traces his path from teenage DJ to college t-shirt seller driven by family survival after his father went to jail, to becoming Shopify's first non-technical employee. He unpacks ideas like 'spiky' skill stacking over being a well-rounded 'river stone,' antifragility in companies and people, and finding mentors by vertical rather than one-size-fits-all. The conversation turns deeply personal as he discusses pandemic loneliness, the painful transition from COO to President, and learning that vulnerability is a magnet not a repellent. He closes urging listeners to commercialize a hobby and just start.

• About a month into college Harley got a call that his father had been arrested and was going to jail, forcing him into survival mode that drove his entrepreneurship.
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• Harley admits he was not the right fit as Shopify's COO and that ego and insecurity made it hard to admit he wasn't the best CEO for the role.
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• He names the pandemic as his hardest personal period, describing intense loneliness, anxiety, and possible depression while living with his family.
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• He waited far too long to talk to anyone about struggling because he felt he had no right to complain given how fortunate he was.
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• On a vulnerability card he confesses 'I don't think I'm a great father' despite desperately wanting to be one.
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• He reveals he started roughly 20 companies that were total failures, including a slipper company, poker chip company, and nurse uniform company.
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• He admits he puts in around five hours memorizing data points before TV appearances and pretends success comes easily when it doesn't.
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• Harley started his own DJ company at 13 and hired himself because no one would hire a DJ who looked eight years old.
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• A mentor convinced him to attend law school not to become a lawyer but to selfishly extract skills that would make him a better entrepreneur.
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• Shopify began when a German immigrant in Canada built software to sell snowboards via a store called Snow Devil, then realized the software was the real business.
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• Shopify now accounts for about 10% of all e-commerce in the United States.
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• Harley calls Supreme his 'Moby Dick' brand because their massive flash sales would stress-test and strengthen Shopify's infrastructure.
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• Harley believes company culture should not be static and should change slightly and improve with every new hire.
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• He uses mentors by vertical, choosing different people for parenting, marriage, business, and charity rather than one all-purpose mentor.
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• He schedules personal priorities like 'walk with Lindsay' and 'ski time' directly in his calendar to protect what matters.
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• Shopify operates a 'digital by design' model with optional 'bursting' office locations, requiring teams to meet in person at least once a quarter.
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• Shopify merchants have collectively sold more than half a trillion dollars, with some billion-dollar companies starting from a 'shower idea' six years ago.
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