443: ‘The Pogue Feature’, With David Pogue

Hey, it’s your internet pal John Gruber. David Pogue’s here fresh off a plane on a whirlwind tour for his new book, Apple: The First 50 Years, so this one’s tighter than usual but perfectly timed.

I’ve dipped through the book and can recommend it on the intro alone; it’s a hefty, gorgeous, full‑color tome that reads like an Apple encyclopedia.

I fought to keep the whole book in color and leaned into the products, prototypes, and behind‑the‑scenes tech instead of boardroom drama. You’ll see one‑offs and never‑shipped ideas alongside the hits.

You had the standing to cover the Tim Cook years without Apple steering the wheel; how did that access work without editorial control?

The early years were easy to source, but the recent decade was tough until Apple agreed to extensive interviews with the executive team, engineers, and designers, plus archival access. The archivists surfaced hundreds of images no one had seen.

For a company wired to look forward and keep quiet, it’s wild they’ve kept such a deep archive; that tension’s part of Apple’s DNA.

Tim told me honoring the past is a ‘new muscle,’ and inside Apple the pace is so intense there’s barely time to toast a launch before the next one starts. Rubinstein pushed the annual iPod cadence after spotting Toshiba’s tiny hard drive, while Sony fumbled with a music player that would not even play MP3s.

That self‑imposed urgency—almost paranoia—kept Apple sharp even when rivals were asleep, like moving iTunes to Windows so the iPod could scale.

Jobs killed the iPod mini at its peak to bet on the thinner nano, and he was right about that taste call. He was wrong about music ownership though, since subscriptions won.

Owning shelves of CDs made sense to us, but for our kids streaming is the default, with a little retro CD and iPod nostalgia sneaking back in thanks to school phone bans.

We’re losing first‑person voices; I interviewed more than 150 people, and a few have since passed or can no longer speak, which made capturing their accounts feel urgent.

That’s why fifty matters now, and why Chris Espinosa—who joined at fourteen and never left—is a treasure for detail and continuity.

He even untangled the Apple III heat fiasco, where a no‑fan design cooked the internals and the field fix was literally to lift and drop the machine to reseat boards—unthinkable for Apple today.

What sparked the project, and did you worry a flood of ‘Apple at fifty’ books would land at once while you tried to satisfy fans, skeptics, insiders, and casual readers?

After a packed CHM event, my wife said, do the fifty‑year book, and I sprinted; shockingly, it’s the only one. The real stress was threading the needle for all those audiences while correcting old myths.

You’ve also influenced the story: the iPhone’s screenshot shortcut traces back to you needing images for your book, and you wrote the Conflict Catcher manual before Jeff Robbin went on to iTunes.

Apple first refused me any screenshot tool, then assigned an engineer for months, then finally added the two‑button screenshot because no one wanted to repeat that; internally they nicknamed it after me. Years earlier, Jeff and I built a rehearsal MIDI app, a stepping stone on his path to music software.

Sculley gets dinged for Newton, but under him came RISC Macs, PowerBook, QuickTime, and even the eerily accurate Knowledge Navigator concept; Newton’s real miss was the lack of always‑on networking.

The first iPhone underwhelmed without third‑party apps, and Jobs initially wanted Apple to write every single one; Forstall quietly built the App Store foundation anyway, and opening it lit the fuse for whole industries.

The iPhone became the true ‘computer for the rest of us,’ even as its downsides worry people at Apple; the likely next act is ambient computing—voice‑first, screen‑sometimes—like Her or a single AI across devices.

Meanwhile Apple has quietly become a health company, with FDA‑cleared AFib alerts, fall detection, gait and sleep insights, and sensors creeping into AirPods; even Apple’s pro display now meets medical standards.

That medical push is real business, and the pricing flips the market for clinical displays; which never‑shipped Apple project sticks with you most?

The car: a lavish self‑driving lounge on wheels that reset from a shippable version to chasing full autonomy, and the goalpost kept moving until Cook shut it down.

Jobs might have forced a version one into the world while Cook was willing to cut losses; we cannot know, but their instincts diverged there.

He left at the peak of his creative powers, which makes the what‑if both tempting and impossible.

Before we go, the cover is perfect—clean yet loaded with meaning—how did you choose it?

I designed the iPod click wheel for its iconic simplicity, and the double arrows double as a timeline—looking back and looking forward—which is the whole book in one image.

It lands exactly that way; thanks for racing in between events, and everyone should pick up Apple: The First 50 Years.

Thank you, and I’m also writing again on Substack after a long break.