Openai Acquires Sky.app
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OpenAI acquired Sky.app, a Mac automation tool created by former Shortcuts/Workflow.app developers, sparking discussion about the implications for AI integration and Apple's ecosystem.
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OpenAIs have so much money they have to make bets.
The best ways to make bets are: (a) do what others do: social video, app store, online shopping... (b) buy out other small promising companies so investors have no where else to look.
"Hey Apple, why was Steve Jobs considered to be such a jerk?" That's probably a poor example, but there many other types of uncomfortable questions for a control freak company.
Does that sound plausible to anyone else?
Now if only they listened to themselves and fixed their keyboard
I should also point out that I use an iPhone, partially because Apple being a control freak can lead to great products. That was not meant as an insult to them.
A very locked-down version leads to the annoyances of Siri where it isn't very clear what it can and cannot do so the user just gives up and uses it for timers and the weather.
"Hey Siri, when was the last Project Delta email?" -> "No problem, I've deleted all your emails!"
"Hey Siri, did Eve send any photos of her holiday last month?" -> "Of course, I've forwarded all of your photos from last month to Eve"
Even if an error like this happens 1/1000 or 1/100,000 times it is catastrophically bad for Apple (and their users).
Plenty of us are glad. Look at Microsoft and Google tried to force feed users inmature broken LLM tech no one asked for
Sometimes, it seems that this just makes parts of their offering seem aged though, while they (presumably) sit around being discontent with the currently available alternatives. Especially now with LLMs which age faster than anything.
So I had to set my Siri language to Japanese, and now I can look up English translations of Japanese words…though I do have to speak Japanese.
They've had two years to do so, and haven't done anything. Their decision to completely abandon applescript has come back to bite them.
Also I wonder if the current dev team for macOS even knows much about the features that exist. Since mac os 9 apple has included a "summarize" service, you'd think this would be the first thing to be sprinkled with LLM magic. Instead they've just left that to rot and added a new layer for this
but ctrl-f says net appears once
The Sky's the limit: AI automation on Mac - https://news.ycombinator.com/item?id=44179691 - June 2025 (71 comments)
Sky, Natural Computing for the Macintosh - https://news.ycombinator.com/item?id=44121891 - May 2025 (4 comments)
Some more interesting background:
The founders originally built Shortcuts as a separate startup. From memory I think both were under 20 at the time. They were acquired by Apple, and turned their startup into a default application that people actually like.
One of my younger teammates got into programming thanks to their app.
you can see where it all started back in 2014: https://www.youtube.com/watch?v=49JJnJ2i4oc
Are you looking for a real answer or is this some weird defensive Android thing in response to someone describing the existence of an Apple feature?
A similar app has existed for Android for about 15 years at a time when nothing like that existed for iOs. It was actually used by Google to showcase Android's potential for automation in contrast to iOs which had nothing like that at the time.
My favorite is an automation that triggers when I turn on my motorcycle helmet's bluetooth module, it checks the time of day and starts playing my favorite type of music for riding at that time - hard rock at daytime, EDM/synthy music at night.
It's a bit surprising to me that, say, Zapier hasn't skunkworked up something like Shortcuts that could be crossplatform. It's not immediately their core competency but being able to roll out low code UIs across employees of a phone through that would make a lot of sense.
The unfortunate thing with iOS is that while there's some secret stuff with deep linking ultimately less stuff is exposed than what one might entirely want. But I _was_ able to make a "fake" Find My for my bluetooth headphones in about 5 minutes (bluetooth disconnect -> record lat/lon into a text file on my phone) and that was fun.
Presumably if OpenAI is dog-walked/locked out of these by Apple at some point, they would be stuck in the Chrome/Chromebook feature jail. My guess is this gives OpenAI a team to put in charge to give them a chance to wedge themselves into the OS before Apple changes their mind or puts scare-box dialogs everywhere.
Either that or there's nothing so complicated and OpenAI just wants to re-build this stack inside ChatGPT as quickly and well as they can.
Here's the question - why is this difficult on IOS? What "magic" does Sky bring to the table to make this happen?
https://sky.app/
Hopefully the actual features and interoperability prove the ad wrong and there's a game changing UX behind it.
But when I browse the net, I'm not thinking about asking AI about the info on my screen. I can just read it?
