The Past, Present, and Future of Building on Apple — John Gruber, Daring Fireball

David Barnard:

Welcome to the Sub Club Podcast, a show dedicated to the best practices for building and growing app businesses. We sit down with the entrepreneurs, investors, and builders behind the most successful apps in the world to learn from their successes and failures. Sub Club is brought to you by RevenueCat, thousands of the world's best apps trust RevenueCat to power in-app purchases, manage customers, and grow revenue across iOS, Android, and the web. You can learn more at revenuecat.com. Let's get into the show. Hello, I'm your host, David Barnard. My guest today is John Gruber, Raconteur, Apple aficionado, podcast host and sole proprietor of Daring Fireball. On the podcast, I talk with John about the fascinating 40-year history of Apple's developer relations, how almost going bankrupt in the '90s shaped today's control-focused approach and why we might need an App Store 3.0 reset. Hey, John, thanks so much for coming back on the podcast.

John Gruber:

Well, you've been on my show. I hope to have you on my show again soon, so it's the least I can do. I'm happy to be here.

David Barnard:

So today, I want to talk Apple Kremlinology, which I think is maybe a great term. I just threw it out there. Apple is such a unique organization that... And for most developers, it's like our most important partner. And I'm doing air quotes for those listening on the podcast. And I don't think a lot of people understand Apple, and I think a lot of how people interact with Apple, what they think of Apple is shaped by just not understanding them, which is maybe on Apple. But that's what I wanted to talk about today was better understanding Apple. And I think of all the people to have this conversation with, it's going to be really fun to have it with you.

John Gruber:

I appreciate that and only because, and I hate to flatter myself. I really do. I really do. I try to stay as humble as possible. I feel like that's what keeps me in the game. But understanding Apple to me is maybe one of the top three things I have. I really....

David Barnard:

Yeah. Yeah, totally.

John Gruber:

And there's always been an intuitive, oh, I love this company vibe fit and some other rolls of the dice of the way my life could have worked out surely on many of the other rolls of the dice. I end up working at Apple for some amount of time, possibly a very short amount of time, because every time I've ever had a job in my life where I actually am not self-employed has not lasted all that long. So probably not long, but one of my earliest memories, I think it was either fifth or sixth grade, which was early '80s, probably like 1983, '84, I just remember reading a story about Apple Computer and I knew at the time that I liked Apple Computers better than other company's computers, and I loved computers.

But I remember reading a story about the company and reading that all of the employees just show up to work in sneakers and jeans and T-shirts and that they wear clever T-shirts and they make. Every time they start a new project, the first job is to print up T-shirts for the team for the new project, and then they wear them to work. And I remember thinking, that's awesome because I don't want to wear a freaking suit and tie to work. And I remember telling my dad this and my dad telling me, "John, there is no way that a major computer company lets the people show up to work in jeans and T-shirts." And I was like, "No, I'm telling you, dad, I read it in a magazine. It's true."

David Barnard:

That's awesome. And then not to flutter myself, but while we're... We should have scripted this, and I should have done this for you and you should have done this for me, but I relied on ChatGPT pretty heavily to do research for the show because I wanted to go really in-depth in the history of Apple and their relationships with developers. And last night, I'm getting through my notes and ChatGPT says, "Three of the prominent voices in App Store related topics are John Gruber, Ben Thompson and David Barnard." And I don't know if it knew it was me and was freaking trying to flatter me or whatever, but I mean, similar to you in a way that the App Store is something I'm unreasonably passionate about. I have an emotional attachment to the App Store and care so deeply about it. And in part, and you know I've discussed this, I was a recording engineer and I knew that was kind of a dead end as far as having a family and being able to provide and stuff like that.

But I was a huge Apple nerd, so I got a 17-inch PowerBook in 2003. So my Apple journey begins a little later. I mean, I used them in college and I played with a original Mac in the '80s, but my real Apple fanboyism started in 2002, 2003. So I jumped right into the App Store in 2008 thinking, "Okay, this is an opportunity to build a real career that's going to provide for my family." And it did. I'm 17 years into owning an app business and I care so deeply about the store and then also care so deeply about Apple. And so everything we're going to talk about today, it's like you being one of the people who cares the most about Apple, who's outside Apple, and me, one of the people who cares the most about the App Store outside of Apple, I think is the two right people to have this kind of conversation. And maybe we should have had Ben on and to have a third voice, but...

John Gruber:

There are certain things that I just remember which years they were, and I just remember that 2007 iPhone no App Store, 2008 App Store comes out. 2009, it really takes off and coincides really with the go-go years of Twitter. And that's absolutely 100%, there's no confusion. I mean, maybe you sent me an email at daringfireball.net or something, but where I remember getting to know you was on Twitter, and I just remember like it's one of the great privileges of my position doing what I do with Daring Fireball where it's like, "Oh, I'm going to get to know this guy," and we'd at each other on Twitter about App Store issues, but I was like, "This guy," I could sense both your profound enthusiasm for it and the way that it was making you... It wasn't making a fanboy of the App Store where no matter what you wanted to say, "Oh, I love the App Store. So no matter what, I'm going to make my conclusion, whatever changes they make are great."

Your enthusiasm was such that you're like, "I want to understand every single thing about this to the deepest degree." And again, it's sort of like a laziness where I'm like, "Oh, if I become friends with this guy," and I've got a Rolodex of people who are experts on whatever, it could be AppKit, could be UIKit, could be the App Store, could be... And you're at the top of the list for the App store and have been since 2009 and probably should have been since 2008. But I just remember, 2009, you were just a key follow on Twitter for App Store related stuff, and it was such a fascinating time, explosive, just an explosive time.

David Barnard:

Well, and I was a Gruber fanboy, and you linking to my app in the fall of 2008, I think wasn't part of turning point. I mean, they were key people who helped me along the way, including people inside Apple. And I remember vividly...

John Gruber:

It was the Launcher app, right? What was it called?

David Barnard:

No, no, no, this was 2008. You linked to my mileage logging app. When the App Store launched, there was this terrible Windows phone ish, horrible user interface, no kind of Mac or iOS interface paradigm, a mileage log. They got there first, which is still eats me to this day. 17 years later, I missed the launch of the App Store because Apple did not approve my developer account. And so a month later, I release a mileage log, it was like we follow the iOS paradigms, I mean, looking back, I don't ever feel like I had the best taste, but I didn't have... It was brown and it was not the prettiest or most, but it was iOS. We used the paradigms of iOS. We built a native app. And so you link to that in the fall of 2008, and it was a turning point.

John Gruber:

Well, I'm happy, I remember that. And that was the other thing that I remember about you is it wasn't just that you were obsessive about the App Store, is that you actually had skin in the game, and that you clearly... Again, I'm not just trying to butter you up here, but no, but there was at that time, at the very highest level when they first announced the iPhone and said, "Hey," and underneath it was one of the... It wasn't called a Bento box at the time. They did the slides in a different style. But at Steve Jobs original introduction, they had a bunch of things on a slide and they said Cocoa, that everything Apple had done for the original iPhone, before the iPhone, before the App Store, and before they announced, famously took them several months before they said, "Okay, we're going to do an SDK," but they said that they were using Cocoa.

There's like a five-minute podcast Merlin Mann did at Macworld Expo talking to me and Jason Snell, the day of the keynote on the floor, it was like a five-minute interview with me and Snell by Merlin Mann. And Snell and I were like, "Apple didn't say much about this Cocoa thing, but presumably at some point, it's just probably not ready yet. They're going to open up APIs and this is going to be huge." I mean, this was hours after the keynote when we were still euphoric about the whole thing because everybody was sort of looking forward to just an iPod phone, right?

David Barnard:

Right.

John Gruber:

And it was so much more, it felt like my mind had gotten significantly bigger during the keynote. My brain had grown because the realm of possibility of personal computing was suddenly much larger than I thought. But in that initial moment, most developers were thinking was, "Well, that's fantastic if they're Xocoa APIs," and UIKits slightly different than AppKit, but every single AppKit going back to next developer I know looked at the initial UIKit APIs and was like, "Oh, all right, this is different, but I know this, this is very familiar." But the idea that developers had was how do you take ideas that are good Mac apps and put them on the phone? And for many apps, that was a great idea and Apple itself did that, right? Safari, mail, how do you take mail and make a version that fits on the phone?

But the opportunity that I think Mac developers didn't think of right away is what sort of ideas only make sense for a phone, a little pocket, 3.5 inch screen device that's with you all the time. That wouldn't make sense on a Mac and a mileage tracker is exactly that sort of idea. That's what I remember hitting me about that app in 2008. Like, oh, this would be stupid on the Mac. What are you going to do? Take your MacBook or PowerBook? I forget what, I guess they were MacBook set by 2008, but what are you going to do? Take a laptop with you in your car everywhere and log your gas and mileage? No, but for something that would replace what you would've done in a pocket notebook, that's a perfect idea. Obviously, people want this. And that's where I feel like you were ahead of me and I'm like, "I got to follow this guy because he's thinking about things that are phone first."

David Barnard:

Right. Yeah. Well, enough navel-gazing. I'm blushing. But I appreciate all of that. And again, just the perfect person to have this kind of conversation with, which I've wanted to have this conversation for a while in service of the community of... In my day job at RevenueCat, and I do still build apps on the side, so I'm still an indie developer, I was looking at my LinkedIn the other day and 17 years at Contrast and still going strong, still running my weather app on the side and stuff. So at my day job at RevenueCat, I interface with a ton of developers and a lot of them don't care one lick about Apple, in fact, I mean, the growing hostility, people who've never built an app before will book an office hours call with me and say, "Screw Apple, screw them in their 30%."

There's no care for Apple as a company or the products or anything like that. And so I wanted to do this podcast to give some of that history. I was actually thinking as I was preparing these notes, it's almost a book at some point, the history of the App Store and how it shaped the world. I mean, so many decisions that Apple made, big and small, literally did shape how things happen, and we'll get into some of that. But I wanted to step all the way back, and again, in doing the research for this over the weekend, I saw something that really surprised me, and I think I knew this, but I hadn't seen the numbers. And that is that the three top executives at Apple whose teams work on the app store. So I think maybe, and Apple is famously secretive about who does what and who reports to who and those kinds of things. But from my understanding...

John Gruber:

They're secretive about everything, David.

David Barnard:

Everything, yeah. Yeah. Something like 90% of the people who interface with developers in the App Store who work on the App Store report up to three executives. Greg Joswiak, who joined Apple in 1986.

John Gruber:

Yeah, I think right out of college. He went to University of Michigan and went right to Apple.

David Barnard:

Phil Schiller, who joined Apple in 1987, and Eddy Cue who joined Apple in 1989. And so to really understand Apple and how they interact with developers and how they receive the developer community, you really do have to go all the way back to the 1980s when these three key executives joined and started, and each of them have their different role in developer relations over time. But going back to that 1984 release of the Mac and these early days of developer relations between Apple and developers, I think is so fascinating, and one of the things, again, I didn't eve... I knew, but seeing it again in black and white, just how instrumental Microsoft was in those early days to Apple that two years ahead of the 1984 release of the Mac, Microsoft had agreed to build products for this new platform. And then specifically, and again, never heard this before, but Bill Gates was kind of an Apple fanboy in some of the early days before they got really contentious.

And I read this history piece about the history of Apple that said Gates would show up to events, Macworld and other events with Macintosh shirts, he would wear a Macintosh. I mean, can you even imagine Bill Gates in the '80s wearing Macintosh T-shirt? It was just such a different era. But then over time, developer relations started to get a bit contentious. What do you remember? I mean, you were, gosh, like 6, 8, 10 at the time when all this happened. And I was five. But we both read a lot about the history. So what do you recall? And then what do you remember from having read upon all this.

John Gruber:

Too young to have experienced those years extemporaneously, but from what I've read, one of the key superpowers that Gates had, and I think it's true, I think this is not an original observation, but no matter how big, and no matter even... I mean, I guess eventually after, when you get closer to 50 years, which Apple and Microsoft are at, but maybe closer to a century after entire original generations have clearly all died off, it fades away. But all companies in all fields are just infused with the personalities of their founders. And one of the things that Gates infused in Microsoft was an amazing willingness or just natural ability. I don't even think it was something he did purposefully. I think it's just the way his mind worked is he was always thinking what could be and was not attached to the way things were. The whole name Microsoft, the whole idea that revolution of the company was, "Hey, we could make a company."

