(Preview) Five Questions on Apple at 50 Years Old, The Axios Hack and AI Security, Q&A on Starlink, AI IPOs, AirPods
- Apple’s most important decision was acquiring NeXT and bringing Steve Jobs back, not releasing iTunes for Windows. Ben calls the iTunes argument defensible but wrong. Andrew says his own view is not high-conviction, but his Windows experience made iTunes an Apple on-ramp and suggests its absence could have complicated later iPhone adoption.
- Ben’s primary answer on Jobs’s leadership flaw is his extreme indifference to people close to him, which he sees as inseparable from Apple’s product standards. He also relays John Gruber’s technical critique that Jobs’s drive to control everything went too far. Jobs 2.0 partly contained his destructive tendencies through organizational layers, while some of Apple’s best decisions, including Windows iTunes and the App Store, emerged through internal defiance before Jobs came around.
- The original iPhone commercials were Apple’s strongest ads because demonstration, education, and persuasion were the same act. A phone and finger showed “This is the web…this is email…this is a call,” simultaneously revealing an unprecedented product and teaching customers how to use it.
- Apple’s current software friction now resembles what its old advertising mocked Windows for doing. Ben points to a headless Mac that can stop working until someone logs into the GUI to handle a network-storage modal; both hosts ridicule notifications, including Apple TV announcing “Hey, close game” while the viewer is already watching.
- China was critical to Apple’s eventual scale, though the counterfactual remains uncertain. Apple followed competitors there rather than leading the migration, then mastered the system. Ben says Apple might have been relatively better off without the industry-wide move, but leaves open whether it could have matched its speed, volume, prices, or dominance.
- Microsoft ranks first and Apple second on Ben’s technology Mount Rushmore because Microsoft created the first real platform. Andrew challenges whether Microsoft must qualify, but Ben is categorical: understanding its consumer and enterprise successes, as well as its consumer failures, is “the key to understanding technology, period.”
1. Bringing Jobs back mattered more than opening iTunes to Windows
Ben’s immediate answer: acquiring NeXT and getting Steve Jobs back. He calls the Windows-iTunes argument defensible but ultimately wrong; Andrew—not Ben—adds that without Jobs returning, Apple was “dead in the water.”
Andrew says his own argument is not high-conviction, but his experience illustrates the adoption effect: an early iPod was irrelevant to a Windows user until iTunes crossed platforms. He argues that this became an Apple on-ramp for many people and that, without it, later iPhone adoption could have been more difficult.
Ben concedes the strategic symbolism. Windows iTunes was a defensible marker of Apple’s break from being merely a Mac company, later formalized when Apple Computer became Apple at the iPhone event.
2. Jobs’s cruelty and product empathy were two sides of one system
Ben’s primary framing: nobody understood or “had empathy for humanity” like Jobs, even though he did not care about people close to him, including colleagues and family. Apple built technology for “the rest of us,” but the leader enforcing that standard could be “kind of a psychopath.”
Jony Ive once told Apple interns that caring about colleagues’ feelings can be selfish: people avoid honest criticism because they fear making others angry. Ben’s uncomfortable conclusion is that maintaining Apple-level quality requires an unusual willingness to upset internal stakeholders.
Jobs 2.0 improved by building systems and hierarchies that “protect everyone else from himself.” Ben also relays John Gruber’s technical critique: Jobs went too far in trying to control everything, initially opposing Windows iTunes and the App Store. Those decisions advanced through others’ defiance before Jobs came around and effectively treated the outcomes as his idea.
3. Apple’s best advertising made the product teach itself
Ben rejects the expected “Think Different” answer for the original iPhone campaign: one phone and one finger demonstrated browsing, email, and calls. The ads were “simultaneously mind-blowing” product showcases and tutorials—“perfect ads” that accomplished several jobs at once.
Andrew retains the emotional case for “Here’s to the Crazy Ones” and the Christmas commercial in which a teenager films his family. The hosts also call the iPad crushing ad an accidental classic when played backward, expanding the tablet into music, art, and instruments.
Their personal reactions were less tidy. Ben is pretty sure he recognized the iPhone’s significance but cannot genuinely remember the moment; his first device was an iPod Touch. Andrew remained “a BlackBerry guy through and through” for three and a half years, switching only when the iPhone became “eons better.”
4. Apple’s current software friction now resembles its old Windows critique
Ben nominates an old Mac-versus-PC commercial mocking Windows Vista pop-ups as the ad Apple executives should now watch: “Look, this is where we ended up.” Modern Macs have accumulated the interruptions Apple once used against Microsoft.
