How I almost worked directly for Steve Jobs

How I almost worked directly for Steve Jobs

This isn’t a very exciting story but definitely an interesting what-could-have-been thought experiment.

The job

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 this habit that started a chain of events that led to my life almost being very different.

Back to Address Book. Steve had a very, very large address book because of all the notes he kept from phone calls. At that time in Apple history, two things conspired to make this a problematic practice on Steve’s part:

  1. People used what were called “network home directories”. Essentially, the operating system and applications lived on your local hard drive but your own data lived on a network server somewhere. This would inevitably lead to things behaving more slowly, but provided the advantage of portability. Steve could log in from Apple, Pixar, and home and his data would be ready for him.
  2. Address Book was designed at the time to have a single database file that would save in its entirety every time a single change was made. Normally, this was not an issue as most people don’t have much data in their address books and networks that employees encountered were relatively fast.

The issue

So, here’s the issue that Steve faced. Every time he replied to a message in Mail, it would hang for a really, really long time. Many seconds. More than 10 seconds. A frustratingly long time. The reason this happened is this:

  1. Information about people you recently sent email to was stored in the Address Book. Whenever you hit reply, it would record the time you last wrote to the person to use that later for auto-completion
  2. Since Steve and many people used network home directories, the first thing that would happen would be the entire Address Book database would write to the network
  3. Due to the abnormally large address book Steve had, this significantly worsened the problem
  4. Finally, Mail was architected poorly such that this writing out of the Address Book database cause the application to hang

Not surprisingly, Steve was frustrated and let Robert and his admin know as often as possible that this needed to be fixed and soon. I started to get far too used to seeing “Office of the CEO” on my phone as Robert was calling me from Steve’s desk. Once I was on a conference call while Steve’s admin yelled at me for several minutes.

It was risky to make a major change to how Mail worked and it would also take time so that wasn’t an immediate solution. I hope Robert will forgive me saying this, but I did offer a solution early on but he had other avenues he wanted to pursue before following my advice. In fairness, my solution would have made Steve’s setup require more hand-holding.

Eventually, Robert got dismissed from his job. I think this may have played a part in it, but I can’t say for sure.

The next step

But it did lead to an interesting development. Robert contacted me in late 2003, during my last year on Mail, and thought I might be interested in being his replacement. Wow. The only reason I wasn’t completely terrified was because, in my support background, I was often assigned to high profile clients, sometimes going to their fancy houses to fix their issues.

At this point, I had to step back and consider the point in history. Apple was just barely turning the corner, the iPod was only 2 years old and the iPhone was not yet under development. Steve had been diagnosed with cancer just one month before but it was considered to be a resolved matter.

I loved my job on Mail but this was one hell of an opportunity so I had to take it seriously.


So, I did some interviews. A couple of them were actually with people that did the job in the past and others were people that played supporting roles. I was intrigued that most people described the job as not as high stress as you’d imagine and that the hours were relatively normal.

I suppose this was the “new Steve Jobs” that was more respectful and less unfairly demanding of his employees. I couldn’t find anyone that could say a bad word about the job. One person got fired after a brief stint because he had not been making planned backups of Steve’s system and he lost data. Now there’s some stress!

The last two interviews got scheduled, the first was with Steve’s admin. Hopefully she wouldn’t remember yelling at me or would have a sense of humor about it. The second was with Steve.

I felt confident at this point. I’ve always handled interviews well and never got nerves in front of people that most people do. Interestingly, I’m petrified of speaking to a group.

The end

Then the rug got pulled out from underneath me. Someone that had been Steve’s support person in the past came out of the wordwork and was hired instantly. Steve trusted him and there was a track record there. I knew the guy and honestly felt very outclassed. It was a good move.

But can you imagine what my life could have been like and the stories I could have told.