Lenny's Podcast: Product | Career | Growth - How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs)

Starting point is 00:00:00 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, like, that's the way to make it. But the reality is like 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? Like do it as hard as you can.

Starting point is 00:00:23 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, around with cool ideas, like do the hell out of that. Like, work doesn't necessarily have to be hard. Today, my guest is Sam Scalaché. Sam has an incredible resume that is very hard to summarize succinctly. I'll give it a shot.

Starting point is 00:00:44 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, rightly, which was acquired by Google, and became the foundation for what? what is now Google Workplace, which currently has over 1 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.

Starting point is 00:01:15 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-arranging 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.

Starting point is 00:01:40 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 Burson for making this introduction. With that, I bring you Sam Scalaché, after a short word from our sponsors. This time of year is prime. for career reflection and setting goals for professional growth.

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Starting point is 00:03:53 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 documents saved somewhere from before even Google Docs was a thing. 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,

Starting point is 00:04:12 if you're on YouTube, you can see the Rightly thing in the background. That's rightly was the company that did Google Docs. Yeah, it still works. It's kind of funny, though, because it's like the document of Theseus, right? Like, it's been, so we started off 2005, wrote this thing in C-sharp, which is little known, in our own, there's like pre-cloud.

Starting point is 00:04:33 So we like 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 that's like it started there. You're like, and then when we moved to Google, we poured everything to Java. We moved all the data over in Bigtable. And we didn't lose anything. Like never lost anybody stuff. So it's still there and like moved across.

Starting point is 00:04:53 And then like that's one back end migration. And there's another one at Spanner. And then like the front end. has been rewritten twice as well. So it's like, is it really the same document? I don't know, like the front and back end have been written. It's not much. It's just me saying something to Steve about,

Starting point is 00:05:08 is collaboration working? Are we colliding on each other? Because we were trying to figure out, like, 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.

Starting point is 00:05:20 So I might have gone back and pasted that in. I'm not sure when. We must have been testing pictures or something. So I don't, unfortunately, we don't have the version history anymore. So I don't know what was original original, but it is the oldest Google Doc from like October of 2005 or something like that. I love that this philosophical answer of is still the same Google Doc,

Starting point is 00:05:39 considering all the code has been redone. Well, like, Computer History Museum wants to curate it. Like, I talked to these guys in there. Like, we're like, oh, that's so cool. We'll take that. I'm like, how? Like, I can make you a PDF. Now it's not the document.

Starting point is 00:05:50 I can share you into it, but please don't edit it. Like, you know, it's like, I don't know. How do you curate this? Yeah, I think 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.

Starting point is 00:06:09 That's the testament to, I don't know, you slash Google. Well, I'll tell you a quick Google story. Like, when we migrated in to Google, we were very sneaky about it and we like put the site into, quote, 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 the to Google infrastructure? And I got to tell him like, oh, yeah, we did it this weekend. No one noticed.

Starting point is 00:06:39 Some blogger in Germany like noticed the IP address changed and that was it. Like 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.

Starting point is 00:06:57 Google Docs is a great example. This 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 kind of 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 found to help you

Starting point is 00:07:15 and other people think more innovatively, more originally? It's an interesting question. Like, the why it's important part? Like, I don't know, it just is. like everything you're wearing, eating, using, listening to sitting on was a disruptive innovation at some point. Like, like, that's how everything happens, right? Like, I think there's this really interesting thing where everything new is threatening at some level at the beginning. I mean, probably literally like the first guy who invented chairs, like got shit from his, like,

Starting point is 00:07:44 tribe mates for making a chair. Like, you know, it's like, but like, and they're all like obvious in retrospect, right? Like, everything is obvious in retrospect. But there's, I think there's this really deep thing that people have where, you know, if something is disruptive of your worldview, it feels threatening. And you kind of have this very stark choice to make that's either you're wrong or it's wrong. And humans are storytellers. Like, it's very easy for us to tell stories about why something is right or wrong if we're motivated to. And so I think, I call these why not questions that people ask these why not questions a lot. Like, you know, so the new thing pops up. And if you're not ready to receive it for some reason, like you're not kind of already half

Starting point is 00:08:22 there or you don't have a problem that it solves or whatever, you know, it's just threatening and irritating and you come up with a why not question. We heard a bunch of these with, like, Google Docs, with rightly in the early days about like the browser wasn't ready. People wouldn't, you know, 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 like a hundred times from journalists. Like, what if I'm on an airplane on the right stuff? I'm like, I don't know. Like, there'll be connectivity on airplanes saying, like, you know, which there is. Like,

Starting point is 00:08:52 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? What, just like use your imagination, think about like what, how far can I extend the curve? What are the implications of that? I'm an engineer and engineers are like fundamentally pessimistic people. You know, we kind of somebody once told me like engineers come into the world broken.

Starting point is 00:09:13 They just like look at everything as a problem to be solved. I think there's something to that. And but I feel like I've missed out more by being pessimistic than I. I have by being too optimistic too early. So I have this kind of mantra now that like it's, you know, there's just like not that much of a prize for being pessimistic and right, particularly in a moment like this. Like it's much better to be optimistic and wrong than pessimistic and right, I think. So I know, that's like I, I just, I, and I'm like an impatient person. I'm a creative person. I'm a messy person. Like I just like to create and explore and find

Starting point is 00:09:46 stuff. So like disruptive innovation just seems, seems natural to me. But I think it's not an exaggeration to say like literally, you know, that, that wheat you had in your bread this morning if you eat bread is like, you know, some weirdo like was messing around with plants a thousand years ago and everybody thought he was a nut, she was a nut. And like, you know, then we had wheat, you know, because somebody just, you know, everything, right? Everything is like that. Along the same lines, I was actually just working on a post around first person's 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

Starting point is 00:10:24 there isn't a better way. It just happens to be the way it is today. One of the other ones that I like to keep in mind is every new idea looked dumb at first. Unfortunately, the dumb idea also looked dumb at first. It's not a perfect problem. But the disruptive, the more disruptive they are, kind of the more dumb you're going to feel they are. You always listen for that stuff like, you know, if they say it's a toy or, you know, if it's practical or it's stupid or I don't get it or whatever. Like those are often, like, toy is a good keyword. Like, if you hear people saying something's a toy, that's often a really good signifier that it's actually something real, unthreatening, and they can't think of a better criticism for it than it's, you know, it's just a toy right now. Yeah, I imagine people thought

Starting point is 00:11:02 about Google Docs that way initially. It's like, oh, this little toy in the browser. Yeah, we got all this stuff. I mean, and it, the real interesting thing, like I said at the beginning, like there's this, you know, you'll have this very binary reaction as possible, right? Like, either you understand it, in which case, like, 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, like, with something like GDX, we got this thing with GDox that was really confusing in the early days to me, were like, there was a small group of people that

Starting point is 00:11:37 really liked it. Some of them liked it more than we liked it. Like Nate Torrington over Riley, like, was this super huge early provider, early booster for it. And like, I did not understand what he saw in it at first. And, you know, but then we had people that just wanted it to die in a fire. And like that like bifurcation of like love it, hate it is really how you have an idea of like whether you have impact and what you're building. If you get like the more of the bell curve of like kind of moderate indifference and maybe mild like and mild dislike or like that's sort of an, that's an incremental product. Like that's not really disrupting anything. But if you look at something like chat TPT where like the entire world is like, this is a,

Starting point is 00:12:16 amazing or this is terrible and there's like not a whole lot in between, that's a, you know, very good signifier of it being like truly impactful and disruptive. Whether it's actually good or bad is a separate question, but like there's no denying that that's a disruptive technology. That's an awesome framework. Basically, if it feels like people sort of like it, it's some people, 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, literally enough. And like, it doesn't even, you don't even have to like add them. It's not voting, right? Like in the early days, like we had like, I don't know, a couple 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 like we shouldn't be doing it. So like, you know, like for a long time, the haters outnumbered the people who were fans. And, you know, who cares or like whatever. You know, like it's fine. Like as long as long as you like as long as you don't run out of the. people who love it, you know, that's fine.