Ben says he will not buy another Mac to run headless because it can stop functioning until someone logs into the GUI and approves a modal asking whether it may access network storage—“Of course I do. That’s why you’re a headless Mac.”
Andrew targets notification overload, including Apple TV baseball-score alerts. Ben adds the absurd example of a “Hey, close game” alert appearing while the viewer is already watching the game. The examples contrast with the older ad’s critique of Windows pop-ups.
5. China supplied scale, while Microsoft supplied tech’s governing model
Ben treats a China-free Apple as an “almost impossible counterfactual.” Apple was late to China: Steve Jobs was committed to American manufacturing, with plants Ben believes were in Fremont and, he thinks, Texas, plus one in Cork, Ireland. Apple eventually mastered China, which became critical to producing iPods and iPhones at scale.
Ben says Apple might have been relatively better off without the industry-wide move to China, but leaves open whether it could have produced those products at comparable speed and volume or achieved comparable prices and dominance.
Apple’s factory problems also reflected premature automation, similar to Tesla’s Model 3 difficulties. Ben wonders whether pressure to manufacture hundreds of millions of iPhones in the US might instead have pushed American automation much further.
On technology’s Mount Rushmore, Ben ranks Microsoft first and Apple second. Microsoft bridged consumer and enterprise computing and established the platform model—ecosystems, developers, and related network effects—which he calls “the most important concept in technology.” The preview ends before the remaining two selections.
Full transcript
Hello, and welcome to a free preview of Sharp Tech. Hello, and welcome back to another episode of Sharp Tech. I'm Andrew Sharp, and on the other line, Ben Thompson. Ben, how you doing?
Doing good, Andrew. Feeling young.
Are you? Why?
Well, we’re talking about a 50-year-old today—someone who preceded me in birth. A welcome change of pace from most of our tech discussions.
That’s right. One of the few companies whose lifespan you have not witnessed from beginning to end here. So yes, that’s where we’re going to begin. In honor of Apple’s 50th anniversary, I wanted to put together a couple of rapid-fire questions at the top. You wrote about a big question.
Before you get to this, this was such a good idea.
Questions for you.
I have to be honest: I blatantly stole these questions and used them on Dithering. I did not give my answers on Dithering, though. So listen to that to hear John Gruber’s answers.
Okay.
I kind of cheated because 2 of them we completely agreed on, and 1 of them we mostly agreed on. Actually, I’m going to steal John Gruber’s answer on 1 of them, to be honest, because he had a better answer than I did. But there are at least 2 of them that are going to be fresh to this podcast. So there you go.
I love it. I love it. Well, it’s going to be rewarding for the bundle listeners, the real dedicated bundle listeners.
That’s right.
They can compare your answers. They can compare Gruber’s answers. So it’s all part of the fun here at Stratechery. Number 1 on my list of questions for you: Was putting iTunes on Windows the most important decision in the history of the company? What do you think?
No. The most important decision in the history of the company was acquiring NeXT and getting Steve Jobs back.
Bringing Jobs back. Okay. Fair enough.
Yes. Needless to say, this is 1 where John Gruber and I had the exact same answer and the exact same level of immediacy.
Okay.
It’s a good take. I think you could construct a take around iTunes on Windows being the most important decision in the history of the company, sort of breaking out. It was sort of symbolized by and made formal at the iPhone event, when, at the end of the event, they changed the name from Apple Computer to just Apple. That spoke to what this decision precipitated: We’re not just about the Mac.
Yeah.
It’s a good take. I could probably say yes and make an argument for it. It would be wrong, though.
And to be honest with you, it’s not a high-conviction take from me. I’m just drawing on my own personal experience with Apple because I dated a girl in high school who was from a Mac family. Everybody used Macs over at her house, and she had an iPod very early on. I think she had the first version ever—the brick iPod, back in the day.
With the actual—
And it was cool—exactly, with the wheel. It was really cool technology, but also completely irrelevant to me because it only ever worked with her Mac. My first experience using Mac software outside of elementary school computers was when they put iTunes on Windows, and I bought an iPod. I don’t think the iPod is ever nearly as popular without that change, and that then complicates iPhone adoption later in the decade. It was the on-ramp for a lot of people, or at least it was the on-ramp for me.
Yeah.
So I’m drawing on my own experience there.
No, it’s a good take. It’s a good take. It is wrong, but it is the best take that is defensible and will inspire everyone to get upset about it because it’s wrong, so it’s good.
Right. And Steve Jobs—without Steve Jobs coming back, they’re just dead in the water.
