What Running Windows at Microsoft Taught Steven Sinofsky About Apple

Theo Jaffee speaks with Steven Sinofsky, board partner at a16z and former president of the Windows division at Microsoft, about Apple's 50th anniversary, the cultural differences that separated Apple and Microsoft, why the MacBook Neo puts Windows laptops in a difficult position, and what the history of computing design reveals about where hardware and software are headed.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Steven Sinofsky?

  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. And the levels of compatibility that Windows has are legendary.

• 0:44Steven Sinofsky?

  It was just sort of speculating, what would Apple be like if Steve Jobs were still running it?

• 0:51Erik Torenberg?

  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.

• 1:33Erik Torenberg?

  The question is how and whether taste alone explains it. Steven Sinofsky, board partner at A16Z and former president of the Windows division at Microsoft, speaks to A16Z research partner, Theo Jaffe.

• 1:50Speaker 02

  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. So I've heard many stories about... I've heard many stories about Microsoft from that era in my house. So Stephen.

• 2:30Steven Sinofsky?

  I mean, your dad dressed as Clippy at one point. So I think that that's that's quite the claim to fame.

• 2:37Speaker 02

  He's dressed up as Clippy.

• 2:39Steven Sinofsky?

  I might even have a picture of that.

• 2:41Speaker 02

  That would be so funny. I'll have to ask him about that later.

• 2:46Speaker 02

  So we're here because this week, April 2026, is the 50th anniversary of Apple. Based on your position in the industry over all these years, what do you think are the most important, like most salient and cultural differences between Apple and Microsoft?

• 3:05Steven Sinofsky?

  Well, between Apple and Microsoft, you know, there's a very famous moment

• 3:11Steven Sinofsky?

  late in both Bill Gates' career and Steve Jobs' career, where they were being interviewed onstage at a conference together. And it was the first time they'd ever been interviewed onstage, 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. I don't remember the year. I think it was about 2005 or so

• 3:53Steven Sinofsky?

  that 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.

• 4:05Speaker 02

  Iconic.

• 4:07Steven Sinofsky?

  It was iconic. And the photos by Asamata, a Silicon Valley photographer, are 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, Bill looked at Steve and just said, you know, I wish, I wish we had your taste.

• 4:33Steven Sinofsky?

  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. And, uh, but that probably is the, the biggest difference between the companies. 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, uh, real artists steal. And it was actually in the movie, The Pirates of Silicon Valley. Um, and there's a famous, there was a pirate flag atop the Apple building where Macintosh was originally conceived.

• 5:13Steven Sinofsky?

  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. And, and I think that those are, 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

• 5:57Steven Sinofsky?

  this, to Scott Forstall, who was at Apple at NeXT with Steve and then, uh, the original developer on the iPhone, um, operating system. You know, they, when they, when, when Scott was working on macOS and porting it from NeXT to the Mac, they went on a tear from 2000 until still today, where macOS was updated every single year without fail. 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 OSX, as some people, you know.

• 6:42Steven Sinofsky?

  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 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 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, you know, it was really that incredible accomplishment, which considering they were artists, was itself

• 7:26Steven Sinofsky?

  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.

• 7:34Speaker 02

  So do you think this distinction still captures it 20 years after this Gates-Jobs interview? Are, is Apple still artists and indie hacker people?

• 7:43Steven Sinofsky?

  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, would run Apple and, and how things ended up. I mean, I'm on, I'm on this Gatorade Neo right now and, you know, it is relatively art. And, 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 $600, which is super weird, because that's literally a conversation we had, you know, 12 or whatever years ago, building Windows 8 and, and it, it, it's just, it's a fascinating thing. People thought the company would become much more mechanical,

• 8:27Steven Sinofsky?

  much less focused on the supply chain and things, but it, 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.

• 8:45Speaker 02

  Yeah, I agree. That's why I use them. And I'm curious, actually, what is your personal tech stack like? Do you just like daily drive Apple everything?

• 8:55Steven Sinofsky?

  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 a whole story in 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, was, 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 using, still using Microsoft Office on the Mac, another product I worked on for a very long time. But, but now, you know, like, Windows is definitely in another world.

• 9:37Steven Sinofsky?

  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 lived 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, like 10% in the US and in North America. And now you're looking at 30 plus percent on the global share. And it's just really incredible.

• 10:23Steven Sinofsky?

  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, you're, and that, and they still sort of have 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.

• 10:55Steven Sinofsky?

  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 was really, really something and you can see that rise right there. And then, of course, in 2008, they 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 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. Um, and the Neo is a response to something that was happening in 2007, 2008 in the PC world called Netbooks,

• 11:39Steven Sinofsky?

  which were like these $400 computers that were horrible, but they sold in a lot of a lot of numbers because people really wanted a cheap computer. And like the Asus EPC is the original down in the in the middle right. And and, you know, they were they were kind of funny. In fact, they they were like a hail Marys 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. Um, 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.

• 12:22Steven Sinofsky?

