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Chris Espinosa was just a precocious kid when he started working at Apple. He has kids of his own now, he’s still at Apple, and he has some great memories.

Paul Freiberger and I are currently writing the third edition of Fire in the Valley, our history of the personal computer—to be published by The Pragmatic Bookshelf, naturally. As we go back over the material, we keep finding threads that run through the whole narrative. I am sharing some of these as brief history articles here in PragPub.

This time I want to share the story of someone who has had a close-up view of Apple throughout its entire amazing history: Chris Espinosa.

The Veteran: 1996-the present

In the run-up to the iPhone release, Chris Espinosa had been tasked with bringing the Xcode development environment up for this new platform. Except that nobody told him that that was what he was doing. “They just said, ‘Here’s the processor architecture. Here’s what you need to do, and we’ll tell you when you’ve done it right.’”

It had been different before. Once Steve returned to Apple, Chris recalls, the company became “stovepiped and compartmentalized.” He was used to working very broadly at Apple, talking regularly with people in marketing and sales and support and software. Now he “would go for months without talking with somebody outside my local organization.” It wasn’t bad, but it was different.

He’d had more access to Steve back then, too. Now he’d run into him at lunch once in a while. He introduced his son to Steve. Steve was always congenial, but there just wasn’t much interaction. Which was fine with Chris. Things had been pretty intense in the early days. Now he was enjoying his relative anonymity, working in developer tools.

Then one day he got a call.

It was the day before the iPhone shipped, and Steve had scheduled a big employee communication meeting to celebrate the event. When the phone rang in Chris’s office, he picked it up and the voice on the other end said, “Please hold for Steve.”

Chris held.

It turned out that Steve was calling to get Chris’s thoughts on the iPhone. “This iPhone,” Steve said, “What do you think of it?”

Chris was flabbergasted. He had to admit that he hadn’t touched one. The release had been extremely secretive, and he’d watched the announcement along with the general public. But he realized that he had an opinion. “From everything I know about it,” he told Steve, “it’s the best thing we’ve ever done.”

Steve thanked him and they chatted some more, and the call ended and Chris went back to work. And when the company-wide memo from Steve came out announcing the meeting, it said that Steve thought the iPhone was “the best thing we’ve ever done.”

The Professional: 1984-1986

It meant a lot to Chris that Steve had turned to him for confirmation that he wasn’t blowing smoke about the iPhone. Chris remembered how it had been two decades earlier. As a brash kid in a company where anybody could talk to anybody, he had played the role of court jester to Steve. “After we had shipped the Mac and were trying to do the Macintosh Office—the server, the laser printer,” he remembers, “[Steve] really wanted to believe rosy scenarios, and he pushed people to [promise] things that were unachievable.... It was basically what he lost his job over.” And Chris was calling him on all of it.

Somebody needed to. For the first two years of the Macintosh’s life, it failed to deliver the sales Steve had projected. The aging Apple II was keeping the company alive.

When Steve got pushed out, Chris hung in there. Apple had always been more than a job to him. He now had relatives also employed at Apple, in the Apple II division. He stuck it out through a succession of CEOs and ups and downs. He watched John Sculley put out the immediate fires, and saw the desktop publishing revolution gave Apple a huge boost.

“We were making 55 percent gross margins,” Chris recalled, “on our way to becoming a 10 billion dollar company. We were in fat city.”

But the deeper problems at Apple couldn’t be papered over. The company lost market share. Its product line lost focus. The operating system was showing its age. And there was no powerful vision driving decisions. By the mid-1990s it was widely assumed that Apple would be bought by another company. Sun Microsystems made an offer, but it was rejected. Before long, Apple was bound to get an offer it couldn’t refuse.

Chris had never had a job outside Apple, and he wasn’t looking for one now, no matter how bad things looked. He would hang on for the endgame. He told himself he’d “stick around to turn out the lights.”

The Kid: 1975-1984

Of course things didn’t work out that way. But Chris couldn’t have predicted that back then. He couldn’t have predicted any of Apple’s remarkable story, and he arguably had more perspective on it than anybody else.

It had begun when he was just 14 years old. That was when he and Randy Wigginton would catch a ride to the Homebrew Computer Club meetings with Woz. Soon he was hanging out at Woz’s place with Randy, where Woz let then write programs for his prototype Apple II. Or he’d spend time in that new store that sold computer stuff, the Byte Shop.

That was where he’d first seen Steve Jobs. It was Steve who had hired him to work at Apple, impressed by the demo program running on the Apple II and even more impressed that it had been written by this little kid. Steve was different from Woz, though. Chris always had the feeling that Steve was shaping him.

He never really left Apple, even when he went to college. While there, he spent his free time writing the official Apple II manual.

It’s been a long time since he was that kid riding his moped to work to write software or demo the Apple II to people who walked into Apple’s office. Now he has kids of his own, and one of them just got back from summer camp where he was writing code using Xcode, the development environment Chris and his team built.