Starting point is 00:13:17 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. Like, 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 I like right now, you know, there's a lot of why not stories, right, around generative AI. So it's expensive.

Starting point is 00:13:41 It hallucinates, you know, you can't necessarily try. It's sarcastic. It's random. It doesn't do the same thing twice. Like, yeah, they're real. They're actual issues to solve. But I think, like, you know, I look at it and think, well, what if? Like, what if we get, you know, what if we can build software around it? You know, what if we can build more complicated programs and what we've been able to build? What if we actually have a reasoning engine that we can use to do meaningful things. Like, what if this is actually 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 like, that's a really transformational idea. And, like, I think, so I, you know, I'm completely in that mode right now, honestly. Like, I think that's just, like, the right mindset for something that's obviously this disruptive, right or wrong.

Starting point is 00:14:31 Tesla is a great example. SpaceX is a great example where people are like, that doesn't make any sense. You know, when Elon's like, well, what if you could land rockets and reuse them and they get really cheap? Like, that's pretty amazing. What if I can fix the battery problems? and like the 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

Starting point is 00:14:53 when you're thinking from first principles, the steps are essentially, figure out what you want to do, you figure out the levers that keep you from achieving that thing, and then to basically question every assumption that stands in the way of making this possible. So I think Elon's a great, like the classic example. Like you can't talk about first principles thinking without quoting Elon, telling stories of Yon, but essentially is just, okay, how much would it cost to make this if we were to start over or not?

Starting point is 00:15:15 I mean, the why not? There are actually problems you need to pay attention to eventually to build stuff, but once you have the what if, right? Like just to pick on SpaceX for a second, right? Like, if you have the what if I could make, you know, wait to space cost, you know, payload to space costs a lot less, what if? Like, okay, that's amazing. That's an amazing world.

Starting point is 00:15:35 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 do like break the problem down and think about it that way. It's like that is a good, 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 always, you're often right.

Starting point is 00:15:55 There's all kind of growing pessimism in the world in a lot of ways, especially in technology. I know you're a big proponent of staying optimistic. You just talk about why you think that's important and how you approach that. It's funny. Like, it's a choice. Like, I'm not an optimistic person by nature. Like, I just not, like, even all the people in my life, if any of them listen to this, they'll just laugh at the idea that I'm like a proponent for optimism per se.

Starting point is 00:16:17 Like, it's just a conscious choice. Like, I don't think you get very much for being pessimistic necessarily. You definitely don't get a lot for being careless. Like, there's like, you know, you can be optimistic at the point of being careless and causing harm for sure. But like, you know, I think it's a, like, maybe a better way to say this growth mindset. Or like, you want to look at the possibilities rather than the limitations and like suspend some disbelief and just kind of work on these problems. I just personally feel like I've missed out on more than I've protected myself from. Like if I just kind of sum up both sides of that equation

Starting point is 00:16:50 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 like choosing to do that, try to do that as a habit. Nothing, nothing deeper than that. I just think it's a better place to be. Particularly, like, it's kind of funny. Like, when I came out here, like, I was pre-med. I dropped out of school. I came out to be a computer scientist sort of with my friend. I didn't think of that way. I came out to have a job at Ashton Tate with a friend of mine and spent 10 years, like, not understanding that I was actually in a career and thinking that it was a temporary thing where I had to go back and, like, go back to med school and get my degree

Starting point is 00:17:31 and be a doctor or something boring like that. And so, like, it's like for 35 years of doing this, like it hasn't occurred to me that, like, oh, actually, I'm in this computer industry that's like this technical industry is constantly growing and constantly inventing things and constantly, you know, coming up 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 something like that. The other thing I'll say about optimism, too, is like kind of related to doing these disruptive things like G-Dox. I think, like, you know, going back to this idea of like all the, all the, um, the good ideas look bad at first. Right. So that's, okay, so that's a, that's a first principle. Like,

Starting point is 00:18:08 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 know, you want to be able to try things more easily. Well, so part of that is being more optimistic, so being more willing to try stuff. And part of it's also just like making it cheaper to try things. Like, you know, if it's, you know, in the very early story of DDox, when I had the idea for rightly, like my two co-founders who were both deep domain experts in both app building and we're processors were like, the browser's never going to support this.

Starting point is 00:18:38 It's a bad idea. It's not do this. And they were like right and wrong at the same time. Like 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 like the world was going to change and evolve. We would never have done the first experiment if it had been a long and costly thing to do. So like the fact that our tools were sharp and we could,

Starting point is 00:19:00 I could say like, let's do this thing and it only takes a couple of days to like get it on its feet and see how it feels. It's like kind of a form of optimism, right? Like, you know, if you're super pessimistic, you'd be like, even that's not worth it, like two days is a waste of time.

Starting point is 00:19:13 So there's like always a little bit of a leap of faith. And then you kind of want to make those as consumable as possible. You want to be able to try things out quickly and learn things, you know, and do these experiments. No, lots of people have said that before, but I think it kind of all those pieces connect for me, you know,

Starting point is 00:19:28 in this idea of being optimistic and open to trying stuff. Because stuff always is different. You're always wrong about products. It's one of my other rules is like 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'll understand it. Like no one can really design products in their head completely as far as I can tell.

Starting point is 00:19:47 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 like, nah, it's not going to work. And exactly as you just described, you often find out, you're completely wrong when you actually tried out. And you have this quote, I think, in one of your newsletter posts talking about building Google Docs,

Starting point is 00:20:10 you describe it as just fuck around. Yeah, kind of. Get to the edge of something and fuck around. Yeah, that's the strategy. Yeah, get to the edges. 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, like, see what pops out and just try to be observant.

Starting point is 00:20:26 I think the other part of optimism, too, is like there's a receptiveness to it, right? Like if you're very pessimistic, you might miss the surprising result that pops out of an experiment. Like you might force yourself to do a bunch of experiments grudgingly, but you're like, you know, 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 like, you know, you won't notice that like, oh, this thing didn't work, but it didn't work in an interesting way.

Starting point is 00:20:53 And, you know, 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. like, oh, it's not working, but why isn't it working? Well, that's kind of interesting, like with Brok here. We've done stuff like that and some of the things, the projects I've got going in Microsoft right now, like we've got a chatbot thing we've been working on for a while

Starting point is 00:21:12 and with memory, long-running memory so that you can like have long conversations with it. And, you know, they work okay, but they don't work great in some ways. And we gave, we were trying to get multiple versions of them working together, like multi-agents working together. And we gave them whiteboard working memory, like as a shared working memory thing to fix this problem. And that turns out to make them much smarter.

Starting point is 00:21:33 Don't know why. Like, it just makes them smarter. Like, that was kind of one of these nice little, like, bits of discovery. Like, if you're in a pessimistic frame of mind, you might have said, like, well, these don't work that well, let's, like, give up on it. More optimistic frame of mind is like, well, let's try to, like, give them a whiteboard just like a person and, like, see if they cooperate better. And it turns out they really do.

Starting point is 00:21:50 So, like, 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 kind of entered wintertime. Is there anything you've learned that gives you a signal that let's keep working,

Starting point is 00:22:13 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 kind of, I never came down to anything that seemed valuable. I mean, that was always the thing for me is just like there has to be a what if that I can say, you know, what if this works? Like, how valuable is it? For crypto, I was always like, well, what if it works? Like, then I have to run upsec on my personal finances. That sounds dystopian. I don't want that. Like, I can't think of anything as a user that I think actually, like, is valuable here, even in the best case. So I feel like the pessimism is justified. Like that's, so that's like one of my other kind of root principles is just like, it's all. that 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.

