This isn’t a very exciting story but definitely an interesting what-could-have-been thought experiment.
When I worked in AppleCare in 1999, I worked with an engineer named Robert Esker. Years later, he became the technical support person for Steve Jobs. At the time, Steve was CEO of both Apple and Pixar and also kept a home office.
Robert’s job was to keep everything running smoothly and travel between all three locations as needed. He wasn’t on his own as there were people across the company that were familiar with getting the occasional contact from him to help resolve an issue with Steve’s systems.
As the support person for Mail, I was one of those people that Robert would contact. Unsurprisingly, Steve was a very heavy Mail user and also used Address Book (which I worked on as well) to keep notes for every phone call he made. It was … READ THE REST