What Running Windows at Microsoft Taught Steven Sinofsky About Apple

0:00Theo Jaffee:I think that Steve created a culture of artists and they thought of themselves that way. And in many ways, Microsoft was a culture of technologists solving technology problems. And it led to very, very different products, but also very, very different scale, at least until the iPhone came out. People will say that the Surface hardware was the only time Apple really paid attention to something Microsoft did and that they really actually thought we had done a good job on the Surface hardware, which was quite the high praise at the time. Windows is really caught in this conundrum of the value that corporations and enterprises see in Windows is compatibility.

0:40Theo Jaffee:And the levels of compatibility that Windows has are legendary. It was just sort of speculating what would Apple be like if Steve Jobs were still running it.

0:51Steven Sinofsky:In 2007, Bill Gates sat on stage with Steve Jobs at the All Things D conference. Asked what he saw as the biggest difference between their companies, Gates looked at Jobs and said, I wish we had your taste. It was a rare concession from the most dominant technology company on earth. A decade earlier, Apple had nearly gone bankrupt. Microsoft held the PC market so completely that Apple's share had fallen below 3%. 50 years after its founding, Apple has not only survived, but reshaped entire categories of computing. From phones to watches to a$600 laptop, the PC industry cannot match. The question is how, and whether taste alone explains it.

1:37Steven Sinofsky:Stephen Stanofsky, board partner at A16Z and former president of the Windows division at Microsoft, speaks to A16Z research partner Theo Jaffe. We have a very special guest. We have Steven Sinofsky, who is a legendary software warrior in the industry. According to his LinkedIn, he's a board partner at A16Z. He wrote Hardcore Software Inside the Rise and Fall of the PC Revolution, all about his time at Microsoft, where he was at for forever, starting as a project lead in the 80s and 90s and working his way up to the president of the Windows division. And he worked there at the same time as my dad.

2:21Steven Sinofsky:So I've heard many stories about Microsoft from that era in my house. So, Stephen.

2:30Theo Jaffee:I mean, your dad dressed as Clippy at one point. So I think that that's quite the claim to fame. He's dressed up as Clippy.

2:39Steven Sinofsky:I might even have a picture of that. That would be so funny. I'll have to ask him about that later. So we're here because this week, April 2026, is the 50th anniversary of Apple. Thanks on your position in the industry over all these years, what do you think are the most important, like most salient cultural differences between Apple and Microsoft?

3:04Theo Jaffee:Well, between Apple and Microsoft, there's a very famous moment late in both Bill Gates' career and in Steve Jobs' career, where they were being interviewed on stage at a conference together. And it was the first time they'd ever been interviewed on stage, which is kind of a bookend to one of the very earliest times they were together was on an Apple PR event that was called the PC Dating Game. and there was Bill and Steve and a bunch of other original OG PC people. And they were asked all these trivia questions about the industry. And that was, I think, like in 1982 or 81, unbelievable. And then you fast forward.

3:49Theo Jaffee:I don't remember the year. I think it was about 2005 or so that they interviewed together. And it was a super touching, 2007, super touching interview by Walt Mossberg, then of the Wall Street Journal and the All Things D conference. Iconic. It was iconic. And the photos by Asa Mottet, a Silicon Valley photographer, also iconic. And one of the things that that question was actually asked about to each of them about what they saw as the differences. And Bill looked at Steve and just said, you know, I wish we had your taste. And I thought that was, I mean, it was an amazing moment. Like everybody in the audience sort of froze and only maybe 200, 300 people in the audience.

4:42But that probably is the biggest difference between the companies.

4:48Theo Jaffee:And, you know, Steve made this famous saying back when they were building the Macintosh, real artists ship, which is sort of a play on a famous Picasso thing about real artists steal. And it was actually in the movie The Pirates of Silicon Valley. And there was a famous there was a pirate flag atop the Apple building where Macintosh was originally conceived. And and I think that that Steve created a culture of artists. and they thought of themselves that way. And in many ways, Microsoft was a culture of technologists solving technology problems. And it led to very, very different products, but also very, very different scale, at least until the iPhone came out.

5:34Theo Jaffee:And I think that those two things about being artists and about the taste involved in making products are really what separated the companies. Of course, they were organized differently. you know, they hardware versus software are very different timelines. I would say the thing as an engineer that I constantly, I even talked to him about this, to Scott Forstall, who was at Apple at Next with Steve, and then the original developer on the iPhone operating system. You know, they, When Scott was working on Mac OS and porting it from next to the Mac, they went on a tear from 2000 until still today, where Mac OS was updated every single year without fail.

