Good Wearable AI Gadgets Are Already Here, And You Might Already Own One
We’ve all been waiting for the first good AI wearables to come along. There have been tons of attempts, from wrist-worn recording devices to pins with lasers to glasses with cameras. Company’s are throwing everything at the wall to see what might stick. Some of these gadgets have been pretty decent, namely Meta’s Ray Ban collaboration. The idea is sound but the AI has been mediocre. As cameras, they’re wonderful but as an AI gadget they’re mid at best. Perhaps that’s why Mark Zuckerberg has been on a rampant AI hiring spree. While that was happening though, Google dropped something that might just shake up the game. Gemini has finally arrived on Wear OS watches like the Pixel Watch and Galaxy Watch. And guess what? It’s really freaking good.
18 Years Ago Today, iPhone Premiered and Everything Changed
On this day, 18 years ago, the iPhone went on sale for the very first time at Apple and AT&T Stores across the United States. I was going to write a long piece reminiscing about that special day, but I remembered that I already did that a few years ago when I was at 9to5mac for the 14th anniversary. I highly recommend returning to that piece to relive launch day and though you may have issues with images showing up, the text is still great too if I do say so myself.
Meta Goes on an AI Hiring Spree, What's Apple's Plan?
Apple should be the one on a hiring spree. Over the past few weeks, Mark Zuckerberg and Meta have kicked the hiring and acquisitions machine into high gear. The man knows he can’t miss out on the next platform shift and it shows. It wasn’t the metaverse and it wasn’t goggles, but it’s almost certainly some form of personalized super intelligence.
F1 Marks Apple's Acceleration into a New Era of Entertainment
Apple’s had a very good run with its string of successful streaming shows on TV+ over the past six years and has frequently been called “the new HBO." But the company has struggled to land a true hit with its feature films that it bestowed theatrical releases on. Sure, they’ve won Oscars for CODA and movies like Killers of the Flower Moon were well-received. But none of them have been able to capture the scale of a massive cultural moment. I have good news, I think F1 is finally that film.
The Curious Case of Apple and Perplexity: Do They Need Each Other?
Apparently it’s the season of acquisitions and hirings. Thankfully, this time Apple is also in on the action. According to Mark Gurman, Apple executives are in the early stages of mulling an acquisition of Perplexity. My initial reaction was “that wouldn’t work.” But I’ve taken some time to think through what it could look like if it were to come to fruition. Let me share where my head’s at.
On Dia, Arc, and "People Don't Know What They Want Until You Show it to Them"
I was absolutely captivated by the Arc web browser from the moment I started using it a few years ago and quickly became an evangelist. It really felt like an entirely new idea for how to use the internet, it was more organized while also somehow being more fun. It became an essential part of my workflow on the Mac and when it first came to iPhone, it became a cross platform obsession. The introduction of Arc Search and Arc Max signaled however, that The Browser Company was thinking bigger. With the advent of AI tools around the same time as Arc was taking off, it was becoming clearer and clearer that the internet was about to change dramatically. Arc continued to improve between 2022 and 2024, but at the end of the year they decided to pivot. Instead of building on Arc, they chose to build an entirely new browser. I suppose apt for a company literally called “The Browser Company."
“The Talk Show Live” Returns to Form—And It Was Great
While there was a lot of consternation heading into WWDC over Apple skipping John Gruber’s live taping of The Talk Show, it might have all been for the best. Instead of sitting down with Craig and Joz, who were both unlikely to say much more than they did during the day, we got to hear a really fun conversation between John and two of my favorite people on the internet: Nilay Patel and Joanna Stern.
Apple Snuck an Endorsement for Ivory and Mastodon into WWDC
One of my favorite moments from WWDC 2025 was when Apple designer Billy Sorrentino introduced the changes to visual intelligence. The new screenshot features in iOS 26 are already among my favorites, but what really caught my eye was the surprising amount of screen time given to Tapbots’ Ivory.