This was him and Paul Allen that just focuses on software and had no plans in those early days to make their own computer. And all of the action in the late '70s at that moment of the PC revolution, the late '70s and the early '80s was on the company's making computers, Apple and Commodore and Texas Instruments, you name it, IBM, once they made the PC and Microsoft's key insight was, "Hey, software is incredibly valuable." And at the time, that idea alone was revolutionary. It was absolutely revolutionary because everybody else thought the only thing that matters is computers and computers were all absurdly expensive. Just look at the memory that was in those computers. The Commodore 64 was called the 64, not because it was 64 bit, but because it had 64 kilobytes of RAM, right? That was the 64, and it wasn't cheap, cheap.

And the idea was software, you just copy, it was just ones and zeros. You could just make copies. And the idea that no, no software is worth paying for was a revolution. And I think that's why Gates could have such incredible enthusiasm for something like some other company's computer because everything they did was for somebody else's computer. They didn't make computers and they didn't really have a platform. And so I think Gates recognized early that Apple made better computers and that they were onto something. And he clearly, from the outset, had the mindset of the complete opposite of, I forget his name, but the 1960s era, IBM CEO who said, "I think there's a market in the world for six or seven computers."

Because the thinking in that era was, well, the US military will want one, maybe like the US IRS, and there'll be one great supercomputer for universities to share. Whereas Gates was really thinking early on, "Oh no, there should be computers in every house." But he wasn't thinking that Microsoft would own a platform. But then when the opportunity came with DOS and they saw the opportunity they had by owning MS-DOS and being the company that provided it, it changed their thinking completely to instead of, oh, we'll make software for anybody's computer. We're going to make a platform and we'll still make some software for other platforms, but we really want to steer everybody to our platform even though we don't make the computers.

David Barnard:

One of the interesting footnotes in this as well is that Apple had a similar idea of we're building this platform, we need to make sure there's software on it. And so they built Mac, right? MacPaint, MacDraw, and a bunch of other apps. And again, something I didn't realize until doing all this research was that in 1986, they stopped bundling those because it was competitive with third-party developers. And man, I mean, these days with sherlocking and Apple building an app for everything, I mean, even most recently building an invite app like building a sports app, Apple has over the last 17 years of the App Store gone deeper and deeper and further and further into competing directly with third-party developers.

But back here in the '80s, they were like, "Whoa, whoa, whoa, whoa. We don't want to squash the potential for third-party developers to build for this platform that we have. So these apps that we built for our own platform that we have previously bundled," I mean, again, at some point maybe when Schiller or Jos or one of these guys retires, we'll do this again and get the inside scoop on some of the deeper thinking behind this. But they stopped bundling, and then in 1987, they spun all those apps off into Claris, a subsidiary of Apple to have them at little bit more of an arm's length. It's specifically to not interfere with third-party developers. And it's still fascinating to go all the way back to the '80s and see such a different Apple that they recognized the power of developers in the platform and were actively doing things at that time to make sure they didn't compete. They didn't make it a non-starter for people to build these kind of apps for the Macintosh platform, which is just fascinating.

John Gruber:

And it was about a decade, I would say maybe '86, '87, and those are the years where I was there as a teenager into college, and '86 to '95, '96 or so was the decade where Apple was very hands-off about first-party apps and it made sense. And one of the areas of contention, it's sort of like a heartbreak, and I forget the exact details. I know Andy Hertzfeld's wonderful, wonderful... I think there's a story about it on Folklore.org, but you can look it up. But there were two basics, the basic programming language for the Mac in the very early '80s and Apple Basic was much better and could let you do Macintosh-like things like pop open a dialog box, which you think like, well, of course, why would you want to have a programming environment for the Mac that couldn't pop open a dialog box? But that was revolutionary at the time, and Microsoft had their basic, and as like a, let's keep Microsoft happy, Apple sort of squashed their own in-house basic, which was a much better programming environment for the Macintosh.

So as not to step on the toes of Microsoft Basic, which was more of a oh, character based sort of text interface basic, where you could write the same Microsoft Basic program and run it on the Mac and run it on any other computer that had Microsoft Basic. And that's just one example of that sort of thinking and this sort of thing that led them to spin off the initial, which they had to do again because nobody knew how to write these graphical user interface programs. It often comes up and people, you have to Google the images to believe it, but the original Macintosh keyboard didn't have arrow keys because they wanted to force developers and users to use the mouse as opposed to almost all other computers at the time didn't even have mice. So there was the Macintosh, which had a mouse and other computers which had no pointer interface, just a keyboard interface.

So you'd be like, "What do you want to do in the computer?" And it would present a text menu and you'd use arrow keys to go up and down. I want to open existing file down. I want to create a new file down. I want to manage my files up, down, left, right. So to force developers to make programs that were mouse driven, mouse pointer driven. Apple didn't even put arrow keys on the original Macintosh keyboard, which imagine the frustration editing text now. So if you wanted to, you could backspace, there was a delete key, but if you wanted to go back a word or two, you had to go take your hands off the keyboard, go to the mouse and click where you wanted to go. But I understand why that didn't last, but I also understand the thinking at the time to break people's habits because as much as they thought this is a computer for the rest of us, which was their slogan, and this will be the way that most people in the future learn to use computers.

Right now, the market is people who already know how to use computers, but what they know from the existing computers isn't the way this computer works. And so they had to make apps like MacWrite and MacPaint and MacDraw, and then two years in, they're like, "Ah, we're kind of squashing the market. What we really need is a thriving third party market, so let's go hands off." And then for the next decade, the Mac really didn't have many first party programs. If you just went to the store and bought a brand new Macintosh in 1991 or '92, you got TextEdit or it was called SimpleText at the time. There were very few apps that were built in. There was no built-in Contacts app. You didn't have all these things that you would think, "Oh, how do you have a computer without an address book?" Well, the idea was that whole thing was a third party opportunity.

David Barnard:

And this is a great example of why I wanted to have this conversation, and maybe we'll pull on some of these threads as we go through. One thing to understand about Apple and how they operate today is that they've had success in doing those sorts of things. And so when you look at Apple TV that famously launched, and Apple tried to get people to develop games for it, but you could only use the Apple remote, and it was Apple as with the keyboard not having arrow keys, it was, we don't want people to require a gaming controller to build games, so we're going to force them to use remote. And games sucked, and I was so pissed at Apple, it took them, what, three or four years to finally enable controller support. And by that time, it was just so clear that Apple TV was not going to be a gaming platform, maybe could have been more of a gaming platform had they done it, maybe it was the right choice, whatever.

And then look at the Vision Pro. Two years ago, I was so frustrated that Apple didn't release motion track controllers like what you have on the Meta Quest, but why did they do that? It goes all the way back to 1984 and not having the arrow keys, it was, "Hey, we're introducing a new user interface paradigm, a new user experience, and we want to force developers to build apps that use hand gestures and eye tracking and not controllers." Now, two years later, they just announced at WABC that PlayStation VR controller support in Vision Pro, but this is two years after the fact, and I was so frustrated two years ago. But this is one of those things when you look back, you better understand why they make the decisions they make. They have a long history of making those kinds of decisions going all the way back to the '80s and forcing developers into the path that they think is best for the platform is just so fascinating.

John Gruber:

I keep repeating it. I'm more bullish on visionOS as a platform than most commentators, and I keep drawing the analogy to the original Macintosh, the original Macintosh in 1984, I know the number off the top of my head because I bring it up all the time. It was $2,500, which inflation adjusted is give or take right now, like $7,200. There was only one config. There was no option to get more RAM. There was no storage, you used floppy drives. So $2,500, it was 7,200 equivalent today about twice the cost of a Vision Pro, very expensive. It's sold so poorly and so under their expectations that it was the impetus for driving jobs out of the company. And in the whole, people don't know the history, like how in the world did Apple kick Steve Jobs out of the company? The real reasons were mostly personality conflicts, and that yes, of course, he did not work well when there was somebody else, John Sculley from Pepsi as the CEO who Jobs, the founder, ostensibly reported to, of course, Jobs did not work well as anything but the CEO, and that's ultimately the reason.

But in terms of going to the board and having reasons other than this guy's a pain in my ass, to force him out, the sales of the Mac were the... And again, it was expensive and Apple couldn't really afford the fact that it was a bit of a flop in 1984, 1985, but the PC press of the time took it as, "Hey, this whole graphical user interface thing, it's clever, but it's a gimmick. This isn't how real computer users want to use a computer. Nobody wants to take their hands off the keyboard and use a mouse all the time. It's a waste of memory to be drawing all these windows and stuff like this." That was all proven wrong. The Mac was the right idea for the future of personal computing, but it needed at least four or five years before you're like, "Holy, shit, this is like a thriving platform that's revolutionizing certain industries like desktop publishing."

David Barnard:

Yeah. And as a 40, almost 50-year-old company, I guess next year it's 50 years, somewhere around there. Apple's patience is remarkable. This is another thing that I continually get wrong, and I think a lot of people get wrong. 100% agree on the Vision Pro. It is a phenomenal piece of hardware. It is an incredible platform for experimenting with the future, even if it's flawed and even if there are problems. But Apple's patient, and clearly they have AR stuff in the labs that Cook and others have played with. There's been reporting recently about all Tim Cook thinks about is getting to this AR glasses future or whatever it might be.

And the Vision Pro is that first step along the way, and Apple is very patient, as much as people pan it as few units as they sold, even if it's been less successful as they internally hope for, they are nothing if not a patient company that's going to keep plugging away at these things. Because look how it turned out for the Mac, like you said, it took four or five years. Well, I mean, we're two years into the Vision Pro. They've got time and they've got cash to wait around and they've got the experience of building these platforms over decades, not making sure something is a hit in months and days.

John Gruber:

This is only based on observation, but I think I almost see how can somebody refute this is that their thinking is basically if their projection of where a hit AR/VR, let's just put aside whether the first hit product in the category will be AR or VR, but it'll probably be AR, right? VR is just too weird where my definition of the difference, the broad difference here is if the device is off, powered off, can you see anything or do you see through glasses, right? If it's glasses that when the device is at 0% battery powered off, you still see through the lenses, that's AR. And if it's like Vision Pro where it's off, it's like blindfolds, that's VR, it's probably AR, but let's just say it doesn't matter. Put that aside, that it'll take till around 2030 to have a product at a price and a feature set and a battery life that's compelling to explode in popularity and that people will be like, "I got to get one of those."

If it's 2030, when that's going to come out, what's the right way to approach the market? And I think the people who are laughing at Vision Pro and saying, "It's $3,500, nobody's bought one. They've only sold hundreds of thousands, not even a million, whatever." Apple should have waited until then to release a product, and then boom, here's the first thing. And the iPhone was sort of like that, right? And the iPhone was right out of the gate. Yes, it was a little more expensive, but the first iPhone was incredibly useful, totally credible device. And I know it didn't sell in great quantities compared to today's numbers, but as somebody who bought one, it was like, "Yeah, this is real." And it's not like I'm buying a product that hints at a future. The Vision Pro is not like that. The Vision Pro is not the iPhone in 2007.

The Vision Pro today, I don't like calling it a dev kit, but it's like an enthusiast kit, which includes developers, but it's an enthusiast kit that you spend a ridiculous amount of money compared to a MacBook Air. You get a really good MacBook Air for $1,000, or you could get a really good MacBook Air for 1,300, $1,400. This is three times, four times more expensive and it's less essential to people's lives than their iPhone, which you can get a really good iPhone for seven, $800. It's different than that, but is the right strategy to wait until that hardware is out in 2030 and then start there with building a platform or is the right strategy to start building a platform around 2023, 2024, and when that hardware is finally available and there's a breakthrough in the technology and the price and the capabilities in the battery life that you've got five years of ecosystem and content behind it.