Starting point is 00:23:10 They care about, you know, making their life easier. We're all cynical at heart at some level. So, you know, if you can't point at user value, significant user value, it's not going to work. It's not going to, it doesn't matter. Shove all the marketing dollars into what you want. You can write all the articles you want, but like, you know, it's got to actually solve a problem, a real problem at the end of the day. I just never, never saw that with crypto. Yeah. So I think the lesson there is truly understand if the value is real versus like the sounds really cool. You think a lot of, like, would you want it? I think it's a nice exercise there. We pick on poor Elon, but like, you know, I feel like with a lot of his products, at least he are, you know, he's got lots of other issues,

Starting point is 00:23:50 but like he articulates clear user value even in the beginning when he's hyping things up. Like, Tesla's, right? Like, okay, so electric cars weren't ready. He did the roadsters, like, whatever. But like, he at least articulated this idea that, like, 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. Like, you know, that, like, as an end user, I'm like, okay, that's great. Like, now I have a car that works like a car that solves some problems. It's way cheaper to operate because the fuel is cheaper. Like, he's solving all the end user problems for me. Like, 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, like 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 to

Starting point is 00:24:36 on how much easier a new tool or tech makes someone's life. Convenience always wins. You talk about that, just this realization people are just lazy and that's the key. Yeah, well, that I mean, that is the thing. Like, I think we, I think as product builders, you know, it's hard to not love what you're doing. Like, you build a product because you love it.

Starting point is 00:24:53 You build it because you understand some problem. You know, you build it because you want a paycheck maybe sometimes. But like we, you know, we build for all these reasons that just do not matter to the end user at all. And like if there's one thing I've learned about product, you know, particularly in consumer space, just kind of in general, it people are just lazy about stuff and like don't care about anything other than it making their life there. 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, like, I think products almost follow these, like, thorough and dynamic rules where, like, 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 chat GPT is a great recent example of something that was just, like, added a ton of new value to the world and, like, got this explosive growth. And then you see lots of other AI stuff that people are doing that's just, like, not bad, but not great.

Starting point is 00:25:46 And it's sort of kind of adding a little bit of value and kind of slowly, you know, lumbering along and, maybe it's kind of collapse under its weight. That's kind of the, you know, one thing, like, about the users are lazy part of this. And then the other one, I think is, again, it's almost like physics. I kind of think of this as entropy or people who are confused about entropy or it'll be like, entropy is not real. Like it runs backwards all the time on Earth. Like life gets more complicated.

Starting point is 00:26:12 Like, what is the deal with entropy? I'm like, well, no, you have to consider the whole system, right? Like, the entire system of the solar system, including the sun, is increasing 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. People are like,

Starting point is 00:26:27 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. Like, 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.

Starting point is 00:26:41 Like, that's all effort, right? Not to mention the fact that like 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 rightly 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 were still there, we'd very gently just say,

Starting point is 00:27:09 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'll never know where, you know, we'll never be able to find it again. So like, you know, so, but like, you know, we were super focused on that, like, as little friction as possible. And I think, you know, it's well known in the consumer space. You don't have, you know, the number of seconds you have, you know, is not many, like 15 seconds,

Starting point is 00:27:36 30 seconds, right? To convince somebody that there's some value there. They're not going to, like, hang out and grind their way through a bunch of high friction stuff to sign up for your thing, like you're, you know, so, like, That's the other part of it. It's just like, you know, users will only adopt what you're doing if that sum total of energy that they have to expend is less than the, you know, resulting ease in their life that they get usually by a factor of at least a couple.

Starting point is 00:28:03 Right. So it has to make your life a lot better. Hopefully, 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,

Starting point is 00:28:23 which is I never, I didn't think about. Yeah, it's a really funny place to be. Like, you know, I did like, and it's funny to be at Microsoft because I'm kind of the enemy, right? It's like I'm the guy who like messed them up a little bit. So there's some friction around that. Yeah, I mean,

Starting point is 00:28:37 I think there are similar tradeoffs 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. Like, you know, in that era, like, office was impregnable, right? Like, so software had to be distributed physically, right?

Starting point is 00:28:57 It had to be shipped around. It had to be bought and installed. It was, like, hard 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, like, you know, that was just like the lock-in for Microsoft, right?

Starting point is 00:29:18 So we made this tradeoff. We're like, look, we're easy to use. We're zero install. You don't have to ever deal with it. It's super convenient. Plus, you get this one new feature that's really, really useful, which is collaborating with each other and not having to send attachments around your file system, file servers.

Starting point is 00:29:35 But, you know, 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. Like, in the early days, we get all these complaints about people who want, what word count, which I thought was a really weird. I thought that was going to be like way at the end of the list. I thought like we didn't have rulers. Like we didn't have any kind of formatting at that point, any kind of real pagination.

Starting point is 00:29:54 We just had like these basic documents. But page count or word count came in. Of course it was students. It was one of our early adopter. 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 tradeoff. And I think it's kind of all.

Starting point is 00:30:12 It's almost like a classic innovator. dilemma model, right? Like we took this, you know, this incumbent that was like asymptotically approaching, you know, useful as like they're adding stuff. Whenever they added stuff, it wasn't really that much more valuable. And then, you know, we were this like small thing that came in to a market that they didn't care that much about, that they didn't understand that well, which is the internet stuff. It was kind of this disruptive new thing.

Starting point is 00:30:36 We just kind of chipped away from the bottom, like, you know, the innovator's dilemma. And, you know, it was, I think it was hard for Microsoft to respond to it. I think it took them a while to even have a, like, a clear idea of how they were going to respond to it. In retrospect, they did fine. Like, we took a bunch of market share, but they kept all the money, basically. So, you know, we being Google, like, you know, so like they survived it. Like, you know, they survived. They did a good job surviving the challenge.

Starting point is 00:30:59 Like, it's, you know, we have all the users now, but they have all the money. Like, we have all the money, I guess, now. I want to spend more time on Google Docs in the story there. A couple questions. How long did it take from starting on it to? feeling like it's working, like whatever you consider product market fit? Almost immediately, honestly. Like, it was weird.

Starting point is 00:31:19 Like 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, like, the history is like, I noticed content editable. So, like, the browser would do some editing for you. And then I noticed JavaScript. I could never realize JavaScript is out there.

Starting point is 00:31:38 And, like, we had done word processors in the past, this team, and, like, for a long time. In fact, like, my co-founder, Steve, the other person on that document, like, wrote this thing called Fullwright way back in, like, 1987 or something like that. That was, like, a direct competitor, 85, I think, even. That was, like, a direct competitor to Word one. So, like, we knew Word processors. And so we decided to just, like, try it. Like, what's it like to build a word processor? And, like, the fact that you could collaborate on them was kind of an accident.

Starting point is 00:32:05 Like, there was just, like, 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. Like, you can edit these two things. which we have, you know, A, immediately realized was really cool, like we could both work in the same document at the same time. And then B, realized, like, oh, crap, like, we're colliding with each other because there's no presence or anything like that.

