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How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs)


We tend to undervalue the things we're good at. We tend to think work has to be unpleasant. And so if something is easy and fun, we don't tend to think it's valuable. So i think lots of people gravitate in this direction of like, let's go do unpleasant things and grind our way through the career because that's the way to make it. But the reality is you should go do the thing that you feel guilty to get paid for, if there's a thing like that, and do the hell out of it, right? Do it as hard as you can. If you get pleasure from doing something that people want to pay you for, do it the best you can do it, as hard as you can do it. And if that's messing around and playing around with cool ideas, do the hell out of that.


Work doesn't necessarily have to be hard. Today my guest is sam schillace. Sam has an incredible resume that is very hard to summarize succinctly. I'l give it a shot. Currently, he is corporate vice president and deputy chief technology officer at microsoft, where he leads efforts in the consumer product space, infrastructure, and ai. Sam is most known for basically inventing google docs with his company writely, which was acquired by google, and became the foundation for what is now google workspace, which currently has over one billion active users a month. After joining google, sam ended up responsible for many of google's consumer applications, including parts of gmail, maps, automotive, groups, reader, and more. He's also founded six startups, was senior vice president of engineering at box through their ipo. He's also worked at intuit, macromedia. He was even a vc at google ventures for a time. As you'd suspect, we had a fairly wide-ranging conversation, but the core focus was around innovation, how to think big, how to come up with original ideas, why optimism is so important and powerful, and also a ton of career advice. Sam is hilarious and not what i imagined a corporate vice president at microsoft would be like, which gives me even more respect for microsoft. A big thank you to brett berson for making this introduction. With that, i bring you sam schillace, after a short word from our sponsors. This time of year is prime for career reflection and setting goals for professional growth. I always like to spend this time reflecting on what i accomplished the previous year, what i hope to accomplish the next year, and whether this is the year i look for a new opportunity.

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Thank you. Happy to be here. A really fun fact about you is that apparently you have the very first google doc file. I don't know what you call it. The very first google doc document saved somewhere from before even google docs was a thing. And does it still work in today's google docs? And what is in this document? Yeah, it does actually still work. It's pretty funny. Actually, if i move my camera for a second you might, if you're on youtube, you can see the writely thing in the background. Writely was the company that did google docs. Yeah, it still works. And it's funny though because it's like the document of dcs, right? So we started off 2005, wrote this thing in c#, which is a little known, in our own it was pre-cloud, so we had three file servers that we rented that were windows machines in a data center in texas with a sysadmin in the philippines running them. So it started there. And then when we moved to google, we ported everything to java, we moved all the data over into bigtable. And we didn't lose anything. We never lost anybody's stuff. So it's still there and moved across. And then so that's one backend migration, and there's another one with spanner. And then the front end has been rewritten twice as well. So it's like, is it really the same document? I don't know. The front end, back end have been rewritten. It's not much. It's just me saying something to steve about, is collaboration working? Are we colliding on each other? Because we were trying to figure out typing on one line, if that algorithm was working. And then there's a picture of edna from the incredibles pasted into it.

I don't know why. I think that came after, so i might've gone back and pasted that in. I'm not sure when. We must've been testing pictures or something. Unfortunately, we don't have the version history anymore, so i don't know what was original. But it is the oldest google doc from october 2005 or something like that. I love that this philosophical answer of, is it still the same google doc, considering all the code has been redone. Well, the computer history museum wants to curate it. I talked to these guys and they were like, "oh, that's so cool. We'l take that.". I'm like, "how?". I can make you a pdf. Now it's not the document. I can share you into it, but please don't edit it. How do you curate this? So that's funny. Yeah. It needs to be on the blockchain. Yeah. If you made the nft of it, that would be more authentic, i think, than the document almost.

It's kind of funny. That's amazing. And it's amazing that it still works. That's a testament to, i don't know, you/google. Well, i'l tell you a quick google story. When we migrated in to google, we were very sneaky about it, and we put the site into "maintenance mode" for eight hours on a sunday, where everything was just read-only. And then we migrated all the data and moved everything and brought the new system up. And three days after that, sergei was in a meeting with me and he's like, "so when are you guys going to move over to google infrastructure?". And i got to tell them, "oh yeah, we did it this weekend.". No one noticed. Some blogger in germany noticed that the ip address changed and that was it.

Nobody noticed it at all, so we were really good about it. Man, i love these sneaky stories. I'm hoping we hear more. There's a bunch of stuff i want to cover, the first is this broad idea of disruptive innovation. I know that you spend a lot of time thinking about this. Google docs is a great example of this. It feels like microsoft increasingly is getting really good at this. Just the idea of doing something completely new, oftentimes things that people didn't think were possible. So let me just ask a broad question. Why is this important to you? Why do you spend a lot of time thinking about this? And then just what are some tools you've found to help you and other people think more innovatively, more originally? It's an interesting question. The why it's important part, i don't know, it just is. Everything you're wearing, eating, using, listening to, sitting on, was a disruptive innovation at some point. That's how everything happens, right? I think there's this really interesting thing where everything new is threatening at some level at the beginning. I mean, probably literally the first guy who invented chairs got shit from his tribe mates for making a chair. And they're all obvious in retrospect, right? Everything is obvious in retrospect. But i think there's this really deep thing that people have where if something is disruptive of your worldview, it feels threatening, and you have this very stark choice to make that's either you're wrong or it's wrong. And humans are storytellers. It's very easy for us to tell stories about why something is right or wrong if we're motivated to. And so i call these why-not questions. People ask these why-not questions a lot. So a new thing pops up, and if you're not ready to receive it for some reason, you're not already half there or you don't have a problem that it solves or whatever, it's just threatening and irritating, and you come up with a why-not question. We heard a bunch of these with google docs, with writely, in the early days about the browser wasn't ready, people wouldn't the whole model of the cloud was like, people aren't going to trust you to store your files.

That's really weird. What if there's no connectivity? I heard the no connectivity on an airplane story 100 times from journalists. Like, "what if i'm on an airplane and i write stuff?". I'm like, "i don't know. There'l be connectivity on airplanes soon.". Which there is. And those are all just why-not questions. I think the more interesting ones are the what-if questions, like, what if this does work? Just use your imagination. Think about, how far can i extend the curve? What are the implications of that? I'm an engineer, and engineers are fundamentally pessimistic people. Somebody once told me engineers come into the world broken. They just look at everything as a problem to be solved. And i think there's something to that. But i feel like i've missed out more by being pessimistic than i have by being too optimistic too early. So i have this kind of mantra now that there's just not that much of a prize for being pessimistic and right, particularly in a moment like this. It's much better to be optimistic and wrong than pessimistic and right, i think. So i don't know. And i'm an impatient person. I'm a creative person. I'm a messy person. I just like to create and explore and find stuff. So disruptive innovation just seems natural to me. But i think it's not an exaggeration to say, literally, that wheat you had in your bread this morning, if you eat bread, some weirdo was messing around with plants 1,000 years ago and everybody thought he was a nut, or she was a nut, and then we had wheat because somebody just everything, right? Everything is like that. Along the same lines, i was actually just working on a post around first-principles thinking. And i found this quote from steve jobs just reminding us that everything around us was designed by some person that wasn't necessarily that much smarter than you. And there's no reason there isn't a better way. It just happens to be the way it is today. Yeah. One of the other ones that i like to keep in mind is every new idea looks dumb at first. Unfortunately, the dumb ideas also look dumb at first. It's not a perfect . But the more disruptive they are, the more dumb you're going to feel they are. You always listen for stuff like if they say it's a toy or if it's practical or it's stupid or i don't get it or whatever, those are often toy is a good keyword. If you hear people saying something's a toy, that's often a really good signifier that it's actually something real and threatening, and they can't think of a better criticism for it than it's just a toy right now.

Yeah, i imagine people thought about google docs that way initially. It was like, "oh, this little toy in the browser.". Yeah, we got all this stuff. I mean, the real interesting thing, like i said at the beginning, you have this very binary reaction that's possible, right? You either understand it, in which case, you're super excited about it like, "cool, the world's going to change in this exciting way.". Or you don't and you reject it. And to the degree that something is really disruptive, that reaction, that binary reaction gets really strong. And so with something like docs, we got this thing with docs that was really confusing in the early days to me, where there was a small group of people that really liked it. Some of them liked it more than we liked it. Nate torkington over at writely was this super huge early booster for it. And i did not understand what he saw in it at first.

