443: ‘The Pogue Feature’, With David Pogue

Hey there, it's your internet pal, John Gruber. I've got David Pogue on the show for this episode, the author, well, author of many, many books, but author of the new book, Apple, The First 50 Years. David is in the midst of a very, very tightly packed media tour to promote the book, and his time is really limited. It was really kind of serendipitous that I got him at all. I got him right out off an airplane after he arrived in Seattle, after being in Portland. Didn't have the length of time I would love to have had him, so it's a little bit shorter of an episode than usual, even though we could have gone longer than usual. And because his time was limited, literally he'd gotten off an airplane and he had to go to an event. I didn't want to interrupt the show to do my sponsor Reads Live, so I'm going to unusually for the talk show, record them in post and we'll insert them in editing. And the first one, I'll just knock it out right here, is our good friends at Factor. 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And now on to the show with special guest, David Pogue. David Pogue, welcome to the talk show. You probably should have been on long ago, but if there's ever a good time to have you on for the first time, it is to mark the release of your book, Apple, the First 50 Years, which came out, I believe, a week ago? Well, give or take. Yeah, Tuesday, yeah, five days. And you are on a whirlwind book media tour. So traveling all over North America, I believe? Yeah, it's about 10 or 11 cities. And when was the CHM event? Ah, that was the first stop of the tour. That was the day after the book came out. Wednesday, March 11th, that was one for the books. I'd watched yesterday. I'd put it off, I did not watch live because I wanted to watch on a big TV and I wanted to take my time. And man, it was so good. I think, all right, let me start with this. Number one, I think the book, I have not finished it, I have to say, because it is 600 dense pages, right? It is a big book. And I kind of feel bad about that because I think every time I've had the author of a book on the show, I have finished the book before the author came on. In this case, I feel like I don't need that because I can recommend the book wholeheartedly from the introduction alone and the parts that I've cherry picked. It is so good. But it is also, in addition to being 600 pages, it is 600 dense pages, right? It's beautiful too. It is full color throughout. It's not like, oh, we're gonna put 16 pages of color in the middle of the book. And I'm glad you mentioned that because literally that was a stern conversation with the publisher. They wanted to put 16 pages in the back and you'd be reading along and it would say, please turn to page 582. Like, no, sorry, no, we're not doing a book that includes the iMac and the iPhone and printing most of it in black and white. We're just not. So I'm very grateful. It is heavy, it is thick, it is dense. It is packed with color photographs that are just terrific. It feels like what I think you meant for it to be, which is almost an encyclopedia of the first 50 years of Apple. Yeah, no, no, you're right. It did come out exactly like what I envisioned. I'd say most of the Apple books that have come along so far are written by business authors, not technologists. And that's great. There's great stories in the boardroom and the stock price and blah, blah, blah. But I've always been interested in the products and the technologies and the backstories especially. So as you've probably seen, there's a lot of pictures of prototypes in there and products that never made it to market. I actually got my hands on the one and only Apple fax machine. All ready to ship. Canceled at the last. So I really do mean this with the utmost sincerity. I'm not sure there's any person on the planet better suited to have written this book than you. It is, amongst the ways, your background, you were a columnist at Macworld for 13 years. You were the technology columnist at the New York Times I think for the same number of years? Yeah, isn't that weird? Yeah. You're still writing and talking about technology but more on TV than in writing these days. You were literally a columnist for Macworld during a huge chunk of the middle of Apple's 50 years. Your time at the Times included being one of the four reviewers who got the iPhone in 2007. So you were right there, which gives you a first person perspective but also I think a credibility with Apple to get the last 15 to 20 years, the Tim Cook era for sure, covered in any way, right? Which is, you know, and you've emphasized this in the book and at the event that Apple had no editorial control over this book but they did help you in some ways. Can you talk about the participation of current Apple with the production of the book? Yeah, I mean, if you wanted to write a book about the beginning years of Apple, you're pretty golden there's a lot of books, there's a lot of magazine articles, there are interviews with former Apple people that you can do, they've left Apple, they're no longer under NDA. The problem, as you so succinctly put it, was the last 15 years because everybody who was at Apple is still at Apple and Apple's rule is, our people do not speak to journalists as a rule unless, as you know from your onstage talk show with executives, when they're trying to make a point about AI or introduce a product or something, then they handpick the people they want to speak to. So I was literally losing sleep. I mean, how am I going to do this? Who am I going to talk to? And it took six months of making my arguments to Apple and I wrote a sample chapter so they could see what the tone was going to be like. And, you know, I stressed that it's about the products and it's about the people who created them who don't usually get credit. And finally they said, okay, we're going to line up a bunch of interviews. I mean, a lot of interviews, the entire Tim Cook executive team, engineers, designers, sensor people, the camera technicians. I mean, it was an incredible series. Four times I flew out to Apple Park over 2025 and interviewed back to back to back people. And they gave me access to the archives. So the two archivists whom I did not meet until a couple nights ago at a book signing, but I would submit lists of what I was hoping to find. And they came up with like 700 incredible images that have never been seen before. I've sort of suspected that they had archivists, but until you mentioned it at the CHM show, I wasn't sure they did. It's always there. Because part of, in addition to the culture of secrecy, which is about the current day and sort of does date back a surprising amount of time because the people at Apple have been there for so long. It's been steady leadership for a long time, but even more so under Tim Cook than it was under Steve Jobs. Ever since the ouster of Scott Forstall in 2012 or 2012 and Tony Fidel leaving, the only real high level departure was Johnny Ive, which again, it wasn't like he was forced out. It was sort of, I mean, it's complicated, but everybody else who's there has been there since then, and they're not going to talk. And even the people who did leave still tend not to talk. It's difficult. It's difficult. That is true. And there are always these reports of things that Apple has, in addition to the culture of secrecy, they do have a culture, and it comes from Steve Jobs. There's like the quote