The Way I Heard It with Mike Rowe The Way I Heard It with Mike Rowe

507: Jim McKelvey—A Square Peg in a Glass Hole

Oct 13, 2026 · 1h 11m

Summary

Mike Rowe interviews Jim McKelvey, the co-founder of Square, about his journey from glassblower to tech innovator. They discuss how McKelvey invented Square to solve a personal payment problem and the lessons he learned about teamwork and trust from his artistic background. The conversation explores the challenges of authenticity in the age of AI, the importance of shipping imperfect products, and the value of genuine human connection over polished media training.

Topics discussed

Introduction to Jim McKelvey and the Square story The origin of Square: Solving a personal payment problem TechShop, Mark Hatch, and the path to co-founding Square Discussion of Jim's book 'Innovation Stack' and recording location Sponsor segment: Chapter Medicare plan inspection Meeting Jim: From TechShop fame to Square co-founder Memories of TechShop: The lunar lander and maker culture 3D printing, vices, and the drive for innovation Clarifying roles: Jack Dorsey and the Square co-founding The iPhone as a credit card machine: The core concept Jim's background: Computer engineering and glass blowing Vocation vs. Avocation: Learning skills for survival The metaphor of bending glass to will and teamwork The dance of glass blowing: Balance and focus Teamwork in glass blowing: Working with John How a partner's presence affects hand movements and skill Serendipity and opportunity: Meeting new people The Wild Kingdom production and evolutionary context Audience engagement levels and the 'drug' of attention Control the glass: Lessons from avocation for business Microworks Foundation and closing the skills gap Pentagon funding and training opportunities for families The maker movement: Jim as a private maker Brand value vs. aesthetic value in art Meeting Mark Kastabi and the struggle with self-promotion The 'Goat' of glass blowing: Del Cihulli and Lino Tagliapietra The forgery story: Identifying a fake Lino Tagliapietra Luxury goods, authenticity, and the Timex metaphor AI, fake artists, and the need for authenticators The future of authenticity in an age of AI The $500 sweater and the psychology of ownership Artificial slop and the burial of genuine quality Jim's fear of AI and the lack of solutions The penny email: A solution to spam and noise The problem of unread emails and digital inundation Whitelisting and the value of small costs for access The terror of losing real quality to garbage Deciding if we care about fake art, food, and music Sponsor segment: Pure Talk Unlimited Data for Life The value of effort and the rewriting of books The editor's role and the 'dick joke' anecdote The toil of writing and the editor's feedback Authenticity in unscripted moments vs. edited work Respecting both studio albums and live concerts Cezanne, Picasso, and the nature of finished art The endless process of rewriting and refining Responding to audience demand and iterating on products Good is the enemy of great: The risk of settling Building unsolved problems and the need to fail fast Building a shadow banking system for Square The unexpected market response to Square's rough launch Jim's daughter Margaret and the value of unvarnished truth Knowing you are hearing the unvarnished truth The value of disagreeability and manners Sponsor segment: AI and business transformation The book 'Aligning for the Agentic Era' Media training and the stress of public visibility The $500 sweater hole and the cost of loss Lessons from media training: Not getting enthusiastic Henry Kissinger's one-sentence media training tip Talking to big brains and the lack of clear answers Working backwards from the end: A hotelier's wisdom Feeling like an imposter and the honor of inclusion Violent agreement and the nature of their rapport The 'Argument Clinic' skit and playful disagreement Continuing the 'Argument Clinic' bit Boring agreement and the search for innovation The counter-intuitive nature of innovation The phone call from Dallas and the start of the book Meeting Herb Kelleher in Dallas Herb Kelleher's smoking and the day of conversation The commandment to write a book The high of the moment and the decision to write Herb's objection to being a cartoon character The normal person protagonist in the book The superhero lens vs. the realistic innovation story The end of the glass blowing discussion Imitation, innovation, and being remembered Luck, timing, and surviving the innovation world Nothing special about Jim: Encouraging others The variables of doing it right enough Studying with Lino Tagliapietra 25 years ago The one question allowed in Lino's class The lesson in 'when' vs. 'how' in glass blowing The critical importance of timing in glass Closing remarks and well-wishes for the family Sponsor segment: Organic Valley Protein Plus Milk Sponsor segment: Lincoln Rejuvenate
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