David Shayer worked at Apple for 14 years, and he has a wild experience to share. Apple has a unique culture, and David will give us an insider view of what it was like for him at Apple during the 2000s, roughly between 2001 to 2015 when Apple transformed into the powerhouse that it is today.

David worked as a Software Engineer but for the hardware organization with Apple. He worked on a few special projects at Apple: at least one of them was top secret. But he is also going to share the struggles of building file systems and working on really short timelines and having development plans upended by Steve Jobs.

Steve Jobs Evaluation

Adam: As the iPod sold more units, it started attracting more attention and David’s teams work started being directly evaluated by Steve Jobs.

David: There was a period in the early 2000s when Apple was mainly known as the iPod company, before the iPhone shipped. And Steve was intensely interested in the software, but of course, mostly the user interface level software, right? I mean, he didn’t care about the file system, as long as it worked. It wasn’t his interest. He wanted to know what do the apps look like on the screen? I was in the group that wrote all those apps. My boss would have a weekly meeting with Steve and he’d go and show him what we had worked on. And usually he had questions like okay, there’s several different ways we can go working on this photo’s app or this notes app, what should we do? And sometimes Steve would say, Oh, this is terrible. This is good. You should do more of that.

But often Steve would do something totally different. I remember my boss would come back from his meeting with Steve. We’d all be huddled around his office, waiting for him to come back to find out what did Steve say? Because this determined the direction we were going in for the next week. He had gone in expecting Steve to say, did he like these screens we had done for the new player screen that showed you what song was playing. And instead Steve had spent the entire meeting going into the preferences panel and just tearing it all up and saying, I don’t like this. I don’t like that. I want you to rewrite all the preferences. And the preferences had already been shipping for two years. We thought it was all settled.

My boss come back. He’d be like, well, guess what we’re doing this week? We’re rewriting all the preferences, I guess we’ll see if we can get some closure on these other items next week.