Square: Jim McKelvey. He Lost a $2,000 Sale, Then Built a $10 Billion Company
How I Built This with Guy Raz
Guy Raz | Wondery
4.7 • 31.4K Ratings
🗓️ 23 February 2026
⏱️ 74 minutes
🧾️ Download transcript
Summary
Most entrepreneurs think the hardest part of building a company is the product.
For Jim McKelvey — co-founder of Square — the hardest part was the system around the product.
Because Square wasn’t just competing with other startups …
It was competing with regulations, middlemen, entrenched networks, and monopolies designed to keep outsiders out.
In this episode, Jim shares the mindset and tactics that helped Square go from a tiny card reader that processed credit card payments … to a company—now known as Block— that generates over $10 billion in gross profit.
What You’ll Learn:
- Why the market is often “locked” on purpose
- How a simple hack can solve a seemingly complex problem
- How candor can sway investors more than confidence
- How Square survived by building something Amazon couldn’t copy
Timestamps:
- 00:12:26 – Engineering and art: Balancing an IBM job with glassblowing
- 00:15:46 – The family trauma that rewired Jim
- 00:36:26 – Losing a $2,000 sale — the moment Square was born
- 00:43:06 – Breaking into the credit card club: “We were violating 17 rules”
- 00:48:31 – The headphone jack hack that sidestepped Apple’s control
- 00:58:03 – The “140 reasons we might fail” pitch that won over investors
- 01:06:26 – The taxi ride that convinced Jim he had product-market fit
- 01:09:28 – Amazon attacks, and why copying doesn’t always work
- 01:13:18 – The founder’s job after success: choosing hard problems
***
Hey—want to be a guest on HIBT?
If you’re building a business, why not get advice from some of the greatest entrepreneurs on Earth?
Every Thursday on the HIBT Advice Line, a previous HIBT guest helps new entrepreneurs work through the challenges they’re facing right now. Advice that’s smart, actionable, and absolutely free.
Just call 1-800-433-1298, leave a message, and you may soon get guidance from someone who started where you did, and went on to build something massive.
So—give us a call. We can’t wait to hear what you’re working on.
***
This episode was produced by Alex Cheng with music composed by Ramtin Arablouei. It was edited by Neva Grant with research help from Katherine Sypher. Our engineers were Patrick Murray and Robert Rodriguez.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Transcript
Click on a timestamp to play from that location
| 0:00.0 | I heard this stat recently that really stuck with me. Most businesses only use 20% of their data. |
| 0:08.4 | That's like reading a book with most of the pages torn out. How can you get the full story? And where's the other 80% of that data? |
| 0:17.1 | It's trapped in emails, buried in call logs and chat transcripts where businesses can't use it. |
| 0:23.7 | That's where HubSpot comes in. Their customer platform brings everything together so you can get the |
| 0:29.7 | full story, because when you know more, you grow more. Visit HubSpot.com to get started. |
| 0:40.3 | One of the things about my job interviewing hundreds of founders is that I try a lot of products. I'm always looking around for interesting brands. |
| 0:45.3 | But sometimes when I'm about to order something and I don't have my wallet on me, I'm trying to remember all the details and it's really and annoying, trying to fill out all that stuff again and again. |
| 0:57.2 | And that's when I see it, that purple pay button that has all of my information saved, making checkout as simple as a tap on my screen. |
| 1:07.8 | Shopify is the commerce platform behind millions of businesses around the world, with world-class |
| 1:13.9 | expertise and everything from managing inventory to international shipping to processing |
| 1:19.1 | returns and beyond. See less carts go abandoned and more sales go with Shopify and their shop pay button. |
| 1:29.4 | Sign up for your one pound per month trial today at Shopify.co.com.uk slash built. |
| 1:36.0 | Go to shopify.com. |
| 1:38.4 | That's shopify.com.uk.uk slash built. |
| 1:46.0 | Hey, just a quick message. If you're building a business right now, imagine getting |
| 1:52.1 | advice from the founder of Tart Cosmetics or Airbnb or even Sir Richard Branson or |
| 1:58.5 | Mark Cuban. Well, you can get that advice. |
| 2:02.2 | Every Thursday, we drop an episode of the How I Built This Advice Line. |
| 2:05.9 | It's where I bring back a previous founder we featured on a past episode. |
| 2:11.0 | And together, we help real entrepreneurs, people selling skin care, dog toys, pottery, food, whatever. We help them work through the challenges |
| 2:20.2 | they're facing right now. And the best part, this kind of advice world-class battle tested is |
| 2:27.3 | completely free. All you have to do is call 1-800-433-1298. Tell us what you're building in under a minute, and you might be the next |
... |
Please login to see the full transcript.
Disclaimer: The podcast and artwork embedded on this page are from Guy Raz | Wondery, and are the property of its owner and not affiliated with or endorsed by Tapesearch.
Generated transcripts are the property of Guy Raz | Wondery and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.
Copyright © Tapesearch 2026.