But then we had people that just wanted it to die in a fire. And that bifurcation of love it, hate it, is really how you have an idea of whether you have impact in what you're building. If you get more of the bell curve of modern indifference and maybe mild like and mild dislike, that's an's an incremental product. That's not really disrupting anything. But if you look at something like chatgpt where the entire world is like, "this is amazing.". Or, "this is terrible.". And there's not a whole lot in between, that's a very good signifier of it being truly impactful and disruptive. Whether it's actually good or bad is a separate question. But there's no denying that's a disruptive technology. That's an awesome framework. Basically, if it feels like people sort of like it, mostly people don't care, very few people love it or hate it, probably not disruptive. If some people absolutely love it and a lot of people really hate it, good sign. Right. Yeah. Actually, weirdly enough. It's not voting, right? In the early days, we had, i don't know, a couple of million users, five million users, and there were still executives at google telling me that it was a stupid idea and that it should stop and we shouldn't be doing it. So, for a long time, the haters outnumbered the people who were fans. And who cares? Whatever. It's fine. As long as you don't run out of the people who love it, that's fine.


Is there another example of you using this what-if approach either on a product you worked on or something you've seen and it working out? I'm doing a lot of it right now, honestly. I mean, that's probably the most immediate example. But i could almost point at any product and there's moments like that in there. But right now there's a lot of why-not stories, right, around generative ai. So it's expensive, it hallucinates, you can't necessarily it's sarcastic, it's random, it doesn't do the same thing twice. Yeah, they're real, they're actual issues to solve, but i look at it and think, "well, what if? What if we can build software around it? What if we can build more complicated programs than what we've been able to build? What if we actually have a reasoning engine that we can use to do meaningful things? What if this is really the second industrial revolution where, in the first one, we had a surplus of physical energy beyond just our bodies and things like water reels, and now we have a surplus of cognitive energy beyond just our brains, right?".

And that's a really transformational idea. So i'm completely in that mode right now, honestly. I think that's just the right mindset for something that's obviously this disruptive, right or wrong. Tesla is a great example. Spacex is a great example where people are like, "that doesn't make any sense.". And elon's like, "well, what if you could land rockets and reuse them and they get really cheap? That's pretty amazing. What if i can fix the battery problems and a car is basically a software product, right?". Those are pretty amazing what-if questions, right, of those products. Yeah. So in this work on understanding what first principles actually looks like when you're thinking from first principles, the steps are essentially, figure out what you want to do, figure out the levers that keep you from achieving that thing, and then basically question every assumption that stands in the way of making this possible. So i think elon's a great. The classic example. You can't talk about first-principles thinking without quoting elon, telling stories of elon. But essentially, it's just, okay, how much would it cost to make this if we were to start over and not i mean, the why-nots, there are actually problems you need to pay attention to eventually to build stuff. But once you have the what-if, right, just to pick on spacex for a second, right? If you have what-if of like, "if i could make payload to space cost a lot less, what if?". Okay, that's amazing. That's an amazing world. Let's see if we can work on that problem. And then now you have all the why-nots? Why not? Why isn't it as cheap as it could be?

And you can start to break the problem down and think about it that way. It's a good model. This connects to something else that i know you're big on, which is optimism, being optimistic. There's this feeling that pessimism, you're often right. There's growing pessimism in the world in a lot of ways, especially in technology. I know you're a big proponent of staying optimistic. Can you just talk about why you think that's important and how you approach that? It's funny, it's a choice. I'm not an optimistic person by nature. I'm just not. All the people in my life, if any of them listen to this, they'l just laugh at the idea that i'm a proponent for optimism per se. It's just a conscious choice. I don't think you get very much for being pessimistic necessarily. You definitely don't get a lot for being careless. You can be optimistic to the point of being careless and causing harm, for sure.

Maybe a better way to say it is growth mindset, right? You want to look at the possibilities rather than the limitations, and suspend some disbelief and just work on these problems. I just personally feel like i've missed out on more than i've protected myself from. If i sum up both sides of that equation over my career, i wish i had been more open-minded and more optimistic, and more willing to try things, and more focused on possibilities rather than problems. And so i'm just personally choosing to do that, try to do that as a habit. Nothing deeper than that. I just think it's a better place to be, particularly it's kind of funny. When i came out here, i was pre-med. I dropped out of school. I came out to be a computer scientist with my friend. I didn't think of it that way. I came out to have a job at ashton-tate with a friend of mine, and spent 10 years not understanding that i was actually in a career and thinking that it was a temporary thing where i had to go back to med school and get my degree and be a doctor or something boring like that.

And so for 35 years of doing this, it hasn't occurred to me that, oh, actually, i'm in this computer industry that's this technical industry that's constantly growing and constantly inventing things and constantly coming up with these new ideas. And actually, the best posture in that world is to be creative and curious and open and optimistic and try things and stuff like that. The other thing i'l say about optimism too is related to doing these disruptive things like docs. Going back to this idea of all the good ideas look bad at first. Okay, so that's a first principle. That's a sort of fundamental thing of you're going to constantly be challenged by the really good ideas. So how do you overcome it? Well, one way you can overcome it is you want to be able to try things more easily. So part of that is being more optimistic, so being more willing to try stuff, and part of it is also just making it cheaper to try things. Very early story of docs, when i had the idea for writely, my two co-founders who were both deep domain experts in both app building and word processors were like, "the browser is never going to support this.

It's a bad idea. Let's not do this.". And they were right and wrong at the same time. They were right that it didn't support even what we have today and wouldn't have supported a full experience, but wrong in that the world was going to change and evolve. And we would never have done the first experiment if it had been a long and costly thing to do, right? So the fact that our tools were sharp and i could say, "let's do this thing.". And it only takes a couple of days to get it on its feet and see how it feels, it's kind of a form of optimism, right? If you're super pessimistic, you can be like, "even that's not worth it. Two days is a waste of time.". So there's always a little bit of a leap of faith. And then you want to make those as consumable as possible. You want to be able to try things out quickly and learn things and do these experiments. Now, lots of people have said that before, but i think all those pieces connect for me in this idea of being optimistic and open to trying stuff. Because stuff always is different. You're always wrong about products. That's one of my other rules is you're just always wrong. And so you have to try it. You have to put it in front of people. You have to try it yourself before you'l understand it. No one can really design products in their head completely as far as i can tell. Awesome. There's a few threads i want to follow there.

But this is also a tool that i found came up again and again in first-principles thinking, people that are really good at this, is just trying it. There's a lot of just, "nah, it's not going to work.". And exactly as you just described, you often find out you're completely wrong when you actually try it out. And you have this quote, i think in one of your newsletter posts, talking about building google docs. You describe it as just fuck around. Yeah. Kind of. Get to the edge of something and fuck around. That's the strategy. Yeah. Get to the edge is only get your tools as sharp as you can get them to be.

Make it so that you can try lots of cheap experiments, right? And just mess around and see what happens, see what pops out. And just try to be observant. I think the other part of optimism too is there's a receptiveness to it, right? If you're very pessimistic, you might miss the surprising result that pops out of an experiment. You might force yourself to do a bunch of experiments grudgingly, but you're like, "you know what? I hate this. I'm doing four experiments today because i have to do it because i want to be an entrepreneur, but it sucks and everything's miserable and black.".

And then you won't notice that, oh, this thing didn't work, but it didn't work in an interesting way. And you're more receptive to that kind of surprising thing, i think, when you're in an optimistic frame of mind. Like, "oh, let's see how far i can get with this. Oh, it's not working, but why isn't it working? Well, that's kind of interesting. It broke here.". And we've done stuff like that in some of the things, the projects i've got going in microsoft right now, we've got a chatbot thing we've been working on for a while and with memory, long-running memory so that you can have long conversations with it. And they work okay, but they don't work great in some ways. And we were trying to get multiple versions of them working together, like multi-agents working together.

