From Start-Up to Grown-Up [ENCORE] #110 Jim McKelvey, Cofounder of Square - Innovation When it's Your Only Choice, Overcoming Regulation, and Managing His Intern, Jack Dorsey
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Jan 27, 2026 
Jim McKelvey, entrepreneur, glassblower, and Square cofounder, shares the wild origin of Square and the idea born from one lost sale. He explains the Innovation Stack and why true innovation often comes from necessity. He recounts battling competitors, building mission-driven teams, the personal toll of startup life, and lessons from glassblowing and unexpected leadership.
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The Lost Sale That Started Square
- Jim lost a sale because a buyer only had an American Express card and he couldn't accept it.
- That single lost sale on his iPhone sparked the idea for Square and led him to call Jack Dorsey to build a card reader.
Bob: The Merchant Square Aimed To Help
- Jim describes 'Bob', a talented glassblower who couldn't make a living because he couldn't access bank payment tools.
- Bob became the poster child inspiration for building Square to serve merchants excluded by the payments system.
Hire For Mission, Not Money
- Recruit people who care about the mission, not just money; mission-driven teams endure hardship.
- Be explicit about the tough obstacles early so only committed, mission-aligned people join.