6:28Theo Jaffee:And sometimes it was great. Other times it wasn't great. But the fact that they released a new product every single year from the time it was OS version 10 or OS X, as some people, you know, Microsoft never pulled that off. In fact, Microsoft has had only two releases of Windows that you could even call shipped on time. Three of them out of all of them from 1983. The first one was announced in 1983 and shipped two years late in 1985. and it was all horrible. And then everyone after that was late. And it was always this waiting for Godot kind of thing. And Apple, starting in 1999, like clockwork, shipped every year.

7:10Theo Jaffee:And Scott was the champion of that. And he really, we talked about it and we talked about how nobody in the world understands how difficult that is, that two of us talking about it, because I was working on Windows and it was really that incredible accomplishment, which considering they were artists, was itself kind of an amazing thing. because you would think the artist people are the ones who can't ever figure out how to ship. Nothing's ever perfect, but it wasn't like that at all.

7:33Steven Sinofsky:So do you think this distinction still captures it 20 years after this Gates Jobs interview? Is Apple still artists and indie hacker people?

7:43Theo Jaffee:Absolutely, and I think it's probably one of the things that surprised people the most about the expectations they had for how Tim Cook would run Apple and how things ended up. I mean, I'm on this Gatorade Neo right now. And, you know, it is relatively art. And, you know, there's obviously a huge discussion going on on X right now about, you know, can there really be a PC that's$600, which is super weird because that's literally a conversation we had, you know, 12 or whatever years ago building Windows 8. And it's just, it's a fascinating thing. People thought the company would become much more mechanical, much less focused on the supply chain and things.

8:30Theo Jaffee:But it really kept, you know, you look at the iPhone X, you look at the Neo, you look at Vision Pro, you look at AirPods, you look at the watch. I mean, these are really just stunning, stunning products.

8:45Steven Sinofsky:Yeah, I agree. That's why I use them. And I'm curious, actually, what is your personal tech stack like? Like, do you just like daily drive Apple everything?

8:55Theo Jaffee:I actually, you know, it's very interesting. Yes, I do. And it bugs me. For the first few years, I really used only Surface, which is a thing that I worked on and helped, you know, release, which was the whole story into itself. But what really happened is, of course, you know, you're in a community in Silicon Valley, and most of my energy was working with founders. And so a lot of stuff, you know, shows up on the Mac first. and people share things that are sort of Mac native and things. So for a long time, I was still using Microsoft Office on the Mac, another product I worked on for a very long time.

9:31Theo Jaffee:But now, Windows is definitely in another world. And I have one machine that I keep running Windows that I do Windows-specific things on. But by and large, I sort of joined the rest of the bleeding edge of our industry on Mac. And the share numbers in the real world really show that. You know, I went through Apple getting down in 1997 to less than 3 % share of new computers sold. And then for a while, if you measured share by like laptops over$2 ,000 or something like that, you would see it be like 10 % in the U.S. and in North America. And now you're looking at 30 plus percent on the global share.

10:20Theo Jaffee:And it's just really incredible. Especially if you measure consumer versus enterprise share. You know, in the business world, they have a whole bunch of different requirements. And the PC is very much part of that. But in the home PC, like if you go to Best Buy and, you know, what their run rate is, you know, and they still serve a significant business community there. But the share number, I mean, considering it was less than 3 % when Microsoft basically rescued Apple from certain bankruptcy in 1997, right when Steve came back to the company. You know, this gradual climb, like first with the iMac and then a series of products that followed that, including the iPod, which threw people into the ecosystem, was really, really something.

11:05Theo Jaffee:And you can see that rise right there. And then, of course, in 2008, they had the MacBook Air, which was really as innovative then as the Neo is now in a similar way. It was$1 ,000. It ran Intel chips. And it was just something that the PC industry couldn't deliver. And it took three years for the PC industry to sort of respond. And it never really did. and the Neo is the response to something that was happening in 2007, 2008 in the PC world called Netbooks which were like these$400 computers that were horrible but they sold in a lot of numbers because people really wanted a cheap computer and like the Asus EPC is the original down in the middle right and they were kind of funny.

11:58Theo Jaffee:In fact, they were like a a Hail Mary project, a salvage product for Intel, where they basically made those just because they had built these phone chips that they couldn't sell to any phone maker. And so they were stuck trying to figure out how to sell these chips that were supposed to be for phones. They ran the Intel instruction set. People put Windows XP, which was the current version of Windows on it. Then Windows Vista shipped, but Windows Vista didn't run on those machines because they only had four gigabytes of storage and one gigabyte of RAM. And Vista just couldn't run. And so we had to do these emergency deals and projects to try to prevent people from shipping Vista or shipping Windows XP again.

