450: ‘Perp Walk for Selfies’, With Jason Snell

Should we just roll with this as the show? I haven’t even peeked at the new Safari and WebKit stuff, other than the usual “purple Safari” build I use.

Safari’s preview gets the future bits, but I’m still stuck recording in Chrome because Safari’s WebRTC gaps knock us back to the bad old “works best in one browser” era, which is maddening.

Same here on my podcast rig, though on my main Mac I’ve been trying Helium, a clean, de‑Googled Chromium with native Kagi and no AI junk—great while it lasts, which indie browsers often don’t.

It takes me back to Camino, the truly Mac-native shell around Mozilla’s engine that proved how hard it is for small teams to keep pace.

Camino wrapped Firefox’s renderer in a real Cocoa app, and Dave Hyatt championed that idea before moving to Apple, which helped shape how Safari separated engine from native app.

That lesson stuck: the web engine should be the same everywhere, but the browser chrome should feel like your platform.

And there goes ten minutes on old browsers instead of baseball.

Speaking of throwbacks, we bumped into each other at WWDC and ended up side‑by‑side for the keynote.

Notebook in hand, old‑school style; we were together again for the post‑keynote tech talk too.

Second row—the first row they’d let us have—so close I could feel the room watching Craig, with Tim Cook and John Ternus right in front of us.

Shortest WWDC keynote in ages, small theater, and the front row was pure executive row, which made arriving early worth it.

I was weirdly nervous for Craig; it felt like high stakes while the current and future CEOs looked on.

Front row to the front row—nice reminder of why you line up early.

I finally shook Tim Cook’s hand on the way out; I usually leave famous folks alone, but he wasn’t going anywhere and it felt like the moment to simply say thanks.

He surely knows Six Colors for its earnings coverage, even if he can’t place the face; I’ve chatted with Ternus a few times and had him on my live show back in the day.

It’s a strange dynamic: we critique them while they read us, so I try not to dwell on it and just serve the audience.

Same here—I detach when I write so I can be fair, even if I know the people involved.

My rule is to hit the work, not the person; you often don’t know who pushed for what, and sometimes the supposed villain was actually fighting the good fight and lost.

That’s why I’ve been sharper about Alan Dye’s design culture than about John Giannandrea, who I think meant well but wasn’t the right fit for Apple’s pivot.

My read, backed by someone who worked with him, is JG’s a research‑first mind hired for bespoke ML, then chatbots exploded and Apple needed a product sprinter—wrong role at the wrong time.

He also came from an AI school that doubted LLMs’ ceiling; LLMs surged, though I think gains are tapering and the future will blend multiple approaches—either way, he wasn’t the leader for that moment.

This year’s message felt like, new team, we’re on it—Mike Rockwell literally said they tore Siri down about a year ago because it couldn’t be saved.

And the evidence points to a real rebuild, which sets the stage for the other big transition: Cook to Ternus.

Tim Cook is the operations maestro Steve needed, a steady hand who grew Apple; John Ternus is a product builder who’s lived Apple’s hardware for decades and feels closer to how we, and Apple’s customers, think.

Tim embodies the talking points and nails the discipline; Ternus reads more like a hands‑on maker who might engage differently.

I wouldn’t be shocked if the media playbook evolves under Ternus once he settles in.

WWDC really felt like the handoff moment and the true debut of Apple Intelligence.

Tim will likely do one last earnings call, then become a front‑row regular like other alumni.

Notably, Ternus wasn’t in the keynote and there was no hardware, but Apple did live demos at the tech talk—including Rockwell’s Siri—so they’re clearly experimenting.

Pre‑recorded keynotes are right for reach and control, but pairing them with in‑person briefings and developer sessions adds the human layer we lost, and it worked.

Being in the room made the Apple Intelligence and Private Cloud Compute architecture click in a way a video can’t; I hope they do more of these.

Let the video be tight and cinematic, then use the live time to teach, demo, and take a few questions—best of both worlds.

This keynote was dialed down theatrics‑wise, and those highly edited videos drive far more views than stage shows, which is why they’re sticking with them.

I loved the early stretch that was boring in the best way—smoothing rough edges—while the big tentpole was Apple Intelligence and a rebuilt Siri.

It had Snow Leopard energy, and even iOS 12 vibes; the Wi‑Fi to cellular limbo finally got smartened up.

They’re now looking at latency and bandwidth, failing over faster, instead of clinging to your dying Wi‑Fi like it’s a lost love.

Apple moves in waves—last year’s design refresh, this year AI plus quality—and a stronger Spotlight index helps both personal context and the assistant.