And we gave them whiteboard working memory as a shared working memory thing to fix this problem. And that turns out to make them much smarter. Don't know why. It just makes them smarter. So that was one of these nice little bits of discovery where if you're in a pessimistic frame of mind, you might've said, "well, these don't work that well, let's give up on it.". More optimistic frame of mind was like, "well, let's try to give them a whiteboard just like a person and see if they cooperate better.". And it turns out they really do.

So another example of that mindset. Along this thread, i was going to ask about this earlier, but there's a lot of technologies people get optimistic about. Crypto comes to mind, not that there's nothing there, but a lot of people got really optimistic and then it turned out there wasn't really a lot of business to be built and then things entered wintertime. Is there anything you've learned that gives you a signal that, "lets keep working, i'm going to stay optimistic about this thing?". I spent a lot of time really thinking hard about crypto and whether i was just reacting to it because it threatens some part of my identity or whatever. And i never came down to anything that seemed valuable. I mean, that was always the thing for me is just there has to be a what if that i can say, "well what if this works? How valuable is it?". And for crypto i was always like, "well what if it works? Then i have to run up sec on my personal finances. That sounds dystopian.

I don't want that.". I can't think of anything as a user that i think actually is valuable here, even in the best case. So i feel like the pessimism is justified. So that's one of my other root principles is just like it's all about user value. Users are lazy, right? We're all lazy. We don't really care that much at the end of the day. No one's going to do something really in their life for any other reason other than it makes their life better. Nobody cares that you're friendly or nice or the logo is pretty or whatever. They care about making their life easier. We're all cynical at heart at some level, so if you can't point at user value, significant user value, it's not going to work. It doesn't matter. Shove all the marketing dollars into it you want, you can write all the articles you want, but it's got to actually solve a problem, a real problem, at the end of the day.

I just never saw that with crypto. Yeah. So i think the lesson there is truly understand if the value is real, versus, this sounds really cool, you think a lot of would you want it? I think is a nice exercise there. We pick on poor elon, but i feel like with a lot of his products, at least he's got lots of other issues, but he articulates clear user value even in the beginning when he's hyping things up. Like teslas, right? Okay, so electric cars weren't ready, he did the roadsters, whatever. But he at least articulated this idea that we're going to put a lot of batteries in these things. They're going to really be real cars. They're going to have a real range. We're going to figure out the charging problems. As an end user i'm like, "okay, that's great. Now i have a car that works like a car that solves some problems that's way cheaper to operate, because the fuel is cheaper. He's solving all the end user problems for me.".

That at least makes sense. Even if you don't believe that he's going to do it or believe in the way he did it, at least the end user value proposition makes sense, right? You have this other great quote in your newsletter, "people are lazy. Look beyond cool too, on how much easier new tool or tech makes someone's life. Convenience always wins.". Can you talk about that, just this realization people are just lazy and that's the key? Yeah,. Well i mean that is the thing. I think as product builders, it's hard to not love what you're doing. You build a product because you love it, you build it because you understand some problem, you build it because you want a paycheck maybe sometimes. But we build it for all these reasons that just do not matter to the end user at all.

And if there's one thing i've learned about product, particularly in the consumer space, just kind of in general, is people are just lazy about stuff and don't care about anything other than it making their life better. The thing that's complicated with that is there's two things about it that i think are interesting that follow from that principle. One is, i think products almost follow these thermodynamic rules where if you add a little bit of value, your adoption goes slowly and if you add a lot of value, your adoption goes really quickly, right? I think chatgpt is a great recent example of something that was just added a ton of new value to the world and got this explosive growth, and then you see lots of other ai stuff that people are doing that's just not bad, but not great, and it's sort of kind of adding a little bit of value and slowly lumbering along, or maybe it's going to collapse under its weight.

That's one thing about the users are lazy part of this. And then the other one i think is, again, it's almost like physics. I think of this as entropy, or people who are confused about entropy or will be like, "entropy is not real. Look, it runs backwards all the time on earth. Life gets more complicated. What is the deal with entropy?". And like, "well no, you have to consider the whole system, right? The entire system of the solar system, including the sun is increasing in entropy all the time. We're just making use of some of it.". And i think the same thing is kind of true about user laziness, where people are like, "this tiny thing that i'm focusing on, this feature that i added is better.

Therefore, users should adopt it.". But you forget all the stuff around it. The user has to hear about it, the user has to remember it in the moment. The user has to learn how to use it, they have to build the habit. That's all effort, right? Not to mention the fact that the actual use of your feature might have friction on the way in, right? It might be hard to sign up for it. When we did writely at the beginning, we didn't even ask for an email address, because it was such a novel thing. We didn't want any friction at all in the onboarding process. So you could just come in and make a document and start using it without telling us anything at all about yourself. And after about two minutes of typing, if you're still there, we'd very gently just say, "please give us your email address, no password, no anything. Just give us your email address so we can send you a url of this document in case you care about it later. Because if you leave, we'l never know where we'l never be able to find it again.".

But we were super focused on that, as little friction as possible. And i think it's well known in the consumer space, you don't have the number of seconds you have is not many. 15 seconds, 30 seconds, right, to convince somebody that there's some value there. They're not going to hang out and grind their way through a bunch of high-friction stuff to sign up for your thing. That's the other part of it is just, users will only adopt what you're doing if that sum total of energy that they have to expend is less than the resulting ease in their life that they get, usually by a factor of at least a couple, right? So it has to make your life a lot better, hopefully a really a lot better, like 10x better than what you spend to use it. What i think of as you're describing this is, microsoft excel had a billion toolbars and buttons and options, which allowed google docs essentially to come in with a much simpler experience. Now you're on the other side of that, which is i didn't think about. Yeah, it's a really funny place to be. And it's funny to be at microsoft, because i'm kind of the enemy, right? Because i'm the guy who messed them up a little bit. So there's some friction around that. Yeah,. I mean i think there are similar trade-offs to be made right now, by the way, with ai. I think there's similar opportunities. But we made this choice with so it's a little hard to remember, right? Because it's like 18 years, 17 years ago now, 18 years ago almost.

In that era, office was impregnable, right? So software had to be distributed physically, right, it had to be shipped around, it had to be bought and installed. It was harder to use. And so there's a very high transactional cost. Because there's a very high transactional cost, the buyers would always make this decision like, "do i want the thing with 1,000 features or the thing with 995 features? I don't know what those last five are, but i might as well have all of them.". And so that was just the lock-in for microsoft, right? So we made this trade-off, we're like, "look, we're easy to use, we're zero install, you don't have to ever deal with it's super convenient. Plus you get this one new feature that's really useful, which is collaborating with each other and not having to send attachments around the old file servers, but we're going to take away most of the features, because we don't care about them that much.".

And we took away a little bit more than we should have. In the early days, we'd get all these complaints about people who wanted word count, which i thought was a really weird. I thought that was going to be way at the end of the list. We didn't have rulers, we didn't have any kind of formatting at that point, any real pagination. We just had these basic documents. But page word count came in, of course it was students, was one of our early adopters. So they really wanted to know if they were at the word count for the essay that they had just had assigned to them.

So there was this dance with microsoft that we deliberately made this trade-off. And i think it's almost like a classic innovator's dilemma model, right? We had this incumbent that was asymptotically approaching usefulness, they're adding stuff. Whenever they added stuff, it wasn't really that much more valuable. And then we were this small thing that came in into a market that they didn't care that much about, that they didn't understand that well, which is the internet stuff, this disruptive new thing. We just chipped away from the bottom, like the innovator's dilemma. And i think it was hard for microsoft to respond to it. I think it took them a while to even have a clear idea of how they were going to respond to it. In retrospect, they did fine. We took a bunch of market share, but they kept all the money basically. So we being google. So they survived it. They did a good job surviving the challenge. We have all the users now, but they have all the money. We have all the money, i guess now. I want to spend more time on google docs and the story there. A couple questions. How long did it take from starting on it to feeling like it's working? Whatever you consider product market fit. Almost immediately, honestly.

