[ENCORE] #110 Jim McKelvey, Cofounder of Square - Innovation When it's Your Only Choice, Overcoming Regulation, and Managing His Intern, Jack Dorsey
Tue Jan 27 2026
What does it actually take to build something that has never existed before?
In this episode, Jim McKelvey, co-founder of Square (now Block), breaks down the real story behind building Square from scratch, not with a perfect plan, but through necessity, invention, and relentless problem-solving.
Jim introduces the concept of the Innovation Stack, why innovation is rarely chosen willingly, and why copying “what worked before” fails when you’re solving a problem no one else has solved. He shares the moment Square felt real, the panic of Amazon launching a competing product, and the counterintuitive strategy that helped Square survive.
You’ll learn:
What the Innovation Stack is and why it protects companies from copycatsHow Square started from a single lost sale and grew into a global companyWhat happens emotionally when you’re building something no one understands yetWhy copying best practices can fail when you’re solving a brand-new problemWhy mission-driven teams outperform money-driven ones over timeWe talk about:
00:00 Why timing is everything, and why being “too early” still hurts05:30 The moment Square was born, one lost sale that changed everything10:00 Why the payments industry was designed to exclude small businesses16:30 Mission vs money, and why people joined even when they could leave20:00 Amazon launches a competing product, and Square’s unexpected response26:00 The Innovation Stack explained, and why it’s almost impossible to copy31:00 Panic attacks, pressure, and the nervous system cost of building35:30 Copying vs innovating, and where founders get trapped47:00 Imposter syndrome, even after successFollow Alisa Cohn on
Instagram: https://www.instagram.com/alisacohn/ Twitter: https://x.com/AlisaCohn Facebook: https://www.facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better): AlisaCohn.com/scripts
Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon
Connect with Alisa!
Follow Alisa Cohn on
Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better)
Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon
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What does it actually take to build something that has never existed before? In this episode, Jim McKelvey, co-founder of Square (now Block), breaks down the real story behind building Square from scratch, not with a perfect plan, but through necessity, invention, and relentless problem-solving. Jim introduces the concept of the Innovation Stack, why innovation is rarely chosen willingly, and why copying “what worked before” fails when you’re solving a problem no one else has solved. He shares the moment Square felt real, the panic of Amazon launching a competing product, and the counterintuitive strategy that helped Square survive. You’ll learn: What the Innovation Stack is and why it protects companies from copycatsHow Square started from a single lost sale and grew into a global companyWhat happens emotionally when you’re building something no one understands yetWhy copying best practices can fail when you’re solving a brand-new problemWhy mission-driven teams outperform money-driven ones over timeWe talk about: 00:00 Why timing is everything, and why being “too early” still hurts05:30 The moment Square was born, one lost sale that changed everything10:00 Why the payments industry was designed to exclude small businesses16:30 Mission vs money, and why people joined even when they could leave20:00 Amazon launches a competing product, and Square’s unexpected response26:00 The Innovation Stack explained, and why it’s almost impossible to copy31:00 Panic attacks, pressure, and the nervous system cost of building35:30 Copying vs innovating, and where founders get trapped47:00 Imposter syndrome, even after successFollow Alisa Cohn on Instagram: https://www.instagram.com/alisacohn/ Twitter: https://x.com/AlisaCohn Facebook: https://www.facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better): AlisaCohn.com/scripts Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon Connect with Alisa! Follow Alisa Cohn on Instagram: @alisacohn Twitter: @alisacohn Facebook: facebook.com/alisa.cohn LinkedIn: https://www.linkedin.com/in/alisacohn/ Website: http://www.alisacohn.com Download her 5 scripts for delicate conversations (and 1 to make your life better) Grab a copy of From Start-Up to Grown-Up by Alisa Cohn from Amazon