  Then Windows Vista shipped, but Windows Vista didn't run on those machines because they only had four gigabytes of storage and and 1 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. 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 all more units than 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 the watch, which is they ship the watch, but nobody knew what it was for. And then everybody discovered that it was for health.

• 13:07Steven Sinofsky?

  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 the thing with the iPad was, at first, people just wanted it to replace their computer. 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 in portrait mode. And it's all about basically reading books and magazines and and consumption. And so it's, you know, there was actually a very famous keyboard that they showed that was only

• 13:51Steven Sinofsky?

  useful on a desk. So it was like a docking station that had a keyboard attached. And and so it's really unbelievable. I mean, that product and of course, what's fascinating is what's, you know, we did Surface at the roughly the same time. So you can see it only worked in portrait mode.

• 14:08Speaker 02

  Never seen that.

• 14:09Steven Sinofsky?

  It was like this, this weird dock. And and it was really they just did it as.

• 14:14Speaker 02

  Bought new ones for 10 bucks.

• 14:16Steven Sinofsky?

  Yeah, oh, they're all over eBay. But it was sort of an objection handler because and 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 know, 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 and so it was a very interesting thing. And it was, you know, 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 the Surface hardware, which was quite the high praise at the time.

• 14:58Speaker 02

  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 My, I had to have FaceTime. And so I had to switch over to all Apple. But the one Windows device that 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.

• 15:32Steven Sinofsky?

  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 and where framerate is everything. And part of those games are that the people who own the 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.

• 16:17Steven Sinofsky?

  The Mac sort of made those pretty difficult. Like you, 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, 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, who's, you know, whose game controller can fire the fastest over wired connections and using the latest USB 3 drivers or whatever for the, and stuff.

• 16:59Steven Sinofsky?

  And so that's what sort of kept the game world rooted on Windows. But the problem is, 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, but really the, the, the, 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, which is AI compute on the device. And so suddenly, these companion processors, like on, on the Mac, are, are the thing that everybody cares about. Now, on the PC, you have access to Nvidia cards.

• 17:43Steven Sinofsky?

  Now, the most interesting thing about that is that these DirectX APIs were a competitor to the Nvidia graphics APIs and called CUDA and the whole suite of APIs around Nvidia. 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, 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, 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 using, used Nvidia chips.

• 18:29Steven Sinofsky?

  And that was because the graphics were so much better than anything from Intel. And so, the game thing is still on, on PCs, and I don't see the Macs really taking over, but it's just not, it's a, it's big, but it's, 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, and any kids' games and stuff are all, you know, Apple's ecosystem is fantastic for those. It's just those tier-one AAA things that, that you don't really see.

• 19:08Speaker 02

  Yeah, so going back to the MacBook Neo, uh, do you think Windows laptops are just kind of cooked now? Like, but what will they be able to do to counteract the $600, uh, totally great general purpose computing device that Apple just came up with?

• 19:26Steven Sinofsky?

  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 only 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 know, you could

• 20:07Steven Sinofsky?

  take, you know, a Windows 11 machine and you could run the original versions of Word and Excel from like 1990 with no problem. 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

• 20:52Steven Sinofsky?

  releases that I talked about earlier, they've been like basically saying, these APIs don't exist anymore, and you have to use these new ones. 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's just, they don't get the battery life, the power management. The other

• 21:34Steven Sinofsky?

  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. 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, like this is, this, this device is just non-competitive. First eight gig on a PC is, is really marginable. The AMD chipset, you're gonna get, you know, what is that? That shit, that machine's gonna get like four hours of battery life, five hours. I don't know what they Best Buy says, but that's about four or five hours of, of battery life.

• 22:19Steven Sinofsky?

  Plus, all the viruses, everything run on it. So like every piece of malware in the history of malware run nine, not a chance it gets nine hours. No way. I mean, even the Neo, nine hours is pushing it. And so, and so that, 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, it's doomed. All of these things are problematic and, and the. Tiny PC screen. Yeah. So. It's worse than. No, and it weighs a ton. It like, what is it? Does it go down to the weight and the physical spec? I mean, cause it's gonna, yeah, three and a half pounds. Like that's a, a tank. And, and so. Almost a pound heavier than the. Yeah, yeah. Than the Neo.

• 23:03Steven Sinofsky?

  And so the, the PC model, it just, it doesn't lend itself to that. They, they have to build it. Cause the reason is, is because they're all buying the parts from the same place. Like the, the brilliance of the Neo is it's running a chip that's. That it's, it, oh God, no, well, it's a phone book. So it's $80 cheaper. That's, but, but the, the Neo, the, the beauty of it, of course, is it's running a, a phone chip that's been paid for 100,000 times over by the sales of all the phones. So there's not even any what you call, uh, MRE, non-recurring engineering costs baked into the Neo. It, it's really just paid for.

• 23:44Steven Sinofsky?

  It's like all, it's like literally the, the actual physical marginal cost to produce another, you know, A18 chip, which is almost nothing.

• 23:54Steven Sinofsky?

  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 when the Neo came out about it. And it's really, it's really interesting.