from him that, hey, if you, I'm going to paraphrase, but if you've accomplished something good, take a moment to enjoy it, and then think about what's next and move on and make something else that's great. And Apple does, as an institution, sort of have that mindset of let's not look to the past, let's look to the future. And there were stories, there used to be the Icon Garden at the Infinite Loop Park, where they had these classic macOS bitmap icons, but like six feet tall. And then supposedly they were just like, yeah, let's get rid of them, and they just threw them out or something. I don't know. And there was a museum. Yeah. There was a museum, and they got rid of it. Yeah, but I guess they didn't throw this stuff out. They gave it to the, donated it to the Computer History Museum or somebody. Yeah. But it's always been a question in my head of how does a company that is this, not repulsed, but this sort of afraid to dwell on the past, right? I think that it's like, hey, if we dwell on the past, we're going to lose sight of the future. And that they've seen other technology companies that kind of latch onto their big success and ride it into the ground and never obviate their own successes, right? Prime example, the iPhone obviating the iPod. Yes. Teach that one in business school. It was the most successful thing Apple had made. It was only six years old at the time. People still remember it. It was a much longer era, the era of iPods. And they're like, yeah, once we make this thing, nobody's going to buy an iPod again. And they're like, sure, let's do it. They know that other companies over the years in technology would be like, well, we can't do a phone that's going to, we should make it so that you have to connect your iPod to your iPhone to play music. So they still have to buy an iPod. But with that attitude, it's like, do they have an archive of all these photos? It's amazing that they do. It really is. Yeah, they do. And I understand that these archivists are having quite a moment right now. Because Apple, you know, I interviewed Tim Cook a couple weeks ago for a TV segment. And he admitted that, yes, the motto is we don't look back, we look forward. But obviously, we have to commemorate the people who brought us here. He put that in a very lovely way. And so he said, we are doing some stuff to celebrate the 50th, but it's, quote, a new muscle for us. It's a little awkward, it's a little new, they have no mechanism in place for it. And one reason for that, by the way, is I had a couple takeaways, even after having covered Apple for 40 years, doing this book, I came away with a couple things I hadn't really known. And one is how unbelievably intense it is to work there. I mean, people either quit immediately, or they really love the mission, and they stay for decades. But I mean, it is intense. And I interviewed John Rubenstein, Ruby, who was, you know, the head of hardware for the iMac, iPod, iPhone at the beginning. And I asked him, so, it was his idea, by the way, it was Rubenstein who decided, we're gonna do a new one every year. So that's why we get a new iPod, and now a new operating system, and now a new iPhone every single year, that was him. Originally, because they were convinced that Sony was on their heels when they made this music player. Yes, Apple came across the world's first Oreo-sized hard drive. They found it in a Toshiba meeting, that Toshiba had come up with this and didn't have any takers for it, didn't know what to do with it. And Rubenstein's like, we know what to do with that. We'll buy, right now, we'll write you a check for $10 million, we'll buy all you can manufacture. But after that point, he was convinced that Sony was gonna come out that Christmas with a competitive project. As it turns out, Sony did not come out with a pocket hard drive-based player the first year, or the second year, or the third year, or the fourth year. The fifth year, they came out with a Sony MP3 player that, as you may remember, could not play MP3 files. Oh, that's right. That's right. It could only play Sony's proprietary format. So arguably a bad feature in an MP3 player. If you described that to somebody, company A did it this way, company B did it that way, that would sound like Apple to some people's ears, right? That Apple made the player that only played the proprietary format. That's right. But how this ties into your comment is that Rubinstein said, when they had the Mini, which is the first product to sell hundreds of millions in Apple's history, I'm like, well, there must have been a big beer bash. There must have been. He's like, no, we never had time. We never had time. He said, every time they launched something, the next morning, they were all guns blazing on the next one. And that's the real reason they don't look back. They just don't have time. And I know somebody at the Computer History Museum event even cited Andy Grove, who is from Intel, but his famous maxim that only the paranoid survive, and that that's how Intel stayed on top for so long. And I think you could also say it's sort of how Intel has sort of fallen out of mention as one of the big tech companies in the last 15 years or so, that they sort of lost that paranoid mindset of, I think if they had it, they would have seen the initial iPhone and when the iPhone took off and thought, hey, we're not a part of this. Nobody's making these, whether it's Apple or whether it's the Android competitors, nobody's using Intel chips for these. We need to be in this game. We need to do whatever it takes to be in this game. And if that means all new chips, all new chips, it is. We need to be there. And instead they were like, ah, well, whatever. That's cute. But I do think that that mindset, it's sort of like when you're onto something, it's hard not to think, well, this is a great idea. And when you realize it's a great idea, it starts to seem obvious and you think, well, everybody else must be onto it too. And so when Apple realized this iPod idea is so great, we put it on the market, each successive model is selling more than the next. There's obviously this huge demand to make it something other than a Mac peripheral, to put a version of iTunes on Windows so that it'll sync to anybody's PC. Surely every single competing company in the world, including the one whose design chops we respect the most, Sony, is going to come after this with guns a-blazing because they're going to see what we've got our hands on right now. And no, they didn't. But they convinced themselves they did. And it motivated them just as much as if Sony were competing with them. That's right. And I'm doing these book talks and one of the points I'm trying to make in the talk and the book is everybody knows that Steve Jobs could see the future, blah, blah, blah. But even in instances when everybody who knew anything about business or marketing knew that he was wrong, like in the classic case is the iPod mini. Again, it was the best-selling electronics project in history, hundreds of millions a year. And Jobs said, right as it was ascending, it was ramping up. He said, okay, we're going to shut it down. And like, what are you doing? Like Rubinstein was like, no, Steve, no, no, this is wrong, this is crazy. And he's like, yeah, we're going to replace it with a new model that holds less music, the Nano, right? It's smaller and cuter, but it doesn't hold as much music. And the entire team was like, that's insane. People want the