I still want a culture of continuous maintenance; too many features ship, then sit, and Screen Time’s longstanding issues are the case study.

Don’t run a traveling circus; assign lasting owners for core features so they get cared for year after year.

So, about that, are we out of our minds…?

You and Mike are rolling out Designed in California, an Apple history series funded on Kickstarter, with fifty episodes across a year, and I’m thinking, weekly drops on top of everything else is wild in the best way.

We used Kickstarter to prove there’s an audience for the work and to fund doing it right, with an ad‑free member feed, perks, and art; we record in batches since it’s scripted history, not news, and the early Apple fiftieth episode was our proof of concept inspired by The Rest Is History.

There’s a deep well of sources, some guests who were actually there, and room for arcs like the Apple–Microsoft frenemy saga; I love finding specifics that upend the lore, like the Atlantic City trip with an Apple II prototype in a cigar box and rivals peeking over their seats on the flight.

That conversational history style works—like Acquired or The Rest Is History—great to listen to, not something I’d read as a transcript, and it fits how your 20 Macs project told stories.

Digging into the Apple II showed me the first fully recognizable Steve Jobs: not just Woz’s brilliance, but a consumer finish, a plastic case, and Rod Holt’s power supply—plus the wild anecdote of Woz’s dad trying to push Jobs out, which he didn’t.

Fifty years is a sweet spot: many origin players are still around to talk, while the newer decade remains hard to document and rank, the way older Macs are easier to judge than a recent hit.

Time clarifies the arc; Apple wasn’t special at the start, there were dozens like them, and the reason we tell their story is because of what happened after, not because the early moment looked unique then.

Quick WWDC turn: Apple cut my 2018 eleven‑inch iPad Pro off the new iPadOS, and honestly, it ran so poorly on twenty‑six that I can’t complain, though I wish downgrading were easy.

The first developer beta feels unusually stable, and pro tip—install twenty‑six point six now so the big on‑device index builds in the background before you jump to twenty‑seven.

Indexing took days on my test phone but it stayed usable, and this might be the most solid first beta I’ve used.

Amid the AI talk, it feels like Siri finally got rebuilt in a meaningful way after a decade of lagging.

My mindset is the blocker—I keep forgetting to try Siri AI, then every time I do, it nails the task, which is shocking in a good way.

Personal context is hit‑or‑miss, but the wins are real; I asked for the next two Magnum P.I. episodes we planned, and it surfaced the right Messages thread and just told me.

On the street I asked, what door code did my barber send, and Siri read it back and showed the text; only nit, the voice spoke the digits like a big number instead of a code.

Voices are still rough, sometimes even reading codes wrong, but the Shortcuts leap is the dream—type what you want in plain language and it builds the automation for you, which is the vision Sal Soghoian has talked about forever.

Block‑based Shortcuts used to turn me off; now the natural‑language front end makes the thing, and if I want to tweak steps, the classic view is right there.

Most people won’t build full apps and developers still matter, but LLMs unlock more tinkering for power users; I set up do not disturb when my shower speaker connects by just stating it, and while third‑party actions aren’t wired up yet, you can see where this goes.

Apple didn’t ship a full Xcode vibe‑coding flow, but tools like Cursor and Claude can already drive it, which makes me wish Apple would make a GarageBand‑for‑apps front end.

Playgrounds isn’t that; a true GarageBand‑style tool would help, but Shortcuts’ natural‑language step feels like the right first move because far more people will use it.

This is finally the Shortcuts I wanted—I can say, send me a 5 a.m. weekday email with these sources, then change it with a sentence the next day.

Apple had to fix long‑standing gaps like if‑else and tying automations to a specific shortcut to make the new interface work, and everyone benefits from those upgrades.

Siri AI rides on a better Spotlight and Mail search, and semantic intent beats the old one‑word box—Siri can find the right note about my grill in a haystack where Notes’ search can’t.

LLMs understand what you mean instead of doing brittle string matches, so I can ask for a red wagon and still find a note that says trailer; I expect more search fields to become smart prompts.

I’m close to putting iOS twenty‑seven on my main phone, and macOS Golden Gate is a sweep of small wins—cleaner menu bar menus, corner radii finally consistent—and I might skip Tahoe and go straight to the beta.

Let’s just say it feels like a real shift in design philosophy, and yes, I hoard domains and redirects, including sixcolow dot rs from the old link‑shortener era.

Upgrade remains your weekly show with Mike; anything else to plug?

I’m grateful we got to share the new show here, and now that WWDC and my son’s graduation are wrapped, I can finally sit down and start making it.