All these complaints, again, I've complained too and I'm a little surprised, but they're getting there, just in terms of having entertaining immersive content, the things like the Bono video and the adventure climbing mountains and all this stuff. They've got some stuff, you would think with their budget that they could have more, but the idea of, hey, if they're going to sell this thing for all this money, shouldn't they have more content available? Well, if 2030 is when they think this is going to explode, think of how much content they're going to have in the library by then. And I think that's what they know. There are so many similarities between this and the Macintosh in 1984, but there are also so many profound differences because Apple is so big and so pervasive in popular culture and people's lives.

And it breeds a different sentiment towards the company, which I think we're going to continue talking about with developer relations. But then on the other hand, their profound, almost unfathomable financial success gives them the liberty of saying, "We're going to make a seven-year bet that costs a lot of money," just in terms of this thousand or so software engineers who work on Vision stuff inside the company. We're going to make a profound bet to build this out over half a decade so that when the hardware's really there for a mass-market thing, we've got it. We've already got the platform, we've already got the UI paradigms nailed down, we've got the input, we've got the sensors. We're going to be...

John Gruber:

... nailed down. We've got the input, we've got the sensors. We're going to be there five years ahead of time. It's a very different way of thinking than a company that is sweating it out. Are we still going to be in business two quarters from now?

David Barnard:

Yeah, and I think that's part of the pushback is that too many people, especially in the press, continue to expect every product Apple releases to be the next iPhone. And the iPhone is just singular in history as a consumer electronic device that it was able to come out of the gate as such an incredible useful day one thing. Because even, and again, I mean, this is why we're having this conversation. You go back to 1984, the $2,500, which is $7,200 a day or whatever it is, was not a daily driver, this is changing my life, most productive thing in the world. It was a nice to have, it was an enthusiast, it was something to tinker with and maybe you find a few productivity things here and there that it benefits. Apple has done this decade after decade after decade, and they have that long vision.

And again, going back to these execs who've been around through it all, it's like they've seen it happen and they know it will happen and they know it can happen. And to your point, they're not under that pressure of the Vision Pro has to be the iPhone. It doesn't have to be the iPhone. We've done this 10 times before with different products with transitioning from Power PC to Intel, with early days of iMac and it becoming a consumer hit that wasn't even the massive smash hit compared to the iPhone. And so it's like they know how to build platforms over decades and not over months and years that everybody else expects it to happen.

John Gruber:

So the one difference, and it is almost the same thing but along a different vector where I said about Gates and the way that Gates instilled in Microsoft a sort of flexibility in thinking like, hey, what's the opportunities right now? I think Satya Nadella's era as CEO embodies that where I feel like he came in and was like, you know what? We don't have to be all about Windows, Windows, Windows. We can go to more of a cloud first mindset and look at where they are financially and in cloud services and stuff. It's been a great deal for them, but that they got their institutional fortitude is once we have a hit, we will latch onto it and try to stick with it and ride it all the way down. And that was the whole mindset with Windows. Windows everywhere and they're going to put Windows on your TV set-top box and Windows phone, right?

And they were trying to make smartphones years before the iPhone and literally they had a start menu in the lower left corner. It looked like Windows 95 but on a phone and it wasn't running Windows apps, but it was a mindset of bringing Windows mentality. Whereas Apple's mindset led by Steve Jobs was let's start from scratch. And as much as they wound up using the Cocoa APIs and made UI kit, it was only not because that was a starting point. It was like, okay, if we're going to do this, maybe we could fit a small version of the Mac kernel onto this device and we'll build it, but we're not going to have any compatibility. It's not going to be called the Mac phone. We're not going to have an Apple menu up in the upper left corner. We're going to rethink this whole thing from scratch.

Apple has this sort of, if it's a new form factor, we're going to start with a new platform and that's a very different thinking, but at another level, just in terms of its capabilities, the reason the iPhone could debut in 2007 as a totally credible, you could buy one right now, the first one totally useful is that it's ultimately, and this is the unifying theme of the last five years of dithering with me and Ben Thompson, is that the biggest marketing shame of the entire industry is that we wasted the term personal computer on desktop and laptop computers in 1980 because the phone is ultimately the personal computer. And that's where everything was heading from the Apple One in 1977 until 2007. Everything was heading towards building something under $1,000 that fit in your pocket and had an interface that anybody could just use and that the input was just poking at it with your finger and it was all visual and it had wireless connection to a network that connected to the entire world.

It was so science fiction from the perspective of 1978, 79, but within 30 years, that's where everything in those 30 years was heading. So when it launched, it was really the culmination of what we've called personal computers for 30 years, whereas Vision Pro is sort of like, let's do something all new and we have to sort of start from scratch. It's going to be way too expensive and heavy and limited and the battery's going to be a pain in the ass, but it's a totally new vector.

David Barnard:

Yeah, well, we've kind of gotten ahead of ourselves. I want to go all the way back to the eighties again. It's important to step through the history of these developer relations of what brought us even to the iPhone. So I'll speed through this. You and I could talk for five hours, but I don't think we should turn this into a five-hour podcast, so I'll speed through a little bit of this. But going all the way back to the eighties, PageMaker was a huge turning point. Third party app, some people have credited it as saving the Mac platform. That it was so important to digital publishing and this is where as a platform apps can revolutionize your platform. When you've built a and hardware and third party developers go nuts on it, they build new things and do things that you would've never done as a first party software closed ecosystem, it's only Apple and the Mac and we're the only ones building for it.

You get this entire ecosystem of people building new things and PageMaker was one of those things that became so integral to the digital publishing world that it's credited as a third party app for saving the whole Apple Mac platform and then you get Illustrator for Mac in 87, you get Photoshop in 1990 and during this time I think Apple really recognizes that power of developers. Guy Kawasaki joined around that time. I forget exactly, I think he may have joined before the 1984 Mac, but he was the first software evangelist and developer evangelist. Again, in doing research for this and reading up on some of the history of this, I realized just how much a debt of gratitude in some ways I owe to Guy Kawasaki for me having a job today at Revenue is that he... This whole developer advocacy and people who aren't technical or... I mean, I'm mildly technical but really can promote these platforms. It goes all the way back to the eighties and Guy Kawasaki and Apple being so enthusiastic for third party developers.

John Gruber:

I know Guy a little, I feel like I should know him better. I feel like he sort of left this racket right around the time that I was becoming more prominent in this industry, but I've met him a few times, but I've read his books and the Macintosh Way, it's a great book if you can find a copy of it. When I joined Barebone Software, I worked at Bare Bones, the BB edit company from 2000 to 2002. It was the only mandatory reading before.

It was like the entire employee onboarding process was you have to read Guy Kawasaki's the Macintosh Way, but arguably it was the Apple way and at the time though, because it was the only successful platform Apple had, the Macintosh and Apple were easily conflated, but I think that what Guy Kawasaki really crystallized was the intersection of developers, users, and the platform maker and that combined the three could form a cohesive whole that everything... And formed a flywheel where it just kept benefiting everybody where users are happy and they're buying the devices, which helps the platform maker and that the more devices the platform maker makes, the bigger the market is for third party developers.

And so third party developers make more and invest more in the platform and make more innovative software that makes users like, oh my God, look what PageMaker can do. Holy crap. And then the users buy more of the... And it just keeps going and going.

David Barnard:

Sounds a lot like the iPhone.

John Gruber:

Yeah, I think that the other thing that Guy Kawasaki really crystallized was the idea that you could be an important serious player professionally in this field without being a programmer or a designer even. You could be a professional user. I'm a writer and I have a computer science degree from college from long ago, so more technical than most users, but I get that mindset where kind of what I wanted to be was a professional user, by being an enthusiast and learning how everything works. And that was his evangelism. It wasn't evangelism in the sense of evangelizing a religion based on faith. It was more like a religion based on practical advantages, like hey, learn how to do these things, learn how the actual system works and you're going to have superpowers compared to people who do the same thing as you who don't understand how these computers work. One person can do the work of 10 people with a Macintosh, and it was true.

David Barnard:

I saw that guy has been doing the rounds on podcasts. You should definitely have them on your podcast at some point. That'd be one I would love to listen to, you and Guy talking through this for two hours. We're kind of breezing over it in five minutes here, but I think it would be a fascinating listen for you and Guy to kind of talk through that in more detail. But we did want to keep moving. So that was the kind of eighties and into the early nineties. But then what happened in the nineties I think is kind of pivotal to Apple's relationship with developers is that in the nineties, and you know this better than I, so you can fill in the details here, but hardware sales started to tank. Things started to get really rocky for Apple and they got to this point where third-party developers had so much power over Apple that if Adobe wasn't updating their apps on the Mac platform and simultaneously the Windows platform had taken off at that point where they were probably, I assume making way more money on the Windows platform.

It was kind of the platform to be on during that time, but Apple desperately needed those third-party developers to continue building for the platform to keep the platform sustainable. And that all kind of culminated in 1997 with the famous Steve Jobs standing in an auditorium with a giant screen of Bill Gates behind him and Microsoft saving Apple. And again, people who haven't studied the history or been around or not old men like you and I couldn't even fathom that Microsoft saved Apple. Had Microsoft not done that, Apple would've gone bankrupt. So fill in some of the gaps there. What happened in the nineties and how did Apple get into this desperate point where third-party developers had so much power over them needing Microsoft to save the company.

John Gruber:

I think point one that gets overlooked a lot in the years where Jobs was exiled from Apple, who knows what would've happened. Maybe that was for the best that he went and founded... It worked out well for him to go found Next, struggle to make next a thing and then have Next in Apple. I always call it a reunification rather than an acquisition because it really is so obvious. I mean, Craig Federighi's first job out of college was at Next and it's like he left for a while, right? Scott Forstall, but where Apple got lost in those years, one of the ways, and I think I haven't seen a lot of people or a lot of books focus on it, was the sort of mindset in the early PC years, a company would come out with a new computer and the computer was the platform effectively, and there wasn't really this idea, there wasn't so much of you'd make the Commodore 64 and then when Commodore came out with the Commodore 128, I forget if you could run Commodore 64 programs, but it was sort of a new computer.

It was like, ah, this is a different computer. And then Commodore came out with Amiga is sort of an overlooked thing in history and I know the panic guys were big Amiga fans and the Amiga had the video toaster was doing digital video editing way before any other computer platform. It had some amazing capabilities, but Commodore just exemplifies it. Commodore 64 was a hit, then the 128 not so much of a hit, then the Amiga, which was way more capable. But that every couple of years the idea was there'd be like a new thing and backwards compatibility was like a maybe and it would be like a mode, but basically you'd sort of come out with an all new thing every couple years as opposed to evolving a platform over decades. It just didn't enter Apple's mind.

And so Apple had all of these failed next generation, what's going to come after the Macintosh things in the late eighties and especially the early nineties, Pink and Taligent, and it's all confusing and it would take forever to explain as opposed to what was an operating system and what was a company and what was a cross-platform like?

Taligent was sort of a cross company thing with IBM where it was in addition to an operating system, they'd make a new platform and the power PC chip architecture sort of came out of that. And so it wasn't totally futile, but the idea wasn't to how do we keep evolving the Macintosh? It was what comes after the Macintosh. That's the fundamental flaw. And the Newton is laughed at in some ways and other ways people are like, oh man, they're sort of a decade ahead of in terms of you'd have a handheld thing in your hand with a touchscreen, but the most obvious problem with the Newton was that something handheld that needs ubiquitous wireless networking. And there wasn't even Wi-Fi at the time, let alone cellular. Palm Pilot was sort of more of a hit, but mostly because it was affordable. And people like me, I had one, I had a handspring visor and I liked it.

In hindsight, there's a lot of younger people who probably vaguely have heard of Palm Pilots, but it wasn't that big a deal. At the time, people are like, oh, the Palm Pilot is what Apple should have made with the Newton. No, because even the Palm Pilot really wasn't that big of a hit and it didn't have any staying power because it didn't do networking, it didn't have a connection to the internet, even Wi-Fi, let alone cellular. That's really what a handheld needed. But the other thing about the Newton that was just as important to its failure was it really hardly related to the Macintosh at all. There was a Newton, I forget what it's called, Newton Sink Utility or something, and you connect a serial cable to your Mac and Newton, you could sync some things, but like I said earlier, there was no contact app on the Mac from Apple.