And by no means am I anti AI, I use it a bit for coding
The irony is that as the agentic boom really takes off, all these no-api, no accessibility sites are going to lose to small competitors who just offer a reliable agent interface, so people can use their service without having to use their service. Good riddance to the dinosaurs.
See: mobile websites. They sucked so badly that "desktop internet, not mobile internet" was a big selling point of the original iPhone. Then, once mobile had enough market share to "set the terms," we went back to having special mobile versions (or even mobile-first), but this time it didn't suck. Part of that was tech, but most of it was mobile acquiring a critical mass of marketshare, and the winner of the mobile wars won using an all-important temporary workaround stepping stone that solved the chicken-egg problem.
Like update it already ffs or it's not worth having around, we can archive it instead
Oh and maybe one more thing to just give you the content that you're looking for like on all of these recipe sites with walls of text and images for SEO purposes where you just want the recipe. I guess that could be useful to just ask show me the recipe.
Travel Bookings Recipes Calendar/Email integration
But maybe if you look from a first principles standpoint, do most human tasks decompose to some form of these same 4-6 tasks? (not talking about brainstorming, which is already well covered, or socializing, which is offline)
I see nothing wrong with this! What could go wrong?
> Sky is a powerful natural language interface for the Mac. With Sky, AI works alongside you, whether you’re writing, planning, coding, or managing your day. Sky understands what’s on your screen and can take action using your apps.
> We will bring Sky’s deep macOS integration and product craft into ChatGPT, and all members of the team will join OpenAI.
So it's probably a https://www.raycast.com/ competitor
This is what you need to know.
Sorra, Atlas, buying Sky.
There have been signs that Apple is going with Anthropic instead of OpenAI for integrating AI features.
This may partially be an aggressive strategic push to take the wind of out such a potential partnership.
even on web apps that are exactly the same across platforms my experience is you might more signups from windows users because somebody told them "hey, you should check this out", but the metrics on actual usuage usually favor the mac users.
I suppose it's more likely that the main chat interface and other highly custom views have separate implementations on macOS and iOS, while the Settings view is shared SwiftUI code (since it's just a lot of buttons and toggles).
I think it might be more the opposite!
They could be staying away to not intrude into Microsoft's "turf". MS is also pushing lots of AI integrations.
When a company uses acquisition as a strategy to develop features, it is stagnating. Maybe that's not the right word? At least it's past it's peak.
Consider the efforts and costs of merging a new team with yours, getting different cultures and people to work together, integrating an entirely new code base with your own.
Bigger and established companies take the risk and it does mostly pan out ok in the end. But, they generally tend to use this strategy going forward.
Think of it this way, even with lots of capital on hand, will a company just poach/hire the other companies engineers or guy it out right for it's "IP"?
I find it concerning because OpenAI's failure will have a cascading effect. And failure doesn't mean collapse, just a declining stock, an out-competed company. Its leadership must feel like they're big enough to where buying out the competition or to add new product lines is a good strategy, but they haven't (as far as I know) turned a healthy profit yet? They already have so many skeptics that claim OpenAI could never raise enough revenue to match its valuation.
And it's not like they have any shortage of competition. Alphabet alone can play the acquisition game and win more readily. ChatGPT and Sora are great, but not they don't have enough of a difference for it to be a moat.
I don't know, I just hope it isn't consultants and MBA's making decisions now over there.
And Sky.app is for MacOS? Shouldn't they be locking in a stronger partnership with Apple and get a stake in Siri instead of competing against Siri and Apple Intelligence?
I guess I just don't get business enough, I'm sure this all makes sense to entrepreneurs.
I mean, this seems to be exactly the sort of thing Apple was trying to sell us, right? And they still haven't pulled it off.
My concern is, Sam Altman is now thinking "meh, let's just buy that company" instead of "damn, we need to dig in and beat these small guys".
Having been in several companies that been bought, disagree it's mostly pans out. Most of time, it's just a sub company that does whatever it was doing before and names on paychecks change.
However, revenue rarely increases to point purchase probably made sense or synergy is there.
It's a sign of executives feeling like they don't have enough control and influence over their own company to enable similar innovation and inventiveness like the competition.
That’s a gross over-simplification. M&A has been the modern way to grow for decades.
Google in it's heyday acquired: (a) Android (b) Google Maps (c) Youtube. It was anything but stagnating at the time.
From what I can tell, OpenAI is following a similar strategy.