1. Steve Jobs Leadership Flaws
Related to Steve Jobs, what were Steve Jobs’ flaws as a leader? I ask that because there are 25 tech-motivation accounts on Twitter that do nothing but post quotes and interviews with Steve Jobs. I love those accounts, but that’s really the extent of my exposure to him.
Because the quotes and interviews are all really good.
They’re awesome. They’re awesome. So don’t stop, tech influencers. But it does make me wonder: What were the downsides? What were the blind spots? I know he was insane as a boss, but if you had to pinpoint anything, where would you go?
Well, this is interesting. My initial thought here, at the risk of even coming somewhat adjacent to culture-war content—
Oh, boy.
Yeah, well, there’s that meme illustration thing of heat maps of conservatives versus liberals—caring about people close to you versus caring about people far away, or whatever it is. I don’t even know what it is. I try to steer clear of all that stuff.
I’ve seen the culture-war heat maps related to AI, so sure. There are all sorts of different attitudes about everything.
Well, I think the way to think about Steve Jobs is that no one understood and had empathy for humanity like Steve Jobs, to the extent that he didn’t give a single flying fuck about anyone close to him.
Ah.
He was the extreme version of this. Managing Apple—the most empathetic company in tech, the intersection of liberal arts and technology, right? We’re creating computers for the rest of us—
Totally.
They did it at scale. They felt for humanity, and Steve Jobs felt for humanity to such an extreme degree that he did not care about anyone close to him—not just at the Apple level or the executive level, but down to the family-member level. This guy is kind of a psychopath.
Mm-hmm.
But this is a bit of the interview question, “What’s your biggest flaw?” “I care too much.” That’s kind of what you need to deliver the quality Apple delivers, at the scale Apple delivers it, for the length of time they’ve done so. You could critique the post-Steve Jobs era of Apple for actually caring a little too much about internal stakeholders and people’s feelings, and not actually keeping up the standards necessary to deliver the quality of products for everyone.
I’ve talked about that Jony Ive talk that I got when I was an intern there—not me personally; all the interns got all the executives to speak to them. His whole thing in this talk was that the most selfish thing people do is care about other people’s feelings.
Mm.
They’re not honest because they don’t want other people to be mad at them. If you want to make great products—
Yep.
Basically, he was saying you need to be a psychopath. You need to be like Steve Jobs. That is really hard to maintain, and it’s really important for delivering consistent quality over time.
For sure, if you talk to anyone about Steve Jobs’ flaws, that’s where they go. They will point to the family. They will point to the way he dealt with people. I do think 1 of the great things he learned with Steve Jobs 2.0, when he came back to Apple, is that he constructed systems and hierarchies within Apple to protect everyone else from himself. Whereas before, he was this loose cannon taking shots at everyone, from top to bottom.
He sort of knew there’s an aspect of himself that’s not suitable to managing humans.
That’s bad and toxic.
Yes, exactly. I think that was a key thing to his success in 2.0. Again, it’s kind of a cheating answer because I’m saying the flaw is exactly why he was great. But you could say—
That’s okay. I saw an interview with Steve Jobs posted this week where he was asked about his weaknesses. It inspired the question, and Steve Jobs basically completely sidesteps the question and spends the entire answer talking about his strengths and how important his strengths are.
Well, but strengths are—
So—
Strengths are weaknesses. That is always the case.
Well, that’s what he said.
And—
He said, ultimately, it’s indivisible with any human.
That’s right.
And that’s where—
What a smart guy. Yeah. So—
So you and Steve Jobs are aligned 100%. It sounds to me like that’s almost more of a personal failing than a strategic or business failing—
Right. No, exactly.
On Steve Jobs’ part.
So it’s totally cheating on the answer. I think if you want to get technical, John’s answer was about Steve Jobs going too far in terms of Apple controlling everything. So he talked about—
Okay.
How Steve Jobs was opposed to the App Store, for example. iTunes on Windows is another good example. Steve Jobs was completely opposed to that. And if you go to some of Apple’s worst tendencies, they’re downstream from the way Steve Jobs wanted—
Control-freak Steve Jobs.
— to control everything, right?
Yeah.
But again, it sort of speaks to his strength in that he definitely went too far.
Mm-hmm.
Steve Jobs in a political context would have been the guy who said, “Let’s just control everything.” Central planning for the win. But—
Yeah.
He allowed himself to be wrong. He allowed himself to be overruled in certain cases.
I was going to say—
So—
It seemed like Steve Jobs 2.0 was more comfortable pivoting off some of those positions and making decisions in the best interests of the company.
