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Michael Tsai - Blog - Steve Jobs in Exile
Michael J. Tsai · 2026-05-22 · via Michael Tsai

Geoffrey Cain (Amazon):

Drawing on previously unpublished materials and new interviews with the key players, Geoffrey Cain reveals the untold story of Steve Jobs’s “lost decade”—the formative years that shaped the icon we thought we knew.

With unprecedented access to unbroadcast footage of Jobs in NeXT meetings, private company documents, and interviews with his closest colleagues, Cain offers the definitive account of how failure transformed a brash wunderkind into a true business genius.

John Gruber:

And via Cain’s post on LinkedIn announcing the book, the foreword is by NeXT cofounder Dan’l Lewin.

Joe Cieplinski:

Back in 2013, I suggested the story of Steve Jobs would best be told as a 5-act opera, with the most crucial part of the story being Act III.

Steve Hayman:

Jobs left Apple in 1985, founded NeXT, hired me, bought Pixar, and came back to Apple in 1996 at its historic low point, when Apple was near-death, and orchestrated the turnaround we’ve all heard about.

I’ve bought most of the Steve Jobs books, and seen the movies, but they all seem to treat the NeXT years as an afterthought rather than a transformational time. Sure, the NeXT hardware didn’t sell well but the software set the stage for everything Apple makes today.

Geoffrey Cain:

Today is launch day for Steve Jobs in Exile. I spent almost four years digging into Steve’s stretch in the wilderness -- 1985 to 1997, after Apple pushed him out and before it brought him back.

I expected the record to be complete. What more could there be on the most written-about entrepreneur alive? I was wrong. An archivist at Carnegie Mellon told me I was the first person in about fifteen years to open the NeXT archive. People had been holding letters, tapes, memos, recordings in their closets for decades, waiting to show someone. More than a hundred of them sat down with me.

He did a Reddit AMA.

Jason Snell:

It’s a surprising and sometimes gruesome (in a businessy way) story that does not show off the famous man at the center of the story as much as depict all the ways he failed in what turned out to be preparation for his career-defining role as Apple CEO. (I also got to interview Cain about the book this week on Upgrade.)

[…]

The computer that NeXT ended up building didn’t satisfy the requirements of those original higher-ed buyers who were the target market. Jobs had followed his bliss, and his good taste, in interesting directions. NeXT made an interesting product. But the product failed at being a successful product, just as NeXT kept failing at business.

And it just keeps happening, as the book details. Early investor and Jobs believer H. Ross Perot (yes, the former independent presidential candidate!) had ties in the government that would’ve allowed NeXT to sell computers to America’s intelligence agencies, primarily for spy-satellite image analysis. Jobs refused the lifeline, saying he didn’t want to do business with the government.

A deal with IBM had the potential for NeXT’s operating system to take the ecological niche of Microsoft Windows before it had been firmly established on the world’s PCs. Jobs decided he was uncomfortable working with IBM.

See also: Becoming Steve Jobs.

Previously:

Update (2026-05-29): Steve Hayman:

The book has tons of great stories and behind the scenes info; I certainly recognized a lot of the names, but many of the tales were new to me.

Update (2026-06-08): Marcin Wichary:

I do not see this as a book of new immense insight, technical depth, or design details, but that doesn’t mean it doesn’t go beyond surface level. What I appreciated most was Cain not shying away from pointing at some of Steve Jobs’s mistakes: hiring wrong people he happened to like, almost driving the company to the ground through obstinance, inability to focus on things he considered uninteresting, and a profound dose of duplicity coming into the NeXT/​Apple merger.

Other things that stood out: focus on people around Jobs, spotlight on Jobs’s disappointing moral flexibility around working with government (or befriending Larry Ellison, for that matter), and a really fun pizza ordering story that serves as a prelude to the Starbucks call during the iPhone 2007 keynote.

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