2026-04-03 00:00:52
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.
2026-04-02 23:52:28
I’m not as much as a space nerd as Jason is, but I did watch last night’s Artemis II launch with my wife and son on our Apple TV, and it really brought me back to the shuttle launches of my youth.
My son’s been curious about the progress of the flight, so this morning at breakfast, I pulled up the NASA tracker so we could see where they are, but I found the interface pretty clumsy to use on the phone.
But this is 2026, where people who are excited about something can whip up their own solution. That’s just what accessibility advocate Jakob Rosin has done with this very cool web dashboard. There’s live data from NASA of the spacecraft’s speed and position, a timeline of all the events during the mission, and even audio radar of spacecraft positions that I find weirdly soothing. Definitely worth checking out if you’re keeping up to date on Artemis’s flight, although I do wish it had a visual representation of the spacecraft’s position and route. (That you can find on the NASA interface.)
2026-04-02 21:00:38
Apple has turned 50, and this week I realized that I’ve been writing professionally about the company for two-thirds of its existence. (Excuse me while I try not to turn into dust and blow away in the gentle spring breeze.)
2026-04-02 04:56:55
Last December I complained that Apple was withholding iOS 18 security updates from iPhones capable of running iOS 26, leaving users who didn’t want to upgrade to Apple’s latest OS version yet in some security peril.
Well, I have good news and bad news. The good news: As of Wednesday April 1, Apple is pushing out iOS 18.7.7 to all devices running iOS 18. This update, released last month for devices that were not capable of running iOS 26, is now available even for compatible devices. If you’ve got auto-update turned on but have not gone through the steps to do a full upgrade to iOS 26, this update can be automatically pushed and applied. This is good news, as those who have opted not to run iOS 26 will get to take advantage of several sets of security releases.
Now the bad news: This is happening because of some really bad security breaches like DarkSword and Coruna. As Apple noted in a security update:
We enabled the availability of iOS 18.7.7 for more devices on April 1, 2026, so users with Automatic Updates turned on can automatically receive important security protections from web attacks called DarkSword. The fixes associated with the DarkSword exploit first shipped in 2025.
Now, to be clear, security patches on an older operating system are not as effective as they are on an entirely new system, since a new OS like iOS 26 has all sorts of structural changes made for security reasons. As a new Apple security note says, iOS 26 “contains the strongest security protections.” If you’re very concerned about your iPhone being secure, updating to iOS 26 is going to make it more secure than updating to 18.7.7.
But this does mean that Apple’s patches, which seek to break the chain of bugs that led to serious security exploits, are available to many more people.
Bottom line: If you’re an iOS 26 holdout, and you’re not ready to update your iPhone, at the very least you should update to 18.7.7 and protect yourself from some seriously ugly malicious software.
2026-04-02 04:26:49
In this April 1st edition of the show, Philip Michaels returns to steal the show from Dan and Mikah (and Jason!) and force them to compete for points for their punditry.
2026-04-02 03:17:40
A 50th anniversary is a good time to reflect on your relationships, and it seems lots of people have thoughts about their time with Apple today. I would definitely not be where I am in life without the company, for both good and bad, so here are mine.
Technically, my days with Apple started by playing games on my next-door neighbor’s Apple II in the late 70s or early 80s. When enough time has passed, the exact memories naturally become a little bit fuzzy. It was certainly before I got my own Commodore 64 in 1983, I know that much, but I don’t think I can exactly claim to have been there from the very beginning. Anyway, little did I know back then that I would actually get to house sit for the guy who designed the thing. Foreshadowing.
My best friend’s dad was a university professor from California, and he had brought over an Apple II of some flavor. I don’t remember them being common over here otherwise—the UK had a weird home computer industry all of its own, but this was probably just the perspective of a little kid who only wanted to play video games.
I eventually graduated from my C64 to an Atari STe around 1989, which had many better games than a Mac, and built-in MIDI ports as well. It was also way cheaper than a Mac, and it was totally fine. There was a GUI and a mouse, and those are all the same anyway, right?
Then, just a year later, I started a degree in Computing Science at the University of Glasgow, and back then all the computers in the labs were Macs. Generally, Mac Pluses or SE/30s, with the occasional brand new LC in the second-year labs. And so I used them, and I realized quite quickly that Atari had completely ripped off the Mac GUI, and not exactly done an amazing job of doing so.
I’ve had this experience two or three times in my life with technology, using something and realizing that it’s an inflection point for everything else going forward. The first was those early days with the Mac. Okay, so I was six years late to the party, so you are entirely right to question my definition of “early days.” Still, the user interface was so well designed and thought out, and it just made sense to me in a way that no computer had really done before. System 7 came out shortly afterward and improved everything even more.
