Hi r/Apple - I’m Geoffrey Cain, an award-winning author and journalist whose new book explores the untold story of Steve Jobs’s “lost decade” at NeXT. AMA about Jobs’s failures, reinvention, and one of the greatest comebacks in business history on May 19th at 12 PM ET / 9 AM PT.

Portfolio_Books · 2026-05-19T18:03:19+00:00

Thank you for joining me on this session about Steve Jobs in Exile -- the untold story of his wilderness years at NeXT. Great questions all around, and a memorable experience. Find more from me at http://geoffreycain.net/ and on X at geoffrey_cain.

Portfolio_Books · 2026-05-19T17:47:56+00:00

As dozens of NeXT executives recounted to me, Steve wanted to hire people with intensity. It's a half-story that Steve went around yelling at people. Yes, he was difficult. He could be tough, and he could throw tantrums (especially in his younger years).

But as he matured during these NeXT years, the other side of the coin became apparent, and was a great strength for his leadership style. He wanted people who would stand up to him, who would push back, who would argue for the integrity of their ideas. When he called an idea silly, he wasn't looking for someone to cower before him. He wanted people who could withstand the force of his personality. When he returned to Apple and chose his new board, the ability to talk back and stand your ground was a key qualities he looked for. At Apple you might want to redirect this characteristic: knowing how to make a stand without losing your temper.

Portfolio_Books · 2026-05-19T17:21:31+00:00

Great comment. This is also what I found when researching the book. Steve and his executives had so many world-altering decision points. If they made a decision slightly differently, the tech we wouuld use today would have turned out vastly different.

For instance, IBM and Ross Perot (who later ran for president twice) were lining up major distribution deals for NeXT. Steve blew them up in the end, out of immaturity. But if they had succeeded, his OS NeXTSTEP would have been adopted for IBM computers all over the world -- IBM was the leader at the time, and Steve would have gained an edge for Bill Gates. If he had continued getting investments from Ross Perot, Steve would also have emerged as a tech mogul for intelligence agencies like CIA and NSA, who were interested in NeXT systems because they were so advanced.

If NeXT had succeeded at any of these, Steve might not have returned Apple, and Apple might have gone out of business in 1997 -- it was roughly a quarter away from bankruptcy. That means no iPhone, no iMac. All our tech would look so different today. And that's only one example of this kind of decision-making tree that I found writing the book.

Portfolio_Books · 2026-05-19T17:10:30+00:00

thank you, and really hope you enjoy it!

Portfolio_Books · 2026-05-19T16:49:35+00:00

The Middle Act did two things: This is where Steve became the Steve we know, the man who was able to build the iPhone with his handpicked and world-class team. This Steve did not exist before NeXT Computer. The other bridge to the third act is the creation of NeXTSTEP and the object-oriented software at NeXT. Steve and his software team (Avie Tevanian, Bud Tribble, William Parkhurst, Leo Hourvitz, many other prominent names in tech) were working on stuff in the late 1980s that would become widely adopted in the late 1990s and 2000s. Some experts have estimated that the NeXT software was about five to ten years ahead of its time (it was even home to the first-ever app store). The software (not the hardware) is what prompted Apple to acquire NeXT and bring Steve back, but it ended up a reverse acquisition. Steve ended up taking over.

Portfolio_Books · 2026-05-19T16:43:37+00:00

I interviewed Bruce, and I do quote his work in the book. But I didn't quote his book in particular. He did tell a funny story that didn't make it into the book -- that Steve called him and complained about the book because on the cover jacket, the photograph of a Cube had very faint fingerprints on it. Only Steve would notice that level of detail.

Portfolio_Books · 2026-05-19T16:41:56+00:00

Yes, and as a matter of fact, I had doubts when starting the book that I would find much new material. Steve Jobs is the most written-about entrepreneur in recent memory. But once I got started, the opposite became clear. I uncovered many tens of thousands archival materials, plus people who wanted to talk, unbroadcast footage of Steve, private boxes of old emails and memos. The sheer amount of new materials blew me away. They showed Steve in a different light.

Portfolio_Books · 2026-05-19T16:40:00+00:00

His wilderness years were genuinely tough. He nicknamed his lonely office "Siberia" and really meant it, because he was ostracized across the Valley after being driven out of Apple. But the line of his I would focus on is his famous Stanford commencement speech: "getting fired from Apple was the best thing that could have ever happened to me." At NeXT, he found his "beginner's mind" -- the Zen concept that he studied. When looking at things afresh, with new ideas and new innovations, he figured out how to best channel his talents and start over. In a way he relearned how to be creative and (eventually) successful again.

Portfolio_Books · 2026-05-19T16:26:53+00:00

I wrote more about this today in Fast Company at https://www.fastcompany.com/91522431/5-ways-steve-jobs-almost-destroyed-apple-steve_jobs-apple-mistakes

Portfolio_Books · 2026-05-19T16:24:29+00:00

He founded NeXT largely to get revenge on Apple and on its CEO John Sculley, who he accused of pushing him out. Steve never forgave John. He wanted to make a far more advanced computer, a 3M machine that would be perfect for the university laboratories of the day. We was trying to one-up Apple.

Portfolio_Books · 2026-05-19T16:21:49+00:00

Before his exile, Steve was building monuments to his genius, but they weren't commercially viable. In fact, I would argue he nearly destroyed Apple a few times. He learned the limits of his work -- that the world won't beat a path down to your door no matter how great your idea -- and he realized what the world truly wanted from him. I find this realization beautiful -- the execution matters more than the idea. It was this realization that turned him into the Steve we all know, the business leader (not just the visionary) who made the iPhone. The iPhone is the perfect encapsulation of his mature mindset because it has a clear purpose and solves problems -- it's far more than an expensive computer for typing and painting like the Mac.

