2026-05-21 06:30:20
I recently got to read an advance copy of Geoffrey Cain’s new book, “Steve Jobs In Exile: The Untold Story of NeXT and the Remaking of an American Visionary,” which was published this week. 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.)
Contrary to popular opinion, Jobs did not get fired from Apple—he got parked in a useless role until he quit out of frustration, as Cain recounts. Jobs was motivated to start NeXT Computer for two reasons: He saw a potential market for a high-end workstation in education and industry, and he knew that this was a market Apple wasn’t especially interested in, so he could avoid expensive and distracting lawsuits with the company he was being pushed out of. (That didn’t work.)
As depicted in the book, the same cycle seems to repeat again and again. Out of the gate, Jobs decides what his new company will focus on by cannily identifying a potential market—the demand for “3M” machines, workstations with a megabyte of memory, a million-pixel display, and a processor capable of handling a million instructions per second. Scientists and researchers, Cain recounts, said they would buy them in large numbers—assuming they cost no more than about $10,000 each.
Then the second cycle happens: Jobs ends up getting focused on all sorts of little details that matter to him, but don’t necessarily serve the original product goal, from the design of the factory that would build the workstations to the expensive physical design of the workstations themselves, made unlike any other computer in existence.
The end result was pretty much what you’d expect: 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.
Time and again in “Steve Jobs in Exile,” you see Jobs act like his company’s own worst enemy. He makes decisions for perfectly understandable personal reasons, but they go against the entire premise of the company he had established. (How does a guy with a fundamentally anti-establishment worldview end up building a company designed for elite institutions, industry, and the government?) The situation at NeXT becomes increasingly untenable, and to Jobs’s credit, he does seem to have learned that his mistakes are what led the company to the cliff.
When Jobs discovered that a small piece of the overall NeXT software picture, WebObjects, had a potential market in revolutionizing early web commerce, he recognized it, and the company benefited. But you get the sense that Jobs was not comfortable changing the world of selling things on the Internet, when he really still wanted to change the world.
In the end, NeXT’s investment in a forward-looking Unix-based operating system underpinned by the Mach microkernel made it an acquisition target for Apple, which was desperately looking for a replacement for the classic Mac OS. The rest is history, though Cain points out just how dramatic and fraught the merger of the NeXT staff with Apple’s late-90s engineers really was.
If you think Jobs’s years at NeXT were some sort of graduate education in which he grew older and wiser so he could emerge, fully formed, as Apple CEO, you’ve got it wrong. As Cain expertly points out, the NeXT era was one in which Jobs was humbled again and again, until he started to realize that his instincts were not infallible, his distortion field did not reflect reality, and that he had to modify his behavior to have any hope of success. (In fact, Jobs’s greatest success during the period came with Pixar—where he had a much more hands-off relationship with the company’s executives.)
The Jobs who sold his company to Apple was not tanned, rested, and ready for action. He was beaten, battered, bruised, and humbled. But he had learned enough lessons that he was able to give Apple a better version of himself, the second time around.
[Steve Jobs In Exile (Portfolio), available at Amazon, Bookshop, and everywhere else.]
2026-05-21 02:25:53
The apps we given up on, how often we go to the Apple Store, the first things we do on our phones every day, and our latest tech joys.
2026-05-20 22:00:00
Dan shops for URLs, Lex makes a video and Moltz runes everything.
2026-05-20 13:01:55
Apple Sports got its World Cup update on Tuesday:
Apple Sports — the free app for iPhone that gives fans access to real-time scores, stats, and more — is now available to download on the App Store in more than 170 countries and regions around the world, including more than 90 newly added markets. Designed for speed and simplicity, the app delivers a personalized experience, putting fans’ favorite teams and leagues front and center with a simple, intuitive interface designed by Apple.
In addition to being available in 90 more regions, there are a bunch of nice soccer features, including a starting line-up, all geared toward this summer’s World Cup, which is less than a month away.
2026-05-20 05:10:00
Joe Kissell, the fellow behind Take Control Books, has a new, live course: Taming Big Tech. As a multi-decade writer and teacher, and someone deeply skeptical about the invasive power of the biggest technology firms in our life, Joe is aptly placed to offer rich, practical insight. The four roughly 90-minute sessions include time for questions from participants. The course starts May 23, 2026, and then takes place every two weeks through July 11. All sessions are recorded in case you miss one, or for later playback.
Joe’s covering a lot in this course, but you can distill it down to a few principles: how to ensure your private information remains under your control, what you can do (if you want) to migrate from Big Tech products and services to alternatives, and how to minimize or eliminate privacy risks. The course includes a discussion forum, downloadable PDFs, and optional homework and quizzes, which can be a useful way to ensure your understanding of material. I trust Joe’s insights and his teaching approach, not only because (disclosure) I’m the Executive Editor of Take Control Books, but because I’ve seen over that time how patient he is at explaining the frustrating things tech companies (including Apple) do to us, instead of for us.
2026-05-19 20:00:00
In a series of announcements that just might signal a wider focus on AI at the upcoming WWDC, on Tuesday Apple previewed upcoming accessibility features in the run-up to this week’s Global Accessibility Awareness Day.
VoiceOver and Magnifier will gain AI-powered features that can provide enhanced image description, using the device camera. VoiceOver’s Image Explorer will use Apple Intelligence to give more detailed descriptions of what’s in photographs, scanned documents and labels, for example.
With updates to live recognition, VoiceOver users can press the iPhone action button to quickly ask a question about what’s in the camera viewfinder and get a detailed response. Users can also ask follow-up questions in their own words to get more visual information. These question features resemble what’s available to users of the Be My Eyes app’s Be My AI feature, but it’s unclear whether Apple’s offerings will go further.
Magnifier for iOS and Mac will include the same Apple Intelligence-powered options, which can be used with speech or high-contrast onscreen text. Magnifier users will also be able to speak to the app, to get more specific information about their surroundings, or to ask follow-up questions.
Voice Control is set to get an Apple Intelligence boost, giving users the ability to describe an element onscreen they want to act on, instead of using a numbered grid, or remembering an item’s label. The natural language support should also allow Voice Control users to navigate apps or elements that aren’t labeled for the feature.
Accessibility Reader, which renders onscreen text in ways that are visually more accessible, including larger fonts, high-contrast backgrounds, and clutter-free layouts, will provide AI-generated summaries on demand, and can translate text into the user’s chosen language.
AI-generated captions will be available alongside standard SDH and closed captions, and also in places where no captions are provided otherwise. They’ll be available on macOS, iOS, Apple TV and Vision Pro, and they can be styled to meet the viewer’s taste or needs.
Power wheelchair users looking for a reason to try Vision Pro might find one in this year’s accessibility announcements, especially if they use an alternative drive controls to steer the chair. Those who can’t use a standard joystick to navigate often employ sip-n-puff switches, head arrays or other devices. With this year’s updates, Vision Pro users will be able to use eye-tracking to control compatible alternative drive systems. At launch, Vision Pro will be compatible with TOLT and LUCI systems.
Other updates coming this year include motion cues for VisionOS, improved Apple device handoff for Made for iPhone hearing aids, larger text support in the tvOS interface and more.
Today’s preview marked the fifth straight year Apple has used GAAD week to preview accessibility features coming to its platforms in the fall. GAAD celebrates its fifteenth year.