• 24:15Speaker 02

  So also in new 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 motion sick? And no, I didn't, luckily. I also had to work contacts because it didn't work with bosses. So what's going on with this? Is this, is this a big failure? Is this salvageable?

• 24:53Steven Sinofsky?

  I, this is what I saw someone on X say something that 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, with AR glasses as opposed to VR goggles. And I have to say, the one thing I would say about ADP is it has this feel of like, it was a huge risk to put it out there. You know, Apple putting a risky product out is such a big deal. But also you had to sort of go, maybe they, they were just, they, they, they didn't quite know where it was going

• 25:37Steven Sinofsky?

  and they just didn't need to take the risk. And if they would have waited a year, they would have done AR glasses. And those, I'm positive they could really nail. And so that's, I think, I have them and, you know, I took them on a trip to Tokyo and I walked around. I put, I wore them on the plane. I watched all the movies on the plane with them. I walked around the Tokyo Metro Station, made videos, spatial videos of the subway. They were incredible. I mean, the technology was.

• 26:10Steven Sinofsky?

  And reporting the videos was just, it was just unbelievable. But there's only so many things to do like that. You know, and it felt, it had that feel that frankly VR has always had. You know, a good friend of mine was the originator of VR, Jaron Lanier, way, way back in the, in the early 1980s. And it's always sort of been this technology searching for, you know, the use case that really works. And of course it had a lot of uses back in the early eighties. You know, the, the air force and pilots were using it for training in the military and it was a huge deal. I once did like a, a thing just to make some cash at school, where like the mechanical engineering department was testing out like the interiors of tanks. And part of it was they gave you these crazy VR goggles

• 26:55Steven Sinofsky?

  to pretend you were driving a tank so that they could just measure you in the seat. And I was like the right height for a tank commander. And I got like $6 an hour to pretend to drive a tank.

• 27:06Speaker 02

  That's, that's pretty cool. Uh, final question. Uh, you helped oversee the development of Windows 7, which was not only my favorite version of Windows ever, but was probably my favorite design of any OS ever, with the whole like, uh, Windows Aero vibe, the skeuomorphism and the glass and the transparency. So like, why, why did we ever move away from that towards the like sort of flat minimalism? And are we coming back to it?

• 27:37Steven Sinofsky?

  Well, the, you know, everything with graphics goes in these cycles where, where, you know, something is new, a bunch of people criticize it when it's new. And, and then, then you, you like it and then it gets a little tired. And then people criticize you when you move away from it. And then people get nostalgic and you return. And I, I think we'll, we'll see a return. I mean, Apple certainly drove a return to some transparency, some rounded corners and, and things like that. I think that it's really important. The most interesting reason, going back to DirectX, why Microsoft deduced Aero first with, with, um, with Vista and Windows 7 and stuff was, it was because DirectX was built into the operating system.

• 28:21Steven Sinofsky?

  So even though DirectX was first released in, in the 1990s, it, it actually wasn't part of the Windows operating system from the get go and until Windows Vista in, in 2006.

• 28:35Steven Sinofsky?

  And part of making it required in Windows Vista allowed Vista to have this transparency because that rendering engine of DirectX is how you could do all those things. It's another thing that Mac has always had high-performance graphics as part of the OS. And so that's why media people were always using the Mac because it always had that with no fuss, no muss, no crazy drivers to worry about, whereas on Windows you always had the fuss. And it was only with Windows 7 that we really finished baking it in and it always worked and then you could really rely on it. So I think, but I do think, so the way to always think about anything aesthetic with

• 29:17Steven Sinofsky?

  computing is that the tools and the capabilities of the underlying hardware end up dictating the appearance of the software. So for example, like a lot of people are into dark mode and you know, part of the lore of dark mode was that the reason it became so popular was because on phones and watches and things like that, it uses slightly less power when you're in this dark on light version of the screen. So then all of a sudden dark mode becomes like a thing and even though it's rooted in these physical capabilities, the transparency, translucency, rounded corners, all part of the underlying rendering engine that made those possible.

• 29:59Steven Sinofsky?

  When we switched to the stark sort of primary color solid, that was really for speed and battery life. And that's what we did on Windows 8 and that was the, that sort of look was to actually be more efficient.

• 30:13Speaker 02

  Wow. Well, that's about all the time we have. So Stephen.

• 30:17Steven Sinofsky?

  Awesome. We're super excited for you.

• 30:22Erik Torenberg?

  Thanks for listening to this episode of the A16Z Podcast. If you liked this episode, be sure to like, comment, subscribe, leave us a rating or review, and share it with your friends and family. For more episodes, go to YouTube, Apple Podcasts, and Spotify. Follow us on X at A16Z and subscribe to our Substack at A16Z.substack.com. Thanks again for listening and I'll see you in the next episode.

• 30:47Erik Torenberg?

  As a reminder, the content here is for informational purposes only, should not be taken as legal, business, tax, or investment advice, or be used to evaluate any investment or security, and is not directed at any investors or potential investors in any A16Z fund. Please note that A16Z and its affiliates may also maintain investments in the companies discussed in this podcast. For more details, including a link to our investments, please see A16Z.com/disclosures.