Blog | Ken Segall

Steve Jobs: “Your presentation is pedantic and boring.”

09/19/25

It wasn’t one of Steve Jobs’ longer emails. Just six brutal words, rattled off as easily as he might say, “Have a good day.”

The lucky recipient? A former colleague from my time working on the NeXT business long ago. After the success of iMac, he had sent Steve a presentation with a “big idea” for Apple and eagerly awaited the reply.

Safe to say, this wasn’t the reply he was hoping for.

Having seen his less-than-stellar enclosure beforehand, I can’t say I was surprised. What he received was a classic Steve-mail, concise and blisteringly honest. Such communiqués were kind of entertaining—as long as they weren’t directed at you.

Apple’s momentary lapse of reason

05/12/24

Honestly, I never thought I’d hear today’s version of Apple say such a thing: “We missed the mark with this video and we’re sorry.”

Then again, the natives don’t usually show up at Apple’s door, pitchforks in hand. However forced the apology might have been, kudos to Apple for respecting customers enough to admit its error.

That said, given that Apple “missed the mark” by a few light years, it’s fair to ask: How the hell could this even happen in the first place?

Behind HAL: Apple’s last Super Bowl ad

02/13/24

Two days before Super Bowl LVIII, The New York Times reminded us that it ‘s been forty years since Apple made advertising history with the 1984 Super Bowl ad introducing Macintosh.

This year also marks a related milestone—it is the twenty-fifth anniversary of Apple’s last Super Bowl appearance, built around the menacing computer from 2001: A Space Odyssey. By no means was Apple’s HAL a 1984-sized triumph, but neither was it a Lemmings-sized disaster. It was a spot that Steve Jobs was very much proud of, and had no regrets spending millions to run on the Super Bowl.

With the Big Game’s thrills still hanging in the air, I thought this was a good time to re-publish the story I wrote seven years ago. It’s the story of Apple’s HAL, from start to finish, and a bit beyond. If you have the time—and trust me, you’ll need it—it’s a fun bit of Apple history. Enjoy!

Drawn: a feast for eyes & brain

01/31/24

Welcome to the first book review I’ve ever written. Likely, it will also be my last. Not my thing, really.

Today I am moved to masquerade as a critic only because I finished my final reading of Drawn, by illustrator Craig Frazier, and I’m in awe. I say “final reading” because I probably have at least twenty readings under my belt by now. I was the editor.

I assure you, this does not make me a biased reviewer. I’m a believer in truth (see my tagline above), and I’d be very bad at faking enthusiasm.

I first met Craig when I approached him about creating the cover design for my book, Think Simple. I had already been smitten by his “visual wit” and delightfully odd way of looking at the world. There was always something “off” in his illustrations that demanded further inspection.

Apple’s scary event: a B-team production

11/4/23

You never knew exactly how Steve Jobs would react when you presented a new idea. The only thing you could count on was his brutal honesty.

But, even if he rejected the work, all was not lost. It was simply part of the process. Steve knew that creative work is often iterative, so we’d keep at it until we arrived at a place we all loved. It was a process that actually deepened our relationship over time.

That said, one meeting is seared into my brain because Steve made a particularly biting comment. Not seeing anything he liked in a range of work, he said, “Oh, so you put the B-team on this one.”

Ouch.

In those few words, he questioned how seriously we took the assignment, not to mention our ability to see the difference between “great” and “good enough.” Message received loud and clear. An error in judgment never repeated.

This memory came to the fore because that’s exactly how Apple’s Halloween Eve event made me feel—like the assignment had been relegated to the B-team.

2023 iPhone event: Was that real or AI?

09/25/23

Okay, it took me forever, but I finally got around to watching the 2023 iPhone event.

Why so long? It’s all Apple’s fault. The more they announce new products in these prepackaged events, the less I feel like watching.

My viewing did not change my opinion of virtual presentations. Instead, in an odd way, it got me thinking about the power of AI. Not that Apple used AI. to generate the script—rather that AI could have written the script, and few would have noticed.

That’s because what Apple is doing is exactly what AI is so good at. They’re writing a script based on the show before. And the one before that. And the one before that. They’re stuck in a loop where a parade of presenters describe new products, minus any emotional connection.

ChatGBT wouldn’t break a sweat pulling that together.

Bill Gates’ fanciful memory

06/2/23

Love or loathe Bill Gates, one must admit—the man is a part of technology history. His lifetime accomplishments are many.

Which makes it all the more inexplicable that his inner Santos insists on some outlandish resume embellishment.

Weighing in on AI with his blog article, The Age of AI has begun, Bill puts AI in context. He sees it as one of two revolutionary demos he’s seen in his lifetime. This is how he describes the first.

“[It] was in 1980, when I was introduced to a graphical user interface—the forerunner of every modern operating system, including Windows. I sat with the person who had shown me the demo, a brilliant programmer named Charles Simonyi, and we immediately started brainstorming about all the things we could do with such a user-friendly approach to computing. Charles eventually joined Microsoft, Windows became the backbone of Microsoft, and the thinking we did after that demo helped set the company’s agenda for the next 15 years.”

Impressive! Who else but Bill Gates could spot the potential in this graphical interface thing and develop the software to help us do all that amazing future-y stuff?

Oh, right. That other guy. Steve something-or-other, was it?

This calls for some serious fact checking. So I now turn to our dependable old friend, Reality.

Apple & Jony: a make-believe ending

09/6/22

Everyone loves a good story. Some people need a good story.

Tim Cook, for example. When Jony Ive decided to leave Apple in June 2019, Tim’s job was to reassure Wall Street that the departure of Steve Jobs’ spiritual partner was only a superficial wound.

The goal was believability, not transparency. After all, this is business. Very, very big business.

And so a story was spun.

Let’s give Tim credit for manufacturing a credible and effective tale. Then let’s wonder why no one ever poked holes in it.

The 27-inch iMac conundrum

03/16/22

Allow me to speak on behalf of the world’s 27-inch iMac owners:

THIS IS AN OUTRAGE!

Ah. Good. Had to get that out of my system. Honestly, I have never been so appalled at an Apple strategy. Between the launch of Mac Studio and the simultaneous death of iMac 27, we who have so patiently waited for an Apple Silicon-powered 27-inch iMac are suddenly left with only two options.

We can hang onto our aging computers and simply hope that a new iMac 27 will one day appear. Or we can spend more than double the cost of a typical new iMac 27 for a Mac Studio + Studio Display.

There are only two ways to explain what Apple is doing. It is either failing the transparency test miserably, or it is blatantly committing an act of corporate greed. Sadly, “all of the above” is also a possibility.

Attack of the lame headlines

10/1/21

As a rookie copywriter struggling with headlines, my mentors warned me about two unforgivable sins.

One was trying too hard to be cool. The other was stooping to such overused tricks as puns and rhymes.

I rarely think about those days anymore, but every so often a headline grabs me by the throat and demands to be ridiculed. I, of course, am happy to oblige.

It happened right after the recent Apple event when I visited apple.com to learn more about the new iPhones.