Starting point is 00:32:25 And there's no collision detection or anything like that. So, like, pretty quickly we're like, oh, that's kind of cool. Like, that feels good as a development team to have, like, these shared documents, not to send stuff around and not, like, so that's cool. So it's built that out. But, like, oh, bummer, like, collaboration is a problem. Like, we'll have to go fix that. And, like, naively, like, figured out that, like,

Starting point is 00:32:42 that's a problem. It took forever to get that working out. It was really, really hard in the time because we didn't have, 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. The browsers, the logical document of a, you know, a document can be rendered differently in HTML. There's not a canonical representation. And so you're doing merges where, like, alphabetization can change. The order of attributes can change. The tree structure can change. Like, you know, Firefox would do a, a blank paragraph with a singleton BR tag and i.e. would do it with an open-closed paragraph tag. And so like, you know, even the treaty doesn't match. So it's a really hard merge problem. So that turned out to be like a gnarly hard problem to solve. But like once we had seen the value of like working together, we were motivated to do that. Kind of the interesting thing too with that is like I think if we'd gotten it in the other order, we might not have done it. Like it's a good another good example of why not and what if, right? We're like, we got really lucky that we saw the what if part, that we saw how cool, like, a document in a browser that you can collaborate

Starting point is 00:33:50 on would be. Because if we understood how hard the collaboration piece would have been first, without understanding that value, you might have been like, it's not worth it. Like, it's going to be so hard to solve that problem. It's probably not a, you know, useful app. So I think it's a good little counter example of like that optimistic, pessimistic perspective we were talking about. Like, 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

Starting point is 00:34:25 that problem. What if? Because you are so excited about this. Yeah. Yeah. That's what, I mean, I've spent a lot of time. It's kind of funny. Like, G-Dogs, I keep expecting people to just be like, all right, grandpa, stop talking about

Starting point is 00:34:36 G-Docs. It's been a long time. 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. Like, it's a big thing. But I've spent a lot of the last 10 or 15 years, you know, just thinking about, like, why did that work? Like, what worked about that?

Starting point is 00:34:52 Like, what lessons can I draw from it? Like, it was, there was a lot of energy around it, positive and negative. The first week I was at my, at Google, like an executive there refused to give me hardware because he thought that Google was a app company, not a, it was a search company. not an app company. And like literally like the guy in charge of hardware at the time, like 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 contracted earnouts. And like, you know, so like that was like another one of these like interesting lessons of

Starting point is 00:35:22 like sometimes the opposition is enormous. And like, you know, if I had just been like a random Google employee with this idea and no legal protection and the CEO wasn't, you know, a fan of the project, it would have died. Like there's no way it would have made. Like there's no way it would have made it through that, that negativity and that pessimism and that, you know, 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 like, we'll keep coming back to this idea of optimism. But like I have this very strong feeling about that like most of the reason people don't do really innovative good products is this kind of mindset. Like 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. the 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. Like 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 like being open in the right ways and understanding that some kinds of pushback

Starting point is 00:36:29 are good pushback. Some are bad. I always think that like product builders and entrepreneurs, you have this really hard problem of like you have to be you know very rigid about your mission like I know where I'm going I know what my mission is and like 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 like you probably aren't going to be right about a bunch of it and so like you have to like blend these two things together somehow like it's like a samurai sword that's like hard on the back but softer on the edge so it doesn't break it's never that other way around anything but like you know it's like there's this hard thing you have to do as an entrepreneur.

Starting point is 00:37:06 And I think it's like the real core of building really great products is like 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 G-Dox.

Starting point is 00:37:36 I think we knew there was something there pretty quickly, like probably in the first couple months. Like there was a lot of energy around it. Like, we wound up. That is a weird ride because, like, we built this thing kind of on a whim. And, you know, as an experiment, we liked it. We decided to go just advertise on Google. At the time, 37 signals was kind of like the cool company.

Starting point is 00:37:56 And we're like, that looks cool. Like, we'll just be some engineers and we'll have like a little subscription SaaS business thing and like 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'll figure out if we have a subscription business or not. And that just got us noticed. Like that got us noticed by Google.

Starting point is 00:38:15 It got us notice. We were like, I think, like one of the first 10 articles at TechCrunch, like Michael Lerrington. Like this another funny, rightly story is that like we had, I did a breakfast with Michael Arrington at Bucks in that era where he was like trying to decide. He had this like spreadsheet idea he wanted to work on. He was trying to decide if you 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 say, he should go to TechCrunch instead.

Starting point is 00:38:47 Every time I would bump into him, I would laugh about that with him. But like when we got noticed, like, we really got noticed. There was just this period where we're like the hot thing for, you know, a couple months, like where every VC wanted to talk to us and everyone's trying to figure it out. Because I think we're like, you know, when you see one point on the line like Gmail, which came before us, you're like, oh, that's kind of cool. Like that's an interesting quasi app, but it's like a weird kind of app. It's like serialized. You can't really interact with it that much. And then you see this as like another point on the curve.

Starting point is 00:39:17 And you're like, oh, that's a real app. Like, oh, crap. Like, I wonder, you know, is there anything stopping us from doing the rest of office? Oh, probably not. Like, how far is this going to go with, you know, so like, I think we were that second point that like showed. that there was actually this totally different paradigm. And so we just got like this enormous amount of attention pretty quickly. And then the rest of it was like feeling our way through like what does it actually mean?

Starting point is 00:39:39 Like how much of it, how much of the functionality do we need to build? What's the really important part about it? How much of its collaboration? Where you spent a bunch of energy on offline, which was miserable, which never turned out to matter that much. You know, now that team has spent a long time like 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

Starting point is 00:40:06 wind pulp and ink pressed by metal type. Like we're building linear documents that are fixed, that are static. So like one of the things we've been doing with these chatbot things is they're also, they also serve as documents. I say bots or docs all the time. And so like you'll do these things where like you, I do this all the time. I'll interview, have one. We'll create a new one as a, it has a separate identity as a,

Starting point is 00:40:29 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, like, 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 like semantically encoded virtual synthetic memories in this inspector database. So you can come in and say, like, show me a diagram of this, draw this diagram for me, change it in the following way. Like, what is, what is this? If I change this, what have I changed this? What have I changed that summarizes this part of it.

Starting point is 00:41:00 So you can start to interact with it. That's still like accreting 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 like come to something and you talk to it and interact with it. I think one of the things that's going to happen is, you know, just like it seems, well, in the early days of geox, like people would say like, well, what if I don't, what if I'm not connected? And one of the things I would say is like in three or five years,

Starting point is 00:41:24 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? Like, 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. Like, if I can't tell something what my intent is and have it configure itself, an intelligent way, have it converse with me, whether that's a device or a piece of gooey, you know, UX somewhere, I think that's, like, it's going to feel anachronistic. It's going to feel really weird.

Starting point is 00:41:55 There's like that scene in one of the early Star Trek movies. Like, Scottie tries to talk to the mouse. Right. He's like, computer. Like, make the transit. You know, like he's pissed off because he can't talk to the computer.

Starting point is 00:42:04 Like, we're all going to be like that at like five years, I think about around. And it's going to seem really weird that we have these applications that like, I can't collaborate with the application. Like, why can't I collaborate with the application? It's like the application's locked on a file server.

Starting point is 00:42:17 Just like the pre-G docs days. Like, why can't I just like interact with it and have it configure itself the way I want to configure itself and like 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 you know all that stuff so that was a long digression but I would just like you know you're kind of asking about features and functionality and I feel like where we are now with these like feature wars it's just silly like it's just it's not the point at all like I think documents are going to

Starting point is 00:42:43 change radically in the next few years I want to follow that thread before I do I found the first tech crunch post about you guys starts with imagine word but as an ajax browser application Yeah, AJ. Wasn't even JavaScript or was Ajax. Ajax. So hot back then. It's also funny, too, because, like, I'll talk to young front-end developers these days. I'm like, I don't want to scare you too much, but, like, J-Quary didn't even exist when I wrote this thing.

Starting point is 00:43:08 You know, this is like bare metal in the DOM and there were bugs. Like, when I went to Google, like, I had to write this little network stack at the bottom of the JavaScript that, like, in theory, XM. You could interrupt. You could have multiple requests in flight. you can interrupt them and discard them and stuff. But the stack at the time was really buggy and I think it was IE. And so I wrote this little like network queue that would like keep track of whether

Starting point is 00:43:33 there were requests in flight and like killed them in a way that didn't break everything. And, you know, it was hard to do like 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, with their formatting. Like there was some bug in the JavaScript compiler of the, the time that white space mattered. And so I wound up like checking it in, broken, got the readability badge, and immediately

Starting point is 00:44:00 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 ATREFs. Many of you already know ATREFs 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 websites, owners in mind. It's called H.R.F.'s Webmaster Tools. It's free and it can help you bring more

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Starting point is 00:45:06 It feels like with this example, you just think this is a cool technology. Let's see what happens. Do you have any learnings or advice for when it's actually fine? Let's just play with this tech, be at the edges, as you said, and maybe it'll lead somewhere versus like you should probably try to avoid that and first focus on a problem. I'm guilty of that.

