My turn: Apple at 50

Now living the free and easy lifestyle (other than the stress that comes from, well… everything), it seems I missed the memo stating that April 1, 2026 is the day to tell a personal Apple-related tale or two in celebration of the company’s 50th anniversary. I’m on it.

Breaking the first iPod

Over at Six Colors, former Macworld editor Philip Michaels relates his most awkward encounter at Apple. In that encounter he tells how he commissioned “a more physically active colleague” to put the very first iPod’s durability to the test. I appreciate his attempt to provide cover for that colleague (me), but I’m fairly sure I have the statute of limitations at my back.

He tells it true when he says that given Apple’s portrayal of the iPod as a solid workout companion, it made all the sense in the world to see how much abuse it could take in the form of juggles and oopsies. And, again as he tells it, that took the form of me dropping it while jogging (twice) and letting it loose from a bicycle traveling at approximately 5 MPH (once) and again at approximately 15 MPH. It continued to function after the first three drops — though certainly dinged up with the back case starting to separate from the front — but the fourth did it in in spectacular fashion. The thing just flew apart, scattering pieces everywhere.

I gathered the pieces into a nearby plastic sandwich bag, wrote up my experience (the story appeared in print but apparently never made it online), and thought nothing more about it other than, while a worthwhile test, it seemed like a waste of a perfectly good iPod.

A couple of weeks later, I got a message from Phil saying that Apple would like its iPod back.

“You know it’s in pieces right?”

“I do. You need to talk to them about that. Tell them it was my fault.”

Apple’s product loan representative called and explained that the first iPod models provided to the press were not meant for release to the general public. Apparently there was some part in there meant for Apple internal use only. She kindly offered a working iPod once the one I had was returned.

“Um, well, I will certainly send it back. But, you see… it’s broken.”

“Broken? How?”

“I dropped it.”

“You dropped it.”

“A lot.”

Pause

“How did you do that?”

“Jogging. I also threw it off a bicycle. Twice.”

Longer pause

“Why?”

At which point I explained my assignment using my best This Is A Perfectly Reasonable Thing To Do voice, taking pains to throw Phil under the bus, as instructed.

“So you intentionally destroyed the iPod.”

“I did. Yes. But hey, it held up really well! Does that mean I can’t have the new one?”

Very long pause followed by breathy sigh

“Okay, but only if you promise not to break it.”

“Deal.”

And she was as good as her word. I returned Bag o’ iPod and received a replacement some time later. Much as people suggest that doing things like this put you squarely on Apple’s Naughty list, the company was never shy about loaning me hardware when needed.

Taking umbrage at Macworld Expo

For a number of years I was responsible for setting up and hosting speakers and events at the Macworld booth at Macworld Expo. The job required me to line up industry luminaries to be interviewed by me or members of the Macworld staff, host product and tchotchke give-aways, meet and greet readers, and in later days, oversee podcasts.

Typically the show floor opened during the Apple keynote, which meant that I had to miss several of them that I would have otherwise attended. One year I discovered that Apple’s QuickTime team was streaming the thing for the purposes of testing what could be done with its existing technology. I managed to access the stream and dutifully projected in on the booth’s big screen. Folks who were also pinned to the show floor gathered to take a look. Given that these were very early days for streaming, no one should have been surprised that it looked and sounded awful.

While going about my business at the booth’s podium, a young man in a purple QuickTime shirt rushed up and shouted “Turn that off! Turn that off!!”

“And who are you?” I asked.

“I’m with Apple and the QuickTime team! This isn’t for you to show. Turn it off, now!”

Running the booth was always stressful for me and, when stressed, I will occasionally jettison my manners.

“You’re the ones who chose to show this and make the link public. If you don’t like it, make your stuff work better.”

And he glared. And he pouted. And he turned on his heel in what can only be described as an “I’m gonna tell Steve on you!” kind of way.

And I went about my consequence-free business.