So where did your Newton contacts go? The Newton had a contacts app because it was a personal digital assistant and they had all of these things about what comes after the Macintosh when what they should have clearly been thinking of is how do we move the Macintosh forward? And meanwhile, while Apple's core interest and at the top level of the company was interested on these big expensive, all-failed next generation, what comes after the Macintosh? There were people at Apple who were grinding away on the Macintosh, putting out system seven and then system 7.1, system 7.5 and sort of keeping the company alive financially because that's an actual platform that people were using and buying. And I think at the highest level, Apple was looking at that the way that the Macintosh part of the company was looking at the Apple II in the eighties. And for most of those mid to late eighties, Apple was staying alive financially through Apple II sales, not Macintosh sales.

And they were thinking, that's what the Macintosh is doing now and we will get pink or Copeland or whatever this thing is. Copeland was a next generation Mac. That was where they started to get it through their head that, oh, what we really need to do is keep the Mac alive and come up with something. They just wasted half a decade of great still explosive new stuff coming out. The whole internet thing happened in the midst of that where there was no internet to speak of. I mean, the internet existed, but it was like a university type thing in 1991 and by 1993, 4, 5, it was like, oh, Netscape is a huge thing. Meanwhile, Microsoft was doing the opposite with Windows where they're like Windows One, nobody used, nobody even heard of Windows Two, nobody used, nobody heard of. Windows Three, now people are using it instead of DOS, but it was really clunky and awful and they're like, let's make a better one.

Let's make one that steals interface ideas from Next where the buttons and stuff look 3D and have gray scale. And they were grinding away on making the thing that was sort of a hit just a little better every couple years. And Apple just lost half a decade in that period. And thankfully they had people who were incrementally making the Macintosh better, but then they'd sort of painted themselves in a corner where the Macintosh operating system, not to get too super nerdy, but was still fundamentally based on some assumptions from the mid-eighties about how low level all software worked and the idea of preemptive multitasking where a program crashing couldn't possibly crash the whole computer because it would just be the program. Whereas the Macintosh was so low level and all programs sort of made some low level assumptions where they were, there was no kernel to speak of in computer science terms in that classic macOS.

And they were doing things with low level memory where like, hey, if Internet Explorer froze up, your whole computer might just freeze. And then you had to literally use the power button on the hardware to restart it and anything you had open that wasn't saved was gone. In 1984, 85, 86, that's the way a computer like the Macintosh had to work. There was no option to do preemptive multitasking and have memory safe applications in that era because of the constraints of the hardware. But by 1995, 96, that was totally possible and it was obviously the way it should be, but there was no simple way to just say that's how the next version of macOS is going to work. And all of the existing apps like Photoshop and Excel and Microsoft Word will just work. There was no way. It was too incompatible.

And that's what you were talking about earlier where Apple was up against it because the only reason the Macintosh was thriving was because of these apps from companies... And the big ones were Adobe and Microsoft, and if their existing apps didn't continue to work, there was no way anybody was going to upgrade to whatever they came up with no matter what its technical capabilities.

David Barnard:

And so then being back against the wall and Jobs having gone off to Next and built that next iteration, the Next revolution in computing the foundation for everything we do today was what Jobs built at Next, they acquired Next in 96 and Jobs comes back and then that's what leads up to this Microsoft committing to the platform, investing money into Apple. And then I wanted to read a quote, and this is going to be long, and those of you who really care can go back and watch. There's a video of this is that at WWDC in 1997. There's a quote from Jobs. A developer asked about OpenDoc, so I [inaudible 00:55:54] all this, but we can skip over the details of it because I think the details are less important, but Apple decided to kill this technology, OpenDoc and the developer very frustrated, goes up to the mic at WWDC during an open mic session with Steve Jobs at WWDC in 97.

Very frustrated, why are you killing this thing? We've invested a lot of money into it and I want to read the quote. I kind of jump around in the quote because it would take 10 minutes to read, but let me read this quote from Steve Jobs because I think it's just so fascinating.

"I know some of you spent a lot of time working on stuff that we put a bullet in the head of, I apologize, I feel your pain." I wanted to get that in there because can you imagine Apple in 2025 saying, I apologize, I feel your pain and just the rest of this is so good.

John Gruber:

I can imagine it, but it would be very surprising and I feel like that's exactly what they could use, but yes.

David Barnard:

Yeah, that's what we're going to get to and that's why I wanted these quotes. We'll come back to it maybe an hour from now when we get deeper into the iPhone stuff. So continuing, it's skipping around the quote, but "focusing is about saying no. Focusing is about saying no and you've got to say no, no, no. And when you say no, you off people. So you take your lumps and Apple has been taking their share of lumps for the past six months in a very unfair way, and it's been taking them like an adult, and I'm proud of that." Man, Steve Jobs off the cuff. I miss that. I miss that so much. "And the result of that focus is going to be some really great products where the total is much greater than the sum of the parts." So again, that's missing a lot of context.

It's missing a lot of the actual quote. You can go back and watch the video. I'll put it in the show notes, but I just thought that was so fascinating that Apple in '97 was at this point that Steve Jobs of all people was there on stage answering this kind of question with a level of kind of humility and self-awareness that, "Hey, developers are so important. I feel your pain. I'm sorry, I apologize. But then also clearly talking to the future of like, hey, this is going to be hard, but we're building towards something."

And they included that quote specifically from what you were alluding to is that in this forty-year history with developers, there have been moments like that where you see a more open Apple, a more contrite Apple, and that the success of the iPhone has really changed the way I feel like Apple does relate to developers and Apple has not had to take its lumps in a good 20 or 30 years and has not had that level of forthrightness and humility with developers when things do go sideways, and this is where I think Ben Thompson has said multiple times on different podcasts and articles he's written, I think some people inside Apple view this and maybe those three top execs who've been there this whole time and a lot of people inside Apple, it felt humiliating, not humble.

And that this was a period in their history that they were so beholden to third-party developers and they never wanted to be in that position again. They never wanted to have to take lumps again. They never wanted to be on that verge of bankruptcy. They never wanted to feel that pain and be humiliated like that again versus I go back and I read this, I'm like, wow, what a great example of just how much goodwill do you instill in developers in the entire ecosystem by speaking like that to developers?

John Gruber:

The first thing I'll say to that is that of those three executives you've mentioned, Eddie Kew, Jaws, and Schiller. Schiller's the exception where Schiller, I know you probably know this, actually hasn't been in Apple continuously since 1987 or whatever, and in the early nineties he was, I forget where else, but he ended up at Macromedia, which was the company behind PageMaker, or maybe not... No, I forget, but they had... They were the competitor to Adobe, and so Schiller has been on the other side of that divide making the essential tools for the Mac. That just helps add to that same perspective though of knowing how much leverage those companies had over Apple. And the two things that were scarring to Apple were the near bankruptcy. And so it's made the company institutionally incredibly frugal and more so while Jaws was still alive, it was only after Jaws died and Cook took over that they started doing things like shareholder buybacks and stuff while Jaws was alive.

They were just hoarding their profits. They just were putting it into that Braeburn Capital subsidiary and just sitting on an ever-growing mountain of cash because in the same way that my grandparents who had been through the Great Depression would eat, scrape every single bit of food off their plate and thought it was offensive, no matter whether you thought it tasted good or whether you were still hungry, it was offensive not to eat every bit of food offered to you because they remembered not having enough food and the parts of the company that remembered being on the verge of bankruptcy, in some ways it helps focus the company, but in some ways in the long run sort of hurt them. And I think having somebody new like Tim Cook, again, he's been there a long time, but he wasn't there for the near bankruptcy part or came in just after, and so he wasn't as scarred by it.

But I think that developer relations part definitely has, now that Apple has gotten big, has hurt them. That they're still so thinking of themselves as underdogs who want to assert not dominance over developers from their perspective, but having at least 51% of the power over developers that they've lost the fact that they've actually got 95% of the power or however you want to assign the power dynamic in the current state. They're so hell-bent on making sure they never fall below 51% of the power between the platform and the developers that they've just lost sight of how overwhelmingly they've already won and how much it would be in their interest to make concessions because of the surplus of power that they have to bolster developer goodwill. I don't think we're putting them on a hypothetical psychiatrist couch, but they do remember it. It's infused their thinking about the company.

David Barnard:

And we will put a pin in that to come back to as we talk about the more modern era of lawsuits and regulation and everything else like that, but stepping back and walking through the history, you do see a different apple after that. And so Apple does go on to build keynote and pages and numbers and the whole digital hub and they start building more and more of those key pieces of software. I think in part from that scarred time of we want to make sure there's great software for the average user and we're going to bundle it even though that's in conflict with our third party developers. We're going to give things away free or cheap, and you see a different Apple in that early 2000 era of like, we're going to control our destiny. Third party developers are important. We're going to be a platform.

We're going to encourage them, but we're going to cover our own bases. We're going to make sure that we're not beholden to these companies in the long run by doing these things. And then kind of the next era as I was going through all of this, and this is where I kind of step into it, is what I was calling the Delicious Era. And there were these at the time, going all the way back to the eighties, kind of smaller passionate developers, but I feel like the heyday of this passionate small developer time was those early 2000s. You had Delicious Monster Building, Delicious Library and Panic and the Omni Group and Rogue Amoeba, and you could probably... Bare Bones, you could probably list another 20 off the top of your head, and there was this kind of renaissance. The iPod started driving more and more people from Windows to the Mac.

There were these really passionate kind of fanboy developers building these really cool software for the platform. And as a platform, I feel like there was a bit of a heyday during that time where Apple was kind of... And Sherlocking famously came out of the Watson Sherlock thing in, I think, that was 2020, but there was this kind of heyday leading up to the iPhone of really great independent software creators while at the same time Microsoft and Adobe and others were starting to invest more back into the platform and the Mac becomes this really solid platform in that era.

John Gruber:

It's a tough thing to strike a balance on. It's almost impossible to just get perfectly right where it's clearly correct for there to be a suite of fundamental apps out of the box in a factory fresh new computer or phone or tablet. And that therefore that 1990 to 1995 Apple mindset of we're hardly going to ship any first party apps and everything will be third party apps because we don't want to step on their toes. And even if we have a subsidiary that makes Mac Write and Mac Draw and stuff like that, or File Maker, we're going to put it in a subsidiary and try to treat it as best we can as an actual third party developer, even though we own the company. That's not the right way to deal with a platform, but obviously Sherlocking every successful app is also not the right mindset.

It's a hard balance to strike, and I think they've managed it pretty well, especially... And again, in the early 2000s when Sherlocking first became a term, it was so few years since the era when Apple studiously avoided ever stepping on the toes of third party developers, that it felt like all of this was newly offensive. And here in 2025, that's sort of ancient history. And so people don't think of it that way. So for example, just this month at WWDC, they announced clipboard history management in Sherlock on macOS Tahoe and a sort of more launch bar, Alfred Ray cast style superpowers in Spotlight where you can assign a two letter abbreviation to something to launch a shortcut or something like that. I think that they continue to strike the right balance where I, as a long time launch bar user, I'm glad they're adding those features to Spotlight, but there's 0% chance that I'm switching to Spotlight.

I have an example though where here's a market where I feel like they tried to stay away from third parties and I think it bit them and now they're entering late, which is password management. And OnePassword is a great app from a great company that used to make a really great Mac app for passwords, and they're still a good company and the app is still fine. I've never been a user of it, but I see why people are. But the dynamic is the more popular and successful OnePassword came, the more that grew and they grew in interest to want to reach the enterprise market. And that changed the product in a way that made it not so great as a Apple product, an Apple platform product.

OnePassword is still a great product, super good at a technical level, super useful in that enterprise context and in terms of some of the family sharing and stuff like that. But it's like if you really want the Mac style interface for password integration and the iPhone style integration and the syncing between the two, it started becoming not as great as it used to be because their interest in growing their market, which is great for the company, were in conflict with making it perfect for the Apple platforms. And so Apple came out with Apple passwords I think last year. I think it's only been a year, maybe it's two years.