Starting point is 00:45:23 I mean, I like to play with stuff. Like, 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, play with the tech a lot and, like, figure out what it's good for. What I've evolved to doing these days with my teams is I'll just like, I pick what I call North Stars that I think are like interesting, useful things to get to rather than just messing around. Like, what's a cool thing that I think might be buildable with this? So right now we're doing these multi-agent systems or 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

Starting point is 00:46:01 of like, you just like give something a Python environment and a file system and that's it. And like that's all it needs. And so you're not like, you know, distracted by connectivity issues or whatever. So one of the problems right now is like go write the I in Python. Like, you know, 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. You know, it's a thing you could expect a reasonably competent programmer to do. mostly independently.

Starting point is 00:46:24 And so it should be possible for like this system if it's independent at all to go do that. So is that useful by itself? No, because we already have VI. It doesn't matter.

Starting point is 00:46:31 But like 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,

Starting point is 00:46:40 that's valuable. Like that would be a valuable thing to have. It's kind of interesting too because like that system already it's produced a bunch of good insights. One of them is it's kind of complicated and hard to debug it.

Starting point is 00:46:51 It's this asynchronous in a system of stochastic agents. That's a lot of stuff to kind of deal with. So we wrote a debugger agent. When debugger agent watches stuff and like when there's a problem somewhere, it goes and figures out what the problem is and they gives you a nice explanation of like what you broke and what needs to be fixed. And like we haven't turned it loose on actually fixing things yet because we don't trust it.

Starting point is 00:47:10 But, you know, like it's like very helpful as an assistant. It's there and does this. We had one that documented itself too. That's the other one that we did recently. Just turned it loose on documenting the code base and did a pretty good job of it. 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.

Starting point is 00:47:30 Like just playing with tech without being focused doesn't tend to produce anything that's super valuable. But picking these kind of, even if they're kind of 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. Like, you know, I wonder if I can build this thing. I grind away at that for a week and see how close I can get. see what I learn about why it's hard. That's probably better than just like,

Starting point is 00:47:56 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, you know, go for it, right? It's just like, that's the worst thing that could happen. Even the early days of rightly, like, the very, I mean, we had a goal from the beginning.

Starting point is 00:48:13 The beginning was like, can I write a word processor in the browser? Like, that was literally the problem statement. Right? It was like, I have content editable. I have Ajax or JavaScript. group, like, can I put these together in something that feels like a word processor? Like, let's go do that. It's, you know, it's kind of half messing around with tech, but it's also half, like, an actual goal, like an actual goal.

Starting point is 00:48:32 So, I don't know. Like, I think that's, I like playing around us. 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, you know, get familiar with tools, particularly, like, weird, esoteric combinations of tools can often be useful. Like, if you understand two or three things. Like, at Google, like, I was one of only two people in the company who had code readability, which is like the right to check in code in this language in both a back-end language, which is the monitoring language, orgmon, a middle-tier language, which is Java,

Starting point is 00:49:07 and a front language, which is JavaScript. Like, no one else would do that full stack. I think it's useful to have, like, that broad perspective sometimes. Sam, the Renaissance Man, of all languages. ADD, more like it. But yeah. 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,

Starting point is 00:49:32 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. I'm like, I may actually write, I've been thinking about writing a book. it's 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 will be interesting to see.

Starting point is 00:49:56 I think there's, like, there's this weird thing that I've noticed. I go talk to university kids and stuff like that. And like there's this weird thing I noticed where, like when I was in the university and like old guys like, I would talk to old guys like me. Like they would all say like the PC is this stupid toy like, you know,

Starting point is 00:50:11 whatever. It's not real computing. Go on a mainframe or whatever. And my attitude was like out of the way, old man, like just like you're irrelevant. I'm going to go do this thing. It's awesome. I'm like, go, go, go.

Starting point is 00:50:21 And now when I talk to kids, I actually had a slide up at Michigan when I was talking recently that was titled OK Numer, the professor actually put it up there. Because the generation is very pessimistic and doesn't seem to be quite as like engaged and energetic about solving problems. And I've been puzzling through it. And I think maybe there's like a bunch of different things that kind of intersect. I think one of them is, I think they all have to do with the willingness to take risk and to fail, honestly.

Starting point is 00:50:47 I think that's really where it comes from. So I think there's like, 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 like, everybody makes $100 million in their startup in the first three months. Like so if your startup isn't making $100 million, you're an idiot. Like there's that stuff. There's also you're living out loud.

Starting point is 00:51:08 So like when you fail in that context, it feels very painful. But I think there's also like, you know, for elite students, like who, you know, people at these elite schools, they're hard to get into you. I went to Michigan because, quote, you're kind of smart. Michigan's a good school. You live nearby. Go apply to that one. Like, you know, nothing serious about it. But like kids in the elite schools, like, their lives are highly curated going up to getting into a school like that now, right? Like those students, like, I didn't do sports. I didn't do extracurricular. I was just like a weird nerd. You know, having to be good at math. And so I think there's that as well.

Starting point is 00:51:41 Like, if you're highly curated where you 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, you know, lead down a surprising path, right? So that's the curation as part of it. And then I, I think just like, you know, in about mid-80s when I graduated from high school, we stopped letting kids just play on their own, unsupervised outside with other kids. Like, I grew up in this neighborhood full of, it was like the faculty ghetto for this small university my dad taught at. And like, we just ran wild. It was like on the estate of the widow of Dodge Motor, founder of Dodge Motor, so we had like a couple hundred acres of swamp and fields to run around. And we did

Starting point is 00:52:23 hair-raisingly dangerous things that my currents never knew about and like really explored and had fun. I think like if you put all those pieces together, I think like there's much less of an ability and willingness and skill set about around experimenting to the point of failure, like making fool of yourself, like having bad ideas. I send like, stupid emails to Sotcha at Microsoft all the time. 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 like 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'll send him an email like a week later.

Starting point is 00:52:57 I'm like, yeah, that was a dumb idea. Sorry about that. You know, like, I've decided that wasn't a very good one. But I think like, you know, you just have like you cannot dance if you can't, if you're, you know, afraid to embarrass yourself. You cannot succeed if you're afraid to fail. Like there's just, that's just how. it is. You have to have that sense of play. You have to have that sense of, you know, it's okay if this doesn't work. I'll iterate on it. I have this personal motto,

Starting point is 00:53:21 which is like from error comes virtue because I'm a maker. I make stuff and I fuck it up all the time. Like I'm poor motor skills. So I make mistakes constantly. And then I just like figure out how to make the mistake into virtue somehow. So like I think it's a really good skill to have. Like I, it's a saying I took on this year and I really, really like it as I never had a personal motto before. I think it might be my personal motto. It's like virtue from error. Amazing.

Starting point is 00:53:50 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 as a company is negatively impacted. And it feels like for you is just having, you've done it enough times. Fine.

Starting point is 00:54:06 Okay, it's going to be fine. I launch this thing, no one cares. Email, sought to you this thing. He ignores it or he doesn't. Like, it's going to be okay. is that maybe the key of this or is there anything else that you've done to allow you to be okay with failure?

Starting point is 00:54:17 I think there's this, 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 managing, you know, tightly managing, okay, nothing's going to be surprising I'm going to be within this boundary.

Starting point is 00:54:31 I'm going to kind of 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'll climb a ladder and 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?

Starting point is 00:54:45 You have to have, you have to take bigger risks and, and, you know, have kind of more, and more, more interesting shots to have this kind of extraordinary result in your career. I feel like I always tell people, like, I think, I mean, I, I, I, I, I, I pitch this because I've observed myself and thought about, like, what has been successful in my career. It's not a thing everybody can do. Like, I've just kind of like this. I'm never really fully grew up. I'm kind of this weirdo.