12:39Theo Jaffee:It was a crazy time. And the Neo really, what happened was the iPad ended up being the response to that. And the iPad today sells more units than North America laptops. It's kind of a crazy success that most people in the Valley don't see as the success that it is. But it's actually very much like the watch, which is they ship the watch, but nobody knew what it was for. And then everybody discovered that it was for health. And now it has its place. It's the health device. And yeah, it does notifications and stuff, but it's really about health and fitness. And the thing with the iPad was at first people just wanted to replace their computer.

13:20Theo Jaffee:But then they found out like, oh my God, it's like point of sale. It's signage. It's for kids in the backseat. It's for airplane seats. It's for reading books, all these things that weren't even part of the original demo. And so it made a whole new market. Now the original demo was, it's all in portrait mode. And it's all about basically reading books and magazines and consumption. And so there was actually a very famous keyboard that they showed that was only useful on a desk. So it was like a docking station that had a keyboard attached. And so it's really unbelievable. I mean, that product, and of course what's fascinating is we did Surface at roughly the same time.

14:05Theo Jaffee:So you can see it only worked in portrait mode. Never seen that. It was like this weird dock. and and it was really they bought used ones for 10 bucks yeah oh they're all over ebay but it was sort of an objection handler because and i not the company just didn't believe in it and it took a long time before there was sort of a blessed you know keyboard that you could really use all the time you had the squishy keys for a long time but you know it's super interesting because we were working on porting windows to the arm processor at the same time as as they were working on the ipad and so it was a very interesting thing and it was, you know, people will say that the Circus hardware was the only time Apple really paid attention to something Microsoft did and that they really actually thought we had done a good job on the Circus hardware which was quite the high praise at the time

14:57Steven Sinofsky:So I daily drive Apple everything, I used to be like the Android kid in middle school, I was such an Android loyalist and then over time it just became inevitable, I had to have find mine. I had to have FaceTime. And so I had to switch over to all Apple. But the one Windows device I still own is my gaming PC, because you still can't really game on Macs. So like, why not? That seems like a pretty obvious market segment for Apple. And if they got that, then I can't think of anything I wouldn't use a Mac for.

15:31Theo Jaffee:Yeah, so gaming has a super interesting history at Microsoft, you know, the key technology for gaming are these graphics APIs called DirectX. And they were really the things that gave hardware access to graphics hardware on the PC. And so all the games got written to these DirectX APIs. These are the tier one, AAA, you know, FPS, those kind of games, where frame rate is everything. And part of those games are that the people who own them really want to mod and tweak every aspect of the hardware. Like they want the fastest LAN card, they want the fastest GPU, they want the most current device drivers, they want all of these things.

16:17Theo Jaffee:The Mac sort of made those pretty difficult. Like, you know, they provide most of the drivers, You know, most Macs don't have extensible graphics cards. You know, you have to buy the desktop Mac and then only certain ones work. Lots of those constraints. And so the gamer people are sort of one in the same as like modders or tuners. And so they are really into what you can do with a PC. And they sort of compete not just on the games, but on whose PC has the lowest network latency, Whose game controller can fire the fastest over wired connections and using the latest USB 3 drivers or whatever for them and stuff?

16:59Theo Jaffee:And so that's what sort of kept the game world rooted on Windows. But the problem is that a lot of the game world then moved to consoles. And of course, Microsoft and Xbox itself based on DirectX, that's actually the X. But really, the challenge there was you couldn't do the modding and everything. And then the interesting thing that really happened is the most recent, which is AI compute on the device. And so suddenly, these companion processors, like on the Mac, are the thing that everybody cares about. Now, on the PC, you have access to NVIDIA cards. Now, the most interesting thing about that is that these DirectX APIs were a competitor to the NVIDIA graphics APIs called CUDA and the whole suite of APIs around NVIDIA.

17:55Theo Jaffee:And so Microsoft and NVIDIA were kind of at loggerheads for a long time over support of each other's APIs. And that, in a sense, held Microsoft back from AI on the desktop, which is now sort of Linux or Mac-centric. And it's a very interesting, you know, from a developer perspective, Microsoft not really hosting those APIs themselves is super challenging. And that was one of the reasons we bet on NVIDIA with Surface. So when we built the first Surface for ARM was used in video chips. And that was because the graphics were so much better than anything from Intel. And so the game thing is still on PCs.

18:36Theo Jaffee:And I don't see the Macs really taking over. But it's just not, it's big, but it's not giant. And it's not growing. And where Apple has an advantage is the ecosystem of what they call casual gaming. Like all the stuff that you see people on subways and stuff playing on their phone. gargantuan amounts of performance that aren't needed for those. And any kids' games and stuff are all... Apple's ecosystem is fantastic for those. It's just those tier one AAA things that you don't really see.

