What Running Windows at Microsoft Taught Steven Sinofsky About Apple

I think that Steve created a culture of artists and they thought of themselves that way.

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

icon came out.

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.

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.

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

it.

In 2007 Bill Gates sat on stage with Steve Jobs at the All Things Deconference, 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 tastes alone explains it.

Steven Sinovsky, 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 Sinovsky who is a legendary software warrior in the industry.

According to his LinkedIn, he's a board partner at A16Z.

He wrote a hardcore software inside the Rise of the Fall, the PC revolution, all about

his time at Microsoft, where he was at forever, starting as a project lead in the 80s and

90s and working his way up to the president of the Windows division.

He worked there at the same time as my dad.

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

So Steven...

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

fade.

He dressed up as Clippy.

I don't even have a picture of that.

That would be so funny off asking about that later.

So we're here because this week, April, 2026 is the 50th anniversary of Apple.

Thanks to your position in the industry over all these years, what do you think are the

most important, like most sailing and cultural differences between Apple and Microsoft?

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

Bill Gates' career and 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 book

into 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 previous questions about the industry.

And that was, I think, like in 1982 or 1981, unbelievable.

And then you fast forward.

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.

It was iconic.

It was iconic.

And the photos by Asimata, 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 or 300 people in the audience.

And but that probably is 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 real artists

steel.

And it was actually in the movie The Pirates of Silicon Valley.

I mean, there was a famous, there was a pirate flag atop the Apple building where Macintosh

was originally conceived.

And 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.

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 is 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 at the original developer

on the iPhone operating system.

You know, they, when 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.

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 can 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

a 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 kind of an amazing thing is you would think the artists 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.

So do you think this distinction still captures it 20 years after this Gates Jobs interview?

Is Apple still artists and absolutely people?

Absolutely.

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 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 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 it, it, it, 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, 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.

Yeah, I agree, that's why I use them.

And I'm curious actually, what, like, what is your personal tech stack?

Like, do you just like daily drive Apple, everything?

I actually, you know, it's very interesting.

Yes, I, I do and, 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 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, was shows up on the Mac first and people share things that

are sort of macnative 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.

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, the bleeding edge of our industry on Mac.

And the, 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, 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, and now you're looking at 30 plus percent on the, the global share.

And it's, 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, 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 a significant business community there.

But the, the share number, I mean, considering it was less than 3% when Microsoft basically

rescued Apple from certain bankruptcy in, in 1997, right when Steve came back to the company.

Um, you know, this gradual climb, like, first with the iMac, and then a series of products that

followed that, including the iPod, which were 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. Then it never really did.

Um, and the Neo is due 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,

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, 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. 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. Then Windows Nista shipped, but Windows Vista didn't run on those

machines because they only had four gigabytes of storage and, and one gigabyte of RAM. And Vista

just couldn't run. And so we have 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 NIO really,

that, that 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 that,

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 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 back seat, 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 consumption.

And so it's it, you know, 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, you know, unbelievable. I mean, that product. And of course, what's fascinating is

what's, you know, we did circus at the roughly the same time. So you can see it, it only worked in

portrait mode. Never seen that. It was like this, this weird dock. And it was really

just use for 10 bucks. 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 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 the surface hardware, which was like the high praise at the time.

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 fine my,

I had to have FaceTime. And so I just 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 Max. 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. Yeah. So gaming has this 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 the the tier one AAA, you know, FPS,

those kind of games. And where frame rate is everything. And part of those games are that the

the people 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. 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 and the same as 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 who's 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

step. 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, 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 which is AI compute on the device. And so suddenly these companion processors,

like on 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 and called CUDA and the whole suite of APIs around Nvidia. And so

Microsoft and Nvidia were kind of that 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 Maccentric. 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

Nvidia chips. 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 max 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 at any kids games and stuff or all that, you know, Apple's ecosystem is fantastic for those.

It's just those tier one triple A things that that you don't really see.

Yeah, so going back to the MacBook Neo, do you think Windows laptops are just kind of cooked now?

Like what will they be able to do to counteract the $600?

Or totally great general purpose computing device that Apple just came up with?

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 are like IBM mainframes running like the 360 instruction

set, which, you know, runs banks and stuff like that. But the EC, you know, you could take,

you know, a Windows 11 machine and you could run the original versions of a Warden 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 readers,

some gadgets, some sensors, some factor 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 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 going to 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. 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 device, it's just non competitive. First eight 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 they best by 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 run nine, not in chance. It gets nine. 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 doomed. All of these things

are problematic. And and yeah, so it's worse. No, and it weighs a ton. It's like, what is it? Does

go down to the weight and the physical spec? I mean, because it's going to, yeah, three and a half pounds.

That's a tank. And so almost a pound heavier than the, yeah, yeah, from the Neo. And so

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. Oh, that's cheap. That's that it's it. Oh, God. Now, that's expensive. So it's $80 cheaper.

That's why I said, but the the Neo, the beauty of it, of course, is it's running a phone chip

that's being paid for a hundred thousand pounds over by the sales of all the phones. So there's

not even any what you call a MRE non recurring engineering costs baked into the Neo. It, it's

really just A4. It's like all, it's like literally the actual physical marginal cost to produce

another, you know, 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, it's, it's really interesting. So also in, 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 or housing college.

It was very cool, but it was kind of useless and 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 in bosses. So what's going on with this? Is this,

well, it's a big failure. It's salvageable. This is why I saw someone on the 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, 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 didn't quite know where it was going 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 I, you know,

I took them on a trip to Tokyo and I walked around. I put a warm on the plane. I watched all the

movies on the plane with them. I walked around the, the Tokyo metro station made videos,

spatial videos of the sub, they were incredible. I mean, the technology was

and reported 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 the our, uh, Jaren linear 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 80s,

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 thing just to make some cash at school where like the medical

engineering department was testing out like the interiors of tanks. And part of it was they gave

you these crazy VR goggles to send you a 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 six dollars an hour

to pretend to drive a tank. 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 arrow

vibe, the few morphism 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?

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 think we'll, we'll see a return.

I mean, Apple certainly drove a return to some transparency, some rounded corners and things

like that. I think that it's really important. The most interesting reason going back to direct

X, why Microsoft introduced Arrow first with, with, with this and Windows 7 and stuff was, it was

because Direct X was built into the operating system. So even though Direct X 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. And part of making it required in Windows Vista allowed

Vista to have this transparency, because that, that rendering engine of Direct X 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 must, no, no crazy drivers to worry about. Whereas on Windows, you always had

the puts, and it was only with Windows 7 that we really finished baking it in, and it always worked,

and, and, and, and then you could really rely on it. So I think, but I do think, so, so the,

the way to always think about anything aesthetic with computing is that the tools and the capabilities

of the underlying hardware, end up dictating the appearance of the, 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,

the, 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, that made those possible, when we switched to the star sort of primary polar 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. Well, that's about all the time we have,

so Steven Sostom. You're super excited for you.

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