WWDC 2025: Through Liquid Glass—No Longer Behind, Just Off to the Side
I was unusually concerned heading into this year’s WWDC, fully prepared to be disappointed. I feared that Apple would continue to be on weak footing after the Apple Intelligence failures of the past year. To my surprise, I feel very differently post-keynote. I worried that they wouldn’t acknowledge what happened last year, but Craig addressed it right out of the gate. While the acknowledgement itself is appreciated, we still have to wait quite a long time for the new Siri to rear its face… or voice, I guess? Fortunately, Apple did deliver a combination of new AI features that are sprinkled throughout their new operating systems. I am largely relieved, albeit still slightly on edge for reasons we’ll get into later. Over the course of the keynote, I began to relax as they subtly and intentionally introduced an array of practical AI use cases one by one. I am actually quite excited about some of these, but none of them compare to the triumph that is Apple’s new universal design language: liquid glass.
Apple’s Silence at "The Talk Show" Will Speak Volumes
If you follow Apple at all, you’ve likely heard the news: Apple’s skipping John Gruber’s The Talk Show Live at WWDC this year. For a decade, it’s been tradition for Apple executives to join John on stage at the annual conference to recap the the keynote and dive deeper into the announcements. It is one of my favorite parts of that week, something I look forward to every year.
A Tale of Two IOs: What it Looks Like When Apple Doesn't Lead
We are at more than just an inflection point; we’re at a moment where the global technological order may be about to fundamentally change. Don’t think about this just as an “iPhone moment” but as an “Apple acquires NeXT” event. A NeXTus event if you will. When Apple acquired NeXT, it kicked off a series of technological shifts that were completely unforeseen. It led to products like iMac, iPod, iPhone, iPad, and Apple Watch and technologies like Cocoa, Cocoa Touch, AirPort, Apple Silicon, among countless others. That acquisition fundamentally altered the course of human history and changed the technological landscape. I believe that the events of last week may have done the same.
Is Memory Going to Become the New iMessage Lock-in?
Raycast for iPhone is the Launch Center Successor I've Always Wanted
Before it was sort of abandoned I was a heavy user of Launch Center Pro. Apple enthusiasts and power users alike will almost certainly remember the powerful shortcut tool from Contrast that let you build out an extensive grid of quick ways to get things done. The app is technically still available on the App Store, but it has not been updated in years. I stopped using it once it appeared to fall by the wayside and after Apple began truly supercharging its own solution in Shortcuts. Launch Center Pro was very much a manually configurable tool, but had it kept up with the times I would imagine it would look something like the new Raycast for iOS. Funny enough, Raycast for iOS almost resembles the original version of Launch Center from 2011. We have sort of come full circle.
With Google's Defeat, the Time for Apple's Search Engine Has Arrived
Unless you’ve been living under a rock, you know that Google was formally ruled an advertising monopoly this week. It could potentially be a catastrophic blow to the company that completely upends the web as we know it. A significant component of this case has been Google’s deal with Apple to be the default search engine in Safari. Google pays the Cupertino company nearly $20B a year to maintain dominance on Apple platforms. That is for good reason of course, Apple’s users are some of the most valuable particularly when it comes to ad targeting. But it is also a flagrant way to squash any chance a competitor could have at growing to be a sustainable web search or ad business. Now that the verdict is in officially, I think it is time for Apple to do what has been long rumored. That is, to build their own search engine that powers Safari, Siri, and Spotlight.
Jony Ive, Laurene Powell Jobs, and Sam Altman Walk into a Bar—Will They Walk Out with the Gadget of the Future?