19:08Steven Sinofsky:Yeah, so going back to the MacBook Neo, do you think Windows laptops are just kind of cooked now? What will they be able to do to counteract the$600 totally great general-purpose computing device that Apple just came up with?

19:26Theo Jaffee:The challenge here is that Microsoft just hasn't really made a ton of progress in the past more than decade, almost 15 years. And so that means you're really, really far behind. There's really two giant problems. One of them is that the Windows APIs themselves, Windows is really caught in this conundrum of the value that corporations and enterprises see in Windows is compatibility. And the levels of compatibility that Windows has are legendary. I mean, the only thing that comes close is our like IBM mainframes running like the 360 instruction set, which runs banks and stuff like that. But the PC, you could take a Windows 11 machine and you could run the original versions of Word and Excel from like 1990 with no problem.

20:18Theo Jaffee:And it's just insane. And you can run every device driver, all these things. And the reason enterprises like that is because they always have some weird smart card reader, some gadget, some sensor, some factory automation thing that relies on that compatibility. But that compatibility also means you're vulnerable to security problems, you're vulnerable to fragility and conflicts between devices, and you're just broadly insecure and have really bad battery life because all those things run in kernel mode. It's just a mess. What Apple has been doing in those year releases that I talked about earlier, they've been basically saying these APIs don't exist anymore and you have to use these new ones.

21:00Theo Jaffee:And they do that, and they're on this continual renewal where they just obsolete things. And that really ran against everything that was about Windows. And so that's one big problem. So even if you have Windows, the APIs and the apps, all that compatibility just will make it a non-competitive device with Neo. And that's what you get on Windows on ARM today. Like, you don't have any of the benefits. It's not more secure. It's not more reliable. It's not faster. It's not cleaner. It doesn't get the battery life, the power management. The other side of it is the OEM model. And that means the model where you have multiple vendors making PCs really works against having high quality and low price.

21:47Theo Jaffee:And you can see that they really want to do either low quality and low price or different levels of quality at higher prices. See, this device, it's just non-competitive. First, 8 gig on a PC is really marginable. The AMD chipset, you're going to get, you know, what is that? That machine's going to get like four hours of battery life, five hours. I don't know what Best Buy says, but that's about four or five hours of battery life. Plus, all the viruses, everything run on it. So like every piece of malware in the history of malware runs nine hours. Not a chance it gets nine hours. No way. I mean even the Neo 9 hours is pushing it and so and also it has a fan and it's super loud and it's made of plastic so you drop it once and it's doomed all of these things are problematic and the 10 ADP speed yeah and it weighs a ton does it go down to the weight and the physical spec yeah 3.5 pounds that's a tank and and so almost a pound heavier than the yeah yeah than the neo and so the the pc model just it doesn't lend itself to that they they have to build it because the reason is is because they're all buying the parts from the same place like the brilliance of the neo is it's one of a chip that's that it's oh god now well it's a phone book so it's 80 cheaper that's but the the neo the The beauty of it, of course, is it's running a phone chip that's been paid for 100 ,000 times over by the sales of all the phones.

23:34Theo Jaffee:So there's not even any what you call NRE, non-recurring engineering costs, baked into the Neo. It's really just paid for. It's like literally the actual physical marginal cost to produce another A18 chip, which is almost nothing. and so it's a very very tough compete all of this was obvious in 2007 with netbooks it was obvious when we built surface i had a giant two giant blog posts one from 2011 and one that i wrote a when the neo came out about it and it it's really um it's it's really interesting so also in in new

24:16Steven Sinofsky:Apple products, we have the Apple Vision Pro, the infamous Apple Vision Pro, which has, I actually used to have one. I didn't pay for it. It was a school club. I was not going to spend$3 ,500 on that when I was in college. It was very cool, but it was kind of useless and I ended up not really using it. It didn't sell as much as people anticipated. The chat is asking, did I get emotions sick um and no i didn't luckily i also had to wear contacts because it didn't work with bosses so what's going on with this is this uh well this is a big failure is it salvageable i

24:54Theo Jaffee:this is why i saw someone on x say something that i i really hate to agree with because it's such a kind of a weird creepy kind of discussion but it was just sort of speculating what would apple be like if Steve Jobs were still running it. And one of the things that was on the bullet list was that they would have been crushing it with AR glasses as opposed to VR goggles. And I have to say, the one thing I would say about AVP is it has this feel of like, it was a huge risk to put it out there. Apple putting a risky product out is such a big deal. But also, you had to sort of go, maybe they were just, they didn't quite know where it was going, and they just didn't need to take the risk.