It came last week. I’ve been nursing an original 2018 iPad Pro, but that’s like 100 in tech years and it finally stopped working.
I got that first one from Microsoft. Ironic — remember when Apple and Microsoft were the mortalist of enemies? Top Tier Tech Theater. Anyway: it was Apple’s first iPad Pro, their first attempt to make it something more than just a cartoonly large iPhone.
The iPad was the hot device when it first hit the streets; no legit tech exec would be seen in the clubhouse without one. So, we built the shiniest client for it (one that ironically outperformed the Windows client) and it became my globe trotting companion to show customers.
It’s the perfect device for travel; Apple made it fit just so on those fidgety little airplane seat trays. Once I left Microsoft (and airplanes) behind, our forbidden love blossomed. It’s the perfect pick-up for a little writing, a little reading — a little creating. One of my favorite employees1 got me an Apple Pencil for retirement, and I doodled away the hours of Teams calls, counting down to my liberation date.
While I’m sad to see my old iPad (and its stickers!) go, the timing of its demise was serendipitous. Apple had just announced 2026 models with a new AI-optimized chip (M5).
From the press release — so much WOW:
… using third-generation 3-nanometer technology, M5 introduces a next-generation 10-core GPU architecture with a Neural Accelerator in each core, enabling GPU-based AI workloads to run dramatically faster, with over 4x the peak GPU compute performance compared to M4. The GPU also offers enhanced graphics capabilities and third-generation ray tracing …
It goes on like this for 10 pages.
Apple has been hyping AI features for well over a year now, but it’s been mostly bluster. They boldly grabbed headlines re-branding AI as “Apple Intelligence” along with a list of new stuff that sounded fun like custom emojis (genmojis), features for creatives and an overhaul of their voice assistant Siri.
So, I was excited to finally get to play! But after trying for a week, I find Apple AI, well — disappointing.
Turn, Find, Get, Clean, Summarize and Cut … so many action verbs — like I’m that guy on the table in the Operation game.
Image generation is restrictive and while the UX is fun, guardrails make it impossible to create anything interesting. Same goes for custom emojis or genmoji. Word smithing and summarizing — great, but base use case for every AI add-in; table stakes. Photo clean up is nice to have natively but oh so basic. AI image cleanup like removing or replacing the background of a photo isn’t possible. Siri? Still only good for setting timers. Still ‘coming soon.’
One interesting feature is Apples attempt to use AI as the latest way to tease the signal from the noise of everything coming at you by way of notifications/email with AI summaries. This cuts both ways — for example, if you write a newsletter, the chances of your email being seen, let alone read — just dropped dramatically.
Was I wrong to expect more? Apple passed $4 trillion with a capital T last week. It’s not like they don’t have the muscle for real AI wow. Sure it’s hard to add significant new features to an established platform; you don’t want to piss off your base. I love my iPad+7 years of incremental improvements across the board - it’s thin and sexy with a ‘magic’ keyboard that lives up to its name battery life, screen, perf — Apple nailed all of that but it’s not enough.
Apple has always been home for creatives, so are they being super cautious integrating AI because it’s anathema to many? Is their security first stance dumbing down what raw AI can do on other platforms? Will Siri be mind-blowing amazing when they finally ship it?
Remember the “Think Different” ad campaign Apple ran after Steve Jobs returned? Einstein, Gandi, Ali, Picasso. They should watch those spots — they’re risking it all by playing it safe. Ripe for disruption; I love a good tech disruption. Perhaps, for AI to truly remake devices, we need a new device with a new OS.
Maybe they’ll ship that new disruptive device, but Apple hasn’t shipped much new stuff since Steve Jobs died2. When top designer and Jobs work-widower Jony Ive left Apple to “remarry” Sam Altman at OpenAI, expectations ran high for a new device but now they’re being really opaque3 about what they’re doing so I don’t think they’ve figured it out either. Maybe it’ll be some new upstart like friend.com.
We’ll know it when we see it. I felt it when I got that first iPad — that was something special. What’s it gonna be? I know it’s coming.
Sohil, if you’re reading this — yes you are and will always be — my favorite employee EVER!!
Apple Watch and AirPods are the two big things they shipped after Jobs and while both are great, they’re peripherals. Live translation via AirPods is Apple’s most interesting AI feature. The Apple Vision Pro (their VR headset) was DOA when they shipped it just last year.
A Conversation with Sam and Jony from OpenAI’s DevDay is a terribly painful 30 minutes of absolutely nothing being said.


"remember when Apple and Microsoft were the mortalist of enemies?" Oh yeah, biggest memory around that is when Apple were in somewhat dire straits (late 90s), Steve Jobs was presenting at Macworld and Bill Gates came up on the big screen behind him to announce a partnership with Microsoft and a $150 million investment in Apple - and the crowd booed heavily. Apple is way behind on AI. Leveling up Siri is such a very very low bar. I think their best shot at the moment of getting 'back in the game' is if they make a real on-device model (not one that has to go out to the web via ChatGPT for anything not 100% basic) and make it smart enough to take the onus off users to know which app, or set of apps, to use to carry out common tasks - and then less common tasks etc.
I'm still "nursing" a 10+year-old Dell Precision T3600 workstation running WIN10. Her time will come, but the old workhorse is still doing OK for me.