The worst kept secret in Silicon Valley right now is that Jony Ive is helping Sam Altman build new gadgets. On the surface that may not seem like that much of a big deal. After all, Jony left Apple six years ago. But his career is inextricably linked to and was fundamentally shaped by Steve Jobs and Apple. I do not say that to diminish him in any way, it is simply the truth that he would not be “Sir Jony Ive” without the iMac, the iPod, the iPhone, the iPad, and the Apple Watch. For years he has seemingly tried to separate himself from his historical identity by working on a variety of different projects removed from technology, but he will forever be associated with those products whether he likes it or not. When he spends time on a technology, it carries a lot of weight. He learned from the best. As an example, his signature has been all over Airbnb’s app and branding—the company has been a major client of his firm LoveFrom. It is just one of the things that makes his teaming up with Sam Altman all that much more intriguing.
At first the rumors were relatively vague. The two of them were thinking about building some kind of AI-powered gadget together, whatever it may be. It has since become clear that the two intend to build a personal AI device, likely one that rethinks the role of the smartphone or even begins to replace some core functions. It is not all that surprising that they have fallen back on what could be a handheld device given the flat reaction to dedicated AI gadgets over the past two years, perhaps with the exception of the Meta Ray Bans. I personally think that lots of tech aficionados have sort of written Jony off in his post-Apple years. That has made it easier for him to explore whatever the project ultimately becomes. But it is unmistakable that the man who designed the iPhone, built his entire fortune on it, and shares the credit of creating it with his late best friend, believes that building competitive hardware is worth his time in 2025. That tells me that he not only believes in both Sam Altman and the power of AI, but also that he does not believe Apple is currently well-positioned to do something similar. The saga of Apple Intelligence blunders thus far may just help back that up. So Sam Altman and Jony Ive are working together to create the device of the future, what could that mean?
Many of the rumors seem to equate this product with some of those failed AI gadgets I mentioned. Some pundits think it could be screen-less or have an unusual twist that makes it less of an iPhone competitor and more of a new product category. I think they are all overthinking it. Whatever these two prolific giants of industry are working on is not the Humane AI Pin or the Rabbit R1. It cannot be a vanity project. OpenAI has been spitting out incredible new products at a ridiculously fast pace over the past several months and I do not see Sam Altman wasting anyone’s time. The fact that he wants to pull the project into OpenAI says as much. That suggests it might end up being close to a new kind of phone—perhaps familiar in shape, but powered by something so fundamentally different. When I hear “personal AI device” I hear “we want to replace your phone.” The way to do that, especially if you are a designer, is to make something relatively familiar.
Despite what many AI skeptics have believed, it seems to be bearing out that the chatbot is the interface of the future. At least the near future. A grid of app icons on a home screen could quickly be usurped by a text thread with a digital being that lives in your phone and can use your services for you. We are already heading in that direction. Just this week, Anthropic added connectors for Gmail and Google Calendar making Claude infinitely more personal and useful. OpenAI continues to expand its integrations with apps like Xcode and Notion, making it easier than ever to simply code an entirely new app or write an entire story on a fly with a short prompt. Gemini can access nearly every major Google service already. Microsoft Copilot can see what is on your screen and talk with you about it. Apple was hoping to be able to accomplish these things through a combination of an improved Siri, on-device models, and app intents. But I am not particularly optimistic it is going to all work as well as it needs to. App intents are built on Shortcuts which is already a fragile house of cards. I think they need to start over from scratch, but they are already so far behind that it is unclear if they can risk it. Especially as competitors take giant leaps seemingly on an almost weekly basis, heck, OpenAI just dropped two brand new models today in o3 and o4-mini.