mini. And Jobs shut down all the factories. He stopped ordering parts for the mini. He transferred all the marketing money to the Nano. And he was right. How? How did he know? I don't get it. Right, and it's that inflection point between spinning hard disks, which held more data, but which are fragile, slower, less reliable, to SSD-type storage that has no moving parts, is much, much more reliable and smaller, but dollar for dollar holds fewer bytes, and therefore fewer songs. And yeah, there was something, your book and the event covered where early, if we go back in time, let's just zip all over the timeline here, but go back to the 1985 or so when Jobs was on the cusp of being ousted from Apple under John Sculley, and Jobs came to Sculley and said, hey, we're getting, the Macintosh is not selling as well as it should. It's because you made me price it at $2,500. We need to get the price down. And Sculley's answer was, well, you wanted a huge marketing campaign. It's the marketing dollars that are driving the price, keeping the price this high. And Jobs wanted Apple to stop marketing the Apple II, take all the marketing money from the Apple II so that they could lower the sales price of the Macintosh. And people who weren't around in the 80s don't remember this, but it was the Apple II, pretty much for most of the whole decade, years after the book came out, that Apple's revenue was from the Apple II line and the future was the Macintosh, but the Macintosh wasn't selling enough to keep the lights on in Cupertino. It was the Apple II. And really that's what led to Jobs' ouster. It was that simple. He wanted to kill the Apple II and he probably was wrong. We can't prove what would have happened if they said, okay, Steve, whatever you want, we'll do it. But it probably wasn't going to happen. The people who were buying Apple IIs, and I've told this story. I was around, I was a kid at the time. I was like 10 years old, 10, 11, 12. I thought the Macintosh was interesting, but to me, it wasn't really a computer in the way that a Was computer was a computer. A computer was a thing that I turned on and I wrote software for. 10 print, John is awesome, 20 go to 10. I was writing more complicated programs, but that's what a computer was. And the Macintosh wasn't that. It was like, wow, this is really cool. And I was intrigued by it, but it really was a place where you ran software that was complex software written by other people that you ran apps basically in today's mindset. Whereas the Apple II, you wrote programs and you could run apps. There were word processors from Apple and other companies and spreadsheets and stuff like that. You could run apps, but you also wrote apps. And it just was a different mindset. And that's what the market wanted. The market wanted, including the big education market, wanted computers where the kids could turn them on and start writing programs for their programming assignments, right? And the Macintosh wasn't that. So I think Jobs was wrong then. And that, what did you call it in the book? The interregnum, the period where- When he was gone, yeah. His exile, I often call it his exile. He was a different man when he came back. And it's probably all of the above, age, wisdom with age, the humility of sort of being forced out of the company that was more successful, the fact that Next never really took off. It was sort of a footnote in the computer industry. Pixar hadn't really taken off yet. It was obviously a very interesting company that had a very bright future ahead of it, but wasn't the Pixar we knew, right? Toy Story didn't come out till 1997. Humility, age, I don't know, but he came back a very different person with, I think, a better sense of things like that, right? Well, yeah, because if you think about it, the entire Steve 1.0 era, he never had a successful product. Right. So, I mean, Apple II, which was wise, but Apple III, nope. Lisa, nope. Macintosh, nope. Not for the first few years. Next, nope. And then when he came back, he had almost nothing but tremendously successful products. I mean, iMac, iPod, iPad, iPhone, iMovie, iPhone. I mean, just incredible run. And yeah, the two jobs could not be more different. Yeah. You can see the run through, right? The impulse is the same. That's why I thought back when you mentioned that he was like, nope, we're going to kill the hard drive-based mini in favor of the smaller, cooler-looking Nano. Even though dollar for dollar, it's going to store fewer songs because it's almost like in Star Wars terms, the force. He could use the force and could tell, you know what, that's enough songs. And I think he was probably right where with the initial iPod, the 5,000 songs in your pocket, most people don't have 5,000 songs. No, they don't. And I mean, speaking of music, he was also dead wrong about people want to own their music. Yeah, totally. He hated the Spotify model where you pay a monthly fee and he would say, and I remember being convinced by this. He said, the day you stop writing a check to Spotify, you lose all your music. You've got nothing for having paid all that money. But it turns out that's the model people want. Yeah, and it is the ownership. That's another thing too, where it is almost, it's longer than like the iPod. But I was just talking about this, I guess with my wife, but that, you know, and we have a college age son and he just doesn't know the idea of owning music just doesn't really register for him. And we were trying- That's wild. We were, as my wife and I went to college in the 90s and both of us, and I remember very vividly doing the math because that enormous part of my, the majority of my liquid net worth as a college student was tied up in compact discs, right? Because my bank, my actual ATM card, the other story I love to tell is that I went to Drexel here in Philly. I knew where the, I had a core state, one of those banks that got eaten by a bigger bank, eaten by a bigger bank, eaten by, you know, now it's part of probably Bank America, who knows which bank? But Core States Bank had an ATM on Drexel's campus that had no fees for me because I had a Core States Bank account and gave $10 bills, which was important as a college student because sometimes I had less than $20 in my checking account. But what I could do for money is take some of the CDs I had, go to the used CD store and sell them for a reasonable price to get cash, right? And then if I wanted to buy CDs, I'd buy them used instead of buying brand new. But, you know, I had hundreds and hundreds, I guess probably over, you know, thousands of dollars in CDs, you know, because I owned all my music. I had a big collection of compact discs. And if I needed money, I would find some that I was like, ah, I don't listen to that anymore. Take it to the used CD store and all of a sudden I'd have 30 or 40 bucks in my pocket. It makes no sense. Try explaining that to the kids today. It makes- Although I noticed, interestingly, iPods are suddenly hot again because of the smartphone bands in schools. So kids need a way to listen to music that's allowed and it's iPods. Yeah, and I will say my son, I noticed it because we have an old car and it has a CD player. He's started filling it with CDs. Like it is sort of a retro, like the way that my generation got back into vinyl, kids today are getting back into CDs. But the whole idea of owning music is sort of an interregnum, right? Because previously people just listened to the radio, right? You'd