YouSaid · the spoken record

Sam Schillace

lines on the record: 98
first: 2024-01-11
most recent: 2024-01-11
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“I guess the thing I guess I'm interested in is people making interesting progress in the direction of that product vision that I talked about, independent action, 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 anything surprising that seems that you'd like to have somebody pay attention to. I tend to 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. I don't care. I'm not going to review the 27th memo writing AI chat bot thing that plugs into Outlook or whatever. Like, I don't care.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“The last funny story at Google. My email address at Google got leaked somehow and he spammer. I was kind of a little bit notorious during the early days of Wrightley. And so he spammer used it for what's known as a Joe job where you send something out, fake emails out with somebody else's email address as the returned reply to. So like several hundred million emails went out and all bounced. And so for a while, I had my own Gmail front end server that would filter them out for like a couple weeks till that died down.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Well, I have a substack, which is Sunday letters 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 at Box, 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. And so now I do it in the 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 people and I don't want to get spammed.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“No, I did not get Anything. That guy was crazy. Like at one point, just a quick JC story. At one point, Google rented some goats to graze the hillside across the way. And JC was a very non-politically correct, non-woke kind of guy, and he did not like all the 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 like completely tweak people. So that was a different time at Google.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Story. So I have a friend who dropped. And like, so my friend Mark shows up, the chef JC had the word flag ra tattooed onto his knuckles. So that's, you know, that's the kind of guy he was. He was just super awesome. And so like I had Mark show up to like talk to JC 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. They hadn't got 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, 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.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“There's lots of different ways to say it, but I just like virtue from error is probably the cleanest way to say it, or from error virtue.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“You 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, you know, I just like this idea of you're going to fuck up, like make something from it and be creative with your mistakes. I like that a lot. So I've been, I think that's my current one.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“My father in law and my brother-in-law worked for the American car companies, and I've never had American cars. I just drive Japanese cars because I grew up in Detroit and just like hated that culture. And so recently we bought a Ford Mustang Maki, the Electric Ford Mustang. And I just loved the shit out of that car. And I don't know why. It's just like a really fun car to drive. It's like very surprising to have this American muscle car that I'm just really, this electric American muscle car that I really like. So that's my probably the current product I really am enjoying the most right now.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“I think he got known and like, you know. Actually, the funny thing is one of the more senior directors actually is an SVP now, I think. Dave Bezaris, I interviewed him when he came in and I asked him that question. And his response was, I don't do math next question. And so I failed him. I was the veto. And they have this policy where we're friends now. They have this policy where like one veto is actually a good signal. Like if you're controversial as a candidate, they would like to 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. And he turned out to be a great person. So it's maybe not a good question anyways.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“There's a thing. Well, don't though, because the reason I ask it is it seems like an unreasonable and impossible answer. And if you sit down and think about it a little bit, I'm not going to tell you how to reason through it, but you can figure out the answer to it in a few minutes. And so the only 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 to engage with it. And some people are just like, I don't know, let me roll my sleeves up and see how far I can get in this thing. And if you do that, you can actually get through. And those are the, I just think it's interesting. Because 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 you roll your sleeves up and deal with it or do you fall over?”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“I am one that got banned at Google and I liked it. I still think it's a fun question. It's how many zeros are at the end of 100 factorial? And the reason I like it, yeah, it's like you've made the face, right?”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“My favorite one right now, my guilty pleasure is watching Gary Oldman be a completely disgusting over the hill British spy in slow horses, which is pretty fun. And I'm actually having a little fun with the retro monster stuff, like monarch and stuff like that. It's kind of fun to watch. I don't know. I have absolute junk food taste when it comes to.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“I like Weird books. I like business 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 probably the creepiest and hardest book I've ever read, but it's a very interesting psychological deep dive. So those are both fiction. If you're looking for business advice, I think the business advice one is probably where good ideas come from, like Steven Johnson. I really like that book. I think some of his stuff about the adjacent possible, I think it's an old book now, but I think it's pretty...”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Fuck around. Well, that job is quite as right. Like the world was built by people just like you. Like, that's the thing. It's really true. You don't have to have permission. You just have to have energy”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Mostly, I think probably take all of this as more of my personal opinions and not Microsoft's 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. B is not build stuff, like solve problems, build stuff. Like that's what it is, right? Like, you know, that job's quote. Fuck around.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. 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. 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 Sachi made a bet on OpenAI a few years back, you know, and they're doing some extraordinary things with capital raise and the support of that technology and stuff like that. And so that doesn't happen by accident either.