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tech 24 July 2026

The Day Steve Jobs Dissed Me in a Keynote (2010)

Derek Sivers shares how a meeting with Steve Jobs changed his perspective on the interaction between tech innovation and the music industry. A revealing 2010 episode revisited.

Article inspired by the original source
The day Steve Jobs dissed me in a keynote (2010) ↗ sive.rs

Introduction

In May 2003, Derek Sivers, the founder of CD Baby, was invited to Apple's headquarters in Cupertino. The goal? Discuss integrating CD Baby's catalog into the newly launched iTunes Music Store. It was a pivotal moment for the music industry, marking a shift towards digital. However, the meeting took an unexpected turn when Steve Jobs himself took the stage.

The Context

iTunes had just launched, featuring only some music from major labels. The idea of a digital music store was still uncertain for many in the music business. Platforms like eMusic had tried this model with limited success. However, Apple had a vision: to make all music accessible.

The Meeting with Steve Jobs

Derek expected to meet with marketing or technical staff. To his surprise, about a hundred people from independent labels and distributors were present. Steve Jobs appeared, charismatic and determined to persuade his audience. "We want the iTunes Music Store to have every piece of music ever recorded," he stated. For independent musicians, this was monumental.

Technical Hurdles

Apple presented the software required for uploading albums to iTunes. Each CD needed to be inserted into a Mac drive, with info manually entered, clicking [encode] then [upload]. Derek raised an issue: he already had 100,000 albums digitized, ready to be sent. Apple's response was firm: "You need to use our software."

The Information Leak

After the meeting, Derek shared his notes online. Quickly, he received furious messages from his Apple contact. No confidentiality was mentioned during the meeting, but he removed his notes as a courtesy. Despite this, the contract with Apple was signed shortly after.

Impact on the Music Industry

This episode highlights the challenges businesses face during digital transitions. As of 2023, digital music accounts for over 80% of global music industry revenues. The evolution of platforms like Spotify and Apple Music underscores the importance of effective tech integration.

Conclusion

Derek Sivers' story with Steve Jobs illustrates the tension between innovation and practice. For tech decision-makers, listening to specific partner needs can make all the difference.

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Steve Jobs Derek Sivers iTunes music industry digital transformation
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