turn on the radio to listen to music. You didn't pay and you listened to ads in between songs. And then there was a period where people bought albums for a while, tapes and CDs. And now it's just pretty much back to the radio except it's Spotify and Apple Music. Right, right. You're making it sound really old, John. Well, we are. And it's, but it is, I understand that Steve Jobs mentality of, hey, I don't want to pay anybody any more money. I already own all of Led Zeppelin's albums, right? It's, I've paid once for the box set. I don't need to pay anymore. I'm trying to think what, again, we could talk forever, but there is, in the Jobs 1.0 era of Apple, and I think your book makes this point clear. There really wasn't a strong CEO figure. Jobs was not the CEO at the time, right? It was Mike Scott for a while. And nobody, that's like a name you just never hear anymore. Nobody's ever like, yeah, remember Mike Scott. Those were good times at Apple, no. You know, he just died. And there wasn't a whisper of press release, memorial, acknowledgement, nothing. In fact, I will say that that's one really meaningful thing about the 150 interviews I did for this book. Four of those guys have now died or become unable to speak since I did the interviews, including Bill Atkinson. It was his last interview. And so really, I'm glad I did this one I did. I think that's, just to go back, I think that's why the 50th anniversary is so special. Like, it is a big round number, right? Obviously, 100 in our numeric system is a bigger number, but we're not gonna be around. None of the people who are around are gonna be, none of these people are gonna be around for Apple's 100th anniversary unless Apple Health is a better success than we anticipated being, right? 50 is the big number where, it's the biggest number where the people involved are still going to be around to be interviewed and tell their stories for it. And it's also a further blessing that when Apple was founded and through the 80s, so many of the principal players were so young, right? So that 50 years later, they're still, the fact that some of them like Bill Atkinson and of course Steve Jobs have already passed, and that some of them are starting to fall to other things like dementia and things like, or just faulty, just the memories. Now, maybe they're not suffering from dementia, but they don't remember what happened 48 years ago, which happens to everybody eventually. This is the one where it's the sweet spot of an anniversary that hits the most number of people who are still there can recall the stories. Yeah, bingo. And fortunately, there's one and only one person who's been at Apple for all 50 years. He joined when he was 14. It's Chris Espinosa, he's still there. And thank God he not only has been there, but he has a steel trap memory for detail. He's a great storyteller and he's an incredible technologist. Like his explanation of what went wrong with the Apple III, I've never seen written anywhere and it was golden. He is one of a kind. He was 14 when he started working there. I think you cracked a joke on the stage event. I don't know what the California child labor laws were at the time. His mom would drive him to the Homebrew Computer Club meetings and wait outside in the parking lot. He couldn't drive. But still there, he's not there in any kind of ceremonial sense. To my knowledge, I think he still runs the developer tools group, right? Or do you know? He's working in TVOS now, but he's been working in all kinds of places. Right. Yeah, yeah. He told me that his, sorry. He told me that his phone is blowing up this week and his cubicle is constantly darkened by people stopping in, both because of the Computer History Museum event and that's now on YouTube and getting a lot of attention, but also just because he's the guy who's been there for 50 years. Continuously in positions of relevance and remembers. That is a sort of difference between then Apple and today's Apple. Yeah. Imagine if, like, there was a cellular reception issue with the iPhone and the solution was to drop it six inches off the table, onto the table, and that'll reseat the cellular modem. Oh, I thought you were going for a joke. I thought you were going to say, imagine if there were a cellular reception issue and they told you that you were holding it wrong. Almost the same thing. That's probably the closest we've come to a similar issue. 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When you use that link, you're supporting the show, notion.com slash talkshow. Before we continue into the minutia of some of these stories, talking about your writing the book itself, when did you decide to write the book and was there a point where you got worried that there would be too many of these Apple at 50 books coming out? Because as it turns out, it seems like yours is the only one. It's the only one. I'm boggled. I mean, not even Apple. Not nobody. I'm absolutely ... It's like John Rubenstein with Sony hit his back, you know? It's exactly what made me think of the question, right? Was there a point where you're halfway through this book and you know you've got gold, right? You're like, I've got sources. I've got these great stories. This is coming together. There are going to be a zillion of these books. I was worried for the entire two years. So I hosted another thing at the Computer History Museum in 2024 to celebrate the Mac's 40th anniversary. They brought back Bill Atkinson and Andy Herzfeld and Susan Kerr and Steve Capps and Bruce Horn and Guy Kawasaki and all these legends from the Macintosh days. That's on YouTube too. That was unbelievable. It was just ... The audience, it was like Woodstock and these guys were laughing and crying and PTSD. It was really an unforgettable night. It was actually my wife's idea, this Apple at 50 book. She woke me up a few weeks later. I was supposed to be working on a different book, first time an issue, sir. She woke me up. She's like, you should dump that other book and do a book about Apple's 50th. I told this on stage. I literally shut her down. I'm like, Nikki, you missed that. That's gone. That date has come and gone. Then in the morning, I looked it up and she was right. It was two years away, just enough time to write a 600-page book if you're crazy. The part that worried me most was I felt really intense pressure about the different contingents, the different groups of people who were going to pin expectations on this book. There's Apple fans and they want to know the internal stories, the fun stuff, the making of the origin stories. There are Apple haters who are going to be looking over my shoulder to make sure I'm not kissing their ass and not giving them a pass on Foxconn suicides or whatever it is. There are the people I'm interviewing and, man, this was crazy. A lot of these guys are older and I could see in their eyes this was their shot at immortality. They wanted the story right. They wanted the credit due to them. They wanted the old mistakes that have been passed on from author to author corrected. It was so important to them that the story be told correctly. Then there's who is the book for? Are there going to be business schools who want to know about the financial shenanigans that Fred Anderson did to save the company in 1996? Are there going to be casual readers who aren't Apple diehards but they just like a really good yarn? This is the greatest corporate turnaround in history. They went from six weeks