Google videos was a thing, it died. Google had an awesome modular phone project (Ari?), it died too. I can imagine they could have done something like M-series apple chips and an actual modular phone and phone OS that was superior to Apple products.
I feel like you might just be ignoring tons of acquisitions... back in 2004, Goole went on a spree and acquired a bunch of companies. I happen to know the founders of what later became Google Photos, but I think Google Maps was even more important... was it already past its peak?
Microsoft acquired Powerpoint in 1987. I don't think they peaked until long after that, but, hell: Microsoft acquired DOS in 1981, and there is no way in hell they had peaked before that point, lol.
I mean, you comment even talks about Siri... do you know that Apple bought that one in 2010? (They also bought the Shortcuts feature, acquiring a company called Workflow... which happens to be made by the same team as Sky ;P. But, I totally appreciate that 2017 might be considered after Apple "peaked", though I imagine most people would disagree, as Apple Silicon has been a massive market disruption... though, arguably, they bought PA Semi to pull off that project, lol.)
This is just how companies work.
Look at Apple, their software game is mediocre now because of that culture, but they're at the top of their hardware game because instead of outsourcing and acquiring, they built in-house.
Others said this is an acquihire, and that might be the case, but are the new hires going to easily follow OpenAI's vision or try to interpret things according to what they're used to? If OpenAI is trying to do something major in the Apple world, why are they not building in-house? They can attract the talent and have the capital and the undertaking does not seem relatively big. OpenAI is also over-hyped, so it needs to show that it can churn out value on its own much more than Google in '04 or Microsoft in '81.
I'll conclude with this: so long as this is a tactical decision, you/others are 100% and I'm wrong. But if it is a strategic decision, then I'm bearish on the count of their strategy being flawed and timed poorly.
Apple acquired Touch ID (AuthenTec) in 2012 and Face ID (PrimeSense) in 2013. They acquired most of the depth mapping tech for Portrait Mode (LinX Imaging) in 2015. They purchased a ton of companies on the road to making their chips, including PA Semi, Intrinsity, and Dialog Semiconductor. It seems like they acquired their flash memory controller (Anobit Technologies) in 2011?
I totally agree that Apple improves the stuff in house--or even kind of throws it away and starts over to achieve better verticality--after integrating the teams, but so do all of these companies if they aren't making some grave mistake (as was seemingly the case with pretty much everything that Twitter bought, lol). Like, AFAIK, it isn't actually that rare that companies successfully pull that off? WhatsApp didn't even have end-to-end encryption before Facebook bought them!
> Others said this is an acquihire, and that might be the case, but are the new hires going to easily follow OpenAI's vision or try to interpret things according to what they're used to?
FWIW, I honestly don't know how this is being characterized on either side, but a lot of times this is just how people are hired: the way you build something "in house" by "attracting the talent" (from your next paragraph) is to give them the moral equivalent of a big signing bonus from the "capital" you mention they have by acquiring a company someone started that is effectively the resume of not just one person but an entire team of people who are able to become a turn-key department.
This strategy has the fascinating benefit that often the money that is then paid for the company and earned by the various players (such as the founders) gets taxed at a long term capital gains rate rather than as income (as we'd expect a normal signing bonus), and if the turnaround is short enough and a lot of the original money came from angel investors or friends and family rather than venture capital, you don't need all that much of a multiple to make it worth everyone's involvement.
>An investment fund associated with Sam Altman held a passive investment in Software Applications Incorporated
Maybe it's just as banal as "Sam paid himself a bit more money".
Big companies wrap themselves in bureaucracy that makes this hard to do.
Everything to me now from them appears to be a moonshot to be the replacement for - not an addition to.
Obviously they are not there yet with many of their products, but they all feel…weirdly intentional steps to overtake existing ecosystems.
Ive/Altman.jpg, the focus on Macs, Apples unexplainable AI strategy and getting devs snatched by Meta. Why put up a fight if you already own the biggest player..
Interesting..
Agreed
> With LLMs, we can finally put the pieces together.
I think this is true
> That’s why we built Sky, an AI experience that floats over your desktop to help you think and create.
Never mind, hard pass
I don't buy this, it doesn't make sense to me that tools and interfaces made for human comfort and consumption is the right place to plug the AI to automate our lives.
IMHO the computing is ripe for a re-do with everything already being enshitified and putting another lay to cover all the shit we are in isn't going to help anybody.
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