At this point, we’d been doing most of the development work for our coursework in THINK Pascal, and I quickly realized I could use that to make my own applications. This history has been covered well, but I wrote the first version of my calculator PCalc in 1992 on my brand new Mac Classic. (Sorry, Atari.) I bought an LC II some time later, probably a month before the LC III was announced. I even fitted it with a maths co-processor! I started working on my application launcher DragThing in 1994.
Again, this is well documented, but I was soon determined to work for Apple. And a few years later, I got my wish, working in Apple’s software engineering group in Cork, Ireland. It was a lot easier to get a job with Apple in late 1996 than it is today, but my existing apps certainly helped me get a foot in the door. However, as I discovered after joining the company and moving to a different country, Apple was actually on the verge of complete bankruptcy.
I’m told that, like with having kids, you block out a lot of the difficult times of your life, and generally remember the good bits. Well, I remember a hell of a lot of bad stuff from those years, so who knows how bad it really was.
Gil Amelio appeared and fired so many people across the company that soon our little engineering group all fit around the one table for lunch. It was an extremely stressful time to be at Apple, but also probably one of the most interesting – I got to witness the return of Steve Jobs first hand, after all. Another inflection point, really.
I worked on a bunch of things while I was there, including the only two things that actually shipped from my less than four years on that team – the Disney 101 Dalmatians and Hercules Print Studios that were bundled with Macintosh Performas. That was enjoyable and relatively low-stakes work. I learned how to program in C++, use a UI framework (Metrowerks PowerPlant), and generally work as part of a team. I was even co-team lead on the Hercules one. However, staring at pegasi all day meant that I did not see the film, and I still have not to this today.
I was then placed on the iMac project somewhat unknowingly, and ultimately the Dock and Finder – the source of all my best Apple anecdotes. Then Steve Jobs happened, I resigned, etc etc. You know how this story goes, I assume. In any case, I met a lot of good people at Apple, some of whom I am still in touch with today. Companies do not care for you, but at least some people do.
In all, it was a relatively short time working there. I was not important in the least, and I did not really do anything of note. I worked on lots of cool stuff that didn’t ultimately ship, sure. Put it this way: I am unlikely to be an entry in any Apple history book.
And I was so relieved when I left. I was 27, and I was young enough then that I didn’t really know how stressed I had been working in that environment. The weight off my shoulders was enormous, even if being an indie developer came with its own set of slightly different artisanal weights. You know how some people have stress dreams about doing exams? I still have stress dreams that I’m back working at Apple.
I did not part from my ex on the best of terms, but it has remained a big part of my life, and we kept uncomfortably meeting up at parties.
I rewrote PCalc again after I left, and through a random pressing of my business card into the hand of one Phil Schiller at a WWDC, it ended up getting bundled with the iMac G4s in the U.S. I probably made more money from that deal (and a weekend’s work to change the app into U.S. English) than I did from all my years of salary at Apple.
I am definitely still in Apple’s orbit, or perhaps just past their event horizon. I am forgetting many things now, including Widgetgate and Lodsys.
And yes, I also ended up getting to know Woz, and stayed with him for many years in a row during WWDC time. We’re still in touch occasionally to this day. It is absolutely wild to me that I know one of the founders of Apple, who basically invented the personal computer. I got to chat to Douglas Adams because of Apple as well – he used DragThing, and I added several features to it just because he asked. Frontier scripting? Absolutely, Mr. Adams, right away, sir.
I’ve also known Jason Snell for something like 32 years at this point, since he was a youth at MacUser, and nowadays have the pleasure of doing podcasts with him at The Incomparable and Relay. So many good friends in my life have happened because of Apple, directly or indirectly.
I’m also, I will admit, doing reasonably well because of them. Then again, Apple is doing pretty well because of me. If I calculate the 30% or 15% of all the sales of PCalc in the App Store, I’ve probably easily paid back my entire Apple salary and all the PCalc licensing fees. But then again, the Apple stock I got in the late 90s is worth a little bit more these days, too, so ultimately I can’t really complain.
Whenever I purchase a new Mac with the money I have made from selling things on the App Store, it does at least make me think how ridiculously circular these things are. A disturbing amount of my lifespan has consisted of moving money slowly back and forth between Apple and me, whether I’m working for them or not. I think I’m currently ahead, but who knows what the future holds. I do sometimes wonder if I never actually stopped working for Apple.
Anyway, DragThing lasted nearly half an Apple, at 25 years. PCalc is still doing well, some 34 years later (I just need to hold on for another eight.) Dice by PCalc is a recent addition, based on my return to playing D&D, but it at least constantly amuses me. I suspect I will still be doing this long after I retire.
So here’s to the next 50, Apple. I do still miss you sometimes.