from bankruptcy to making a $45 million profit in one year. I mean, that's unbelievable. That was the biggest stress is I felt all these different audiences, you missed it. You didn't say this. You were to this. I felt like it was threading 10 needles. So far, I think I pulled it off. I think so too. It reads great. I have a very specific question. There's a part where you're talking about the original iPhone and you talk about what the New York Times technology columnist said about it at the time. Now that's you, right? Yes, that was me. I mean, what am I going to do? I wrote this in the New York Times. There's a few of those. There's a few times where I'm quoting reviews, but they were my own. You're the only person, John. You're the only person to catch that. It's funny because in certain tertiary ways, I was a character in the Apple story and this one did not make it in the book and I've never told this story in public. But the way you take a screenshot on the iPhone, press two up, internally, they call that the Pogue feature. I'll tell you why. In 2007, I was writing the first iPhone missing manual, a how-to book about the iPhone, and there was no way to create screenshots with the original iPhone. So I contacted Apple PR and said, you have screenshots in your ads, in your documentation. You must have a way to take screenshots. And they're like, well, yes, we have a very not polished looking internal tool that we use. And I'm like, can I have it for this book? So it looks good. And they went all the way up to Steve and the answer was no. They said, you can fly to Cupertino and you can sit in a conference room here under supervision and use our tool to take your screenshots. I'm like, OK, great. I'll book my flight. And then two days later, they said, Steve's changed his mind. You can't use the tool at all. But we will set aside an engineer. If you describe exactly every screenshot you want, you know, this is a spreadsheet in the first column, it's revenue. You describe exactly what you want. We'll have this engineer make the screenshots for you. So this poor slob, whom I've never identified, spent the entire summer taking 400 screenshots for this book. So then cut to, and they were beautiful and they worked out great. But then cut to a year later, the second annual iPhone comes out and I called Apple PR. They're like, no, no way. We are not doing that. We're not giving you an engineer for the whole summer. We will put in a feature built into the iPhone. You press these two buttons and you take a screenshot. So that is with us today on every iPhone and every Android phone. And that was for David Pope. That's a job well done. You have been a player in this, like, you know, being the back page or one of the back page columnists in Macworld Magazine was a thing. It really was. And you've been writing about this stuff for a long time. You know, the Missing Manual series was super influential and that was your imprint. I remember you wrote the user manual for Conflict Catcher. Yeah. Right. And now, and what's his name? Jeff. Jeff Robin. Jeff Robin, who is still at Apple and has been, at least my knowledge, he's still at Apple, was in charge of iTunes, might still be, or Apple Music for a long time, the software. But before he went to Apple, before he wrote the music player Sound Jam that Apple purchased that became iTunes, he had this utility for the classic Mac OS called Conflict Catcher, which again, a description of Conflict Catcher is going to sound crazy to people who weren't around for the tail end of the classic era. But to really trick out a Macintosh in the 90s, you would install third party system extensions and control panels that would add features to the operating system depending on what business you were in or what fun stuff you wanted to do. But if you were in graphic design, almost everybody ran Adobe Type Manager, just to name one that was very serious. And Adobe Type Manager was a way to get PostScript fonts to render on screen beautifully. And it had anti-aliasing before the system did anti-aliasing. But because all this stuff came from third parties, they often conflicted with each other because they would patch the same traps in the operating system. And if two extensions were trying to write to the same magic spot, you'd have a conflict and your computer might not boot up successfully. And you'd have to boot up with the shift key down and take half your extensions out and see if that did the trick. And if it did, put those half back in, take the other half out. And it was this whole thing to try to figure out which to extend. Jeff wrote Conflict Catcher, and it could identify the conflicts before they happened. And you could make sets of extensions so that if you were doing graphic design work, you'd have these extensions enabled. And if you were going to switch to doing music, something I'll bet you did, right? And you'd have different extensions so that a MIDI keyboard could connect to your Mac. Switch to a different set of extensions, restart the computer. You wrote the manual, and the manual, it didn't read like a manual. It read like a David Pope book. So when you bought Conflict Catcher, you got two things. You got incredibly useful software as a power user on the Macintosh, but you got a David Pope book in David Pope's voice. And me, this is like 1997 or something, I guess. I already knew what I wanted to do with my career, which was sort of do what you did. And I'm like, this is amazing because A, it's great software, but B, there is a place for somebody who wants to write with a voice and with style and inform people, right? Like your book, the manual for it taught people how they wouldn't even need Conflict Catcher, right? It was like, here's the reason why you need it. If you want to, you could just take this information and do it on your own. But since you already have the book in your hands, you probably paid for the software. And here's why owning the software will make your life easier. Yeah. Well, I can't believe you remember the Conflict Catcher manual. I'm so glad you liked it. But the Jeff Robbins story goes back even farther. I don't think I've really ever talked about this either. Jeff Robbins rose to prominence at Apple because he wrote iTunes, the app, right? But that was not Jeff Robbins' first music app for the Mac. In the late 80s, when I was still a Broadway conductor, I was a musician. I had a job on the side working for a company called Music Theater International. This is the company that rents out Fiddler on the Roof or Les Miserables if your school wants to do it, right? And our CEO thought, it's too hard for some junior high school choir teacher to play these difficulties of music, to teach the kids the songs and the choral parts. What if we had a little app and it could play MIDI files? It could play just the sopranos, now just the tenors, and now here's the dance break but at half speed. It was basically a MIDI sequencer early on. And I was put in charge of that project, and I found this kid, this genius young programmer, to write our MIDI playback app, the Rehearse Score, intercapped S in the middle, Rehearse Score. And so Jeff Robin and I worked together to write a music playback app long before you would then go on to write iTunes. But I like to say I'm the one who got Jeff Robin his toe in music software. Well, that's an unbelievable story. But again, with the talented teenagers or young people, precocious programmers doing