David Barnard:

I don't know. It's been... Well, I mean, the password app, but they've been kind slow rolling into building the password app.

John Gruber:

It was effectively an app worth more than an app, a serious app worth of capabilities and features, but hidden away in a system settings panel for years, I think out of deference to we don't want to squash this market. But then I think as the market sort of moved into a less and less idiomatic Apple platform style of software, they were like, you know what? We should just make our own app because we could do this in a way that's very Apple-y. And I think now the new passwords app, it's a good introduction to how do you make a modern app for Apple platforms? Any area where they try to stay out of, eventually they find themselves having to enter.

David Barnard:

Yeah, so this is a huge can of worms that we could spend an hour talking about the balance of Apple, what they ship and what they don't, and what developers' toes they step on and what they don't. Maybe this is a whole nother podcast, but I want to step back and-

David Barnard:

Maybe this is a whole another podcast. I wanted to step back and see if there was anything else you wanted to share relating to the 2000s in that. I feel like that era did actually set Apple up really well for the iPhone as a platform. The Cocoa frameworks, the passionate developer base, the books that were written. When I started working on iOS, I intended to be the programmer and do it all myself. And so I bought the famous book of the era, Aaron Hillegass, Cocoa frameworks or whatever it was. And so by the time you got to the iPhone, there was this really solid, passionate community. Books being written, conferences being attended. WWDC had grown tremendously, and this era of the 2000s of the Mac becoming this really great platform was a springboard that then propelled the iPhone even faster as a platform than I think it would've otherwise been. Is there anything else you wanted to talk about that era before we jump into the iPhone era?

John Gruber:

The basic mindset in the late '90s in the industry was a sort of consensus that user interface design doesn't matter that much. Nobody would argue it doesn't matter at all, but that Apple's focus on making it the top priority of their platforms wasn't worth it because, okay, let's just concede that the Mac was a better user interface than Windows. Look at their market share. Obviously it didn't matter. It wasn't an unreasonable conclusion, but I think it was wrong-headed because I think that the problem that people arguing that way didn't see yet was that no computer. Again, it comes back to that argument that the iPhone is truly the first real personal computer, the one that every person would want and would care about.

At the time, even in the late '90s, too many people making decisions about what computers to buy or what computers a company should buy weren't the people who care that much about user interface and therefore they were buying Windows PCs based on other criteria. Those early 2000s that built up this skill set in designers and developers and built up these teams of either companies or independents or just hobbyists, but at every level who could make software that was like, oh man, just look at it. Remember the Disco app. It was a DVD burning utility. When it burned the DVD, it actually had smoke come out of the window. Some people were like, well, that's just a complete waste of CPU and GPU resources, and other people were like, where do I buy this? I want to buy this because when I burn a CD or DVD, I want smoke to come out of the window because that's just cool and fun.

This whole skill set was there for Apple and in 2008 when the app store opened up to build apps that people would just be like, but just look at it. Just look at this. Oh yeah, where do I get that app? I want to get it. It fueled this consumer fervor for the platform that no other platform could even hope to compete with at the time. There was no other platform. Early Android, they just couldn't do it. Microsoft's mobile, Blackberry, whatever. Nobody had the skill set. It was impossible to make anything that was like, just look at it. Just look at this app. Look how cool it looks.

David Barnard:

Yeah. I hadn't thought about it from that. The design perspective as well. I mean, that's what brought me to iPhone development. We'll move into the iPhone era now, is that I was that uber passionate Apple fanboy, Mac nerd. I had my, I don't even know what it was at the time, in 2007, some PowerBook that I had at the time. I loved the software, I loved the platform. I was first person, not first person in line. Well, I was first person in line to buy an iPhone. I was in line. Again, if you weren't around and weren't a fanboy at the time, it's laughable to think about this at the time, but I stood in line for, I think it was my iOS, Mac OS Tiger or one of those. There would be lines at the Apple Store and OS Update was a launch event.

John Gruber:

You had to pay $129 for it.

David Barnard:

Yes. You would line up to pay $120 to upgrade your operating system. It was that passion about the platform at that time that you had people like me and millions of us around the country who cared so deeply about the platform for all of these reasons is that it wasn't just good hardware, it wasn't just the OS, but it was this combination of OS and fun software and delightful, but it was productive. In 2003, I actually bought that 17 inch PowerBook because I was using Photoshop to manipulate this aerial photography for my dad's commercial real estate business. The Windows laptop I was on kept crashing. I was like, dad, I got to get a Mac if you want me to keep working on this stuff. Went and paid for it. The experience was night and day working on Photoshop on a 17-inch PowerBook than it was whatever crappy Windows machine I was using at the time.

And so there was this fervor for the platform in that time that I think was the perfect setup. And also coming into the iPhone, there was enough of that groundswell of people like me. I was in China when Apple announced the iPhone. I went to the internet cafe at a Beijing hotel to watch a live blog of the Macworld keynote that you were at when they announced the original iPhone because there was just that level of fervor. And then six months later, my brother and I go get in line to buy the first iPhone. There was that passion, and then by the time they announced the SDK that next year, I jumped into it because I thought this is going to be something. I saw something different about the platform, and so much of that had been built up through Apple's experience across the decades building platforms of the turnaround of the Mac, of building the foundations with Cocoa and stuff like that. That ended up becoming the iPhone. And then by the time the iPhone App Store was released, there was this groundswell of developers who were just so excited about the platform.

They could not build an app for this platform. It wasn't just original Mac developers. That was one of the fascinating things, you alluded to it earlier, is that a lot of the Mac developers didn't really do well on the iPhone because they were maybe a little too caught up in what they had built for the Mac. What we saw happen when the App Store launched with so many new companies being built, new ideas being explored, and just this fervor for building for the platform.

John Gruber:

There was a skill set that transferred immediately where somebody who is really fluent as a developer in Objective-C and the AppKit APIs on the Mac could immediately jump over, because it was just more limited. It was like AppKit but a lot more limited. But in terms of the syntax and the style of the APIs, they could just jump right in and thrive in a way that a developer who's familiar with Java at the time, which was super popular, or the Windows C++ APIs was like, what the hell's going on here with all the square brackets? But in terms of the concepts for what an app should be and do in the scope of it, it wasn't a mini Mac. It still isn't, but especially in 2008, 2009, it just was so much more limited and the context of where and how people would use it was so different that it just at a conceptual level be thinking in a very different way, not quite as profound.

But along the lines of the difference between the purely command line interfaces of the early PC era where you just had text on a screen versus a graphical user interface. It was the same difference where it was like, hey, people are just going to sometimes open your app and want to use it like tap, tap done and get out. You could have Mac apps at the time where you'd launch the app and it would show a splash screen. It was a whole term of art like, Photoshop and Adobe apps famously would take 30, 40 seconds to launch because they were such big apps. Well, that made no sense on the iPhone. If you had that mindset like, I have this idea for an app, but it's going to take 20 seconds to launch, well, people would just be like, nah, screw this. I'm hitting the home button and deleting the app before it finished launching.

David Barnard:

To bring back the developer relations thread, WWDC 2008, which you were at, one of my big regrets in life is not going to WWDC 2008 because I founded my company April of that year to build iPhone apps. I had borrowed money from my family. I felt this tension of am I spending my family's hard-earned money that they've invested in me to go on a vacation to San Francisco to this developer conference? And so I did not go. What I heard in retrospect was that they were actually signing up developer accounts in person at WWDC that year. Could have been there day one had I gone, but this was the first time WWDC ever sold out. I've heard stories about past WWDC. They would be giving away tickets. They would be begging developers to come, and at WWDC 2008 was the first time it sold out.

And then from then on, that groundswell of developer and the platform becoming so powerful, they never again had to ask developers to come. It was sold out every year after that, eventually having to go to a lottery. And then there's one more point I wanted to make was that at WWDC 2008, the slides from the presentations had the email addresses of Apple evangelists on the slide because they're like, hey, email us. We need more feedback. We want to know what's going on. Even as successful as the Mac platform had become, this was still pre iPhone Apple and pre the iPhone platform becoming what it became was such a different Apple. Funny story, because I had not gotten a developer account, I sent an email to five of the people-

John Gruber:

On the slides.

David Barnard:

On the slides. John Galenzi of all people responded to the email, gave me a phone call. I mean, to this day I remember he actually just retired from Apple. I had a lovely chat with him a couple of weeks ago at WWDC on the side because he's no longer at Apple anymore.

John Gruber:

No, he's no longer at Apple, but I saw him at WWDC.

David Barnard:

Yeah. Such an incredible human. But evangelists would put their email on the slides. It's just hard in 2025 how secretive, how close, how we choose you, you don't choose us. How hard it is to get the attention of Apple for the average developer. That was the era before the iPhone platform became so big.

John Gruber:

It was clearly a surprise to Apple. The whole idea that jobs had to be talked into opening up an API. I think that's overstated a little to some degree. I was going to say how much of that was just him blustering? Well, the difference is between should there be third-party apps for iPhone versus should the iPod support Windows. Now, Jobs wholeheartedly was against supporting Windows. He really was 100% on board with the iPod as a thing to help sell the Mac. Making it a Mac-only peripheral was in Apple's interest because it would bolster the Mac and every other executive from Schiller to whoever else was like, we're holding back the iPod as a platform by not supporting Windows.

There's multiple books that he have written about it where he's like, all right, fine, go do it, but don't bother me. I don't want to know about it. And then he called it the iTunes for Windows, the Glass of ice water in hell. He was happy once it came out and he could see it and he could say that, he was happy, but he was really against it. I don't think he was against opening the iPhone, I just think he thought someday. I do think that maybe it happened a little faster than he thought. I don't think he anticipated announcing it in 2007. In fact, at 2007, WWDC was when they announced their "sweet solution" for third party developers, which was a very small JavaScript library where you could make some web apps that looked like native iPhone apps. They wouldn't have announced that in June on the cusp of the iPhone going on sale if they really thought, hey, we're going to have a native SDK early next year.

It was September, October where they just made an announcement like, sure, all right, fine. We heard you. We're going to open an SDK. Give us a couple of months to get it together. We'll get back to you when it's ready. I think he thought it was like, we'll get to it in a couple of years, but I think it already was proving more popular and more resonant than he thought. I think Jobs and everybody at Apple knew this iPhone was a hit. They knew it was a thing. They weren't surprised that it was in sensation when they announced it, but it was even more resonant and more of a hit and bled out to more normal people. The iPhone first came out in 2007, right away in the summer of 2007, I'd be at Whole Foods and I'd have a shopping list in a Web App and Randos would just come up to me and be like, is that an iPhone? Is that an iPhone. All the time. I don't think Apple was anticipating that level of broad consumer appeal and it accelerated that.

The WWDC thing is a perfect example. Before the iPhone, they had a whole extra track at WWDC. They called it the IT Track for IT professionals who managed Mac installations in corporate environments. It was because they had room, I don't know, I'm just ball parking, 3000 developers, but then 2000 IT professionals and a whole different track of sessions where instead of talking about APIs for making Mac Apps, it was sessions related to the very serious, a reasonable topic for a conference, but it was almost like two conferences in one. One for developers and one for IT professionals, just because they wanted to fill up Moscone and they had room. With the iPhone, it was like, oh, we got to get rid of that. There was this whole resentment because, it was I think a very good and successful and popular conference for IT professionals, but when the popularity of the iPhone happened, it was like, oh, they got to go. And then it became, even Mac developers felt like, hey, this used to be all about the Mac and now it's session after session after session is just about the iPhone.

David Barnard:

We've talked about a lot of things that are ultimately almost a fluke of history that things played out the way they did from Bill Gates saving Apple and all those things. I can't help but think. I wish I could remember their names to give them credit for it, but very soon after the iPhone was released, the developers jailbroke the iPhone and started writing native apps for it. Craig Hockenberry is one name I will call out. I wonder if that jailbreak scene and seeing what developers were building under insane constraints. Because when you jailbroke, Apple hadn't documented APIs. It wasn't a real SDK. Developers were having to reverse engineer methods they could call and how things were working. I can't help but think that some of jobs changing his mind so quickly was because of how innovative and how passionate that base was.

