advertising | 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.

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.

Apple’s troubling stubborn streak

05/4/21

One thing Apple unveiled in its recent Spring Forward event was enough to make me believe in miracles.

After nearly six frustrating years—six years!—one of the company’s most inexplicable design blunders was finally corrected.

Hello, new Siri Remote.

The shock got me digging into the past to examine Apple’s track record when it comes to fixing things that need fixing. Sorry to say, it isn’t pretty.

Here’s a look back at the more notable Apple mistakes—and how long they went uncorrected.