amazing things with these computers that seem so technically primitive in their capabilities to today's eyes, but doing amazing things. No, I definitely remember the Conflict Capture Manual, because I remember thinking there might be a future for me writing about this stuff, you know? And turns out... Yes, maybe. We were talking before that in the early years of Apple, the Steve Jobs 1.0 era, they didn't really have a charismatic or influential CEO, really. The products of those early years, from 76 through Jobs's ouster, or I guess when Scully came in, which was like 1983, the products were just driven by the two Steves, right? The Apple II was clearly more the WOS computer. And then, you know, the Lisa and the Macintosh, you know, the Steve Jobs computers. There really have only been... There haven't been a lot of CEOs in Apple's history, but the three main ones, and I think they define three eras of the company. John Scully, 1983 to 93, Jobs from the return with Next in 1997 through his death in 2011, and then Tim Cook after that. And those three CEOs, those three eras are very different, right? Your book even opens with somebody, a woman who's been there since like 19... We're in the 90s, and she's like, I've worked for five different companies, but they're all named Apple. You had Scully on stage for the CHM thing, and I thought that was a pretty cool thing, because as much as you can see the mistakes that he made and the way that he wasn't the right person for the long run, overall, he was a successful CEO, right? I think that the idea that, hey, he's the guy who ran Steve Jobs out of the company, and then he got run out himself, and he was the guy behind the Newton, and the Newton was a joke, so therefore he was sort of a bum, you know? And that really isn't fair to the Scully decade at all. No, it's amazing. I mean, he also was the guy who got the Macintosh under RISC processors, which are still with us today. He developed QuickTime. He developed the PowerBook. He put Apple on the laptop map with the PowerBooks, huge, huge success. They sold a billion dollars' worth of PowerBooks the first year. He did a lot of things that kept the company growing and thriving. The first speech recognition, that happened under Scully. I do think he's gotten a little bit of a bum rap. I mean, he wasn't Steve Jobs. Nobody is Steve Jobs, but he did keep the innovation going, and I would say he was even more of a product idea guy than Tim Cook is. I mean, remember the 1987 concept video that Scully would show off at educational conferences, the Knowledge Navigator? I mean, it was a mock-up of a—it was like a six-minute short film about a professor in the future who comes in with an Apple-branded folding tablet. It is very obviously an iPad, except that it folds in half and expands with a front-facing camera, and he's on the internet, which was still six years away, and there's an AI bot in the corner talking to him, which was decades away. In natural language. Right? Just talk to it. In natural language, yep. Right. And he's doing a video conference. It's FaceTime, decades before there was FaceTime. I mean, the number of technologies on display in that little video that didn't exist then but now do exist in almost exactly that form is stunning. And of course, the answer is not necessarily, oh, they were so visionary they knew where technology is going. It might be the other way around, but that video was so influential that people thought, oh, maybe there should be multi-touch. Maybe there should be wireless internet. Yeah. So we don't know which is the cause. And the Newton gets a bad rap in and of itself, not just the Scully era. I had one, and there was something unsatisfying about it. And the big obvious thing that was missing from all of those devices, and then I wound up with the Handspring visor on the Palm, but not a Palm-branded one. It was like the Palm founders went and founded a sort of an Apple-like story where they left, started their own company, Handspring, and licensed the OS, and then made better products than the company. But all of those devices, the Newton or the Palm, the big missing thing was always on wireless internet, right? And they didn't have wireless internet at all. They all predated Wi-Fi, let alone cellular data networking. And it turns out that all of those things, not that they were useless, but they were almost useless. And if you think about what people do with their phones and have ever since 2007 when the iPhone came out, it's about being connected to a network at all times. Yeah. That's the secret. And you could talk about multi-touch, and the color, and the size of the phone, and the simplicity of just having that one home button on the front. All of those were great, you know, the software, keyboard, but what did you need the keyboard for? It was for texting emails and text messages to people, right? Yeah. Yeah, that's right. I mean, there are exceptions, and there are people who've written books by thumb typing them on their phones, but not a lot, you know. I'm guessing that out of the 600 pages of your book here, you didn't type many of them with your thumbs. I would say zero. But the interesting thing that you mentioned that these things were worthless without wireless reminds me of the iPhone story. When it came out, it sold only okay. It did not sell because it came with 16 apps and jobs, you know, Mr. Closed Systems. He would not allow an app store. For the first year, there was no app store, and people started, as I'm sure you remember, jailbreaking these phones using illegal tactics to install their own apps. And Scott Forstall, who was the head of software for the iPhone and Mac OS X and other projects, who is now a Broadway producer, which is affinity with you, right? He's not done an interview with a journalist, you know, since he left Apple. One thing for the Computer History Museum, and that was it. But I made him a QuickTime video of me playing the opening of Hadestown, for which he was an investor, and saying to him, begging him for an interview. Anyway, so he told me this incredible story that people started jailbreaking the phone and Forstall would show jobs, like, honestly, these are cool apps. And jobs would be like, all right, all right, I'm convinced. Here's what we're going to do. You and I are going to sit down, and we're going to make a list of every app anyone could ever think of. And then you are going to assemble the world's largest army of Apple engineers to write every program. So he wanted to have his cake and eat it too. He wanted both to have a closed system, right, because all the apps would be written by Apple, and an open system in that he wanted to write every app there could ever be. I mean, total insanity. I just read that, and Jobs told him, I'll give you a blank check. Yeah, that's right, that's right. And Forstall was like, okay, this is pure insanity. And behind Jobs' back, went to his team and said, here's what we're really going to do. We're going to start building the foundations of an app store. And so by the time Jobs finally came around after a year, okay, okay, we'll open an app store up to anyone. Forstall was ready to say, guess what? I've done most of the work for you. And Jobs was like, oh, you son of a bitch. And that was when the iPhone really took off, because not just apps, but entire businesses, you know, DoorDash and Airbnb and Tinder and Uber and Lyft and all of those things from that Apple. Couldn't