Hardware Podcasts

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

How I Built This · 23 Feb 2026 · 1h 11m

What this episode covers

Jim McKelvey, co-founder of Square (now Block), explains how a lost $2,000 glass art sale to a customer with only an American Express card inspired the creation of the Square card reader. He details the engineering hack of using the iPhone's headphone jack to read magnetic stripes, bypassing Apple's restrictive dock connector, and the strategic decision to pitch investors with 140 reasons for failure to build trust. McKelvey describes how this 'innovation stack' of 14 necessary inventions protected Square from being crushed by Amazon's cheaper, copied product in 2014, allowing the company to thrive despite regulatory hurdles and legal disputes.

Most relevant to

early-stage companies

Topics

Mentioned

Companies
Block, Twitter, Amazon, Apple, Mira
Products
Square, iPhone
Also
Jack Dorsey, Visa, MasterCard, American Express, Make magazine

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