Here’s One Reason You Should Read Ken Segall’s New Book, “Insanely Simple” [Review]


Ken Segall, photo @Doug Schneider.
Ken Segall, photo @Doug Schneider.

Here’s the most pared-down review I can manage of Insanely Simple: The Obsession That Drives Apple’s Success by Ken Segall.

If you wonder what it was like to work with Steve Jobs: read it. You’ll enjoy it.

Not to be Complex about it (Segall capitalizes the term in opposition to Apple’s Simplicity philosophy throughout the 200-page offering), but here’s the more articulated reasoning behind why you’ll probably like this book.

Segall, the man behind the iMac name, is an advertising exec who worked closely with Steve Jobs for over 12 years, with stints at NeXT and Apple. He named the iMac and worked on the iconic “Think Different” campaign, including getting Jobs to narrate the first version of the “Crazy Ones” above.

That decade plus of experience left Segall with tons of notes, now preserved as a stack of CDs, about what happened in those meetings. (You can read more about his adventures at Apple in our Q&A and read an exclusive excerpt of the book here.)

The times Jobs bounced participants from meetings who didn’t belong there (file under “the small groups of smart people” practice), dismissed people who bored him with PowerPoint presentations and responded to threats with variations of “f*ck ’em” and a roguish smile.

This sounds like familiar territory for readers of Walter Isaacson’s blisteringly honest bio of Jobs — or indeed for readers of Segall’s blog, which shares some of these anecdotes — but here, instead of trying to make sense of Jobs’s complex personality, we’re focused on how he kept things simple at Apple to get the best results.

For some, it may seem too simplistic, or a study in confirmation bias, to decree Simplicity as the only common thread running through Apple’s history that made it such a success. But if you’re curious about Jobs and the way he worked, the stories in Insanely Simple provide ample food for thought. I’ll refrain from spoilers, but if you read through it on your commute or next plane trip, Segall’s straightforward prose will hold your attention and provide some laughs.

The book is somewhat larded down with a “Here’s how you, too, can be like Steve” angle that feels forced compared to Segall’s amiable storytelling style. And, as enjoyable as it is to compare Segall’s Dilbertesque tales of working with Dell, Microsoft and Intel, unless you’re the CEO of your own company, using “brutality with style” by following mantras such as “Blunt is Simplicity, Meandering is Complexity,” and smacking your co-workers or betters with the “simple stick” probably isn’t the best way to keep your job.

Still, the insider tales of his late night convos with Jobs and the rocky ride of some of the failures make it an entertaining read.

Insanely Simple: The Obsession That Drives Apple’s Success by Ken Segall.


  • phillip63next

    No one should dispute that ‘simplicity’ is one of Apple’s guiding principles, and Segall is certainly entitled to write a book about Apple or any other subject he pleases.

    But readers should be aware that the author greatly exaggerates his involvement with the brand and his contribution to its marketing legacy.

    Frankly, it’s been sad to watch opportunists come out of the woodworks following Jobs’ passing. They shamelessly inflate whatever limited association they had with Apple and attach themselves to the brand in order to make a quick buck and shine their own star.

    Maybe it’s just me, but it would be interesting to hear from the people who were actually behind Apple’s decades-long marketing streak.

  • GregE


    I actually worked with Ken in his Apple days, and I know for a fact that he worked closely with Jobs, invented the “i,” etc. That doesn’t qualify him to write a book? You’d rather read books by journalists who never even met Steve? Ken is smart, talented and honest. If you’re looking for villains in this world, I’m sure you can do better.