It was weird, the process of it was, i had this idea, we set this thing up, we started working together. We're like, "ah, that's actually pretty " so basically history is like i noticed contents editable, so the browser would do some editing for you. And then i noticed javascript, i never realized that javascript is out there. And we had done word processors in the past, this team, and for a long time. In fact, my co-founder, steve, the other person on that document, wrote this thing called full write way back in 1987 or something like that was a direct competitor. '. 85. I think even, that was a direct competitor to word one. So we knew word processors, and so we decided to just try it. What's it like to build a word processor?

And the fact that you could collaborate on them was kind of an accident. They're just these things on the server. We hadn't built the thing that would lock somebody out yet. So there was just like, "here's a document, you can edit these two things.". Which we, a, immediately realized was really cool. We could both work in the same document at the same time. And then, b, realized, "oh, crap, we're colliding with each other, because there's no presence or anything like that. And there's no collision detection or anything like that.".

So pretty quickly we're like, "oh, that's kind of cool. That feels good as a development team to have these shared documents, not to send stuff around and not so that's cool. So let's build that out.". But like, "oh, bummer, collaboration's a problem. We'l have to go fix that.". And naively figured out that's a problem. And it took forever to get that working. It was really hard in the time, because we didn't do operational transform. I don't think that technique had been quite invented yet. And so we did three-way merge, which doesn't work that well, because the browsers the logical document, a document can be rendered differently in html. There's not a canonical representation. And so you're doing merges where alphabetization can change, the order of attributes can change, the tree structure can change. Firefox would do a blank paragraph with a singleton br tag, and ie would do it with an open closed paragraph tag. And so even the tree doesn't match. So it's a really hard merge problem.

So that turned out to be a gnarly hard problem to solve. But once we had seen the value of working together, we were motivated to do that. The interesting thing too with that is, i think if we'd gotten it in the other order, we might not have done it. It's another good example of why not and what if, right? Where we got really lucky that we saw the what if part, that we saw how cool a document in a browser that you could collaborate on would be, because if we understood how hard the collaboration piece would've been first without understanding that value, we might've been like, "eh, it's not worth it. It's going to be so hard to solve that problem. It's probably not a useful app.". So i think it's a good little counter example of that optimistic, pessimistic perspective we were talking about. We could easily have missed that idea, easily have missed that idea. And we just got lucky i think in the order it got presented to us. That is really interesting actually, that you need to be pulled to the what if getting you so excited that you're going to spend however many years it took you to solve that problem, because you are so excited about this what if. I think that's a really good-. Yeah,. I mean i've spent a lot of time. It's kind of funny, i keep expecting people to just be like, "all right, grandpa, stop talking about docs. It's been a long time.". Right? So it has been a long time. It's been 17 years, but it's still very relevant. It's got a couple billion users now i think, it's a big thing.

But i've spent a lot of the last 10 or 15 years just thinking about, why did that work? What worked about that? What lessons can i draw from it? There was a lot of energy around it, positive and negative. The first week i was at google, an executive there refused to give me hardware, because he thought that google was an app company not a it was a search company, not an app company. And literally the guy in charge of hardware at the time refused to give me hardware for this service. And i had to threaten to either sue him or haul him in front of eric schmidt, because i had a contract and i had contracted earnouts.

So that was another one of these interesting lessons of sometimes the opposition is enormous. And if i had just been a random google employee with this idea and no legal protection, and the ceo wasn't a fan of the project, it would've died. There's no way it would've made it through that negativity and that pessimism and that person being either challenged or afraid of the idea, or just not able to imagine it, or what. I'm not sure what. But we'l keep coming back to this idea of optimism, but i have this very strong feeling about that most of the reason people don't do really innovative good products is this kind of mindset. You're just not seeing the opportunities. There's a lot of hard work for sure. There's a lot of stuff that you can read about and best practices of doing iteration and user testing and user interviews and really listening and all the engineering best practices. That stuff is pretty mechanical. Once you know where you're going, you can do that. It's not that hard to learn and to master it. I think the hard stuff is this mindset of being open in the right ways and understanding that some kinds of pushback are good pushback. Some are bad. I always think that product builders and entrepreneurs, you have this really hard problem of you have to be very rigid about your mission. I know where i'm going. I know what my mission is, and i'm going to go there because the world doesn't care, it's going to push back. But you also have to be really flexible about feedback. You're probably aren't going to be right about a bunch of it. And so you have to blend these two things together somehow. It's like a samurai sword that's hard on the back, but softer on the edge so it doesn't break.

Or the other way around i think. But there's this hard thing you have to do as an entrepreneur, and i think it's the real core of building really great products is finding that balance and really listening to those signals, being open to it. And also knowing how long to commit to it versus time to move on to something else. So along those lines, what was the moment where you finally felt product market fit for what became google docs, and how long was that from the beginning of starting to work on it? It depends on what market we're talking about. I've been continually surprised at the adoption of docs. I think we knew there was something there pretty quickly, probably in the first couple months. There was a lot of energy around it was a weird ride, because we built this thing on a whim, and as an experiment. We liked it. We decided to go just advertise on google. At the time, 37signals was the cool company. And we're like, "that looks cool. We'l just be some engineers and we'l have a little subscription saas business thing and chill out. So let's see what it costs to acquire customers. So let's go advertise on google and see how much it costs to get people to sort of show up, and then we'l figure out if we have a subscription business or not.".

And that just got us noticed. That got us noticed by google. It got us noticed. We were i think one of the first 10 articles at techcrunch, like michael arrington. Another funny story is that i had a breakfast with michael arrington at bucks, in that era where he was trying to decide, he had this spreadsheet idea he wanted to work on and he was trying to decide he should go do that and maybe join forces with us, because we were cool, or if he should continue to work on this blog thing he had gone called techcrunch. So i might be partially responsible for techcrunch, because we turned him down and said, "you should go do techcrunch instead.". Every time i would bump into him, i would laugh about that one.

But when we got noticed, we really got noticed. There was just this period where we were the hot thing for a couple months, where every vc wanted to talk to us and everyone's trying to figure it out. Because i think we're like when you see one point on the line, like gmail, which came before us, you're like, "oh, that's kind of cool. That's an interesting quasi-app.". But it's like a weird kind of app. It's serialized. You can't really interact with it that much. And then you see this as another point on the curve and you're like, "oh, that's a real app. Oh, crap. I wonder, is there anything stopping us from doing the rest of office? Oh, probably not. How far is this going to go?". And so i think we were that second point that showed that there was actually this totally different paradigm. And so we just got this enormous amount of tension pretty quickly. And then the rest of it was feeling our way through what does it actually mean? How much of the functionality do we need to build? What's the really important part about it? How much of its collaboration? We spent a bunch of energy on offline, which was miserable, which never turned out to matter that much.

Now that team has spent a long time replicating all these features that we abandoned by the wayside, which i think i'm not that interested in. I think the future of documents looks very different than what we have now. I think it's kind of funny now that we're spending billions of dollars on gpus to emulate wind pulp and ink pressed by metal type. We're building linear documents that are fixed, that are static. So one of the things we've been doing with these chatbot things is they also serve as documents. I say bots or docs all the time. And so you'l do these things where you. I do this all the time, where we'l interview we'l create a new one. It has a separate identity, as a separate document, and then you tell it like, "i'm going to write a technical document. Here's roughly what it's about. Why don't you interview me?". So it interviews you for an hour, and now you've got this nice linear artifact which you can read. It's very readable because it's conversational. But at the same time, you've been building all these semantically encoded virtual synthetic memories in the spectre database. So you can come in and say, "show me a diagram of this. Draw this diagram for me, change it in the following way. What is this? If i change this, what if i change that?

Summarize this part of it.". So you can start to interact with it. That's still creating stuff at the bottom of this linear artifact. But the next step that we're working on now is just making that dynamic where you just come to something and you talk to it and interact with it. I think one of the things that's going to happen is, just like it seems well, in the early days of docs, people would say, "well, what if i'm not connected?". And one of the things i would say is, "in three or five years, if you get handed a device that's not connected to the internet, your word for it is going to be broken.".