Yeah. The iTunes on Windows example you had is a great example. Some of Apple’s best decisions, like that—like the App Store—were actually made by people in defiance of Steve Jobs until he comes around and says... Then it was sort of his idea.
Perfect. Any great leader has that quality. Number 3: What’s your favorite Apple ad of all time? What do you have for me?
Oh, this is where I definitely kick Gruber’s rear end. Of course he picked, “Well, I guess Think Different.” No, no, come on. Get out of here. The obvious answer—the clear answer, the no-question answer—is the original set of iPhone ads, where all it did was show an iPhone and a finger.
Okay.
This is the web. This is email. This is a call. It was simultaneously mind-blowing because you’d never seen a phone that could do this sort of stuff. So it was a great advertisement to show what the phone was, and Apple was also teaching people how to use it at the exact same time. The entire set was just such a brilliant concept that accomplished so many things at the same time. It was just a perfect set of ads. It can’t be beat.
So if you were to transport yourself back to 2007, when all of this was launched, do you remember how you reacted to the iPhone keynote? In the interview this week, Horace Dediu is talking about the reaction at Nokia. Obviously, the BlackBerry movie depicts the BlackBerry reaction, and it’s pretty hilarious in retrospect. But how did you react in the moment?
Well, yeah, the interview with Horace Dediu was a lot of fun this week, particularly a lot of the historical stuff. Also, we mentioned the BlackBerry movie. Great movie. I think it’s on Netflix now. Is that why people are talking about it?
It was fantastic.
It’s a great story, by the way.
Yes. It’s a great hour and 45 minutes.
It’s been a great movie for ages, but of course—
Yeah.
No one realizes it exists until it’s on Netflix.
It’s a good point.
But no, it’s a great movie. It’s really good. It’s mostly historically accurate. It certainly captures the sense of the time. I highly endorse the BlackBerry movie.
Did you get the iPhone in the moment? Were you swept away the second they announced it?
It’s a good question. I’m pretty sure I was, but it’s—
Okay.
It’s not super crystallized in my head.
Mm-hmm.
I don’t know. That was the peak of being fully native in Taiwan and hanging out.
Yeah.
I wasn’t working in tech. But it’s hard to imagine I wasn’t. Given the time and how many times I’ve watched the keynote, I don’t remember the moment of watching the keynote. Whereas there’s lots of stuff in my life where I have very semantically rich memories that way. I can picture where I was and everything that was going on.
Yeah. Time and place.
I don’t remember that for the iPhone. It’s actually a really good question. I’m sure I was. I helped my brother-in-law smuggle in a jailbroken iPhone to Taiwan.
Oh, wow.
I personally got an iPod Touch. That was my first device, but—
Yeah.
—it’s a good question. I can’t remember.
Interesting, yeah. Well, I didn’t pay attention to iPhones, to the surprise of nobody who’s been listening to this podcast for the last 3 years. It took me 3½ years before I took the iPhone seriously. I was a BlackBerry guy through and through until the bitter end, when the iPhone was just eons better than the BlackBerry and I finally shifted over.
My favorite ad is ultimately a normie answer along the lines of Gruber: “Here’s to the crazy ones.” I watched that last night. Part of the Think Different campaign. Just an incredible piece of advertising. Ben’s yawning here. Goddammit. There’s also the iPhone commercial where the teenager films his family at Christmas.
Oh, that’s a good one.
Watched that last night—
That is an all-timer.
—as well.
That’s a great one.
May have started to tear up.
Yep.
All part of the adventure. I also want to nominate—
What about the squishing creatives with the iPad?
Well, I was going to mention that. The industrial crushing machine crushing paint and pianos and instruments—
Accidentally an all-time ad.
—and everything else.
Not for all the reasons they intended.
Well, and remember the parody afterward where they just reversed the ad, and it takes the iPad, and suddenly you see this expansive universe of music and art and everything else?
Not a parody. Literally just playing the ad backwards.
And that’s actually a great ad. So it deserves mention in this conversation. That’s what the iPad makes possible.
I was also, cheekily, going to nominate—you had the “I’m a Mac” and “I’m a PC,” a very famous set of ads.
Mm-hmm.
But there was one—one of the more famous ones—where they made fun of all the pop-up warnings from Windows Vista and how annoying Windows Vista was compared to a Mac.
Yeah.
I just want to mention it because the Mac’s really freaking annoying with all the pop-ups and all the stuff that you have to deal with today. I would like to shove that ad in front of Apple executives’ eyeballs and say, “Look, this is where we ended up.”
Remember when you knew what people wanted?