exist otherwise, really couldn't. I'd heard pieces of that story before from other reports, other books, things that I've been told, but I've never heard it, that part of it that Forstall told you for the book, that Jobs at one point became convinced, well, obviously we need more apps for the phone, but we'll write, we'll just write them all. I have never heard before. And that is total Steve Jobs idea. And I've met Scott a few times, not recently, but since, you know, it was when he was still at Apple. I can see why he got along so well with Steve Jobs, but also there's a practical side to him, that he recognized the folly of that in a way that Steve Jobs, even at his peak as CEO, maybe couldn't recognize the folly of thinking that Apple could, you know, if there was only going to be one word processing app for the iPhone, where's the competition going to come from, right? If there's no competition, you know, and then Jobs's mind is, well, we're going to hire all the best engineers, so there doesn't need to be competition because we'll have the best designers and the best engineers. So of course, it'll be the best possible theoretical word processor for the iPhone. So we don't need competition. And anybody else would be like, no, that's not how the world works, right? And that that's a through line of Apple, though, like people being so convinced secretly that Jobs was wrong, that they contradicted him privately. I mean, this goes back to the first Mac. The first Mac was going to come with 128K of memory, and everybody could see Moore's law at work. They knew that by the time this thing shipped, it would be obsolete, that memory would be cheaper. And so Burl Smith, this genius hardware engineer they had, he secretly put traces in there, like copper circuits on the circuit board that would permit hobbyists to expand the memory without having to buy a whole new Mac and thousands of people without telling Jobs. Right. On the bill of lading, like on the list of parts that they had to pay for, they called it something hilarious, like commensurate free module or something like that. It wouldn't let Jobs know that it was a memory expansion slot. And there are a bunch of stories like that. In fact, the story of how Jobs got back to Apple in 1986, Apple was about to buy B, remember the John Lewey guy, because Apple desperately needed an operating system. The Mac OS still was not a modern, had no memory protection or multitasking, really. And so this guy at Next, where Jobs had failed to create the next hardware computer, but had a kickass OS, Next Step, this guy who is a developer relations guy, not even on Jobs's team, at the risk of his job, he called Apple's CTO without anyone's permission and said, I think you should look at our OS. Why are you messing with this BOS thing? Ours is so much more complete and so much better. And so Ellen Hancock, the CTO, called Jobs and said, OK, I hadn't thought about this, but let's set up a meeting and show me. And so this guy who all writes Garrett Rice's name, he all by all means, he should have been fired. Instead, Jobs hailed him in an all hands meeting and wrote him a check for 20 grand for going rogue and calling up Apple. There's a picture on as we talk about this transition from Scully, who got forced out in 93 and then Jobs coming back in 97. There's a picture on page 251. I'll show it to you. I'm going to put it in the album art here for the chapter. But it's Scully's executive team. And it's Scully's executive team from left, Kevin Sullivan, Joe Graziano, I think he was the CFO, Michael Spindler, who took over for Scully in the intervening years. And as you report and multiple people have reported, he had anxiety attacks and would hide under his desk, curled up in the fetal position. David Nagel and Al Eisenstadt. It's six white guys all wearing identical navy blue suits, white, all with white shirts and ties. And that is clearly not what the executive leadership team at Apple should look like. I had a conversation with Phil Schiller, like off the record just a couple years ago. And I don't know how we got talking about it, but it was one of the court cases, maybe the epic one. I don't know. But something where he had been testifying in court and he said, you know, I only wear a suit for three things, weddings, funerals and when I have to go to court for Apple. And two out of the three of those are not good. They're not happy occasions. Phil is a great storyteller. You know, during this interregnum period when Apple just sank and sank and sank and sank and they had 50 different Mac models and 12 different ad agencies and everything was going to hell, just fiefdoms and redundancies. Phil told me that at one point, two Apple trademark lawyers showed up in trademark court to sue each other. That definitely sounds like Apple of the time, right? Yeah, it was almost like a federation of individual fiefdoms. But the gist of it was that, like Phil said to me, that if it's a wedding or a funeral, you have one good suit and you can work for both. But when you're going to court every day, you need a bunch. And so like every time you'd have to like go out and buy suits because he didn't own them. You know, he's a longtime senior vice president of Apple. By the time he stepped aside and became an Apple fellow, you know, they were the biggest company in the world. And he didn't own suits because he didn't need to because he worked at Apple. And I never worked at Apple, but I've always been fascinated by the company. And I remember as a kid in the 80s, I read a story about the company and it said all of the engineers showed up at work in T-shirts and jeans and sneakers. And they were like, yeah, we just want to be comfortable. Why in the world should we dress up? You know, why would we put a suit, shirt and tie? And I remember telling my dad this. And my dad said, John, there is no computer company out there where you show up to work in a T-shirt and jeans. And I'm like, I'm telling you, Dad, they make the best computers. They make the best. And he's like, John, that's not true. But there's something to that, though, where fundamentally, Scully wasn't meant to be there for long. He got Apple up and running, but it it wasn't meant to last. Right. Yeah. And that was the funniest part in that Computer History Museum event that you watched. I asked him, so you were there 10 years. What's the story of your leaving? And he goes, I was fired, like pure and simple. I mean, there's just so much like nobody's Steve Jobs, like not even in Apple, outside Apple. Tim Cook gets this knock. He's not a product person. They've had no big hits like Steve Jobs level hit since he took over. AirPods and Apple Watch are both accessories for the iPhone. They're not new platforms. The Vision Pro failed. He spent $10 billion developing a car that failed. But on the other hand, nobody in the world has come up with a jobs level new platform either since he died. So it may just be that that was a perfect era of miniaturization and Chinese manufacturing and the public getting used to technology and that Jobs was there at the right time and that the world has now moved on to software and services, which is, of course, exactly where Tim Cook took the company. I thought your book covers it well and I thought the event covered it well that it is sort of an unfair knock and the iPhone really is the culmination of what Apple was set out to make. And at this point, the iPhone is almost, you