I mean, I ended up buying it. When I started my company, I bought a second iPhone because I was too nervous to jailbreak my own iPhone. I bought a second iPhone, jailbroke it and installed all these apps for me as a way to study what apps could do. It's like you could study as a developer in 2008 before the App Store was launched and you had 500 apps to poke around to see what people were doing. I jailbroke a phone specifically to understand what could be done and what people were doing and what was going on with the platform. I can't help but think that Hockenberry and Steve Troughton-Smith and some of those other early jailbreak folks had an influence on the SDK actually coming out as quickly as it did.

John Gruber:

Yeah. I think Jobs appreciated that. Lucas Newman, who was at the Luscious library at the time and then went to Apple. I think it got him hired by Apple. I haven't heard from him in a while. I also know that, I think this is a public story, but Lucas Newman wrote the first game. It was called Lights Off, wholly backwards engineered, entirely. Hockenberry came out with a version of Twitterrific that was a native app before the year was out without any SDK from Apple, but building apps for the iPhone through Xcode. Just bananas to me that this happened. But I think Jobs appreciated that mindset because of all the crazy nonsense him and Woz had done back in the day before they founded was. Before they founded Apple making the little blue boxes that would let you make free long-distance calls on a payphone and stuff. The enthusiasm was just so much stronger where it was like they'd be crazy not to hold it back.

David Barnard:

Then March 6th, 2008 a date seared into my memory, they announced the iPhone SDK. This is again where I think people in 2025 don't appreciate what a different era that was in terms of what was possible as a developer to build a business. I wrote a business investment thesis that I sent to my dad and mom and uncle who ultimately invested in the company. I specifically wrote in there, what an incredible deal this is that I don't have to host my own store. Because back then, I mean, again, so easy to forget in this era of Stripe and AWS back ends and everything like that, that standing up your own web server to distribute apps, especially if it's a larger app, could get very expensive. Bandwidth was expensive. Working with third-party, payment platforms was a hassle. You needed a whole team to sort all that stuff out. And so when Apple announced the iPhone-

John Gruber:

Especially on a phone, right?

David Barnard:

Yeah.

John Gruber:

Credit card would be even harder. There was no way to scan it, no tap to pay.

David Barnard:

The only software that was on phones at the time was carrier build. You had to do a deal with a carrier and they took 50% of everything. The App Store was genuinely a revolution in software of a revolution of opportunity for developer. I mean, this is what I built my career on. This is why I have such a soft place in my heart and I'm so obsessed to this day with the App Store because it just fundamentally changed the opportunity you had as a developer to build a business. Of course that's not true anymore in 2025 with Stripe and hosted Back ends and Bandwidth being essentially free and all these third-party SaaS tools that you could spin up a Web App. I mean, geez, now even in Vibe coding where you don't even need a backend or hardly any experience to spin up a Web App that's just hosted on Replit. You can charge for it via built-in payment solutions.

It's just crazy how much different the world is today than it was for that original App Store release. I think people today forget just how powerful that was. We were talking about this before we hit record trying to do the math. There are kids today, teenagers releasing apps on the App Store whose parents probably weren't even alive when Schiller and Cue and Joswiak joined Apple in the '80s. You could be a 16-year-old developer with a 40-year-old parent who wasn't even alive when all of this started with the Macintosh in 1984, much less 1976 when Apple was founded. I think there is a little bit of a loss of history and then maybe at Apple a little too much recognition of history of here we are in 2025 and the world has completely changed. The iPhone helped change the world 17 years ago, but now it's been 17 years since the world changed.

People today looking from the outside without this history, I don't think appreciate the things that Apple appreciates. They don't have the context and the history. I think when you're trying to understand how Apple operates, why they're so insistent on the App Store fees and other things like that, you have to ignore all of that history, which to people's credit they don't even know. That's why we're doing this podcast. To understand Apple, you have to go back those 40 years and see all of what it took to get to the iPhone and then the iPhone becoming the platform it is and the billions and trillions of dollars that the platform has generated for third-party developers, that's hard not to just appreciate.

John Gruber:

To some extent at this point, it's becoming clear that Apple itself has fallen into the same trap. I'll exemplify it with a quote. I've been thinking about this a lot. I'm hopefully going to soon turn it into some article on Daring Fireball. There's a Steve Jobs quote. It's actually, Apple's made a big plaque of it, huge. It's, I don't know, 10 feet diagonal. It hangs not at Apple Park, but outside the Town Hall Theatre at the old Infinite Loop campus. The quote is, if you do something and it turns out pretty good, then you should go do something else wonderful, not dwell on it for too long. Just figure out what's next. I think with the App Store in particular, boy that really resonate. It's not that they should forgo all profit and all commissions from the App Store, the whole, well, we started with 70/30. We should stick with 70/30. We've never raised it from 70/30 even when it's become more powerful or more monopoly, whatever you want to call it.

David Barnard:

As they've increased in control and the platform has increased in importance, they could have increased and squeezed and other things.

John Gruber:

Right. The people at Apple who are insisting on keeping as much of the commission's and the rules and everything as they have, but especially when it comes to payments and letting people link out to the web and stuff like that. They're thinking, hey, we built this thing that was so much more generous and developer friendly than everything that came before it on handhelds or, especially on phones. That they're still caught up in thinking of what it was in 2008 as opposed to that Jobs's quote, if you build something and it turns out pretty good, then you should go do something else wonderful, not dwell on it for too long. I feel like Apple is dwelling on the success and the innovation, true innovation, profound innovation that absolutely shook up and completely revolutionized the phone industry more than Apple even revolutionized the PC industry, but they're dwelling on it for too long. That they should move on and build something else new and start conceding on that issue.

I think it is something that they've lost when they lost Steve Jobs. People think that they lost the ability to make new things, that it was always his ability to drive them to make a new thing. But I think he was good at, okay, fine. Again, I mentioned that whole iPod for Windows thing where he stuck with it for a year or two and then he was like, okay, fine, fine. At some point the people holding onto all of these rules and healing all these decisions about the anti-steering and stuff. Somebody at the top named Tim Cook should probably just say, okay, fine, fine. Let's just give in on a lot of this. We don't have to worry about it anymore. Just clear it off our concerns. I think it would be so good for Apple to just clear it off the table and just clear their time and their energy and their talent from executives down to engineers to just figure out what's next and make something new that would build into something where they have to worry about this again in 10 or 15 years.

David Barnard:

I want to dig into what I will affectionately call App Store 3.0 because I completely agree, but let's step back one more point in history. I have a bunch of notes. We could go through all of the early iPhone days. It's hard for people who don't even know that there weren't in-app purchases, that you had paid upgrades. That in order to do a paid upgrade, you had to release a whole new app and then transition users to it. There's so many points on the App Store history of just oddities and stubbornness and weird things that Apple did in those early days, even as the platform started taking off. But in 2016, Phil Schiller did a round of interviews. I think the one that most concisely covers it, maybe the one he gave the most access to was Verge.

They titled the article App Store 2.0. And so in hindsight now I will give this way more credit than I think I did at the time of, it really was App Store 2.0. It really did fuel what we see as the current era of the platform. They open up subscriptions to all apps, which obviously working at RevenueCat and now all my apps are subscription. I know some users still bulk at it, but from a developer's perspective and being able to fund the creation of great software and continue working on it, that was revolution. That was App Store 2.0 to empower developers to better monetize apps. They sped up app review significantly. Again, if you weren't around a decade ago, you don't remember the days when it was seven days, 14 days to get an app through App Review. As much as you might complain about App Review today, at least you get that rejection in 24 hours to 48 hours instead of seven to 14 business days. They dropped the commission to 15% on year one renewal.

If you started a subscription, that first commission would be 30, and then after that would be 15%. They announced App Store search ads as a new way to pay to get users. As much as we can complain about name squatting and having to pay to defend your brand, it's an incredible opportunity to be able to pay and get in front of people right there in the App Store. It's actually the paid acquisition channel that I recommend any App Store with. If you're struggling to get downloads, the first thing you should do is start figuring App Store search ads. That was App Store 2.0. They started removing a lot of these old apps that weren't working or just crappy apps. They started to purge the App Store and curate it a little bit more. That was App Store 2.0 in 2016.

Looking back now almost a decade since. It really was a profound shift in the App Store that has led to so much of what we now get to experience as the App Store would not have happened had they not loosened the reins in those ways and made those changes. And so as much as we talk about, I complain on Twitter about Apple being obstinate and not changing and being stuck in the past and everything like that. The App Store 2.0 was them changing. Did they go on an apology tour? Did they, whatever? No. But they made very fundamental changes to the App Store that propelled it for this last decade. To your point, this is what I want to get back to today in 2025, is that it really does feel like we are in need of App Store 3.0, a deeper, more fundamental rethink of the opportunity.

I think to your point, get out of the way. Let developers build. I think the Vision Pro is a good example too of the animosity that has started to build up. The frustrations and everything has gotten to a point where developers are way more wary of Apple. You posted some really great posts this spring, Apple, you're killing my vibe, and then another one by John Siracusa, just about developers seeing Apple more and more as a inconvenience to reaching their users versus a partner in building this incredible platform. The iPhone continues to sell like hotcakes. Apps are making money hand over fist. Developers are building apps, new apps every day. From the outside and looking at the numbers, maybe the platform is fine, but I think this sentiment where developer relations are in 2025 with the lawsuits, with the DMA, with all of the things that are going on, it feels like we're due another reset.

Personally, I would love to that be a little bit more like the '97 jobs of like, hey, we did some things that we thought were right at the time and the forthrightness to say, here's why we think this. Here's why we did it. We're changing our mind. We're going to focus on building these great platforms moving forward. What does Apple need for the next decade and the decade after a vibrant developer community who's going to jump on the next day AI platform. Meta and Google and OpenAI and others are tromping at the bit and have billions of dollars to invest to not let this next platform play out the way the smartphone platform played out with Apple having so much control and so much power, maybe it's time for a bigger change.

John Gruber:

It's just proven so lucrative and forms the backbone of their services, "services that they report financially," which has been their growth vector for the last, I don't know, seven or eight years. Not because interest in the iPhone has decreased, but because clearly the iPhone is literally so popular that every single person in the world who lives somewhere where the iPhone is available and they can afford one and they want one has one. It's that popular that it has peaked because they've run out of people to sell it to. To their credit, it's part of the appeal that they build them to last. That's good for the environment. It's good as just a message that they're durable and the silicon is so good that five, six-year-old iPhones are still very credible devices. I'm running iOS 26 on an iPad from 2018, iPad Pro. It is a little slow. That's a seven-year-old device.

The "services" has been their growth for the last seven or eight years. A lot of that comes not, they would like you to think that it's from Apple services, from people paying for iCloud and paying for Apple TV+ and whatever else they sell as a service. But a lot of it comes from their commission from the App Store, but they could decrease their cut and they could open up instead of fighting for these anti-steering things, especially going to the web stuff, which I've been against for years and years. I mean, pretty much ever since it became an issue that this is ridiculous. Especially like in the Kindle exemplifies it. That if the terms of the App Store are such that the Kindle App cannot sell app or books in the app without losing money on each book, which is the way the e-book publishing industry works, where there's a 70/30 split between the bookseller and the publisher and therefore if there's a 70/30 split between the publisher and the platform, they literally lose money on each sale that they'd owe.

A $10 book, they would owe $3 to Apple, but they would owe $7 to the publisher and therefore at best would make nothing, so why do it? If you can't sell books through the app because of the terms of your store, you should absolutely let them have a button that says, go here to go buy books on the Kindle website. The idea that they fought that is, it's just absurd, and clearly anti-user. It just exemplifies how they've gotten caught up in thinking way too much that the point of the App Store is for Apple to get a commission on all digital content sales for the platform as opposed to what it should be and could be and should remain going forward, which is...