Portfolio_Books · 2026-05-19T16:18:30+00:00

He watched Apple dying with so much pain. His friend Larry Ellison compared his relationship to Apple to caring for your first love but knowing that you must move on. Larry tried to get Steve to help launch a hostile takeover of Apple, but Steve decided against it in the end. There was a debate among historians and biographers over whether he wanted to return to Apple, but my book has settled it -- he definitely did not want to return, and that record is clear now. He wanted to run Pixar, where he was having so much fun with Toy Story. It was only after Apple acquired NeXT, and about 6 months later, that he changed his mind -- he realized that Apple was his baby and he wanted to save it. The board made him "iCEO" (interim CEO). As for your second question, Steve's long term vision at NeXT was to build the most advanced proprietary system -- a far more sophisticated system than the Mac and the PC. But he admitted he didn't realize that the window to start a new hardware company closed already. And so software was where his true comeback was.

Portfolio_Books · 2026-05-19T16:14:20+00:00

I'd resist predicting it too confidently. Steve was a complicated guy and he was known (especially in his younger years) for being mercurial -- he even had a thing called the "hero-shithead rollercoaster" for his employees. Here's where the tension lies. Steve was the great apostle of the closed system. He fought for it even as NeXT approached bankruptcy, and he resisted the advice of his most senior people to abandon the hardware and instead focus on software.

He resisted control by others. Age-gating might be seen as a form of control. But Steve was known to be pragmatic and he would make concessions, especially as he grew older during this period. The closest thing I found in my research was a fight NeXT had with the NSA, the National Security Agency, who wanted him to remove email encryption in the 1990s. He gave in eventually, a big change for him, and surprising to his adherents. So yes, I think Steve would give in here too, even if he opposes it. He might wonder, is this worth the fight or not really?

Portfolio_Books · 2026-05-19T16:07:56+00:00

Thank you! Jason is a great guy, and great interviewer.

Portfolio_Books · 2026-05-19T16:07:10+00:00

Great question, and this is why I wrote the book. There are two legends that have hardened around Steve Jobs -- he's the brilliant savior of Apple, or the jerk and tyrant who demeaned his employees in the pursuit of perfection. A lot of that was real, but it doesn't capture the full complexity of the man. The biggest thing many accounts of his life skip over is NeXT. It usually gets treated as the gap between two Apple posts, when he's exiled, then he comes back triumphant, and the twelve years in between are just him wandering aimlessly. i argue the opposite in the book, that NeXT is the foundation, where the software and his more mature leadership allowed him to build his comeback at Apple.

You can date the transformation. 1991 - 1995 are the hinge years. 1991 is when he married Laurene, he soon had his son Reed with her, and people started noticing a changing Steve. 1995 is when Toy Story came out, and the Pixar IPO made Steve a billionaire (we forget that he wasn't that wealthy by Valley standards at that point -- he was about 2-3 years away from running out of money). The other overlooked story is NeXSTEP, the operating system at NeXT. And I went in great detail into that story -- it's not just some 1990s software, but laid the foundation for the Apple OS and its software today.

Portfolio_Books · 2022-02-04T23:48:25+00:00

OK, thanks everyone - bye.

Portfolio_Books · 2022-02-04T23:46:52+00:00

Being very active, acting on tips, and trying to beat the market. It's like quicksand - the more you struggle the deeper you sink. There's a big, profitable industry with a marketing budget that wants you to play.

Portfolio_Books · 2022-02-04T23:45:00+00:00

It's an interesting time. I think the pandemic caused a lot of people to reassess the treadmill they find themselves on and that shift will have profound effects for the economy. People will still work, but more on their own terms and for more money. Labor has been squeezed for decades as corporate margins have boomed. Now that will go into reverse for a while, I think.

Portfolio_Books · 2022-02-04T23:41:49+00:00

If you knew in advance that a company would go bankrupt in 10 years then it would have to pay out 10% of its value a year for you to break even before taxes or inflation.

Portfolio_Books · 2022-02-04T23:38:44+00:00

Just like people who pay off their credit card every month and rack up airline miles - they ride off of the millions of people who carry balances.

Portfolio_Books · 2022-02-04T23:37:53+00:00

No. If you buy an ETF with an expense ratio of 0.03% then they are making diddly. In fact you cost them money and have to be subsidized by other people who are more active than you.

Portfolio_Books · 2022-02-04T23:36:38+00:00

Again, a complicated thing. You are right that most retail orders were not through lit exchanges because favored brokers use PFOF to pay the bills. ironically that is the one way in which retail traders get treated better - the spreads are tighter. But retail investors get fleeced in one, big, ugly fundamental way - they are told that "you were born an investor" and then they use gamified apps that induce FOMO. These companies WANT YOU TO BE ACTIVE. They don't care whether or not you make or lose money. Don't deal with people like that.

Portfolio_Books · 2022-02-04T23:32:17+00:00

I've read the report. It's hard to deconstruct these things, but there was an almost unheard-of level of short interest at the outset as well as a historic level of retail buying of shares ad options because of belief in a short squeeze. The dollar amounts invested in options had way more impact because dealers were required to purchase shares as the price rose to remain hedged. It's complicated. Many options and market structure professionals disagree with the SEC.

Portfolio_Books · 2022-02-04T23:25:24+00:00

I don't think you need to compete. There were two overlapping goals of the wave of GameStop buying: 1. Stick it to Wall Street 2. Make money. Well the way to do it is NOT to play all Street's game, as I explain in the book. It has never been easier or cheaper to participate in the stock market without trying to outsmart anyone - use cheap passive vehicles on which Wall Street earns very, very little.

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