Square: Jim McKelvey. He Lost a $2,000 Sale, Then Built a $10 Billion Company
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
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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.
The Economy is Fine?, VC Funding Declines, Non-Negotiable Expectations
Square co-founder and Invisibly founder Jim McKelvey joins Ranjan Roy and Alex Kantrowitz for our weekly news recap show. We cover: 1) The state of the economy and markets 2) Fears of a credit crunch, or is it a credit tightening? 3) The state of the commercial real estate market 4) How commercial real estate's struggles impact small and regional banks 5) The decline in VC funding in Q1 6) What is 'dry powder' anyway? 7) Reflecting on Uber again 8) What is AutoGPT? 9) Regulating AI 10) Sell your data for money? 11) The Square reader's founding story 12) "Non-negotiable" expectations.
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What's Next For Our Crazy Economy — With Square Co-Founder Jim McKelvey
Jim McKelvey is the co-founder of Square, chair of the St. Louis Fed, and founder of Invisibly. He joins Big Technology Podcast to discuss whether the Fed should still hike interest rates given the markets' slowdown and the conflict in Ukraine. Stay tuned for a discussion of how Jim tolerates risk, why he's not building his new startup on the blockchain (aka: Web3), and a preview of our SXSW featured session: The Future of The Data Economy: Putting People First, taking place March 11 in Austin.
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Exploitation Economy
Scott discusses how the Tech Giants will see a snapback in their US advertising revenue, as well as how the disruption to higher education has already begun and why universities need to rethink their plans. Scott also brings on Jim McKelvey, the co-founder of Square, to hear his ideas around innovation, the payments sphere, and advice to entrepreneurs. McKelvey is also the author of “The Innovation Stack: Building an Unbeatable Business One Crazy Idea at a Time.”
This week’s Office Hours: Palantir’s potential IPO, what to expect when impact investing, and how to build your personal brand.
Algebra of Happiness has Scott wondering when the US moved from an innovation economy to an exploitation economy.
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