Which is true, right? It's anachronistic and weird if something's not connected. I think we're going to feel the same way about intention and interactivity in our products very soon. If i can't tell something what my intent is and have it configure itself in an intelligent way, have it converse with me, whether that's a device or a piece of gui ux somewhere, i think it's going to feel anachronistic. It's going to feel really weird. There's that scene in one of the early star trek movies where scotty tries to talk to the mouse, right? He's like, "computer make the " he's pissed off because he can't talk to the computer.

We're all going to be like that in five years i think, about it. And it's going to seem really weird that we have these applications that i can't collaborate with the application. Why can't i collaborate with the applications? It's like the application's locked on a file server just like the pre docs days. Why can't i just interact with it and have it configure itself the way i want it to configure itself, and show me the data the way i want to see this, and let me build the workflow the way i want it, and remember it for me and bring it back later, and all that stuff? So that was a long digression, but i would just like you're asking about features and functionality, and i feel like where we are now with these feature wars, it's just silly. It's not the point at all. I think documents are going to change radically in the next few years. I want to follow that thread. Before i do, i found the first techcrunch post about you guys.

Starts with, "imagine word, but as an ajax browser application.". Oh, yeah, there you go. Yeah. It wasn't even javascript. It was ajax, so hot back then. It's also funny too, because i'l talk to young front end developers these days. I'm like, "i don't want to scare you too much, but jquery didn't even exist when i wrote this thing. This is like bare metal in the dom, and there were bugs.". When i went to google, i had to write this little network stack at the bottom of the javascript that in theory . You could interrupt, you could have multiple requests inflate and you can interrupt them and discard them and stuff. But the stack at the time was really buggy, and i think it was iee. And so i wrote this little network queue that would keep track of whether there were requests in flight, and kill them in a way that didn't break everything. And it was hard to do, because it's this weird asynchronous programming. And that piece of code, when i went to google, they made me reformat it for the javascript readability standards, and i could not get it to work with their formatting. There was some bug in the javascript compiler of the time that whitespace mattered. And so i wound up checking it in broken, got the readability badge and immediately fixed it.


It's like that was another one of our little hacks to get this working. I love it. This episode is brought to you by ahrefs. Many of you already know ahrefs as one of the top tools for search engine optimization. It's used by thousands of seos and companies like ibm, adidas, and ebay. What you may not know is that there's a free version that was made with small website owners in mind. It's called ahrefs webmaster tools. It's free and it can help you bring more traffic to your website. Ahrefs webmaster tools will show you keywords that you rank for and back links that you can get. It also performs automated site audits to find what issues prevent your website from ranking higher on google. Every detected issue comes with a detailed explanation and advice on how to fix it.


Visit ahrefs.com/awt, set up a free account, connect your website and start improving it. That's a-h-r-e-f-s dot com/awt. There's often this criticism as an engineer, you just want to work on interesting things and work on the technology before you find a problem that it's solving. It feels like with this example it was, you just think this is a cool technology, let's see what happens. Do you have any, i don't know, learnings or advice for when it's actually fine. Let's just play with this tech, be at the edges, you said, and maybe it'l lead somewhere, versus you should probably try to avoid that and first focus on a problem. I'm guilty of that. I mean, i like to play with stuff. I tend to think with my fingers as much as anything else. So i actually think there's a good place for just play with the tech a lot and figure out what it's good for. What i've evolved to doing these days with my teams is i pick what i call north stars that i think are interesting, useful things to get to rather than just messing around.

What's a cool thing that i think might be buildable with this? So right now we're doing these multi-agent systems. We're trying to figure out how much independent work they can do without a person holding their hand. And so a nice domain to test that out in is programming, because you don't have a whole lot of you just give something a python environment and a file system and that's it and that's all it needs. And so you're not distracted by connectivity issues or whatever. So one of the problems right now is go write the eye in python. That's a problem i could give to an intern and it would take them a summer to do some halfway decent job of it. It's a thing you could expect a reasonably competent programmer to do, mostly independently. And so it should be possible for the system, if it's independent at all, to go do that. So is that useful by itself? No, because we already have the eye, it doesn't matter. But if we build a system of programming agents that can self-monitor and self-correct and bug themselves, that can build things that are roughly that scale of complexity, that's valuable. That would be a valuable thing to have. It's kind of interesting too, because that system already, it's produced a bunch of good insights. One of them is its kind of complicated and then hard to debug it. It's this asynchronous system of stochastic agents. That's a lot of stuff to deal with. So we wrote a debugger agent. And debugger agent watches stuff, and when there's a problem somewhere, it goes and figures out what the problem is and then gives you a nice explanation of what you broke and what needs to be fixed. And we haven't turned it loose on actually fixing things yet because we don't trust it, but it's very helpful as an assistant . We had one that documented itself too. That's the other one we did recently. Just turned it loose on documenting the code base and did a pretty good job of it. So it's starting to produce interesting stuff, right?

Because we have these north stars that we aim things at. And i think that's maybe a good antidote to this. Just playing with tech without being focused doesn't tend to produce anything that's super valuable. But picking these, even if they're arbitrary goals, as long as they're real goals that you're trying to get to, that's useful, right? Where you're like, "i wonder if i can get this to work. I wonder if i can build this thing.". Then grind away at that for a week and see how close i can get. See what i learned about why it's hard. That's probably better than just like, "let me poke at javascript for a while.". It's also different, i think, at a bigger company where you need to achieve something, versus i think as just an engineer out of college just playing around, like, go for it, right? It's just like, what's the worst that could happen? Even the early days of writely, the very i mean, we had a goal from the beginning. The beginning was like, "can i write a word processor in a browser?". That was literally the problem statement, right? It was like, "i have content edible, i have ajax or javascript. Can i put these together and something that feels like a word processor?

Let's go do that.". It's kind of half messing around with tech, but it's also half an actual goal. So i don't know. I like playing around with i think a lot of the good product ideas, most of the good product ideas actually come up from engineering. So i think there's a lot to be said for, get familiar with tools, particularly weird esoteric combinations of tools can often be useful. If you understand or three things at google, i was one of only two people in the company who had the code readability, which is the right to check in code in this language, and both a backend language, which is the monitoring language, org mode, a middle tier language, which is java, and a front language, which is javascript. No one else would do that full stack. I think it's useful to have that broad perspective sometimes. Sam, the renaissance man of all languages. Yeah, add more like it,. But yeah, i pay attention to things. I wanted to follow this thread a little further around being good at these what if questions. It feels like you've built this, or maybe you were born with this skill of thinking in the future, thinking about what's possible, thinking about where things are going. Is there anything that you could recommend to people listening to get better at the skill? Because for a lot of product people, this is really important to figure out, where could we be going and let's work back.

This is a really interesting question. And i may actually write, i've been thinking about writing a book from some of my sunday letters, and this is maybe the frame of it. So i'm curious to see how flamed i get from saying this, it'l be interesting to see. I think there's this weird thing that i've noticed. I go talk to university kids and stuff like that, and there's this weird thing i noticed where when i was in university and i would talk to old guys like me, they would all say the pc is this stupid toy, whatever, it's not real computing, go on a mainframe or whatever. And my attitude was like, "out of the way, old man, just like, you're irrelevant. I'm going to go do this thing. It's awesome.". And go. And now when i talk to kids, i actually had a slide up at michigan when i was talking recently that was titled, okay humor, and the professor actually put it up there. Because this generation is very pessimistic and doesn't seem to be quite as engaged and energetic about solving problems. And i've been puzzling through it. And i think maybe there's a bunch of different things that intersect. I think one of them is, i think they all have to do with the willingness to take risk and to fail, honestly. I think that's really where it comes from. So i think you see a lot of filtered content. And that filtered content presents low probability events like five and six-sigma events as though they were normal. So you see everybody makes $100 million in their startup in the first three months. So if your startup isn't making $100 million, you're an idiot. There's that stuff.