Can we have Steve Jobs, totalitarian Steve Jobs, being mean to everybody? And that was him. Look at you.
Oh my God, it is pretty bad. The notifications. I just want to turn every single notification off on my—
No, it’s a problem.
—Apple devices.
I will never buy a Mac to run headless again—
Yeah.
—because stuff just stops working because you have to actually log in to the GUI to see this stupid modal pop-up that asks, “Do you want to access network storage?” Of course I do. That’s why you’re a headless Mac. Ugh.
It’s terrible. And you have to go through app by app and shut off notifications individually.
No, no. You're missing it. I'm not talking about the notifications in the corner of the screen.
No, no. I'm talking about—
The notifications.
Okay. Well, fine.
It's really annoying to me.
Okay.
Apple TV—I never need a notification about baseball scores.
When you're watching a game, it pops up, “Hey, close game.” It's like, “Yeah, I know.”
Oh, my God.
“I'm literally watching on the screen right now.”
It's horrible, man.
Yes.
I've had enough. Number 4 on the list: If Chinese manufacturing never arrives in the 1990s, are we still using Apple products today? What do you think?
This is another one where John and I had the same answer. It's kind of an almost impossible counterfactual.
Mm-hmm.
The reality is Apple actually might have been, relatively speaking, better off.
Okay.
Apple had to go to China because everyone else had gone to China. They were not the first ones there. They were the last ones there.
Mm-hmm.
Steve Jobs in particular was super committed to American manufacturing. They had plants, I believe, in Fremont. They had one—
Fremont.
I think in Texas.
Yeah.
They had one in Cork, Ireland. So they were late to China. Would they have the scale that they do? Would the prices be, relatively speaking, as low as they are? Those are all very, very good questions. Would Apple be as dominant as they are? They were late to China, but they mastered China.
Right.
The whole bit about doing what they do at scale—China is a critical part of that.
That's the piece of it. If I go back to Apple in China by Patrick McGee, my understanding was that the expertise they were able to cultivate in China allowed them to scale products like the iMac, which was a big part of providing the business.
I think the iMac could have survived. I think the iMac originally might have been made in the US. It's really stuff like the iPod and the iPhone.
Mm-hmm.
When we're talking about hundreds of millions of units and the speed and scale, would that have been possible? It's almost an impossible counterfactual.
They were super aggressive in terms of automating factories. That's part of the reason they had so many problems with their factories: they were trying to build them too far in the future. This is very much a Steve Jobs–Elon Musk comparison point.
Mm-hmm.
Tesla really almost got in big trouble trying to get the Model 3 out the door. They pre-automated too many things, and they had to backtrack. You have to get stuff working, then you automate it.
Yeah.
Apple made all the exact same mistakes with the Mac in the early days.
Yeah.
At the same time, Tesla is a great hope for manufacturing in the US.
Mm-hmm.
Maybe the US would be much further ahead, particularly in terms of automation, if there was market pressure to make hundreds of millions of iPhones in the US. Again, it's almost an impossible counterfactual, but it is an interesting question to think about for all those reasons.
Yeah. So much of the progress that we saw from Apple over the last 25 years was downstream of the processes they developed in China. It would be really cool if all of that had happened in the US, but would any of those products have been affordable in that scenario? A good question.
2. Technology's Mount Rushmore
Number 5 here: If we had a tech-company Mount Rushmore, Apple is obviously on there in my eyes, but who gets the other 3 spots, do you think?
I'll start with this: it's the one I stole from John Gruber.
Okay.
The obvious next choice is Microsoft. Apple and Microsoft are the top 2, historically speaking.
Do they have to be, though?
Yes, absolutely.
Come on.
No, there's no question. You saw this in the discussion with Horace. Understanding Microsoft has been the key to understanding technology, period—both consumer and enterprise.
Okay.
They're probably the only company that bridges both: understanding how you win in the consumer space, how you win in the enterprise space, and how you lose in the consumer space.
Yeah.
The importance of that is that they are the ones that instituted the concept of a platform. It was the first real platform, and platforms are the most important concept in technology—in ecosystems, developers, and all these sorts of things. Microsoft is number 1.
Wow.
Apple's number 2. The concept of a platform is the most important concept in technology, and Microsoft was the first platform.
All right, and that is the end of the free preview. If you'd like to hear more from Ben and I, there are links to subscribe in the show notes, or you can also go to sharptech.fm. Either option will get you access to a personalized feed that has all the shows we do every week, plus lots more great content from Stratechery and the Stratechery Plus bundle. Check it out, and if you've got feedback, please email us at email@sharptech.fm.