John Gruber:

... could be and should remain going forward which is us maintaining control and having approval over the software and the APIs and what can happen in the background and how things are managed and how privacy is managed in the sandbox and everything is the best for the platform long-term and very much the best interest of the users. It should be that thinking. And then, the fact that we make a lot of money but maybe not as much money for all digital content on the platform because we do have and one of the ways you can do in-app purchases should be icing on the cake, which is clearly how they thought of it at the outset and they should just go back to thinking that.

And I really do think that if and when they do, and I think it's a big if, but... And not at the point of regulation. Because if it's at the point of regulation, we see it. They're just going to make it convoluted and complex and the only way this knot is going to get untied is for Apple to willingly say, "You know what? We're going to lower the rate to 80-20 for everyone and 90-10 for small business," or something like that, "And we're going to just drop... If you want to send people outside the app to the web to make the purchases, just give them a button and they'll go to the web to do it." If they did that, I honestly think they would not see a significant decrease.

And I think we're going to see that proved out in the coming months and quarters as Apple releases their quarterly finance statements after the recent ruling here in the US, their biggest market, that allows stuff like that. I don't think we're going to see a decrease in services revenue, now that they've been forced to open this up. So why not just open it up worldwide and make it easier for everyone and stop hanging the sword of Damocles over everybody that, "Hey, if we win an appeal in a year or two, we're going to revoke this access that you've now gotten at the point of Judge Yvonne Gonzalez Rogers' legal declaration." It's better for the platform. Just make people happy. Make developers happy and users happy and Apple will profit from it. They really will.

David Barnard:

It does seem like dropping the fee would be a huge change in developer relations, in developer sentiment. I would hope they would go all the way down to 85-15 and I think there's Ben Thompson-

John Gruber:

And maybe something different for games maybe because-

David Barnard:

Yeah. That's what I was going to say. Yeah. Maybe games stay at 70-30 because that's what Sony and Nintendo and Steam and everybody else charges. Except for Epic with their App Store, but they obviously have reasons to artificially put that lower. But I can't help but think it would change the tone with the industry more broadly and be more in line with the reality of 2025. Now, you can argue, well, you're not just paying for payment fees. I think that's a disingenuous argument that a lot of people make.

It's like, "Oh, Stripe is 3%. Why should we be paying Apple 30% for payments?" Well, you're not paying Apple 30% for payments and this is the argument Apple continues to make is that it's a platform fee. But there's a couple of things in there. One, it's almost a fluke of history that Jobs, in that original iPhone announcement said, "Hey, if you have a free app, we're going to distribute it for free and it doesn't cost you anything." And at the time, that was great and that created companies like Facebook and Uber and others where they might not have been able to make it work. Well, Facebook is a bad example because they were already reasonably profitable, but the iPhone certainly did springboard them even further.

John Gruber:

Yeah. But I would argue that the company is... It's not just that they adjusted and adapted to mobile. Meta, today, is unrecognizable from the Facebook of 2007. And in hindsight, they were clearly meant for mobile. To the point where they've got products that people use entirely on mobile, right? You can technically use Instagram on the web, but the vast majority of Instagram users have never once used it on the web.

David Barnard:

But would Instagram exist as it is today if they had to pay 50 cents per download or had to pay per user?

John Gruber:

Right, right. It is a quirk that Apple... Because Apple was coming at it from the mindset of the way the Mac worked. That there were free apps, but that any company that wanted to run the business from the app would be selling copies of the app. You'd buy the app before you installed it and that was Apple's mindset. And again, they were selling copies of their operating system at the time. If you bought a Mac that had Mac OS 10.2 installed and wanted to upgrade to 10.3, it cost $129 and it cost 100 some dollars or I don't even know what it cost to get Pages and Numbers and Keynote.

All of that stuff was for sale for what would, today, strike people as bananas amounts of money and that was their thinking of how software would be sold. And I think the idea of a company and... Meta exemplifies it. That a company, like one of the five biggest companies in the world purely making software... Well, I mean I know they have got the glasses and stuff now too. But like Microsoft, primarily a software company, would be making all their money by giving apps away and only having ads in the app? It just didn't compute at the time and they never foresaw that... It's sort of a loophole. And if it costs them 50 cents a download per user per year, they could afford that very easily.

David Barnard:

They could. But then, would Instagram have been created? So many companies who have been built on top of it, could they have done it? But in 2025, when you look at the state of the world of Airbnb making billions of dollars, Uber making billions of dollars, Meta making billions of dollars, Google making billions of dollars on the iOS platform and not having to pay a penny other than $100 a year developer account.

And here I am, indie developer supporting my family. I've paid Apple over a million dollars. I think closing in on $2 million in my 17-year history. Is that fair? And in the world of 2025, that just seems bananas like, "Why have I paid Apple $2 million for my dinky little indie apps and Meta has paid Apple $100 a year for 17 years?" It's bizarre. If you erase 40 years of history, if you erase all the context that we've built up to this point, and you just look at it as a logical person in 2025, that just seems bananas that I am paying so much to Apple and Meta is paying zero.

John Gruber:

I do think that was some of the thinking behind the core technology fee for the EU DMA compliance plan where it was sort of like, "What would we do if we did it all over again?" And I think that 50 cents per user per year fee for million plus download apps only was sort of thinking this is what they would do all over again. But the irony of that is that they're even walking away from that now, because the EU has said that the CTF is not compliant with the DMA. So they're switching to a core technology fee or commission which, again, is only on in-app purchases.

So again, if you have a super popular app like Instagram that you can use without ever making a digital goods transaction through it, Apple makes nothing but the $100 a year developer fee. I do think they are thinking of it and they tried. The CTF was sort of their attempt but it is sort of a tricky position. But I think the answer to that is, "Hey, maybe you should just be happy that you own this platform and not worry about how much money you make from it," and, again, like that Steve Jobs quote. And just make something else wonderful and go on and really refocus on getting developers to say, "If I didn't have to answer to my boss or what I'm telling my boss and manager, I think we should do is put our efforts into making awesome software for these Apple platforms."

To get that developer enthusiasm back I think is worth more to the company than whatever money they're making by breeding pure resentment with the current policy. And I don't want to let it slide, because you mentioned it but I want to emphasize it, that one of those differences between visionOS today and the original Mac in 1984, 1985 at this point based on where we are in visionOS's life, is that even though the Mac wasn't popular in 1985, there was this blossoming ecosystem of Native Mac software, even though the market share wasn't there. Because of the enthusiasm developers had who were like, "Oh my god. People..." It just clicked in their heads like, "This is the computer of the future. I want to make software for it."

And we're not seeing that for Vision. We really aren't. There are cool apps and it's not a dead platform but it's nowhere near... visionOS today is nowhere near as vibrant a third party developer ecosystem as the Mac was in 1985 or 1986. And I think that should be the red flag for Apple and I think they might be a little surprised by that. I don't think they're surprised by the number of Vision Pro headsets they've sold, but I think they are a little disappointed and surprised by the lack of developer enthusiasm for the platform.

And I think it's entirely because developers are so resentful of the way that Apple has treated them, specifically around finance and payments, that sort of thing. We can argue about the rules on background processing and stuff like that in sandboxing and stuff that apps would like to do. But it's really the resentment... First and foremost, numbers one, two, and three on the list of reasons why developer relations are strained with Apple has to do with money. Anybody who says otherwise is wrong. And Apple doesn't need money. Again, they are not operating on narrow profit margins. Their profit margins have gone up, not down.

David Barnard:

This is the tricky point though and this is me listening to too much Ben Thompson, but the tricky thing for Apple at this stage though is that the services revenue is so important to the growth narrative around the stock. That even though they don't need the money, they need the money to continue growing the stock at the pace it's growing. And that's the rock and a hard place that they've gotten themselves into is that the services narrative is so strong and that quarter-over-quarter growth in services revenue and services profit when the hardware has kind of started to flatline a little bit-

John Gruber:

I don't want to interrupt you. But it's like the Exxon Mobil's of the world ran into this problem when they were on top of this market cap lists where it's like, "Well, how many more cars and motorcycles and airplanes consuming fossil fuels could we have, right?" It's like everybody who could have one had one and they're not going to make cars that purposefully consume more fuel. There comes a point where a product or a service or a category really does max out in terms of human population and it's a good place to be. But if your mindset as a Wall Street investor is growth, growth, growth, how much more could they grow, right?

David Barnard:

Yeah. And maybe this is where we need to go back to this Steve quote from 1997 and maybe the message is as much to Wall Street as it is to developers and Apple saying to Wall Street, "We're going to need to take some lumps, potentially like you and I have said, I mean, if they dropped the fee to 15%, would they lose money? Maybe, but maybe Netflix would come back to the App Store.

Maybe... In my job at RevenueCat, I talk to so many developers who are just, "Web, web, web, web, web. We're trying to push as much as we can to the web. We're going to experiment with pushing out of the app into the web now because it's more profitable. We want to save on that 30%." And so, if they drop the fee and it just didn't even make sense to charge on the web. Because at RevenueCat, we did some experiments and Netflix did some experiments with Apple, early in the Epic case, I think it came out that their number was somewhere around that like 12 to 13%. Where if the fee had been dropped that low, it would still be more profitable to operate in the App Store than outside the App Store. And then, there's a lot of complicating factors now too of owning the relationship and would Netflix want Apple to be an intermediary? Well, guess what? If Apple were a more friendly intermediary, maybe they wouldn't mind so much and they would just pick the one that was more profitable on the dollar for dollar basis.

John Gruber:

We know it's a solvable problem because there are more platforms for signing up customers that give the owner of the service, the newsletter, the streaming service, the music service, whatever it is, more direct relationship with their customers. We've seen them built, so Apple could obviously build one into the App Store.

Instead of making all these entitlements over linkouts and stuff like that make it an entitlement where you kind of have to qualify and have these restrictions on, "Well, do you have a customer service department? What's your refund policy? We're going to enforce that you have a customer friendly refund policy where you don't have to call a 1-800 number and listen to somebody try to talk you out of unsubscribing. We're going to test it. That's part of app review, where it has to be as easy to unsubscribe as to subscribe. Otherwise, we will pull your entitlement."

But then, if you qualify on those terms and you have those policies in place, you can have more of a direct relationship with your customers. Do whatever it takes to make developers happy to be building for the Apple platforms. Instead, they're clearly focusing on, how can we extract a decent enough portion of the revenue that's conducted on these platforms?

David Barnard:

Yeah. And so, taking liberties with the Steve Jobs quote from '97, "Apple's going to need to take some lumps in the coming months, but we're going to take it like an adult and I'm proud of that. And the result of that focus, focusing more on developers and building a fantastic platform over extracting as much revenue as we can from that platform, we and third party developers are going to build some really great products where the total is much greater than the sum of the parts." I shitpost on Twitter about Apple all the time and I know a lot of people inside Apple don't like me for some of those posts. But what I care about deeply is this App Store platform-

John Gruber:

Join the club.

David Barnard:

Yeah. You recently. It's that you and I care unreasonably about this platform. On an earlier podcast with Ben Thompson, I love this quote from him, he said, "It just breaks my teenage heart to see Apple continuing down this path that it's going on." And I think that you and I both have gotten to this level of frustration with developer relations and what Apple's doing and the way they're operating. Not because we hate Apple and want to see them fail. And not because we're just take joy in ridiculing them or complaining and criticizing them publicly. It's just that we care so deeply and we see the path that they're on and we don't think it's right. And if you take these 40 years of history, you can kind of justify things and you can see how internally they can justify it and see it this way and see it that way.

John Gruber:

Somehow, they've gotten attached to this income that they've extracted from commissions in the App Store in a way that they've never been attached to other things. I mean, you and I mentioned this during this podcast about the upgrade charge they used to charge for operating systems, $129 to go from Mac OS 10.3 to 10.4. They used to charge $5 to upgrade iOS. They clearly, at that time, were trying to get away from it, but they thought the accounting rules they were trying to follow required them to do it. They've given up on that knowing that it was better for them overall.