There's also, you're living out loud, so when you fail in that context it feels very painful. But i think there's also for elite students, like people at these elite schools, they're hard to get into. I went to michigan, "you're kind of smart. Michigan's a good school. You live nearby, go apply to that one.". Nothing serious about it, but kids in the elite schools, their lives are highly curated going up to getting into a school like that now, right? Those students like, "i didn't do sports, i didn't do extracurricular. I was just a weird nerd having to be good at math.". And so i think there's that as well. If you're highly curated where you've spent a lot of your life thinking, "everything i do has to have a reason and an output.". It's very hard to just mess around and do something that might lead down a surprising path, right? So that's the curation is part of it. And then i think just in about the mid '80s when i graduated from high school, we stopped letting kids just play on their own, unsupervised outside with other kids. I grew up in this neighborhood full of, it was like the faculty ghetto for this small university my dad taught at, and we just ran wild. It was on the estate of widow of dodge motor, founder of dodge motor, so we had a couple hundred acres of swamp and fields to go run around in.


We did hair-raisingly, dangerous things that my parents never knew about, and really explored and had fun. I think if you put all those pieces together, i think there's much less of an ability and willingness and skillset around experimenting to the point of failure, making a fool of yourself, having bad ideas. I send stupid emails to satya at microsoft all the time where i'm just like, "i don't know what the hell he thinks of me at this point.". Because i send him all these goofy ideas. I think he actually gets it and he's like, he likes it, because i don't think people usually do that for him. But i'm just like, "man, this is " then i'l send him an email a week later.

I'm like, "yeah, that was a dumb idea. Sorry about that. I've decided that wasn't a very good one.". But i think you cannot dance if you can't if you're afraid to embarrass yourself. You cannot succeed if you're afraid to fail. That's just how it is. You have to have that sense of play. You have to have that sense of, it's okay if this doesn't work, i'l iterate on it. I have this personal motto, which is, from error comes virtue. Because i'm a maker, i make stuff. And i fuck it up all the time. I have poor motor skills, so i make mistakes constantly, and then i just figure out how to make the mistake into a virtue somehow. So i think it's a really good skill to have. The saying i took on this year. And i really like it as my i never had a personal motto before. I think it might be my personal motto, it's like, virtue from error.

Amazing. On this topic of failing. I think a lot of people hear this advice and they're like, "yeah, okay, i need to fail more.". It's hard to do. And oftentimes your performance at a company is negatively impacted. And it feels like for you it was just, you've done it enough times where fine, okay, it's going to be fine. I launch this thing, no one cares. I email satya this thing, he ignores it or he doesn't. It's going to be okay. Is that maybe the key to this or is there anything else that you've done to allow you to be okay with failure? I feel like you can have a linear return on your effort if you manage things in a linear way, which is i think that tightly managing, okay, nothing's going to be surprising, i'm going to be within this boundary, i'm going to slowly accrete value, i'm going to play this game, whatever. I think you can have a nice linear, boring return to your career and you'l climb the ladder, it takes 30 years or whatever. I don't have the patience for that. And i think the way you get extraordinary returns is you do extraordinary things, right? You have to take bigger risks, and have more interesting shots to have this kind of extraordinary result in your career. I feel like i always tell people, i think i mean, i pitch this because i've observed myself and thought about what has been successful in my career. It's not a thing everybody can do. I'm just kind of like this. I never really fully grew up. I'm kind of this weirdo. I still feel i'm 57 now, and i feel like i'm about 17. I'm still very immature and like to mess around with stuff and play with things.


So not everybody can do it. But i think there's, at the end of the day, the reason you get ahead in your career is you had a lot of impact. And the reason you had a lot of impact was because you picked something that you're good at that you did with a lot of intensity that wound up having impact, right? And so i think the good at part of it is hard too. We tend to undervalue the things we're good at. We tend to think work has to be unpleasant. And so if something is easy and fun, we don't tend to think it's very valuable. So i think lots of people gravitate in this direction of, let's go do unpleasant things and grind our way through the career, because that's the way to make it. But the reality is, you should go do the thing that you feel guilty to get paid for, if there's a thing like that, and do the hell out of it, right? Do it as hard as you can. If you get pleasure from doing something that people want to pay you for, do it the best you can do it, as hard as you can do it. And if that's messing around and playing around with cool ideas, do the hell out of that. Work doesn't necessarily have to be hard. It often is, but it doesn't have to be. And the best case is that it isn't. The most impact you'l ever have is where you're in that mode where you're just in the flow and doing your thing and you're happy to do it and you can't quite believe they pay you and you don't understand how you're getting away with this, but it's super cool anyways, right? I think that's the career thing that makes sense to me. At least that's what i've done. Who knows? It's all luck sometimes, so it's hard to replicate these. Everybody has a different path. Amazing. I love that advice. It's exactly where i was going to take our conversation, so i love that you took us there. It makes me think of, i'm reading charlie munger's almanac, which just came out through stripe press. And warren buffett and charlie munger's whole philosophy is, when you find an advantage, just go huge. Just go big, right? Make one bet a year. But when you find that, go for it.


Don't buy a little bit at a time. And i love that's exactly what you're saying. Sometimes things don't make sense either. So i'l lean over and show you, for people with the video. That's an instrument i made. It's an instrument. So the top of that's a piece of redwood, this one right behind me with the cat eyes, the reason it's got these weird cat eyes, by the way, this is virtue from error right there, i dug this piece of wood out of the forest. It'd been sitting on the forest floor for 80 years trying to not rot and doing a pretty good job of it, because it's redwood. And there were knots in it. So those two cat eyes are where the knots were. There's another knot right here that i couldn't get out. But there's two knots in there that i had to carve out of there.

That's a very weird design that i did by hand. It doesn't quite work. It's kind of a failure. The arch of it's a little bit too high, so it's a little hard to play, because the pick hits the top because the strings get a little bit close to the top. So like that but that's an experiment. I was playing around. I wanted to do this thing. It was fun to do. It was a passion project. Now it's just hanging on the wall. Not everything works. Clearly i don't have a career as a luthier either. So it's more just a fun thing to do. But that's just a good example of the. I don't know. Sometimes i don't even understand why i do stuff. You just do it because you do it. Because it makes some sense to you. Many people are in the opposite boat where they don't like what they're doing, they're miserable, but they have to have a job. They need income, they need to pay their rent, feed their family. I know, i realize what i'm saying is very privileged, and i am sorry about that. But from some perspective. But i imagine you were also in those situations occasionally. Is there anything you recommend to folks that aren't in that, i would do this for free, i'm so excited about this work? Do you recommend try to get out that as soon as you can? Is it enjoy it as much as you can, get the most out of it? I mean, i've done plenty of things for money.

I've done plenty of jobs to make money for my family, things i did not enjoy doing. All i can say is really, i stopped doing those things as soon as i could stop doing them. Not only as fast as i physically could, because i definitely had that calvinist, oldest boy thing of, must provide, must suffer kind of thing. So it took me a long time to realize, no, actually i'm really creative. I don't have to be like everybody else. I can have my own path, and i can be this weird engineer. I always joke that i'm an engineer. Two is a prime number. It's just like i'm kind of a programmer, but not real i'm this weird non-linear person that only barely fits into the programming world. But it's okay. It took me a long time to figure out that i could do that i could be comfortable with that part of myself. And i'm fortunate enough now that i've done enough things and have enough of a connection and network that people understand who i am and the value i can bring.

And so i get away with doing that stuff that i like doing. So it is kind of privileged advice, and it's not something everybody can do at every stage in their career. Certainly earlier stages you often have to make compromises, but i still think it's worth paying attention to, right? When you're working, what makes you happy? What is the stuff that you feel guilty for getting away with? When i started managing people, i couldn't understand why people were paying me and i wasn't writing code, because all of my energy was attached to, "i can produce a lot of lines of code every day.".

And i asked my boss at the time, "why are you so happy with this? I'm not writing anything.". He's like, "i don't know what you're doing. Everywhere you go, it gets better. So just keep doing whatever it is you're doing.". And that was one of these moments where i was just like, "oh, i could do something else and it's kind of fun. I like talking to people all day. That's great. They're going to pay me for talking to people all day. If they seem happy, i'm happy. Let me just lean into this for a while and see where it goes.".

