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

Key takeaways

Jim McKelvey’s invention of Square was prompted by a personal frustration with accepting American Express—a problem that many small businesses face.
Mastering a craft, such as glassblowing, involves understanding the importance of timing, emotional calm, and trust in others, lessons that translate into business.
Innovation often involves feeling lonely and terrified but is driven by the willingness to do what has never been done before.
Jim’s concept of the ‘Innovation Stack’ focuses on building companies through unconventional solutions that disrupt markets.
Jim fears that AI and digital content algorithms threaten genuine quality by favoring quantity and low effort, and he advocates for new tools like Mailwall to combat spam and forgery.
Media training is about strategic restraint—knowing when to speak and when to remain silent—and about aligning honesty with personal integrity.
The timing of actions and decisions, exemplified by Lino’s glassblowing advice, is critical in both art and business success.
Humility, patience, and continual learning are essential components of mastery, whether in art, innovation, or entrepreneurship.

Summary

Jim McKelvey’s Unlikely Path from Glassblowing to Tech Success

This opening segment introduces Jim McKelvey, highlighting his unconventional career trajectory from a trained glassblower with a background in computer engineering and economics to co-founder of Square. Mike Rowe recounts how Jim’s frustration over not being able to accept American Express for a $2,000 sale led him to invent a square-shaped credit card reader for his iPhone. The story emphasizes how a personal problem prompted Jim to create a solution, eventually transforming small business payments and making Jim and Jack Dorsey billionaires. Mike also shares his admiration for Jim's journey, including his early days working at Techshop, a maker space designed to inspire entrepreneurship. The segment establishes Jim’s background and the serendipitous nature of his innovations, combining art, technology, and entrepreneurship.

The Art of Glassblowing as a Business and Life Lesson

In this mid-section, Jim delves into his experience as a glassblower, discussing the physical and mental discipline involved in mastering glass art. He compares the process to managing a dance, where timing and emotional calmness directly influence the quality of his work. Jim reflects on the importance of teamwork, trust, and communication, exemplified by how his ability to produce certain shapes improves when working with trusted colleagues like John. These insights extend beyond glassblowing into broader lessons about collaboration, focus, and the value of surrounding oneself with dependable partners, which Jim sees as key to both artistic and business success.

Innovation as a Personal and Business Journey

Jim explains his concept of the ‘Innovation Stack,’ a framework for building groundbreaking companies by doing things that have never been done before. He recounts his interactions with Herb Keller of Southwest Airlines, who encouraged him to write a book about this philosophy. Jim shares the story of how Herb's directness and his approach to continuous improvement influenced his thinking. He emphasizes that innovation often involves feeling isolated and terrified but requires persistence and timing. Jim emphasizes that most innovation results from luck and timing, and encourages others to take risks and pursue unique problems they care about.

The Challenges of Authenticity and Artificial Content

This section tackles the growing concern over AI and counterfeit media, with Jim expressing his fear that genuine quality will be overwhelmed and buried by artificial, low-effort content. He discusses how algorithms on social platforms favor quantity over quality, and he presents his countermeasures, such as the creation of Mailwall—a system where people pay a small fee to email him, reducing spam. Jim reflects on the importance of authenticity and how AI complicates distinguishing real from fake in art, music, and communications. He advocates for vigilance, respect for craftsmanship, and developing new tools to preserve actual quality in an increasingly synthetic digital environment.

Reflections on Mediation, Media, and Personal Integrity

Jim shares anecdotes about media training and how it teaches restraint and strategic communication, especially for public figures. He admits that live TV can tempt over-enthusiasm and that having a plan beforehand would mitigate mistakes. The conversation includes playful banter about disagreements, illustrating how common it is to be in near-agreement while pretending to debate, highlighting human tendencies toward politeness and the discomfort of conflict. Jim emphasizes the importance of honesty, humility, and self-awareness when engaging in media and public interactions, aligning these with his overall theme of authenticity.

The Power of Timing and Mastery in Art and Business

In the final segment, Jim recounts a memorable story about Italian glass master Lino Tagliapietra, illustrating the significance of timing, patience, and listening to expert advice. He describes how Lino’s simple yet profound guidance on timing transformed Jim’s technique, underscoring the importance of knowing 'when' to act. Jim draws parallels between mastering an art form and running a successful business, emphasizing that doing things at the right time and with the right intention is crucial for achievement. The episode concludes with a reflection on how both art and innovation require humility, experimentation, and an openness to continual learning.

Show notes

Jim McKelvey is an entrepreneur, innovator, computer engineer, and master glassblower who helped build a billion-dollar company. That's not the usual career path, but then, Jim McKelvey isn't your usual entrepreneur. The co-founder of Square, along with Jack Dorsey, McKelvey turned a frustrating experience in his glass studio into a business that changed the way small businesses get paid. Mike talks with Jim about the art of blowing glass, his involvement with TechShop, and why a guy who helped invent the future of payments is downright terrified of AI. They also discuss The Innovation Stack, McKelvey's book about the unconventional thinking that built Square—and why sometimes the best way to solve a problem is to stop doing what everybody else is doing.

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