A phone or phone-shaped device with hardware and software designed by Jony Ive and his team at LoveFrom (many of which are former Apple designers, including Evans Hankey) combined with the intelligence of OpenAI could be the first truly formidable opponent the iPhone has had to go up against since Samsung first unveiled the Galaxy series. ChatGPT is an incredibly popular product with hundreds of millions of users. And not because they have to use it, but because they want to use it. It has very strong brand recognition and has become an essential part of peoples’ daily lives. It certainly has for me and many in my orbit. And it is especially the case with younger users, the trend setters who will determine which company owns the future. My generation decided that iMessage and the iPhone were the best. The next might choose otherwise. While it is still incredibly early to say for sure what the device ultimately will be, I imagine a new generation of smartphone, for lack of a better word, that eschews apps for connectors. A device that starts with a text box and an always-listening voice mode that uses your apps and services for you, that does not take you out of context or distract you periodically through the day. The OpenAI device could actually be the antidote to much of the societal damage the current generation of smartphones has done. While I would never use a current Android phone as my daily driver, I would absolutely consider using a Jony Ive-designed OpenAI device in lieu of my iPhone. Especially if it made me more present and productive.
Apple should be worried. They are more vulnerable than they have been in decades and it shows. If Jony Ive, a Steve Jobs acolyte and one of the most prolific designers of our age sees an opening to dethrone Apple and right societal wrongs, he seems likely to take it. And this is not like Jon Rubenstein going to Palm to build the Prē, this is different. There is no Steve to single-handedly steer the ship into the future or to crush competitors with breakneck speed. There was also no new technology nearly as important as a tool like ChatGPT to differentiate other devices. Things get even more interesting when you consider that Emerson Collective is one of the project’s backers. Emerson Collective is none other than Laurene Powell Jobs’ firm. That means Apple could be going up against a new kind of product from the hottest tech company since Google, with the backing of the iPhone’s principal designer, Steve Jobs’ incredibly savvy wife, and the figurehead for the AI revolution. If Apple is incapable of getting their house in order with Intelligence, then a personal OpenAI gadget that begins to take the place of the phone, could truly begin to put deeper and deeper cracks in Apple’s glass house. If this new device succeeds, whenever we may see it, it will not just challenge Apple’s grip on personal hardware—it could redefine what that hardware is and how we use it.
Apple Will Try to Fix the iPad a Fifth Time, Will it Work?
Apple has tried to fix the iPad four times. First in 2015 with the introducing of Split View, picture-in-picture, and better accessory support for keyboards and the Pencil. Then they immediately took a year off. iOS 10 on the iPad sort of phoned it in. It became abundantly clear that they either could not or would not update the iPad as aggressively as it needed. The following year, iOS 11 brought the second wave of major changes with the advanced dock, drag and drop, the Files app, and more adjustable slide over. This was a big year and it showed that there was a clear willingness inside of Cupertino to push the iPad harder. But then again, another year off with iOS 12. Then the third major fix year arrived with the introduction of “iPadOS” as a dedicated platform for the first time. It brought multi-window support to apps, way better slide over support, new gestures, and plenty of other goodies like Home Screen widgets. As you might guess, iPadOS 14 felt like another year off despite a handful of smaller tweaks. iPadOS 15 did not go big though, despite what Apple wanted us to think. It brought new multitasking controls to make everything a bit more obvious to users, but it did not fundamentally change the way things worked. Then iPadOS 16 arrived and sort of blew everything up. Stage manager alone was a massive addition, providing adjustable window sizing and external display support. A common theme however among these updates is that while they were great at the time they launched, they were simply never enough. After stage manager and the reaction users had to it, iPadOS stagnated for two years.
Today, Mark Gurman reports that they are going to try once again with iPadOS 19 to make the iPad a more advanced computing platform. Color me skeptical. Is this a fifth time’s the charm situation? I am trying to be optimistic, particularly after Apple nailed multitasking on visionOS. Plus, this could imply that they have been working on these improvements for three years given the lack of massive updates since iPadOS 16. Mark says that the update will “focus on productivity, multitasking and app window management — with an eye on the device operating more like a Mac.” That sounds promising, but it is unclear what that actually means. Combined with a visual redesign, this could be huge if they do not tiptoe again. Each time the company has attempted an iPad software update to make the device more Mac-like they try too hard to do something different and often end up making something inferior as a result. That cannot happen this time. I seriously hope that they know it.