Starting point is 00:55:15 I still feel I'm 57 now. I feel like I'm about 17. Like I'm still very mature and like to mess around with stuff and play with things. So not everybody can do it, but I think there's like, at the end of the day, the reason you get ahead in your career is because 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

Starting point is 00:55:34 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. Like 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, you know, very valuable. So I think lots of people like gravitate in this direction of like, let's go do unpleasant things and grind our way through the career because like that's the way to like make it. But the reality is like you should go do the thing that you feel guilty to get paid for it. There's a thing like that and do the hell out of it, right? Like do it as hard as you can.

Starting point is 00:56:09 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, like do the hell out of that. Like, 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 is the most impact you'll ever have is where you're in that mode or you're just like in the flow and, you know, 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. I think that's the career thing that makes sense to me. At least that's what I've done.

Starting point is 00:56:43 Who knows? Like, 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.

Starting point is 00:56:56 It makes me think of, I'm reading Charlie Munger's Almanac, which just came out through Stray Press. And Warren Buffett and Charlie Munger's whole philosophy is, when you find an advantage, just go huge, just go big. Like make one better year. But when you find that, go, go for it. Don't like buy a little bit at a time.

Starting point is 00:57:15 And I love that that's exactly what you're saying. Sometimes things don't make sense either. So I'll lean over and like 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 with the cat eyes. The reason it's got these weird cat eyes, by the way,

Starting point is 00:57:33 this is virtue from error right there. Like, 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 because it's redwood. And there were knots in it. So those two cat eyes are where the knots where there's another knot, like right here that I couldn't get out. But like, you know, there's two knots in there that I had to carve out of there.

Starting point is 00:57:51 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 like, you know, that's an experiment that was playing around. I kind of wanted to do this thing.

Starting point is 00:58:07 It was fun to do. Like it's a passion project. Now it's just hanging on the wall. You know, like nothing. Not everything works. Like, you know, 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 like a good example of like, I don't know, sometimes I don't even understand why I do stuff.

Starting point is 00:58:22 Like you just do it because you do it because it makes some sense to you. Many people are kind of 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. their family. I know. I realize what I'm saying is very privileged. I'm sorry about that 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 like I would do this for free? I'm so accepted about

Starting point is 00:58:46 this work. Do you recommend try to get out of that as soon as you can? Is it enjoyed as much as you can most out of it? I mean, I like I've done plenty of things for money. Like I've done plenty of jobs to make money for my family, like things I did not enjoy doing. All I can say is really like I stopped doing those things as soon as I could stop doing them. Not always as fast as I physically could, because I definitely had that Calvinist, you know, oldest boy thing of like must provide, must suffer kind of thing. So it took me a long time to realize like, no, actually like I'm really creative. I don't have to be like everybody else. I can have my own path and like, you know, I can be this weird engineer. I always joke that I'm like an engineer like two is a prime number. It's like a kind of

Starting point is 00:59:27 programmer, but not real. Like, I'm this weird nonlinear person that only barely fits in the programming world. But, like, you know, it's okay. Like, it took me a long time to figure out that I could do that, that I could, that I could, that I could be comfortable with that part of myself. And, like, I'm fortunate enough now that I've done enough things and I have enough of a connection network that people understand who I am and the value I can bring. And so I get, I get away with doing that stuff that I like doing that I'm.

Starting point is 00:59:52 So I was like, it is kind of privileged, you know, advice. And it's not something ever you can do it. 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, like, what makes you happy? What is the stuff that you feel guilty for getting away with? Like, 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 like, I can produce a lot of lines

Starting point is 01:00:19 of code every day. And then, and, you know, I asked my boss at time, like, why are you so happy with this? Like, I'm not writing anything. It's like, I don't know what you're doing. Like, everywhere you go. it gets better. So like just keep doing whatever it is you're doing. And like, you know, that was like 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. Like that's great. They're going to pay me

Starting point is 01:00:37 for talking to people all day. You know, if they seem happy, I'm happy, let me just like lean into this for a while and see where it goes. So I think you just like look for those moments. Like when somebody is willing to let you do something that you feel happy to do, surprisingly happy to do. It doesn't feel like it's the thing you quote unquote should be doing. If you get those surprises like this, think this goes back to this openness and optimism that we're talking about. You have to be receptive, you know, attentive to those moments when they show up. So I think they're there in every career if you listen for them. Like you will see stuff show up where, you know, you don't think of it as who you are, but somebody else sees it in you. And, you know, if you can be open to it,

Starting point is 01:01:18 you can do these pivots. When you talk about that, that makes me think of Seth Godin has this really important advice that's always stuck with me that no matter what job you, you're in, just try to enjoy it and do the best version of that job you can because you'll enjoy it more, you'll 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 of being a waitress at this place. I'm just going to do the best of greeting people entering the Apple store. Absolutely. Yeah, I think that's absolutely right. Like, I think, you know, or even more than that, just like find a way to bring yourself to it. Right. Like, what is the thing that you can do in this role that is unique to you that you're the most comfortable with,

Starting point is 01:01:59 right? You know, that like where you really have high impact. I don't know. I tend to be very, like it's kind of a joke because I'm a programmer. I tend to be a very binary person, right? I'm like either all in or all out on something. So whenever I do something I do it, it's just a ridiculous amount of intensity for better or for worse. So, you know, like 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 like stuff happens.

Starting point is 01:02:33 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'll share a couple of quotes that you put out someone. that I have here that I think are cool.

Starting point is 01:02:57 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'll 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 I'm like, what I'm working on is I, most of the industry right now is focused on,

Starting point is 01:03:22 when you talk about somebody who's working in AI, it's somebody who'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 makes a model bigger. And like, 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. It's like when I started with Microsoft, started working on GP4 with Microsoft in like September of last year, like my immediate reaction to it after the picking my jaw up off the floor, which we were all doing in the early days,

Starting point is 01:03:58 was, okay, this is cool. But like in some computer science sense, it's just this function, this like stochastic pure function that just like takes a character array and rearranges it and hands it back to you. Like that's not much of a building block for building programs. Like we need state and we need control flow and orchestration and call out. It's like that just kind of started me down this rabbit hole of thinking about building the semantic kernel, which we built. and then building Infinite Chatbot, which was next,

Starting point is 01:04:27 and these other projects we've been working on. And more I think about this stuff, more I do think, like, those two quotes are good quotes. Like, 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.

Starting point is 01:04:49 So pixels are expensive to produce now. Like, 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 businesses. 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? Like, you know, 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, like build the skills up.

Starting point is 01:05:19 Like, 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, but in that 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 like, this is what if. Like let's go ask some what if. So what if the agents get really, 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

Starting point is 01:05:50 state? This is my bots or docs thing. So like what if, what if we figure out a good way for you to like really highly personalized something so it knows you really well and you trust it with confidential information. If you have all 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 like the richest person in the world, you've got a hundred of the best people working for you and the chief of staff and they're tireless and they never fight with each other. Do everything you want. With that staff supporting you, like, what are you doing with software? Like how much time what are you doing when you're sitting in front of a screen where you probably communicating

Starting point is 01:06:23 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 like messing around with like 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 kind of where we're headed, I think in the world of software at least, you know, things are going to get more dynamic, more intentional, more semantic, more fluid, and more personalized. I think there's a ton of problems to be solved to make that vision real. But I think I think, you know, 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.

Starting point is 01:07:00 Like we're going, you know, phones are going to get interesting. Like that's a new device. Now we've got to go to do a whole bunch of engineering before they actually are like as useful as they are today. Right. So I think I get it. Like I think software is going to change radically now. I have the same feeling when I, when we started doing this is going back to G-Dox again.

