437: ‘A Naughty Citizen’, With Quinn Nelson

Quinn, you’ve had a year—new dad, January baby, first Christmas, and that wild Iron Man phase where three things happen at once and you’re just hanging on.

We’re almost at one year, she’s crawling like crazy, and we went from one baby gate to a full red‑alert lockdown in about two weeks; I already miss the sleepy little lump days.

Two big topics today: iPadOS 26’s new windowing and Apple’s executive moves—let’s hit iPad first before it turns into the famous two‑hour quick chat.

I went iPad‑first this year because the M4 iPad Pro hardware is irresistible, so I started with email—Spark is great on iPad—and kept using it for more, while still grabbing the Mac when I needed to.

iPadOS 26 changes how I use the iPad, but it’s not a Mac; core design choices make them different, and until Files gets more Finder‑like and there’s a way to run Mac apps in iPad windows, that gap stays.

Apple’s in a uniquely Apple bind—two platforms that overlap—while the iPad Pro might be their nicest hardware but still ships without swap, which is where the pain shows up.

Pros hit walls because iPadOS can’t load certain formats or extensions the Mac takes for granted, and apps like DaVinci Resolve reveal how close the binaries can be while the OS still says no.

A lot of big‑name apps use their own frameworks, which made porting feasible, but they can clash with Apple’s UI norms; Apple loves to showcase polish, and Resolve’s early menu‑bar‑in‑window vibes weren’t that.

Resolve’s gotten more Apple‑friendly, but the larger truth stands: iPad keeps getting stronger while some pro jobs still demand a Mac, and that contrast amplifies frustration.

I ran the same local LLM on an M‑class Mac and iPad with the same memory—on the Mac it slogged along with swap and beachballs, while iPadOS just refused and killed the party.

I even watched iPadOS kill Photoshop in the foreground because Resolve’s export grabbed memory entitlement, and that would never happen on the Mac where the system shuffles, slows, but survives.

It’s two philosophies: iPad stays snappy by evicting, the Mac stays faithful by grinding; the deeper issue is iPad’s big‑iPhone roots, and if Apple only made iPad and Mac, iPad would be more computery by now.

How’s the new windowing feel day‑to‑day?

The learning curve is steep because touch and trackpad fight for the same space, the traffic‑light buttons look Mac‑ish but act differently, and minimize semantics and snap behavior can confuse.

Menu‑bar discoverability is uneven, multi‑window support is spotty, and stage manager pulls apps between stages in ways that feel unpredictable, which is what happens after years of shifting modalities.

Even Apple’s own apps diverge: Mail can spawn multiple full viewer windows on the Mac while Notes stays single, and that multi‑window thinking rarely makes it to iPad apps.

On the exec front, Alan Dye leaving stung given his WWDC spotlight, and the Srouji scare fizzled when he sent the classic I’m‑not‑going‑anywhere note.

Mac openness means I can supercharge Notes with third‑party helpers, but none of that is possible on iPad, so I’ve made peace with a two‑thousand‑dollar iPad still needing a seven‑hundred‑dollar MacBook Air sometimes.

I hope 26 is the breakthrough where Apple finally accepted windows; stage manager’s legacy still muddies things, but new design leadership could unify the story.

Meanwhile, Jeff Williams retired, Lisa Jackson and Kate Adams moved on, and John Giannandrea started his long goodbye after Siri stagnation and the Apple Intelligence delay.

It looks like Apple may white‑label Gemini to catch up, and Cook handled JG’s exit in a low‑drama way, but the moment Apple pushed the delay, his fate felt sealed.

JG’s a world‑class researcher, but organizationally it didn’t click; Federighi’s team went hands‑on with LLMs, parallel tracks formed, and reported GPU shortages didn’t help a plan aimed too hard at on‑device.

LLM skepticism met reality once Craig tried chatbots, and while Apple doesn’t need its own chatbot, it has to integrate the tech; Mike Rockwell now steering AI under Craig signals a reset, and he feels very Apple‑like.

Vision Pro’s problem is price and heft, not software; VisionOS is remarkably polished, which reflects well on Rockwell’s org.

Vision Pro echoes the original Mac—too heavy and pricey at first, but the foundation is right—and Rockwell seems hungry to fix Siri‑class problems with results, not slideware.

On Alan Dye, I suspect VisionOS interaction came out of Rockwell’s group with Dye’s team focused on visuals, and liquid glass feels more like a self‑inflicted knockoff of VisionOS than its source.

VisionOS looks distinct, while liquid glass didn’t drop cleanly onto iPhone and Mac; the transparency often hurts readability, and Apple adding a visible dial‑back in 26.1 says even they weren’t sure.

Slide Over’s return and a tinted option landed late, which matches what testers begged for all summer; liquid glass looks best on iPhone, tvOS is lovely, and the Mac still looks off.

I leave liquid glass on my iPhone, but on the Mac it’s rough; when I booted a Sequoia machine, it looked fantastic.