The Week ChatGPT Truly Became an Assistant
Yesterday, OpenAI introduced a new feature under the radar that I think might have just changed everything.
ChatGPT has had a rudimentary “memory” system for quite some time. It lets the model look for important context in your messages, like your job or a particular spot you enjoy. It then saves things that it thinks might be relevant to your conversations with it in the future and stores them in your settings for you to decide what may be worth saving or deleting. It is, in essence, a customizable data retrieval system on top of the model. You can tell ChatGPT to remember things or just wait for it to realize something was essential. This is still the system primarily in-use by free users, but plus and pro members are now beginning to have access to what was internally called “Moonshine.”
On the surface, Moonshine sounds very simple. ChatGPT can now reference your previous conversations. But in reality, it makes the tool dramatically more intelligent — and personal. By being able to reference things you have talked about before without hoping that the model would catch it or by manually teaching it, it feels more like talking with a person than ever before. Dare I say, ChatGPT actually knows me now.
My ChatGPT knows what my current goals are, what projects I am working on, and what I am generally thinking about. I was already popping in my AirPods and talking with ChatGPT voice mode about problems or briefly messaging it for advice on the fly throughout my day. But this takes it to a whole new level, it is never starting from scratch.
It may fundamentally now know more about who I am than any social media or search algorithm before it. And unlike those algorithms, it is actually information that can be put to good use for my sake. It is not worried about what kind of socks I might want to buy, what celebrities I may be crushing on, or trying to make me feel inadequate. It is never trying to sell or market to me. ChatGPT is trying to help me actually accomplish something, whether it is a personal or professional goal.
After just one day, I have already been having far more fruitful conversations with ChatGPT. It feels like a sneak peek at what virtual assistants can really be.
Craig Saves the Day, Gives Engineers the Green Light to Use Off-the-Shelf LLMs
According to The Information, Apple is now letting engineers build products using third-party LLMs. This is a huge change that could seriously alter the course of Apple Intelligence. I have been a proponent of Apple shifting its focus from building somewhat mediocre closed first-party models to using powerful open-source third-party ones. The company is already so far behind its competitors, that I would rather they focus on making really good products rather than really good models. They may be able to do both simultaneously, but I suspect that Apple could ship spectacularly good products using off the shelf models sooner as other teams build first-party models for the future in secret.
Now that Gemini can see your screen on Android and Copilot can see your screen on Windows, these competing assistants are now truly on another level. They are really assistants in the truest sense of the word now that they can visually understand your context while you are using your devices. They make Android and Windows devices more compelling alternatives too. I am hopeful that Apple will be able to catch up much faster by doing what they do best, which is productizing advanced technology. The only difference is that this time, at least for now, they will be productizing someone else’s tech.
I imagine they will be largely looking at Mistral, Gemma, and Phi. Llama would be an obvious contender too if the company’s relationship with Meta was not so contentious. DeepSeek would be another option, though the optics of using it outside of China would likely not be ideal. We will just have to wait and see!
Microsoft is Filling in Essential Gaps on the Mac For the First Time in Decades
Microsoft has a long history of Mac software development. It is not something you often hear about anymore, but the company’s legacy is as intertwined with Apple’s as any other. I tend to be quite negative about Mac Office. I have never been a fan of PowerPoint, Excel, or Word. I was always an iWork guy personally, despite the flaws those three apps have. This is all to say that Microsoft now makes some of the nicest Mac apps there are. Yes, I cannot believe I just wrote that sentence. I am not talking about Office apps, I am talking about Copilot and Edge. OpenAI has gotten a lot of credit for its world-class Mac ChatGPT client. It is an excellent app, both from a functionality standpoint and in terms of its user interface. But Microsoft came out of nowhere with what I have to say, is a drop dead gorgeous native Copilot app.