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Very humble, honestly. It's interesting going from Google to Microsoft, and I don't want to draw comparisons or anything like that, but I think there are definitely similarities and differences between companies. And I think one thing that stands out with Microsoft is it's a humble culture does unglamorous 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, 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 I've written more patents this year by a lot than the rest of my career.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“A couple of things. First of all, I think very, very highly of Satcha, or I wouldn't be there. I really, really like Satcha. He is very much what he appears to be from the outside. I've had plenty of candid private conversations with him and watched him in meetings and stuff like that. He's a very decent, genuine, honest, high-energy, caring individual with a ton of empathy. He's really motivational. In a way that is not destructive. You know, he's very, he believes very strongly that a leader's 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 and stuff and how much he understands about something that I know he's not as deep an expert as some of the people in the room are. And he's like fully in there. So like he's really, he is a really incredible leader in many in many ways. That's one thing. I think another is like that culture is.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Pick some stuff and do some homework, and there's no magic single bullet to learning this stuff. You just have to run. It's like, how do I run this sprint without getting out of breath? Like, you don't like you're going to be out of breath. Run hard. It's just what it is.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. You have to pick good targets. Pick a goal in your domain that would matter to you if you can get to it and then go try to solve that problem with some specific technology and get to know that technology. 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 stuff. 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 strategies, but like you just kind of have to like.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 like the cloud model works or their generative AI 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 where 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 that'll slow down eventually, hopefully. We'll see what the next year brings.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 the sense of exhaustion and keeping up. Like there's so much stuff going on right now. And that's, I think, another good strong indicator that something really big is going on, right? Where it's just like very, very difficult to keep track of all the stuff that's happening. It's kind of interesting because I remember going just to pick on just to kick crypto's corpse one last time. Like there was some tweet like at the beginning of the year that I saw that somebody was like, yeah, I took like the AI bros like a week to come up with as many use cases as crypto came up with in a decade, which definitely feels true, right? It's just like so much stuff going on. And I think you just have to kind of 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.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 draw funny pictures with this programming language or whatever. Even if it's a dumb thing like that, like picking at 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, what goals are you picking? So try to pick goals that are 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 chat 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. That's more interesting, right? And I do think, unfortunately.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Gemini came out. The press take was like, oh, it's not that different from GPE4. I guess we're done with AI now. We can go back to bed. I'm like, that was 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. I don't think 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.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. Category, and I have exactly the same feeling about generative AI like, yep, software is going to totally change, like these businesses are going to totally change. It might take 10 years to really work through all of it, but like, yep, like door open, new room, like new game, like go and start coloring in the blanks, right? Let's go. So that's where I think we're going. And 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, like a whole lot of work to do and a whole lot of unanticipated side effects are going to pop out. And there's just a whole lot of stuff to get that to be real the way there was with all of the last transformations. But I think this is just a giant category shift. I think it's just incontrovertible that it is. It's kind of funny when...”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. Like we're going, you know, phones are going to get interesting. Like that's a new device. Now we got to go do a whole bunch of engineering before they actually are like as useful as they are today, right? So I think I get it. I think software is going to change radically now. I had the same feeling when we started doing this is going back to GDOCs again. It's another lesson. It's another one of these category shifts. Like the second we got rightly up on its feet. And I was like, ah, the browser is actually a platform that you can actually build real apps in. I get it. 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 or 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.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Have all those things, you're just going to spend a lot of time talking to that agent. Like it's like, what would you do if you imagine you're like the richest person in the world and you've got 100 of the best people working for you and a chief of staff and they're tireless and they never fight with each other, do everything you want? Like 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 intention and you're probably consuming some in 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, they're more personalized. I think there's a ton of problems to be solved to make that vision real. But I think”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 skills up. 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, like done, right? So those pixels got really free. But and the similar things are happening in the business world as well. And I think it's just going to start to happen everywhere. So you can draw 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 complicated things. What if the multimodal stuff gets really good so that they can both consume and produce dynamic UI like I was talking about? What if we figure out a good way to store state? This is my bots or docs thing. So like what if what if we figure out a good way for you to like really highly personalize something so it knows you really well and you trust it with confidential information?”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“It and hands it back to you. 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. And so that just kind of started me down this rabbit hole of thinking about building semantic kernel, which we built and then building the infinite chatbot, which was next, and these other projects we've been working on. And more I think about this stuff, the more I do think those two quotes are good quotes. I think what's going to happen over time, I actually think we're at the beginning of this just gigantic disruption in the software industry. I think the way that the internet made distribution of information free, I think AI is going to make pixels free. So pixels are expensive to produce now. 