Tim cook | 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.

AirPower: a fiasco beyond imagination

04/1/19

If there was a Beginner’s Guide To Corporate Screwups, surely it would explore the tried-and-true ways for companies to shoot themselves in the foot.

Release buggy software. Fail to protect customer data. Run a bad ad. See your CEO arrested. So many possibilities!

But AirPower is not your stereotypical screwup. It’s something far grander. Never in history has Apple announced a product, gone silent about it for 18 months, and then killed it before it ever shipped.

At least it proves that Apple can be a true innovator in the area of self-immolation.

“Freedom to fail” is actually a liberating thing, essential to the Apple culture. In an internal meeting, I once heard Steve Jobs defend Apple’s large cash reserve by saying, “It gives us the freedom to jump as high as we want. If we fail, we will always have solid ground beneath our feet.”

Unfortunately, AirPower isn’t the “liberating” kind of failure. It’s just shocking and sad.