Copilot on the Mac does not feel like a web wrapper. Today that is the best case scenario, the least you can hope for. It has fluid animations, a nice soothing color palette, and is blazing fast when answering prompts. It really just works. With the current Apple Intelligence situation, it is something that almost anyone who has a Mac should consider using. Not just because it is free, but because you get so much from that free version. From deep research with o1 to beautifully generated user interfaces for certain answers to a command bar you can bring up from anywhere, it fills a lot of needs. Microsoft’s decision to subsidize extensive usage also makes it what I think is one of, if not, the best free AI tool. Given the vast array of new features unveiled by Microsoft his past week for Copilot, I imagine that it is only going to get better. By the way, you should go watch the presentation if you have not. Mustafa Suleyman is an excellent presenter and does a great job walking through where they are heading with all of this. Thankfully, they are not gatekeeping all of these things to Windows. Microsoft has really filled a major gap in macOS for the first time since before Safari and iWork.
Now I know what you are thinking: “Why would I not just use the ChatGPT app?” That is completely valid and I am not saying one should replace it with Copilot. I think Copilot is a supplement. ChatGPT on the Mac is the best choice for working with code or text. It also happens to now be the best way to generate and edit images on the fly. But Copilot feels more personal and is faster at answering search queries. I have struggled in the past to figure out how the different large language models all fit into my workflow. I used to think that I had to use one or the other. But it is clear they are all sticking around, at least for now. I have altered my workflow to use ChatGPT while coding or designing, Claude while writing or as a back up for difficult coding issues, Gemini while working with Google apps as a sort of basic assistant on my phone, and now Copilot for casual use on the desktop. Others occasionally make their way in there, but this is largely how I am using these tools. At the end of the day, the Copilot Mac app is nearly as good as the ChatGPT app. And I would argue that it has one advantage, it is in the Mac App Store while ChatGPT is not.
Now I have heaped a ton of praise on the Copilot Mac app, but I mentioned that Edge has gotten really good as well. I bring this up largely in the context of changes at The Browser Company. I was a huge fan of Arc, but it is not my browser of choice anymore as I do not think I can count on them to keep iterating on it as they once did. I have tried a variety of clones, some of them are fine, but I am not sure how reliable they are long term. I have even been using the alpha of The Browser Company’s new app, Dia. But I will not say anything about that just yet, it is too early to tell where it is going. After all of this searching, I was so pleasantly surprised by the current state of Edge on the Mac. I used to use Edge in lieu of Chrome given how much less power intensive it was. But I was never particularly a fan of the user interface. Now it is arguably one of the best-looking Mac browsers. It also happens to be a true AI web browser with the Copilot sidebar, which now adopts the new design from the Mac app making it much more palatable. It has quick access to summarization and key points, but the best part is that it supports vertical tabs. Vertical tabs were the best part of Arc and they were implemented in such a powerful way that I have difficulty going back to horizontal ones. Thankfully Edge combines AI with vertical tabs and has a development roadmap that you can count on for the long haul. Arc users, I highly suggest trying the latest version of Edge. Port your chromium extensions over, reconfigure your vertical tabs, and you might just find yourself in a state of browser zen.
So yes, Microsoft now makes one of the best AI apps for the Mac and one of its best browsers. They are both well worth checking out if you have not used them in a while. I would not be surprised if many of you have not even tried the new Copilot app. I continue to be delighted by the experience and my usage of it keeps increasing. But the real story here goes back to what I said earlier, Microsoft is once again filling in gaps on the Mac. As Siri falls further behind and Safari continues to stagnate on the AI side, they have garnered an upper hand. They should not have to fill these gaps, but they saw the opening and they went for the jugular. They could have half-assed these tools, but they went all out making them on par or better than their Windows counterparts. I hope this spurs Apple to build a proper Siri app that tracks your conversations and uses the best models. I also hope this gets the Safari team thinking bigger about how they can incorporate AI and make browsing even more fun.
From a small garage in Los Altos to billions of pockets, wrists, ears, faces, desks, and living rooms. Happy 49th birthday Apple. Next year is the big one.