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.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Yeah, I think both of those are really true. So I'm like, what I'm working on is most of the industry right now is focused on when you talk about somebody who's working in AI, it's somebody who's creating models. It's somebody who's figuring out how to do some new open source model or somebody who's doing some new training or make some model bigger. And I think that's very, it's valid, useful work. It's just not the kind of work I like to do very much. And a lot of people are doing it. And so I'm an app builder. I'm a tool builder. And so I don't create models, I consume them, right? I want to build things around them. And so when I started with Microsoft, started working on GP4 with Microsoft in September of last year, like my immediate reaction to it after picking my jaw up off the floor, which we were all doing in the early days was, okay, this is cool, but like in some computer science sense, it's just this function, this stochastic pure function that just like takes a character away and rearrange.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Absolutely. Yeah, I think that's absolutely right. Like, I think, you know, or, and 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, you know, unique to you that you're comfortable, the most comfortable with 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 anyways. I get things done.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“I could do something else, and it's kind of fun. I like talking to people all day, that's great, they're going to pay me for talking to people all day. If they seem happy, I'm happy. Let me just lean into this for a while and see where it goes. So I think you just look for those moments when somebody is willing to let you do something that you feel happy to do, surprisingly happy to do, like doesn't feel like it's the thing you quote unquote should be doing. If you get those surprises, like this, I think this goes back to this openness and optimism that we're talking about. Like you have to be receptive in attentive to those moments when they show up. I think they're in every career if you listen for them. Like you will see stuff show up where 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, you can do these pivots.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“That people understand who I am and the value I can bring. And so I get away with doing that stuff that I like doing that I'm. So it is kind of privileged advice. And it's not something everybody can do at every stage in their career, certainly earlier stages. You often have to make compromises. But I still think it's worth paying attention to. When you're working, like what makes you happy? What is the stuff that you feel guilty for getting away with? When I started managing people, I couldn't understand why people were paying me and I wasn't writing code because all of my energy was attached to like I can produce a lot of lines of code every day. And I asked my boss at the time, like, why are you so happy with this? Like, I'm not writing anything. He's like, I don't know what you're doing. Like everywhere you go, it gets better. So just keep doing whatever it is you're doing.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 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 just like kind of a programmer, but not really like this weird nonlinear person that only barely fits into the programming world. But like, you know, it's okay. Like, I took me a long time to figure out that I could do that, that I could, that I could be comfortable with that part of myself. And I'm fortunate enough now that I've done enough things and have enough of a connection network.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Like, 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 you do stuff. Like, you just do it because you do it because it makes some sense to you.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Sometimes things don't make sense either. So I'll lean over and show you for people with the video. That's an instrument I made. It's an instrument. So the top of that's a piece of redwood. This one right behind me with the cat eyes. The reason it's got these weird cat eyes, by the way. This is virtue from error right there. I dug this piece of wood out of the forest. It'd been sitting on the forest floor for 80 years trying to not rot and doing a pretty good job of it because it's redwood. And there were knots in it. So those two cat eyes are where the knots were. There's another knot 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. 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 closer to the top, stuff like that. But like, you know, that's an experiment. That was playing around. I kind of wanted to do this thing. It was fun to do. It's a passion project. Now it's just hanging in the wall. You know, like not everything works.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“If you get pleasure from doing something that people want to pay you for, do it, the best you can do it as hard as you can do it. And if that's messing around and playing around with cool ideas, do the hell out of that. Work doesn't necessarily have to be hard. It often is, but it doesn't have to be. And the best case is that it is. The most impact you'll ever have is where you're in that mode or you're just like in the flow and doing your thing and you're happy to do it and you can't quite believe they pay you and you don't understand how you're getting away with this, but it's super cool anyways. I think that's the career thing that makes sense to me at least that's what I've done. Who knows? It's all luck sometimes. So it's hard to replicate these. Everybody has a different path.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Weirdo, 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, you know, at the end of the day, what you get, 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 were good at that you did with a lot of intensity that wound up having impact, right? Like, and so I think the good at part of it is hard to. 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 gravitate in this direction of like, let's go do unpleasant things and grind our way through the career because that's the way to make it. But the reality is you should go do the thing that you feel guilty to get paid for if there's a thing like that and do the hell out of it, right? Like do it as hard as you can.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“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 tightly managing, okay, nothing's going to be surprising. I'm going to be within this boundary. 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 the ladder. It takes 30 years and whatever. I don't have the patience for that. And I think the way you get extraordinary returns is you do extraordinary things, right? You have to have to take bigger risks. and have kind of more interesting shots to have this kind of extraordinary result in your career. I feel like I always tell people, I think, I mean, I pitch this because I've observed myself and thought about what has been successful in my career. It's not a thing everybody can do. Like I've just kind of like this. I'm never really fully grew up. I'm kind of this.