In May 2003, Apple invited me to Cupertino to discuss getting CD Baby's catalog into the new iTunes Music Store. Steve Jobs personally pitched 100 indie labels, saying Apple wanted "every piece of music ever recorded." But their software required manually re-ripping and typing data for each CD — impossible for our 100,000 pre-ripped albums.

I signed the contract, built a delivery system, and charged $40 per album. 5,000 musicians paid, generating $200,000. Competitors like Rhapsody and Napster quickly signed on, but iTunes stalled for months. Then in a keynote, Jobs dismissed services charging $40 to distribute amateur music — clearly targeting me.

I refunded all $200,000, made distribution free, and removed iTunes promises. The next day, Apple returned the signed contract. We uploaded immediately, but I never again promised what I couldn't control.