Apple's strict dock connector rules nearly killed Square's early hardware ambitions
Jim McKelvey · Square: Jim McKelvey. He Lost a $2,000 Sale, Then Built a $10 Billion Company · Feb 23, 2026 · at 44:24
Square co-founder Jim McKelvey describes the technical and commercial hurdles of building on the iPhone before routing the reader through the headphone jack.
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“And at the time, it was this big port at the bottom, and you had to pay Apple for access to that port. You had to pay Apple for a special chip that allowed you to build your hardware, and then you had to Convince them to let you do it, and at the time the iPhone had a terrible battery, and so they wouldn't let you do anything that sucked power from the device, because that just made the battery performance worse. So there was almost zero chance of us getting permission from Apple to connect a credit card reader to their device.”
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