What does it mean to live—and lead—with intention?

Shane sits down with his friend and Shopify President Harley Finkelstein to explore what happens when you treat every role in your life—father, husband, leader—as something you have to requalify for, every single year. Harley shares why stepping down as COO was the hardest decision of his life, how a simple family motto is shaping his daughters, and what it really takes to become a world-class storyteller. They also unpack AI’s real advantage, the calendar system that keeps him honest, and the quiet force of standards that never get lowered.

It’s a candid look at ambition, identity, and the challenge of holding yourself to a higher standard—everywhere it counts.

Approximate timestamps: Subject to variation due to dynamically inserted ads: (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

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