know, next year will be 20 years. So it's about 40 percent of the company's history, you know, time wise. And that's what the iPhone is. But I almost feel like with the iPhone, and they even said it, like, did you guys think it was gonna be as big a hit as it was? And Avi Tavenian and Chris Espinosa, they were like, no, not really. No, they were kind of surprised. And Jobs was asked that while he was alive, and he also said no. No to the first iPhone. Yeah, and I think that it sort of is right there with his initial reluctance to open it up. You know, that I think, if he had been thinking about 2 billion users, he would have known it had to be open. And as opposed to making just sort of another iPod-sized hit, which, you know, if that's how big the iPhone had gotten, as big as the iPod had gotten from 2001 to 2006 or 2007, that still would have been a success at that time for Apple and for the cell phone industry, but it wouldn't have changed the world. It wouldn't have redefined the way that the entire world works. Nobody was writing books in 2006 about iPod addiction, right? Right, that's right. A lot of people that I spoke to regret the dark stuff that the iPhone has unleashed. You know, I mean, you could argue that's why Apple and the rest of the industry are now working on how can we use the benefits, the virtues of that online always computer without occupying your eyes. So that's why they're trying to see what else they can do with AirPods. They put the heart rate monitor. They're playing with putting a camera in there or Johnny Ives' new company is talking about a pendant or a badge or a necklace or a thing you wear in your head. That's why smart glasses are a big initiative for everybody, including Apple. And I think that's exciting. I mean, maybe, and Eddie Q, Apple's VP of services, recently testified in one of those copyright patent lawsuits that 10 years from now, it won't be about the iPhone. We won't be pulling this thing out of our pocket all the time. Or it might not, I think is what he said. Because I don't know. Right? Who knows? But I think if Apple's still Apple, if somebody is going to obviate it, they want to be the ones. But I do think that that's the bum knock against Tim Cook, where I'm with you, where I don't really see the missed opportunities after the iPhone for something that would be as exciting as the iPhone. I really don't. And the fact that nobody else made it, it's not like you can say, hey, Apple missed out on blank, which is a computerized consumer electronic device, that you can't, it's really hard to say that they did. I really think that a iPhone-sized device that's in your pocket all the time and can run any software imaginable, it's like an inflection point in computing. And I don't think it's the endpoint, right? I think that we will start to see things like, who knows if it'll be glasses or earpods or pendants or all of the above or something like that. And it'll involve computers getting ever smaller so that the iPhone seems big and hulking compared to these computers. But it's one of those things where it's a decades-long gap between where the modern phone came out and this came out. And I think that if you took somebody back to 2012 when Tim Cook first took over as CEO and had them live in the world of that time and the phones of that time and the camera quality of that time and what you could do, like, well, this all seems kind of slow and limiting, but let me get an Uber. And it's like, no, Uber hasn't been invented yet. You know, did you, I'm sure you've seen the movie Her, the independent movie Her. Most people haven't. It was like an indie film, but of all. Spike Jones, right, directed. So of all the movies that depict future technologies, I actually think that one's the most plausible. So, you know, in this near future, everybody's wearing what amounts to an AirPod, and you do all your computing and information seeking by talking to this glorified Siri played by Scarlett Johansson's voice, right? But then you have to answer the question, what if someone wants to send you a picture or if you need a map or you need some visual? They also have in their pocket this little index card-sized screen that they could whip out and look and then put it back in their pocket. But most of it is offloaded to this thing in your ear. And I think that's actually a fairly plausible future. I do too. I think that is very prescient. And it feels, I forget when I rewatched it. I watched it when it was new, and then I rewatched it at some point after AI became a big thing. So let's say like two years ago. I don't know, a year or two years ago, I rewatched it. And it's like, yeah, this really holds up. It really does. It really does. You know, I'm a big Kubrick fan, but I also feel like 2001 A Space Odyssey really holds up in terms of there's one computer, Hal, but you talk to it on multiple devices throughout the spaceship, right? It's one computer, but he's got multiple outlets. And that's sort of the vision of AI in the future where you don't, it's not like your AI lives in your phone. You keep your phone, you could keep it in your pocket and talk to it through your headphones. Or if you're at the gym and the phone is in your locker and all you've got is your AirPods in, and you could still bring up the context. You're not talking to your phone. You're talking to something up there. Yeah. That's the vision. All right. This episode is also brought to you by our good friends at Squarespace. You guys know Squarespace. Squarespace is the all-in-one website platform designed to help you stand out and succeed online. But it might not just be you. It could be somebody you know who turns to you as their nerdy friend who knows how to make websites. Send them to Squarespace using the code squarespace.com slash talkshow and your friends don't even have to listen to the show, but they can come here. You'll get credit as the person who listens to the show who sent them to Squarespace from the talkshow. 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The other thing that I concluded from doing this research is that Apple has quietly crept up on us as it turns into a medical company. It's just unbelievable how advanced their medical sensing technology. I mean, it's more or less diagnosing atrial fibrillation, this devastating heart thing that could give you a stroke, and hypertension, high blood pressure, sleep apnea, senses differences in your gait if you're getting Parkinson's. All of these things from a thing on your wrist. Not in your brain, not in your heart, like on your wrist. And with FDA approval, which is so hard to get. To get FDA approval for the heart atrial fibrillation detection, they had to do a study with Stanford involving 400,000 patients. I mean, it is really hard to get approval and that they're doing it and that they have more to come. Like this thing is this watch and now the AirPods have heart detection in them. I mean, they're saving thousands of lives a year. They just are. And it's sort of a side of Apple that's crept up on us that isn't really recognized, I feel. Yeah, because that's not how they sell the devices, right? They're not selling the watch as a health device. And the fitness tracking is sort of health-related, but it's not what you're talking about here, right? It's not about, because nobody wants to think that they're going to be diagnosed with atrial fibrillation, right? If you already know you have it, Apple Watch isn't what