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How I Built This with Guy Raz
How I Built This with Guy Raz

Square: Jim McKelvey. He Lost a $2,000 Sale, Then Built a $10 Billion Company

February 23, 2026 • 1h 11m

Summary

⏱️ 11 min read

Overview

Jim McKelvey, co-founder of Square, shares the story of how a lost $2,000 glass sale led to revolutionizing credit card payments for small businesses. Partnering with former intern Jack Dorsey, McKelvey built Square from scratch in 2008-2009, creating both hardware and software that challenged banking monopolies and regulatory barriers. The company survived Amazon's attempt to crush it in 2014 and grew into a multi-billion dollar business by fundamentally changing how small merchants accept payments.

Early Life and the Impact of Personal Tragedy

Jim McKelvey's mother committed suicide when he was 24, a devastating event that fundamentally changed his worldview and approach to life. This tragedy woke him up to suffering he hadn't noticed before and instilled in him a sense of urgency about taking action when he sees problems. The experience taught him that inaction is unacceptable when you care about something, a philosophy that would drive his entrepreneurial ventures for decades.

  • Jim's mother struggled with severe depression and committed suicide on December 18, 1989, completely blindsiding him
  • The loss made him realize he had lived in oblivious comfort, never having faced real hardship before
  • The tragedy awakened him to pain and suffering in others that he had never noticed
  • He developed a philosophy that inaction in the face of problems is unacceptable - you must be the one to do something
" I could have just gone home and taken a walk with my mother every night. That could have saved her life. I didn't do that. To this day, I regret the inaction. And so when I find myself in a situation where I think something needs to be done, I no longer sit there and say, well, someone else will probably do it. My attitude is like, you got to be the one to do something. "
" If I care about something and I don't try to fix it then I question whether or not I really cared "

The Mira Years: Learning to Pivot and Survive

After his mother's death, McKelvey quit IBM, closed his CD business, and stopped glassblowing to focus on building Mira, a document imaging company similar to what Adobe Acrobat would become. When Adobe crushed that business, McKelvey pivoted to creating CD-ROMs for trade shows, charging companies $10 per page to include their literature. This became extremely profitable, making $70,000 on a single CD. When the internet threatened that business, he pivoted again to academic conference publishing, which kept Mira alive.

  • After his mother's death, McKelvey decided to stop being mediocre and focus entirely on computers
  • Mira built document reading software similar to Adobe Acrobat, but Adobe destroyed that business
  • McKelvey created the first CD-ROM for an imaging trade show, making $70,000 in profit despite the trade association trying to sue him
  • When the internet threatened to kill the CD-ROM business, McKelvey pivoted to academic conference publishing
" My mother has seen nothing but mediocrity out of her son. I don't know. You have three businesses and you're 24. I don't, that doesn't sound mediocre to me. I have three businesses, but they all kind of suck. "

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