In theory, you think, "Well, why would you ever... If people were doing it and lining up outside Apple stores to buy boxed versions of the software for $129 to upgrade their existing Mac, why would you ever do away with that if it was so popular that they were lining up?" But in the grand scheme of things, it clearly was the right decision to just make the operating system upgrades free to encourage all users to upgrade and to sort of steer them towards automatic updates, because they can do that because they're not charging. They couldn't do the automatic OS updates that most people, with their default settings on a Mac or iPad or iPhone, just at some point a couple months after the dot O, there's a version they think is stable enough. And overnight, while your phone's charging, you get the new... You're going to have iOS 26 in November or December this year.

And they can only do that because they're not charging for it and it's better for them overall. Obviously, they've never made more money, their profits and revenue are at record highs. I think the same thing is true of the commissions in the App Store that, yes, at some level, if you're the CFO at Apple, you're like, "Well, why in the world would we ever decrease this? If we don't legally have to, why would we ever give up a penny of it? It's a lot of money." But it'll all work out in the end in terms of...

And Joz himself has mentioned this in multiple of the interviews he did do last month at WWDC. He said the same thing to me and it was an off the record briefing I had with him and it was very cordial and nice. I am sure he won't mind me repeating it because he mentioned it on the record with Joanna Stern and multiple people where one of the things Steve Jobs often said, "If we make great products and tell people about them," that's the marketing part from his perspective, "tell them why they're great, it'll all work out in the end." That's just as true of the App Store as anything else, but it's this one area where they've got a compulsive institutional obsession with squeezing it that they do not need.

David Barnard:

And speaking of flukes of history, one of the... I think it was an epic case found an email from Schiller to Jobs saying, "What if we cap App Store revenue to Apple at $100 dollars?" Which at the time seemed-

John Gruber:

No, I think it was a billion. I think it was a billion-

David Barnard:

Was a billion? Okay.

John Gruber:

I think it was a billion.

David Barnard:

Or even a billion. It was like at the point in time when he wrote that, it probably sounded crazy like, "How will we ever make that much money on the App Store?" But then now, in hindsight it's like, "Oh my gosh. That's such a tiny amount to what they're making now." But had Jobs been convinced of that and had they announced publicly, "We're going to cap Apple's revenue on the App Store-"

John Gruber:

Or even if they never announced it publicly,

David Barnard:

Right. It became internal policy.

John Gruber:

Yeah. And that once it hit a billion, they dropped it to 75-25 and it stayed at a billion and it was growing some more and then they could drop it to 80-20. Then eventually, 85-15. Who knows? By now, they'd probably be at 90-10 or 93-7 or something like that. And at certain level then without ever having announced that, they could stop. If it had ever gotten even to 90-10, they could stop and say, "Well, now, we can just sort of let it grow because 10 is pretty fair." And yes, it's not the 2.7% Stripe takes or whatever, but 7% is arguably pretty good deal for everything the App Store offers.

David Barnard:

And imagine how different the last decade of developer relations would have been had Apple capped it at that. And then, the incentive wasn't for the financial side of things. The incentive was to build a fantastic platform for developers and empower them to serve our customers and keep innovating.

John Gruber:

And encourage developers and designers and even the companies and managers at those... Who aren't nerds and are into the platform, but just to encourage as much as they can, the mindset of, "Maybe we should build this for Apple platforms exclusively, because of the great APIs and capabilities and... Why even bother with these other platforms? We don't make any money on them. We're doing so great iOS only." They've really gotten away from that. It's to Apple's benefit in obvious ways to have as many developers as possible making Apple platform exclusive software. And at this point, there's such a resentment that to so many people, whether they're managers or executives or developers or just users who are like, "Well, you'd be crazy to build for Apple only because they're sort of against you in terms of trying to just take your money."

David Barnard:

As a long-term Apple watcher and being friends with so many developers. What do you think it would take? Is a reset even in the cards for Apple at this point? Would it take Phil Schiller on stage at the iPhone 18 whatever-

John Gruber:

They don't do anything on stage-

David Barnard:

... keynote. Well, you're right. But what would it take to get a reset? Above the... I mean-

John Gruber:

I don't know.

David Barnard:

... the money would probably go a long way like, "Okay. We're just going to drop the rate." But it does almost feel like there needs to be some level of that 1997 Jobs' humility of like, "Hey, we made some mistakes. You're going to see a new Apple moving forward."

John Gruber:

Yeah. But I think you don't have to do it... I don't think it's within Apple to say, "We made some mistakes and we're going to change," even though that's sort of how he addressed. He was willing to say that at WWDC 1997 because what they were scrapping were things that weren't under him, right? OpenDoc and Newton and everything else they scrapped. They weren't Jobs-led post next reunification projects.

The Apple way of doing it would be to act like, "We've come up with this amazing new idea that only Apple could do and it's totally innovative and nobody else has ever suggested it before. And it's called taking less money from the App Store," right? And not apologizing and not saying... Presenting it as a new opportunity in the same way that they're pitching the liquid glass of iOS 26 as, "Hey, the capabilities of the hardware and the GPU and the screen display technology with HDR is such that we're able to present this interface that we couldn't have done before." Just present it as the market opportunities and the success of the iPhone are such that we're able to have a new financial set of rules around the App Store that we couldn't have done before, even though they could have. But just say that they couldn't.

David Barnard:

It's just frustrating on a human level. It's like at work, when I do something stupid or whatever, you apologize. There's just humanity in that level of humility that it is just frustrating to me on a human level.

John Gruber:

But that would count as an apology, right? It would. Because we'd know.

David Barnard:

For us as Apple followers, it would. But I think in 2025, the press would have a field day with that and just call BS in a way that I don't know that it would work. And this is kind of something I've been thinking more and more is that Apple needs to do some things on Apple, like to adjust to the realities of 2025 and to set themselves up for the next decade as a platform for developers as a consumer brand and everything else.

For example, the small business program was so freaking Apple-like. Instead of just saying, "Hey, 15% for the first million, 30% for everything after," there was all these rules. You got to get into the program and then you get kicked out of the program and they created all these weird... To me, that's just the perfect example of how Apple over does things. And so, to usher in an App Store 3.0, I think we need to see them do things un-Apple-like.

And I think that... Again, it's the fanboy in me just wanting to see a new version of Apple. Not that I hate Apple, not that I think they're idiots inside Apple, not that I think anything poor of them as a company, I want to see them succeed. I want to wear Apple glasses, not Meta glasses with a camera on them. And I think there's aspects of what they're building and the trust they've built with consumers and everything else that is setting them up for potentially being that next human computing platform.

But having developers on your side and enthusiastic about it is going to be a huge, huge, huge boon. And given how competitive Meta and Google and OpenAI and others are and will be in the coming years, maybe it does require a bit deeper of a reset and doing some things that aren't traditionally how Apple operates. I think even this WWDC was a little bit of a reckoning in that Ben Thompson got it, you got it. Some people got it like, "Hey, this is Apple not overpromising so that they can overdeliver." But the press had a field day with like, "Oh, it's a boring..." They're so far behind on AI and all that kind of stuff.

John Gruber:

Nobody remembers that though. I mean, it's news for a week and here we are a month out and I think it's already forgotten. And I think Apple should have the fortitude, and the wisdom and you've mentioned at the outset, that their leadership's been there for so long. They remember this, they know how it goes, and they should just be confident in themselves in that way. The other thing about the fact that so many of the senior leaders have been there for so long, it means that most of them are nearing retirement. Schiller has stepped down and is in a different position as an Apple fellow. He still runs events, he still runs the App Store. Tim Cook is... I forget how many. What year? 64 or something like that? Or 63. Eddy Cue and Joz are in their 60s.

And I'm not saying any of them are leaving soon. I mean, I'm sure none of them are going to pre-announce their retirements. But in terms of setting things up for the next generation of senior leadership at Apple, which is coming sooner rather than later, right? It's coming over the next decade, across the board, I think that they need to reset the institutional priorities of the company, because the new generation won't have that experience from the '90s that you brought up on this show to explain this. And instead if they took over right now, will just have the mindset of, "Oh, the way Apple works is they expect 30% of all the money on the platform." That's just the way it is and that they don't have any history behind it or why, but that they think that.

As opposed to thinking that the most important thing Apple should do is encourage stoke and keep going in an ongoing relationship developer enthusiasm for building exclusive software for our platforms. And making it as great as possible and thinking, "Some of the best software experiences on our platforms are going to come from our third party developers, not from Apple." And that that's the way it should be. And we shouldn't be thinking that all of the best software comes from Apple and it's an afterthought what third parties make.

David Barnard:

And to your point, I hadn't thought of this until you've brought it up, that in setting things up for the future, I think there is onus on the current executives to not hold on to the past for the next decade when it's then too late. They're in the position, today, and having been at Apple 40 years... But one of the impressive things about Meta these past decade is that as a founder-led company, Zuckerberg put $100 billion into Reality Labs and is force of will and telling shareholders, "Hey, we're making these massive investments and they're going to pay off."

And now, he's doing the same with AI, $100 million checks to lure AI talent. That's not something the stock market normally would reward, but he is out there pitching the world that, "Hey, this is an investment worth making and we're going to make it." And I think these Apple executives who've been there 40 years are the best people to say and convince the world, "Hey, we need to make some investments on the developer front and that's going to involve less services revenue," or whatever it has to be. But it's going to pay off in spades in the long run with the innovation that's going to happen with the renewed developer sentiment and everything else. That they're going to need for this next big platform in the coming 5 to 10 years. And it may be too late if they hold on.

John Gruber:

Well, I agree.

David Barnard:

Well, I think that's a fantastic place to wrap it up. And really, what I wanted to say on this podcast and hopefully people have gotten that depth of history of when you're frustrated with Apple about this policy or that, there's a lot more going on behind the scenes than... And I mean even, again, as much as I complain on Twitter, I'll acknowledge that I lack a ton of context and I lack a lot of insight. And I'm sure I can understand why people inside Apple are frustrated at the way I frame things sometimes. But when you take all of that history and everything else into account, something needs to change. I'm not sure exactly what that is and me lobbying is me just throwing out ideas. Happy to be wrong about any of this, anything I'm suggesting. But I hope it's helpful to folks to better understand Apple in these ways.

John Gruber:

If there's one other point that I'll close with, it would be that I mentioned earlier that the problem Apple found itself in the early '90s when Jobs was exiled was this they were caught in this '80s mindset of every couple years, a new platform replaces the old platform and the old platform goes away. When, in fact, the Macintosh was here to stay and they just weren't treating it that way.

I'd say Apple's come full circle now and views its platforms as institutions that are there to last decades, including, well, all of the platforms that they have. Including the Mac, which started in 1984. But the iPhone certainly, iPad, even the lesser ones like Watch and tvOS And I think visionOS are things that they intend to last for decades which, at this point, will last well past the careers of the senior leadership at the company. And I think they have that mindset. But I think they're currently doing some things and, again, related to money, just the goddamn money, that are contrary to fostering that. But it's this long-term mindset that the company has that these platforms are institutions and that Apple at a whole is an institution that is meant to be here for a very long time.

David Barnard:

And if they don't change... Or maybe they don't have to change, I don't even know.

John Gruber:

But I think if they don't change, then when new things come, they become legacy only. They're not going to disappear. The iPhone is not going anywhere. But the risk to the company is that they become legacy only maybe like Microsoft would be if they hadn't moved to the cloud, right? If Microsoft was still just about Windows and Office and stuff like that, where they would be? They would miss out on the next thing. That their next thing isn't going to hit unless they have developer buy-in. And that you can easily disguise that with the ongoing revenue and profits from those legacy things. In the same way that Microsoft would still be a very big healthy company, even if they hadn't shifted under Satya Nadella, but they wouldn't be number two or number one in the world right now.

David Barnard:

Yeah. All right. Well, it's been two and a half hours. I think we do need to wrap up but fascinating conversation. Thank you so much for your time, John, and this was-

John Gruber:

Thanks for having me.

David Barnard:

Glad to have you.

John Gruber:

This was fun.

David Barnard:

I really enjoyed it and I hope it's useful to folks.

John Gruber:

I won't feel so bad the next time you're on my show for two hours.

David Barnard:

Thanks so much for listening. If you have a minute, please leave a review in your favorite podcast player. You can also stop by chat.subclub.com to join our private community.