So i think you just look for those moments when somebody is willing to let you do something that you feel happy to do, surprisingly happy to do, or doesn't feel like it's the thing you "should be doing". If you get those surprises like this, i think this goes back to this openness, the optimism that we were talking about. You have to be receptive and attentive to those moments when they show up. So i think they are in every career. If you listen for them, you'l see stuff show up where you don't think of it as who you are, but somebody else sees it in you and if you can be open to it, you can do these pivots. When you talk about that makes me think of seth godin has this really important advice that's always stuck with me, that no matter what job you're in, just try to enjoy it and do the best version of that job you can, because you'l enjoy it more, that you'l end up being more successful, and it's just a good habit to just like, "i'm just going to do the best i can at being a waitress at this place. I'm just going to do the best at greeting people entering the apple store.". Absolutely. Yeah, i think that's absolutely right. And even more than that, just find a way to bring yourself to it, right?

What is the thing that you can do in this role that is unique to you that you're the most comfortable with, right, where you really have high impact. I don't know. I tend to be very, it's kind of a joke because i'm a programmer, i tend to be a very binary person, right? I'm either all in or all out on something. So whenever i do something, i do it with just a ridiculous amount of intensity, for better or for worse. So i find the ways to do stuff. I tend to be very unhappy if i can't be intense in something successfully, and then if i can be intense in it successfully, i'm happier and the people around me are probably less happy, but stuff happens.

Anyways, i get things done. Speaking of getting things done and being intense and working things that are really interesting, you're responsible for some of the cutting-edge work happening at microsoft in ai. You're spending a lot of time in ai. I'm curious to get your take on just what you find interesting, where you think things are going, what people should know about ai. I'l share a couple of quotes that you put out somewhere that i have here that i think are cool. One is, "ai isn't a feature of your product. Your product is a feature of ai.".

I love that one. Yeah. Another is, "it'l be possible to add some value by building ai into your product, but really transformative massive value will come from building apps and solutions that won't work at all without it, that treat it as a true platform.". Yeah, i think both of those are really true. So what i'm working on is, most of the industry right now is focused on, when you talk about somebody who's working in ai, it's somebody who's creating models, right? It's somebody who's figuring out how to do some new open source model or somebody who's doing some new training or make some model bigger. And i think that's very, it's valid, useful work. It's just not the kind of work i like to do very much. And a lot of people are doing it. And so i'm an app builder, i'm a tool builder, and so i don't create models, i consume them, right? I want to build things around them. And so when i started with microsoft, started working on gpt-4 with microsoft in september of last year, my immediate reaction to it after picking my jaw up off the floor, which we were all doing in the early days, was, "okay, this is cool, but in some computer science sense, it's just this function, this stochastic pure function that just takes a character array and rearranges it and hands it back to you. That's not much of a building block for building programs. We need state and we need control flow, and orchestration, and call-outs.". So that just started me down this rabbit hole of thinking about building the semantic kernel, which we built, and then building infinite chatbot, which was next, and these other projects we've been working on.

And the more i think about this stuff, the more i do think those two quotes are good quotes. I think what's going to happen over time i actually think we're at the beginning of this just gigantic disruption in the software industry. I think the way that the internet made distribution of information free, i think ai is going to make pixels free. So pixels are expensive to produce now, they take programmers and they take lots of infrastructure, and putting a pixel in front of the user is a hard thing to do and lots of software is predicated on that. Lots of business is. The way lots of businesses were predicated on it being hard to distribute information 25 years ago. But you can see this already with things like just images, right? Two years ago, if you wanted a piece of digital art, you had to go invent photoshop, learn to use photoshop, use photoshop to do the drawing, build the skills up. That's a lot of work to produce those pixels. Now it's like, i want a picture of a cat riding a bike eating a banana, done, right? So those pixels got really free.

And the similar things are happening in the business world as well, and i think it's just going to start to happen everywhere. So you can draw this is what if, let's go ask some what ifs. So what if the models get really good at planning, so they get more independent, they can do longer and complicated things? What if the multimodal stuff gets really good so that they can both consume and produce dynamic ui like i was talking about? What if we figure out a good way to store state, this is my bots or docs thing. So what if do we figure out a good way for you to really highly personalize something so it knows you really. Well. And you trust it with confidential information? If you have all of those things, you're just going to spend a lot of time talking to that agent. It's like, what would you do if you imagine you're the richest person in the world, you've got 100 of the best people working for you, and a chief of staff, and they're tireless, and they never fight with each other, they do everything you want. With that staff supporting you, what are you doing with software? What are you doing when you're sitting in front of a screen? Well, you're probably communicating intention and you're probably consuming some either entertainment or some of the products of that intent. And that's about it. You're not messing around with pokey static apps and stuff. That doesn't work, right? You're just telling your staff to deal with stuff for you.

So i think that's where we're headed, i think, in the world of software at least. Things are going to get more dynamic, more intentional, more semantic, more fluid, then more personalized. I think there's a ton of problems to be solved to make that vision real. But i think this feels to me a little bit like seeing the palm maybe, or the early iphone, where you're just like, "okay, i get it. Phones are going to get interesting. That's a new device. Now we got to go do a whole bunch of engineering before they actually are as useful as they're today.".

Right? So i get it. I think software is going to change radically now. I had the same feeling when we started doing this is going back to docs again. It's another lesson. It's another one of these category shifts. The second we got writely up on its feet and i was like, "ah, the browser is actually a platform that you can actually build real apps in. I get it, the world's going to change.". And we had a ton of stuff to do, right? Nobody really understood distributed systems. Nobody understood how to build stuff in multiple places at once or how you deal with replication, how you deal with security, all kinds of hard all the development patterns had to shift from waterfall, to agile, to ci-cd, all this stuff had to change to fully realize that world. But i remember back in 2005, this very quick and the people who were the strong proponents, i think all saw this, instantly saw that the world had changed and there was this new category.

And i have exactly the same feeling about generative ai. Like, yep, software's going to totally change. These businesses are going to totally change. It might take 10 years to really work through all of it, but yep, door open, new room, new game, start coloring in the blanks, right? Let's go. So that's where i think we're going. And that sounded really certain, it probably sounded more certain than i should sound. I think there's a lot of, probably a quarter at least, if not a half of what i just said is wrong in some way. So we're going to learn a bunch of stuff along the way. And there's a lot of work to do, a whole lot of work to do and a whole lot of unanticipated side effects are going to pop out, and there's just a whole lot of stuff to get that to be real the way there was with all of the last transformations.

But i think this is just a giant category shift. I think it's just incontrovertible that it is. It's kind of funny when gemini came out, all the press take was like, "oh, it's not that different from gpt-4. I guess we're done with ai now, we can go back to bed.". I'm like, "that is the dumbest possible interpretation of that story that you could come up with i think.". Of all the takes you could have had on that, i think that was the dumbest one honestly. It could say many things about either company. It could say many things about the science.

But, "guess there's nothing here to see.". Is not one of them. For somebody listening that wants to not fall behind on this and or find opportunity for their product, other than just playing with it, which is what everyone is always saying, just like, "play with it. Use chatgpt, use bard, and all these things.". Is there any advice you'd give listeners for how to approach thinking about ai, how it integrates into the stuff they're doing? Yeah, i agree with you. Just play with it, is not really great advice. I think the best technique i've really seen for learning things is to pick a thing to do with the thing you're trying to learn, right? Even if it's an unreasonable even if it's a goofy, weird thing, right? Like i'm going to figure out how to draw funny pictures with this programming language or whatever. Even if it's a dumb thing like that, picking some arbitrary goal and being a little bit stubborn about trying to get yourself to it is a good way to learn stuff. And then the question is, "what goals are you picking?". So try to pick goals that lead somewhere maybe at least a little bit interesting. So if your goal is just like, "i'm going to mess around with chatgp for an hour.". That's not really much of a goal. If it's like, "i'm going to go try to gpt that can do this part of my job, let's see how close i can get.". That's more interesting, right?

And i do think unfortunately, one of the other ways in which this is very reminiscent of the early dot com era, and i think plenty of people have said this, is this sense of exhaustion in keeping up. There's so much stuff going on right now. And that's i think another good strong indicator that something really big is going on, where it's just very difficult to keep track of all the stuff that's happening. It's kind of interesting, because i remember, just to kick crypto's corpse one last time, there was a tweet at the beginning of the year that i saw that somebody was like, "yeah, it took the ai bros a week to come up with as many use cases as crypto came up with in a decade.".