Starting point is 01:07:18 It's another lesson. Like it's another one of these categories just like the second we got rightly up on its feet. I was like, ah, the browser is actually a platform that you can actually build real apps in. Like, I get it. Like, the world's going to change. And we had a ton of stuff to do, right? Like, nobody really understood distributed systems. Nobody understood how to build stuff in multiple places at once.

Starting point is 01:07:37 Or, you know, how you deal with replication, how you do security, like all kinds of hard. All the development patterns had to shift from waterfall to agile to CICD. Like, all this stuff had to change to, like, fully realize that world. But, like, I remember back in 2005, like, you know, this very quick, and like the people who were like the strong proponents, I think all saw this, like instantly saw that the world had changed. And like there was this new category. And I have exactly the same feeling about generative AI. Like, yeah, software is going to totally change. Like these businesses are going to totally change. It might take 10 years to like really work through

Starting point is 01:08:10 all of it. But like, yep, like door open, new room, like new game, like, fill and start coloring in the blanks, right? Like, you know, let's go. So I, that's where I think we're going. And, you know, That sounded really certain. It's 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 like we're going to learn a bunch of stuff along the way. And there's a lot of work to do.

Starting point is 01:08:37 Like a whole lot of work to do and a whole lot of unanticipated side effects are going to pop out. And, you know, 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. Like I don't. I think it's just incontrovertible that it is. It's kind of funny, like, when Gemini came out, all the press take was like,

Starting point is 01:09:01 oh, it's not that different from GP4. 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. Like, of all the takes you could have had on that. I think that was like the dumbest one, honestly. Like, you know, I don't think it's, like,

Starting point is 01:09:19 could say many things about either company. It could say many things about the science. but like, 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 was always saying, just like play with it, run, use chat, GPT, use bargain, all these things. Is there any advice you give listeners for how to approach thinking about AI,

Starting point is 01:09:47 how to integrate into the stuff they're doing? Yeah, I agree with you. Like, 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? Like even if it's an unreasonable, even if it's a goofy weird thing, right? Like, you know, I'm going to figure out how to like draw funny pictures with this programming language or whatever. Like, you know, even if it's a dumb thing like that, like picking it some arbitrary goal and being a little bit stubborn about trying to get yourself to it is a good way to learn stuff. And like, then the question is like, well, what goals are you picking?

Starting point is 01:10:20 So try to pick goals that are, you know, lead somewhere, maybe at least a little bit interesting. So, like, you know, if your goal is just like, I'm going to mess around with GPT for an hour, that's not really much of a goal, if it's like, I'm going to go try to build a GPT that can do this part of my job, let's see how close I can get.

Starting point is 01:10:39 You know, that's more interesting, right? And I do think, like, unfortunately, one of the other ways in which this is very reminiscent of the early.com era, and I think plenty of people have said this, is this sense of exhaustion in keeping up. Like, there's so much stuff going on right now. And that's, I think, another good, strong indicator that's something really big is going on, right? Where it's just, like, very, very difficult to keep track of all the stuff that's happening.

Starting point is 01:11:04 It's kind of interesting because, like, I remember just to pick on, just to kick crypto's corpse one last time. Like, there was a tweet, like, at the beginning of the year that I saw that somebody was like, yeah, it took, like the AI bros, like a week to come up with as many use cases as, you know, crypto came up with in that. decade, which definitely feels true, right? It's just like so much stuff going on. And, you know, 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 like it's hard to get the first idea. The zero to one is hard. Like 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 like do some very hard work. But once you understand that there's something there,

Starting point is 01:11:50 the cloud model works or their genera i matters and like scale works and stuff like that once you're there like the one to many all the optimization stuff like that happens in parallel it happens really quickly many many many people can do it there's a lot of energy it'll just go really fast so i think we're in that phase we're just like we're in the elaboration phase where like we understand this step and people are just filling in all the white space as fast as they can so like that's so that'll slow down eventually hopefully we'll see what the next year brings. But yeah, it's a hard time. It's hard for professionals even. Like, 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.

Starting point is 01:12:29 You have to pick good targets. You know, 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. Like maybe pick the technology based on how popular it seems if you want to learn something lots of people know. Those are all good. I think you just have these kind of mundane. I don't think it's really secret. I don't think they're kind of mundane. I don't think they're kind of mundane strategies, but you just kind of have to, like, pick some stuff and do some homework. And, you know, it's not, there's no magic single bullet to learning this stuff. You just have to run. It's like, it's like, how do I run this sprint without getting out of breath? Like,

Starting point is 01:13:03 you don't like, you're going to be out of breath, run hard. I, it's just what it is. I love that advice. And I love it connects everything else you've been talking about is find some problem. Someone has, find kind of 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 in all cylinders. It feels like it's become one of the most innovative companies out there. It feels like Satya's known now as like the most innovative best executing CEO out there potentially. That's just kind of what it feels like. Being on the inside, I'm just curious, what is it that you

Starting point is 01:13:39 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, I think very, very highly of Satcha or I wouldn't be there. I really, really like Sacha. 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.

Starting point is 01:14:05 He's a very decent, genuine, honest, high energy, you know, caring individual with a ton of empathy. He's really motivational. in a way that is not destructive. You know, he's, he's very, he believes very strongly that the leader's, you know, job is to raise the energy of the organization and he really lives that. And like, you know, 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,

Starting point is 01:14:35 you know, as deep an expert as some of the people in the room are and he's like fully in there. So like, he's really, he is a really incredible leader, like in many, in many ways. that's one thing. I think another is like that culture is very humble, honestly. Like, I mean, it's interesting going from Google to Microsoft. And I don't want to like draw comparisons or anything like that.

Starting point is 01:14:55 But like, I think there are definitely similarities and differences between companies. And I think one thing that stands out with Microsoft is it's a humble culture. It does, you know, unglomerous work all the time to make businesses be successful. So it's got that sort of mindset of just like 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.

Starting point is 01:15:19 Like this year, I've been writing a lot of patents because there's just a lot of stuff going on in the world. And, like, you know, I've written more patents this year by a lot than the rest of my career combined. And I commented on the number of like, I've written like 15 patents this year. He commented to the patent attorney that I worked with. He's like, ah, that's nothing. The chief science officer wrote 700 up in one year during the mobile boom. Like, 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.

Starting point is 01:15:47 But, like, you know, that's the kind of people that are there. Like, it's just fantastically talented people with just really deep experience at a lot of different levels. I think that's part of it too. Like, you know, 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. So he's pretty fantastic.

Starting point is 01:16:11 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 kind of the answer. And luck, you know, it's always luck too, right? Like Kevin and Sajic made a bet on Open AI, you know, a few years back, you know, and they're doing some extraordinary things with capital rays and the support of that technology and stuff like that.

Starting point is 01:16:34 And so there's, yeah, that doesn't happen by accident either. No drama there, by the way. I would know anything I hear it's calm. I hear it's calm. I think it's far away from it as possible, most under the radar startup out there. Amazing.

Starting point is 01:16:52 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 like take all of this as more of my personal opinions

Starting point is 01:17:02 and not Microsoft official stands. Like this is just me being an engineer. I'm not here as a Microsoft representative necessarily. but yeah i don't know be be is you know built stuff like solve problems built stuff like that's what it is right like you know job that job's quote around fuck around well that job is quite right like the world was built by people just like you like that's the that's the thing like you know like it's really true you know don't have to have permission like you just have to have energy

Starting point is 01:17:32 with that we've reached our very exciting lightning round are you ready right probably not great answer sam what are two or three three books that you've recommended most to other people? I like weird book. I like there's a 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 like blew all the circuits in my brain when I went to Venice. 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 In Banks, which is

Starting point is 01:18:10 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 like business advice, I think the business advice one is probably where good ideas come from. Stephen Johnson, I really like that book. I think some of the stuff about the adjacent possible.

