Missed connections: Me and Apple

Sadly, unlike so so many of my fellow long-time Apple fans, I have no picture of me with my first Mac.

It’s probably just as well. You would not be able to handle the sheer hair of it all. Most of it on me, some of it inexplicably on the Mac. But, for the record, it was an SE FDHD with two floppy drives and an external 30 MB hard drive. I bought it used in 1990.

And I loved it.

I was hooked. It helped that I had just started grad school and could stay up all night playing Shufflepuck Cafe, Shadowgate and Strategic Conquest when I should have been studying.

I continued to buy Apple products throughout the ‘90s — an LC, then a Quadra 610, a Performa 6400, a PowerBook 520c, two Newtons and finally a Power Mac — when everyone in my family was buying PCs. (Now they’re all on Macs.)

I followed Apple rumors like crazy. Apple was working on a game system! A set-top box! Taligent was going to save the company! No, it was going to buy BeOS!

By 2001, it hit me: it was the rumors that were crazy, not me. Most of these people didn’t know what they’re talking about. I could write this stuff!

Hey! I could write this stuff!

So I did. I started writing Crazy Apple Rumors Site. And guess what? Yeah, it changed my life. But it also just led to some funny stories.

The first one I remember is after publishing a story one night (I wrote most of them after coming home from work), I woke up the day to find a message in my inbox from one Phil Schiller.

Normally that would be cool! An Apple executive! Emailing little ol’ me! Wow!

But there was a problem. The piece I had published the previous night was… less than flattering. Because the Enron trials were going on at the time and Schiller had given a speech at the annual QuickTime conference (yes, there used to be a QuickTime conference) that some said paled in comparison to a Steve Jobs show, I wrote that attendees wished Schiller had just pled the Fifth as so many Enron executives were doing.

So, when I saw his name in my inbox I did not think “Wow!” — I thought “Oh, crap.”

To his credit, Phil was extremely good natured about the jab and we went on to exchange emails over the years about various pieces I wrote. Schiller became a CARS staple, launching any number of my patented bad Photoshop jobs. My last exchange with him was to express my condolences on the death of Steve Jobs in 2011.

Some of my ideas were certainly better than others. One piece joked that Apple was introducing “iPorn.” That was it. That was the joke. In my defense, I was very young.

OK, I was in my late 30s. There. Are you happy? I’m not.

To create evidence of this claim, I took a screenshot of Apple’s homepage, added a blurred out pornographic picture to it and posted it with the article. I really could have and should have been doing literally anything else.

The day after posting that gem, the phone rang. Because I had a PowerBook in for repair at the time I was thrilled to see that the caller ID read “APPLE LEG”. If only I’d known what the truncated last two letters were. Instead I naively thought “Ah! News about my repair!” It was not that at all.

When I answered the phone, the woman on the other end identified herself as being with Apple Legal.

Ah. “AL”. Those were the missing two letters. She explained she was calling to demand that I take down the screenshot of their homepage with the porn added, claiming it violated the company’s copyright on the images. Presumably the non-pornographic ones. Upon hearing this, I immediately referred her to my lawyer who informed her of the fair use doctrine and hahaha, no, I folded like a cheap suit. I hand-drew a version of the image and posted that in its place.

(It is now hilarious that one of my current beefs with the company is that it continues to offer up apps that make non-consensual porn. Who says irony is dead?)

There were many other fun stories, including the time I wrote a piece saying that, for reasons unknown, the then 43-year-old Avie Tevanian was going through puberty again; slamming doors, pouting, stomping around the Apple campus and generally making all the other executives miserable. Do I know why I wrote this? I do not. This also prompted contact from the upper echelons of Apple corporate. Tevanian emailed me the next day to point out the big mistake in my article: I got his age wrong. He was actually 42.

But the big story was the one I would not find out the rest of until watching The Talk Show Live from WWDC back in 2019 seventeen years later.

Some time around May of 2002, I got an email from Schiller asking me if I would ever consider coming to work at Apple. As someone who spent way too much time thinking about the company, it was like being asked if you want to move up to The Show. But I live in Tacoma, WA, and remote work was not on the table with Apple. My wife and I were both happy with our jobs and loved living in Tacoma (shut up). So, after sweating it for a bit, I replied that, while I was flattered, it didn’t feel like a move I was ready to take right then.

At the end I quipped something to the effect of “If my situation changes and I’m suddenly really desperate, I’ll let you know!”

What I didn’t know until Greg Joswiak told Apple’s side of this story to John Gruber is that hiring me wasn’t Schiller’s idea. Apparently they sometimes used to pass around my articles at Apple’s weekly marketing meetings and, one time, Steve Jobs read one of my pieces at a meeting. Aloud. After what I’m sure was uproarious laughter, Steve said “That guy’s a pretty good writer. Why don’t we reach out to him to see if he wants to come work at Apple?”

Schiller wasn’t just idly asking me a question about my long-term career goals. Steve Jobs was saying “Hey, dumbass, do you wanna come work here, make history and also a bazillion dollars in stock options?”

And I said…

(this is what I said)….

“Only if I get desperate!”

Well, happy 50th, Apple. It probably wouldn’t have worked out anyway.