My work on the big screen

Hard as it is to believe now, at one time people wrote books about technology of the day — operating systems, the capital-I Internet, coding schemes, and even hardware destined to be outdated in a year. Very shortly after the release of the first iPod, I was approached by an editor at Peachpit Press who asked if I’d be interested in writing a book about the iPod. Always hungry for work, I said “Sign me up!”

But sign me up for what? The iPod was one of the most intuitive devices around. Yes, syncing to your Mac (as it was Mac-only at the time) could occasionally be glitchy, but as designed, it just worked. What to write about that wasn’t already on Apple’s website or in the printed documentation (another thing that used to be)?

Putting our heads together, editor Cliff Colby and I came up with the idea of there being “secrets” about the iPod. Some of it was a description of the features and simple retelling of how to successfully sync the thing (and what to do when it didn’t work as expected), but there were other bits as well — an illustrated teardown with callouts that might possibly have been accurate, setting up and using the iPod as an emergency boot drive, connecting the iPod to other devices you own, and so on. Not rocket science, but useful at the time.

As was the practice of the day, the book was written and published very quickly in the hope that it wouldn’t be out of date for at least six months. It was the first book written about Apple’s diminutive music player and the first book I’d written that actually paid out.

Months go by and, once again, I’m seated at a Steve Jobs keynote. Typical of Apple keynotes of the time, Steve begins by recounting Apple’s successes over the past several months — sales figures, quotes from positive reviews, and glowing overviews of the latest Apple products.

During his recap of the iPod he boasts of the rich ecosystem growing up around the device. Images of cases, adapters, and speakers flash across Moscone Center’s big screen. He then pauses, and says something like, “Even this.”

And up pops the cover of Secrets of the iPod.

And it remained as he shrugged and waited for the laugh. Which was, according to my admittedly biased recollection, muted.

Fair enough. For a very brief time, I’m Steve Jobs’ punch line. Rather than think, “Jesus, I just got owned by Steve Fucking Jobs!” I thought, “Jesus, in the tiniest way possible, Steve Fucking Jobs is aware of my existence!”

Such was the power of the man.

It all comes back to Apple

You’ve undoubtedly read countless origin stories from those who’ve covered Apple for decades. I have mine as well, which is largely a series of happy accidents.

I was a professional musician, making my living playing piano around the Bay Area. I had a band called System 9 (I still do) and was first shown the Mac in a musical context. A member of my band worked at a store called ComputerWare, where he used his employee discount to purchase a Macintosh 512Ke. On it, he ran a music sequencer from Mark of the Unicorn called Performer. He brought his Mac into rehearsal and showed me how you could record and edit music via MIDI. I was blown away and when, months later, he offered to sell me his Mac (he was upgrading to a Mac Plus) along with a MIDI interface and copy of Performer, I leapt at the opportunity.

I became obsessed with it.

Meanwhile, my girlfriend at the time was working as a copy editor at MacUser magazine. Sitting in her cubicle one day, she heard editor Jon Zilber ask the room at large if anyone knew someone who could write about MIDI and the Mac. When no one replied, she meekly answered, “My boyfriend is a musician and he uses MIDI.”

“Can he write?”

“Well, he wrote for his high school newspaper.”

“I’m that desperate. If he can write up two acceptable pieces for these MIDI programs, I’ll give him $50 each.”

I stayed up all night writing the pieces and saved them to a floppy disk, which Claire carried to the office the next day. I got the 100 bucks and my first pieces were published in the November 1988 issue of MacUser magazine.

Even in those green days, I knew that a music career was anything but secure and I therefore scrutinized any reasonable side-hustle that came along. Pipe dream though it seemed, writing about technology was one such potential path forward.

So I hustled, and cajoled, and pitched, and produced over and over and over again until I eventually earned a column and Contributing Editor title in MacUser. When MacUser and Macworld merged, I pushed for a place at the table, which happened thanks to those who thought I had something to offer.

After years of covering Apple (and one too many Macworld layoffs), I decided it was time to see Apple from the inside rather than simply observe it from a distance. I couldn’t be happier that I did.

And all this because Steve Jobs, Steve Wozniak, and countless others designed a computer for the rest of us. It absolutely changed the course of my life.