Starting point is 01:18:30 I think it's an old book now, but I think it's pretty timely. Like still, I think he had some good stuff in there. What is a favorite recent movie or TV show that you really enjoy? 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 like the retro monster stuff like monarch and stuff

Starting point is 01:18:57 like that's kind of fun to watch. I don't know. I have like absolutely junk food taste when it comes to me. Yeah. Of creepy. creepy monsters and bugs. Yeah. I love it.

Starting point is 01:19:07 Science, shooty science things that blow up a lot. I love to repeat. By the way, have you seen Scavenger's Rain? Scavenger Rain. Scavanger Rain. Okay, you love it. It's on HBO. It's incredible. It's an animated sci-fi thing, and it's very creepy, slimy, kind of alien-y things, and it's so beautiful. Do you have a favorite interview question that you'd like to ask candidates when you're interviewing them?

Starting point is 01:19:32 I have one that got banned at Google, and I like 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've made the face, right? Like, I'm going to ask chat GPT for this answer. Well, there's a thing. Well, don't though, because like it's a, like 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

Starting point is 01:19:53 through it, but like you can figure out the answer to it in a few minutes. And so the only, 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 like back off and, you know, refuse. used to engage with it. And some people are just like, I don't know, let me roll my sleeves up to see how far I can get in this thing.

Starting point is 01:20:15 And, you know, if you do that, you can actually get through it. And those are the, I just think it's interesting. Like that's, because that's on, that's building stuff, right? Like, you know, that's a good signal like, when somebody tells you you can't write an app, word processor in the browser and you can't do collaboration, like, do you roll your sleeves up and deal with it or do you, like, fall over? And what was the question again? Just at how many zeros are at the end of 100 factorial in decimal?

Starting point is 01:20:38 And then why did it? band? I think he got known and like, you know, where. So like, I actually, the funny thing is like one of the more senior directors, actually he's a SVP now, I think. 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. Like they have this policy where like one veto is actually a good signal. Like if you're controversial as a candidate, they would like 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 like a red flag for me. So don't hire him.

Starting point is 01:21:16 I need to be a great person. So it's maybe not a good question anyways. That comes back to when your other lessons of the best ideas have some people that are just very anti that idea. Yeah. It all circles back. Next question. What is the favorite product you've recently discovered that you really love? My father-in-law and my brother-in-law worked for the American car companies. I've never had American cars. I just drive Japanese cars because I grew up in Detroit and I just hated that culture. And so recently we bought a Ford Mustang, Maki, the electric Ford Mustang. And I just love this shit out of that car.

Starting point is 01:21:49 I don't know why. It's just like a really fun car to drive. It's like very surprising to like have this American muscle car that I'm just really, it's an electric American muscle car that I really like. So that's like probably the current product I really am enjoying most right now. Next question. Do you have a favorite life motto that you often repeat to yourself? find useful share with friends or family either in work or in life.

Starting point is 01:22:11 Virtue from error, yeah. I think that's like, it's become one for me. And the more I say it, the more I like it. But I just like this idea of like, you're going to fuck up, like, make something from it and be creative with your mistakes. Like, I like that a lot. So I've been, I think that's current my, at least my current one. And say it again, just so people get it.

Starting point is 01:22:34 There's lots of different ways to say, but I just like virtue from error is probably. the cleanest way to say it or from error virtue. Final question. Apparently, you're the only person who has sold both a company to Google. I like that you already know where I'm going. Both a company and also 200 pounds of blood sausage. Yes. Both to Google.

Starting point is 01:22:55 Tell us the story. The story. So I have a friend who dropped out of the tech industry to start a company up in San Francisco called Boko Lone, which was like an artisan salumi thing in the ferry. building and so you'd make blood sausage and stuff. So there was this wonderful insane chef back in the day when Google had like really high-end cuisine in the campuses like probably 2005 or something. I know, sorry, probably 2008, something like that.

Starting point is 01:23:21 And like, so my friend Mark shows up. This chef, J.C, had the word flogra tattooed onto his knuckles. So that's, you know, that's the kind of guy. He was just super awesome. And so like I had Mark show up to like talk to J.C about buying some of those products because I was an investor in that company. and he showed up with a bag of blood sausage that was he's like here you should take this one and put it in a refrigerator and like why he's like it's dripping i'm like it's all right it's fine he's like it's dripping blood because he hadn't get the packaging right so we like showed the blood sausages to jc he cooked some of it up it was really good and he was like yeah it's awesome i'll buy a couple hundred pounds of it and like

Starting point is 01:23:57 so technically because i was an investor in that company i sold both the company rightly and 200 pounds of blood sausage to google which i think is a unique accomplishment and I would just absolutely love to meet anybody who has also done that. We'll have a party. Did you get stock, though, for that blood sausage? No, I did not get stuck in it or anything. That guy was crazy. Like, at one point, just a quick JC story. Like, at one point, Google rented some goats to, like, graze the hillside across the way.

Starting point is 01:24:28 And JC was a very non-politically correct, non-woke kind of guy. And he did not like all the, you know, sort of attitude at Google. So when these goats were across the hill, he bought a goat carcass from somewhere else and roasted it over a spit and carried it whole through the line for lunch one day to serve up, just to like completely tweak people. So that was a different time at Google. We get old days. Yeah. Amazing. Sam, that's it.

Starting point is 01:24:55 We did it. Two final questions. Where can folks find you if they want to potentially follow up on any of this? And then how can listeners be useful to you? Well, I have a substack, which is Sunday letter. from Sam that I write a letter roughly every Sunday that I've been doing for about 10 years. Not that particular. Well, I've been writing letters to my engineering team on Sunday since I was the head of engineering

Starting point is 01:25:15 at Fox, and I think that's like 12 years now or something. I just kind of started doing it to keep myself accountable and people liked it. So I just kept doing it. So now I do it in public. I repost them on LinkedIn. You can find me there. You can message me on LinkedIn if you want to. I'm hesitant to give out my personal email address because this is probably going out to a lot of

Starting point is 01:25:34 people and I don't want to get spammed. Smart, smart, man. The last funny story at Google, my email address at Google got leaked somehow, and he spammers, you know, I was kind of a little bit notorious during the early days of rightly, and so he spamer used it for what's known as a Joe job

Starting point is 01:25:50 where you send something out, fake emails out with somebody else's email address is the return, the reply to, so like several hundred million emails went out and all balanced. And so for a while, I had my own Gmail front end server that would filter them out for like a couple of weeks

Starting point is 01:26:06 until that died down. Let's make sure no one does that to you right now. Oh, yeah. You know, answer the final question, how can listeners be useful to you other than not that spam anything to you? I guess I like, the thing I guess I'm interested in is, you know, people making

Starting point is 01:26:22 interesting progress in the direction of that product vision that I talked about, you know, independent action, you know, the UI, part of this stuff generating UI, consuming UI, like all that stuff. I think I'm curious about that. I mean, an interesting idea is like, you know, anything surprising that seems, you know, that you'd like to have somebody pay attention to.

Starting point is 01:26:41 I tend to, you know, I entertain weird ideas all the time. I do my best to entertain weird ideas and kind of live what I preach. So if you think you have something that's really resonating that you think you want to have somebody pay attention to, you can connect me. I'll take a look at it. I'll do my best. I won't look at stuff that's incremental and boring. It has to be actually interesting and disruptive.

Starting point is 01:27:01 So I don't care. I'm not going to review like the 20. 27th like memo writing AI chatbot thing that plugs into Outlook or whatever. Like I don't care. I think that's a final good takeaway is that's a litmus test for are you working in something innovative, which I think has been a great theme of this conversation. Maybe something that'll piss me off. That'd be more, you know.

Starting point is 01:27:21 Sam, thank you so much for being here. My pleasure. Bye, everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcast, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review, as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lenniespodcast.com.

Starting point is 01:27:46 See you in the next episode.

Lenny's Podcast: Product | Career | Growth - How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs)

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