Same here: downstairs I’m on Tahoe, upstairs my main Mac’s on Sequoia, and every time I switch I’m struck by how fragile the Mac UI feels, like bits are stuck on with tape and could peel off. Liquid glass helps a little and buttons finally look like buttons, but it’s nowhere near as coherent or cool as Vision OS, which tells me Dye’s team wasn’t really driving this.

Part of why Vision OS and iOS read better is HDR everywhere; on the Mac, Safari’s UI can vanish into near‑white backgrounds, and you literally can’t see controls unless you’re on a super bright MacBook Pro. We’re months into 26.2 and basic legibility is still broken, which makes me wonder why it shipped in this state.

Inside Apple, Dye’s exit landed like a celebration; people I heard from were thrilled, and Stephen Lemay was the pick they’d been hoping for. The gripe wasn’t just taste, it was politics—Dye and lieutenants like Billy Sorrentino excelled at managing up while the craft slipped for the people doing the work.

Two things can be true: Apple still has the best UI in the industry, and it’s also fallen into avoidable fundamentals that used to be flawless. That disconnect let Dye skate, because from the top, a quick day on Android makes Apple look fine, even when the basics aren’t.

Liquid glass isn’t going anywhere; it’ll mature the way iOS 7 slowly did, from pretty slides to something you can actually read and use. You still need a leader who connects all the modalities, and it’s worrying that Dye played the system long enough to keep everyone convinced.

At Apple’s level, no one horse‑trades with offers—people are there because they love the work, not to squeeze Meta for a raise. My read is Dye got a mountain of money and a shiny title, took it, and oddly enough that’s the best break Apple’s had in a while.

Yeah, it feels like a trade where both sides might actually come out better.

On Lisa Jackson: she’s delightful and I buy that Apple’s environmental push is mostly real, with some inevitable PR gloss. It’s curious her role was dispersed instead of refilled, but the optimistic view is the program’s now baked into the org.

If Apple 2030 is only four years away, most systems should be in place, and Ops can drive it the rest of the way.

AI muddies carbon math—what’s Apple’s footprint versus a partner’s—but we’ll see how they count it.

On succession: Arthur Levinson ages out this February, so I expect Cook to become chairman while staying CEO, then outline his exit path. My bet is 2026 is when the handoff starts.

That dual role isn’t unusual—look at Microsoft—and it doesn’t have to mean he’s halfway out the door right away.

He could signal timing next year or the year after, and they might not name the successor immediately.

Succession is hard—see Disney’s Iger‑Chapek saga or Amazon’s careful baton pass—yet Apple and Cook seem to be orchestrating this calmly. The goal is no drama, no hit to the stock, just a clean glide path.

Turnover is normal after a CEO change and Apple’s tenures are already longer than average, so some exits are just the cycle. I don’t expect Federighi to bolt; he seems fulfilled and not chasing the corner office.

Craig truly loves software and might see running all of software as the right ceiling, not a stepping stone—Peter Principle avoided. If it’s John Ternus, we’ll want to see that his interests span more than hardware, but he may well be the fit.

A lot of Apple leaders are mission‑first; if the new CEO lets them do their best work, declining the top job isn’t a slight, it’s alignment.

These folks also have real personal ties—Craig fixing Eddie’s iMac says a lot—and Cook can quietly time retirements to avoid a post‑handoff panic. Better a few exits now than a rush that gets framed as turmoil under a new CEO.

A Yale study pegs average post‑handoff C‑suite turnover around thirty percent, and Apple’s exceptional stability makes planning even more important. Like him or not, Cook’s track record speaks for itself.

If Eddie Q and Joz stay through the transition, that signals they’re in for a few more years; if not, they’ll likely bow out beforehand. I could see Cook taking the chair early in the year and the CEO handoff landing late in 2026, which fits the natural year‑end cadence.

That gives the successor time to be visible and integrated, without lingering so long that control gets muddled.

Watch WWDC: if Ternus shows up prominently in what’s usually Craig’s show, that’s Apple hinting without saying a word.

One more to watch is Deirdre O’Brien—she may announce a runway, or commit for a longer stretch.

She’s run People and Retail with quiet competence after the Angela Ahrendts era; no news about the stores is good news. She even feels like the kind of steady hand you’d tap as an interim if disaster struck, and if she isn’t leaving soon, it’s because she’s exactly where she wants to be.

Always great chatting—enjoy the rest of the holidays, and you can find the show notes and his channel by just searching for snazzy.

I might finally own that word—if I’m not first, I’m at least near the top.

On Google, you’re right after the dictionary entries, which isn’t bad; Snazzy Labs pops right up on YouTube. Honestly, you probably rank better for snazzy than I do for daring.

No.

You don’t even need the labs—snazzy carries it; I need both daring and fireball together.

Good talk, and thanks to everyone who stuck with us to the end.