Which definitely feels true, right? It's just so much stuff going on. And i think you just have to try to keep track of it. One of the other things i think is going on in the moment, which feels a lot like the cloud moment to me, is it's hard to get the first idea. The zero to one is hard. Understanding that there's something there at all is the really hard part, because you have to be lucky and you have to be talented and you have to look in the right place and do some very hard work. But once you understand that there's something there, like the cloud model works, or their generative ai matters and scale works and stuff like that. Once you're there, the one to many, all the optimization stuff, that happens in parallel, it happens really quickly. Many people can do it. There's a lot of energy. It'l just go really fast. So i think we're in that phase where just like we're in the elaboration phase where we understand this step and people are just filling in all the white space as fast as they can. So that'l slow down eventually, hopefully. We'l see what the next year brings. But yeah,. It's a hard time. It's hard for professionals even. I think you just have to read a lot.

You have to think a lot. You have to play with stuff. You have to choose your battles. You have to pick good targets. Pick a goal in your domain that would matter to you if you can get to it, and then go try to solve that problem with some specific technology and get to know that technology. Maybe pick the technology based on how popular it seems, if you want to learn something lots of people . Those are all good. I think you just have these kind of mundane. I don't think it's really a secret, i don't think. They're kind of mundane strategies, but you just have to pick some stuff and do some homework. And there's no magic single bullet to learning this stuff. You just have to run. It's like, "how do i run this sprint without getting out of breath?". You don't. You're going to be out of breath, run hard. It's just what it is.


I love that advice. And i love it connects to everything else that you've been talking about is, find some problem someone has, find some value you could provide, and then think about, how can ai potentially provide that? I think that's really practical. Great advice. Maybe a last question just around microsoft. It feels like microsoft is firing on all cylinders. It feels like it's become one of the most innovative companies out there. It feels like satya is known now as the most innovative, best executing ceo out there potentially. That's just what it feels like. Being on the inside, i'm just curious, what is it that you think microsoft is doing so right. Or how they think that enables them to be so innovative and continue to be such a behemoth as so much has changed in tech? There's a couple of things. First of all, i think very highly of satya, or i wouldn't be there. I really like satya. He is very much what he appears to be from the outside. I've had plenty of candid private conversations with him and watched him in meetings and stuff like that. He's a very decent, genuine, honest, high energy, caring individual with a ton of empathy. He's really motivational in a way that is not destructive. He believes very strongly that a leader's job is to raise the energy of the organization and he really lives that. And i watch him in meetings where i'm a domain expert and i cannot believe how engaged he is in stuff and how much he understands about something that i know he's not as deep an expert as some of the people in the room are. And he's fully in there. So he is a really incredible leader in many ways. That's one thing. I think another is that culture is very humble, honestly. I mean, it's interesting going from google to microsoft. And i don't want to draw comparisons or anything like that, but i think there are definitely similarities and differences between the companies. And i think one thing that stands out with microsoft is it's a humble culture. It does unglamorous work all the time to make businesses be successful. So it's got that sort of mindset of just hard work and humility, which i value a lot.

And then i think there's just, i mean honestly, there's just a fantastic number of really talented people working there. It's kind of funny, this year i've been writing a lot of patents, because there's just a lot of stuff going on in the world. And i've written more patents this year by a lot than the rest of my career combined. And i commented on the number. I'm like, "i've written 15 patents this year.". I commented to the patent attorney that i work with. He's like, "ah, that's nothing. The chief science officer wrote 700 of them one year during the mobile boom.".

It's like, whatever you feel about patents, and i don't necessarily love patents, although it's part of my job to write them, but that's the kind of people that are there, these just fantastically talented people with just really deep experience at a lot of different levels. I think that's part of it too. There's just a lot of really good folks there. Kevin scott, who i work for, is one of the smartest. He's probably the smartest person i've ever been fortunate to work directly with. He's definitely one of the smartest i've ever met. He's pretty fantastic. And the group around him is pretty fantastic, and the leadership in windows and office is pretty fantastic. So it's just a lot of good people and a lot of good attitude, and a good leader i think is the answer. And luck. It's always luck too, right? Kevin and satya made a bet on openai a few years back, and they're doing some extraordinary things with capital raise and the support of that technology and stuff like that. That doesn't happen by accident either. No drama there, by the way. I wouldn't know anything there. I hear it's calm. I stay far away from it as possible, honestly. Most under-the-radar startup out there. Amazing. Sam, is there anything else you want to share before we get to our very exciting lightning round? Is there anything you want to leave listeners with? Mostly i think probably take all of this as more my personal opinions and not microsoft's official stands. This is just me being an engineer. I'm not here as a microsoft representative necessarily. But yeah,. I don't know. Build stuff, solve problems, build stuff. That's what it is, right? That jobs quote- fuck around. Fuck around. Well, that jobs quote is right. The world was built by people just like you. That's the thing. It's really true. You don't have to have permission, you just have to have energy.

With that, we've reached our very exciting lightning round. Are you ready? Probably not. Great answer. Sam. What are two or three books that you've recommended most to other people? I like weird book. There's this book called invisible cities by italo calvino, which is this very beautiful meditation on the nature of cities and the nature of venice. And i read it the first time i was in italy right after college, and it just blew all the circuits in my brain when i went to venice, and so that was pretty cool. The other one i recommend to people with some caution is this very intense and disturbing book called the wasp factory by ian banks, which is probably the creepiest and hardest book i've ever read, but it's a very interesting psychological deep dive. So those are both fiction. If you're looking for business advice, i think the business advice one is probably, where good ideas come from, steven johnson.

I really like that book. I think some of the stuff about the adjacent possible. I think it's an old book now, but i think it's pretty timely still. I think he had some good stuff in there. What is a favorite recent movie or tv show that you really enjoyed? My favorite one right now, my guilty pleasure is watching gary oldman be a completely disgusting over-the-hill british spy in slow horses, which is pretty fun. And i'm actually having a little fun with the retro monster stuff like monarch and stuff like that. It's kind of fun to watch. I don't know. I have absolute junk food taste when it comes to media. Love creepy monsters and bugs. Yeah. I love it. Shooty science things that blow up a lot. I'm not very deep. By the way, have you seen scavengers reign, scavenger reigns, scavenger reign? Okay. You'd love it's on hbo. It's incredible. It's an animated sci-fi thing, and it's very creepy, slimy, kind of alieny things, and it's so beautiful.

Do you have a favorite interview question that you like to ask candidates when you're interviewing them? I have one that got banned at google, and i liked it. I still think it's a fun question. It's, how many zeros are at the end of 100 factorial? And the reason i like it. Yeah, it's like, you made the face, right? Going to ask chatgpt for this answer. Well, here's the thing. Well, don't though, because the reason i ask it is, it seems like an unreasonable and impossible answer. And if you sit down and think about it a little bit, i'm not going to tell you how to reason through it, but you can figure out the answer to it in a few minutes. And so the reason i ask is not to get to the answer. It's because i just want to see how people react when i give them something that seems impossible and unreasonable. And some people just back off and refuse to engage with it. And some people are just like, "i don't know, let me roll my sleeves up and see how far i can get in this thing.". And if you do that, you can actually get through it. And i just think it's interesting, because that's building stuff, right? That's a good signal of when somebody tells you can't write a word processor in the browser and you can't do collaboration. Do you roll your sleeves up and deal with it or do you fall over? And what was the question again? Just to . How many zeros are at the end of 100 factorial in decimal?

And then why did it get banned? I think it got known, and somewhere actually, the funny thing is, one of their more senior directors, actually he's a svp now i think, dave. , i interviewed him when he came in, and i asked him that question. And his response was, "i don't do math. Next question.". And so i failed him. I was the veto. And they have this policy where we're friends now. They have this policy where one veto is actually a good signal. If you're controversial as a candidate, they would take a hard look at you. And so my veto may have gotten him higher, because i was like, "i don't know, he wouldn't answer this question. That's a red flag for me, so don't hire him.". And he turned out to be a great person. So it's maybe not a good question anyways. That comes back to one of your other lessons of the best ideas have some people that are just very anti that idea.


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