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Know you just have you cannot dance if you can't if you're afraid to embarrass yourself. You cannot succeed if you're afraid to fail. That's just how it is. You have to have that sense of play. You have to have that sense of, you know, it's okay if this doesn't work. I'll iterate on it. I have this personal motto, 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 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 the saying I took on this year and I really, really like it as my, I never had a personal motto before. I think it might be my personal motto. Virtue from air.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“I sound like stupid emails to Satcha 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, and I'll send him an email like a week later. I'm like, yeah, that was a dumb idea. Sorry about that. You know, like.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Everything I do has to have a reason and an output. It's very hard to just mess around and do something that might lead down a surprising path, right? So that's the curationist part of it. And then I think just like in about the mid-80s, when I graduated from high school, we stopped letting kids just play on their own unsupervised outside with other kids. Like I grew up in this neighborhood full of the faculty ghetto for this small university my dad taught at. We just ran wild. It was like on the estate of the widow of Dodge founder of Dodge Motor. So we had like a couple hundred acres of swamp and fields to go run around. And we did hair-raisingly dangerous things that my parents never knew about and really explored and had fun. I think like if you put all those pieces together, I think there's much less of an ability and willingness and skill set about around experimenting to the point of failure, like making a fool of yourself, like having.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“You see a lot of filtered content. And that filtered content presents low probability events like five and six sigma events as though they were normal. So you see everybody makes $100 million in their startup in the first three months. So if your startup isn't making $100 million, you're an idiot. There's that stuff. There's also you're living out loud. So like when you fail in that context, it feels very painful. But I think there's also like, you know, for elite students who at these elite schools, they're hard to get into. I went to Michigan because, quote, you're kind of smart. Michigans are 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 and I didn't do extracurricular. I was just like a weird nerd at, you know, having to be good at math. And so I think there's that as well. Like if you're highly curated where you spent a lot of your life thinking.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“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. I think that's really where it comes from. So I think there's like”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“This is a really interesting question. I may actually write, I've been thinking about writing a book that'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. 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 there's this weird thing I notice where 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 PCU is this stupid toy, whatever. It's not real computing. Go on a mainframe or whatever. And my attitude was like, out of the way, old man, like just like you're irrelevant. I'm going to go do this thing. It's awesome. Like, go, go, go. And now when I talk to kids, I actually had a slide up at Michigan when I was talking recently that was titled OK Doomer, that when the professor actually put it up there. Because the generation is very pessimistic and doesn't seem to be quite as engaged and energetic about solving problems. And I've been puzzling through it. And I think maybe there's like a bunch.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“I don't know. I think that's I like playing around. I think a lot of the good product ideas, most of the good product ideas actually come up from engineering. So I think there's a lot to be said for get familiar with tools, particularly like weird esoteric combinations of tools can often be useful. If you understand two or three things, like at Google, 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. And both a back-end language, which is the monitoring language Borgmon, a middle tier language, which was Java and a front language, which is JavaScript. Like no one else would do that full stack. I think it's useful to have that broad perspective sometimes.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Even the early days of Rightley, like the very, I mean, we had a goal from the beginning. The beginning was like, can I write a word processor in the browser? That was literally the problem statement. It was like, I have content edible, I have Ajax or JavaScript. Can I put these together in something that feels like a word processor? Let's go do that. It's kind of half messing around with tech, but it's also half an actual goal, an actual goal.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Like just playing, you know, 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. I wonder if I can build this thing. Let me grind away at that for a week and see how close I can get, see what I learned about why it's hard. That's probably better than just let me poke at JavaScript for a while.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“Self monitor and self correct and bug themselves that can build things that are roughly that scale of complexity. That's valuable. Like that would be a valuable thing to have. It's kind of interesting too because that system already, it's produced a bunch of good insights. One of them is it's kind of complicated and hard to debug it. It's this asynchronous system of stochastic agents that's a lot of stuff to kind of deal with. So we wrote a debugger agent. And debugger agent watches stuff and when there's a problem somewhere, it goes and figures out what the problem is and it 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. But, you know, it's like very helpful as an assistant that sits there and does this. So 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.”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source
“I'm guilty of that. 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 like I pick what I call North Stars that I think are 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. We're trying to figure out how much independent work they can do without a person holding their hand. And so a nice domain to test that out in is programming because you don't have a whole lot of, you just like give something a Python environment, a file system and that's it. And like that's all it needs. And so you're not distracted by connectivity issues or whatever. So one of the problems right now is like go write VI in Python. That's a problem I could give to an intern and it would take them a summer to do some halfway decent job of it. It's a thing you could expect a reasonably competent programmer to do, mostly independently. And so like it should be possible for the system if it's independent at all to go do that. So is that useful by itself? No, because we already have VI. It doesn't matter. But like if we build a system of programming agents that can”
2024-01-11 · Lenny's Podcast · How to be more innovative | Sam Schillace (Microsoft deputy CTO, creator of Google Docs) · IDENTIFIED FROM THE TRANSCRIPT · source